CA2489739A1 - Diamine terminated primary amine-aldehyde sulfur converting compositions and methods for making and using same - Google Patents
Diamine terminated primary amine-aldehyde sulfur converting compositions and methods for making and using same Download PDFInfo
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- CA2489739A1 CA2489739A1 CA002489739A CA2489739A CA2489739A1 CA 2489739 A1 CA2489739 A1 CA 2489739A1 CA 002489739 A CA002489739 A CA 002489739A CA 2489739 A CA2489739 A CA 2489739A CA 2489739 A1 CA2489739 A1 CA 2489739A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/58—Treatment of water, waste water, or sewage by removing specified dissolved compounds
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/68—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/14—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S210/00—Liquid purification or separation
- Y10S210/902—Materials removed
- Y10S210/916—Odor, e.g. including control or abatement
Abstract
A new class of sulfur scavenging or converting compositions is disclosed comprising diamine terminated, amine-aldehyde adducts, where the adducts are substantially bimolecular amine-aldehyde adducts and the composition is substantially free of trimer and/or triazines. Methods for making and using the new class of sulfur scavenging or converting composition are also disclosed. A plot of weekly average water production (M3/day) versus production week shows the beneficial effect of using such a composition after optimization, adjusting amount based on noxious sulfur content, and after multi-point injection of the composition into well fluids.
Claims (34)
1. A sulfur scavenging composition comprising a diamine terminated reaction product of at least one aldehyde with at least one primary amine, where the reaction product includes substantially bimolecular amine-aldehyde adducts.
2. The composition of claim 1, wherein the composition includes a sufficient amount of the diamine to substantially eliminate aldehyde liberation upon heating.
3. The composition of claim 1 or 2, wherein the reaction product is substantially free of higher aldehyde-amine adducts.
4. The composition of claim 3, wherein the higher aldehyde-amine adducts are selected from the dimers, trimers, triazines and mixtures thereof.
5. The composition of any preceding claim, wherein the primary amines are selected from the group consisting of amines of the general formula:
R"NH2 where R" is a linear or branched alkyl, aryl, alkaryl, or aralkyl group having between about 1 and about 20 carbon atoms and where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties and/or nitrogen atoms can be in the form of tertiary amine or amide moieties, and one or more of the hydrogen atoms can be replaced by a fluorine atom or chlorine atom.
R"NH2 where R" is a linear or branched alkyl, aryl, alkaryl, or aralkyl group having between about 1 and about 20 carbon atoms and where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties and/or nitrogen atoms can be in the form of tertiary amine or amide moieties, and one or more of the hydrogen atoms can be replaced by a fluorine atom or chlorine atom.
6. The composition of any preceding claim, wherein the aldehydes are selected from the group consisting of aldehydes of the general formula:
R'-CHO
or aldehyde donors that generate such aldehydes, where R' is a hydrogen atom (H) or a linear or branched alkyl, aryl, alkaryl, or aralkyl group having between about 1 and about 20 carbon atoms and where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties and/or nitrogen atoms can be in the form of tertiary amine or amide moieties, and where one or more of the hydrogen atoms can be replaced by fluorine atoms and/or chlorine atoms.
R'-CHO
or aldehyde donors that generate such aldehydes, where R' is a hydrogen atom (H) or a linear or branched alkyl, aryl, alkaryl, or aralkyl group having between about 1 and about 20 carbon atoms and where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties and/or nitrogen atoms can be in the form of tertiary amine or amide moieties, and where one or more of the hydrogen atoms can be replaced by fluorine atoms and/or chlorine atoms.
7. The composition of any preceding claim, wherein the aldehydes are selected from the group consisting of the general formula:
R'-CHO
or aldehyde donors that generate such aldehydes, where R' is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, hexyls (linear or branched), hepyls, octyls, nonyls, decyls, phenyl, benzyl, methyl substituted phenyls, and mixtures or combinations thereof.
R'-CHO
or aldehyde donors that generate such aldehydes, where R' is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, hexyls (linear or branched), hepyls, octyls, nonyls, decyls, phenyl, benzyl, methyl substituted phenyls, and mixtures or combinations thereof.
8. The composition of any preceding claim, wherein the aldehydes are selected from the group consisting of formaldehyde, paraformaldehyde, arylaldehydes, methoxyaldehydes, hydroxyaldehydes or aldols, glyceraldehydes, vanillin, veratraldehyde, alloxan, noneal, 1-formyl piperdine, salicylaldehyde, citronella and mixtures or combinations thereof.
9. The composition of any preceding claim, wherein the aldehydes are selected from the group consisting of paraformaldehyde, paraldehyde, formaldehyde, acetaldehyde, glycolaldehyde, glyceraldehyde, hydroxymethyl glyceraldehyde, glyoxal, and methyl formcel (a hemi-acetal, 55 percent formaldehyde solution in methanol and methoxy-methanol or water), aldols, and mixtures or combinations thereof.
