Synthesis of methyl ethyl sulfide and related production systems

Patent metadata

Field	Value
Publication number	US-10927074-B2
Application number	US-201916709992-A
Country	US
Kind code	B2
Filing date	Dec 11, 2019
Priority date	Mar 5, 2018
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

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. An integrated mercaptan and sulfide manufacturing system comprising:
(i) a mercaptan production system capable of producing methyl mercaptan and dimethyl sulfide from methanol and H 2 S, and capable of producing ethyl mercaptan and diethyl sulfide from ethanol and H 2 S;
(ii) a DMDS production system for consuming at least a portion of the methyl mercaptan from the mercaptan production system, wherein the DMDS production system is capable of producing dimethyl disulfide from the methyl mercaptan;
(iii) an ETE production system for consuming at least a portion of the ethyl mercaptan from the mercaptan production system, wherein the ETE production system is capable of producing ethylthioethanol from the ethyl mercaptan; and
(iv) a MES production system for consuming at least a portion of the dimethyl sulfide and the diethyl sulfide from the mercaptan production system, wherein the MES production system is capable of producing methyl ethyl sulfide from the dimethyl sulfide and the diethyl sulfide.

2. The manufacturing system of claim 1 , wherein the MES production system comprises a reactor capable of reacting the dimethyl sulfide and the diethyl sulfide in the presence of a catalyst to form a reaction mixture containing the methyl ethyl sulfide.

3. The manufacturing system of claim 1 , wherein the MES production system comprises a fixed bed reactor capable of reacting the dimethyl sulfide and the diethyl sulfide in the vapor phase with a fixed bed of a catalyst to form a reaction mixture containing the methyl ethyl sulfide.

4. The manufacturing system of claim 3 , wherein the MES production system comprises a downstream separations system capable of isolating the methyl ethyl sulfide from the reaction mixture to form a product stream containing the methyl ethyl sulfide.

5. The manufacturing system of claim 4 , wherein the downstream separations system is further capable of isolating unreacted dimethyl sulfide and diethyl sulfide from the reaction mixture, and recycling the unreacted dimethyl sulfide and diethyl sulfide to the reactor.

6. The manufacturing system of claim 1 , wherein:
at least about 85 wt. % of the methyl mercaptan from the mercaptan production system is consumed in the DMDS production system; and
at least about 85 wt. % of the diethyl sulfide from the mercaptan production system is consumed in the MES production system.

7. An integrated method for producing mercaptans and sulfides, the method comprising:
(a) reacting methanol and H 2 S to form methyl mercaptan and dimethyl sulfide;
(b) reacting ethanol and H 2 S to form ethyl mercaptan and diethyl sulfide;
(c) reacting at least a portion of the methyl mercaptan with hydrogen peroxide and sodium hydroxide to form dimethyl disulfide;
(d) reacting at least a portion of the ethyl mercaptan with ethylene oxide to form ethylthioethanol; and
(e) reacting at least a portion of the dimethyl sulfide and the diethyl sulfide to form methyl ethyl sulfide.

8. The method of claim 1 , wherein at least about 75 wt. % of the methyl mercaptan produced in step (a) is consumed in step (c).

9. The method of claim 7 , wherein at least about 75 wt. % of the diethyl sulfide produced in step (b) is consumed in step (e).

10. The manufacturing system of claim 1 , wherein the DMDS production system is capable of converting at least about 90 mol % of the methyl mercaptan to the dimethyl disulfide.

11. The manufacturing system of claim 1 , wherein the ETE production system is capable of converting at least about 90 mol % of the ethyl mercaptan to the ethylthioethanol.

12. The manufacturing system of claim 2 , wherein the catalyst comprises a supported CoMo catalyst, a supported NiMo catalyst, γ-alumina, a zeolite, or any combination thereof.

13. The manufacturing system of claim 2 , wherein the reactor is constructed of a stainless steel.

14. The manufacturing system of claim 4 , wherein the downstream separations system comprises at least one distillation column.

15. The manufacturing system of claim 4 , wherein the downstream separations system is capable of forming the product stream at a purity of the methyl ethyl sulfide in the product stream of at least about 90 wt. %, based on the total weight of the product stream.

16. The manufacturing system of claim 4 , wherein the downstream separations system is capable of forming the product stream at a yield of the methyl ethyl sulfide in the product stream of at least about 80 mol %, based on the diethyl sulfide.

17. The method of claim 7 , wherein:
the dimethyl sulfide and the diethyl sulfide are reacted in the presence of a catalyst to form a reaction mixture containing the methyl ethyl sulfide; and
the catalyst comprises a supported CoMo catalyst, a supported NiMo catalyst, γ-alumina, a zeolite, or any combination thereof.

18. The method of claim 17 , further comprising a step of isolating unreacted dimethyl sulfide and diethyl sulfide from the reaction mixture, and recycling the unreacted dimethyl sulfide and diethyl sulfide.

19. The method of claim 17 , further comprising a step of isolating the methyl ethyl sulfide from the reaction mixture to form a product stream containing the methyl ethyl sulfide.

20. The method of claim 19 , wherein 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.

21. The method of claim 7 , wherein:
at least about 90 mol % of the methyl mercaptan is converted to the dimethyl disulfide in step (c); and/or
at least about 90 mol % of the ethyl mercaptan is converted to the ethylthioethanol in step (d).

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

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

Classifications

• C07C319/28

  Separation; Purification · CPC title

• C07C323/14

  the carbon skeleton being acyclic and unsaturated · CPC title

• C07C321/14

  of an acyclic saturated carbon skeleton · CPC title

• C07C319/14

  of sulfides · CPC title

• C07C319/08

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