Mixed decyl mercaptans compositions and methods of making same

Patent metadata

Field	Value
Publication number	US-9938237-B2
Application number	US-201715632910-A
Country	US
Kind code	B2
Filing date	Jun 26, 2017
Priority date	Dec 28, 2015
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

Compositions comprising branched C 10 mercaptans selected from the group consisting of 5-methyl-1-mercapto-nonane, 3-propyl-1-mercapto-heptane, 4-ethyl-1-mercapto-octane, 2-butyl-1-mercapto-hexane, 5-methyl-2-mercapto-nonane, 3-propyl-2-mercapto-heptane, 4-ethyl-2-mercapto-octane, 5-methyl-5-mercapto-nonane, and combinations thereof.

First claim

What is claimed is:

1. A composition comprising mercaptans, wherein at least about 50 wt. % of the mercaptans are at least two branched C 10 mercaptans selected from the group consisting of 5-methyl-1-mercapto-nonane (represented by Structure A), 3-propyl-1-mercapto-heptane (represented by Structure B), 4-ethyl-1-mercapto-octane (represented by Structure C), 2-butyl-1-mercapto-hexane (represented by Structure D), 5-methyl-2-mercapto-nonane (represented by Structure E), 3-propyl-2-mercapto-heptane (represented by Structure F), and 4-ethyl-2-mercapto-octane (represented by Structure G).

2. A process comprising:
reacting hydrogen sulfide (H 2 S) and a feedstock comprising one or more branched C 10 monoolefins in the presence of an initiating agent to produce a crude composition, wherein the branched C 10 monoolefins comprise 5-methyl-1-nonene, 3-propyl-1-heptene, 4-ethyl-1-octene, 2-butyl-1-hexene, or combinations thereof; and
recovering a reaction product from the crude composition, wherein the reaction product comprises mercaptans, wherein at least about 50 wt. % of the mercaptans are at least two branched C 10 mercaptans selected from the group consisting of 5-methyl-1-mercapto-nonane, 3-propyl-1-mercapto-heptane, 4-ethyl-1-mercapto-octane, 2-butyl-1-mercapto-hexane, 5-methyl-2-mercapto-nonane, 3-propyl-2-mercapto-heptane, and 4-ethyl-2-mercapto-octane.

3. The process of claim 2 , wherein the reaction product comprises at least about 25 wt. % branched C 10 mercaptans.

4. The process of claim 2 , wherein the reaction product further comprises at least about 5 wt. % branched C 20 sulfides represented by structure R 1 —S—R 2 , wherein R 1 and R 2 are each independently a branched C 10 alkyl group derived from the branched C 10 monoolefin, and wherein the branched C 10 alkyl group is selected from the group consisting of

wherein * designates the attachment point to the S atom of the branched C 20 sulfide.

5. The process of claim 2 , wherein the reaction product comprises (i) at least about 50 wt. % mercaptans; and (ii) at least about 10 wt. % sulfides, wherein at least about 50 wt. % of the sulfides are branched C 20 sulfides represented by the structure R 1 —S—R 2 , wherein R 1 and R 2 are each independently a functional group derived from an olefin, wherein the olefin comprises 5-methyl-1-nonene, 3-propyl-1-heptene, 4-ethyl-1-octene, 2-butyl-1-hexene, or combinations thereof.

6. The process of claim 2 , wherein the initiating agent comprises ultraviolet radiation.

7. The process of claim 6 , wherein the initiating agent further comprises a phosphite promoter, a photoinitiator, or both.

8. The process of claim 2 , wherein the initiating agent comprises an acid catalyst.

9. The process of claim 2 , wherein the initiating agent comprises a hydrodesulfurization catalyst.

10. The process of claim 6 , wherein the crude composition comprises C 10 mercaptans comprising from about 70 wt. % to about 95 wt. % C 10 primary mercaptans, from about 10 wt. % to about 20 wt. % C 10 secondary mercaptans, and from about 0 wt. % to about 5 wt. % C 10 tertiary mercaptans.

11. The process of claim 8 , wherein the crude composition comprises C 10 mercaptans comprising from about 0 wt. % to about 5 wt. % C 10 primary mercaptans, from about 80 wt. % to about 95 wt. % C 10 secondary mercaptans, and from about 5 wt. % to about 20 wt. % C 10 tertiary mercaptans.

12. The process of claim 9 , wherein the crude composition comprises C 10 mercaptans comprising from about 5 wt. % to about 30 wt. % C 10 primary mercaptans, from about 60 wt. % to about 75 wt. % C 10 secondary mercaptans, and from about 5 wt. % to about 15 wt. % C 10 tertiary mercaptans.

13. The process of claim 2 further comprising, prior to the reacting, separating the feedstock comprising one or more branched C 10 monoolefins from an effluent stream obtained from a 1-hexene production process.

14. The reaction product made by the process of claim 2 .

15. The composition of claim 1 , comprising at least about 50 wt. % mercaptans.

16. The composition of claim 1 , comprising at least about 70 wt. % mercaptans.

17. The composition of claim 1 , comprising at least 99 wt. % mercaptans.

18. The composition of claim 1 , wherein at least about 75 wt. % of the mercaptans are the branched C 10 mercaptans.

19. The composition of claim 1 , wherein at least about 85 wt. % of the mercaptans are the branched C 10 mercaptans.

20. A mercaptan composition comprising at least two branched C 10 mercaptans selected from the group consisting of 5-methyl-1-mercapto-nonane (represented by Structure A), 3-propyl-1-mercapto-heptane (represented by Structure B), 4-ethyl-1-mercapto-octane (represented by Structure C), 2-butyl-1-mercapto-hexane (represented by Structure D), 5-methyl-2-mercapto-nonane (represented by Structure E), 3-propyl-2-mercapto-heptane (represented by Structure F), and 4-ethyl-2-mercapto-octane (represented by Structure G),

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Matson Michael S
• Byers Jim D
• Kreider Jason L

Classifications

• B01J2219/1203

  Incoherent waves · CPC title

• C07C319/04 Primary

  by addition of hydrogen sulfide or its salts to unsaturated compounds · CPC title

• C07C321/04 Primary

  of an acyclic saturated carbon skeleton · CPC title

• B01J2219/0877

  Liquid · CPC title

• B01J19/123

  Ultraviolet light · CPC title