CA2805402C - Improved method of removing hydrogen sulfide - Google Patents
Improved method of removing hydrogen sulfide Download PDFInfo
- Publication number
- CA2805402C CA2805402C CA2805402A CA2805402A CA2805402C CA 2805402 C CA2805402 C CA 2805402C CA 2805402 A CA2805402 A CA 2805402A CA 2805402 A CA2805402 A CA 2805402A CA 2805402 C CA2805402 C CA 2805402C
- Authority
- CA
- Canada
- Prior art keywords
- nitroxide
- scavenger
- promoter
- methyltriazine
- alkyl
- 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.)
- Active
Links
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229910000037 hydrogen sulfide Inorganic materials 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 19
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000002516 radical scavenger Substances 0.000 claims abstract description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 21
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 21
- 239000012530 fluid Substances 0.000 claims abstract description 17
- 150000004820 halides Chemical class 0.000 claims abstract description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 3
- FXKQPQOOZSXQAG-UHFFFAOYSA-N 4-methyltriazine Chemical group CC1=CC=NN=N1 FXKQPQOOZSXQAG-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 13
- 230000002000 scavenging effect Effects 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 6
- -1 tri-substituted-hexahydro-s-triazines Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical class C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- BVOMRRWJQOJMPA-UHFFFAOYSA-N 1,2,3-trithiane Chemical compound C1CSSSC1 BVOMRRWJQOJMPA-UHFFFAOYSA-N 0.000 description 1
- VRXAFJHCDANCAR-UHFFFAOYSA-N 5-methyltriazine Chemical compound CC1=CN=NN=C1 VRXAFJHCDANCAR-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000008901 benefit Effects 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000010747 number 6 fuel oil Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 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
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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
-
- 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
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/207—Acid gases, e.g. H2S, COS, SO2, HCN
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/835,805 | 2010-07-14 | ||
| US12/835,805 US20120012506A1 (en) | 2010-07-14 | 2010-07-14 | Method of removing hydrogen sulfide |
| PCT/US2011/043780 WO2012009391A2 (en) | 2010-07-14 | 2011-07-13 | Improved method of removing hydrogen sulfide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2805402A1 CA2805402A1 (en) | 2012-01-19 |
| CA2805402C true CA2805402C (en) | 2018-03-13 |
Family
ID=45466087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2805402A Active CA2805402C (en) | 2010-07-14 | 2011-07-13 | Improved method of removing hydrogen sulfide |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20120012506A1 (enExample) |
| EP (1) | EP2593534A4 (enExample) |
| JP (1) | JP5815699B2 (enExample) |
| KR (1) | KR20130047738A (enExample) |
| CN (1) | CN103003395A (enExample) |
| AR (1) | AR082847A1 (enExample) |
| BR (1) | BR112013000887A2 (enExample) |
| CA (1) | CA2805402C (enExample) |
| MX (1) | MX2013000511A (enExample) |
| RU (1) | RU2562610C2 (enExample) |
| SG (1) | SG187080A1 (enExample) |
| WO (1) | WO2012009391A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9663390B2 (en) | 2013-05-10 | 2017-05-30 | Ecolab Usa Inc. | Reduction of hydrogen sulfide and/or malodor gassing from water via the addition of peroxyacetic acid/hydrogen peroxide product |
| CN105056710B (zh) * | 2015-08-21 | 2017-05-24 | 胜利油田胜利化工有限责任公司 | 一种用于脱除油气中硫化氢的液体吸收剂 |
| CN107502329B (zh) * | 2016-06-14 | 2020-07-10 | 中国石油大学(华东) | 一种清除稠油热采中伴生硫化氢气体的消除剂 |
| WO2018003623A1 (ja) * | 2016-06-28 | 2018-01-04 | 株式会社クラレ | 含硫黄化合物除去用の組成物 |
| CA3046068A1 (en) * | 2016-12-08 | 2018-06-14 | Ecolab Usa Inc. | Hydrogen sulfide scavengers for polymer treated asphalt |
| WO2024091459A1 (en) * | 2022-10-24 | 2024-05-02 | Cameron International Corporation | Sulfonyl azide composition for sulfur scavenging in oilfield operations |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0408700B1 (en) * | 1988-12-23 | 1995-08-09 | Petrolite Holdings, Inc. | Method for sweetening hydrocarbons |
