Epoxide-based hydrogen sulfide scavengers

Patent metadata

Field	Value
Publication number	US-9719030-B2
Application number	US-201414314683-A
Country	US
Kind code	B2
Filing date	Jun 25, 2014
Priority date	Jun 27, 2013
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

Disclosed herein are scavenging compounds and compositions useful in applications relating to the production, transportation, storage, and separation of crude oil and natural gas. Also disclosed herein are methods of using the compounds and compositions as scavengers, particularly in applications relating to the production, transportation, storage, and separation of crude oil and natural gas.

First claim

What is claimed is:

1. A method of sweetening a fluid or gas, comprising treating the fluid or gas with an effective amount of a composition comprising one or more compounds of formula (I),

wherein,
X is selected from the group consisting of —OH, —SH, and —NHR 3 ;
R 3 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, cycloalkyl, and —C(O)R 7 ;
R 7 is selected from the group consisting of —OR 15 , —SR 16 , —NR 17 R 18 , hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
R 15 , R 16 , R 17 , and R 18 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
R a , R b , R c , R d , R e , R f , and R g are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; or R d and R f together with the carbon atoms to which they are attached form an aryl or a heteroaryl, provided that R e and R g are absent, R a , R b , and R c are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl when R d and R f together with the carbon atoms to which they are attached form an aryl or a heteroaryl; and

n is 0 or 1;
wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurrence, substituted or unsubstituted with one or more suitable substituents.

2. The method of claim 1 , wherein X is —OH.

3. The method of claim 2 , wherein R a , R b , R c , R d , R e , R f and R g are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1 -C 10 -alkyl, fluoro, bromo, and iodo.

4. The method of claim 1 , wherein X is —OH; R a is hydrogen or substituted or unsubstituted alkyl; R b is hydrogen; R e is hydrogen; R d is hydrogen or substituted or unsubstituted alkyl; R e is hydrogen; and n is 0.

5. The method of claim 1 , wherein X is —OH; R a is hydrogen or unsubstituted C 1 -C 10 -alkyl; R b is hydrogen; R e is hydrogen; R d is hydrogen or unsubstituted C 1 -C 10 -alkyl; R e is hydrogen; and n is 0.

6. The method of claim 1 , wherein X is —OH; R a is hydrogen or substituted or unsubstituted alkyl; R b is hydrogen; R e is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen or substituted or unsubstituted alkyl; R g is hydrogen; and n is 1.

7. The method of claim 1 , wherein X is —OH; R a is hydrogen or unsubstituted C 1 -C 10 -alkyl; R b is hydrogen; R e is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen or unsubstituted C 1 -C 10 -alkyl; R g is hydrogen; and n is 1.

8. The method of claim 1 , wherein R a , R b , and R c are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; R d and R f together with the carbon atoms to which they are attached form an aryl group; R e is absent; R g is absent; and n is 1.

9. The method of claim 1 , wherein X is —OH; R a is hydrogen; R b is hydrogen; R c is hydrogen; R d and R f together with the carbon atoms to which they are attached form a phenyl group, optionally having one to four suitable substituents in addition to the —OH; R e is absent; R g is absent; and n is 1.

10. The method of claim 1 , wherein X is —OH; R a is —(CH 2 ) 7 —C(O)OR x , wherein R x is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl, wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurrence, substituted or unsubstituted with one or more suitable substituents; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is —(CH 2 ) 5 CH 3 ; R g is hydrogen; and n is 1.

11. The method of claim 1 , wherein X is —OH; R a is —(CH 2 ) 7 —C(O)OR x , wherein R x is

R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is —(CH 2 ) 5 CH 3 ; R g is hydrogen; and n is 1.

12. The method of claim 1 , X is —OH; R a is —(CH 2 ) 7 —C(O)OR x , wherein R x is

R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is —(CH 2 ) 5 CH 3 ; R g is hydrogen; and n is 1.

13. The method of claim 1 , wherein the compound of formula (I) is selected from the group consisting of:

14. The method of claim 1 , wherein the composition comprises a surfactant.

15. The method of claim 1 , wherein the composition comprises a cocodimethylamine oxide surfactant.

16. The method of claim 1 , wherein the composition scavenges hydrogen sulfide and/or mercaptans from the fluid or gas.

17. The method of claim 1 , wherein the fluid or gas is produced or used in the production, transportation, storage, and/or separation of crude oil or natural gas.

18. The method of claim 1 , wherein the fluid or gas is produced or used in a coal-fired process, a waste-water process, a farm, a slaughter house, a land-fill, a municipality waste-water plant, a coking coal process, or a biofuel process.

19. A method of sweetening a fluid or gas, comprising treating the fluid or gas with an effective amount of a composition comprising one or more compounds of formula (II),

wherein
R is independently, at each occurrence, selected from the group consisting of hydrogen and a moiety comprising an α- or β-functionalized epoxide, said α- or β-functionalization selected from the group consisting of —OH, —SH, and —NHR 23 , wherein at least one R group is a moiety comprising said α- or β-functionalized epoxide;
R 23 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, cycloalkyl, and —C(O)R 27 ;
R 27 is selected from the group consisting of —OR 35 , —SR 36 , —NR 37 R 38 , hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
R 35 , R 36 , R 37 , and R 38 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;

R″, R s , and R t are each independently, at each occurrence, selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
R′ and R′″ are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
y is independently, at each occurrence, an integer selected from 0 to 6; and
z is an integer selected from 1 to 20;
wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurre

Assignees

• Ecolab Usa Inc

Inventors

• Sorrells Jennifer L
• Soriano Jr Nestor U

Classifications

• B01D2257/306

  Organic sulfur compounds, e.g. mercaptans · CPC title

• B01D2257/304

  Hydrogen sulfide · CPC title

• B01D2258/05

  Biogas · CPC title

• B01D2252/608

  Antifoaming agents · CPC title

• C10L2230/02

  Absorbents, e.g. in the absence of an actual absorbent column or scavenger · CPC title