A synergistic combination of SDS and TX-100 for the catalytic oxidation of an aromatic alcohol in aqueous media

A synergistic combination of SDS and TX-100 for the catalytic oxidation of an aromatic alcohol in aqueous media | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article A synergistic combination of SDS and TX-100 for the catalytic oxidation of an aromatic alcohol in aqueous media Atanu Rakshit, Suman Chowdhury, Animesh Acharjee, Kalachand Mahali, and 3 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-2861036/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 12 Jul, 2023 Read the published version in Research on Chemical Intermediates → Version 1 posted 8 You are reading this latest preprint version Abstract In aqueous medium, oxidation of an aromatic alcohol (4-chlorobenzyl alcohol) was carried out in aqueous mixed micellar media under pseudo first order condition by chromic acid at 30 ºC. The micellar microenvironment constituted by anionic SDS and nonionic TX-100 surfactants showed excellent catalytic performance in course of oxidation, individually. In addition to that the nanomicelle produced by combination of SDS and TX-100 was found to be effective microheterogeneous catalyst for the aforementioned oxidation process. Use of two organic precursors, Phen and Bpy, entitled as promoter, made the reaction faster in presence of single micelle and mixed micelle. The fabrication of mixed micelle was confirmed by UV, 1 H-NMR and 2D NOESY study. The maximum improvement in reaction kinetic was noticed when SDS/TX-100 surfactants mixture introduced along with Bpy promoter. Aromatic alcohol Oxidation Nanomicellar catalysis SDS/TX-100 mixed micelle CMC lowering Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 1. Introduction Micelles are generally simple spherical supramolecules, formed by amphiphiles in aqueous medium. Micellar system normally appears as macroscopically homogeneous due to the existence of colloidal size aggregates however in reality they are microheterogeneous system and function as nanoreactors for numerous organic reactions. 1 Micelles can accelerate and/or inhibit a chemical reaction relative to the same reaction performed in an aqueous medium. At present aqueous micellar technology are used efficiently to perform many organic reactions in water and the recreation of various organic transformations in aqueous micellar medium has several advantages 2 – 6 . The beauty of aqueous micellar media is that it is a green environment, can substitute the hazardous volatile organic solvents that are practically difficult to remove from the organic synthesis. 7 – 11 Noticeably, exercise of mixed micelle in various purposes including emulsification, dispersion, detergency, targeted drug delivery etc. 12 – 18 instead of single one shows very significant performance due to the synergistic effect of constituent surfactants. In our recent works we have investigated the catalytic efficacy of mixed micellar media in oxidation of several organic substrates 19 – 21 along with the physiochemical properties of different mixed micellar composition by different techniques including conductivity, DLS (dynamic light scattering), spectrofluorimetry, etc. 22 – 26 In this report we have accounted the effect of anionic-nonionic mixed micelle on the oxidation kinetic of an aromatic alcohol using the transitional metal oxidant. In addition to, the aggregation behaviour of binary surfactant mixtures has been analyzed following the outcomes of 2D-NOESY. Chromium(VI) compounds has long been used as potential oxidant for oxidation of alcohols (aliphatic and aromatic) and aldehydes in water or organic medium and has been used for years. 27 Use of chromic acid as oxidising agent in aqueous medium is really interesting on account of its distinct aqueous chemistry in H 2 SO 4 medium and generation of reactive short-live intermediate species during the course of electron-transfer reaction. Noticed that Cr(III) is produced at the end of redox transformations, and some report about the usefulness of Cr(III)-picolinate as nutritional supplement encourages to introduce chromium metal as oxidizing agent. Previous works on chromic acid directed oxidation of many organic compounds suggests that, the oxidation rate was further influenced by utilising some N -bases such as 1,10-Phenanthroline, 2,2'-Bipyridine, 2-Picolinic acid, etc. 31 – 36 which was materialized as Cr(III)- N -base complexes at the end of oxidation. These heteroaromatic N -bases compounds are better termed as promoter instead of catalyst. 35 , 36 In our recent work we have manifested the oxidation kinetic of 4-chlorobenzyl alcohol in single micellar medium following pseudo-first order condition. 33 Herein, we have uncovered the role of SDS/TX-100 mixed micellar media on the oxidation of same aromatic alcohol by chromic acid at 30°C. The product, 4-chlorobenzaldehyde, is an important intermediate produced in pharmaceutical industry mainly. 37 – 39 The functions of two promoters Bpy and Phen on the oxidation kinetic has been scrutinized in microheterogeneous media. The significant growth of reaction rate was observed when Bpy participated in oxidation mechanism and nanomicellar media (SDS and SDS/TX-100) accommodate the reactant species fructuously during the course of reaction. 2. Experimental 2.1. Materials 4-Chlorobenzyl alcohol (> 98.0%, AR, Sigma-Aldrich, USA), Sulphuric acid [H 2 SO 4 ] (> 97%, AR, Merck, India), potassium dichromate [K 2 Cr 2 O 7 ] (> 99.0%, AR, BDH, India), Triton X-100 [TX-100] (98%, AR, HIMEDIA, Maharashtra, India), sodium dodecylsulfate (> 90%, AR, Merck, India), 1, 10-phenanthroline (> 99.0%, AR, Merck, India), 2, 2´-bipyridine (> 98%, AR, Spectrochem, Mumbai, India), chloroform-d (CDCl 3 ) (> 99.0%, AR, Sigma-Aldrich, USA), deuterium oxide (D 2 O) (> 99.0%, AR, Sigma-Aldrich, USA) were used as received without further purification. All the aliquots were made using double distilled water (specific conductance 2.0 µS cm − 1 ). 2.2. Instrumentation Temperature controller attached UV-Vis-2450 (SHIMADZU) spectrophotometer was used to monitor the reaction kinetic. In preparing the reaction solutions sonicator, ultrasonic cleaner (CD 4820), and Sartorius BSA 224S-CW weighing balance were used. The Perkin Elmer Spectrum 2 and Bruker ASCEND 400 MHz spectrometers were used to record the FTIR and 1 H-NMR spectrum of the reaction product, respectively. 2.3. Kinetics measurements The oxidation reaction (in presence of surfactant and/or promoter ) has been performed maintaining the pseudo first order condition. For instance, the substrate (4-chlorobenzyl alcohol) concentration (40×10 − 4 mol dm − 3 ) in large excess (≥ 10- fold ) relative to the Cr(VI) (4×10 − 4 mol dm − 3 ) has been taken in aqueous sulphuric acid (0.4 mol dm − 3 ) medium at 30°C (± 0.1°C). The gradual decrease of absorbance of Cr(VI) with respect to regular time interval at λ max = 440 nm has been recorded with the UV-Vis spectrophotometer to show the progress of the reactions. The slope values of the plots of -ln(Abs) 440 vs time(t) were used to calculate the rate constant ( k obs ) values and t 1/2 values using the formula (ln2/ k obs ). 2.4. Product analysis and stoichiometry In case of uncatalyzed (without surfactant) and unpromoted (without promoter) reaction, the yellow-orange Cr(VI) solution turned into pale greenish-blue coloured solution (Cr(III)) ensured the completion of reaction. After extracting the reaction mixture using diethyl ether followed by evaporation of the solvent, the product was obtained mixed with a slight portion of unreacted solid substrate. Then the product was isolated from the impurity-like substrate by successive treatment with sodium bisulphite solution and solvent extraction. 40 , 41 The recrystallized product and its 2,4-DNP derivative, further recrystallized with ethanol, gave melting points 46°C and 265°C respectively conformed the corresponding carbonyl product. Spectroscopic analysis (IR and 1 H-NMR) also confirmed the product is 4-chlorobenzaldehyde. Spectrophotometric titration of varying concentrations of substrate using Cr(VI) of known concentration in presence of 0.4 mol dm − 3 sulphuric acid gave the following reaction with stoichiometric coefficients. The absorbance values in all cases were taken at 580 nm after 48 hours to get steady measurements. 2.5. Precautions The alarming toxicity and carcinogenicity of Cr(VI) has limited us the drainage of the same in the experiment. Excessive discharging of surfactants in water bodies also endanger the aquatic lives. 42 , 43 Hence, SDS and TX-100 were recycled and thereby eliminating from the product mixtures (after completion of reaction) through the precipitation with calcium salt and thermal precipitation respectively. 44 3. Results 3.1. UV-Vis spectral analysis and kinetic outcomes The successive drop in absorbance with respect to equal time interval, provided in Fig. 1 , showed the progress of reaction which was performed in absence of surfactant and promoters. The corresponding –ln(Abs) vs time plot (Fig. 2 ) for every kinetic run help to figure out overall kinetic profile, tabulated in Table 1 and Table 2 . The rate constant ( k obs ) values along with respective half-life (t 1/2 ) were registered in Table 1 and Table 2 , in which Table 1 represents the single as well as binary surfactant mediated oxidation kinetics and Table 2 highlights the kinetic parameters for the reaction performed in presence of surfactants and promoters. The tables show that both the single micelles and the mixed micelle have the capability to amplify the reaction rate constant values that indicate the rate enhancement of oxidation process. Noticed, two promoters Phen and Bpy also accelerated the reaction rate. In addition to single micelles the binary mixture of surfactants in combination with promoters enhanced reaction rate significantly, as realized from the histogram (Fig. 3 ). Under pseudo-first order condition in presence of large excess of substrate, Cr(VI) ions could surely be reduced to Cr(III) as the reaction proceed. The formation of Cr(III) pale blue coloured solution, was confirmed by the appearance of absorption maxima at 580 nm and 403 nm. (Figure S1 ). Again, after the completion of the reaction the pale violet colour was observed in presence of Bpy having λ max = 547 nm and pale pink colour was noticed for phen governed oxidation (λ max = 550 nm) towards (Figure S1 ). Actually, in absence of promoter final reduced product is aqua-Cr(III) species but in presence of promoters, Cr(III)-promoter complex were generated as the reduced species (Figure S1 ). 