Dianhydrohexitol diester mixture NMR

Patent metadata

Field	Value
Publication number	US-9505909-B2
Application number	US-201214367730-A
Country	US
Kind code	B2
Filing date	Dec 19, 2012
Priority date	Dec 21, 2011
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

An ester mixture of dianhydrohexitol, a composition comprising the ester mixture and a polymer composition comprising the ester mixture or the composition, the use thereof, and a process by which the ester mixture can be prepared, where the ester mixture has a mean chain length of (8.3) to (9.2).

First claim

The invention claimed is:

1. An ester mixture, comprising a compound of formula (I):

wherein:
R 1 and R 2 independently represent a C8-acyl group or a C10-acyl group, in which
the C8-acyl group is derived from a C8-alkyl linear carboxylic acid, a C8-alkyl branched carboxylic acid, or a C8-alkene carboxylic acid that may be partially or completely epoxidized, and
the C10-acyl group is derived from a C10-alkyl linear carboxylic acid, a C10-alkyl branched carboxylic acid, or a C10-alkene carboxylic acid that may be partially or completely epoxidized; and

the ester mixture has a mean chain length of from 8.4 to 9.2.

2. The ester mixture according to claim 1 , wherein the ester mixture has a mean chain length of from 8.4 to 9.1.

3. The ester mixture according to claim 1 , wherein the ester mixture has a mean chain length of from 8.5 to 9.1.

4. The ester mixture according to claim 1 , wherein a sum of C8-acyl groups and C10-acyl groups in the ester mixture has a proportion of above 50 mol % relative to all acid chains in the ester mixture.

5. The ester mixture according to claim 1 , wherein R 1 is a C8-acyl group derived from a C8-alkyl linear carboxylic acid or a C10-acyl group derived from a C10-alkyl linear carboxylic acid.

6. The ester mixture according to claim 1 , wherein R 2 is a C8-acyl group derived from a C8-alkyl linear carboxylic acid or a C10-acyl group derived from a C10-alkyl linear carboxylic acid.

7. The ester mixture according to claim 1 , comprising a mixture of the following three compounds:

8. A composition, comprising:
the ester mixture of claim 1 ; and
at least one of a high boiler and a low boiler.

9. The composition according to claim 8 , wherein a proportion of the high boiler is less than 15 area % based on ester signals in a gas-chromatographic analysis of the composition.

10. The composition according to claim 8 , wherein a proportion of the low boiler is less than 4.5 area % based on ester signals in a gas-chromatographic analysis of the composition.

11. A polymer composition, comprising:
the ester mixture of claim 1 ; and
a polymer.

12. A plasticizer, comprising the ester mixture of claim 1 .

13. A method for producing an ester mixture of claim 1 , comprising:
mixing n-octanoic acid and n-decanoic acid, thereby obtaining an acid mixture
esterifying the acid mixture with a dianhydrohexitol in the presence of at least one catalyst; and
terminating the esterifying when a proportion of monoester of the dianhydrohexitol is below 2.0 area % based on a gas-chromatographic analysis.

14. The method according to claim 13 , wherein the catalyst is hypophosphorous acid.

15. The method according to claim 13 , wherein the n-octanoic acid and the n-decanoic acid are mixed in a molar ratio of from 85:15 to 45:55.

16. The method according to claim 13 , wherein the n-octanoic acid and the n-decanoic acid are mixed in a molar ratio of from 80:20 to 45:55.

17. The ester mixture according to claim 1 , wherein at least one R 1 or R 2 group contained in a compound of formula (I) in the ester mixture is defined as a C8-alkene carboxylic acid that is partially or completely epoxidized or as a C10-alkene carboxylic acid that is partially or completely epoxidized.

Assignees

• Grass Michael
• Gevers Andreas
• Woldt Benjamin
• Woelk-Faehrmann Michael
• Roquette Freres

Inventors

• Grass Michael
• Gevers Andreas
• Woldt Benjamin
• Woelk-Faehrmann Michael

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C08K5/1535 Primary

  Five-membered rings · CPC title