IP Library Granted Patent US 11,530,347
Granted Patent B2
US 11,530,347 · App. 16/313,002 · Granted Dec 20, 2022

Synergized acetals composition and method for scavenging sulfides and mercaptans

Inventors: Antonio Pedro De Oliveira Filho (The Woodlands, TX); Aline Kina (Rio de Janeiro, BR); Grahame Taylor (Jersey Village, TX); Jonathan Wylde (The Woodlands, TX); James Begeal (Cibolo, TX); Ali Yousef (San Antonio, TX); Matthias Krull (Harxheim, DE); Mike Sahl (Bad Camberg, DE)
Assignee: Clariant International Ltd
C09K8/54C09K8/035C09K8/532C09K8/86C10G29/22C10G29/24C09K2208/20C09K2208/32C10G2300/202C10G2300/207
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Quick Facts
Patent No.
US 11,530,347
App. No.
16/313,002
Granted
Dec 20, 2022
Kind
B2
Abstract

This invention provides a composition comprising I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and II. at least one reaction product between a nitrogen-free polyhydric alcohol and an aldehyde or ketone, and optionally III. at least one reaction product from III.a) formaldehyde, and III.b) an amine, selected from the group consisting of primary alkyl amines having 1 to 4 carbon atoms, and primary hydroxy alkyl amines having 2 to 4 carbon atoms, and optionally IV. at least one solid suppression agent selected from the group consisting of IV(a). alkali or alkaline earth metal hydroxides IV(b). mono-, di- or tri-hydroxy alkyl, aryl or alkylaryl amines, IV(c). mono-, di- or tri-alkyl, aryl or alkylaryl primary, secondary and tertiary amines or IV(d). multifunctional amines and IV(e). mixtures of compounds of groups IV(a) to IV(c). wherein alkyl is C 1 to C 15 , aryl is C 6 to C 15 and alkylaryl is C 7 to C 15 .

Claims (86)

1. A process for the scavenging of hydrogen sulphide and/or mercaptans, comprising adding to a medium comprising such hydrogen sulphide or mercaptans a composition comprising

I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and

II. at least one reaction product between a nitrogen-free polyhydric alcohol and an aldehyde or ketone, wherein

the reaction products I. and II. are selected from the group consisting of hem iacetals and acetals, and

the aldehyde or ketone contains 1 to 10 carbon atoms, and

the monohydric alcohol comprises 1 to 15 carbon atoms, and

the polyhydric alcohol contains 2 to 20 carbon atoms and 2 to 6 hydroxy groups.

2. The process according to claim 1 , wherein the scavenging occurs from fluids or gases produced from subterranean formations.

3. The process according to claim 1 , wherein the scavenging from gas is conducted in a contact tower or by direct injection into the gas.

4. The process according to claim 1 , further comprising adding III. at least one reaction product from formaldehyde and a compound selected from the group consisting of ammonia and an amine, the amine being selected from the group consisting of primary alkyl amines having 1 to 4 carbon atoms, and primary hydroxy alkyl amines having 2 to 4 carbon atoms.

5. The process according to claim 1 , further comprising adding IV. at least one inorganic or organic alkaline compound that functions as a solids suppression agent.

6. The process according to claim 5 , wherein the alkaline compound IV. is selected from the group consisting of

IV(a) alkaline metal salts or alkaline earth metal salts

IV(b) ammonia; alkyl, aryl or alkylaryl amines

IV(c) hydroxy alkyl, hydroxyl aryl or hydroxy alkylaryl amines

IV(d) multifunctional amines containing besides an amino group, at least one further functional group selected from the group consisting of amino groups, ether groups and acid groups or an ester, amide or salt thereof, and

IV(e) mixtures of compounds of groups IV(a) to IV(c) wherein “alkyl” means C 1 to C 20 alkyl, “aryl” means C 6 to C 20 aryl and “alkylaryl” means C 7 to C 20 alkylaryl.

7. The process according to claim 1 , wherein the aldehyde or ketone contains 1 to 4 carbon atoms.

8. The process according to claim 1 , wherein the aldehyde or ketone is selected from the group consisting of formaldehyde, paraformaldehyde, glyoxal, acetaldehyde, propionaldehyde, butyraldehyde and glutaraldehyde.

9. The process according to claim 1 , wherein the aldehyde or ketone is formaldehyde.

10. The process according to claim 1 , wherein the monohydric alcohol comprises 1 to 5 carbon atoms.

11. The process according to claim 1 , wherein the monohydric alcohol is an aliphatic alcohol.

12. The process according to claim 1 , wherein the monohydric alcohol is selected from the group consisting of methanol, ethanol, propanol, iso-propanol, n-butanol, iso-butanol, tert-butanol, pentanol, hexanol, heptanol and octanol, and any mixture thereof.

13. The process according to claim 1 , wherein the polyhydric alcohol is selected from the group consisting of monoethyleneglycol, diethylene glycol, triethylene glycol propylene glycol, butylene glycol, neopentyl glycol, pentaerythritol, glycerol and oligomers of glycerol.

14. The process according to claim 1 , wherein the reaction product between a polyhydric alcohol and an aldehyde or ketone is selected from the group consisting of the compounds of formulae (2) to (5)

wherein

p is a number from 2 to 10, and

R 1 is H or C 1 to C 8 alkyl, and

R 2 is CH 2 OH, and

wherein

R 3 and R 4 independently are H or CH 2 OH

wherein

m is 1 to 10, and

wherein

R 5 is H, CH 3 , (CH 2 ) z CH 3

z is 1 to 10

x is 1 to 5.

15. The process according to claim 14 , wherein m is 1 or 2.

16. The process according to claim 4 , wherein the reaction product III of an amine and formaldehyde corresponds to the formula (1b)

wherein each R 1 is C 1 to C 4 alkyl or C 2 to C 4 hydroxy alkyl.

