Process for preparing triacetonamine

Patent metadata

Field	Value
Publication number	US-11731940-B2
Application number	US-202117238715-A
Country	US
Kind code	B2
Filing date	Apr 23, 2021
Priority date	May 7, 2020
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

An improved process can be used for preparing triacetonamine. The process involves performing an absorption step in which acetone present in the crude product is removed from triacetonamine by distillation, and in gaseous form is then absorbed in countercurrent into fresh, liquid acetone. The acetone stream thus obtained is then converted further to triacetonamine. This process enables more energy-efficient reutilization of the unreacted reactants used in the synthesis of triacetonamine, and thus lowers overall both the use of reactants and the energy expenditure.

First claim

The invention claimed is:

1. A process for preparing triacetonamine, the process comprising:
(a) reacting an acetone stream S Ac1 and an ammonia stream S Am1 in the presence of a catalyst K1 to give a crude product stream S RP1 comprising triacetonamine and acetone,
(b) performing an at least partial removal by distillation of acetone from S RP1 to obtain a gaseous stream S Ac2 comprising acetone,
(c) performing an at least partial absorption of the gaseous stream S Ac2 in countercurrent into a liquid acetone stream S Ac3 to obtain a liquid acetone stream S Ac4 ,
(d) repeating (a), wherein the acetone stream S Ac4 is used as the acetone stream S Ac1 .

2. The process according to claim 1 , wherein the at least partial removal by distillation of acetone from S RP1 which takes place in (b) is performed in a distillation column.

3. The process according to claim 1 , wherein a temperature range used in the at least partial removal by distillation in (b) is below the boiling point of triacetonamine.

4. The process according to claim 1 , wherein, prior to and/or during the at least partial removal by distillation of acetone from the crude product stream S RP1 as per (b), water is added to the crude product stream S RP1 ,
wherein the crude product stream S RP1 comprises by-products, and
wherein at least one of the by-products in the crude product stream S RP1 selected from the group consisting of phorone, diacetone alcohol, diacetonamine, acetonin, and isophorone, is at least partially reacted with water so that at least one of the by-products in crude product stream S RP1 is at least partially cleaved into acetone.

5. The process according to claim 1 , wherein (a) is carried out at a temperature of 20° C. to 180° C.

6. The process according to claim 1 , wherein a molar ratio of acetone used in (a) to ammonia used in (a) is 3:1 to 20:1.

7. The process according to claim 1 , wherein the catalyst K1 is a heterogeneous catalyst.

8. The process according to claim 1 , wherein in (c) a portion of the acetone in the gaseous stream S Ac2 obtained in (b) is absorbed into the liquid acetone stream S Ac3 and the remaining portion is condensed.

9. The process according to claim 1 , wherein said process is performed continuously.

10. The process according to claim 1 , wherein a reaction time in (a) is 5 to 7 hours.

11. The process according to claim 1 , wherein a volume space velocity for ammonia in (a) is 0.03 to 5.25 h −1 .

12. The process according to claim 1 , wherein a volume space velocity for acetone in (a) is 0.66 to 1.174 h −1 .

13. The process according to claim 1 , wherein a temperature in (a) is 60 to 90° C.

14. The process according to claim 1 , wherein pressure in (a) is 7 to 14 bar.

15. The process according to claim 1 , wherein 1% to 99% by weight of said acetone in said gaseous stream S Ac2 obtained in (b) is condensed and a remainder of said acetone in said gaseous stream S Ac2 is absorbed in counter current into said liquid acetone stream S Ac3 .

16. The process according to claim 1 , wherein (C) is carried out in a gas scrubber.

17. The process according to claim 1 , wherein gaseous stream S Ac2 has a temperature of form 57° C. to 100° C.

18. The process according to claim 1 , wherein said liquid acetone stream S Ac3 has a temperature which is at least 10° C. below the boiling point of said acetone at a respective pressure.

19. The process according to claim 1 , wherein said liquid acetone stream S Ac3 has a temperature in a range from 10° to 15° C.

Assignees

• Evonik Operations Gmbh

Inventors

• Minke Katharina
• Graskamp Holger

Classifications

• C07D211/74 Primary

  Oxygen atoms · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title