CA2603022A1 - Formulation for hydrogen sulphide scavenging from hydrocarbon streams and use thereof - Google Patents

Formulation for hydrogen sulphide scavenging from hydrocarbon streams and use thereof Download PDF

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Publication number
CA2603022A1
CA2603022A1 CA002603022A CA2603022A CA2603022A1 CA 2603022 A1 CA2603022 A1 CA 2603022A1 CA 002603022 A CA002603022 A CA 002603022A CA 2603022 A CA2603022 A CA 2603022A CA 2603022 A1 CA2603022 A1 CA 2603022A1
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Canada
Prior art keywords
formulation
triethylene glycol
weight
amine
hydrogen sulphide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002603022A
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French (fr)
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CA2603022C (en
Inventor
Thomas Robert Owens
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Canadian Energy Services LP
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Canwell Enviro-Industries Ltd
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Publication of CA2603022A1 publication Critical patent/CA2603022A1/en
Application granted granted Critical
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1456—Removing acid components
    • B01D53/1468—Removing hydrogen sulfide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1493—Selection of liquid materials for use as absorbents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/06—Polluted air

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Gas Separation By Absorption (AREA)
  • Treating Waste Gases (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A method has been developed for reducing the content of hydrogen sulphide in hydrocarbon streams. The method involves contacting a "sour" gas or fluid with a chemical formulation consisting of triethylene glycol and the reaction products of an amine and an aldehyde. The use of this method and chemical formulations produce spent products consisting of a single phase; thus alleviating problems associated with the deposition of dithiazine solids normally associated with triazine based scavengers. The method is especially useful for alleviating high temperature-induced dithiazine solids.

Claims (64)

1. Use of a hydrogen sulphide and mercaptan scavenging formulation for reducing amorphous dithiazine solids, said formulation comprising triethylene glycol and the reaction products of reacting a first amine and an aldehyde.
2. The use according to claim 1 wherein said first amine is monoethanolamine and the aldehyde is formaldehyde.
3. The use according to claim 1 or 2 wherein the weight of triethylene glycol is about 15%
to about 95%.
4. The use according to claim 1 or 2 wherein the weight of triethylene glycol is about 15%
to about 50%.
5. The use according to claim 1 or 2 wherein the weight of triethylene glycol is about 15%
to about 25%.
6. The use according to claim 2 wherein the reaction products comprise 2-[3,5-bis-(2-hydroxy-ethyl)-[1,3,5]triazinan-1-yl]-ethanol.
7. The use according to claim 1, further comprising a second amine, whereby the second amine is reacted with the first amine and the aldehyde.
8. The use according to claim 7, wherein the weight of triethylene glycol is about 15% to about 25%.
9. The use according to claim 8, wherein said second amine is diglycolamine.
10. A hydrogen sulphide and mercaptan scavenging formulation for reducing dithiazine solids in high temperature applications, said formulation comprising triethylene glycol and the reaction products of reacting a first amine, a second amine and an aldehyde.
11. The formulation according to claim 10 wherein said first amine is monoethanolamine and the aldehyde is formaldehyde.
12. The formulation according to claim 10 or 11 wherein the weight of triethylene glycol is about 15% to about 95%.
13. The formulation according to claim 10 or 11 wherein the weight of triethylene glycol is about 15% to about 50%.
14. The formulation according to claim 10 or 11 wherein the weight of triethylene glycol is about 15% to about 25%.
15. The formulation according to claim 11 wherein the reaction products comprise 2-[3,5-bis-(2-hydroxy-ethyl)-[1,3,5]triazinan-1-yl]-ethanol.
16. The formulation according to claim 10 or 11 wherein the weight of triethylene glycol is about 15% to about 50%.
17. The formulation according to claim 16, wherein the weight of triethylene glycol is about 15% to about 25%.
18. The formulation according to claim 11, wherein said second amine is diglycolamine.
19. Use of a mixture comprising triethylene glycol, and at least one triazine, as a hydrogen sulphide and mercaptan scavenging formulation for reducing amorphous dithiazine solids.
20. The use according to claim 19 wherein said triazine is 2-[3,5-bis-(2-hydroxy-ethyl)-[1,3,5]triazinan-1-yl]-ethanol.
21. The use according to claim 19 or 20 wherein the weight of triethylene glycol is about 15% to about 50%.
22. The use according to claim 19 or 20 wherein the weight of triethylene glycol is about 15% to about 25%.
23. A method for reducing the levels of hydrogen sulphide and mercaptans in hydrocarbon streams comprising contacting said streams with a formulation comprising triethylene glycol and the reaction products of reacting a first amine, a second amine and an aldehyde, and reacting said reaction products with hydrogen sulphide, thereby reducing the levels of hydrogen sulphide, mercaptans and solid dithiazine deposits.
24. The method according to claim 23 wherein the weight of triethylene glycol is about 15%
to about 95%.
25. The method according to claim 23, wherein said first amine is monoethanolamine and the aldehyde is formaldehyde.
26. The method according to claim 23 wherein the weight of triethylene glycol is about 15%
to about 75%.
27. The method according to claim 23 wherein the weight of triethylene glycol is about 15%
to about 50%.
28. The method according to claim 10 or 11 wherein the weight of triethylene glycol is about 15% to about 25%.
29. The method according to claim 23, wherein said second amine is diglycolamine.
30. The method according to claim 29 wherein the weight of triethylene glycol is about 15%
to about 25%.
31. The method according to claim 23 wherein the hydrocarbon stream is a gaseous or liquid stream.
32. The method according to claim 31 wherein the hydrocarbon stream is a sour natural gas stream.
33. The method according to any one of claims 23 to 32 wherein the level of hydrogen sulphide is reduced to a level of about 16 ppm or less.
34. The method according to any one of claims 23 to 32 wherein the hydrogen sulphide level is reduced to zero.
35. The method according to any one of claims 23 to 32 wherein said step of contacting reacts said formulation with hydrogen sulphide to form a spent formulation comprising a single phase.
36. The method according to any one of claims 23 to 32 wherein said step of contacting reacts said formulation with hydrogen sulphide to form a spent formulation comprising dithiazine.
37. The method of any one of claims 23 to 36 further comprising removing water from said stream subsequent to reducing the levels of hydrogen sulphide, mercaptans and solid dithiazine deposits.
38. A method for reducing the levels of hydrogen sulphide and mercaptans in high temperature hydrocarbon streams comprising contacting said streams with a formulation comprising triethylene glycol and the reaction products of reacting a first amine, a second amine and an aldehyde, and reacting said reaction products with hydrogen sulphide, thereby reducing the levels of hydrogen sulphide, mercaptans and solid dithiazine deposits.
39. The method according to claim 38 wherein the weight of triethylene glycol is about 15%
to about 95%.
40. The method according to claim 38, wherein said first amine is monoethanolamine and the aldehyde is formaldehyde.
41. The method according to claim 38 wherein the weight of triethylene glycol is about 15%
to about 75%.
42. The method according to claim 38 wherein the weight of triethylene glycol is about 15%
to about 50%.
43. The method according to claim 38 wherein the weight of triethylene glycol is about 15%
to about 25%.
44. The method according to claim 38, wherein said second amine is diglycolamine.
45. The method according to claim 44 wherein the weight of triethylene glycol is about 15%
to about 25%.
46. The method according to claim 38 wherein the hydrocarbon stream is a gaseous or liquid stream.
47. The method according to claim 46 wherein the hydrocarbon stream is a sour natural gas stream.
48. The method according to any one of claims 38 to 47 wherein the level of hydrogen sulphide is reduced to a level of about 16 ppm or less.
49. The method according to any one of claims 38 to 47 wherein the hydrogen sulphide level is reduced to zero.
50. The method according to any one of claims 38 to 47 wherein said step of contacting reacts said formulation with hydrogen sulphide to form a spent formulation comprising a single phase.
51. The method according to any one of claims 38 to 47 wherein said step of contacting reacts said formulation with hydrogen sulphide to form a spent formulation comprising dithiazine.
52. The method according to any one of claims 38 to 47 wherein said step of contacting reacts said formulation with hydrogen sulphide to form a spent formulation comprising dithiazine wherein the dithiazine may be a suspended amorphous solid or may be dissolved in said single phase.
53. The method according to any one of claims 38 to 47 wherein said step of contacting reacts said formulation with hydrogen sulphide to form a spent formulation comprising dithiazine, wherein said dithiazine deposits are minimized or eliminated.
54. The method of any one of claims 38 to 47 further comprising removing water from said stream subsequent to reducing the levels of hydrogen sulphide, mercaptans and solid dithiazine deposits.
55. The method of any one of claims 38 to 54 wherein said high temperature streams are above about 20°C.
56. The method of claim 55 wherein said high temperature streams are above about 30°C.
57. A hydrogen sulphide and mercaptan scavenging formulation for reducing dithiazine solids and not for dehydrating hydrocarbon streams, said formulation comprising triethylene glycol and the reaction products of reacting a first amine, a second amine and an aldehyde.
58. The formulation according to claim 57 wherein said first amine is monoethanolamine and the aldehyde is formaldehyde.
59. The formulation according to claim 57 or 58 wherein the weight of triethylene glycol is about 15% to about 95%.
60. The formulation according to claim 57 or 58 wherein the weight of triethylene glycol is about 15% to about 50%.
61. The formulation according to claim 57 or 58 wherein the weight of triethylene glycol is about 15% to about 25%.
62. The formulation according to claim 58 wherein the reaction products comprise 2-[3,5-bis-(2-hydroxy-ethyl)-[1,3,5]triazinan-1-yl]-ethanol.
63. The formulation according to claim 63, wherein the weight of triethylene glycol is about 15% to about 25%.
64. The formulation according to claim 57, wherein said second amine is diglycolamine.
CA2603022A 2006-10-26 2006-10-26 Formulation for hydrogen sulphide scavenging from hydrocarbon streams and use thereof Active CA2603022C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CA2006/001756 WO2008049188A1 (en) 2006-10-26 2006-10-26 Formulation for hydrogen sulphide scavenging from hydrocarbon streams and use thereof