10. The composition of any preceding claim, wherein the diamines are selected from the group consisting of diamines of the general formula where R is linear or branched alkenyl groups having between about 1 and about carbon atoms, cycloalkenyl groups having between about 1 and about 20 carbon atoms, alkylcycloalkenyl groups having between about 1 and about 20 carbon atoms, alka arenyl group having between about 1 and about 20 carbon atoms, ara alkenyl group having between about 1 and about 20 carbon atoms and mixtures or combinations thereof, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties and/or nitrogen atoms can be in the form of tertiary amine or amide moieties, and where one or more of the hydrogen atoms can be replaced by fluorine atoms and/or chlorine atoms.
11. The composition of any preceding claim, wherein the primary amine is methyl amine, the aldehyde is formaldehyde and the diamine is amine heads.
12. A composition for converting noxious sulfur species to high molecular weight sulfur species comprising at least one compound of formula (I):
where R is an alkenyl group, cycloalkenyl or arenyl group having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties and/or nitrogen atoms can be in the form of tertiary amine or amide moieties, R' and R" are the same or different carbon-containing groups having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties or nitrogen atoms in the form of tertiary amine and/or nitrogen-containing groups in the form of amide moieties and where k, 1, m and n are integers having a value between 0 and 2, provided that at least one has a value of 1 or 2.
where R is an alkenyl group, cycloalkenyl or arenyl group having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties and/or nitrogen atoms can be in the form of tertiary amine or amide moieties, R' and R" are the same or different carbon-containing groups having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties or nitrogen atoms in the form of tertiary amine and/or nitrogen-containing groups in the form of amide moieties and where k, 1, m and n are integers having a value between 0 and 2, provided that at least one has a value of 1 or 2.
13. The composition of claim 12, wherein the composition includes a sufficient amount of the diamine to substantially eliminate the liberation of aldehyde upon heating and wherein the composition includes substantially no higher aldehyde-amine adducts.
14. The composition of claim 12 or 13, wherein R" is a methyl group, R' is H, and R
is a cycloalkenyl group associated with diamines in amine heads.
is a cycloalkenyl group associated with diamines in amine heads.
15. A method for preparing sulfur scavenging compositions including the steps of:
contacting at least one aldehyde with at least one primary amine under conditions to form a reaction product comprising substantially bimolecular adducts of the amines and the aldehydes having substantially no trimer or triazine adducts; and contacting the reaction product with at least one diamine to form a final reaction product comprising at least one compound of formula (I):
where R is an alkenyl group, cycloalkenyl or arenyl group having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy, and/or ether moieties and/or nitrogen atoms in the form of tertiary amine and/or amide moieties, R' and R" are the same or different carbon-containing groups having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties or nitrogen atoms in the form of tertiary amine and/or nitrogen-containing groups in the form of amide moieties and where k, l, m and n are integers having a value between 0 and 2, provided that at least one has a value of 1 or 2.
contacting at least one aldehyde with at least one primary amine under conditions to form a reaction product comprising substantially bimolecular adducts of the amines and the aldehydes having substantially no trimer or triazine adducts; and contacting the reaction product with at least one diamine to form a final reaction product comprising at least one compound of formula (I):
where R is an alkenyl group, cycloalkenyl or arenyl group having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy, and/or ether moieties and/or nitrogen atoms in the form of tertiary amine and/or amide moieties, R' and R" are the same or different carbon-containing groups having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of carboxy, hydroxy and/or ether moieties or nitrogen atoms in the form of tertiary amine and/or nitrogen-containing groups in the form of amide moieties and where k, l, m and n are integers having a value between 0 and 2, provided that at least one has a value of 1 or 2.
16. The method of claim 15, wherein the diamine is added in an amount sufficient to substantially eliminate aldehyde liberation upon heating.
17. The method of claim 15 or 16, further comprising the step of:
contacting the final reaction product with a reducing agent to convert any imine by-products in the final reaction product to their corresponding saturated analogs.
contacting the final reaction product with a reducing agent to convert any imine by-products in the final reaction product to their corresponding saturated analogs.
18. The method of claim 17, wherein the reducing agent is sodium borohydride.
19. The method of any one of claims 15 to 18, wherein R" is a methyl group, R' is H, and R is a cycloalkenyl group associated with diamines in amine heads.
