Method for the preparation of a monothiocarbonate compound

Patent metadata

Field	Value
Publication number	US-10889559-B2
Application number	US-201816633870-A
Country	US
Kind code	B2
Filing date	Aug 7, 2018
Priority date	Aug 17, 2017
Publication date	Jan 12, 2021
Grant date	Jan 12, 2021

Abstract

Process for the preparation of a compound with at least one monothiocarbonate group by reacting:—a compound with at least one mercaptoalcohol group and—a dialkylcarbonate, in the presence of a catalyst wherein the catalyst is a salt of a metal selected from group IIIb or IVb of the periodic system.

First claim

The invention claimed is:

1. A process for preparing a compound having at least one monothiocarbonate group, the process comprising:
reacting
a compound having at least one mercaptoalcohol group, and
a dialkylcarbonate,
in the presence of a catalyst,

wherein the catalyst is a salt of a metal selected from group IIIb or IVb of the periodic table of elements.

2. The process of claim 1 , wherein the compound having the at least one monothiocarbonate group is a compound of formula I

wherein R 1 , R 2 , R 3 and R 4 each independently represent hydrogen or an organic group comprising up to 50 carbon atoms, and
R 2 and R 4 and the two carbon atoms to which R 2 and R 4 are bonded optionally form a ring system.

3. The process of claim 2 , wherein the compound having the at least one mercaptoalcohol group is a compound of formula IIb

wherein R 1 , R 2 , R 3 and R 4 are defined as in formula I.

4. The process of claim 1 , wherein the dialkylcarbonate is a compound of formula III

wherein R 5 and R 6 each independently represent a non-aromatic hydrocarbon group comprising 1 to 10 carbon atoms or may together form an alkylene bridge comprising 2 to 9 carbon atoms.

5. The process of claim 1 , wherein the compound having the at least one mercaptoalcohol group is mercaptoethanol.

6. The process of claim 4 , wherein the compound of formula III is diethylcarbonate.

7. The process of claim 1 , wherein the catalyst is a salt of scandium or titanium.

8. The process of claim 1 , wherein an anion of the salt is a halogenide, an alcoholate or a carboxylate.

9. The process of claim 1 , wherein the catalyst is titanium tetra isopropylate.

10. The process of claim 1 , wherein the catalyst is a titanium-tetra alcoholate.

11. The process of claim 1 , wherein a molar ratio of mercaptoalcohol groups of the compound having at least one mercaptoalcohol group to the dialkyl carbonate is 0.5:1 to 1:0.5.

12. The process according to claim 1 , wherein the catalyst is present during the reacting in an amount of 0.005 to 0.05 mol per mol of the mercaptoalcohol groups of the compound having at least one mercaptoalcohol group.

13. The process according to claim 1 , wherein the reacting is carried out at a temperature of from 80 to 140° C.

14. The process according to claim 1 , wherein the reacting is carried out in the absence of a solvent other than the compound having at least one mercaptoalcohol group and the dialkylcarbonate.

15. The process according to claim 1 , further comprising:
removing an alcohol formed while reacting the compound having at least one mercaptoalcohol group and the dialkylcarbonate.

16. The process according to claim 1 , further comprising:
during the reacting, removing by distillation an alcohol formed from the compound having at least one mercaptoalcohol group and the dialkylcarbonate.

17. The process according to claim 1 , further comprising:
after the reacting, vacuum distilling the monothiocarbonate from a reaction mixture formed by reacting the compound having at least one mercaptoalcohol group and the dialkylcarbonate, wherein the monothiocarbonate obtained by the vacuum distilling has a purity of greater than 98% determined from the peak area of the monothiocarbonate peak in the gas chromatogram compared to the area of all peaks (total count).

Assignees

• Basf Se

Inventors

• Rudolf Peter
• Arndt Jan-Dirk
• Holub Nicole
• Mormul Verena
• Thiel Indre

Classifications

• C07D327/04 Primary

  Five-membered rings · CPC title

• C07C329/06

  having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms · CPC title

• C07C69/02

  Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen · CPC title

• C07D263/22 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms · CPC title

• B01J21/063

  Titanium; Oxides or hydroxides thereof · CPC title