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Use of Furandicarboxylic Acid and Its Decyl Ester as Additives in the Fischer's Glycosylation of Decanol by d ‐Glucose: Physicochemical Properties of the Surfactant Compositions Obtained
Author(s) -
Es Daan S.,
Marinkovic Sinisa,
Oduber Xavier,
Estrine Boris
Publication year - 2013
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-012-1382-8
Subject(s) - chemistry , pulmonary surfactant , sulfuric acid , yield (engineering) , polyester , catalysis , organic chemistry , furan , biodegradation , glycosylation , biochemistry , materials science , metallurgy
2,5‐Furandicarboxylic acid is a promising bio‐based platform chemical that may serve as a ‘green’ substitute for terephthalate in polyesters. In the present work, straightforward glycosylation of decanol with unprotected and non‐activated d ‐glucose was performed under reduced quantities of sulfuric acid as catalyst (down to 0.9 mol%) in the presence of 2,5‐furandicarboxylic acid or its n ‐decyl ester as additive. Yield of decyl monoglucosides was highly improved by the use of the additives. Moreover, the presence of additive also limited the colouration of the reaction. The physical and chemical properties of the surfactant composition produced were studied and compared to reference compositions. The ultimate biodegradability of furan‐2,5‐dicarboxylic acid (FDCA) and its n ‐decyl ester formed or produced in the bulk reaction medium was also studied in order to assess its potential use in surfactant industry.