Production of levoglucosan and levoglucosenone from cellulose using Brønsted acid catalysts in polar aprotic solvents

Production of levoglucosan and levoglucosenone from cellulose using Brønsted acid catalysts in polar aprotic solvents | 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 Production of levoglucosan and levoglucosenone from cellulose using Brønsted acid catalysts in polar aprotic solvents Alexa M. González-Rosario, Oscar Oyola-Rivera, Nelson Cardona-Martínez This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4451040/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 29 Aug, 2024 Read the published version in Waste and Biomass Valorization → Version 1 posted 5 You are reading this latest preprint version Abstract Levoglucosan and levoglucosenone are important platform molecules typically produced by pyrolysis of cellulosic feedstocks. Commercial manufacture of levoglucosenone uses phosphoric acid in sulfolane to convert cellulose at high temperatures and catalyst concentrations. We report the synthesis of levoglucosan and levoglucosenone from cellulose at moderate temperatures in polar aprotic solvents using low concentrations of Brønsted acid catalysts. We discovered that the basicity of the solvents has a linear relationship with the cellulose reaction rate. The initial turnover frequency of cellulose conversion increased as the basicity of the solvent decreased. Using a flow reactor with a reactive bed to produce levoglucosan and levoglucosenone we found that moderate temperatures promoted the production of levoglucosan and levoglucosenone, whereas higher temperatures promoted degradation reactions, decreasing the yields of levoglucosan and levoglucosenone. We also found that catalysts with high pK a (lower strength) only promoted the production of levoglucosan and its isomerization, whereas using a catalyst with a low pK a (higher strength) favored subsequent reactions and degradation products, like when we used high temperatures. At 430 K with a flow rate of 1.5 mL/min of 5 mM sulfuric acid in γ-valerolactone, we found yields of up to 34 and 24 wt% for levoglucosan and levoglucosenone, respectively. Cellulose levoglucosan levoglucosenone sulfuric acid γ-valerolactone Full Text Cite Share Download PDF Status: Published Journal Publication published 29 Aug, 2024 Read the published version in Waste and Biomass Valorization → Version 1 posted Reviewers agreed at journal 16 Jun, 2024 Reviewers invited by journal 16 Jun, 2024 Editor invited by journal 11 Jun, 2024 Editor assigned by journal 21 May, 2024 First submitted to journal 20 May, 2024 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-4451040","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":314984221,"identity":"a0b64626-67e5-44b3-9adb-4f9387ec85b2","order_by":0,"name":"Alexa M. 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Commercial manufacture of levoglucosenone uses phosphoric acid in sulfolane to convert cellulose at high temperatures and catalyst concentrations. We report the synthesis of levoglucosan and levoglucosenone from cellulose at moderate temperatures in polar aprotic solvents using low concentrations of Brønsted acid catalysts. We discovered that the basicity of the solvents has a linear relationship with the cellulose reaction rate. The initial turnover frequency of cellulose conversion increased as the basicity of the solvent decreased. Using a flow reactor with a reactive bed to produce levoglucosan and levoglucosenone we found that moderate temperatures promoted the production of levoglucosan and levoglucosenone, whereas higher temperatures promoted degradation reactions, decreasing the yields of levoglucosan and levoglucosenone. 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