Synthesis a New Family Hybrid Anionic / Nonionic Surfactant and Investigation their Physical Properties in relation to Chemical Enhanced Oil Recovery

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The paper synthesized a new family of hybrid anionic/nonionic surfactants by reacting maleic anhydride with 1-octene to form 2-octenyl succinic anhydride, esterifying it with ethoxylated alcohols (20 ethylene oxide units) to create nonionic surfactants (NMAE-10/12/14), then sulfonating them to form anionic analogs (AMAES-10/12/14). Surfactant structures were verified by infrared spectroscopy and 1H NMR, and at 50°C physical/thermodynamic properties were assessed using interfacial and surface tension measurements to derive parameters including ACN and nmin, as well as work of adhesion, spreading coefficient, and surface charge energy from additional contact angle data. Using a sand back model, the authors evaluated crude oil recovery, reporting that AMAES-12 had the lowest interfacial tension (0.01 mN/m) and reduced surface tension (16.3 mN/m), and achieved the highest total oil recovery of 92.3% of OOIP. The paper does not explicitly state limitations in the provided text beyond being a preprint prior to journal peer review. The paper does not explicitly discuss endometriosis or adenomyosis; it was included in the corpus via a keyword match in the upstream search index.

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Abstract

Abstract This study details the synthesis of a new class family of surfactants with dual anionic and nonionic moieties. The maleic anhydride reacted with 1-octene to prepare the corresponding 2-octenyl succinic anhydride. Then, this anhydride was esterified with prepared ethoxylated alcohols (ethylene oxide = 20 units) having different alkyl chains to obtain nonionic moiety surfactants named as; NMAE-10, NMAE-12 and NMAE-14. The sulfonation was carried for the nonionic surfactant by using sodium bisulfite to get three anionic moiety surfactants designated as; AMAES-10, AMAES-12 and AMAES-14. Infrared spectroscopy and ¹H NMR confirmed the surfactants' structures. At 50°C, Alkane carbon number (ACN) and n min were calculated by comparing n-hydrocarbon scans from n-C 6 to n-C 16 with the interfacial tension at the CMC. The work adhesion (W a ), spreading coefficient and surface charge energy for these surfactants were determined from interfacial tension, surface tension and contact angle measurements. A sand back model was utilized to examine the crude oil recovery factor at 50 °C. The obtained results indicated that, these surfactants have excellent performance in the term of surface activity and thermodynamics properties. Notably, AMAES-12 exhibits the most significant reduction in surface tension (16.3 mN/m) and the lowest interfacial tension (0.01 mN/m) at 50 ⁰C. The contact angle data demonstrated that, the prepared surfactants have efficiency to make alteration in wettability. The AMAES-12 achieved the maximum total oil recovery arrived 92.3% of the original from oil in place (OOIP).
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Synthesis a New Family Hybrid Anionic / Nonionic Surfactant and Investigation their Physical Properties in relation to Chemical Enhanced Oil Recovery | 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 Article Synthesis a New Family Hybrid Anionic / Nonionic Surfactant and Investigation their Physical Properties in relation to Chemical Enhanced Oil Recovery Ahmed M. Al-Sabagh, Eman Abdolrasheid, Notaila M. Nasser, Abeer M. El-Naggar, and 3 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7685730/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 29 Dec, 2025 Read the published version in Scientific Reports → Version 1 posted 10 You are reading this latest preprint version Abstract This study details the synthesis of a new class family of surfactants with dual anionic and nonionic moieties. The maleic anhydride reacted with 1-octene to prepare the corresponding 2-octenyl succinic anhydride. Then, this anhydride was esterified with prepared ethoxylated alcohols (ethylene oxide = 20 units) having different alkyl chains to obtain nonionic moiety surfactants named as; NMAE-10, NMAE-12 and NMAE-14. The sulfonation was carried for the nonionic surfactant by using sodium bisulfite to get three anionic moiety surfactants designated as; AMAES-10, AMAES-12 and AMAES-14. Infrared spectroscopy and ¹H NMR confirmed the surfactants' structures. At 50°C, Alkane carbon number (ACN) and n min were calculated by comparing n-hydrocarbon scans from n-C 6 to n-C 16 with the interfacial tension at the