Ring opening of epoxidized methyl or ethyl oleate by alkyl glycosides

• Published in: European journal of lipid science and technology Vol. 119; no. 7
• Main Authors: Epoune Lingome, Cédric, Gadenne, Benoit, Alfos, Carine, Queneau, Yves, Moebs‐Sanchez, Sylvie
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 01.07.2017; Wiley-VCH Verlag [2000-....]
• Subjects: Alkyl glycosides; Biopharmaceuticals; Carbohydrates; Chains (polymeric); Chemical industry; Chemical Sciences; Esters; FAMES; Formulations; Glucosides; Glycosides; Hydroxyl alkyl ethers; Intermediates; Internal epoxides; Ketones; Lanthanide triflates; Lubricants; Organic chemistry; Polymers; Polyols; Renewable resources; Ring opening; Selectivity; Temperature effects; Transesterification; Vegetable oils
• ISSN: 1438-7697; 1438-9312
• DOI: 10.1002/ejlt.201600413

Epoxidized methyl or ethyl oleate were used as models of FAtty Methyl Esters to explore their functionalization via ring opening of the internal epoxide by alkyl glycosides. Overcoming solubility issues, medium to long‐chain alkyl glucosides gave better results than methyl glucoside. Er(OTf)3 turned out to catalyze at room temperature the selective formation of hydroxyalkylethers with good yields versus transesterification, despite the concomitant formation of fatty ketones. A brief scope of the reaction, using several available alkyl glycosides, suggests that the strategy can easily lead to new highly functionnalized amphiphilic compounds, potential precursors for biobased materials. Practical applications: Interested in the formation of original high‐value intermediates from renewable materials, we tackled the reaction of unprotected carbohydrates and unsaturated vegetal oils featuring an internal epoxide. After ring‐opening, the obtained highly functionalized polyols are potential precursors to produce new biobased polymers, lubricants or surface‐active compounds for high‐value cosmetic or biopharmaceutical formulations. The formation of hydroxyalkylethers from epoxidized fatty esters and alkyl glycosides are catalyzed by Er(OTf)3 at room temperature with good yields and high selectivity versus transesterification. The formation of hydroxyalkylethers from epoxidized fatty esters and alkyl glycosides are catalyzed by Er(OTf)3 at room temperature with good yields and high selectivity versus transesterification.