45 , 46 Under the experimental condition the single isosbestic point in the UV-Vis spectrum of each reaction suggests the possibility of generation of Cr(IV) and Cr(V) like intermediates with very low concentration (Figure S2). Table 1. Rate constant ( k obs ) and half life ( t 1/2 ) of oxidation reaction in presence of SDS, TX-100 and SDS/TX-100 mixed micelle. 10 3 ×Micellar catalyst [mol dm -3 ] 10 4 × k obs [s -1 ] t 1/2 [min] SDS TX-100 None None 0.48 ± 0.01 240.62 10 20 30 40 50 None 1.85 ± 0.01 2.52 ± 0.01 3.07 ± 0.01 3.51 ± 0.01 3.92 ± 0.02 62.43 45.83 37.62 32.90 29.46 None 10 20 30 40 50 1.14 ± 0.01 1.36 ± 0.01 1.58 ± 0.01 1.81 ± 0.01 2.02 ± 0.01 101.31 84.92 73.10 63.81 57.17 10 10 20 30 40 50 1.70 ± 0.01 2.20 ± 0.01 2.62 ± 0.02 2.99 ± 0.01 3.38 ± 0.01 67.94 52.50 44.08 38.63 34.17 20 30 40 50 10 2.83 ± 0.01 3.79 ± 0.01 4.41 ± 0.02 4.93 ± 0.01 40.81 30.47 26.19 23.42 Table 2 Rate constant ( k obs ) and half life (t 1/2 ) of oxidation reaction in presence of promoter mediated by aqueous SDS, TX-100, and SDS/TX-100 mixed micelle. 10 3 × [SDS] mol dm − 3 10 3 × [TX-100] mol dm − 3 Promoter 10 4 × [Promoter] mol dm − 3 10 4 × k obs [s − 1 ] t 1/2 [min] None None Phen 5 10 15 20 25 1.01 ± 0.01 2.03 ± 0.01 2.98 ± 0.02 4.05 ± 0.02 4.94 ± 0.01 114.35 56.89 38.76 28.52 23.38 Bpy 5 10 15 20 25 0.84 ± 0.01 1.54 ± 0.03 2.22 ± 0.01 2.98 ± 0.01 3.72 ± 0.02 137.50 75.00 52.03 38.76 31.05 10 None Phen 5 10 15 20 25 2.22 ± 0.01 4.32 ± 0.03 5.87 ± 0.02 9.34 ± 0.01 11.74 ± 0.02 52.02 26.73 19.67 12.36 9.83 Bpy 5 10 15 20 25 23.72 ± 0.01 44.62 ± 0.02 79.55 ± 0.01 106.70 ± 0.03 146.50 ± 0.03 4.86 2.58 1.45 1.08 0.79 None 10 Phen 5 10 15 20 25 1.53 ± 0.01 3.92 ± 0.02 5.35 ± 0.01 8.52 ± 0.01 12.68 ± 0.02 75.49 29.46 21.59 13.55 9.10 Bpy 5 10 15 20 25 1.42 ± 0.02 3.42 ± 0.01 4.87 ± 0.01 7.86 ± 0.02 11.58 ± 0.01 81.33 33.77 23.71 14.69 9.97 10 10 Phen 5 10 15 20 25 2.48 ± 0.01 4.86 ± 0.02 6.65 ± 0.01 9.98 ± 0.02 12.44 ± 0.03 46.57 23.76 17.36 11.57 9.28 Bpy 5 10 15 20 25 22.99 ± 0.01 44.32 ± 0.02 78.97 ± 0.03 105.72 ± 0.02 144.16 ± 0.02 5.02 2.60 1.46 1.09 0.80 4. Discussion 4.1. Product analysis The IR spectrum of the separated product exhibits stretching frequency at 1688.39 cm − 1 corresponding to the C = O bond of aromatic aldehyde group (Figure S3) and the recrystallized 2, 4-DNP derivative of the product displays stretching frequency at 1615 cm − 1 and 3285 cm − 1 pertaining to C = N and N–H bonds, respectively (Figure S4). The 1 H-NMR spectrum (Figure S5) of the product (carried out in CDCl 3 solvent) shows a singlet peak with chemical shift value at 9.9 ppm confirms the aldehydic proton. The peaks near 8 and 7.5 ppm in the spectrum indicate two different type of protons, one is ortho to –CHO and another is ortho to –Cl group (Table S1 ). The comprehensive analysis of FTIR and 1 H NMR spectra confirmed the oxidized product which is 4-chlorobenzaldehyde. 4.2. Mechanism of the reaction The mechanistic pathways of the oxidation can be classified into four different types (i) uncatalysed and unpromoted path, (ii) promoted path, (iii) micellar catalysed path and (iv) micellar catalysed promoted path. 4.2.1. Uncatalysed and unpromoted path The plausible mechanism of the uncatalysed and unpromoted reaction is already proposed in the previous work. 33 Basically, the first step is the formation of neutral chromate ester species between the substrate and chromic acid (H 2 CrO 4 ). The neutral ester species was then decomposed as governed by H + ion, this is the r/d step, to give the actual oxidized product and Cr(III) species. 47 This is simple mechanistic pathway for the chromic acid directed oxidative transformation of 4-chlorobenzyl alcohol to 4-chlorobenzaldehyde in aqueous media only. It would be interesting to highlight on the reaction kinetic which was affected by micellar media in presence of promoter significantly. 4.2.2 Promoted path The reaction proceeds with much faster in presence of heteroaromatic N -bases: Phen and Bpy, than the unpromoted one (Table 2 ). The rate constant values in presence of Phen and Bpy vary in the order k obs (Phen) > k obs (Bpy) (Fig. 4 ). As already reported that in promoted path the case is quite different due to the formation of Cr(VI)-promoter complexes primarily, which gets reduced to Cr(III)-promoter complexes later. The Cr(VI)-promoter complexes are actual oxidants, recognized as active oxidant species (AO + ) (Figure S6). 33 The generated active oxidant (AO + ) species then undergoes acid catalysed decomposition to form the product. The observed rate constant variation with two promoters can be explained on account of the generation of stable active oxidants (AO + ). Herein two promoters (Phen and Bpy) are acts as chelating agents, having two nitrogen donor sites, and fabricates the stable chelated complexes with Cr(VI) centre. The donor sites in 1, 10-Phenanthroline remain in cis configuration with three stable aromatic rings, so rate of formation of active oxidant (AO + ) is higher compare to the active oxidant species generated by 2, 2′-Bipyridine. Actually, in stable conformation the N -donor sites of Bpy remains in trans orientation mutually and therefore in order to get converted into s-cis conformation an activation energy barrier must be overcome to formulate such chelated complex or so called active oxidant species. This phenomenon explains the cause of greater rate in case of Phen (Scheme S1 and Scheme S2). 4.2.3 Micellar catalysed path In presence of two surfactants SDS and TX-100 and in SDS/TX-100 mixed micellar medium the oxidation kinetics were amplified compared to the reaction performed in aqueous medium only (Table 1 ). Micellar catalysed unpromoted path can be classified into (i) single micelle catalysed and (ii) mixed micelle catalysed path. 4.2.3.1 Single micelle catalysed path In single micelle catalysed path, both SDS and TX-100 enhance the rate of oxidation and the observed order of rate constant is k obs (SDS) > k obs (TX-100) (Table 1 ) (Fig. 5 ). In presence of anionic and nonionic micelle, the schematic representation of interaction between reactant molecules with micelle like surfactant aggregates is shown in Figure S7. In aqueous medium chromic acid is present as HCrO 4 − , but in micellar media protonation of HCrO 4 − occurs and neutral H 2 CrO 4 forms, this neutral species can bind with anionic and neutral surfactants through ion–dipole interaction and H-bonding interaction at the stern layer of micellar surface and the reaction proceeds smoothly. 47 In micellar media (SDS and TX-100), the hydrophobic part of aromatic alcohol remains in the palisade layer and the polar hydrophilic part remains oriented toward the stern layer of micelle and thereby assists the solubilisation of substrate in aqueous micelle medium. 48 In general, aromatic alcohol oxidation depends on two main steps. As mentioned earlier that the formation of neutral chromate ester and subsequent proton (H + ) catalysed decomposition of the same in the r/d step take places in aqueous media only (Scheme 1 ). In anionic SDS micelle, on account of the strong attractive force, the H + ions can move towards the chromate ester faster than in neutral TX-100 micellar system, results further expediting the oxidation kinetics. Though, the moderate rate enhancement in TX-100 may be attributed to the togetherness of the neutral Cr(VI) species with the micellar aggregates by some supramolecular interaction (ion–dipole interaction and H-bonding). 4.2.3.2 Mixed micelle catalysed path Above their individual CMC, TX-100 in combination with SDS shows a different λ max (hypochromic shift) from that of TX-100 only indicating a possibility of mixed micelle formation. 48 The CMC of mixture of SDS and TX-100 was determined to be 0.15 mM at a constant mole fraction (0.5) of both the surfactants as determined by the conductometry method. The determined CMC value of SDS/TX-100 mixture is higher than CMC of TX-100 (0.24 mM) and much lower than CMC of SDS (8.2 mM) (Table S2, Figure S8). 26 , 49 This study also suggests that discrete single micelle does not exist in the solution mixture rather mixed micelle was produced in the aqueous surfactant mixture (Scheme 2 ). Earlier works accounted the strong possibility for the interaction of alpha protons of SDS with the phenyl ring of substrate at the close proximity of the mixed micellar form, and the water repelling hydrophobic moiety of SDS is hardly stretched upto the micellar core unlike the coiled hydrophilic moiety of TX-100 in the same aggregation. The appreciable coupling of α-H’s, β-H’s and bulk- H’s of SDS with e-H’s and d-H’s of TX-100 respectively due to their closeness in mixed micelles is also reported earlier. 48 For a more illustrative analysis about the relative position of the surfactant molecules in the solution mixture, a 2D NOESY of the 1:1 surfactant mixture solution was recorded (Fig. 6 ). The peaks in the spectrum elucidates the appreciable coupling of α-H’s, β-H’s and bulk- H’s of SDS with d-H’s and e-H’s of TX-100 respectively due to their closeness in mixed micelles. The observed rate constant in presence of 1:1 SDS/TX-100 mixed micelle has been found to some extent lower than that observed rate constant in single SDS micelle and higher than that observed rate constant in TX-100 catalysed reaction (Table 1 ). In addition to that the increase in concentration of a surfactant keeping the other [surfactant] constant above CMC showed significant rate enhancement compared to that of single micelle catalysed reaction (Fig. 7 ). Noticeably, the kinetics of the reaction augmented further when concentration of TX-100 raised from 0.01 M to 0.05 M keeping [SDS] fixed at 0.01 M. This can be interpreted by considering the formation of micellar aggregation of TX-100 first followed by the decoration of SDS. 26 Again at low concentration of SDS, the penetrating space of the substrate inside the TX-100 micelle is occupied by the anionic surfactants and simultaneously a steric reason hinders the same path, reaction rate gets deteriorated. Now, on increasing surfactant concentration of any type corresponding single micellar aggregation may coexist with mixed micelle, which results in rate enhancement. 