Storage of 3-methylthiopropionaldehyde and methyl mercaptan

Patent metadata

Field	Value
Publication number	US-10633335-B2
Application number	US-201715851362-A
Country	US
Kind code	B2
Filing date	Dec 21, 2017
Priority date	Dec 22, 2016
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

Abstract

A compound, which is 1-(1,3-bis(methylthio)propoxy)-3-(methylthio)propan-1-ol, a composition containing the compound, a method for the preparation thereof, a method for preparing 3-methylthiopropionaldehyde by reacting 1-(1,3-bis(methylthio)propoxy)-3-(methylthio)propan-1-ol with acrolein, and also to the use of 1-(1,3-bis(methylthio)propoxy)-3-(methylthio)propan-1-ol or compositions containing the compound for the storage and/or transport of 3-methylthiopropionaldehyde and/or methyl mercaptan.

First claim

The invention claimed is:

1. A method for preparing a compound of formula (I):

the method comprising:
a) bringing a composition comprising 3-methylthiopropionaldehyde into contact with a composition comprising methyl mercaptan, to obtain a composition comprising the compound of formula (I), wherein a molar ratio of 3-methylthiopropionaldehyde to methyl mercaptan in a) is between 2:1 and 4:1.

2. The method according to claim 1 , wherein a) is conducted at a temperature of not more than 70° C.

3. The method according to claim 1 , additionally comprising the step upstream of a) of
a′) bringing a composition comprising acrolein into contact with a composition comprising methyl mercaptan, to obtain a composition comprising 3-methylthiopropionaldehyde.

4. The method according to claim 1 , additionally comprising the step upstream and/or downstream of a) of
a″) bringing a composition comprising the compound of formula (I) into contact with acrolein, to obtain a composition comprising 3-methylthiopropionaldehyde.

5. The method according to claim 3 , wherein a) and/or a′) are carried out in the presence of at least one nitrogen-containing base as catalyst.

6. The method according to claim 5 , wherein the nitrogen-containing base is an unsubstituted or substituted N-heterocyclic compound or an amine of the formula NR 1 R 2 R 3 , wherein R 1 , R 2 and R 3 are either identical or different and are each independently of each other hydrogen, an alkyl residue having one to four carbon atoms or an arylalkyl residue having 7 to 14 carbon atoms, with the proviso that, if one of the residues R 1 , R 2 or R 3 is hydrogen, the two other residues are not hydrogen.

7. The method according to claim 3 , wherein step a) and/or step a′) are carried out in the presence of at least one acid.

8. A method for preparing 3-methylthiopropionaldehyde, comprising bringing a composition comprising a compound of formula (I) obtained by the method accoring to claim 1 , into contact with a composition comprising acrolein, to obtain a composition comprising 3-methylthiopropionaldehyde.

9. The method according to claim 8 , additionally comprising:
a′) bringing a composition comprising acrolein into contact with a composition comprising methyl mercaptan, to obtain a composition comprising 3-methylthiopropionaldehyde; or
a″) bringing a composition comprising the compound of formula (I) into contact with acrolein, to obtain a composition comprising 3-methylthiopropionaldehyde.

10. The method according to claim 1 , wherein a) is conducted at a temperature of not more than 25° C.

11. The method according to claim 1 , wherein a) is conducted at a temperature of not more than 15° C.

12. The method according to claim 1 , wherein the compound is at least one selected from the group consisting of:
1-(1R,3-bis(methylthio)propoxy)-3-(methylthio)propan-1R-ol,
1-(1R,3-bis(methylthio)propoxy)-3-(methylthio)propan-1S-ol,
1-(1S,3-bis(methylthio)propoxy)-3-(methylthio)propan-1R-ol, and
1-(1S,3-bis(methylthio)propoxy)-3-(methylthio)propan-1S-ol.

Assignees

• Evonik Operations Gmbh

Inventors

• Hierold Judith
• Ceylan Sascha
• Rautenberg Stephan
• Jakob Harald
• Kaiser Christian
• Kopp Andrea
• Geist Lucas

Classifications

• C07C323/22

  containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• C07C321/04

  of an acyclic saturated carbon skeleton · CPC title

• C07C319/20

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

• C07C319/12

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

• C07B2200/07

  Optical isomers · CPC title