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Issue 7, 2016
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Preparation of amphiphilic sorbitan monoethers through hydrogenolysis of sorbitan acetals and evaluation as bio-based surfactants

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Abstract

Amphiphilic sorbitan acetals have been prepared from sorbitan by acetalisation using linear aliphatic aldehydes or by transacetalisation starting from the corresponding aldehyde diethylacetals. A series of sorbitan acetals has been obtained with 29–81% isolated yields. It has been shown that these sorbitan acetals exist as a mixture of five-membered and six-membered regioisomers. Hydrogenolysis of the mixtures gave the corresponding sorbitan ethers as a mixture of 3 regioisomers with 55–85% isolated yields. A one-pot two-step procedure was also optimized from sorbitan giving similar results. The amphiphilic properties of sorbitan acetals and ethers were evaluated and both families exhibit interesting surfactant properties.

Graphical abstract: Preparation of amphiphilic sorbitan monoethers through hydrogenolysis of sorbitan acetals and evaluation as bio-based surfactants

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Article information


Submitted
09 Sep 2015
Accepted
13 Nov 2015
First published
24 Nov 2015

Green Chem., 2016,18, 1994-2004
Article type
Paper

Preparation of amphiphilic sorbitan monoethers through hydrogenolysis of sorbitan acetals and evaluation as bio-based surfactants

C. Gozlan, E. Deruer, M. Duclos, V. Molinier, J. Aubry, A. Redl, N. Duguet and M. Lemaire, Green Chem., 2016, 18, 1994
DOI: 10.1039/C5GC02131F

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