Dianhydrohexitol diester mixture GC

• US 9,493,632 B2
• Filed: 12/19/2012
• Issued: 11/15/2016
• Est. Priority Date: 12/21/2011
• Status: Active Grant

• Current Assignee: Evonik Degussa GmbH
• Original Assignee: Evonik Degussa GmbH
• Inventors: Grass, Michael, Gevers, Andreas, Woldt, Benjamin, Woelk-Faehrmann, Michael
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): Grinsted, Ronald
• Application Number:
  US14/367,636
• Publication Number:
  US 20150152245A1
• Time in Patent Office: 1,427 Days
• Field of Search: 524/284
• US Class Current: 1/1
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C08K 5/1535 Five-membered rings

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 proportion of C8 based on the sum of C8 and C10 in the overall ester mixture is 45 mol % to 85 mol %.

Claims

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

2. The ester mixture according to claim 1, wherein the proportion of the C8-acyl groups relative to the total sum of the C8-acyl groups and the C10-acyl groups in the ester mixture is from 50 mol % to 75 mol %.

3. The ester mixture according claim 1, wherein the proportion of the C8-acyl groups relative to the total sum of the C8-acyl groups and the C10-acyl groups in the ester mixture is from 50 mol % to 65 mol %.

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

5. The ester mixture according to claim 1, wherein R¹ is selected from the group consisting of

a C8-acyl group derived from a C8-alkyl linear carboxylic acid, and

a C10-acyl group derived from a C10-alkyl linear carboxylic acid.

6. The ester mixture according to claim 1, wherein R² is selected from the group consisting of

a C8-acyl group derived from a C8-alkyl linear carboxylic acid, and

a C10-acyl group derived from a C10-alkyl linear carboxylic acid.

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

8. A composition, comprising:

the ester mixture of claim 1; and

a high boiler, a low boiler, or a mixture thereof.

9. The composition according to claim 8, wherein a proportion of high boilers 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 low boilers is less than 4.5 area % based on the 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 method of plasticizing a polymer, the method comprising combining the ester mixture of claim 1 with a polymer.

13. A method for producing an ester mixture of claim 1, comprising:

a) admixing n-octanoic acid and n-decanoic acid with a dianhydrohexitol;

b) esterifying the n-octanoic acid and the n-decanoic acid with the dianhydrohexitol in the presence of a catalyst; and

c) terminating the esterifying b) 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 admixed in a molar ratio from 85:

15 and 45;

55.

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

20 and 45;

55.

17. The ester mixture according to claim 1, wherein at least one R¹ or R² 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.