CA2148849A1 - Methode pour traiter des hydrocarbures gazeux et liquides acides - Google Patents
Methode pour traiter des hydrocarbures gazeux et liquides acidesInfo
- Publication number
- CA2148849A1 CA2148849A1 CA 2148849 CA2148849A CA2148849A1 CA 2148849 A1 CA2148849 A1 CA 2148849A1 CA 2148849 CA2148849 CA 2148849 CA 2148849 A CA2148849 A CA 2148849A CA 2148849 A1 CA2148849 A1 CA 2148849A1
- Authority
- CA
- Canada
- Prior art keywords
- triazine
- hexahydro
- solvent
- water
- fluid
- 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.)
- Abandoned
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 18
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 18
- 239000007788 liquid Substances 0.000 title claims abstract description 17
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 57
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000012530 fluid Substances 0.000 claims abstract description 13
- 230000002000 scavenging effect Effects 0.000 claims abstract description 7
- LMRUOCNRUILLIO-UHFFFAOYSA-N 1-(1,3-dimethoxypropyl)-3-methoxy-1,3,5-triazinane Chemical compound COCCC(OC)N1CNCN(OC)C1 LMRUOCNRUILLIO-UHFFFAOYSA-N 0.000 claims abstract description 3
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 claims description 53
- 239000002904 solvent Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- -1 alkoxyalkyl amine Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- BYWNSSMFBBZKMO-UHFFFAOYSA-N 1,3,5-tris(3-methoxypropyl)-1,3,5-triazinane Chemical group COCCCN1CN(CCCOC)CN(CCCOC)C1 BYWNSSMFBBZKMO-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 abstract description 24
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 33
- 239000003921 oil Substances 0.000 description 19
- 229960004279 formaldehyde Drugs 0.000 description 17
- 235000019256 formaldehyde Nutrition 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000003350 kerosene Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229940031098 ethanolamine Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- LPUBRQWGZPPVBS-UHFFFAOYSA-N 3-butoxypropan-1-amine Chemical compound CCCCOCCCN LPUBRQWGZPPVBS-UHFFFAOYSA-N 0.000 description 2
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- BVOMRRWJQOJMPA-UHFFFAOYSA-N 1,2,3-trithiane Chemical compound C1CSSSC1 BVOMRRWJQOJMPA-UHFFFAOYSA-N 0.000 description 1
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 1
- GQCPFUGDGIGHGH-UHFFFAOYSA-N 1,3,5-tris(3-butoxypropyl)-1,3,5-triazinane Chemical compound CCCCOCCCN1CN(CCCOCCCC)CN(CCCOCCCC)C1 GQCPFUGDGIGHGH-UHFFFAOYSA-N 0.000 description 1
- FUVJISLFUKMLOM-UHFFFAOYSA-N 1,3,5-tris(3-ethoxypropyl)-1,3,5-triazinane Chemical compound CCOCCCN1CN(CCCOCC)CN(CCCOCC)C1 FUVJISLFUKMLOM-UHFFFAOYSA-N 0.000 description 1
- XAUKFYNJOQWUPI-UHFFFAOYSA-N 1,3,5-tris(5-methoxypentyl)-1,3,5-triazinane Chemical compound COCCCCCN1CN(CCCCCOC)CN(CCCCCOC)C1 XAUKFYNJOQWUPI-UHFFFAOYSA-N 0.000 description 1
- OTEIVUGRPOAACM-UHFFFAOYSA-N 1,3-dimethoxy-5-(1-methoxyethyl)-1,3,5-triazinane Chemical compound COC(C)N1CN(OC)CN(OC)C1 OTEIVUGRPOAACM-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- DMRHQYSRQGGRCK-UHFFFAOYSA-N 5-methoxypentan-1-amine Chemical compound COCCCCCN DMRHQYSRQGGRCK-UHFFFAOYSA-N 0.000 description 1
- NIVRKESSQXJDNU-UHFFFAOYSA-N N1=NN=CC=C1.N1=NN=CC=C1.N1=NN=CC=C1 Chemical compound N1=NN=CC=C1.N1=NN=CC=C1.N1=NN=CC=C1 NIVRKESSQXJDNU-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/04—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/20—Nitrogen-containing compounds
-
- 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
- C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
- C10G70/04—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00 by physical processes
- C10G70/06—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00 by physical processes by gas-liquid contact
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26445394A | 1994-06-23 | 1994-06-23 | |
| US264,453 | 1994-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2148849A1 true CA2148849A1 (fr) | 1995-12-24 |
Family
