Mixed decyl mercaptans compositions and methods of making same

Patent metadata

Field	Value
Publication number	US-10040758-B2
Application number	US-201715825555-A
Country	US
Kind code	B2
Filing date	Nov 29, 2017
Priority date	Dec 28, 2015
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

Compositions comprising branched C10 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. Compositions comprising C11+ mercaptans, wherein the C11+ mercaptans are characterized by structure R6—SH, wherein R6 is an alkyl group derived from one or more C11+ monoolefins, and wherein the one or more C11+ monoolefins comprise C11 internal monoolefins, C12 internal monoolefins, C13 internal monoolefins, C14 internal monoolefins, 1-tetradecene, 1-hexadecene, or combinations thereof. Compositions comprising branched C10+ mercaptans, wherein the branched C10+ mercaptans are characterized by structure R14—SH, wherein R14 is an alkyl group derived from one or more branched C10 to C30 monoolefins.

First claim

What is claimed is:

1. A composition comprising C 10+ mercaptans, wherein at least about 50 wt. % of the C 10+ mercaptans are branched C 10 to C 30 mercaptans characterized by the general formula R 14 —SH, wherein R 14 is a branched alkyl group; wherein R 14 has from 10 to 30 carbon atoms; wherein the branched C 10 to C 30 mercaptans characterized by the general formula R 14 —SH are 1) C 10+ mercaptans selected from the group consisting of a branched C 10 to C 30 mercaptan represented by Structure A-1, a branched C 10 to C 30 mercaptan represented by Structure B-1, a branched C 10 to C 30 mercaptan represented by Structure D-1, a branched C 10 to C 30 mercaptan represented by Structure E-1, a branched C 10 to C 30 mercaptan represented by Structure F-1, a branched C 10 to C 30 mercaptan represented by Structure G-1, and combinations thereof; and 2) a branched C 10 to C 30 mercaptan represented by Structure H-1; and wherein R 9 is a C 1 to C 21 alkyl group

2. The composition of claim 1 , wherein the branched C 10 to C 30 mercaptans characterized by the general formula R 14 —SH further comprise a branched C 10 to C 30 mercaptan represented by Structure C-1

3. The composition of claim 1 , wherein R 9 is a C 2 to C 21 alkyl group.

4. A composition comprising C 20+ sulfides, wherein at least about 50 wt. % of the C 20+ sulfides are branched C 20 to C 60 sulfides represented by structure R 10 —S—R 11 , wherein R 10 and R 11 are each independently a functional group derived from an olefin, wherein the olefin comprises a branched C 10 to C 30 monoolefin; wherein the branched C 10 to C 30 monoolefin comprises 1) a branched C 10 to C 30 monoolefin represented by Structure I-1, a branched C 10 to C 30 monoolefin represented by Structure J-1, combinations thereof; and 2) a branched C 10 to C 30 monoolefin represented by Structure L-1; and wherein R 9 is a C 1 to C 2 alkyl group

5. The composition of claim 4 , wherein the branched C 10 to C 30 monoolefin further comprises, a branched C 10 to C 30 monoolefin represented by Structure K-1

6. The composition of claim 4 , wherein R 9 is a C 2 to C 21 alkyl group.

7. The composition of claim 4 , wherein the olefin further comprises from about 0.1 mol % to about 26 mol % linear C 10 to C 30 monoolefins.

8. The composition of claim 4 , wherein the olefin further comprises from about 0.1 mol % to about 5 mol % C 8 monoolefins, the C 8 monoolefins comprising at least about 95 mol % 1-octene.

9. The composition of claim 4 , wherein the olefin comprises i) at least about 70 wt. % branched C 10 to C 30 monoolefins; ii) less than about 15 wt. % C 9 -monoolefins; and iii) less than about 15 wt. % C 31+ monoolefins; based on the total weight of the olefin.

10. A composition comprising:
(A) at least about 25 wt. % branched C 10 to C 30 mercaptans characterized by the general formula R 14 —SH, wherein R 14 is a branched alkyl group; and wherein R 14 has from 10 to 30 carbon atoms; and
(B) at least about 10 wt. % branched C 2 to C % 6 sulfides represented by structure R 10 —S—R 11 , wherein R 10 and R 11 are each independently a functional group derived from an olefin, and wherein the olefin comprises a branched C 10 to C 30 monoolefin.

