Additives for improved isohexide products

Patent metadata

Field	Value
Publication number	US-9266900-B2
Application number	US-201314437269-A
Country	US
Kind code	B2
Filing date	Oct 4, 2013
Priority date	Oct 31, 2012
Publication date	Feb 23, 2016
Grant date	Feb 23, 2016

Abstract

Reduced color and improved color stability isohexide products are enabled through adding one or more antioxidants to a crude dehydration product mixture from an acid-catalyzed dehydration of a corresponding hexitol.

First claim

The invention claimed is:

1. A distillable composition of matter comprised of a) a crude dehydration product mixture from an acid-catalyzed dehydration of one or more hexitols which mixture includes at least an isohexide, and b) one or more antioxidant additives, at least one of which possesses sufficient volatility to at least partially co-distill with the isohexide on a distillation of the composition and is soluble in the isohexide under room temperature conditions.

2. A distillable composition according to claim 1 , wherein at least 50 percent of the one or more antioxidant additives on a mass basis can be made to co-distill with the isohexide distillate using a wiped film evaporator.

3. A distillable composition according to claim 1 , wherein the crude dehydration product is from an acid-catalyzed dehydration of sorbitol to make isosorbide, and the one or more antioxidant additives are selected from the group consisting of hindered phenols containing one or more methoxyl groups but no other functional groups other than alkyl groups, and mixtures of any of these.

4. A distillable composition according to claim 3 , wherein the one or more antioxidant additives are selected from di-tert-butyl-4-methoxyphenol; butylated hydroxyanisole; 2,6-dimethoxy-4-methylphenol; 2,6-dimethoxyphenol and mixtures of any of these.

5. A distillable composition according to claim 4 , wherein the one or more antioxidant additives comprise one or both of butylated hydroxyanisole and 2,6-dimethoxy-4-methylphenol.

6. A 100% molten isohexide-enriched product including one or more antioxidants selected from the group consisting of hindered phenols containing one or more methoxyl groups but no other functional groups other than alkyl groups, and mixtures of any of these, and having an initial APHA color according to ASTM D1209 as manufactured of 100 or less.

7. A 100% molten isohexide-enriched product according to claim 6 , having an initial APHA color of 20 or less.

8. A 100% molten isohexide-enriched product according to claim 7 , having an initial APHA color of 15 or less.

9. A 100% molten isohexide-enriched product according to claim 8 , having an initial APHA color of 10 or less.

10. An 85% solution isohexide product including one or more antioxidants selected from the group consisting of hindered phenols containing one or more methoxyl groups but no other functional groups other than alkyl groups, and mixtures of any of these, and having an initial APHA color according to ASTM D1209 as manufactured of 100 or less.

11. An 85% solution isohexide product according to claim 10 , having an initial APHA color of 20 or less.

12. An 85% solution isohexide product according to claim 11 , having an initial APHA color of 15 or less.

13. An 85% solution isohexide product according to claim 12 , having an initial APHA color of 10 or less.

14. A 100% molten isohexide-enriched product according to any one of claims 6 through 9 , which after accelerated aging at 85 degrees Celsius for four weeks demonstrates an APHA color of 200 or less.

15. An 85% solution isohexide-enriched product according to any one of claims 10 through 13 , which after accelerated aging at 85 degrees Celsius for four weeks demonstrates an APHA color of 250 or less.

16. 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 comprising an isohexide;
adding one or more antioxidants to the crude dehydration product mixture, at least one of which possesses sufficient volatility to at least partially co-distill with the isohexide on a distillation of the crude dehydration product mixture and is soluble in the isohexide under room temperature conditions; and
distilling the crude dehydration product mixture containing the one or more antioxidants to yield an isohexide product including one or more antioxidants.

17. A process according to claim 16 , further comprising contacting the crude dehydration product mixture with one or more ion exchange resins, with one or more ion exclusion resins or with both ion exchange and ion exclusion resins.

Assignees

• Archer Daniels Midland Co

Inventors

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

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• A61K31/34

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