CA2000573C - Removing hydrogen sulphide from a gas mixture - Google Patents
Removing hydrogen sulphide from a gas mixture Download PDFInfo
- Publication number
- CA2000573C CA2000573C CA002000573A CA2000573A CA2000573C CA 2000573 C CA2000573 C CA 2000573C CA 002000573 A CA002000573 A CA 002000573A CA 2000573 A CA2000573 A CA 2000573A CA 2000573 C CA2000573 C CA 2000573C
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- aminopyridine
- alkyl
- gas mixture
- independently selected
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 239000007789 gas Substances 0.000 title claims abstract description 24
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 20
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000002250 absorbent Substances 0.000 claims abstract description 24
- 230000002745 absorbent Effects 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000003927 aminopyridines Chemical class 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 12
- 239000001569 carbon dioxide Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- YTQVUCXSUXFTFM-UHFFFAOYSA-N n,n,2-trimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC(C)=C1 YTQVUCXSUXFTFM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- ISDZORVSNLUMDN-UHFFFAOYSA-N n,n,2,6-tetramethylpyridin-4-amine Chemical compound CN(C)C1=CC(C)=NC(C)=C1 ISDZORVSNLUMDN-UHFFFAOYSA-N 0.000 claims 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 12
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 8
- CBIDRCWHNCKSTO-UHFFFAOYSA-N prenyl diphosphate Chemical compound CC(C)=CCO[P@](O)(=O)OP(O)(O)=O CBIDRCWHNCKSTO-UHFFFAOYSA-N 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-methoxytryptamine Chemical compound COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 description 1
- 208000007542 Paresis Diseases 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 208000012318 pareses Diseases 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- -1 pyridine compound Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- GCTNBVHDRFKLLK-UHFFFAOYSA-N thujane Natural products CC1CCC2(C(C)C)C1C2 GCTNBVHDRFKLLK-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Gas Separation By Absorption (AREA)
- Treating Waste Gases (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Filtering Of Dispersed Particles In Gases (AREA)
- Industrial Gases (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888824943A GB8824943D0 (en) | 1988-10-25 | 1988-10-25 | Removing hydrogen sulphide from gas mixture |
| GB8824943 | 1988-10-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2000573A1 CA2000573A1 (en) | 1990-04-25 |
| CA2000573C true CA2000573C (en) | 2000-08-08 |
Family
ID=10645740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002000573A Expired - Fee Related CA2000573C (en) | 1988-10-25 | 1989-10-12 | Removing hydrogen sulphide from a gas mixture |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4959086A (enEXAMPLES) |
| EP (1) | EP0366206B1 (enEXAMPLES) |
| JP (1) | JP2932191B2 (enEXAMPLES) |
| KR (1) | KR0139634B1 (enEXAMPLES) |
| AT (1) | ATE84437T1 (enEXAMPLES) |
| AU (1) | AU620161B2 (enEXAMPLES) |
| BR (1) | BR8905377A (enEXAMPLES) |
| CA (1) | CA2000573C (enEXAMPLES) |
| DE (1) | DE68904398T2 (enEXAMPLES) |
| ES (1) | ES2044067T3 (enEXAMPLES) |
| GB (1) | GB8824943D0 (enEXAMPLES) |
| GR (1) | GR3006789T3 (enEXAMPLES) |
| IN (1) | IN173688B (enEXAMPLES) |
| MY (1) | MY105609A (enEXAMPLES) |
| NO (1) | NO175409C (enEXAMPLES) |
| ZA (1) | ZA898001B (enEXAMPLES) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19947845A1 (de) * | 1999-10-05 | 2001-04-12 | Basf Ag | Verfahren zum Entfernen von COS aus einem Kohlenwasserstoff-Fluidstrom und Waschflüssikgkeit zur Verwendung in derartigen Verfahren |
| US8152903B2 (en) * | 2005-08-09 | 2012-04-10 | Exxonmobile Research & Engineering Company | Hindered cyclic polyamines and their salts for acid gas scrubbing process |
| WO2011121633A1 (ja) * | 2010-03-29 | 2011-10-06 | 株式会社 東芝 | 酸性ガス吸収剤、酸性ガス除去装置および酸性ガス除去方法 |
| US8652237B2 (en) * | 2010-12-17 | 2014-02-18 | Battelle Memorial Institute | System and process for capture of H2S from gaseous process streams and process for regeneration of the capture agent |
| JP5659084B2 (ja) * | 2011-05-30 | 2015-01-28 | 株式会社東芝 | 酸性ガス吸収剤、酸性ガス除去方法および酸性ガス除去装置 |