20. A method comprising the step of:
contacting a fluid or fluid stream including noxious sulfur species with an effective amount of a sulfur scavenging or converting composition including a compound of formula (I):
where R is an alkenyl group having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of ether, hydroxy or carboxy moieties and/or nitrogen atoms in the form of tertiary amine or amide moieties or amide moieties, R' and R" are the same or different carbon-containing groups having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of ether, hydroxy or carboxy moieties and/or nitrogen atoms in the form of tertiary amine moieties or amide moieties, where k, l, m and n are integers having a value between 0 and 2, provided that at least one has a value of 1 or 2, where the composition does not liberate aldehyde upon heating and includes no or only trace amounts of triazines, and where the amount is sufficient to reduce, to reduce below a target level or to substantially eliminate the noxious sulfur species.
contacting a fluid or fluid stream including noxious sulfur species with an effective amount of a sulfur scavenging or converting composition including a compound of formula (I):
where R is an alkenyl group having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of ether, hydroxy or carboxy moieties and/or nitrogen atoms in the form of tertiary amine or amide moieties or amide moieties, R' and R" are the same or different carbon-containing groups having between about 1 and about 20 carbon atoms, where one or more of the carbon atoms can be oxygen atoms in the form of ether, hydroxy or carboxy moieties and/or nitrogen atoms in the form of tertiary amine moieties or amide moieties, where k, l, m and n are integers having a value between 0 and 2, provided that at least one has a value of 1 or 2, where the composition does not liberate aldehyde upon heating and includes no or only trace amounts of triazines, and where the amount is sufficient to reduce, to reduce below a target level or to substantially eliminate the noxious sulfur species.
21. The method of claim 20, wherein R" is a methyl group, R' is H, and R is an cycloalkenyl group associated with diamines in amine heads.
22. A method comprising the step of:
contacting a fluid or fluid stream including noxious sulfur species with an effective amount of a sulfur scavenging or converting composition comprising a diamine terminated reaction product of at least one aldehyde with at least one primary amine, where the reaction product includes substantially bimolecular amine-aldehyde adducts.
contacting a fluid or fluid stream including noxious sulfur species with an effective amount of a sulfur scavenging or converting composition comprising a diamine terminated reaction product of at least one aldehyde with at least one primary amine, where the reaction product includes substantially bimolecular amine-aldehyde adducts.
23. The method of claim 22, comprising treating the fluid or stream by said contacting.
24. The method of any one of claims 20 to 23, wherein the fluid or stream is associated with oil/gas field equipment, a refinery, an industrial facility or a waste management facility.
25. The method of claim 24, wherein the oil/gas field equipment are selected from the group consisting of a flowline, a separator, a tank, a line heater, a heater treater, and similar gas/oil handling processing equipment.
26. The method of any one of claims 20 to 25, comprising injecting the composition into the fluid or fluid stream.
27. The method of claim 26, wherein the injecting step includes atomizing the composition during injection.
28. The method of claim 26 or 27, comprising the step of:
injecting the composition into a well via capillary coiled tubing.
injecting the composition into a well via capillary coiled tubing.
29. The method of claim 28, wherein the well is an oil or gas well.
30. The method of claim 28 or 29, further comprising the steps of:
injecting the effective amount of the composition at multiple points down a depth of the well.
injecting the effective amount of the composition at multiple points down a depth of the well.
31. The method of any one of claims 20 to 30, further comprising the steps of:
measuring a level of noxious sulfur species in the fluid, where the effective amount is greater than or equal to about 1.5 times the measured level of noxious sulfur species.
measuring a level of noxious sulfur species in the fluid, where the effective amount is greater than or equal to about 1.5 times the measured level of noxious sulfur species.
32 32. The method of any one of claims 20 to 31, further comprising the steps of:
measuring a level of noxious sulfur species in the fluid, where the effective amount is greater than or equal to about 2.0 times the measured level of noxious sulfur species, and reducing the amount of the injected composition until the measured amount of noxious sulfur species it below a target value.
measuring a level of noxious sulfur species in the fluid, where the effective amount is greater than or equal to about 2.0 times the measured level of noxious sulfur species, and reducing the amount of the injected composition until the measured amount of noxious sulfur species it below a target value.
33. The method of any one of claims 20 to 32, wherein the composition includes a sufficient amount of diamine to substantially eliminate aldehyde liberation upon heating.
34. The method of claim 33, wherein the sulfur scavenging or converting composition further comprises a solvent.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/734,600 US7140433B2 (en) | 2003-12-12 | 2003-12-12 | Diamine terminated primary amine-aldehyde sulfur converting compositions and methods for making and using same |
US10/734,600 | 2003-12-12 |
Publications (2)
Publication Number | Publication Date |
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CA2489739A1 true CA2489739A1 (en) | 2005-06-12 |
CA2489739C CA2489739C (en) | 2012-06-19 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2489739A Active CA2489739C (en) | 2003-12-12 | 2004-12-10 | Diamine terminated primary amine-aldehyde sulfur converting compositions and methods for making and using same |
Country Status (5)
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US (2) | US7140433B2 (en) |
AU (1) | AU2004235671B2 (en) |
CA (1) | CA2489739C (en) |
GB (1) | GB2409202B (en) |
NO (1) | NO335445B1 (en) |
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