4.2.4 Micelle catalysed promoted path From Table 2 we have noticed that the order of reaction rate in promoted path is k obs (Phen) > k obs (Bpy). In micellar catalysed promoted path the mechanism of the reaction is same as that of promoted path. Here also the observed rate constants depend on how easily substrate reacts with active oxidant (AO + ) present in aqueous micellar medium to form chromate ester (Scheme S1 and S2). In presence of TX-100 micelle there exists π-π interaction in between the active oxidant species and aromatic sextet of TX-100 and such type of interaction enhances the congregation of active oxidants in stern layer of micelle leading to greater rate of reaction. 1, 10-phenanthroline contains higher number of π-electrons than Bpy, so it shows higher rate of oxidation than Bpy. Hence the rate constant follow the order k obs (Phen) > k obs (Bpy) in TX-100 medium (Table 2 ). In SDS micellar medium there is no π-π interaction between the active oxidant and SDS, but here strong attractive electrostatic attraction is present between negatively charged SDS and positively charged active oxidant. The active oxidant (AO+) formed by Phen and Bpy are both bipositive in nature. So, considering only attractive force between SDS and active oxidant, Phen and Bpy should show similar rate of oxidation ( k obs (Bpy) ≈ k obs (Phen)). In SDS medium besides attractive interaction there is also a possibility of repulsion between negative charge surface of SDS and π electron cloud of active oxidant (AO + ). In Phen π electron density is greater than Bpy. So the repulsive interaction is higher in Phen promoted path than Bpy promoted reaction path. So considering only repulsive interaction k obs (Bpy) should be greater than k obs (Phen). Considering both the attractive force and repulsive interaction simultaneously the real order of k obs in SDS micelle is k obs (Bpy) > k obs (Phen) (Table 2 ). In SDS/TX-100 mixed micelle catalysed path the observed rate constants is k obs (Bpy) > k obs (Phen) (Fig. 8 ), it can be explained considering above discussed factors and steric factor discussed in the mixed micelle catalysed path. Conclusion In this article a green approach of chromic acid directed oxidation kinetics of an aromatic alcohol in presence of single micelle and mixed micelle has been investigated. Combination of micellar catalyst with promoters completes the oxidation of aromatic alcohol almost instantly. In addition to (TX-100 + Phen) and (SDS + Bpy), (SDS + TX-100 + Bpy) were also found to be excellent catalyst. Utilisation of quite low cost mixed micelle may open a new opportunity and supposed to be advantageous for industry. 26 In future the effect of mixed micelle on oxidation of various aromatic alcohols and on some physiochemical properties study, for example shape and size of mixed micelle, may lead to some new findings. Besides, such type of kinetics study in variety of binary surfactant media (mixed micelle) like cationic-nonionic, anionic-anionic and cationic-cationic might be of enormous importance for scientific and industrial research. Declarations Acknowledgement We are thankful to IIT(ISM) Dhanbad for instrumental support. Consent to publish We have provided the consent to publish this work. Competing interests The authors declare no conflicts of interest regarding this article. Author contribution All the authors have accepted responsibility for the entire content of this manuscript and approved submission. AR and BS have designed this work. 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Supplementary Files SupplimentaryMaterial.docx Cite Share Download PDF Status: Published Journal Publication published 12 Jul, 2023 Read the published version in Research on Chemical Intermediates → Version 1 posted Editorial decision: Major revision 26 May, 2023 Reviews received at journal 25 May, 2023 Reviews received at journal 17 May, 2023 Reviewers agreed at journal 08 May, 2023 Reviewers invited by journal 08 May, 2023 Editor assigned by journal 27 Apr, 2023 Submission checks completed at journal 27 Apr, 2023 First submitted to journal 25 Apr, 2023 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-2861036","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":195833481,"identity":"3ca21049-ea35-4122-a8e1-3d6623487184","order_by":0,"name":"Atanu Rakshit","email":"","orcid":"","institution":"The University of Burdwan","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Atanu","middleName":"","lastName":"Rakshit","suffix":""},{"id":195833482,"identity":"7992b15c-89c9-49f6-a973-e43991dd6eb7","order_by":1,"name":"Suman Chowdhury","email":"","orcid":"","institution":"The University of Burdwan","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Suman","middleName":"","lastName":"Chowdhury","suffix":""},{"id":195833483,"identity":"8b665643-7044-4351-9477-fde2c154ef9c","order_by":2,"name":"Animesh Acharjee","email":"","orcid":"","institution":"The University of Burdwan","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Animesh","middleName":"","lastName":"Acharjee","suffix":""},{"id":195833484,"identity":"f82d3ee9-a492-49c3-8706-0b768b9ae1b2","order_by":3,"name":"Kalachand Mahali","email":"","orcid":"","institution":"University of Kalyani","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Kalachand","middleName":"","lastName":"Mahali","suffix":""},{"id":195833485,"identity":"0981d434-c920-4ee6-ad20-69ea5ef00092","order_by":4,"name":"Rumpa Saha","email":"","orcid":"","institution":"Charuchandra College","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Rumpa","middleName":"","lastName":"Saha","suffix":""},{"id":195833486,"identity":"c685c0b3-d513-4b00-a21f-6ddf46616b68","order_by":5,"name":"Pintu Sar","email":"","orcid":"","institution":"Indian Institute of Science Education and Research Kolkata","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Pintu","middleName":"","lastName":"Sar","suffix":""},{"id":195833487,"identity":"3e317369-207d-4e35-aa24-fc27dd77ba7d","order_by":6,"name":"Bidyut Saha","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA8UlEQVRIiWNgGAWjYBACAwYGNgaGCoYEBjADTjJIENByhmQtjG1IWggCc/7Dzx78nGeXxy92gO0x757DeXwSCYwffjBY5OHSYjkjzdywd1tyseTsBHZjnmeHi9kkEpglexgkinE67AaDmQTvtgOJG24nsEnzHDic2MZzgEEa6JfEBlxazh//Jvl3zoHE/UhamH/j1XIgx0yatwFoizRMC3sDG15bLGfklEnLHEtOnHE7sd1wzoF0oJbGNsseA9xazPmPb5N8U2OX2D87+diDNwesE+c3Mx++8aOiDqcWJMDYgMQwIKx+FIyCUTAKRgFuAABex1OsiszHSwAAAABJRU5ErkJggg==","orcid":"","institution":"The University of Burdwan","correspondingAuthor":true,"submittingAuthor":false,"prefix":"","firstName":"Bidyut","middleName":"","lastName":"Saha","suffix":""}],"badges":[],"createdAt":"2023-04-25 20:14:15","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-2861036/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-2861036/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1007/s11164-023-05061-z","type":"published","date":"2023-07-13T01:08:31+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":36540299,"identity":"ccf15880-60f2-40fd-9ce9-59db81438afa","added_by":"auto","created_at":"2023-05-02 19:35:49","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":110865,"visible":true,"origin":"","legend":"\u003cp\u003eSequential time dependent absorption spectra of the studied oxidation reaction in absence of surfactant and promoter at 30 ºC.\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/238669a3ed42e1c4234d0ecb.png"},{"id":36539689,"identity":"7dd174d6-14f3-452e-bb10-03329da02aa3","added_by":"auto","created_at":"2023-05-02 19:27:49","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":6213,"visible":true,"origin":"","legend":"\u003cp\u003eRepresentative -ln(Abs) \u003cem\u003evs\u003c/em\u003e time plot for the uncatalysed reaction at 30 °C.\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/a013d9c1f1357d257cc18dac.png"},{"id":36540301,"identity":"84caecda-3d72-4060-9de8-4b323bc5f986","added_by":"auto","created_at":"2023-05-02 19:35:49","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":50253,"visible":true,"origin":"","legend":"\u003cp\u003eHistogram of maximum \u003cem\u003e\u003cstrong\u003ek\u003c/strong\u003e\u003c/em\u003e\u003csub\u003e\u003cem\u003e\u003cstrong\u003eobs \u003c/strong\u003e\u003c/em\u003e\u003c/sub\u003evalues for different reaction sets.\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/e7e274d6f7a3c31263da8172.png"},{"id":36540447,"identity":"f3308a76-1caa-4bad-ac68-6a64934ed262","added_by":"auto","created_at":"2023-05-02 19:43:49","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":6656,"visible":true,"origin":"","legend":"\u003cp\u003eVariation of rate constant values (\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e)\u003csub\u003e\u003cem\u003e \u003c/em\u003e\u003c/sub\u003ewith [promoter]\u003csub\u003eT\u003c/sub\u003e in aqueous media at 30 °C.\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/456a7bb3f3af253b80a68fef.png"},{"id":36539686,"identity":"43e75832-29f0-4039-b585-07792e6baa64","added_by":"auto","created_at":"2023-05-02 19:27:49","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":6485,"visible":true,"origin":"","legend":"\u003cp\u003eDependence of \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e\u003csub\u003e\u003cem\u003e \u003c/em\u003e\u003c/sub\u003eof oxidation on [surfactant]\u003csub\u003eT\u003c/sub\u003e at 30 °C. Pink circle: TX-100 and Cyan triangle: SDS mediated oxidation reactions.\u003c/p\u003e","description":"","filename":"5.