17. The process according to claim 4 , wherein the reaction product III of an amine and formaldehyde corresponds to formula (1a)

wherein

R is H or methyl, and

n is 1 or 2.

18. The process according to claim 17 , wherein the compound of formula 1a is 3,3′-methylenebis-5-methyl-oxazolidine.

19. The process according to claim 4 , wherein the reaction product III of an amine and formaldehyde is present in the process in an amount from 1 wt.-% to 20 wt.-%.

20. The process according to claim 1 , further comprising an alkyl dimethyl benzyl ammonium chloride according to formula (8) as a corrosion inhibitor

wherein R 9 is C 8 to C 18 alkyl.

21. The process according to claim 1 , wherein the compound of formula (8) is present in an amount between 0,01 and 5 wt.-%.

22. The process according to claim 1 , further comprising a demulsifier in an amount between 0.1 to 10 wt.-%.

23. The process according to claim 22 , wherein the demulsifier is selected from the group consisting of polysorbates, fatty alcohols, polymers comprising ethylene oxide, polymers comprising propylene oxide, ethylene oxide-propylene oxide copolymers, alkyl polyglucosides, alkylphenol ethoxylates, alkyl polyethylene oxide, alkylbenzenesulfonic acid and ethoxylated and/or propoxylated alkyl phenol-formaldehyde resins.

24. The process according to claim 22 , wherein the demulsifier corresponds to the formula (6)

wherein

R 10 is C 2 to C 4 alkylene,

R 11 is C 1 to C 18 alkyl,

k is a number from 1 to 200,

m is a number from 1 to 100.

25. The process according to claim 22 , wherein the demulsifier is dodecylbenezesulfonic acid

26. The process according to claim 22 , wherein the demulsifier is a mixture of at least one compound of formula (6) and at least one compound of formula (7) in a weight ratio of from 5:1 to 1:5.

27. The process according to claim 1 , comprising 1 to 50 wt. % of the reaction product between a monohydric alcohol and an aldehyde or ketone.

28. The process according to claim 1 , comprising 1 to 95 wt. % of the reaction product between a polyhydric alcohol and an aldehyde or ketone.

29. The process according to claim 1 , comprising 0.1 to 10 wt.-% of at least one solids suppression agent.

30. The process according to claim 1 , comprising water ad 100 wt.-%.

31. A process for synergizing the reaction between hydrogen sulphide and/or a mercaptan and a composition comprising

I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and

II. at least one reaction product between a nitrogen-free polyhydric alcohol and an aldehyde or ketone,

wherein the reaction products I. and II. are hem iacetals and/or acetals, and

the aldehyde or ketone contains 1 to 10 carbon atoms, and

the monohydric alcohol comprises 1 to 15 carbon atoms, and

the polyhydric alcohol contains 2 to 20 carbon atoms and 2 to 6 hydroxy groups, comprising the step of adding a reaction product from formaldehyde and a compound selected from the group consisting of ammonia and an amine, the amine being selected from the group consisting of primary alkyl amines having 1 to 4 carbon atoms, and primary hydroxy alkyl amines having 2 to 4 carbon atoms, to the reaction between the hydrogen sulphide and/or a mercaptan and a composition comprising

I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and

II. at least one reaction product between a nitrogen-free polyhydric alcohol and an aldehyde or ketone,

wherein the reaction products I. and II. are hem iacetals and/or acetals, and the aldehyde or ketone contains 1 to 10 carbon atoms, and the monohydric alcohol comprises 1 to 15 carbon atoms, and the polyhydric alcohol contains 2 to 20 carbon atoms and 2 to 6 hydroxy groups.

32. A process for solids suppression in the reaction between between hydrogen sulphide and/or mercaptans and a composition comprising

I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and

II. at least one reaction product between a nitrogen-free polyhydric alcohol and an aldehyde or ketone,

wherein the reaction products I. and II. are hem iacetals and/or acetals, and

the aldehyde or ketone contains 1 to 10 carbon atoms, and

the monohydric alcohol comprises 1 to 15 carbon atoms, and

the polyhydric alcohol contains 2 to 20 carbon atoms and 2 to 6 hydroxy groups, comprising the step of adding an inorganic or organic alkaline compound to the reaction between between hydrogen sulphide and/or mercaptans and a composition comprising

I. at least one reaction product between a nitrogen-free monohydric alcohol and an aldehyde or ketone, and

II. at least one reaction product between a nitrogen-free polyhydric alcohol and an aldehyde or ketone,

wherein the reaction products I. and II. are hem iacetals and/or acetals, and

the aldehyde or ketone contains 1 to 10 carbon atoms, and

the monohydric alcohol comprises 1 to 15 carbon atoms, and

the polyhydric alcohol contains 2 to 20 carbon atoms and 2 to 6 hydroxy groups.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 1, 2024
From: CLARIANT INTERNATIONAL LTD
To: DORF KETAL ENERGY SERVICES LLC
Reel/Frame 068157/0195 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2021
From: CLARIANT S.A.
To: CLARIANT INTERNATIONAL LTD
Reel/Frame 058561/0831 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 22, 2018
From: OLIVEIRA FILHO, ANTONIO PEDRO DE; KINA, ALINE; TAYLOR, GRAHAME; WYLDE, JONATHAN; BEGEAL, JAMES; YOUSEF, ALI; KRULL, MATTHIAS; SAHL, MIKE
To: CLARIANT INTERNATIONAL LTD.; CLARIANT S.A.
Reel/Frame 047847/0770 →
Continuity (5)
Continuation 15200390 · Jul 1, 2016
Continuation 15200471 · Jul 1, 2016
Continuation 15467688 · Mar 23, 2017
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