| US5128049A (en) * | 1991-01-22 | 1992-07-07 | Gatlin Larry W | Hydrogen sulfide removal process |
| US5354453A (en) * | 1993-04-13 | 1994-10-11 | Exxon Chemical Patents Inc. | Removal of H2 S hydrocarbon liquid |
| US5980733A (en) * | 1994-04-15 | 1999-11-09 | United Laboratories International | Method of removing sulfur compounds from hydrocarbon streams |
| CA2148849A1 (en) * | 1994-06-23 | 1995-12-24 | Kishan Bhatia | Method of treating sour gas and liquid hydrocarbons |
| US5744024A (en) * | 1995-10-12 | 1998-04-28 | Nalco/Exxon Energy Chemicals, L.P. | Method of treating sour gas and liquid hydrocarbon |
| US5922794A (en) * | 1997-03-26 | 1999-07-13 | General Electric Company | Compositions stabilized with tertiary amine oxides |
| EP1065262A1 (en) * | 1999-06-29 | 2001-01-03 | The Procter & Gamble Company | Bleaching compositions |
| KR20050117567A (ko) * | 2003-03-31 | 2005-12-14 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 디젤 연료 조성물 및 디젤 연료의 여과성을 향상시키는방법 |
| US7264786B2 (en) * | 2004-04-21 | 2007-09-04 | Bj Services Company | Method of scavenging hydrogen sulfide and/or mercaptans from fluid and gas streams |
| US9347010B2 (en) * | 2008-04-18 | 2016-05-24 | Schlumberger Norge As | Method of predicting/optimizing hydrogen sulfide scavenging capacity and reduction of scale formation |
| EP2267098A1 (en) * | 2009-06-26 | 2010-12-29 | M-i Swaco Norge As | Scavenger compositons and their use |
-
2010
- 2010-07-14 US US12/835,805 patent/US20120012506A1/en not_active Abandoned
-
2011
- 2011-07-13 AR ARP110102527A patent/AR082847A1/es active IP Right Grant
- 2011-07-13 SG SG2013003025A patent/SG187080A1/en unknown
- 2011-07-13 EP EP11807421.0A patent/EP2593534A4/en not_active Withdrawn
- 2011-07-13 BR BR112013000887A patent/BR112013000887A2/pt not_active Application Discontinuation
- 2011-07-13 JP JP2013519782A patent/JP5815699B2/ja active Active
- 2011-07-13 CN CN2011800347098A patent/CN103003395A/zh active Pending
- 2011-07-13 KR KR1020137003668A patent/KR20130047738A/ko not_active Ceased
- 2011-07-13 CA CA2805402A patent/CA2805402C/en active Active
- 2011-07-13 RU RU2013102415/04A patent/RU2562610C2/ru active
- 2011-07-13 WO PCT/US2011/043780 patent/WO2012009391A2/en not_active Ceased
- 2011-07-13 MX MX2013000511A patent/MX2013000511A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP2593534A4 (en) | 2014-04-23 |
| RU2562610C2 (ru) | 2015-09-10 |
| MX2013000511A (es) | 2013-02-27 |
| US20120012506A1 (en) | 2012-01-19 |
| JP2013532735A (ja) | 2013-08-19 |
| SG187080A1 (en) | 2013-03-28 |
| AR082847A1 (es) | 2013-01-16 |
| EP2593534A2 (en) | 2013-05-22 |
| RU2013102415A (ru) | 2014-08-20 |
| JP5815699B2 (ja) | 2015-11-17 |
| BR112013000887A2 (pt) | 2016-05-17 |
| KR20130047738A (ko) | 2013-05-08 |
| WO2012009391A2 (en) | 2012-01-19 |
| WO2012009391A3 (en) | 2012-05-10 |
| CA2805402A1 (en) | 2012-01-19 |
| CN103003395A (zh) | 2013-03-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2805404C (en) | Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons | |
| CA2805402C (en) | Improved method of removing hydrogen sulfide | |
| CA2818492C (en) | Additive composition and method for scavenging hydrogen sulfide in hydrocarbon streams | |
| AU2010245644B2 (en) | Method of scavenging hydrogen sulfide from hydrocarbon stream | |
| CA2982595C (en) | Method of reducing hydrogen sulfide levels in liquid or gaseous streams using compositions comprising triazines and anionic surfactants | |
| US20120152857A1 (en) | Non-Nitrogen Sulfide Sweeteners | |
| AU2009233811B2 (en) | Quick removal of mercaptans from hydrocarbons | |
| AU2016384296B9 (en) | Hydrogen sulfide scavenging additive composition and method of use thereof | |
| US9273254B2 (en) | Amino acetals and ketals as hydrogen sulfide and mercaptan scavengers | |
| WO2005097300A1 (en) | Removal of mercaptans and related compounds form hydrocarbons | |
| US20140084206A1 (en) | Treating Additives for the Deactivation of Sulfur Species Within a Stream |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160628 |