IP Library Granted Patent US 7,256,315
Granted Patent B2
US 7,256,315 · App. 10/524,548 · Granted Aug 14, 2007

Process for the production of 3-methylthiopropanal

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Quick Facts
Patent No.
US 7,256,315
App. No.
10/524,548
Granted
Aug 14, 2007
Kind
B2
Abstract

Process for the Production of 3-methylthiopropanal. A process for the production of 3-methylthiopropanal which reacting reaction medium comprising methyl mercaptan and acrolein in the presence of a catalyst comprising an organic base characterised in that the organic base is a N-alkyl morpholine compound.

Claims (37)

1. A process for the production of 3-methylthiopropanal (MTPA), comprising:

reacting a reaction medium comprising methylmercaptan and acrolein in the presence of a catalyst comprising an acid and an organic base, wherein the organic base is a N-alkyl-morpholine.

2. The process according to claim 1 , wherein the N-alkyl-morpholine is a C 1 to C 6 alkyl-morpholine.

3. The process according to claim 2 , wherein the C 1 to C 6 alkyl-morpholine is methylmorpholine or ethylmorpholine.

4. The process according to claim 1 , wherein the mole ratio of N-alkyl-morpholine to methylmercaptan is from 0.0001 to 0.05.

5. The process according to claim 4 , wherein the mole ratio of N-alkyl-morpholine to methylmercaptan is from 0.001 to 0.01.

6. The process according to claim 1 , wherein the mole ratio of methylmercaptan to acrolein is from 0.9 to 2.

7. The process according to claim 6 , wherein the mole ratio of methylmercaptan to acrolein is from 1 to 1.2.

8. The process according to claim 1 , wherein the acid is an organic acid.

9. The process according to claim 8 , wherein the organic acid is selected from the group consisting of formic acid, acetic acid, propanoic acid, and butanoic acid.

10. The process according to claim 9 , wherein the organic acid is acetic acid.

11. The process according to claim 8 , wherein the mole ratio of N-alkyl-morpholine to organic acid is from 0.1 to 2.

12. The process according to claim 11 , wherein the mole ratio of N-alkyl-morpholine organic acid is from 0 to 1.

13. The process according to claim 1 , wherein the process is carried out at a temperature of from 20 to 70° C.

14. The process according to claim 13 , wherein the process is carried out at a temperature of from 30 to 50° C.

15. The process according to claim 1 , wherein the process is carried out under atmospheric pressure.

16. A process for the production of 2-hydroxy-4-(methylthio)butanenitrile, comprising:

(a) a first step of reacting a reaction medium comprising methylmercaptan and acrolein in the presence of a catalyst comprising an acid and an organic base to produce a product stream comprising 3-methylthiopropanal and said catalyst, wherein the organic base is a N-alkyl-morpholine; and

(b) a second step of reacting said product stream with hydrogen cyanide in the presence of a catlyst.

17. The process according to claim 16 , wherein the N-alkyl-morpholine is a C1 to C6 alkyl-morpholine.

18. The process according to claim 17 , wherein the C1 to C6 alkyl-morpholine is methylmorpholine or ethylmorpholine.

19. The process according to claim 16 , wherein the mole ratio of N-alkyl-morpholine to methylmercaptan in step (a) is from 0.0001 to 0.05.

20. The process according to claim 19 , wherein the mole ratio of N-alkyl-morpholine to methylmercaptan in step (a) is from 0.001 to 0.01.

21. The process according to claim 16 , wherein the mole ratio of methylmercaptan to acrolein in step (a) is from 0.9 to 2.

22. The process according to claim 21 , wherein the mole ratio of methylmercaptan to acrolein in step (a) is from 1 to 1.2.

23. The process according to claim 16 , wherein the acid in step (a) is an organic acid.

24. The process according to claim 23 , wherein the organic acid is selected from the group consisting of formic acid, acetic acid, propanoic acid, and butanoic acid.

25. The process according to claim 24 , wherein the organic acid is acetic acid.

26. The process according to claim 23 , wherein the mole ratio of N-alkyl-morpholine to organic acid in step (a) is from 0.1 to 2.

27. The process according to claim 26 , wherein the mole ratio of N-alkyl-morpholine to organic acid in step (a) is from 0 to 1.

28. The process according to claim 16 , wherein step (a) is carried out at a temperature of from 20 to 70° C.

29. The process according to claim 28 , wherein step (a) is carried out at a temperature of from 30 to 50° C.

30. The process according to claim 16 , wherein step (a) is carried out under atmospheric pressure.

31. A process for the production of 2-hydroxy-4-(methylthio)butanenitrile, comprising:

reacting a reaction medium comprising 3-methylthiopropanal (MTBA) and hydrogen cyanide in the presence of a catalyst comprising an organic base, wherein the organic base is a N-alkyl-morpholine.

32. The process according to claim 31 , wherein the N-alkyl-morpholine is a C 1 to C 6 alkyl-morpholine.

33. The process according to claim 32 , wherein the C 1 to C 6 alkyl-morpholine is methylmorpholine or ethylmorpholine.

Assignments (3)
RELEASE OF PLEDGE AGREEMENT Recorded Apr 4, 2006
From: J.P. MORGAN EUROPE LIMITED
To: ADISSEO IRELAND LIMITED
Reel/Frame 017422/0749 →
PLEDGE AGREEMENT Recorded Sep 15, 2005
From: ADISSEO IRELAND LIMITED
To: J.P. MORGAN EUROPE LIMITED
Reel/Frame 016800/0748 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2005
From: REY, PATRICK
To: ADISSEO IRELAND LTD. IFSC
Reel/Frame 016219/0597 →