CMC. The work adhesion (W a ), spreading coefficient and surface charge energy for these surfactants were determined from interfacial tension, surface tension and contact angle measurements. A sand back model was utilized to examine the crude oil recovery factor at 50 °C. The obtained results indicated that, these surfactants have excellent performance in the term of surface activity and thermodynamics properties. Notably, AMAES-12 exhibits the most significant reduction in surface tension (16.3 mN/m) and the lowest interfacial tension (0.01 mN/m) at 50 ⁰C. The contact angle data demonstrated that, the prepared surfactants have efficiency to make alteration in wettability. The AMAES-12 achieved the maximum total oil recovery arrived 92.3% of the original from oil in place (OOIP). Physical sciences/Chemistry Physical sciences/Materials science Bi-functional anionic/ nonionic surfactants Surface active and thermodynamic properties Wettability alteration Dual moieties surfactants Chemical enhanced oil recovery Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Figure 10 Figure 11 Figure 12 Figure 13 Full Text Additional Declarations No competing interests reported. Tables 1 to 6 are available in the Supplementary Files section. Supplementary Files SupplementaryDataPaperI.docx Tables.docx Cite Share Download PDF Status: Published Journal Publication published 29 Dec, 2025 Read the published version in Scientific Reports → Version 1 posted Reviews received at journal 11 Oct, 2025 Reviewers agreed at journal 03 Oct, 2025 Reviewers agreed at journal 01 Oct, 2025 Reviewers agreed at journal 30 Sep, 2025 Reviewers agreed at journal 30 Sep, 2025 Reviewers invited by journal 30 Sep, 2025 Editor invited by journal 30 Sep, 2025 Editor assigned by journal 29 Sep, 2025 Submission checks completed at journal 26 Sep, 2025 First submitted to journal 22 Sep, 2025 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. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. 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-7685730","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Article","associatedPublications":[],"authors":[{"id":528008496,"identity":"1b9cef15-f950-42c6-98c6-b311ec27047e","order_by":0,"name":"Ahmed M. 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02:41:05","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":43321,"visible":true,"origin":"","legend":"\u003cp\u003eFT-IR Spectrum for NMAE\u003cstrong\u003e-10\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-7685730/v1/362597157ae910d58155a228.png"},{"id":93542952,"identity":"b2c906af-015d-4e82-a77b-844b0931aab4","added_by":"auto","created_at":"2025-10-15 02:41:05","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":37899,"visible":true,"origin":"","legend":"\u003cp\u003eH\u003csup\u003e1\u003c/sup\u003e NMR Spectrum for (NMAE-10)\u003c/p\u003e","description":"","filename":"5.png","url":"https://assets-eu.researchsquare.com/files/rs-7685730/v1/bd2b4ce18a3e8dfb7d4a7808.png"},{"id":93542953,"identity":"7127b9e5-3e12-4ae7-8029-a8ddd2271813","added_by":"auto","created_at":"2025-10-15 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12","display":"","copyAsset":false,"role":"figure","size":45463,"visible":true,"origin":"","legend":"\u003cp\u003eInjected Pore Volume Fraction against 3\u003csup\u003ery\u003c/sup\u003e Oil Recovery Factor (%) for the Prepared Surfactants\u003c/p\u003e","description":"","filename":"12.png","url":"https://assets-eu.researchsquare.com/files/rs-7685730/v1/cf68e233090e7e3bce9da991.png"},{"id":93544748,"identity":"e27c881c-b14c-4ba1-83c1-3393a8d8c763","added_by":"auto","created_at":"2025-10-15 02:57:06","extension":"png","order_by":13,"title":"Figure 13","display":"","copyAsset":false,"role":"figure","size":196148,"visible":true,"origin":"","legend":"\u003cp\u003eMechanism of Enhanced Oil Recovery\u003c/p\u003e","description":"","filename":"13.png","url":"https://assets-eu.researchsquare.com/files/rs-7685730/v1/85b1f4521d9cc8c9e7bbd4d4.png"},{"id":99545170,"identity":"29297ddc-9b94-468d-899b-31a221f17770","added_by":"auto","created_at":"2026-01-05 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02:41:05","extension":"docx","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":33955,"visible":true,"origin":"","legend":"","description":"","filename":"Tables.docx","url":"https://assets-eu.researchsquare.com/files/rs-7685730/v1/9c6d32a1142b224146fba89b.docx"}],"financialInterests":"\u003cp\u003eNo competing interests reported.\u003c/p\u003e\n\u003cp\u003eTables 1 to 6 are available in the Supplementary Files section.