Carboxylic acid esters of xylitol and process for enzymatically preparing same

Patent metadata

Field	Value
Publication number	US-2023033620-A1
Application number	US-202017757711-A
Country	US
Kind code	A1
Filing date	Dec 17, 2020
Priority date	Dec 20, 2019
Publication date	Feb 2, 2023
Grant date	—

Abstract

Xylitol carboxylates are products of interest in the food and cosmetics industries. A process can be used for the enzymatic preparation of xylitol carboxylates.

First claim

1 : A xylitol carboxylate, comprising:
at least one carboxylic ester of xylitol, and at least one of a carboxylic ester of 1,4-anhydroxylitol, a carboxylic ester of 1,4-anhydroarabitol, and a carboxylic ester of 1,4-anhydroribitol, wherein a ratio by weight of xylitol residues present in the xylitol carboxylate to a sum total of all 1,4-anhydroxrlitol residues, 1,4-anhydroarabitol residues, and 1,4-anhydroribitol residues present in the xylitol carboxylate is greater than or equal to 96:4, and wherein a molar ratio of esterified primary hydroxyl groups to esterified secondary hydroxyl groups in the at least one carboxylic ester of xylitol is 80:20 to 20:80.

2 : The xylitol carboxylate according to claim 1 , wherein a carboxylic acid component is derived from a carboxylic acid containing 2 to 34, carbon atoms or a mixture thereof.

3 : The xylitol carboxylate according to claim 1 , wherein an average degree of esterification of the at least one carboxylic ester of xylitol present is from 1.0 to 4.0.

4 : The xylitol carboxylate according to claim 1 , wherein the at least one carboxylic ester of xylitol present comprise monoesters of xylitol, diesters of xylitol and triesters of xylitol.

5 : The xylitol carboxylate according to claim 1 , wherein the xylitol carboxylate comprises 0.05% to 40% by weight, of free xylitol.

6 : The xylitol carboxylate according to claim 1 , wherein the xylitol carboxylate comprises less than 25% by weight of at least one free carboxylic acid.

7 : The xylitol carboxylate according to claim 1 , wherein a total monoester component of the at least one carboxylic ester of xylitol contains from 5% by weight to 25% by weight of secondary ester regioisomers.

8 : The xylitol carboxylate according to claim 1 , wherein a total monoester component of the at least one carboxylic ester of xylitol and a total diester component of the at least one carboxylic ester of xylitol each comprise at least two regioisomers.

9 : A process for the enzymatic preparation of a xylitol carboxylate, comprising:
A) providing xylitol and at least one acyl group donor, B) reacting the xylitol with the at least one acyl group donor in the presence of a lipase at a temperature of from 75° C. to 110° C., to give a xylitol carboxylate, and C) optionally, purifying the xylitol carboxylate.

10 : The process according to claim 9 , wherein A) comprises blending the xylitol and the at least one acyl group donor for at least ten minutes.

11 : The process according to claim 9 , wherein in B), the xylitol and the at least one acyl group donor make up at least 80% by weight, based on an overall reaction mixture at the start of B).

12 : The process according to claim 9 , wherein the lipase is selected from the group consisting of a lipase from Thermomyces lanuginosus , a lipases A or B from Candida antarctica , a lipase from Mucor miehei , a lipase from Humicola sp., a lipase from Rhizomucor javanicus , a lipase from Rhizopus oryzae , a lipase from Candida rugosa , a lipase from Rhizopus niveus , a lipase from Penicillium camemberti , a lipase from Aspergillus niger , a lipase from Penicillium cyclopium, and a respective at least 60% homologue at an amino acid level.

13 : The process according to claim 9 , wherein B) is carried out at a pressure of less than 1 bar.

14 : A xylitol carboxylate obtainable by the process according to claim 9 .

15 : The xylitol carboxylate according to claim 1 , wherein the xylitol carboxylate is a viscosity regulator, a care active ingredient, a foam booster or solubilizer, a antimicrobial agent, a antistat, a binder, a corrosion inhibitor, a dispersant, an emulsifier, a film former, a humectant, an opacifier, an oral care agent, a preservative, a skincare agent, a hydrophilic emollient, a foam stabilizer, or a nonionic surfactant.

16 : The xylitol carboxylate according to claim 1 , wherein the molar ratio of esterified primary hydroxyl groups to esterified secondary hydroxyl groups in the at least one carboxylic ester of xylitol is from 65:35 to 40:60.

17 : The xylitol carboxylate according to claim 2 , wherein the carboxylic acid component is derived from a natural fatty acid or a mixture thereof.

18 : The xylitol carboxylate according to claim 4 , wherein the triesters of xylitol are present in an amount of from 10% to 50% by weight, based on all carboxylic esters of xylitol present.

19 : The process according to claim 9 , wherein the at least one acyl group donor is selected from the group consisting of fatty acid esters and fatty acids.

20 : The process according to claim 10 , wherein in A), the blending is carried out within a temperature range from 80° C. to 120° C.

Assignees

• Evonik Operations Gmbh

Inventors

• Liebig Stefan Julian
• Von Hof Jan Marian
• Böhmer Thomas
• Thomalla Thomas
• Brandt Kathrin Daniela
• Hartung Christian
• Wenk Hans Henning
• Yavorsky Maxim
• Karacocuk Sunay

Classifications

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C12P7/6436 Primary

  Fatty acid esters · CPC title

• C12N9/20 Primary

  Triglyceride splitting, e.g. by means of lipase · CPC title

• Y02E50/10

  Biofuels, e.g. bio-diesel · CPC title

• C12P19/04

  Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds · CPC title