IP Library Granted Patent US 11,603,497
Granted Patent B2
US 11,603,497 · App. 16/750,959 · Granted Mar 14, 2023

Synergized acetals composition and method for scavenging sulfides and mercaptans

Inventors: Antonio Pedro de Oliveira Felho (São Paulo, BR); Aline Yae Kina (São Paulo, BR); Grahame N. Taylor (Jersey Village, TX); Fabian Schneider (Eppelheim, DE); Julie Murison (Frankfurt, DE); Stefan Hauck (Alsbach-Haehnlein, DE); Mike Sahl (Bad Camberg, DE); Matthias Krull (Harxheim, DE); Jonathan James Wylde (The Woodlands, TX)
Assignee: CLARIANT INTERNATIONAL LTD
C10G29/24B01D53/52B01D53/78C02F1/20C09K8/532C10G29/20C10G29/22C10L3/103B01D53/1493B01D2251/21B01D2252/202B01D2252/205B01D2252/504B01D2256/24B01D2257/304B01D2257/306C02F2101/101C02F2103/10C09K2208/20C10G2300/1051C10G2300/207
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Quick Facts
Patent No.
US 11,603,497
App. No.
16/750,959
Granted
Mar 14, 2023
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 monosaccharide having 3 to 6 carbon atoms and/or an oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms 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 (73)

1. A process for the scavenging of hydrogen sulphide and/or mercaptans, comprising the step of adding to a medium comprising the 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 monosaccharide having 3 to 6 carbon atoms and/or an oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms and an aldehyde or ketone having one or two carbon atoms,

wherein the reaction products (I) and (II) are hemiacetals and/or acetals.

2. The process according to claim 1 , further comprising adding

(III) at least one reaction product from formaldehyde and ammonia and/or an amine, selected from the group consisting of primary alkyl amines having 1 to 10 carbon atoms, and primary hydroxy alkyl amines having 2 to 10 carbon atoms.

3. 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.

4. The process according to claim 1 , wherein the aldehyde or ketone for the reaction with the monohydric alcohol (I) contains 1 to 10 carbon atoms.

5. The process according to one claim 1 , wherein the aldehyde or ketone for the reaction with the monohydric alcohol (I) is selected from the group consisting of formaldehyde, paraformaldehyde, glyoxal, acetaldehyde, propionaldehyde, butyraldehyde and glutaraldehyde.

6. The process according to claim 1 , wherein the formaldehyde for the reaction with the monosaccharide having 3 to 6 carbon atoms and/or the oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms (group II) is selected from the group consisting of formaldehyde, paraformaldehyde, acetaldehyde and glyoxal.

7. The process according to claim 1 , wherein the aldehyde or ketone for both components (group I) and (group II) is formaldehyde.

8. The process according to claim 1 , wherein the monohydric alcohol comprises 1 to 15 carbon atoms.

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

10. 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.

11. The process according to claim 1 , wherein the monosaccharide having 3 to 6 carbon atoms and/or the oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms is a monosaccharide having 3 to 6 carbon atoms.

12. The process according to claim 1 , wherein the monosaccharide is a linear polyhydroxycarbonyl compound having the general formula (1)

C n (H 2 O) n   (1)

wherein n is an integer between 3 and 6.

13. The process according to claim 12 wherein n is between 4 and 6.

14. The process according to claim 13 wherein n is 5 or 6.

15. The process according to claim 1 , wherein the monosaccharide is a polyhydroxyaldehyde of formula (2)

CHO—(CH—OH) m —CH 2 OH  (2)

wherein m is 1, 2, 3 or 4.

16. The process according to claim 1 , wherein the monosaccharide is a polyhydroxyketone of formula (3)

HO—CH 2 —C(═O)—(CH—OH) p —CH 2 OH  (3)

wherein p is 0, 1, 2 or 3.

17. The process according to claim 1 , wherein the monosaccharide is a mixture of open-chain and cyclic form of the polyhydroxyaldehyde of formula (2) and the polyhydroxyketone according to formula (3).

18. The process according to claim 1 , wherein the monosaccharide is selected from the group consisting of glucose, mannose, galactose, ribose, arabinose, xylose and fructose.

19. The process according to claim 1 , wherein the monosaccharide having 3 to 6 carbon atoms and/or the oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms is an oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms.

20. The process according to claim 1 , wherein the oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms is a disaccharide being formed by dimerization of monosaccharides having 3 to 6 carbon atoms.

21. The process according to claim 20 , wherein the disaccharide formed by oligomerization of monosaccharides having 3 to 6 carbon atoms has the general formula (4)

C y (H 2 O) y-1   (4)

wherein y is 10, 11 or 12.

