IP Library Granted Patent US 9,638,018
Granted Patent B2
US 9,638,018 · App. 14/108,617 · Granted May 2, 2017

Scavenging hydrogen sulfide

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Quick Facts
Patent No.
US 9,638,018
App. No.
14/108,617
Filed
Dec 17, 2013
Granted
May 2, 2017
Kind
B2
Art Unit
1738
USPC
166/305.1
Abstract

Alpha-hydroxy alkyl esters have been found to perform as hydrogen sulfide scavengers. A method of scavenging hydrogen sulfide includes contacting a fluid containing hydrogen sulfide with a treatment fluid including an alpha-hydroxy alkyl ester. Accordingly, the alpha-hydroxy alkyl ester reacts with the hydrogen sulfide to reduce the amount of hydrogen sulfide in the fluid. A broad range of alpha-hydroxy alkyl esters are disclosed.

Claims (19)

1. A method of reducing the amount of hydrogen sulfide in a hydrocarbon-containing fluid, the method comprising:

contacting the hydrocarbon-containing fluid with a treatment fluid including at least one alpha-hydroxy alkyl ester, wherein the hydrogen sulfide reacts with the alpha-hydroxy alkyl ester to reduce an amount of the hydrogen sulfide in the hydrocarbon-containing fluid; and

wherein the alpha-hydroxy alkyl ester is selected from the group consisting of bis(hydroxymethyl) maleate; (2E, 4E)-hydroxymethyl hexa-2,4-dienoate; (E)-hydroxymethyl but-2-enoate; (E)-bis(hydroxymethyl) O,O′-(2-hydroxypropane-1,3-diyl) difumarate; hydroxymethyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate; and a combination thereof.

2. The method of claim 1 , wherein the reaction product is amine-free.

3. The method of claim 1 , wherein the treatment fluid includes between 5 and 20 volume percent of the alpha-hydroxy alkyl ester.

4. The method of claim 1 , wherein the treatment fluid includes between 10 and 15 volume percent of the alpha-hydroxy alkyl ester.

5. The method of claim 1 , wherein the treatment fluid includes a mixture of water and ethanol.

6. The method of claim 1 , wherein the hydrocarbon-containing fluid has been produced from a subterranean formation.

7. The method of claim 6 , wherein the hydrocarbon-containing fluid is a gas.

8. The method of claim 7 , wherein the contact between the hydrocarbon-containing fluid and the treatment fluid occurs in an absorption tower.

9. The method of claim 1 , wherein contacting the hydrocarbon-containing fluid with the treatment fluid including the at least one alpha-hydroxy alkyl ester comprises:

pumping the treatment fluid under pressure through a wellbore into a subterranean formation and maintaining the treatment fluid in the region around the wellbore for a predetermined period of time, wherein the alpha-hydroxy alkyl ester adsorbs onto the subterranean formation in a region around the wellbore; and

flowing the hydrocarbon-containing fluid from the subterranean formation into the wellbore, wherein the hydrogen sulfide reacts with the alpha-hydroxy alkyl ester as the hydrocarbon-containing fluid flows through the region around the wellbore to reduce an amount of hydrogen sulfide in the hydrocarbon-containing fluid before the hydrocarbon-containing fluid flows into the wellbore.

10. The method of claim 9 , wherein the treatment fluid is maintained in the region around the wellbore for a predetermined period of time to allow the alpha-hydroxy alkyl ester to absorb onto the subterranean formation.

11. The method of claim 1 , wherein the alpha-hydroxy alkyl ester comprises bis(hydroxymethyl) maleate.

12. The method of claim 1 , wherein the alpha-hydroxy alkyl ester comprises (2E, 4E)-hydroxymethyl hexa-2,4-dienoate.

13. The method of claim 1 , wherein the alpha-hydroxy alkyl ester comprises (E)-hydroxymethyl but-2-enoate.

14. The method of claim 1 , wherein the alpha-hydroxy alkyl ester comprises (E)-bis(hydroxymethyl) O,O′-(2-hydroxypropane-1,3-diyl) difumarate.

15. The method of claim 1 , wherein the alpha-hydroxy alkyl ester comprises hydroxymethyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate.

Assignments (6)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 17, 2025
From: JPMORGAN CHASE BANK, N.A.
To: CHAMPIONX LLC; APERGY ESP SYSTEMS, LLC; APERGY BMCS ACQUISITION CORP; HARBISON-FISCHER, INC.; NORRIS RODS, INC.,; NORRIS RODS, INC.,; NORRISEAL-WELLMARK, INC.; PCS FERGUSON, INC.; QUARTZDYNE, INC.; US SYNTHETIC CORPORATION
Reel/Frame 072004/0019 →
RELEASE OF SECURITY INTEREST Recorded Jun 7, 2022
From: BANK OF AMERICA, N.A.
To: CHAMPIONX USA INC.
Reel/Frame 060304/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 053849/0537 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 052848/0368 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 053250/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2014
From: MARTINEZ, AARON D.; MUKKAMALA, RAVINDRANATH; ACOSTA OTERO, ERICK J.; BAILEY, JOSEPH P.
To: ECOLAB USA INC.
Reel/Frame 033747/0753 →