Method for preparing long-chain alkyl cyclic acetals made from sugars

Patent metadata

Field	Value
Publication number	US-9499559-B2
Application number	US-201414898475-A
Country	US
Kind code	B2
Filing date	Jun 13, 2014
Priority date	Jun 14, 2013
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

Long-chain alkyl cyclic acetals made from sugars are obtainable by a method that comprises the steps consisting of:
dehydrating a hexitol in a monoanhydrohexitol substrate; reacting the monoanhydrohexitol substrate obtained with an alkyl aldehyde reagent containing 5 to 18 carbon atoms, by means of an acetalization reaction with a substrate/reagent ratio of between 5:1 and 1:1, or with a derivative of an alkyl aldehyde reagent containing 5 to 18 carbon atoms, by means of a transacetalization reaction with a substrate/reagent ratio of between 1:1 and 1:3, in the presence of acid catalyst and in an environment that is free of solvent or that consists of non-aqueous polar solvent; collecting the long-chain alkyl acetal of hexitan from the mixture obtained.

First claim

The invention claimed is:

1. A method for preparing long-chain alkyl cyclic acetals made from sugars, characterized in that the method comprises the following steps:
dehydrating a hexitol in a monoanhydrohexitol substrate;
reacting the monoanhydrohexitol substrate obtained with an alkyl aldehyde reagent containing 5 to 18 carbon atoms, by means of an acetalization reaction with a substrate/reagent ratio of between 5:1 and 1:1, or with a derivative of an alkyl aldehyde reagent containing 5 to 18 carbon atoms, by means of a transacetalization reaction with a substrate/reagent ratio of between 1:1 and 1:3, in the presence of acid catalyst and in an environment that is free of solvent or that consists of non-aqueous polar solvent; and
collecting the long-chain alkyl acetal of hexitan from the mixture obtained.

2. The method as claimed in claim 1 , wherein the hexitol is selected from the group comprising: sorbitol, mannitol, galactitol and iditol.

3. The method as claimed in claim 2 , wherein the hexitol is sorbitol.

4. The method as claimed in claim 1 , wherein said alkyl aldehyde reagent contains 8 to 12 carbon atoms.

5. The method as claimed in claim 1 , wherein said non-aqueous polar solvent is selected from the group consisting of: DMF, DMSO, DMA, acetonitrile, THF, methyl THF and ethyl acetate.

6. The method as claimed in claim 1 , wherein the long-chain alkyl acetal of hexitan is collected by separation.

7. The method as claimed in claim 3 , wherein said monoanhydrohexitol substrate is purified 1,4-sorbitan.

8. The method as claimed in claim 7 , wherein said long-chain alkyl acetal of hexitan is composed of four diastereoisomers.

Assignees

• Syral Belgium Nv
• Univ Claude Bernard Lyon
• Centre Nat De La Rech Scient (C N R S )

Inventors

• Gozlan Charlotte
• Duguet Nicolas
• Lemaire Marc
• Queneau Yves
• Redl Andreas

Classifications

• C07D407/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title