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/90506edd654a0afef7e0e73b.png"},{"id":36539691,"identity":"ea97b5df-72e8-4071-899e-d9b556a1dcdb","added_by":"auto","created_at":"2023-05-02 19:27:49","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":353165,"visible":true,"origin":"","legend":"\u003cp\u003e2D NOESY spectrum of 1:1 SDS/TX-100 mixed surfactant solution. [SDS]\u003csub\u003eT\u003c/sub\u003e = 0.01 mol dm\u003csup\u003e-3 \u003c/sup\u003e+ [TX 100]\u003csub\u003eT\u003c/sub\u003e = 0.01 mol dm\u003csup\u003e-3\u003c/sup\u003e\u003c/p\u003e","description":"","filename":"6.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/9414057a84508bd5b1ede733.png"},{"id":36539693,"identity":"14a9bfe2-de24-4dbc-9e00-aedcfba5b8ce","added_by":"auto","created_at":"2023-05-02 19:27:49","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":8633,"visible":true,"origin":"","legend":"\u003cp\u003ePlot of \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e\u003csub\u003e\u003cem\u003e \u003c/em\u003e\u003c/sub\u003e\u003cem\u003evs\u003c/em\u003e concentration of surfactants.\u003c/p\u003e","description":"","filename":"7.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/204a874c23cf44cfa5cb471b.png"},{"id":36540302,"identity":"ccb348bd-57b0-49a8-93e9-2dd71dc634da","added_by":"auto","created_at":"2023-05-02 19:35:49","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":6601,"visible":true,"origin":"","legend":"\u003cp\u003eDependence of \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e\u003csub\u003e\u003cem\u003e \u003c/em\u003e\u003c/sub\u003eof oxidation reaction on [promoter]\u003csub\u003eT \u003c/sub\u003ein presence of SDS/TX-100 mixed micelle at 30 °C. [SDS] = 10×10\u003csup\u003e-3 \u003c/sup\u003emol dm\u003csup\u003e-3\u003c/sup\u003e + [TX-100] = 10×10\u003csup\u003e-3 \u003c/sup\u003emol dm\u003csup\u003e-3\u003c/sup\u003e\u003c/p\u003e","description":"","filename":"8.png","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/796402a6d5da03bb7bfa8546.png"},{"id":41736942,"identity":"726745d7-d428-4caa-9de3-8c638af4c7fb","added_by":"auto","created_at":"2023-08-18 04:13:37","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":936536,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/31d2cd68-bf69-48b5-b9a0-13696a2912cc.pdf"},{"id":36539694,"identity":"704d0cd0-6655-4c94-a33d-545ece646365","added_by":"auto","created_at":"2023-05-02 19:27:49","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":374761,"visible":true,"origin":"","legend":"","description":"","filename":"SupplimentaryMaterial.docx","url":"https://assets-eu.researchsquare.com/files/rs-2861036/v1/7d40752bcf6f2c145f6e68ae.docx"}],"financialInterests":"No competing interests reported.","formattedTitle":"A synergistic combination of SDS and TX-100 for the catalytic oxidation of an aromatic alcohol in aqueous media","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eMicelles are generally simple spherical supramolecules, formed by amphiphiles in aqueous medium. Micellar system normally appears as macroscopically homogeneous due to the existence of colloidal size aggregates however in reality they are microheterogeneous system and function as nanoreactors for numerous organic reactions.\u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e Micelles can accelerate and/or inhibit a chemical reaction relative to the same reaction performed in an aqueous medium. At present aqueous micellar technology are used efficiently to perform many organic reactions in water and the recreation of various organic transformations in aqueous micellar medium has several advantages\u003csup\u003e\u003cspan additionalcitationids=\"CR3 CR4 CR5\" citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e\u003c/sup\u003e. The beauty of aqueous micellar media is that it is a green environment, can substitute the hazardous volatile organic solvents that are practically difficult to remove from the organic synthesis.\u003csup\u003e\u003cspan additionalcitationids=\"CR8 CR9 CR10\" citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e\u003c/sup\u003e Noticeably, exercise of mixed micelle in various purposes including emulsification, dispersion, detergency, targeted drug delivery \u003cem\u003eetc.\u003c/em\u003e\u003csup\u003e\u003cspan additionalcitationids=\"CR13 CR14 CR15 CR16 CR17\" citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e\u003c/sup\u003e instead of single one shows very significant performance due to the synergistic effect of constituent surfactants. In our recent works we have investigated the catalytic efficacy of mixed micellar media in oxidation of several organic substrates\u003csup\u003e\u003cspan additionalcitationids=\"CR20\" citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e21\u003c/span\u003e\u003c/sup\u003e along with the physiochemical properties of different mixed micellar composition by different techniques including conductivity, DLS (dynamic light scattering), spectrofluorimetry, \u003cem\u003eetc.\u003c/em\u003e\u003csup\u003e\u003cspan additionalcitationids=\"CR23 CR24 CR25\" citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e\u003c/sup\u003e In this report we have accounted the effect of anionic-nonionic mixed micelle on the oxidation kinetic of an aromatic alcohol using the transitional metal oxidant. In addition to, the aggregation behaviour of binary surfactant mixtures has been analyzed following the outcomes of 2D-NOESY.\u003c/p\u003e \u003cp\u003eChromium(VI) compounds has long been used as potential oxidant for oxidation of alcohols (aliphatic and aromatic) and aldehydes in water or organic medium and has been used for years.\u003csup\u003e\u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e27\u003c/span\u003e\u003c/sup\u003e Use of chromic acid as oxidising agent in aqueous medium is really interesting on account of its distinct aqueous chemistry in H\u003csub\u003e2\u003c/sub\u003eSO\u003csub\u003e4\u003c/sub\u003e medium and generation of reactive short-live intermediate species during the course of electron-transfer reaction. Noticed that Cr(III) is produced at the end of redox transformations, and some report about the usefulness of Cr(III)-picolinate as nutritional supplement encourages to introduce chromium metal as oxidizing agent. Previous works on chromic acid directed oxidation of many organic compounds suggests that, the oxidation rate was further influenced by utilising some \u003cem\u003eN\u003c/em\u003e-bases such as 1,10-Phenanthroline, 2,2'-Bipyridine, 2-Picolinic acid, \u003cem\u003eetc.\u003c/em\u003e\u003csup\u003e\u003cspan additionalcitationids=\"CR32 CR33 CR34 CR35\" citationid=\"CR31\" class=\"CitationRef\"\u003e31\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e36\u003c/span\u003e\u003c/sup\u003e which was materialized as Cr(III)-\u003cem\u003eN\u003c/em\u003e-base complexes at the end of oxidation. These heteroaromatic \u003cem\u003eN\u003c/em\u003e-bases compounds are better termed as promoter instead of catalyst.\u003csup\u003e\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e,\u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e36\u003c/span\u003e\u003c/sup\u003e\u003c/p\u003e \u003cp\u003eIn our recent work we have manifested the oxidation kinetic of 4-chlorobenzyl alcohol in single micellar medium following pseudo-first order condition.\u003csup\u003e\u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e\u003c/sup\u003e Herein, we have uncovered the role of SDS/TX-100 mixed micellar media on the oxidation of same aromatic alcohol by chromic acid at 30\u0026deg;C. The product, 4-chlorobenzaldehyde, is an important intermediate produced in pharmaceutical industry mainly.\u003csup\u003e\u003cspan additionalcitationids=\"CR38\" citationid=\"CR37\" class=\"CitationRef\"\u003e37\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e39\u003c/span\u003e\u003c/sup\u003e The functions of two promoters Bpy and Phen on the oxidation kinetic has been scrutinized in microheterogeneous media. The significant growth of reaction rate was observed when Bpy participated in oxidation mechanism and nanomicellar media (SDS and SDS/TX-100) accommodate the reactant species fructuously during the course of reaction.\u003c/p\u003e"},{"header":"2. Experimental","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e2.1. Materials\u003c/h2\u003e \u003cp\u003e4-Chlorobenzyl alcohol (\u0026gt;\u0026thinsp;98.0%, AR, Sigma-Aldrich, USA), Sulphuric acid [H\u003csub\u003e2\u003c/sub\u003eSO\u003csub\u003e4\u003c/sub\u003e] (\u0026gt;\u0026thinsp;97%, AR, Merck, India), potassium dichromate [K\u003csub\u003e2\u003c/sub\u003eCr\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003e] (\u0026gt;\u0026thinsp;99.0%, AR, BDH, India), Triton X-100 [TX-100] (98%, AR, HIMEDIA, Maharashtra, India), sodium dodecylsulfate (\u0026gt;\u0026thinsp;90%, AR, Merck, India), 1, 10-phenanthroline (\u0026gt;\u0026thinsp;99.0%, AR, Merck, India), 2, 2\u0026acute;-bipyridine (\u0026gt;\u0026thinsp;98%, AR, Spectrochem, Mumbai, India), chloroform-d (CDCl\u003csub\u003e3\u003c/sub\u003e) (\u0026gt;\u0026thinsp;99.0%, AR, Sigma-Aldrich, USA), deuterium oxide (D\u003csub\u003e2\u003c/sub\u003eO) (\u0026gt;\u0026thinsp;99.0%, AR, Sigma-Aldrich, USA) were used as received without further purification. All the aliquots were made using double distilled water (specific conductance 2.0 \u0026micro;S cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e2.2. Instrumentation\u003c/h2\u003e \u003cp\u003eTemperature controller attached UV-Vis-2450 (SHIMADZU) spectrophotometer was used to monitor the reaction kinetic. In preparing the reaction solutions sonicator, ultrasonic cleaner (CD 4820), and Sartorius BSA 224S-CW weighing balance were used. The Perkin Elmer Spectrum 2 and Bruker ASCEND 400 MHz spectrometers were used to record the FTIR and \u003csup\u003e1\u003c/sup\u003eH-NMR spectrum of the reaction product, respectively.