2,5-furan dicarboxylate derivatives, and use thereof as plasticizers
View Patent ↗The invention relates to mixtures of isononyl furan-2,5-dicarboxylate of formula (I), methods for producing said mixtures of isononyl furan-2,5-dicarboxylate of formula (I), compositions containing mixtures of isononyl furan-2,5-dicarboxylate of formula (I), uses of the mixtures of isononyl furan-2,5-dicarboxylate of formula (I) as plasticizers, and uses of the aforementioned compositions containing isononyl furan-2,5-dicarboxylate of formula (I).
1. A mixture, comprising:
isomeric nonyl esters of a furan-2,5-dicarboxylic acid of formula I:
2. The mixture of claim 1 , comprising at least two nonyl esters, which comprise different isomeric C9 radicals,
wherein no C9 radical in the mixture has a fraction of more than 90 mol %.
3. A process for preparing the mixture of claim 1 , the process comprising:
contacting furan-2,5-dicarboxylic acid with a mixture comprising isomeric C9 alcohols in the presence of at least one catalyst selected from the group consisting of a Brønsted acid and a Lewis acid, thereby liberating water;
wherein the isomeric C9 alcohols are in a molar excess of up to 50%.
4. A process for preparing the mixture of claim 1 , the process comprising:
a) chlorinating furan-2,5-dicarboxylic acid, to obtain furan-2,5-dicarbonyl chloride;
b) isolating and purifying the furan-2,5-dicarbonyl chloride; and then
c) contacting the furan-2,5-dicarbonyl chloride with a mixture comprising isomeric C9 alcohols, thereby liberating hydrogen chloride.
5. A process for preparing the mixture of claim 1 , the process comprising:
contacting dimethyl furan-2,5-dicarboxylate with a mixture comprising isomeric C9 alcohols, in the presence of at least one catalyst selected from the group consisting of a Brønsted acid and a Lewis acid, thereby liberating methanol.
6. A composition, comprising:
the mixture of claim 1 ; and
at least one plasticizer selected from the group consisting of an alkyl benzoate, a dialkyl adipate, a glycerol ester , a trialkyl ester of citric acid, an acylated trialkyl ester of citric acid, a trialkyl trimellitate, a glycol dibenzoate, a dialkyl terephthalate, a dialkyl phthalate, a dialkanoyl ester of isosorbide, and a dialkyl ester of a 1,2-, 1,3-, or 1,4-cyclohexanedicarboxylic acid.
7. The composition of claim 6 , wherein a molar ratio of the mixture to the plasticizer is in a range from 1:15 to 15:1.
8. The composition of claim 7 , further comprising:
at least one polymer selected from the group consisting of polyvinyl chloride, polyvinylbutyral, polylactic acid, polyhydroxybutyral, and polyalkyl methacrylate.
9. A composition, comprising:
the mixture of claim 1 ; and
at least one polymer selected from the group consisting of polyvinyl chloride, polyvinylbutyral, polylactic acid, polyhydroxybutyral, and polyalkyl methacrylate.
10. The composition of claim 9 , wherein a ratio of the polymer to the mixture is in a range from 30:1 to 1:2.5.
11. A process for plasticizing a plastic, the process comprising:
contacting the mixture of claim 1 with a plastic.
12. A process for plasticizing a paint, an ink, an adhesive, an adhesive component, a varnish, a plastisol, or a sealant, the process comprising:
contacting the composition of claim 6 with a paint, an ink, an adhesive, an adhesive component, a varnish, a plastisol, or a sealant.
13. A process for dissolving a paint, an ink, an adhesive, an adhesive component, a varnish, a plastisol, or a sealant, the process comprising:
contacting the composition of claim 6 with a paint, an ink, an adhesive, an adhesive component, a varnish, a plastisol, or a sealant.
14. A lubricating oil, comprising:
the composition of claim 6 .
15. A metal processing auxiliary, comprising:
the composition of claim 6 .
16. The process of claim 3 , wherein the isomeric C9 alcohols have an empirical formula of C 9 H 19 OH.
17. The process of claim 3 , wherein the isomeric C9 alcohols have an empirical formula of C 8 H 17 CH 2 OH.
18. The process of claim 17 , wherein the mixture comprising isomeric C9 alcohols comprises less than 10 mol % of 3,5,5-trimethylhexanol or a trisubstituted nonyl alcohol of empirical formula C 8 H 17 CH 2 OH.
19. The process of claim 17 , wherein the mixture comprising isomeric C9 alcohols comprises less than 5 mol % of 3,5,5-trimethylhexanol or a trisubstituted nonyl alcohol of empirical formula C 8 H 17 CH 2 OH.
20. The process of claim 17 , wherein the mixture comprising isomeric C9 alcohols comprises less than 1 mol % of 3,5,5-trimethylhexanol or a trisubstituted nonyl alcohol of empirical formula C 8 H 17 CH 2 OH.