11. The composition of claim 10 , wherein the branched C 10 to C 30 mercaptans characterized by the general formula R 14 —SH are selected from the group consisting of a branched C 10 to C 30 mercaptan represented by Structure A-1, a branched C 10 to C 30 mercaptan represented by Structure B-1, a branched C 10 to C 30 mercaptan represented by Structure C-1, a branched C 10 to C 30 mercaptan represented by Structure D-1, a branched C 10 to C 30 mercaptan represented by Structure E-1, a branched C 10 to C 30 mercaptan represented by Structure F-1, a branched C 10 to C 30 mercaptan represented by Structure G-1, a branched C 10 to C 30 mercaptan represented by Structure H-1, and combinations thereof; wherein the branched C 10 to C 30 monoolefin comprises a branched C 10 to C 30 monoolefin represented by Structure I-1, a branched C 10 to C 30 monoolefin represented by Structure J-1, a branched C 10 to C 30 monoolefin represented by Structure K-1, a branched C 10 to C 30 monoolefin represented by Structure L-1, or combinations thereof; and wherein R 9 is a C 1 to C 21 alkyl group.

12. The composition of claim 11 , wherein R 9 is a C 2 to C 21 alkyl group.

13. A process comprising reacting hydrogen sulfide (H 2 S) and a feedstock comprising one or more branched C 10 to C 30 monoolefins in the presence of an initiating agent to produce a branched C 10+ mercaptans crude composition, wherein the branched C 10+ mercaptans crude composition comprises branched C 10 to C 30 mercaptans characterized by the general formula R 14 —SH, wherein R 14 is a branched alkyl group; wherein R 14 has from 10 to 30 carbon atoms; wherein the branched C 10 to C 30 mercaptans characterized by the general formula R 14 —SH are 1) C 10+ mercaptans selected from the group consisting of a branched C 10 to C 3Q mercaptan represented by Structure A-1, a branched C 10 to C 30 mercaptan represented by Structure B-1, a branched C 10 to C 30 mercaptan represented by Structure D-1, a branched C 10 to C 30 mercaptan represented by Structure E-1, a branched C 10 to C 30 mercaptan represented by Structure F-1, a branched C 10 to C 30 mercaptan represented by Structure G-1, and combinations thereof; and 2) a branched C 10 to C 30 mercaptan represented by Structure H-1; and wherein R 9 is a C 1 to C 21 alkyl group.

14. The process of claim 13 further comprising recovering a first reaction product from the branched C 10+ mercaptans crude composition, wherein the first reaction product comprises at least about 25 wt. % branched C 10 to C 30 mercaptans.

15. The process of claim 13 further comprising recovering a second reaction product from the branched C 10+ mercaptans crude composition, wherein the second reaction product comprises at least about 5 wt. % branched C 20 to C 60 sulfides represented by structure R 10 —S—R 11 , wherein R 10 and R 11 are each independently a branched C 10 to C 30 alkyl group derived from a branched C 10 to C 30 monoolefin.

16. The process of claim 15 , wherein the branched C 10 to C 30 alkyl group is selected from the group consisting of

wherein * designates the attachment point to the S atom of the branched C 20 to C 60 sulfide; and wherein R 9 is a C 1 to C 21 alkyl group.

17. The process of claim 13 , wherein the initiating agent comprises ultraviolet radiation.

18. The process of claim 17 , wherein the initiating agent further comprises a phosphite promoter, a photoinitiator, a sulfur scavenger, an antioxidant, or combinations thereof.

19. The process of claim 17 , wherein the branched C 10+ mercaptans crude composition comprises C 10 to C 30 mercaptans comprising from about 70 wt. % to about 95 wt. % C 10 to C 30 primary mercaptans, from about 10

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

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

Classifications

• C07C321/04

  of an acyclic saturated carbon skeleton · CPC title

• B01J19/123

  Ultraviolet light · CPC title

• B01J2219/0877

  Liquid · CPC title

• B01J2219/1203

  Incoherent waves · CPC title

• C07C319/04 Primary

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