| BR112014002107A2 (pt) * | 2011-07-28 | 2017-02-21 | Dow Global Technologies Llc | composto 1-hidroxietil-4-piridinil-piperazina e processo para remover sulfeto de hidrogênio de uma corrente fluida incluindo sulfeto de hidrogênio |
| CA2876683A1 (en) | 2012-06-15 | 2013-12-19 | Dow Global Technologies Llc | Process for the treatment of liquefied hydrocarbons using 3-(piperazine-1-yl)propane-1,2-diol compounds |
| RU2636517C2 (ru) | 2012-06-15 | 2017-11-23 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Способ обработки сжиженных углеводородов с использованием 3-(амино)пропан-1,2-диольных соединений |
| WO2013188367A1 (en) | 2012-06-15 | 2013-12-19 | Dow Global Technologies Llc | Process for the treatment of liquefied hydrocarbon gas using 2 -amino -2 (hydroxymethyl) propane - 1, 3 - diol compounds |
| US10130907B2 (en) | 2016-01-20 | 2018-11-20 | Battelle Memorial Institute | Capture and release of acid gasses using tunable organic solvents with aminopyridine |
| CN109069987A (zh) | 2016-04-29 | 2018-12-21 | 陶氏环球技术有限责任公司 | 使用甘醇、咪唑化合物和任选的添加剂使气体脱水的组合物和方法 |
| US10456739B2 (en) | 2016-11-14 | 2019-10-29 | Battelle Memorial Institute | Capture and release of acid gasses using tunable organic solvents with binding organic liquids |
| IT202000028301A1 (it) * | 2020-11-25 | 2022-05-25 | Eni Spa | Rimozione di gas acidi da miscele gassose che li contengono. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4353840A (en) * | 1980-07-23 | 1982-10-12 | Tenneco Chemicals, Inc. | Use of amine-aluminum chloride adducts as alkylation inhibitors in a ligand-complexing process |
| US4541946A (en) * | 1981-03-12 | 1985-09-17 | Standard Oil Company | Corrosion inhibitor for amine gas sweetening systems |
| US4360363A (en) * | 1982-02-16 | 1982-11-23 | Combustion Engineering, Inc. | Physical solvent for gas sweetening |
| US4748011A (en) * | 1983-07-13 | 1988-05-31 | Baize Thomas H | Method and apparatus for sweetening natural gas |
| JP4915556B2 (ja) | 2006-05-26 | 2012-04-11 | パナソニック株式会社 | バランス訓練装置 |
-
1988
- 1988-10-25 GB GB888824943A patent/GB8824943D0/en active Pending
-
1989
- 1989-10-12 CA CA002000573A patent/CA2000573C/en not_active Expired - Fee Related
- 1989-10-20 US US07/424,649 patent/US4959086A/en not_active Expired - Lifetime
- 1989-10-23 ZA ZA898001A patent/ZA898001B/xx unknown
- 1989-10-23 IN IN776MA1989 patent/IN173688B/en unknown
- 1989-10-23 BR BR898905377A patent/BR8905377A/pt not_active IP Right Cessation
- 1989-10-23 AU AU43644/89A patent/AU620161B2/en not_active Ceased
- 1989-10-23 JP JP1273906A patent/JP2932191B2/ja not_active Expired - Fee Related
- 1989-10-23 NO NO894202A patent/NO175409C/no unknown
- 1989-10-23 KR KR1019890015215A patent/KR0139634B1/ko not_active Expired - Fee Related
- 1989-10-23 MY MYPI89001467A patent/MY105609A/en unknown
- 1989-10-24 DE DE8989202690T patent/DE68904398T2/de not_active Expired - Fee Related
- 1989-10-24 ES ES89202690T patent/ES2044067T3/es not_active Expired - Lifetime
- 1989-10-24 EP EP89202690A patent/EP0366206B1/en not_active Expired - Lifetime
- 1989-10-24 AT AT89202690T patent/ATE84437T1/de not_active IP Right Cessation
-
1993
- 1993-01-14 GR GR930400011T patent/GR3006789T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO175409B (no) | 1994-07-04 |
| KR900006014A (ko) | 1990-05-07 |
| BR8905377A (pt) | 1990-05-22 |
| KR0139634B1 (ko) | 1998-06-01 |
| AU4364489A (en) | 1990-05-03 |
| ATE84437T1 (de) | 1993-01-15 |
| AU620161B2 (en) | 1992-02-13 |
| GR3006789T3 (enEXAMPLES) | 1993-06-30 |
| JP2932191B2 (ja) | 1999-08-09 |
| GB8824943D0 (en) | 1988-11-30 |
| CA2000573A1 (en) | 1990-04-25 |
| EP0366206A3 (en) | 1991-04-03 |
| NO894202L (no) | 1990-04-26 |
| MY105609A (en) | 1994-11-30 |
| EP0366206A2 (en) | 1990-05-02 |
| JPH02172517A (ja) | 1990-07-04 |
| NO894202D0 (no) | 1989-10-23 |
| US4959086A (en) | 1990-09-25 |
| ZA898001B (en) | 1990-07-25 |
| DE68904398D1 (de) | 1993-02-25 |
| NO175409C (no) | 1994-10-12 |
| ES2044067T3 (es) | 1994-01-01 |
| EP0366206B1 (en) | 1993-01-13 |
| IN173688B (enEXAMPLES) | 1994-06-25 |
| DE68904398T2 (de) | 1993-05-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDC | Discontinued application reinstated | ||
| MKLA | Lapsed |