Process for producing a glycolipid methyl ester

• US 4,216,311 A
• Filed: 11/17/1978
• Issued: 08/05/1980
• Est. Priority Date: 02/17/1978
• Status: Expired due to Term

• Current Assignee: Kao Soap Co., Ltd.
• Original Assignee: Kao Soap Co., Ltd.
• Inventors: Kimura, Yoshiharu, Inoue, Shigeo, Kinta, Manzo
• Primary Examiner(s): Brown, Johnnie R.
• Application Number:
  US05/961,555
• Time in Patent Office: 627 Days
• Field of Search: 536/4, 536/115, 536/116, 536/119, 536/120
• US Class Current: 536/115
• CPC Class Codes: C07H 15/04 attached to an oxygen atom of the saccharide radical
• CPC Class Codes: C11D 1/662 Carbohydrates or derivatives

Abstract

A glycolipid methyl ester represented by the formula (I), ##STR1## wherein R₃ represents a hydrogen atom or a methyl group, and R₄ represents a saturated or unsaturated hydrocarbon group having 12 to 16 carbon atoms when R₃ is a hydrogen atom, and R₄ represents a saturated or unsaturated hydrocarbon group having 11 to 15 carbon atoms when R₃ is a methyl group, is produced by adding at least one polyhydric alcohol represented by the formula (III) or (IV), ##STR2## wherein R₅ represents a hydrogen atom or a methyl group, R₆ and R₇ represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and m and n represent integers from 1 to 6, to hydrated Sophorolipid, removing water by distillation under reduced pressure, and subjecting the resulting Sophorolipid-polyhydric alcohol system to methanolysis and methylation by reaction with methanol in the presence of a strong acid.

Claims

1. A process for producing a glycolipid methyl ester represented by the formula (I), ##STR7## wherein R₃ represents hydrogen or methyl, and, R₄ represents a staurated or unsaturated hydrocarbon group having 12 to 16 carbon atoms when R₃ is hydrogen, and R₄ represents a saturated or unsaturated hydrocarbon group having 11 to 15 carbon atoms when R₃ is methyl, which comprises mixing at least one polyhydric alcohol represented by formula (III) or (IV), ##STR8## wherein R₅ represents hydrogen or methyl, R₆ and R₇ represent hydrogen or an alkyl group having 1 to 5 carbon atoms, and m and n represent integers from 1 to 6, with hydrated Sophorolipid;

removing water by distillation under reduced pressure; and

subjecting the resulting Sophorolipid-polyhydric alcohol system to methanolysis and methylation reactions by reaction with methanol in the presence of a strong acid.

2. The process according to claim 1, wherein the strong acid is used in a concentration of from 0.05 to 0.50 N.

3. The process according to claim 1, wherein the methanolysis and methylation reactions are conducted at a temperature below 45°

C.

4. The process according to claim 1, wherein said strong acid in nitric acid, sulfuric acid or hydrochloric acid.

5. The process according to claim 1, wherein from 1 to 10 wt. % of said polyhydric alcohol is added to said Sophorolipid.

6. The process according to claim 1, wherein said polyhydric alcohol is ethyleneglycol, ethyleneglycol monomethylether, ethyleneglycol monoethylether, ethyleneglycol monopropyl ether, diethyleneglycol, diethyleneglycol monomethyl ether, diethyleneglycol monoethyl ether, dimethyleneglycol monobutyl ether, polyethyleneglycol having an average molecular weight of 150 to 280, propyleneglycol, dipropyleneglycol, tripropyleneglycol, tetrapropyleneglycol, pentapropyleneglycol, hexapropyleneglycol, propyleneglyol monomethyl ether, propyleneglycol monoethyl ether, propyleneglycol monopropyl ether, propyleneglycol monobutyl ether, dipropyleneglycol monomethyl ether, dipropyleneglycol monoethyl ether, or tripropyleneglycol monomethyl ether.

7. The process according to claim 1, wherein said polyhydric alcohol is glycerine, polyglycerine, or blockpolymers of ethylene glycol and propyleneglycol.