Synthesis of monoethers of sugar comprising a long alkyl chain and uses thereof as a surfactant

• US 10,442,830 B2
• Filed: 12/03/2015
• Issued: 10/15/2019
• Est. Priority Date: 12/03/2014
• Status: Expired due to Fees

• Current Assignee: Centre National De La Recherche Scientifique, Tereos Starch & Sweeteners Belgium, Université Claude Bernard Lyon 1
• Original Assignee: Tereos Starch & Sweeteners Belgium
• Inventors: Gozlan, Charlotte, Duclos, Marie-christine, Duguet, Nicolas, Lemaire, Marc, Redl, Andreas
• Primary Examiner(s): Olson, Eric
• Application Number:
  US15/533,361
• Publication Number:
  US 20180265533A1
• Time in Patent Office: 1,412 Days
• CPC Class Codes: C07C 43/04 Saturated ethers
• CPC Class Codes: C07C 43/10 of polyhydroxy compounds
• CPC Class Codes: C07C 43/14 Unsaturated ethers
• CPC Class Codes: C07C 43/15 containing only non-aromatic carbon-to-carbon double bonds
• CPC Class Codes: C07D 307/20 Oxygen atoms
• CPC Class Codes: C07H 1/00 Processes for the preparation of sugar derivatives
• CPC Class Codes: C07H 1/06 Separation; Purification
• CPC Class Codes: C07H 15/04 attached to an oxygen atom of the saccharide radical
• CPC Class Codes: C07H 3/02 Monosaccharides
• CPC Class Codes: C09K 23/42 Ethers, e.g. polyglycol ethers of alcohols or phenols
• CPC Class Codes: C11D 1/662 Carbohydrates or derivatives
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

A process for obtaining a mixture of C4-C8 and C9-C18 alkyl monoether of saccharide, comprising: a) a first step of acetalization or trans-acetalization of a saccharide or of a mixture of saccharides with a C4-C8 aliphatic aldehyde or the acetal thereof, b) a second consecutive or simultaneous step of acetalization or trans-acetalization of the product obtained in a) of the saccharide or mixture of saccharides with a C9-C18 aliphatic aldehyde or the acetal thereof, c) a step of catalytic hydrogenolysis of the saccharide acetals obtained, and d) a step of recovery of a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers. The invention further relates to a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers and the use thereof as a surfactant.

Claims

1. A process for obtaining a mixture of C4-C8 alkyl monoether of saccharide and/or of saccharide derivative and of C9-C18 alkyl monoether of saccharide and/or of saccharide derivative, said saccharide derivative being a glycosylated and/or hydrogenated and/or dehydrated saccharide, said process comprising:

a) a first step of acetalization or trans-acetalization of a saccharide, of saccharide derivative or of mixtures thereof with a C4-C8 aliphatic aldehyde or the acetal thereof,

b) a second consecutive or simultaneous step of acetalization or trans-acetalization of the product obtained in a), of the saccharide, of the saccharide derivative or of mixtures thereof, with a C9 to C 18 aliphatic aldehyde or the acetal thereof,

c) a step of catalytic hydrogenolysis of the acetals of saccharide and/or of saccharide derivative obtained in b), and

d) a step of recovery of a mixture of C4-C8 alkyl monoether of saccharide and/or of saccharide derivative and of C9-C18 alkyl monoether of saccharide and/or of saccharide derivative.

2. The process as claimed in claim 1, in which said saccharide derivative is a monoanhydrosaccharide or a C1-C4 alkyl glycoside.

3. The process as claimed in claim 1, in which said saccharide derivative is an anhydrosaccharide or an alkyl glycoside.

4. The process as claimed claim 1, in which said saccharide is a monosaccharide, a disaccharide or a trisaccharide.

5. The process as claimed claim 1, in which said saccharide and/or derivative of saccharide comprises from 4 to 7 carbon atoms.

6. The process as claimed claim 1, in which said saccharide derivative is a sugar alcohol selected from the group consisting of erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, iditol, volemitol, isomalt, maltitol, lactitol, maltotriitol, maltotetraitol, polyglycitol and the process further comprises a dehydration step, before said step a) of first acetalization or trans-acetalization.

7. The process as claimed in claim 1, in which said saccharide derivative is an alkyl glycoside selected from a group consisting of methyl glucoside, ethyl glucoside, propyl glucoside, butyl glucoside, methyl xyloside, ethyl xyloside, propyl xyloside, butyl xyloside, methyl mannoside, ethyl mannoside, propyl mannoside, butyl mannoside, methyl galactoside, ethyl galactoside, propyl galactoside and butyl galactoside.

8. The process as claimed in claim 1, in which the C4-C8 aliphatic aldehyde is a C5 aliphatic aldehyde or the acetal of the latter and/or the C9 to C18 aliphatic aldehyde or the acetal of the latter is a C12 aliphatic aldehyde or the acetal thereof.

