Method of making internal dehydration products of sugar alcohols

Patent metadata

Field	Value
Publication number	US-9315515-B2
Application number	US-201314437258-A
Country	US
Kind code	B2
Filing date	Oct 4, 2013
Priority date	Oct 31, 2012
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

A process is provided for making isohexides such as isosorbide with reduced color and/or improved color stability on storage, wherein ionic species in the crude dehydration product mixture are chromatographically substantially separated from the remainder of the crude product mixture, then the remainder is refined to yield a finished product for further use or sale.

First claim

The invention claimed is:

1. A process for making an isohexide, comprising:
dehydrating a hexitol in the presence of an acid catalyst to form a crude dehydration product mixture including an isohexide from the hexitol;
chromatographically substantially separating ionic species from the crude dehydration product mixture; then
subjecting the remainder to further processing to yield a product enriched in the isohexide compared to the remainder.

2. A process according to claim 1 , wherein a residual following the dehydration, chromatographic separation and further processing steps, containing unconverted hexitol, one or more monodehydrated materials from the hexitol or both unconverted and monodehydrated materials is recycled to the dehydrating step.

3. A process according to claim 1 , further comprising adding at least one antioxidant to the remainder before the further processing.

4. A process according to either claim 1 or claim 3 , further comprising hydrogenating one or both of the remainder of the crude dehydration product mixture and the product enriched in the isohexide with a source of hydrogen in the presence of a catalyst.

5. A process according to claim 1 , wherein ionic species are separated at least in part by ion exclusion chromatography with at least one strong acid cation exchange resin in the cation form corresponding to the highest concentration cation among ionic species in the dehydration product mixture.

6. A process according to claim 1 , wherein ionic species are separated at least in part by ion exchange chromatography with a combination of at least one highly crosslinked strong acid cation exchange resin and at least one highly crosslinked strong base anion exchange resin.

7. A process according to claim 1 , further comprising contacting the remainder with at least one adsorbent.

8. A process according to claim 7 , wherein the at least one adsorbent includes an activated carbon adsorbent.

9. A process according to claim 1 , wherein the crude dehydration product mixture passes through at least one nanofiltration or ultrafiltration membrane before being chromatographically processed.

Assignees

• Archer Daniels Midland Co

Inventors

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

Classifications

• A61K31/34

  having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title