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e2.3. Kinetics measurements\u003c/h2\u003e \u003cp\u003eThe oxidation reaction (in presence of surfactant and/or promoter ) has been performed maintaining the pseudo first order condition. For instance, the substrate (4-chlorobenzyl alcohol) concentration (40\u0026times;10\u003csup\u003e\u0026minus;\u0026thinsp;4\u003c/sup\u003e mol dm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e) in large excess (\u0026ge;\u0026thinsp;10-\u003cem\u003efold\u003c/em\u003e) relative to the Cr(VI) (4\u0026times;10\u003csup\u003e\u0026minus;\u0026thinsp;4\u003c/sup\u003e mol dm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e) has been taken in aqueous sulphuric acid (0.4 mol dm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e) medium at 30\u0026deg;C (\u0026plusmn;\u0026thinsp;0.1\u0026deg;C). The gradual decrease of absorbance of Cr(VI) with respect to regular time interval at λ\u003csub\u003emax\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;440 nm has been recorded with the UV-Vis spectrophotometer to show the progress of the reactions. The slope values of the plots of -ln(Abs)\u003csub\u003e440\u003c/sub\u003e\u003cem\u003evs\u003c/em\u003e time(t) were used to calculate the rate constant (\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e) values and t\u003csub\u003e1/2\u003c/sub\u003e values using the formula (ln2/\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section2\"\u003e \u003ch2\u003e2.4. Product analysis and stoichiometry\u003c/h2\u003e \u003cp\u003eIn case of uncatalyzed (without surfactant) and unpromoted (without promoter) reaction, the yellow-orange Cr(VI) solution turned into pale greenish-blue coloured solution (Cr(III)) ensured the completion of reaction. After extracting the reaction mixture using diethyl ether followed by evaporation of the solvent, the product was obtained mixed with a slight portion of unreacted solid substrate. Then the product was isolated from the impurity-like substrate by successive treatment with sodium bisulphite solution and solvent extraction.\u003csup\u003e\u003cspan citationid=\"CR40\" class=\"CitationRef\"\u003e40\u003c/span\u003e,\u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e41\u003c/span\u003e\u003c/sup\u003e The recrystallized product and its 2,4-DNP derivative, further recrystallized with ethanol, gave melting points 46\u0026deg;C and 265\u0026deg;C respectively conformed the corresponding carbonyl product. Spectroscopic analysis (IR and \u003csup\u003e1\u003c/sup\u003eH-NMR) also confirmed the product is 4-chlorobenzaldehyde.\u003c/p\u003e \u003cp\u003eSpectrophotometric titration of varying concentrations of substrate using Cr(VI) of known concentration in presence of 0.4 mol dm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e sulphuric acid gave the following reaction with stoichiometric coefficients. The absorbance values in all cases were taken at 580 nm after 48 hours to get steady measurements.\u003c/p\u003e\u003cp\u003e\u003cimg src=\"https://myfiles.space/user_files/122228_c8a1650c59388082/122228_custom_files/img1683051291.png\"\u003e\u003c/p\u003e\n\u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003e2.5. Precautions\u003c/h2\u003e \u003cp\u003eThe alarming toxicity and carcinogenicity of Cr(VI) has limited us the drainage of the same in the experiment. Excessive discharging of surfactants in water bodies also endanger the aquatic lives.\u003csup\u003e\u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e42\u003c/span\u003e,\u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e43\u003c/span\u003e\u003c/sup\u003e Hence, SDS and TX-100 were recycled and thereby eliminating from the product mixtures (after completion of reaction) through the precipitation with calcium salt and thermal precipitation respectively.\u003csup\u003e\u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e\u003c/sup\u003e\u003c/p\u003e \u003c/div\u003e"},{"header":"3. Results","content":"\u003cdiv id=\"Sec9\" class=\"Section2\"\u003e\n \u003ch2\u003e3.1. UV-Vis spectral analysis and kinetic outcomes\u003c/h2\u003e\n \u003cp\u003eThe successive drop in absorbance with respect to equal time interval, provided in Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e, showed the progress of reaction which was performed in absence of surfactant and promoters. The corresponding \u0026ndash;ln(Abs) \u003cem\u003evs\u003c/em\u003e time plot (Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e) for every kinetic run help to figure out overall kinetic profile, tabulated in Table \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and Table \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e. The rate constant (\u003cem\u003ek\u003c/em\u003e\u003csub\u003e\u003cem\u003eobs\u003c/em\u003e\u003c/sub\u003e) values along with respective half-life (t\u003csub\u003e1/2\u003c/sub\u003e) were registered in Table \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and Table \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e, in which Table \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e represents the single as well as binary surfactant mediated oxidation kinetics and Table \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e highlights the kinetic parameters for the reaction performed in presence of surfactants and promoters. The tables show that both the single micelles and the mixed micelle have the capability to amplify the reaction rate constant values that indicate the rate enhancement of oxidation process. Noticed, two promoters Phen and Bpy also accelerated the reaction rate. In addition to single micelles the binary mixture of surfactants in combination with promoters enhanced reaction rate significantly, as realized from the histogram (Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eUnder pseudo-first order condition in presence of large excess of substrate, Cr(VI) ions could surely be reduced to Cr(III) as the reaction proceed. The formation of Cr(III) pale blue coloured solution, was confirmed by the appearance of absorption maxima at 580 nm and 403 nm. (Figure \u003cspan class=\"InternalRef\"\u003eS1\u003c/span\u003e). Again, after the completion of the reaction the pale violet colour was observed in presence of Bpy having \u0026lambda;\u003csub\u003emax\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;547 nm and pale pink colour was noticed for phen governed oxidation (\u0026lambda;\u003csub\u003emax\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;550 nm) towards (Figure \u003cspan class=\"InternalRef\"\u003eS1\u003c/span\u003e). Actually, in absence of promoter final reduced product is aqua-Cr(III) species but in presence of promoters, Cr(III)-promoter complex were generated as the reduced species (Figure \u003cspan class=\"InternalRef\"\u003eS1\u003c/span\u003e).\u003csup\u003e\u003cspan class=\"CitationRef\"\u003e45\u003c/span\u003e,\u003cspan class=\"CitationRef\"\u003e46\u003c/span\u003e\u003c/sup\u003e Under the experimental condition the single isosbestic point in the UV-Vis spectrum of each reaction suggests the possibility of generation of Cr(IV) and Cr(V) like intermediates with very low concentration (Figure S2).\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003eTable 1.\u0026nbsp;\u003c/strong\u003eRate constant (\u003cem\u003ek\u003csub\u003eobs\u003c/sub\u003e\u003c/em\u003e) and half life (\u003cem\u003et\u003c/em\u003e\u003csub\u003e1/2\u003c/sub\u003e) of oxidation reaction in presence of SDS, TX-100 and SDS/TX-100 mixed micelle.\u003c/p\u003e\n \u003cdiv\u003e\n \u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"56.33116883116883%\" colspan=\"2\" valign=\"top\" style=\"width: 59.9969%;\"\u003e\n \u003cp\u003e\u003cstrong\u003e10\u003csup\u003e3\u003c/sup\u003e\u0026times;Micellar catalyst [mol dm\u003csup\u003e-3\u003c/sup\u003e]\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.5974025974026%\" rowspan=\"2\" valign=\"top\" style=\"width: 20.8203%;\"\u003e\n \u003cp\u003e\u003cstrong\u003e10\u003csup\u003e4\u0026nbsp;\u003c/sup\u003e\u0026times; \u003cem\u003ek\u003csub\u003eobs\u003c/sub\u003e\u003c/em\u003e[s\u003csup\u003e-1\u003c/sup\u003e]\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.071428571428573%\" rowspan=\"2\" valign=\"top\" style=\"width: 18.4788%;\"\u003e\n \u003cp\u003e\u003cstrong\u003et\u003csub\u003e1/2\u0026nbsp;\u003c/sub\u003e[min]\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"48.275862068965516%\" valign=\"top\" style=\"width: 35.547%;\"\u003e\n \u003cp\u003e\u003cstrong\u003eSDS\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"51.724137931034484%\" valign=\"top\" style=\"width: 25.6545%;\"\u003e\n \u003cp\u003e\u003cstrong\u003eTX-100\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"27.228525121555915%\" valign=\"top\" style=\"width: 35.547%;\"\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"29.173419773095624%\" valign=\"top\" style=\"width: 25.6545%;\"\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.55267423014587%\" valign=\"top\" style=\"width: 20.8203%;\"\u003e\n \u003cp\u003e0.48 \u0026plusmn; 0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.045380875202593%\" valign=\"top\" style=\"width: 18.4788%;\"\u003e\n \u003cp\u003e240.62\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"27.228525121555915%\" valign=\"top\" style=\"width: 35.547%;\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"29.173419773095624%\" valign=\"top\" style=\"width: 25.6545%;\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.55267423014587%\" valign=\"top\" style=\"width: 20.8203%;\"\u003e\n \u003cp\u003e1.85 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e2.52 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e3.07 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e3.51 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e3.92 \u0026plusmn; 0.02\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.045380875202593%\" valign=\"top\" style=\"width: 18.4788%;\"\u003e\n \u003cp\u003e62.43\u003c/p\u003e\n \u003cp\u003e45.83\u003c/p\u003e\n \u003cp\u003e37.62\u003c/p\u003e\n \u003cp\u003e32.90\u003c/p\u003e\n \u003cp\u003e29.46\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"27.228525121555915%\" valign=\"top\" style=\"width: 35.547%;\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"29.173419773095624%\" valign=\"top\" style=\"width: 25.6545%;\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.55267423014587%\" valign=\"top\" style=\"width: 