Dianhydrohexitol diester mixture NMR
View Patent ↗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).
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.