9. The process as claimed claim 1, in which the molar ratio (C4-C8 or C9-C18 aliphatic aldehyde or acetal thereof):

(saccharide, the derivative of saccharide or mixtures thereof) is between 5;

1 and 1;

5.

10. The process as claimed claim 1, in which the first and/or second step of acetalization or trans-acetalization is carried out in the presence of an acid catalyst, wherein the first and/or second step of acetalization or transacetalization is carried out in conditions without solvent or in the presence of a polar solvent.

11. The process as claimed claim 1, in which hydrogenolysis is carried out at a temperature between 80 and 140°

C. and/or at a pressure between 15 and 50 bar, in the presence of a catalyst based on precious metals, on base metals in the group of ferrous metals.

15. The process as claimed in claim 5, wherein said saccharide and/or saccharide derivative is selected from:

a hexose selected from a group consisting of glucose, mannose, galactose, allose, altrose, gulose, idose or talose, and

a hexitan selected from a group consisting of 1,4-anhydro-D-sorbitol;

1,5-anhydro-D-sorbitol;

3,6-anhydro-D-sorbitol;

1,4 (3,6)-anhydro-D-mannitol;

1,5-anhydro-D-mannitol;

3,6-anhydro-D-galactitol;

1,5-anhydro-D-galactitol;

1,5-anhydro-D-talitol; and

2,5-anhydro-L-iditol.

12. A composition comprising a mixture of positional isomers of C4-C8 alkyl monoether of saccharide or of saccharide derivative and of positional isomers of C9-C18 alkyl monoether of saccharide or of saccharide derivative, in which the saccharide derivative is a glycosylated and/or hydrogenated and/or dehydrated saccharide, and the saccharide is a hexose.

13. The composition as claimed in claim 12, in which the C4-C8 alkyl group is a C5 alkyl and the C9-C18 alkyl group is a C12 alkyl, the saccharide derivative being selected from monoanhydrosorbitol or alkylglucoside.

14. The composition as claimed claim 12, in which the ratio of C5 alkyl monoether of saccharide or of saccharide derivative/C 12 alkyl monoether of saccharide or of saccharide derivative is between 5:

95 and 95;

5.

16. The composition as claimed in claim 12, wherein the saccharide derivative is methyl glucoside.

20. The composition as claimed in claim 12, said composition being a surfactant composition, and wherein said surfactant composition is selected from a detergent, an emulsifier, an emulsion stabilizer, a foaming agent, a foam stabilizer, a liposome stabilizer, a dispersant, and a wetting agent.

17. A method for reducing the surface tension of a liquid, said method comprising:

contacting a liquid with;

a composition comprising a mixture of C4-C8 alkyl monoether of saccharide and/or of saccharide derivative and of C9-C18 alkyl monoether of saccharide and/or of saccharide derivative, or

a composition comprising a mixture of positional isomers of C4-C8 alkyl monoether of saccharide or of saccharide derivative and of positional isomers of C9-C18 alkyl monoether of saccharide or of saccharide derivative, in which the saccharide derivative is a glycosylated and/or hydrogenated and/or dehydrated saccharide, and the saccharide is a hexose, or

a mixture of C4-C8 alkyl monoether of saccharide and/or of saccharide derivative and of C9-C18 alkyl monoether of saccharide and/or of saccharide derivative, said saccharide derivative being a glycosylated and/or hydrogenated and/or dehydrated saccharide, obtained by a process comprising;

a) a first step of acetalization or trans-acetalization of a saccharide, of saccharide derivative or of mixtures thereof with a C4-C8 aliphatic aldehyde or the acetal thereof,

b) a second consecutive or simultaneous step of acetalization or trans-acetalization of the product obtained in a), of the saccharide, of the saccharide derivative or of mixtures thereof, with a C9 to C 18 aliphatic aldehyde or the acetal thereof,

c) a step of catalytic hydrogenolysis of the acetals of saccharide and/or of saccharide derivative obtained in b), and

d) a step of recovery of the mixture of C4-C8 alkyl monoether of saccharide and/or of saccharide derivative and of C9-C18 alkyl monoether of saccharide and/or of saccharide derivative.

18. The method as claimed in claim 17, wherein the mixture of C4-C8 alkyl monoether of saccharide and/or of saccharide derivative and of C9-C18 alkyl monoether of saccharide and/or of saccharide derivative is a mixture of C5 alkyl monoether of saccharide and/or of saccharide derivative and of C12 alkyl monoether of saccharide and/or of saccharide derivative and in which said saccharide derivative is selected from monoanhydrosorbitol or alkyl glucoside.

19. The method as claimed in claim 17, wherein said saccharide derivative is methyl glucoside.