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

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 18; no. 7; pp. 1994 - 2004
• Main Authors: Gozlan, Charlotte, Deruer, Elsa, Duclos, Marie-Christine, Molinier, Valerie, Aubry, Jean-Marie, Redl, Andreas, Duguet, Nicolas, Lemaire, Marc
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 01.01.2016; Royal Society of Chemistry
• Subjects: Acetals; Aldehydes; Aliphatic compounds; Chemical Sciences; Chemistry; Chemistry, Multidisciplinary; Ethers; Green & Sustainable Science & Technology; Hydrogenolysis; Organic chemistry; Physical Sciences; Science & Technology; Science & Technology - Other Topics; Surfactants; CYCLOPENTYL METHYL-ETHER; RAW-MATERIALS; HYDROTROPIC PROPERTIES; CATALYTIC REDUCTIVE ALKYLATION; N-ALKYLATION; CARBOHYDRATE; SELECTIVE SYNTHESIS; BIOSURFACTANTS; FATTY-ACID DERIVATIVES; GLYCEROL MONOETHERS
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c5gc02131f

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.