IP Library Granted Patent US 11,118,097
Granted Patent B2
US 11,118,097 · App. 15/852,777 · Granted Sep 14, 2021

Synergized hemiacetals composition and method for scavenging sulfides and mercaptans

Inventors: Antonio Pedro de Oliveira Filho (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.
C09K8/532B01D53/52B01D53/78C02F1/20C10G21/16C10G21/20C10G29/20C10G29/22C10G33/04B01D53/1493B01D2251/21B01D2252/202B01D2252/205B01D2252/504B01D2256/24B01D2257/304B01D2257/306C02F2101/101C02F2103/10C10G2300/202C10G2300/207
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Quick Facts
Patent No.
US 11,118,097
App. No.
15/852,777
Granted
Sep 14, 2021
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 sugar 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 (69)

1. 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 sugar alcohol and an aldehyde or ketone wherein the reaction products I. and II. are hemiacetals and/or acetals.

2. The composition according to claim 1 , further comprising

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 composition according to claim 1 , further comprising

IV. at least one inorganic or organic alkaline compound that functions as a solids suppression agent.

4. The composition according to claim 1 wherein the aldehyde or ketone contains 1 to 10 carbon atoms.

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

6. The composition according to claim 1 , wherein the aldehyde or ketone is formaldehyde.

7. The composition according to claim 1 , wherein the monohydric alcohol comprises 1 to 15 carbon atoms.

8. The composition according to claim 1 , wherein the monohydric alcohol is an aliphatic alcohol.

9. The composition 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.

10. The composition according to claim 1 , wherein the sugar alcohol is a polyol obtainable by reduction of a sugar.

11. The composition according to claim 1 , wherein the sugar alcohol contains 4 to 12 carbon atoms and 4 to 10 hydroxy groups wherein not more than one hydroxy group is attached to each carbon atom.

12. The composition according to claim 1 , wherein the sugar alcohol is selected from tetritols, pentitols and hexitols.

13. The composition according to claim 1 , wherein the sugar alcohol is selected from the group consisting of erythritol, threitol, arabitol, ribitol, xylitol, allitol, dulcitol, sorbitol, iditol, mannitol, talitol, inositol.

14. The composition according to claim 1 , wherein the sugar alcohol is a linear sugar alcohol having the general formula (1)

HO—CH 2 —(CHOH) n —CH 2 —OH  (1)

wherein n is 2, 3 or 4.

15. The composition according to claim 1 , wherein the reaction product between a sugar alcohol and an aldehyde or ketone is selected from the group consisting of:

OHCHR 1 —O—CH 2 —CH(OCHR 1 OH)—CH(OCHR 1 OH)—CH(OCHR 1 OH)—CH(OCHR 1 OH)—CH 2 —O—CHR 1 OH  (2),

OHCHR 1 —O—CH 2 —CH(OCHR 1 OH)—CHOH—CH(OCHR 1 OH)—CH(OCHR 1 OH)—CH 2 —O—CHR 1 OH  (3),

OHCHR 1 —O—CH 2 —CH(OCHR 1 OH)—CHOH—CH(OCHR 1 OH)—CHOH—CH 2 —O—CHR 1 OH   (4),

and OH—CH 2 —CH(OCHR 1 OH)—CHOH—CH(OCHR 1 OH)—CHOH—CH 2 —O—CHR 1 OH   (5),

wherein R 1 is H or C 1 to C 9 alkyl.

16. The composition according to claim 1 , wherein the reaction product III of an amine and formaldehyde corresponds to formula (6a)

wherein

R is H or methyl, and

n is 1 or 2.

17. The composition according to claim 1 , wherein the reaction product III of an amine and formaldehyde corresponds to the formula (6b)

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

18. The composition according to claim 16 , wherein the compound of formula 6a is 3,3′-methylenebis-5-methyl-oxazolidine.

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

20. The composition 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, 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.

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

22. The composition according to claim 1 , comprising 1 to 95 wt.-% of the reaction product between a sugar alcohol and an aldehyde or ketone.

23. The composition 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 sugar alcohol and an aldehyde or ketone (group II) is between 20:1 and 1:20.

24. The composition according to claim 2 , wherein the ratio between the combined reaction products of group I and group II on the one hand side and the at least one reaction product from formaldehyde and ammonia and/or an amine of group III on the other hand side is between 1000:1 and 5:1.

25. Composition according to claim 1 , comprising 0.1 to 15 wt. % of at least one solids suppression agent (group IV).

26. A composition comprising

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

II. at least one reaction product between a sugar alcohol and an aldehyde or ketone wherein the reaction products I. and II. are hemiacetals and/or acetals, and

an alkyl dimethyl benzyl ammonium chloride according to formula (9) as a corrosion inhibitor

wherein R 9 is C 8 to C 18 alkyl.

27. The composition according to claim 26 , wherein the compound of formula (9) is present in an amount between 0.01 and 5 wt. %.

28. A composition comprising

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

II. at least one reaction product between a sugar alcohol and an aldehyde or ketone wherein the reaction products I. and II. are hemiacetals and/or acetals, and

a demulsifier in an amount between 0.1 to 10 wt. %.

29. The composition according to claim 28 , 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.

30. The composition according to claim 28 , wherein the demulsifier corresponds to the formula (7)

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.

31. The composition according to claim 28 , wherein the demulsifier is dodecylbenezesulfonic acid (8)

32. The composition according to claim 28 , wherein the demulsifier is a mixture of at least one compound of formula (7) and at least one compound of formula (8) in a weight ratio of from 5:1 to 1:5.

33. A formulation, comprising 10 to 99 wt.-% of a composition according to claim 1 , 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.

34. A process for the scavenging of hydrogen sulphide and/or mercaptans, comprising the step of 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 sugar alcohol and an aldehyde or ketone wherein the reaction products I. and II. are hemiacetals and/or acetals.

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 Oct 1, 2018
From: TAYLOR, GRAHAME; WYLDE, JONATHAN JAMES
To: CLARIANT CORPORATION
Reel/Frame 047024/0253 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2018
From: 05/02/2018DE OLIVEIRA FILHO, ANTONIO PEDRO; KINA, ALINE
To: CLARIANT S.A.
Reel/Frame 047024/0552 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2018
From: KRULL, MATTHIAS; SAHL, MIKE; MURISON, JULIE; HAUCK, STEFAN; SCHNEIDER, FABIAN
To: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH
Reel/Frame 047025/0595 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2018
From: CLARIANT CORPORATION
To: CLARIANT INTERNATIONAL LTD.
Reel/Frame 047025/0804 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2018
From: CLARIANT S.A.
To: CLARIANT INTERNATIONAL LTD.
Reel/Frame 047025/0855 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2018
From: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH
To: CLARIANT INTERNATIONAL LTD.
Reel/Frame 047025/0873 →
Continuity (1)
Related Publication 20190194523A1 · Jun 27, 2019