20.8203%;\"\u003e\n \u003cp\u003e1.14 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e1.36 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e1.58 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e1.81 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e2.02 \u0026plusmn; 0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.045380875202593%\" valign=\"top\" style=\"width: 18.4788%;\"\u003e\n \u003cp\u003e101.31\u003c/p\u003e\n \u003cp\u003e84.92\u003c/p\u003e\n \u003cp\u003e73.10\u003c/p\u003e\n \u003cp\u003e63.81\u003c/p\u003e\n \u003cp\u003e57.17\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"27.228525121555915%\" valign=\"top\" style=\"width: 35.547%;\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"29.173419773095624%\" valign=\"top\" style=\"width: 25.6545%;\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.55267423014587%\" valign=\"top\" style=\"width: 20.8203%;\"\u003e\n \u003cp\u003e1.70 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e2.20 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e2.62 \u0026plusmn; 0.02\u003c/p\u003e\n \u003cp\u003e2.99 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e3.38 \u0026plusmn; 0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.045380875202593%\" valign=\"top\" style=\"width: 18.4788%;\"\u003e\n \u003cp\u003e67.94\u003c/p\u003e\n \u003cp\u003e52.50\u003c/p\u003e\n \u003cp\u003e44.08\u003c/p\u003e\n \u003cp\u003e38.63\u003c/p\u003e\n \u003cp\u003e34.17\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"27.228525121555915%\" valign=\"top\" style=\"width: 35.547%;\"\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"29.173419773095624%\" valign=\"top\" style=\"width: 25.6545%;\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.55267423014587%\" valign=\"top\" style=\"width: 20.8203%;\"\u003e\n \u003cp\u003e2.83 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e3.79 \u0026plusmn; 0.01\u003c/p\u003e\n \u003cp\u003e4.41 \u0026plusmn; 0.02\u003c/p\u003e\n \u003cp\u003e4.93 \u0026plusmn; 0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.045380875202593%\" valign=\"top\" style=\"width: 18.4788%;\"\u003e\n \u003cp\u003e40.81\u003c/p\u003e\n \u003cp\u003e30.47\u003c/p\u003e\n \u003cp\u003e26.19\u003c/p\u003e\n \u003cp\u003e23.42\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cdiv class=\"gridtable\"\u003e\n \u003cdiv align=\"left\" class=\"colspec\"\u003e\u003cbr\u003e\u003c/div\u003e\n \u003c/div\u003e\n \u003cdiv class=\"gridtable\"\u003e\n \u003cdiv align=\"left\" class=\"colspec\"\u003e\u003cbr\u003e\u003c/div\u003e\u0026nbsp;\u003ctable id=\"Tab2\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eRate constant (\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e) and half life (t\u003csub\u003e1/2\u003c/sub\u003e) of oxidation reaction in presence of promoter mediated by aqueous SDS, TX-100, and SDS/TX-100 mixed micelle.\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e10\u003csup\u003e3\u003c/sup\u003e \u0026times; [SDS]\u003c/p\u003e\n \u003cp\u003emol dm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e10\u003csup\u003e3\u003c/sup\u003e \u0026times; [TX-100]\u003c/p\u003e\n \u003cp\u003emol dm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003ePromoter\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e10\u003csup\u003e4\u003c/sup\u003e \u0026times; [Promoter]\u003c/p\u003e\n \u003cp\u003emol dm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e10\u003csup\u003e4\u003c/sup\u003e\u0026times; \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e [s\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e]\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003et\u003csub\u003e1/2\u003c/sub\u003e[min]\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePhen\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.01\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e2.03\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e2.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e4.05\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e4.94\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e114.35\u003c/p\u003e\n \u003cp\u003e56.89\u003c/p\u003e\n \u003cp\u003e38.76\u003c/p\u003e\n \u003cp\u003e28.52\u003c/p\u003e\n \u003cp\u003e23.38\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBpy\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.84\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e1.54\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03\u003c/p\u003e\n \u003cp\u003e2.22\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e2.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e3.72\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e137.50\u003c/p\u003e\n \u003cp\u003e75.00\u003c/p\u003e\n \u003cp\u003e52.03\u003c/p\u003e\n \u003cp\u003e38.76\u003c/p\u003e\n \u003cp\u003e31.05\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePhen\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.22\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e4.32\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03\u003c/p\u003e\n \u003cp\u003e5.87\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e9.34\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e11.74\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e52.02\u003c/p\u003e\n \u003cp\u003e26.73\u003c/p\u003e\n \u003cp\u003e19.67\u003c/p\u003e\n \u003cp\u003e12.36\u003c/p\u003e\n \u003cp\u003e9.83\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBpy\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e23.72\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e44.62\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e79.55\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e106.70\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03\u003c/p\u003e\n \u003cp\u003e146.50\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.86\u003c/p\u003e\n \u003cp\u003e2.58\u003c/p\u003e\n \u003cp\u003e1.45\u003c/p\u003e\n \u003cp\u003e1.08\u003c/p\u003e\n \u003cp\u003e0.79\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003eNone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePhen\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.53\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e3.92\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e5.35\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e8.52\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e12.68\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e75.49\u003c/p\u003e\n \u003cp\u003e29.46\u003c/p\u003e\n \u003cp\u003e21.59\u003c/p\u003e\n \u003cp\u003e13.55\u003c/p\u003e\n \u003cp\u003e9.10\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBpy\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.42\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e3.42\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e4.87\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e7.86\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e11.58\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e81.33\u003c/p\u003e\n \u003cp\u003e33.77\u003c/p\u003e\n \u003cp\u003e23.71\u003c/p\u003e\n \u003cp\u003e14.69\u003c/p\u003e\n \u003cp\u003e9.97\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" rowspan=\"2\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePhen\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e4.86\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e6.65\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e9.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e12.44\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e46.57\u003c/p\u003e\n \u003cp\u003e23.76\u003c/p\u003e\n \u003cp\u003e17.36\u003c/p\u003e\n \u003cp\u003e11.57\u003c/p\u003e\n \u003cp\u003e9.28\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBpy\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e22.99\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01\u003c/p\u003e\n \u003cp\u003e44.32\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e78.97\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03\u003c/p\u003e\n \u003cp\u003e105.72\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003cp\u003e144.16\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.02\u003c/p\u003e\n \u003cp\u003e2.60\u003c/p\u003e\n \u003cp\u003e1.46\u003c/p\u003e\n \u003cp\u003e1.09\u003c/p\u003e\n \u003cp\u003e0.80\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n\n\u003c/div\u003e"},{"header":"4. Discussion","content":"\u003cdiv id=\"Sec11\" class=\"Section2\"\u003e \u003ch2\u003e4.1. Product analysis\u003c/h2\u003e \u003cp\u003eThe IR spectrum of the separated product exhibits stretching frequency at 1688.39 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e corresponding to the C\u0026thinsp;=\u0026thinsp;O bond of aromatic aldehyde group (Figure S3) and the recrystallized 2, 4-DNP derivative of the product displays stretching frequency at 1615 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 3285 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e pertaining to C\u0026thinsp;=\u0026thinsp;N and N\u0026ndash;H bonds, respectively (Figure S4).\u003c/p\u003e \u003cp\u003eThe \u003csup\u003e1\u003c/sup\u003eH-NMR spectrum (Figure S5) of the product (carried out in CDCl\u003csub\u003e3\u003c/sub\u003e solvent) shows a singlet peak with chemical shift value at 9.9 ppm confirms the aldehydic proton. The peaks near 8 and 7.5 ppm in the spectrum indicate two different type of protons, one is ortho to \u0026ndash;CHO and another is ortho to \u0026ndash;Cl group (Table \u003cspan refid=\"MOESM1\" class=\"InternalRef\"\u003eS1\u003c/span\u003e). The comprehensive analysis of FTIR and \u003csup\u003e1\u003c/sup\u003eH NMR spectra confirmed the oxidized product which is 4-chlorobenzaldehyde.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec12\" class=\"Section2\"\u003e \u003ch2\u003e4.2. Mechanism of the reaction\u003c/h2\u003e \u003cp\u003eThe mechanistic pathways of the oxidation can be classified into four different types (i) uncatalysed and unpromoted path, (ii) promoted path, (iii) micellar catalysed path and (iv) micellar catalysed promoted path.