Process for the isolation of reaction products from sugar alcohol or anhydrosugar alcohol hydrogenolysis reaction mixtures using simulated moving bed chromatography

Patent metadata

Field	Value
Publication number	US-10017439-B2
Application number	US-201715649106-A
Country	US
Kind code	B2
Filing date	Jul 13, 2017
Priority date	Apr 10, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

A method of isolating and purifying a product of sugar alcohol or anhydrosugar alcohol hydrogenolysis from a reaction mixture containing sorbitans, 1,2,4-butanetriol (BTO), 1,2,5,6-hexanetetrol (HTO), among other byproducts of a hydrogenolysis reaction of a sugar alcohol and/or a mono- or di-dehydrative product of a sugar alcohol is described. The method involves contacting the mixture having the products of sugar alcohol or anhydrosugar alcohol hydrogenation and other C 1 -C 6 alcohols and polyols with a resin material adapted for chromatography under conditions where the products preferentially associates with the resin relative to other components in the mixture, and eluting products from the resin with a solvent. The method suggests a way for separation of aliphatic polyols generated from the hydrogenolysis of sugar alcohols or anhydrosugar alcohols.

First claim

We claim:

1. A method of purifying a product mixture comprising: contacting a mixture comprising sorbitans and other C 1 -C 6 alcohols and polyols with a resin material adapted for chromatography, under conditions where said sorbitans preferentially associate with the resin material relative to other components in the mixture; and eluting said sorbitans from said resin material with a solvent.

2. The method according to claim 1 , wherein said resin material is either 1) a non-functionalized resin material, or 2) is either an acidic or basic functionalized resin in neutral form.

3. The method according to claim 1 , wherein said resin material adapted for chromatography has a matrix composed of a polystyrene divinyl-benzene material.

4. The method according to claim 2 , wherein said resin material has either 1) a Gaussian particle size distribution, or 2) a mono-dispersed particle size.

5. The method according to claim 1 , wherein said resin material has a particle size in a range from about 200 μm to about 850 μm.

6. The method according to claim 5 , wherein said resin material has a particle size in a range from about 250 μm to about 500 μm.

7. The method according to claim 1 , wherein said resin material has an operational temperature in a range of about 15° C. to about 100° C.

8. The method according to claim 1 , wherein an elution solvent is selected from the group consisting of deionized water, methanol, butanol, isopropanol, simple aliphatic alcohols, or a mixture thereof.

9. The method according to claim 1 , wherein said method of purifying results in a yield of sorbitans of at least 60% wt./wt. at a purity level of at least 80%.

10. The method according to claim 1 , wherein said mixture contacts an ion exchange resin before contacting said resin material adapted for chromatography.

11. The method according to claim 10 , wherein said contacting with said ion exchange resin is performed either in a single step by contacting a mixed-bed acid/base resin, or in two steps by contacting an acid resin first, then base resin second or the reverse with base resin first and then acid resin second.

12. A method of purifying a product mixture comprising: contacting a mixture comprising 1,2,4-butanetriol and other C 1 -C 6 alcohols and polyols with a resin material adapted for chromatography, under conditions where said 1,2,4-butanetriol preferentially associates with the resin material relative to other components in the mixture; and eluting said 1,2,4-butanetriol from said resin material with a solvent.

13. The method according to claim 12 , wherein said resin material is either 1) a non-functionalized resin material, or 2) is either an acidic or basic functionalized resin in neutral form.

14. The method according to claim 12 , wherein said resin material adapted for chromatography has a matrix composed of a polystyrene divinyl-benzene material.

15. The method according to claim 13 , wherein said resin material has either 1) a Gaussian particle size distribution, or 2) a mono-dispersed particle size.

16. The method according to claim 12 , wherein said resin material has a particle size in a range from about 200 μm to about 850 μm.

17. The method according to claim 16 , wherein said resin material has a particle size in a range from about 250 μm to about 500 μm.

18. The method according to claim 12 , wherein said resin material has an operational temperature in a range of about 15° C. to about 100° C.

19. The method according to claim 12 , wherein an elution solvent is selected from the group consisting of deionized water, methanol, butanol, isopropanol, simple aliphatic alcohols, or a mixture thereof.

20. The method according to claim 12 , wherein said method of purifying results in a yield of 1,2,4-butanetriol of at least 60% wt./wt. at a purity level of at least 80%.

21. The method according to claim 12 , wherein said mixture contacts an ion exchange resin before contacting said resin material adapted for chromatography.

22. The method according to claim 21 , wherein said contacting with said ion exchange resin is performed either in a single step by contacting a mixed-bed acid/base resin, or in two steps by contacting an acid resin first, then base resin second or the reverse with base resin first and then acid resin second.

Assignees

• Archer Daniels Midland Co

Inventors

• Smith Brennan
• Ma Chicheng

Classifications

• C07D307/20

  Oxygen atoms · CPC title

• B01D15/361

  Ion-exchange · CPC title

• C07C29/76 Primary

  by physical treatment · CPC title

• B01D15/185

  characterised by the components to be separated · CPC title

• C07C29/58

  by elimination of halogen, e.g. by hydrogenolysis, splitting-off (C07C29/124 takes precedence) · CPC title