ID=23006139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2148849 Abandoned CA2148849A1 (fr) | 1994-06-23 | 1995-05-08 | Methode pour traiter des hydrocarbures gazeux et liquides acides |
Country Status (5)
| Country | Link |
|---|---|
| AU (1) | AU2182195A (fr) |
| CA (1) | CA2148849A1 (fr) |
| DK (1) | DK71595A (fr) |
| GB (1) | GB2290542A (fr) |
| NO (1) | NO952145L (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7211665B2 (en) | 2001-11-09 | 2007-05-01 | Clearwater International, L.L.C. | Sulfide scavenger |
| US8562820B2 (en) | 2001-11-09 | 2013-10-22 | Clearwater International, L.L.C. | Sulfide scavenger |
| US10703921B2 (en) | 2018-01-23 | 2020-07-07 | Xerox Corporation | Surface layer for electronic device |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2177408C (fr) * | 1995-06-06 | 2001-12-11 | Michael Callaway | Elimination du sulfure d'hydrogene a l'aide de trimeres de l-aminoethanol |
| CA2231659C (fr) | 1996-07-12 | 2003-12-23 | Baker Hughes Incorporated | Agent epurateur contenant des bisoxazolidines pour eliminer le sulfure d'hydrogene |
| US5830243A (en) * | 1997-09-11 | 1998-11-03 | The Lubrizol Corporation | Fuel compositions containing N-substituted perahydro-s triazines |
| US7438877B2 (en) * | 2006-09-01 | 2008-10-21 | Baker Hughes Incorporated | Fast, high capacity hydrogen sulfide scavengers |
| FR2942802B1 (fr) * | 2009-03-03 | 2012-06-01 | Total Raffinage Marketing | Composition reticulante sous forme de granule pour preparer des compositions bitume/elastomere reticulees |
| RU2455346C2 (ru) * | 2010-06-29 | 2012-07-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Антикоррозионная присадка к смазочным маслам |
| US20120012507A1 (en) * | 2010-07-14 | 2012-01-19 | Compton Dennis R | Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons |
| US20120012505A1 (en) * | 2010-07-14 | 2012-01-19 | Compton Dennis R | Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons |
| US20120012506A1 (en) * | 2010-07-14 | 2012-01-19 | Compton Dennis R | Method of removing hydrogen sulfide |
| US8512449B1 (en) * | 2010-12-03 | 2013-08-20 | Jacam Chemical Company 2013, Llc | Oil-soluble triazine sulfide scavenger |
| RU2453582C1 (ru) * | 2010-12-15 | 2012-06-20 | Вячеслав Михайлович Андрианов | Комплексный реагент для очистки жидких и газообразных сред от сероводорода и меркаптанов со свойствами дезинфицирующего средства |
| US9463989B2 (en) | 2011-06-29 | 2016-10-11 | Baker Hughes Incorporated | Synergistic method for enhanced H2S/mercaptan scavenging |
| US9278307B2 (en) | 2012-05-29 | 2016-03-08 | Baker Hughes Incorporated | Synergistic H2 S scavengers |
| WO2014069668A1 (fr) * | 2012-11-02 | 2014-05-08 | 住友化学株式会社 | Procédé de production d'un composé |
| CN113599990B (zh) * | 2021-07-13 | 2024-02-27 | 克拉玛依市杰德科技有限责任公司 | 一种无水脱硫剂及其应用 |
| CN115569624B (zh) * | 2022-10-21 | 2023-12-19 | 广汉市福客科技有限公司 | 一种杂氮有机除硫剂的连续生产设备及生产方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3791974A (en) * | 1972-04-06 | 1974-02-12 | Ferro Corp | Bacterial spoilage inhibited metal working lubricant compositions |
| US5347004A (en) * | 1992-10-09 | 1994-09-13 | Baker Hughes, Inc. | Mixtures of hexahydrotriazines useful as H2 S scavengers |
-
1995
- 1995-05-08 CA CA 2148849 patent/CA2148849A1/fr not_active Abandoned
- 1995-05-31 NO NO952145A patent/NO952145L/no unknown
- 1995-06-20 GB GB9512461A patent/GB2290542A/en not_active Withdrawn
- 1995-06-21 AU AU21821/95A patent/AU2182195A/en not_active Abandoned
- 1995-06-22 DK DK71595A patent/DK71595A/da not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7211665B2 (en) | 2001-11-09 | 2007-05-01 | Clearwater International, L.L.C. | Sulfide scavenger |
| US8562820B2 (en) | 2001-11-09 | 2013-10-22 | Clearwater International, L.L.C. | Sulfide scavenger |
| US10703921B2 (en) | 2018-01-23 | 2020-07-07 | Xerox Corporation | Surface layer for electronic device |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9512461D0 (en) | 1995-08-23 |
| GB2290542A (en) | 1996-01-03 |
| NO952145L (no) | 1995-12-27 |
| NO952145D0 (no) | 1995-05-31 |
| DK71595A (da) | 1995-12-24 |
| AU2182195A (en) | 1996-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |