Synthesis of methyl ethyl sulfide and related production systems

Patent metadata

Field	Value
Publication number	US-10538488-B2
Application number	US-201916291014-A
Country	US
Kind code	B2
Filing date	Mar 4, 2019
Priority date	Mar 5, 2018
Publication date	Jan 21, 2020
Grant date	Jan 21, 2020

Abstract

The present invention discloses processes for producing methyl ethyl sulfide by contacting dimethyl sulfide and diethyl sulfide in the presence of a suitable catalyst. Methyl ethyl sulfide can be used as an odorant in natural gas. Integrated mercaptan and sulfide manufacturing systems and integrated methods for making mercaptans and sulfides also are disclosed.

First claim

We claim:

1. A process for producing methyl ethyl sulfide, the process comprising contacting:
(a) dimethyl sulfide;
(b) diethyl sulfide; and
(c) a catalyst;

to form a reaction mixture comprising the methyl ethyl sulfide.

2. The process of claim 1 , wherein the dimethyl sulfide and the diethyl sulfide are combined prior to contacting a fixed bed of the catalyst.

3. The process of claim 1 , wherein the step of contacting is conducted at:
a temperature in a range from about 200° C. to about 500° C.;
a pressure in a range from about 50 to about 850 psig (344 to 5860 kPag); and
a WHSV in a range from about 0.01 to about 3.

4. The process of claim 1 , wherein a molar ratio of dimethyl sulfide to diethyl sulfide (DMS:DES) is in a range from about 10:1 to about 1:10.

5. The process of claim 1 , wherein:
the diethyl sulfide is a limiting reactant in the production of the methyl ethyl sulfide; and
a molar ratio of dimethyl sulfide to diethyl sulfide (DMS:DES) is in a range from about 2:1 to about 20:1.

6. The process of claim 1 , wherein the process further comprises contacting the dimethyl sulfide, the diethyl sulfide, the catalyst, and a sulfur-containing compound comprising H 2 S, CS 2 , di-tert-butyl polysulfide, or any combination thereof.

7. The process of claim 1 , wherein the catalyst comprises a hydrotreating catalyst.

8. The process of claim 1 , wherein the catalyst comprises a supported CoMo catalyst, a supported NiMo catalyst, γ-alumina, a zeolite, or any combination thereof.

9. The process of claim 1 , wherein:
the reaction mixture contains less than or equal to about 3 wt. % methyl mercaptan and less than or equal to about 1 wt. % ethyl mercaptan;
a conversion of the diethyl sulfide is at least about 80%; and
a yield of the methyl ethyl sulfide is at least about 70 mol %, based on the diethyl sulfide.

10. The process of claim 1 , further comprising a step of isolating the methyl ethyl sulfide from the reaction mixture to form a product stream containing the methyl ethyl sulfide.

11. The process of claim 10 , wherein:
a yield of the methyl ethyl sulfide in the product stream is at least about 70 mol %, based on the diethyl sulfide; and
a purity of the methyl ethyl sulfide in the product stream is at least about 90 wt. %, based on the total weight of the product stream.

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Hasenberg Daniel M
• Lassen Kenneth M
• Kreider Jason L
• Hwu Henry

Classifications

• C07C323/14

  the carbon skeleton being acyclic and unsaturated · CPC title

• C07C321/14

  of an acyclic saturated carbon skeleton · CPC title

• C07C319/24

  by reactions involving the formation of sulfur-to-sulfur bonds · CPC title

• C07C319/08

  by replacement of hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07C319/20 Primary

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