Synthesis of asymmetrical sulfide compounds and asymmetrical ether compounds

Patent metadata

Field	Value
Publication number	US-10633334-B2
Application number	US-201916291018-A
Country	US
Kind code	B2
Filing date	Mar 4, 2019
Priority date	Mar 5, 2018
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

Abstract

The present invention discloses methods for synthesizing asymmetrical sulfide compounds and asymmetrical ether compounds from a variety of ether, sulfide, alcohol, and thiol reactants that are contacted in the presence of a suitable catalyst. Conversions of the limiting reactant to the desired asymmetrical sulfide or asymmetrical ether compound generally exceed 50%.

First claim

We claim:

1. A process for producing an ether or sulfide compound having formula (III):
R 1 —X—R 2   (III);

the process comprising contacting:
(a) a first ether or sulfide compound having formula (F),
R 1 —X—R 1   (F);

(b) a second ether or sulfide compound having formula (G),
R 2 —X—R 2   (G); and

(c) a catalyst;

to form a reaction mixture comprising the ether or sulfide compound having formula (III);
wherein:
each X independently is sulfur or oxygen;
R 1 is a C 1 to C 18 substituted or unsubstituted, cycloalkyl group or linear or branched alkyl group; and
R 2 is a C 1 to C 18 substituted or unsubstituted, cycloalkyl group or linear or branched alkyl group.

2. The process of claim 1 , wherein each X is sulfur.

3. The process of claim 2 , wherein the sulfide compound having formula (III) is methyl ethyl sulfide, methyl iso-propyl sulfide, methyl dodecyl sulfide, ethyl octyl sulfide, or n-pentyl n-heptyl sulfide.

4. The process of claim 1 , wherein each X is oxygen.

5. The process of claim 4 , wherein the ether compound having formula (III) is methyl ethyl ether, methyl iso-propyl ether, methyl tert-butyl ether, or methyl tert-amyl ether.

6. The process of claim 1 , wherein:
R 1 and R 2 independently are a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, or an octadecyl group; and
R 1 and R 2 are different.

7. 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.

8. The process of claim 1 , wherein the compound having formula (F) and the compound having formula (G) are combined prior to contacting a fixed bed of the catalyst.

9. The process of claim 1 , wherein a molar ratio of the compound having formula (F) to the compound having formula (G) is in a range from about 10:1 to about 1:10.

10. The process of claim 1 , wherein the process further comprises contacting the compound having formula (F), the compound having formula (G), the catalyst, with a sulfur-containing compound comprising H 2 S, CS 2 , di-tert-butyl polysulfide, or any combination thereof.

11. The process of claim 1 , wherein:
the reaction mixture contains less than or equal to about 5 wt. % of mercaptan reaction products;
the compound having formula (F) is a limiting reactant;
a conversion of the limiting reactant is at least about 60%; and
a yield of the compound having formula (III) is at least about 50 mol %, based on the limiting reactant.

12. 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.

13. The process of claim 1 , further comprising a step of isolating the compound having formula (III) from the reaction mixture to form a product stream containing the compound having formula (III).

14. The process of claim 13 , wherein:
the compound having formula (F) is a limiting reactant;
a yield of the compound having formula (III) in the product stream is at least about 50 mol %, based on the limiting reactant; and
a purity of the compound having formula (III) in the product stream is at least about 85 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

• C07C43/03

  having all ether-oxygen atoms bound to acyclic carbon atoms · CPC title

• C07C41/14

  by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification · CPC title

• C07C321/14

  of an acyclic saturated carbon skeleton · CPC title

• B01J21/04

  Alumina · CPC title

• B01J23/882

  and cobalt · CPC title