Process for the isolation of 1,2,5,6-hexanetetrol from sorbitol hydrogenolysis reaction mixtures using simulated moving bed chromatography

Patent metadata

Field	Value
Publication number	US-9732020-B2
Application number	US-201515302411-A
Country	US
Kind code	B2
Filing date	Apr 10, 2015
Priority date	Apr 10, 2014
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

A method of isolating and purifying 1,2,5,6 hexanetetrol (HTO) from a reaction mixture containing HTO and other byproducts of a hydrogenation 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 comprising HTO and other C1-C6 alcohols and polyols with a resin material adapted for chromatography under conditions where HTO preferentially associates with the resin relative to other components in the mixture, and eluting HTO from said resin with a solvent.

First claim

We claim:

1. A method of purifying 1,2,5,6-hexanetetrol (HTO) comprising: contacting a mixture comprising HTO and other C 1 -C 6 alcohols and polyols with a resin material adapted for chromatography, under conditions where HTO preferentially associates with the resin material relative to other components in the mixture; and eluting HTO from said resin material with a solvent.

2. The method according to claim 1 , wherein said mixture is a product of a sugar alcohol hydrogenation.

3. The method according to claim 2 , wherein said sugar alcohol is selected from the group consisting of: sorbitol, mannitol, galactitol, fucitol, iditol, inositol, maltitol, and mixtures thereof.

4. The method according to claim 2 , wherein said sugar alcohol is sorbitol.

5. The method according to claim 1 , wherein said mixture comprises HTO, glycerol, volatile alcohols, sorbitol, water, and ionic species.

6. 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.

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

8. The method according to claim 6 , wherein said resin material has either 1) a Gaussian particle size distribution, or 2) a mono-dispersed particle size.

9. 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.

10. The method according to claim 9 , wherein said resin material has a particle size in a range from about 250 μm to about 500 μm.

11. 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.

12. 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.

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

14. The method according to claim 13 , wherein said yield is at least 75% wt./wt. at a purity level of at least 85%.

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

16. The method according to claim 15 , 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.

17. The method according to claim 15 , wherein a fraction depleted of ions and containing HTO is obtained after contacting with the ion exchange resin and said fraction is concentrated by evaporation.

18. The method according to claim 17 , wherein said evaporation method is selected from the group consisting of vacuum evaporation, thin film evaporation (TFE) and a combination of both vacuum and TFE.

19. The method according to claim 1 , wherein resin material adapted for chromatography is loaded onto a simulated-moving bed (SMB) apparatus, and said SMB apparatus is operated to perform continuous chromatographic separation of HTO.

20. A method of purifying 1,2,5,6 hexanetetrol (HTO) from a reaction mixture comprised of HTO and other byproducts of a hydrogenation reaction of a sugar alcohol comprising:
a) contacting said reaction mixture with a strong acid ion exchange resin to obtain a first eluent fraction depleted of cationic species;
b) contacting said first eluent fraction with a strong basic ion exchange resin to obtain a second eluent fraction depleted of anionic species;
c) evaporating said second eluent fraction under vacuum and retaining a first bottoms fraction depleted of water, volatile alcohols and lower boiling diol;
d) subjecting said first bottoms fraction to a thin film evaporation and retaining a second bottoms fraction depleted of glycerol;
e) contacting said second bottoms fraction with a non-functionalized chromatography resin, wherein the resin is loaded into a simulated moving bed chromatography apparatus;
f) eluting said chromatography resin with deionized water; and
g) collecting a fraction enriched in HTO as compared to said hydrogenation reaction mixture.

Assignees

• Archer Daniels Midland Co

Inventors

• Smith Brennan
• Ma Chicheng

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C07C29/154

  containing copper, silver, gold, or compounds thereof · CPC title

• B01D15/361

  Ion-exchange · CPC title

• B01D15/1821

  Simulated moving beds · CPC title

• B01D3/10

  Vacuum distillation (B01D3/12 takes precedence) · CPC title