\u003c/p\u003e \u003cdiv id=\"Sec13\" class=\"Section3\"\u003e \u003ch2\u003e4.2.1. Uncatalysed and unpromoted path\u003c/h2\u003e \u003cp\u003eThe plausible mechanism of the uncatalysed and unpromoted reaction is already proposed in the previous work.\u003csup\u003e\u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e\u003c/sup\u003e Basically, the first step is the formation of neutral chromate ester species between the substrate and chromic acid (H\u003csub\u003e2\u003c/sub\u003eCrO\u003csub\u003e4\u003c/sub\u003e). The neutral ester species was then decomposed as governed by H\u003csup\u003e+\u003c/sup\u003e ion, this is the r/d step, to give the actual oxidized product and Cr(III) species.\u003csup\u003e\u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e47\u003c/span\u003e\u003c/sup\u003e This is simple mechanistic pathway for the chromic acid directed oxidative transformation of 4-chlorobenzyl alcohol to 4-chlorobenzaldehyde in aqueous media only. It would be interesting to highlight on the reaction kinetic which was affected by micellar media in presence of promoter significantly.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec14\" class=\"Section3\"\u003e \u003ch2\u003e4.2.2 Promoted path\u003c/h2\u003e \u003cp\u003eThe reaction proceeds with much faster in presence of heteroaromatic \u003cem\u003eN\u003c/em\u003e-bases: Phen and Bpy, than the unpromoted one (Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). The rate constant values in presence of Phen and Bpy vary in the order \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Phen)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Bpy) (Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e). As already reported that in promoted path the case is quite different due to the formation of Cr(VI)-promoter complexes primarily, which gets reduced to Cr(III)-promoter complexes later. The Cr(VI)-promoter complexes are actual oxidants, recognized as active oxidant species (AO\u003csup\u003e+\u003c/sup\u003e) (Figure S6).\u003csup\u003e\u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e\u003c/sup\u003e\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThe generated active oxidant (AO\u003csup\u003e+\u003c/sup\u003e) species then undergoes acid catalysed decomposition to form the product. The observed rate constant variation with two promoters can be explained on account of the generation of stable active oxidants (AO\u003csup\u003e+\u003c/sup\u003e). Herein two promoters (Phen and Bpy) are acts as chelating agents, having two nitrogen donor sites, and fabricates the stable chelated complexes with Cr(VI) centre. The donor sites in 1, 10-Phenanthroline remain in \u003cem\u003ecis\u003c/em\u003e configuration with three stable aromatic rings, so rate of formation of active oxidant (AO\u003csup\u003e+\u003c/sup\u003e) is higher compare to the active oxidant species generated by 2, 2\u0026prime;-Bipyridine. Actually, in stable conformation the \u003cem\u003eN\u003c/em\u003e-donor sites of Bpy remains in trans orientation mutually and therefore in order to get converted into s-cis conformation an activation energy barrier must be overcome to formulate such chelated complex or so called active oxidant species. This phenomenon explains the cause of greater rate in case of Phen (Scheme S1 and Scheme S2).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec15\" class=\"Section3\"\u003e \u003ch2\u003e4.2.3 Micellar catalysed path\u003c/h2\u003e \u003cp\u003eIn presence of two surfactants SDS and TX-100 and in SDS/TX-100 mixed micellar medium the oxidation kinetics were amplified compared to the reaction performed in aqueous medium only (Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e). Micellar catalysed unpromoted path can be classified into (i) single micelle catalysed and (ii) mixed micelle catalysed path.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cdiv id=\"Sec16\" class=\"Section4\"\u003e \u003ch2\u003e4.2.3.1 Single micelle catalysed path\u003c/h2\u003e \u003cp\u003eIn single micelle catalysed path, both SDS and TX-100 enhance the rate of oxidation and the observed order of rate constant is \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(SDS)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(TX-100) (Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e) (Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e). In presence of anionic and nonionic micelle, the schematic representation of interaction between reactant molecules with micelle like surfactant aggregates is shown in Figure S7. In aqueous medium chromic acid is present as HCrO\u003csub\u003e4\u003c/sub\u003e\u003csup\u003e\u0026minus;\u003c/sup\u003e, but in micellar media protonation of HCrO\u003csub\u003e4\u003c/sub\u003e\u003csup\u003e\u0026minus;\u003c/sup\u003e occurs and neutral H\u003csub\u003e2\u003c/sub\u003eCrO\u003csub\u003e4\u003c/sub\u003e forms, this neutral species can bind with anionic and neutral surfactants through ion\u0026ndash;dipole interaction and H-bonding interaction at the stern layer of micellar surface and the reaction proceeds smoothly.\u003csup\u003e\u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e47\u003c/span\u003e\u003c/sup\u003e In micellar media (SDS and TX-100), the hydrophobic part of aromatic alcohol remains in the palisade layer and the polar hydrophilic part remains oriented toward the stern layer of micelle and thereby assists the solubilisation of substrate in aqueous micelle medium.\u003csup\u003e\u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e\u003c/sup\u003e In general, aromatic alcohol oxidation depends on two main steps. As mentioned earlier that the formation of neutral chromate ester and subsequent proton (H\u003csup\u003e+\u003c/sup\u003e) catalysed decomposition of the same in the r/d step take places in aqueous media only (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e). In anionic SDS micelle, on account of the strong attractive force, the H\u003csup\u003e+\u003c/sup\u003e ions can move towards the chromate ester faster than in neutral TX-100 micellar system, results further expediting the oxidation kinetics. Though, the moderate rate enhancement in TX-100 may be attributed to the togetherness of the neutral Cr(VI) species with the micellar aggregates by some supramolecular interaction (ion\u0026ndash;dipole interaction and H-bonding).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec17\" class=\"Section4\"\u003e \u003ch2\u003e4.2.3.2 Mixed micelle catalysed path\u003c/h2\u003e \u003cp\u003eAbove their individual CMC, TX-100 in combination with SDS shows a different λ\u003csub\u003emax\u003c/sub\u003e (hypochromic shift) from that of TX-100 only indicating a possibility of mixed micelle formation.\u003csup\u003e\u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e\u003c/sup\u003e The CMC of mixture of SDS and TX-100 was determined to be 0.15 mM at a constant mole fraction (0.5) of both the surfactants as determined by the conductometry method. The determined CMC value of SDS/TX-100 mixture is higher than CMC of TX-100 (0.24 mM) and much lower than CMC of SDS (8.2 mM) (Table S2, Figure S8).\u003csup\u003e\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e,\u003cspan citationid=\"CR49\" class=\"CitationRef\"\u003e49\u003c/span\u003e\u003c/sup\u003e This study also suggests that discrete single micelle does not exist in the solution mixture rather mixed micelle was produced in the aqueous surfactant mixture (Scheme \u003cspan refid=\"Sch2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). Earlier works accounted the strong possibility for the interaction of alpha protons of SDS with the phenyl ring of substrate at the close proximity of the mixed micellar form, and the water repelling hydrophobic moiety of SDS is hardly stretched upto the micellar core unlike the coiled hydrophilic moiety of TX-100 in the same aggregation. The appreciable coupling of α-H\u0026rsquo;s, β-H\u0026rsquo;s and bulk- H\u0026rsquo;s of SDS with e-H\u0026rsquo;s and d-H\u0026rsquo;s of TX-100 respectively due to their closeness in mixed micelles is also reported earlier.\u003csup\u003e\u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e\u003c/sup\u003e For a more illustrative analysis about the relative position of the surfactant molecules in the solution mixture, a 2D NOESY of the 1:1 surfactant mixture solution was recorded (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003e). The peaks in the spectrum elucidates the appreciable coupling of α-H\u0026rsquo;s, β-H\u0026rsquo;s and bulk- H\u0026rsquo;s of SDS with d-H\u0026rsquo;s and e-H\u0026rsquo;s of TX-100 respectively due to their closeness in mixed micelles.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThe observed rate constant in presence of 1:1 SDS/TX-100 mixed micelle has been found to some extent lower than that observed rate constant in single SDS micelle and higher than that observed rate constant in TX-100 catalysed reaction (Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e). In addition to that the increase in concentration of a surfactant keeping the other [surfactant] constant above CMC showed significant rate enhancement compared to that of single micelle catalysed reaction (Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003e). Noticeably, the kinetics of the reaction augmented further when concentration of TX-100 raised from 0.01 M to 0.05 M keeping [SDS] fixed at 0.01 M. This can be interpreted by considering the formation of micellar aggregation of TX-100 first followed by the decoration of SDS.\u003csup\u003e\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e\u003c/sup\u003e Again at low concentration of SDS, the penetrating space of the substrate inside the TX-100 micelle is occupied by the anionic surfactants and simultaneously a steric reason hinders the same path, reaction rate gets deteriorated. Now, on increasing surfactant concentration of any type corresponding single micellar aggregation may coexist with mixed micelle, which results in rate enhancement.