Method of producing bio-derived branched alkyl glyceryl ether, and bio-derived branched alkyl glyceryl ether produced by said method

Patent metadata

Field	Value
Publication number	US-12528755-B2
Application number	US-202318871701-A
Country	US
Kind code	B2
Filing date	Oct 2, 2023
Priority date	Oct 7, 2022
Publication date	Jan 20, 2026
Grant date	Jan 20, 2026

Abstract

The present invention relates to a method of producing a bio-derived branched alkyl glyceryl ether, including: a step of providing a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, the step including dimerizing one kind or two or more kinds selected from the group consisting of: a bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms; a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms; a bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms; and a bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms; and a step of producing a bio-derived branched alkyl glyceryl ether by using the resultant bio-derived branched primary alcohol, and a bio-derived branched alkyl glyceryl ether obtained by the production method.

First claim

The invention claimed is:

1 . A method of producing a bio-derived branched alkyl glyceryl ether, comprising:
a step of dimerizing a bio-derived compound to produce a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, wherein the bio-derived compound is one or more selected from the group consisting of: a bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms; a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms; a bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms; and a bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms; and a step of reacting the bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms to produce a bio-derived branched alkyl glyceryl ether.

2 . The method of producing a bio-derived branched alkyl glyceryl ether according to claim 1 , wherein the step of reacting the bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms to produce the bio-derived branched alkyl glyceryl ether comprises:
a hydrination step of reacting the bio-derived branched primary alcohol and bio-derived epichlorohydrin with each other to provide a hydrinated product; a ring-closing step of ring-closing the hydrinated product by a ring-closing reaction to provide a ring-closed product; and a ring-opening step of ring-opening the resultant ring-closed product by a ring-opening reaction to provide the bio-derived branched alkyl glyceryl ether.

3 . The method of producing a bio-derived branched alkyl glyceryl ether according to claim 2 , wherein the hydrination step comprises subjecting a mixture of the bio-derived branched primary alcohol and the bio-derived epichlorohydrin to a reaction at from 20° C. to 150° C. for from 1 minute to 24 hours while performing heating and/or cooling to provide the hydrinated product.

4 . The method of producing a bio-derived branched alkyl glyceryl ether according to claim 2 , wherein the ring-closing step comprises adding an alkali agent to the hydrinated product followed by mixing and allowing the reaction to proceed at from 20° C. to 150° C. for from 1 minute to 24 hours while performing heating and/or cooling to condense the hydrinated product thereby providing the ring-closed product.

5 . The method of producing a bio-derived branched alkyl glyceryl ether according to claim 2 , wherein the ring-opening step comprises adding water to the ring-closed product and subjecting the mixture to a reaction at from 20° C. to 200° C. for from 1 minute to 24 hours while performing heating and/or cooling under a reduced pressure or pressurized environment in the presence of a catalyst to produce the bio-derived branched alkyl glyceryl ether.

6 . A method of producing a bio-derived branched alkyl glyceryl ether, comprising:
a step of dimerizing a bio-derived compound in the presence of a catalyst or a basic compound at 60 to 320° C. to produce a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, wherein the bio-derived compound is one or more selected from the group consisting of: a bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms; a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms; a bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms; and a bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms; and a step of reacting the bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms to produce a bio-derived branched alkyl glyceryl ether, wherein the step of reacting the bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms to produce the bio-derived branched alkyl glyceryl ether comprises:
a hydrination step comprising subjecting a mixture of the bio-derived branched primary alcohol and bio-derived epichlorohydrin to a reaction at from 20° C. to 150° C. for from 1 minute to 24 hours while performing heating and/or cooling to provide a hydrinated product,
a ring-closing step of ring-closing the hydrinated product comprising adding an alkali agent to the hydrinated product followed by mixing and allowing the reaction to proceed at from 20° C. to 150° C. for from 1 minute to 24 hours while performing heating and/or cooling to condense the hydrinated product thereby providing a ring-closed product, and
a ring-opening step of ring-opening the ring-closed product comprising adding water to the ring-closed product and subjecting the mixture to a reaction at from 20° C. to 200° C. for from 1 minute to 24 hours while performing heating and/or cooling under a reduced pressure or pressurized environment in the presence of a catalyst to produce the bio-derived branched alkyl glyceryl ether.

7 . The method of producing a bio-derived branched alkyl glyceryl ether according to claim 1 , wherein the step of dimerizing comprises dimerizing one or more selected from the group consisting of bio-derived n-butanol, bio-derived n-butenyl alcohol, bio-derived n-butyl aldehyde, and bio-derived n-butene aldehyde.

8 . The method of producing a bio-derived branched alkyl glyceryl ether according to claim 6 , wherein the step of dimerizing comprises dimerizing one or more selected from the group consisting of bio-derived n-butanol, bio-derived n-butenyl alcohol, bio-derived n-butyl aldehyde, and bio-derived n-butene aldehyde.

Assignees

• Adeka Corp

Inventors

• Inoue Takahiro
• Takata Masahiro
• Hamasaki Toshio

Classifications

• A61K2800/10

  General cosmetic use · CPC title

• A61Q5/02 Primary

  Preparations for cleaning the hair · CPC title

• A61Q19/10

  Washing or bathing preparations · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K8/345

  containing more than one hydroxy group · CPC title