Storage-stable form of 3-methylthiopropionaldehyde

Patent metadata

Field	Value
Publication number	US-11524936-B2
Application number	US-201917282897-A
Country	US
Kind code	B2
Filing date	Nov 21, 2019
Priority date	Nov 21, 2018
Publication date	Dec 13, 2022
Grant date	Dec 13, 2022

Abstract

A chemical compound of formula (I),

and specific compositions including 3-methylthiopropionaldehyde, 3-methylthiopropane-1,1-diol, a compound of formula I and water, and processes for producing same and also the use of same may be used for the production of 2-hydroxy-4-(methylthio)butyronitrile, methionine hydantoin, methionine. Protected forms may be used for the storage and/or transport of 3-methylthiopropionaldehyde.

First claim

The invention claimed is:

1. A composition, comprising:
3 methylthiopropionaldehyde, in a range of from 40 to 95 wt. %;
3 methylthiopropane-1,1-diol, in a range of from 1 to 20 wt. %;
a compound of formula (I), in a range of from 2 to 25 wt. %;

and
water, in a range of from 2.5 to 25 wt. %.

2. The composition of claim 1 , comprising:
the 3-methylthiopropionaldehyde, in a range of from 40 to 94.5 wt. %.

3. The composition of claim 1 , comprising:
the 3-methylthiopropionaldehyde, in a range of from 40 to 92 wt. %; and
the water, in a range of from 5 to 10 wt. %.

4. A method of storing and/or transporting 3-methylthiopropionaldehyde, the method comprising:
contacting the composition of claim 1 , 3-methylthiopropane-1,1-diol, or the compound of formula (I), with the 3-methylthiopropionaldehyde.

5. The method of claim 4 , conducted at a temperature in a range of from 0 to 60° C., for a period of time of up to 12 months.

6. The method of claim 5 , conducted at a temperature in a range of from 5 to 40° C.

7. The method of claim 5 , conducted for a period of time of up to 8 months.

8. The method of claim 5 , conducted for a period of time of up to 4 months.

9. A method for producing the composition of claim 1 , the method comprising:
reacting 3-methylthiopropionaldehyde, while mixing intensively, with 2.5 to 25 wt. % of water, based on a total amount of the 3-methylthiopropionaldehyde and water used, at a temperature in a range of from 0 to 100° C.

10. The method of claim 9 , wherein the reaction is conducted for a duration in a range of from 0.5 to 72 h.

11. The method of claim 9 , further comprising:
distilling the 3-methylthiopropionaldehyde before the reacting.

12. A method for producing 2-hydroxy-4-(methylthio)butyronitrile, the method comprising:
reacting the composition of claim 1 , 3-methylthiopropane-1,1-diol, or the compound of formula (I), with hydrocyanic acid in the presence of an amine base.

13. A method for producing methionine hydantoin, the method comprising:
reacting the composition of claim 1 , 3-methylthiopropane-1,1-diol or the compound of formula (I), in the presence of water with hydrocyanic acid, ammonia, and carbon dioxide.

14. A method for producing D,L-methionine the method comprising:
reacting the composition of claim 1 with HCN, NH 3 , and carbon dioxide to give methionine hydantoin; and subsequently
hydrolyzing the methionine hydantoin, under alkaline conditions, to give a methionine alkali metal salt; and then
neutralizing the methionine alkali metal salt with acid to give methionine.

15. The composition of claim 1 , produced by a method comprising:
reacting 3-methylthiopropionaldehyde, while mixing intensively, with 2.5 to 25 wt. % of water, based on a total amount of the 3-methylthiopropionaldehyde and water used, at a temperature in a range of from 0 to 100° C.

16. A method of producing 2-hydroxy-4-(methylthio)butyric acid, the method comprising:
producing 2-hydroxy-4-(methylthio)butyronitrile by the method of claim 12 ; and
hydrolyzing the 2-hydroxy-4-(methylthio)butyronitrile in the presence of aqueous sulfuric acid to form a mixture comprising the 2-hydroxy-4-(methylthio)butyric acid and ammonium hydrogen sulfate.

Assignees

• Evonik Operations Gmbh

Inventors

• Hierold Judith
• Kopp Andrea
• Rautenberg Stephan
• Renner Christian

Classifications

• C07C323/12 Primary

  the carbon skeleton being acyclic and saturated · CPC title

• C07C319/26

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C319/12

  by reactions not involving the formation of mercapto groups · CPC title