Process to produce a mono vinyl thioether

Abstract

A process produces a mono vinyl thioether by reacting acetylene with a compound containing one thiol group and one hydroxy group, referred to as a thiol-hydroxy compound, where the reaction is performed at a pressure below 2 bars.

Claims

1: A process to produce a mono vinyl thioether, the process comprising: reacting acetylene with a thiol-hydroxy compound comprising one thiol group and one hydroxy group, wherein the reaction is performed at a pressure below 2 bars.

2: The process according to claim 1, wherein the thiol-hydroxy compound is a compound of formula I;
HS—R—OH wherein R is a linear or branched aliphatic hydrocarbon group which may comprise oxygen in the form of ether groups.

3: The process according to claim 1, wherein the thiol-hydroxy compound is 2-hydroxy-ethane-1-thiol.

4: The process according to claim 1, wherein the process is a process to produce vinyl thioethanol of formulas;
H.sub.2C═CH—S—CH.sub.2—CH.sub.2—OH.

5: The process according to claim 1, wherein the reaction is performed in presence of a catalyst.

6: The process according to claim 5, wherein the catalyst is an alkali salt of the thiol-hydroxy compound.

7: The process according to claim 5, wherein the catalyst is used in an amount of 0.1 to 10 parts by weight per 100 parts by weight of the thiol-hydroxy compound.

8: The process according to claim 1, wherein the reaction is performed at a pressure below 1.5 bars.

9: The process according to claim 1, wherein the acetylene is fed directly into a liquid phase comprising the thiol-hydroxy compound and any products already formed.

10: The process according to claim 1, wherein the acetylene is fed continuously to a reactor and unreacted acetylene as well as any other gaseous compounds are withdrawn from the reactor while the pressure is kept below 2 bars.

Description

EXAMPLES

Examples 1 to 4: Vinylation at Different Acetylene Pressures

[0036] A 0.3-liter autoclave was charged with 100 g of 2-mercaptoethanol (molecular weight: 78.13 g/mol) and 5 g of KOH pellets. The reactor was closed, heated to 100° C. and acetylene was passed through 6 norm-liters/hour under the pressure listed in table 1 for a reaction time of 10 hours. A norm-liter is one liter of a gas has at 0° C. and 1013 millibar. The composition of the mixture obtained in the reactor after 10 hours of reaction was analyzed via gas chromatography. The percentages listed in table 1 are area percentages of the corresponding peaks. The area percentages correspond substantially to the respective weight percentages. The remaining percentages to 100% correspond to unreacted starting materials.

TABLE-US-00001 TABLE 1 results of examples 1 to 4 area % vinyl area % divinyl ex- pressure thioethanol in compound in ample bar product mixture product mixture 1 17 89.1 6.5 2 11 89.1 3.8 3 5 94.8 1.6 4 1 98.3 0.3