IP Library Granted Patent US 10,442,755
Granted Patent B2
US 10,442,755 · App. 15/717,338 · Granted Oct 15, 2019

Preparation of new stable hydrogen sulfide scavengers useful in both water as well as oil medium applications

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Quick Facts
Patent No.
US 10,442,755
App. No.
15/717,338
Granted
Oct 15, 2019
Kind
B2
Abstract

The disclosure provides compositions and methods that are useful in removing, lowering, or otherwise controlling hydrogen sulfide and mercaptans. The compositions and methods can be used in any industry where hydrogen sulfide poses problems, such as when dealing with crude oil based, natural gas based, and/or coal based products. In some embodiments, the compositions include one or more alkoxylated amino formaldehyde adducts.

Claims (37)

1. A method of treating hydrogen sulfide in a stream, the method comprising:

adding an effective amount of a composition to the stream, wherein the composition comprises a scavenger, the scavenger comprising Formula I:

k=1-3, not=0

1=0-3

provided that when 1=0 R 6 ═R 5

provided that each N has at most one H

R 2 =

R 3 ═H, methyl, ethyl

R 4 ═H, methyl, ethyl

R 5 =optionally H, R 7 , or

R 7 =

m=0-4

provided that when m=0, R 5 ═H or R 7

n=0-4

R 5 ═H, methyl, ethyl, propyl

R 9 ═H, methyl, ethyl, propyl, CH 2 OR 10

R 10 ═H, methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl

R 11 ═H, methyl, ethyl

R 12 ═H, methyl, ethyl

R 6 =

p=0-2,

and reacting the hydrogen sulfide with the scavenger.

2. The method of claim 1 , wherein the scavenger comprises a structure selected from the group consisting of:

wherein each R is independently selected from a hydrogen, methyl, ethyl, propyl, and/or glycidyl ether (R 9 ═CH 2 OR 10 ), where R 10 ═H, methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl; and wherein each R 1 is independently selected from a hydrogen or methyl.

3. The method of claim 2 , wherein each R and R 1 is independently selected from a C 1 -C 14 hydrocarbon group or a hydrogen.

4. The method of claim 1 , wherein the scavenger comprises a structure selected from the group consisting of:

wherein each R is independently selected from a hydrogen, methyl, ethyl, propyl, and/or glycidyl ether (R 9 ═CH 2 OR 10 ), where R 10 ═H, methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl; and wherein each R 1 is independently selected from a hydrogen or methyl.

5. The method of claim 4 , wherein each R and R 1 independently comprises a C 1 -C 14 hydrocarbon group or a hydrogen.

6. The method of claim 1 , wherein the scavenger comprises a structure selected from the group consisting of

wherein each R is independently selected from a hydrogen, methyl, ethyl, propyl, and/or glycidyl ether (R 9 ═CH 2 OR 10 ), where R 10 ═H, methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl; and wherein each R 1 is independently selected from a hydrogen or methyl.

7. The method of claim 6 , wherein each R and R 1 independently comprise a C 1 -C 14 hydrocarbon group or a hydrogen.

8. The method of claim 1 , wherein the scavenger comprises a structure selected from the group consisting of

wherein each R is independently selected from a hydrogen, methyl, ethyl, propyl, and/or glycidyl ether (R 9 ═CH 2 OR 10 ), where R 10 ═H, methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl; and wherein each R 1 is independently selected from a hydrogen or methyl.

9. The method of claim 8 , wherein each R and R 1 independently comprises a C 1 -C 14 hydrocarbon group or a hydrogen.

10. The method of claim 1 , wherein the stream is aqueous, gaseous, organic, or any combination thereof.

11. The method of claim 1 , wherein the composition is anhydrous.

12. The method of claim 1 , wherein the composition comprises an aqueous solvent or an organic solvent.

Assignments (8)
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 Jan 28, 2021
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 055158/0707 →
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 →
CHANGE OF ADDRESS Recorded Sep 17, 2019
From: ECOLAB USA INC.
To: ECOLAB USA INC.
Reel/Frame 050410/0502 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2018
From: DE, SUBHASIS
To: ECOLAB USA INC.
Reel/Frame 047298/0122 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2017
From: ANANTANENI, PRAKASA RAO; HARRINGTON, RYAN MATTHEW; TARVERDI, DAVID; KARAS, LAWRENCE J.; MUKKAMALA, RAVINDRANATH
To: ECOLAB USA INC.
Reel/Frame 043719/0140 →