Publications (2)

Publication Number Publication Date
CA2603022A1 true CA2603022A1 (en) 2008-02-13
CA2603022C CA2603022C (en) 2010-06-29

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WO (1) WO2008049188A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11584879B1 (en) 2021-12-21 2023-02-21 Halliburton Energy Services, Inc. Increasing scavenging efficiency of H2S scavenger by adding linear polymer
US11814576B2 (en) 2021-12-21 2023-11-14 Halliburton Energy Services, Inc. Increasing scavenging efficiency of H2S scavenger by adding linear polymer

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9296940B2 (en) 2009-12-21 2016-03-29 Baker Hughes Incorporated Dithiazine derivatives
US8022018B2 (en) 2009-12-21 2011-09-20 Baker Hughes Incorporated Quaternized dithiazines and method of using same in treatment of wells
US8354361B2 (en) 2009-12-21 2013-01-15 Baker Hughes Incorporated Method of using dithiazines and derivatives thereof in the treatment of wells
US8022017B2 (en) 2009-12-21 2011-09-20 Baker Hughes Incorporated Method of using dithiazine to inhibit corrosion
US8512449B1 (en) 2010-12-03 2013-08-20 Jacam Chemical Company 2013, Llc Oil-soluble triazine sulfide scavenger
US8920568B2 (en) 2011-03-28 2014-12-30 Baker Hughes Incorporated Method for the dissolution of amorphous dithiazine
RU2482163C1 (en) * 2012-03-12 2013-05-20 Ахматфаиль Магсумович Фахриев Hydrogen sulphide neutraliser, and method of its use
CA3193144A1 (en) 2020-09-25 2022-03-31 Tanhee GALINDO Nitrile solvents
EP4225973A1 (en) 2020-10-08 2023-08-16 Conocophillips Company Elemental sulfur dissolution and solvation
US11572514B2 (en) 2020-10-08 2023-02-07 Conocophillips Company Elemental sulfur dissolution and solvation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4978512B1 (en) * 1988-12-23 1993-06-15 Composition and method for sweetening hydrocarbons
US5980845A (en) * 1994-08-24 1999-11-09 Cherry; Doyle Regeneration of hydrogen sulfide scavengers
US5688479A (en) * 1994-12-22 1997-11-18 Uop Process for removing HCl from hydrocarbon streams
GB0031710D0 (en) * 2000-12-27 2001-02-07 Dyno Oil Field Chemicals Process for the reduction or elimination of hydrogen sulphide
US6582624B2 (en) * 2001-02-01 2003-06-24 Canwell Enviro-Industries, Ltd. Method and composition for removing sulfides from hydrocarbon streams

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11584879B1 (en) 2021-12-21 2023-02-21 Halliburton Energy Services, Inc. Increasing scavenging efficiency of H2S scavenger by adding linear polymer
US11814576B2 (en) 2021-12-21 2023-11-14 Halliburton Energy Services, Inc. Increasing scavenging efficiency of H2S scavenger by adding linear polymer

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Publication number Publication date
CA2603022C (en) 2010-06-29
WO2008049188A1 (en) 2008-05-02

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