IP Library Granted Patent US 8,734,637
Granted Patent B2
US 8,734,637 · App. 12/723,434 · Granted May 27, 2014

Method of scavenging hydrogen sulfide and/or mercaptans using triazines

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Quick Facts
Patent No.
US 8,734,637
App. No.
12/723,434
Granted
May 27, 2014
Kind
B2
Abstract

Sulfhydryl compounds, including hydrogen sulfide and mercaptans, may be removed from a fluid or gaseous stream or substrate by reacting the hydrogen sulfide and mercaptans in the stream with a scavenger of the structural formula: wherein R 1 , R 2 and R 3 are each independently selected from the group consisting of R 4 and R 5 , R 4 is a C 1 -C 20 straight or branched chain alkyl group, R 5 is —[(CH) m —NH] p —(CH 2 ) n OH, n and m are independently an integer from 2 to about 6, p is from 1 to about 6; and wherein at least one of R 1 , R 2 and R 3 is R 4 and at least one of R 1 , R 2 and R 3 is R 5 .

Claims (34)

1. A method for scavenging hydrogen sulfide and/or mercaptans from a liquid or gaseous stream which comprises bringing the stream into contact with a scavenging effective amount of at least one triazine of the formula:

wherein R 1 , R 2 and R 3 are each independently selected from the group consisting of R 4 and R 5 , R 4 is a C 1 -C 20 straight or branched chain alkyl group, R 5 is —[(CH) m —NH] p —(CH 2 ) n OH, n and m are independently an integer from 2 to about 6, p is from 1 to about 6; and

further wherein at least one of R 1 , R 2 and R 3 is R 4 and at least one of R 1 , R 2 and R 3 is R 5 .

2. The method of claim 1 , wherein R 5 is —CH 2 CH 2 NHCH 2 CH 2 OH.

3. The method of claim 1 , wherein R 4 is a C 1 -C 6 straight or branched chain alkyl group.

4. The method of claim 3 , wherein R 4 is t-butyl.

5. The method of claim 1 , wherein two of R 1 , R 2 and R 3 are R 5 and one of R 1 , R 2 and R 3 is R 4 .

6. The method of claim 1 , wherein the triazine is a mixture of:

(i) a first triazine of formula (I) wherein R 1 and R 2 are R 4 and R 3 is R 5 ;

(ii) a second triazine of formula (I) wherein R 1 is R 4 and R 2 and R 3 are R 5 ;

(iii) a third triazine of formula (I) wherein R 1 , R 2 and R 3 are R 4 ; and

(iv) a fourth triazine of formula (I) wherein R 1 , R 2 and R 3 are R 5

and further wherein the substituent for R 4 for each of the triazines of (i), (ii), (iii) and (iv) is the same and the substituent for R 5 for each of the triazines of (i), (ii), (iii) and (iv) is the same.

7. The method of claim 6 , wherein each R 4 of the triazines of (i), (ii), (iii) and (iv) is a C 1 -C 6 alkyl group.

8. The method of claim 7 , wherein the C 1 -C 6 alkyl group is t-butyl.

9. The method of claim 6 , wherein each R 5 of the triazines of (i), (ii), (iii) and (iv) is —CH 2 CH 2 NHCH 2 CH 2 OH.

10. The method of claim 9 , wherein each R 4 of the triazines of (i), (ii), (iii) is t-butyl.

11. The method of claim 1 , wherein p is 2.

12. A method for reducing an amount of sulfhydryl compounds in a hydrocarbon substrate, comprising mixing the hydrocarbon substrate with a scavenging effective amount of a triazine of the formula:

wherein R 1 , R 2 and R 3 are each independently selected from the group consisting of R 4 and R 5 , R 4 is a C 1 -C 20 straight or branched chain alkyl group, R 5 is —[(CH) m —NH] p —(CH 2 ) n OH, n and m are independently an integer from 2 to about 6, p is from 1 to about 6; and

further wherein at least one of R 1 , R 2 and R 3 is R 4 and at least one of R 1 , R 2 and R 3 is R 5 .

13. The method of claim 12 , wherein R 5 is —CH 2 CH 2 NHCH 2 CH 2 OH.

14. The method of claim 12 , wherein R 4 is a C 1 -C 6 straight or branched chain alkyl group.

15. The method of claim 14 , wherein R 4 is t-butyl.

16. The method of claim 12 , wherein R 4 is t-butyl.

17. The method of claim 12 , wherein the hydrocarbon substrate is a wet or dry gaseous mixture of hydrogen sulfide and/or mercaptan and hydrocarbon vapors.

18. The method of claim 17 , wherein the hydrocarbon substrate is a sour aqueous or sour hydrocarbon substrate.

19. The method of claim 18 , wherein the triazine is a mixture of:

(i) a first triazine of formula (I) wherein R 1 and R 2 are R 4 and R 3 is R 5 ;

(ii) a second triazine of formula (I) wherein R 1 is R 4 and R 2 and R 3 are R 5 ;

(iii) a third triazine of formula (I) wherein R 1 , R 2 and R 3 are R 4 ; and

(iv) a fourth triazine of formula (I) wherein R 1 , R 2 and R 3 are R 5

and further wherein the substituent for R 4 for each of the triazines of (i), (ii), (iii) and (iv) is the same and the substituent for R 5 for each of the triazines of (i), (ii), (iii) and (iv) is the same.

20. The method of claim 19 , wherein each R 5 in the first triazine, second triazine, and fourth triazine is —CH 2 CH 2 NHCH 2 CH 2 OH and each R 4 in the first triazine, second triazine, and third triazine is t-butyl.

Assignments (7)
CHANGE OF NAME Recorded Feb 16, 2022
From: BAKER HUGHES, A GE COMPANY, LLC
To: BAKER HUGHES HOLDINGS LLC
Reel/Frame 059142/0921 →
CHANGE OF NAME Recorded Feb 16, 2018
From: BAKER HUGHES INCORPORATED
To: BAKER HUGHES, A GE COMPANY, LLC
Reel/Frame 045349/0522 →
ENTITY CONVERSION Recorded Oct 4, 2017
From: BAKER HUGHES INCORPORATED
To: BAKER HUGHES, A GE COMPANY, LLC
Reel/Frame 044127/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2011
From: BJ SERVICES COMPANY LLC
To: BAKER HUGHES INCORPORATED
Reel/Frame 026508/0854 →
CHANGE OF NAME Recorded Jun 23, 2011
From: BSA ACQUISITION LLC
To: BJ SERVICES COMPANY LLC
Reel/Frame 026498/0356 →
MERGER Recorded Jun 17, 2011
From: BJ SERVICES COMPANY
To: BSA ACQUISITION LLC
Reel/Frame 026465/0022 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2010
From: TAYLOR, GRAHAME N.
To: BJ SERVICES COMPANY
Reel/Frame 024075/0485 →