Process for concentrating azelaic acid

• US 5,973,173 A
• Filed: 04/22/1997
• Issued: 10/26/1999
• Est. Priority Date: 05/26/1995
• Status: Expired due to Fees

• Current Assignee: Cognis Deutschland GmbH & Co. KG (BASF SE)
• Original Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Inventors: Gaige, Dennis G., Johannisbauer, Wilhelm, Josten, Horst, Lindemann, Manfred, McVay, Kenneth R.
• Primary Examiner(s): Carr, Deborah D.
• Application Number:
  US08/844,804
• Time in Patent Office: 917 Days
• Field of Search: 584/181, 584/182, 584/183, 584/204, 584/207, 584/132, 584/206, 584/133, 203/98
• US Class Current: 554/207
• CPC Class Codes: C07C 51/083 from carboxylic acid anhydrides
• CPC Class Codes: C07C 51/44 by distillation
• CPC Class Codes: C07C 55/18 Azelaic acid

Abstract

Pure azelaic acid is obtained by working up a reaction mixture containing C_1-18 monocarboxylic acids, mainly pelargonic acid, and C_4-16 dicarboxylic acids, mainly azelaic acid, obtained from the ozonolysis of oleic acid or a starting mixture containing oleic acid. All but <2% by weight of the monocarboxylic acids and part of the dicarboxylic acids with a chain length of <C₉ and >C₉ are separated off to obtain a prepurified product containing more than 75% by weight of oleic acid and the prepurified product is concentrated to more than 90% by weight of oleic acid in several process steps. In a first process step (1), the dicarboxylic acids with chain lengths of <C₉ present in the prepurified product are removed as first runnings by fractional distillation. In a second process step (2), the bottom product obtained is reacted with water to split carboxylic anhydrides present in the bottom product. In a third process step (3), the reaction mixture is subjected to overhead distillation. The third process step (3) is carried out after or at the same time as the second process step (2). The product yield is improved. The process is particularly suitable for working on an industrial scale.

Claims

1. A process for the production of purified azelaic acid by working up a reaction mixture containing C_1-18 monocarboxylic acids, comprising pelargonic acid, and C_4-16 dicarboxylic acids, comprising azelaic acid, obtained from the ozonolysis of oleic acid or a starting mixture containing oleic acid, all but <

2% by weight of the monocarboxylic acids and part of the dicarboxylic acids with a chain length of <

C₉ and >

C₉ being separated off to obtain a prepurified product containing more than 75% by weight of oleic acid and the prepurified product being concentrated to more than 90% by weight of oleic acid in several process steps of which the last is an overhead distillation step, which comprises;

(1), removing the dicarboxylic acids with chain lengths of <

C₉, present in the prepurified product, as an overhead product by a first fractional distillation;

(2), reacting a bottom product from the first distillation with water to split carboxylic anhydrides present in the bottom product to form a reaction mixture and, (3), distilling the reaction mixture to recover as an overhead product the purified azelaic acid, the third process step (3) being carried out after or at the same time as the second process step (2).

2. The process as claimed in claim 1, wherein process steps (1) and (3) are each carried out in a fractionating column under a head pressure of 1 to 30 mbar.

3. The process as claimed in claim 1 wherein a falling-film evaporator is used as the bottom heater in the fractionating column for the first process step (1).

4. The process as claimed in claim 1 wherein a bottom heater in the third step distillation is selected from the group consisting of a wiped-film evaporators and falling-film evaporators.

5. The process as claimed in claim 1 wherein the second process step (2) is carried out in a stirred tank reactor, or in a static mixer.

6. The process as claimed in claim 1 wherein the bottom product obtained in the first process step (1) is fed directly into a third step fractionating column and, steam is introduced into the column to carry out the second process step.

7. The process as claimed in claim 6, wherein the bottom product obtained in the first process step (1) is introduced approximately in the middle of the third step fractionating column while superheated steam, is introduced into an evaporator of the third step fractionating column.

8. The process as claimed in claim 2 wherein a falling-film evaporator is used as the bottom heater in the fractionating column for the first process step (1).

9. The process as claimed in claim 2 wherein a bottom heater in the third step distillation is selected from the group consisting of a wiped-film evaporators and falling-film evaporators.

10. The process as claimed in claim 2 wherein the second process step (2) is carried out in a stirred tank reactor, or in a static mixer.

11. The process as claimed in claim 2 wherein the bottom product obtained in the first process step (1) is fed directly into a third step fractionating column and, steam is introduced into the column to carry out the second process step.

12. The process as claimed in claim 11, wherein the bottom product obtained in the first process step (1) is introduced approximately in the middle of the third step fractionating column while superheated steam, is introduced into an evaporator of the third step fractionating column.

13. The process as claimed in claim 3 wherein a bottom heater in the third step distillation is selected from the group consisting of a wiped-film evaporators and falling-film evaporators.

14. The process as claimed in claim 3 wherein the second process step (2) is carried out in a stirred tank reactor, or in a static mixer.

15. The process as claimed in claim 3 wherein the bottom product obtained in the first process step (1) is fed directly into a third step fractionating column and, steam is introduced into the column to carry out the second process step.

16. The process as claimed in claim 15, wherein the bottom product obtained in the first process step (1) is introduced approximately in the middle of the third step fractionating column while superheated steam, is introduced into an evaporator of the third step fractionating column.

17. The process as claimed in claim 4 wherein the second process step (2) is carried out in a stirred tank reactor, or in a static mixer.

18. The process as claimed in claim 4 wherein the bottom product obtained in the first process step (1) is fed directly into a third step fractionating column and, steam is introduced into the column to carry out the second process step.

19. The process as claimed in claim 18, wherein the bottom product obtained in the first process step (1) is introduced approximately in the middle of the third step fractionating column while superheated steam, is introduced into an evaporator of the third step fractionating column.

20. The process as claimed in claim 5 wherein the bottom product obtained in the first process step (1) is fed directly into a third step fractionating column and, steam is introduced into the column to carry out the second process step.

21. The process of claim 1 wherein the azelaic acid is obtained from ozonolysis of oleic acid without a prior crystallization step.

22. In a process for recovery of azelaic acid wherein azelaic acid is heated during the process and a composition containing a high boiling point anhydride of azelaic acid is formed, the improvement which comprises:

contacting the composition with water or steam to form a mixture containing azelaic acid and a reduced content of the anhydride of azelaic acid and recovering at least a portion of the azelaic acid.

23. The process of claim 22 wherein the azelaic acid is recovered by distillation.

24. The process of claim 22 wherein the composition containing the anhydride of azelaic acid is formed in the reboiling section of a distillation column.