\u003c/p\u003e","formattedTitle":"Synthesis a New Family Hybrid Anionic / Nonionic Surfactant and Investigation their Physical Properties in relation to Chemical Enhanced Oil Recovery","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":true,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"Bi-functional anionic/ nonionic surfactants, Surface active and thermodynamic properties, Wettability alteration, Dual moieties surfactants, Chemical enhanced oil recovery","lastPublishedDoi":"10.21203/rs.3.rs-7685730/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-7685730/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThis study details the synthesis of a new class family of surfactants with dual anionic and nonionic moieties. The maleic anhydride reacted with 1-octene to prepare the corresponding 2-octenyl succinic anhydride. Then, this anhydride was esterified with prepared ethoxylated alcohols (ethylene oxide = 20 units) having different alkyl chains to obtain nonionic moiety surfactants named as; NMAE-10, NMAE-12 and NMAE-14. The sulfonation was carried for the nonionic surfactant by using sodium bisulfite to get three anionic moiety surfactants designated as; AMAES-10, AMAES-12 and AMAES-14. Infrared spectroscopy and ¹H NMR confirmed the surfactants' structures. At 50°C, Alkane carbon number (ACN) and n\u003csub\u003emin\u003c/sub\u003e were calculated by comparing n-hydrocarbon scans from n-C\u003csub\u003e6\u003c/sub\u003e to n-C\u003csub\u003e16\u003c/sub\u003e with the interfacial tension at the CMC. The work adhesion (W\u003csub\u003ea\u003c/sub\u003e), spreading coefficient and surface charge energy for these surfactants were determined from interfacial tension, surface tension and contact angle measurements. A sand back model was utilized to examine the crude oil recovery factor at 50 °C. The obtained results indicated that, these surfactants have excellent performance in the term of surface activity and thermodynamics properties. Notably, AMAES-12 exhibits the most significant reduction in surface tension (16.3 mN/m) and the lowest interfacial tension (0.01 mN/m) at 50 ⁰C. The contact angle data demonstrated that, the prepared surfactants have efficiency to make alteration in wettability. The AMAES-12 achieved the maximum total oil recovery arrived 92.3% of the original from oil in place (OOIP).\u003c/p\u003e","manuscriptTitle":"Synthesis a New Family Hybrid Anionic / Nonionic Surfactant and Investigation their Physical Properties in relation to Chemical Enhanced Oil Recovery","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-10-15 02:41:00","doi":"10.21203/rs.3.rs-7685730/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"editorInvitedReview","content":"","date":"2025-10-11T08:12:27+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"183942482089543712036082345171328893280","date":"2025-10-03T15:18:25+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"225740192227897150562750764672710980752","date":"2025-10-01T06:34:59+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"272876686534753154041688749241723782677","date":"2025-10-01T00:13:08+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"322623628868850749786547139899655018966","date":"2025-09-30T22:32:01+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-09-30T22:23:39+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"","date":"2025-09-30T20:47:32+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-09-29T09:41:48+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-09-26T14:17:19+00:00","index":"","fulltext":""},{"type":"submitted","content":"Scientific Reports","date":"2025-09-22T14:25:21+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"94aa8b7f-fbcd-45ce-955a-435b322580eb","owner":[],"postedDate":"October 15th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[{"id":56127584,"name":"Physical sciences/Chemistry"},{"id":56127585,"name":"Physical sciences/Materials science"}],"tags":[],"updatedAt":"2026-01-05T15:58:51+00:00","versionOfRecord":{"articleIdentity":"rs-7685730","link":"https://doi.org/10.1038/s41598-025-32367-2","journal":{"identity":"scientific-reports","isVorOnly":false,"title":"Scientific Reports"},"publishedOn":"2025-12-29 15:56:58","publishedOnDateReadable":"December 29th, 2025"},"versionCreatedAt":"2025-10-15 02:41:00","video":"","vorDoi":"10.1038/s41598-025-32367-2","vorDoiUrl":"https://doi.org/10.1038/s41598-025-32367-2","workflowStages":[]},"version":"v1","identity":"rs-7685730","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-7685730","identity":"rs-7685730","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}

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