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003c/div\u003e \u003cdiv id=\"Sec18\" class=\"Section3\"\u003e \u003ch2\u003e4.2.4 Micelle catalysed promoted path\u003c/h2\u003e \u003cp\u003eFrom Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e we have noticed that the order of reaction rate in promoted path is \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Phen)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Bpy). In micellar catalysed promoted path the mechanism of the reaction is same as that of promoted path. Here also the observed rate constants depend on how easily substrate reacts with active oxidant (AO\u003csup\u003e+\u003c/sup\u003e) present in aqueous micellar medium to form chromate ester (Scheme S1 and S2). In presence of TX-100 micelle there exists π-π interaction in between the active oxidant species and aromatic sextet of TX-100 and such type of interaction enhances the congregation of active oxidants in stern layer of micelle leading to greater rate of reaction. 1, 10-phenanthroline contains higher number of π-electrons than Bpy, so it shows higher rate of oxidation than Bpy. Hence the rate constant follow the order \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Phen)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Bpy) in TX-100 medium (Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). In SDS micellar medium there is no π-π interaction between the active oxidant and SDS, but here strong attractive electrostatic attraction is present between negatively charged SDS and positively charged active oxidant. The active oxidant (AO+) formed by Phen and Bpy are both bipositive in nature. So, considering only attractive force between SDS and active oxidant, Phen and Bpy should show similar rate of oxidation (\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Bpy)\u0026thinsp;\u0026asymp;\u0026thinsp;\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Phen)). In SDS medium besides attractive interaction there is also a possibility of repulsion between negative charge surface of SDS and π electron cloud of active oxidant (AO\u003csup\u003e+\u003c/sup\u003e). In Phen π electron density is greater than Bpy. So the repulsive interaction is higher in Phen promoted path than Bpy promoted reaction path. So considering only repulsive interaction \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Bpy) should be greater than \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Phen). Considering both the attractive force and repulsive interaction simultaneously the real order of \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e in SDS micelle is \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Bpy)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Phen) (Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). In SDS/TX-100 mixed micelle catalysed path the observed rate constants is \u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Bpy)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cem\u003ek\u003c/em\u003e\u003csub\u003eobs\u003c/sub\u003e(Phen) (Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003e), it can be explained considering above discussed factors and steric factor discussed in the mixed micelle catalysed path.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003c/div\u003e"},{"header":"Conclusion","content":"\u003cp\u003eIn this article a green approach of chromic acid directed oxidation kinetics of an aromatic alcohol in presence of single micelle and mixed micelle has been investigated. Combination of micellar catalyst with promoters completes the oxidation of aromatic alcohol almost instantly. In addition to (TX-100\u0026thinsp;+\u0026thinsp;Phen) and (SDS\u0026thinsp;+\u0026thinsp;Bpy), (SDS\u0026thinsp;+\u0026thinsp;TX-100\u0026thinsp;+\u0026thinsp;Bpy) were also found to be excellent catalyst. Utilisation of quite low cost mixed micelle may open a new opportunity and supposed to be advantageous for industry.\u003csup\u003e\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e\u003c/sup\u003e In future the effect of mixed micelle on oxidation of various aromatic alcohols and on some physiochemical properties study, for example shape and size of mixed micelle, may lead to some new findings. Besides, such type of kinetics study in variety of binary surfactant media (mixed micelle) like cationic-nonionic, anionic-anionic and cationic-cationic might be of enormous importance for scientific and industrial research.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAcknowledgement\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eWe are thankful to IIT(ISM) Dhanbad for instrumental support.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConsent to publish\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eWe have provided the consent to publish this work.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eCompeting interests\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare no conflicts of interest regarding this article.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthor contribution\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAll the authors have accepted responsibility for the entire content of this manuscript and approved submission. AR and BS have designed this work. SC and AA assisted AR to carry out experimental work. KM provided NMR facility. AR and BS wrote the manuscript. RS, BS, and PS modified and revised the whole manuscript.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThere is no funding to mention for this work.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAvailability of data and materials\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eData of this research work are available on request.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eT. Dwars, E. Paetzold and G. Oehme, Angew. \u003cem\u003eChem. Int. Ed.,\u003c/em\u003e 2005, \u003cstrong\u003e44\u003c/strong\u003e, 7174-7199.\u003c/li\u003e\n\u003cli\u003eH. Morawetz, \u003cem\u003eAdv. Catal.,\u003c/em\u003e 1969, \u003cstrong\u003e20\u003c/strong\u003e, 341-371.\u003c/li\u003e\n\u003cli\u003eF. Rosati, J. Oelerich and G. Roelfes, \u003cem\u003eChem. 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Sci.,\u003c/em\u003e 2013, \u003cstrong\u003e99\u003c/strong\u003e, 23-27.\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"research-on-chemical-intermediates","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"rint","sideBox":"Learn more about [Research on Chemical Intermediates](http://link.springer.com/journal/11164)","snPcode":"11164","submissionUrl":"https://submission.nature.com/new-submission/11164/3","title":"Research on Chemical Intermediates","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Aromatic alcohol, Oxidation, Nanomicellar catalysis, SDS/TX-100 mixed micelle, CMC lowering ","lastPublishedDoi":"10.21203/rs.3.rs-2861036/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-2861036/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eIn aqueous medium, oxidation of an aromatic alcohol (4-chlorobenzyl alcohol) was carried out in aqueous mixed micellar media under pseudo first order condition by chromic acid at 30 \u0026ordm;C. The micellar microenvironment constituted by anionic SDS and nonionic TX-100 surfactants showed excellent catalytic performance in course of oxidation, individually. In addition to that the nanomicelle produced by combination of SDS and TX-100 was found to be effective microheterogeneous catalyst for the aforementioned oxidation process. Use of two organic precursors, Phen and Bpy, entitled as promoter, made the reaction faster in presence of single micelle and mixed micelle. The fabrication of mixed micelle was confirmed by UV, \u003csup\u003e1\u003c/sup\u003eH-NMR and 2D NOESY study. The maximum improvement in reaction kinetic was noticed when SDS/TX-100 surfactants mixture introduced along with Bpy promoter.\u003c/p\u003e","manuscriptTitle":"A synergistic combination of SDS and TX-100 for the catalytic oxidation of an aromatic alcohol in aqueous media","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2023-05-02 19:27:44","doi":"10.21203/rs.3.rs-2861036/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Major revision","date":"2023-05-27T02:34:04+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2023-05-25T19:09:40+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2023-05-17T06:40:18+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"5dd2c882-f9d6-4802-a275-43cbc9abe186","date":"2023-05-08T06:10:38+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2023-05-08T05:44:46+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2023-04-28T02:45:41+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2023-04-28T02:45:40+00:00","index":"","fulltext":""},{"type":"submitted","content":"Research on Chemical Intermediates","date":"2023-04-25T20:05:25+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"research-on-chemical-intermediates","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"rint","sideBox":"Learn more about [Research on Chemical Intermediates](http://link.springer.com/journal/11164)","snPcode":"11164","submissionUrl":"https://submission.nature.com/new-submission/11164/3","title":"Research on Chemical Intermediates","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"22416543-c3b3-4fd6-970b-377798176a08","owner":[],"postedDate":"May 2nd, 2023","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2023-08-18T04:06:08+00:00","versionOfRecord":{"articleIdentity":"rs-2861036","link":"https://doi.org/10.1007/s11164-023-05061-z","journal":{"identity":"research-on-chemical-intermediates","isVorOnly":false,"title":"Research on Chemical Intermediates"},"publishedOn":"2023-07-13 01:08:31","publishedOnDateReadable":"July 13th, 2023"},"versionCreatedAt":"2023-05-02 19:27:44","video":"","vorDoi":"10.1007/s11164-023-05061-z","vorDoiUrl":"https://doi.org/10.1007/s11164-023-05061-z","workflowStages":[]},"version":"v1","identity":"rs-2861036","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-2861036","identity":"rs-2861036","version":["v1"]},"buildId":"7rjqhiLT3MXkJMwkYKINL","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}