22. The process according to claim 20 , wherein the disaccharide is formed from aldoses and/or ketoses having 5 or 6 carbon atoms which are linked by a glycosidic linkage.

23. The process according to one or more of claim 19 , wherein the oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms is selected from maltose, Isomaltose, cellobiose, trehalose, sucrose, isomaltulose, trehalulose, lactose, lactulose and raffinose.

24. The process according to claim 2 , wherein the reaction product (III) of ammonia or an amine and formaldehyde corresponds to formula (7a)

wherein

R is H or methyl, and

n is 1 or 2.

25. The process according to claim 2 , wherein the reaction product (III) of an amine and formaldehyde corresponds to the formula (7b)

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

26. The process according to claim 24 , wherein the compound of formula 7a is 3,3′-methylenebis-5-methyl-oxazolidine.

27. The process according to one or more of claim 2 , wherein the reaction product (III) of an amine and formaldehyde is present in the composition in an amount from 1 wt.-% to 20 wt.-%.

28. The process according to claim 3 , 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 amines, aryl amines or alkylaryl amines

IV(c). hydroxy alkyl amines, hydroxy aryl amines 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

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.

29. The process according to claim 1 , comprising 1 to 60 wt.-% of the reaction product between a monohydric alcohol and an aldehyde or ketone.

30. The process according to claim 1 , comprising 1 to 95 wt.-% of the reaction product between a monosaccharide having 3 to 6 carbon atoms and/or an oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms and an aldehyde or ketone.

31. The process according to claim 1 , wherein the molar ratio between the reaction product between a monohydric alcohol and an aldehyde or ketone (group I) and the reaction product between a monosaccharide having 3 to 6 carbon atoms and/or an oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms and an aldehyde having one or two carbon atoms (group II) is between 20:1 and 1:20.

32. The process according to claim 2 , wherein the weight ratio between the combined reaction products of groups (I) and group (II) on the one hand side and the synergist (group III) on the other hand side is between 1000:1 and 5:1.

33. The process according to claim 3 , comprising 0.1 to 15 wt.-% of at least one solids suppression agent (group IV).

34. The process according to claim 1 , further comprising an alkyl dimethyl benzyl ammonium chloride according to formula (10) in an amount between 0.01 and 5 wt.-%

wherein R 9 is C 8 to C 18 alkyl.

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

36. The process according to claim 35 , 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.

37. The process according to claim 35 , wherein the demulsifier corresponds to the formula (8)

wherein

R 10 is C 2 to C 4 alkylene,

R 11 is C 1 to Cis alkyl,

k is a number from 1 to 200,

m is a number from 1 to 100.

38. The process according to claim 35 , wherein the demulsifier is dodecylbenezesulfonic acid (9)

39. The process according to claim 35 , wherein the demulsifier is a mixture of at least one compound of formula (8) and at least one compound of formula (9) in a weight ratio of from 5:1 to 1:5, preferably in a weight ratio of from 3:1 to 1:3.

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

10 to 99 wt.-% of 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 monosaccharide having 3 to 6 carbon atoms and/or an oligosaccharide being formed by oligomerization of monosaccharides having 3 to 6 carbon atoms and an aldehyde or ketone having one or two carbon atoms, wherein the reaction products I. and II. are hemiacetals and/or acetals, and

1 to 90 wt.-% of a solvent selected from the group consisting of water, methanol, ethanol, propan-1-ol, propan-2-ol, ethylene glycol, diethylene glycol, triethylene glycol, neopentyl glycol, 2-butoxyethanol, glycerol and their mixtures.

Assignments (7)
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 Jul 28, 2021
From: TAYLOR, GRAHAME; WYLDE, JONATHAN JAMES
To: CLARIANT CORPORATION
Reel/Frame 057010/0299 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2021
From: DE OLIVEIRA FILHO, ANTONIO PEDRO; KINA, ALINE
To: CLARIANT S.A.
Reel/Frame 057010/0495 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2021
From: KRULL, MATTHIAS; SAHL, MIKE; SCHNEIDER, FABIAN; MURISON, JULIE; HAUCK, STEFAN
To: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH
Reel/Frame 057010/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2021
From: CLARIANT CORPORATION
To: CLARIANT INTERNATIONAL LTD
Reel/Frame 057010/0944 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2021
From: CLARIANT S.A.
To: CLARIANT INTERNATIONAL LTD
Reel/Frame 057010/0972 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2021
From: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH
To: CLARIANT INTERNATIONAL LTD
Reel/Frame 057011/0010 →
Continuity (2)
Division 15853114 · Dec 27, 2017
Related Publication 20200157439A1 · May 21, 2020