Anhydrosugar alcohol composition having enhanced storage stability, and anhydrosugar alcohol storage method

Patent metadata

Field	Value
Publication number	US-10766842-B2
Application number	US-201615779688-A
Country	US
Kind code	B2
Filing date	Oct 25, 2016
Priority date	Nov 30, 2015
Publication date	Sep 8, 2020
Grant date	Sep 8, 2020

Abstract

The present invention relates to an anhydrosugar alcohol composition having enhanced storage stability, and an anhydrosugar alcohol storage method, and more specifically, to an anhydrosugar alcohol composition having enhanced storage stability by comprising anhydrosugar alcohol and an amine-based additive; and to a method by which anhydrosugar alcohol having excellent quality may be provided by having the storing of the anhydrosugar alcohol performed under the existence of the amine-based additive, thereby remarkably enhancing the storage stability of the anhydrosugar alcohol.

First claim

The invention claimed is:

1. A composition comprising
a concentrated anhydrosugar alcohol; and
an amine compound as an additive for stabilization;
wherein the concentrated anhydrosugar alcohol is dianhydrohexitol in solid form,
wherein the amine compound is selected from the group consisting of piperidine, 1,8-diazabicycloundec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and combinations thereof, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of linear or branched C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, aminoC 1 -C 10 alkyl, mono- or di-C 1 -C 10 alkylaminoC 1 -C 10 alkyl, carboxamide and amino, and
wherein an amount of the amine compound is 1 ppm or more and 300 ppm or less, based on a weight of the concentrated anhydrosugar alcohol.

2. The composition of claim 1 , wherein the amine compound has a pKa of 8 to 15.

3. The composition of claim 1 , which shows a transmittance of 90% or higher to ultraviolet (UV) light with 275 nm wavelength when diluted as an aqueous solution of 20% by weight concentration.

4. The composition of claim 1 , which shows a pH of 6 to 8 when diluted as an aqueous solution of 20% by weight concentration.

5. A method for storing concentrated anhydrosugar alcohol, wherein the concentrated anhydrosugar alcohol is mixed with an amine compound as an additive for stabilization and the storage thereof is conducted,
wherein the concentrated anhydrosugar alcohol is dianhydrohexitol in solid form,
wherein the amine compound is selected from the group consisting of piperidine, 1,8-diazabicycloundec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and combinations thereof, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of linear or branched C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, aminoC 1 -C 10 alkyl, mono- or di-C 1 -C 10 alkylaminoC 1 -C 10 alkyl, carboxamide and amino, and
wherein an amount of the amine compound mixed with the concentrated anhydrosugar alcohol is 1 ppm or more and 300 ppm or less, based on a weight of the concentrated anhydrosugar alcohol.

6. The method for storing concentrated anhydrosugar alcohol of claim 5 , wherein the concentrated anhydrosugar alcohol stored is that obtained by distilling a dehydration reaction product liquid resulting from dehydration reaction of hexitol, purifying the distillation product, and then concentrating the purified product.

7. The method for storing concentrated anhydrosugar alcohol of claim 6 , wherein an acid catalyst is used in the dehydration reaction of hexitol.

8. The method for storing concentrated anhydrosugar alcohol of claim 6 , wherein the distillation is conducted by using a thin-film evaporator.

9. The method for storing concentrated anhydrosugar alcohol of claim 6 , wherein the purification is conducted by one or more processes selected from crystallization, decolorization, cation exchange resin treatment or anion exchange resin treatment.

10. The method for storing concentrated anhydrosugar alcohol of claim 6 , wherein in the purification, crystallization of the distillation product, decolorization of the crystallization product, and cation exchange resin treatment followed by anion exchange resin treatment of the decolorization product are conducted subsequently.

11. The method for storing concentrated anhydrosugar alcohol of claim 6 , wherein the concentration is conducted at a temperature of 90° C. to 110° C. under a pressure condition of 10 mmHg to 100 mmHg for 30 minutes or longer.

Assignees

• Samyang Corp

Inventors

• Ryu Hoon
• Yoo Seung Hyun
• Lee Hyun Seung
• Im Jun Seop
• Jung Young Jae

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D307/62

  Three oxygen atoms, e.g. ascorbic acid · CPC title

• C07D233/58

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms · CPC title

• C07D211/12

  with only hydrogen atoms attached to the ring nitrogen atom · CPC title