Process for preparing dialkyl 1,4-cyclohexanedicarboxylates

Patent metadata

Field	Value
Publication number	US-11845849-B2
Application number	US-202117385323-A
Country	US
Kind code	B2
Filing date	Jul 26, 2021
Priority date	Jul 28, 2020
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

A process prepares dialkyl 1,4-cyclohexanedicarboxylates by ring hydrogenation of the corresponding dialkyl terephthalate having a CO value of less than 0.3 mg KOH/g. The dialkyl 1,4-cyclohexanedicarboxylates thus produced can be used as plasticizers or as a component of a plasticizer composition for plastics, in particular PVC.

First claim

The invention claimed is:

1. A process for preparing dialkyl 1,4-cyclohexanedicarboxylate in which the two alkyl groups both have at least 2 carbon atoms, the process comprising:
carrying out a ring hydrogenation of a dialkyl terephthalate in which the two alkyl groups both have at least 2 carbon atoms, in the presence of a heterogeneous hydrogenation catalyst, with a hydrogen-containing gas, to form the dialkyl 1,4-cyclohexanedicarboxylate,
wherein the dialkyl terephthalate in the ring hydrogenation has a CO value of less than 0.3 mg KOH/g.

2. The process according to claim 1 , wherein each of the two alkyl groups of the dialkyl 1,4-cyclohexanedicarboxylate have 3 to 10 carbon atoms.

3. The process according to claim 1 , wherein the dialkyl terephthalate in the ring hydrogenation is prepared by transesterification of dimethyl terephthalate with an alcohol having at least 2 carbon atoms, or by esterification of terephthalic acid with an alcohol having at least 2 carbon atoms.

4. The process according to claim 3 , wherein the alcohol in the transesterification or in the esterification is an alcohol having 3 to 10 carbon atoms.

5. The process according to claim 2 , wherein the dialkyl 1,4-cyclohexanedicarboxylate is diisononyl 1,4-cyclohexanedicarboxylate or di-2-ethylhexyl 1,4-cyclohexanedicarboxylate.

6. The process according to claim 1 , wherein the heterogeneous hydrogenation catalyst in the ring hydrogenation comprises a transition metal on a support material.

7. The process according to claim 6 , wherein the transition metal is a metal of group 8 of the periodic table of the elements.

8. The process according to claim 6 , wherein the support material is selected from the group consisting of activated carbon, silicon carbide, aluminium oxide, silicon dioxide, aluminosilicate, titanium dioxide, zirconium dioxide, magnesium oxide, zinc oxide, and mixtures thereof.

9. The process according to claim 8 , wherein the support material is titanium dioxide or aluminium oxide.

10. The process according to claim 6 , wherein a transition metal content in the heterogeneous hydrogenation catalyst is within a range from 0.1% to 10% by weight.

11. The process according to claim 1 , wherein the ring hydrogenation is carried out in at least one hydrogenation unit.

12. The process according to claim 1 , wherein a hydrogenation temperature in the ring hydrogenation is within a range from 50 to 250° C.

13. The process according to claim 1 , wherein the ring hydrogenation is carried out within a pressure range from 3 to 300 bar.

14. The process according to claim 1 , wherein each of the two alkyl groups of the dialkyl 1,4-cyclohexanedicarboxylate have at least 4 carbon atoms.

15. The process according to claim 1 , wherein the dialkyl terephthalate in the ring hydrogenation has a CO value of less than 0.1 mg KOH/g.

16. The process according to claim 2 , wherein each of the two alkyl groups of the dialkyl 1,4-cyclohexanedicarboxylate have 9 carbon atoms.

17. The process according to claim 7 , wherein the transition metal is ruthenium.

18. The process according to claim 11 , wherein the ring hydrogenation is carried out in at least two hydrogenation units connected in series, wherein at least one of the at least two hydrogenation units is operated in loop mode.

19. The process according to claim 1 , wherein a hydrogenation temperature in the ring hydrogenation is within a range from 80 to 200° C. and ring hydrogenation is carried out within a pressure range from 50 to 200 bar.

Assignees

• Evonik Operations Gmbh

Inventors

• Kraft Johannes
• Altmann Lena
• Anton Johan
• Grass Michael
• Schneider Thomas

Classifications

• C08K5/12 Primary

  of cyclic polycarboxylic acids · CPC title

• B01J21/063

  Titanium; Oxides or hydroxides thereof · CPC title

• B01J23/462

  Ruthenium · CPC title

• C07C51/36

  by hydrogenation of carbon-to-carbon unsaturated bonds · CPC title

• C09D7/63

  organic · CPC title