Method for producing cis,cis-1,2,4-cyclohexane tricarboxylic acid crystal

Patent metadata

Field	Value
Publication number	US-11021428-B2
Application number	US-201816496593-A
Country	US
Kind code	B2
Filing date	Mar 19, 2018
Priority date	Mar 29, 2017
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

An object of the present invention is to provide a method for producing cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals, from which high purity cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals are obtained. The method for producing cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals of the present invention comprises the following steps: Step 1: measuring a mass ratio (cis/trans ratio) of cis,cis-1,2,4-cyclohexanetricarboxylic acid to trans,trans-1,2,4-cyclohexanetricarboxylic acid in an aqueous starting material solution comprising the cis,cis-1,2,4-cyclohexanetricarboxylic acid to give an aqueous starting material solution for crystal precipitation having a cis/trans ratio of 10 or more; and Step 2: subjecting the aqueous starting material solution for crystal precipitation obtained in step 1 to crystal precipitation.

First claim

The invention claimed is:

1. A method for producing one or more cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals, the method comprising:
selecting and/or adjusting a cis/trans mass ratio of cis,cis-1,2,4-cyclohexanetricarboxylic acid to trans,trans-1,2,4-cyclohexanetricarboxylic acid in an aqueous starting material solution comprising the cis,cis-1,2,4-cyclohexanetricarboxylic acid to obtain a selected aqueous starting material solution for crystal precipitation having a cis/trans ratio of 19.7 or more; and
subjecting the selected aqueous starting material solution to crystal precipitation, to obtain resulting cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals having a purity of 98.8% by mass or more.

2. The method of claim 1 , wherein the subjecting comprises concentrating the selected aqueous starting material solution to obtain a solvent-to-solute mass ratio of the selected aqueous starting material solution in a range of from 0.1 to 5.

3. The method of claim 1 , wherein the cis/trans ratio is 40 or more.

4. The method of claim 1 , wherein the resulting cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals have a purity of 99.0% by mass or more.

5. The method of claim 1 , wherein a recovery rate of cis,cis-1,2,4-cyclohexanetricarboxylic acid in the subjecting is 60% by mass or more, relative to a total 1,2,4-cyclohexanetricarboxylic acid mass.

6. The method of claim 1 , wherein the subjecting comprises adding seed crystals to the selected aqueous starting material solution.

7. The method of claim 6 , wherein the seed crystals are added in an amount of 0.01 to 40% by mass based on cis,cis-1,2,4-cyclohexanetricarboxylic acid contained in the selected aqueous starting material solution.

8. The method of claim 6 , wherein the adding of the seed crystals is carried out at a temperature of the selected aqueous starting material solution in a range of from 1 to 60° C.

9. The method of claim 3 , wherein resulting cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals have a purity of 90% by mass or more.

10. The method of claim 3 , wherein a recovery rate of cis,cis-1,2,4-cyclohexanetricarboxylic acid in the subjecting is 60% by mass or more, relative to a total 1,2,4-cyclohexanetricarboxylic acid mass.

11. The method of claim 3 , wherein the subjecting comprises adding seed crystals to the selected aqueous starting material solution.

12. The method of claim 11 , wherein the seed crystals are added in an amount in a range of from 0.01 to 40% by mass based on cis,cis-1,2,4-cyclohexanetricarboxylic acid contained in the selected aqueous starting material solution.

13. The method of claim 11 , wherein a temperature of the selected aqueous starting material solution when the seed crystals are added is in a range of from 1 to 60° C.

14. The method of claim 1 , wherein the resulting cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals have a purity of 99.1% by mass or more.

15. The method of claim 1 , wherein the cis/trans ratio is 20 or more.

16. The method of claim 1 , wherein the cis/trans ratio is 35 or more.

17. The method of claim 1 , wherein the cis/trans ratio is 45 or more.

18. The method of claim 1 , wherein the cis/trans ratio no more than 1000.

19. The method of claim 3 , wherein the recovery rate of cis,cis-1,2,4-cyclohexanetricarboxylic acid in the subjecting is 65% by mass or more.

20. The method of claim 3 , wherein the recovery rate of cis,cis-1,2,4-cyclohexanetricarboxylic acid in the subjecting is 70% by mass or more.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Saito Shinya
• Kumano Tatsuyuki

Classifications

• C07C51/43 Primary

  by change of the physical state, e.g. crystallisation · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C61/09

  Completely hydrogenated benzenedicarboxylic acids · CPC title

• C07C61/08

  Saturated compounds having a carboxyl group bound to a six-membered ring · CPC title