Hydrogenation of isohexide products for improved color

Patent metadata

Field	Value
Publication number	US-9321784-B2
Application number	US-201314437266-A
Country	US
Kind code	B2
Filing date	Oct 4, 2013
Priority date	Oct 31, 2012
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

A process is described for making isohexides, comprising dehydrating one or more hexitols with an acid catalyst to form a crude dehydration product mixture including one or more isohexides, further processing the mixture to separate out one or more fractions of a greater purity or higher concentration of at least one of the isohexides, and hydrogenating at least one of a) the crude dehydration product mixture, b) a neutralized crude dehydration product mixture, following a neutralization of the crude dehydration product mixture, c) the product mixture following a neutralization step and further following a step to remove ionic species therefrom, d) a greater purity or higher concentration fraction, and e) a lesser purity or concentration fraction, by reaction with a hydrogen source in the presence of a hydrogenation catalyst. Hydrogenation improves the color and/or color stability of the material, especially of a finished isohexide product.

First claim

The invention claimed is:

1. A process for making one or more isohexides, comprising:
dehydrating one or more hexitols in the presence of an acid catalyst to form a crude dehydration product mixture including one or more isohexides;
after the dehydration step, further processing the crude dehydration product mixture to separate out one or more fractions of a greater purity or higher concentration of at least one of the isohexides in the crude dehydration product mixture and one or more fractions of a lesser purity or concentration; and
hydrogenating one or both of
a greater purity or higher concentration fraction and
a lesser purity or concentration fraction following the further processing of the crude dehydration product mixture,

by reaction with a hydrogen source in the presence of a hydrogenation catalyst, under conditions effective to carry out the hydrogenation.

2. The process according to claim 1 , wherein the further processing includes distillation, and further wherein a bottoms product from the distillation is hydrogenated.

3. The process according to claim 1 , wherein the further processing includes distillation, and further wherein a greater purity or higher concentration fraction is hydrogenated.

4. The process according to claim 3 , wherein the further processing includes thin film or short path distillation.

5. The process according to claim 2 , wherein the further processing includes thin film or short path distillation.

6. The process according to claim 1 , further comprising the step of removing ionic species from the crude dehydration product mixture prior to the further processing step, by contacting the crude dehydration product mixture with one or more ion exchange resins, through ion exclusion means or through a combination of ion exchange and ion exclusion means.

7. The process according to claim 2 , further comprising the step of removing ionic species from the crude dehydration product mixture prior to the further processing step, by contacting the crude dehydration product mixture with one or more ion exchange resins, through ion exclusion means or through a combination of ion exchange and ion exclusion means.

8. The process according to claim 7 , wherein the further processing includes thin film or short path distillation.

9. The process according to claim 3 , further comprising the step of removing ionic species from the crude dehydration product mixture prior to the further processing step, by contacting the crude dehydration product mixture with one or more ion exchange resins, through ion exclusion means or through a combination of ion exchange and ion exclusion means.

10. The process according to claim 9 , wherein the further processing includes thin film or short path distillation.

11. The process of claim 1 , wherein the acid catalyst is a soluble acid catalyst.

Assignees

• Archer Daniels Midland Co
• Archer Daniels Midland Co

Inventors

• Hagberg Erik
• Rockafellow Erin M
• Smith Brennan
• Stensrud Kenneth F

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title