CA2146119C - Process for cracking and transhydrogenation of hydrocarbon feedstock - Google Patents
Process for cracking and transhydrogenation of hydrocarbon feedstock Download PDFInfo
- Publication number
- CA2146119C CA2146119C CA002146119A CA2146119A CA2146119C CA 2146119 C CA2146119 C CA 2146119C CA 002146119 A CA002146119 A CA 002146119A CA 2146119 A CA2146119 A CA 2146119A CA 2146119 C CA2146119 C CA 2146119C
- Authority
- CA
- Canada
- Prior art keywords
- stream
- separated
- hydrocarbons
- transhydrogenation
- hydrogen
- 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
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 36
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 36
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 31
- 238000005336 cracking Methods 0.000 title claims description 26
- 239000012188 paraffin wax Substances 0.000 claims abstract description 12
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 8
- 230000006835 compression Effects 0.000 claims abstract description 6
- 238000007906 compression Methods 0.000 claims abstract description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 50
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 238000000926 separation method Methods 0.000 claims description 28
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 24
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 22
- 239000001294 propane Substances 0.000 claims description 18
- 238000005984 hydrogenation reaction Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 235000013847 iso-butane Nutrition 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 7
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- 239000000370 acceptor Substances 0.000 description 23
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 21
- 239000000852 hydrogen donor Substances 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 235000013844 butane Nutrition 0.000 description 15
- 238000006356 dehydrogenation reaction Methods 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 8
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- -1 palladium Chemical class 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229910021480 group 4 element Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical compound [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 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
- C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
- C10G70/02—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00 by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/50—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor
- C07C5/52—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor with a hydrocarbon as an acceptor, e.g. hydrocarbon disproportionation, i.e. 2CnHp -> CnHp+q + CnHp-q
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929222416A GB9222416D0 (en) | 1992-10-26 | 1992-10-26 | Hydrocarbons |
| GB9222416.1 | 1992-10-26 | ||
| PCT/GB1993/002136 WO1994010264A1 (en) | 1992-10-26 | 1993-10-15 | Process for cracking and transhydrogenation of hydrocarbon feedstock |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2146119A1 CA2146119A1 (en) | 1994-05-11 |
| CA2146119C true CA2146119C (en) | 2005-01-11 |
Family
ID=10724036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002146119A Expired - Fee Related CA2146119C (en) | 1992-10-26 | 1993-10-15 | Process for cracking and transhydrogenation of hydrocarbon feedstock |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5837127A (en, 2012) |
| EP (1) | EP0665871B1 (en, 2012) |
| JP (1) | JP3452318B2 (en, 2012) |
| KR (1) | KR100275346B1 (en, 2012) |
| AU (1) | AU5284093A (en, 2012) |
| CA (1) | CA2146119C (en, 2012) |
| DE (1) | DE69307336T2 (en, 2012) |
| DK (1) | DK0665871T3 (en, 2012) |
| ES (1) | ES2099483T3 (en, 2012) |
| GB (1) | GB9222416D0 (en, 2012) |
| IN (1) | IN187932B (en, 2012) |
| WO (1) | WO1994010264A1 (en, 2012) |
| ZA (1) | ZA937790B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69312481T2 (de) * | 1992-04-14 | 1998-02-05 | Inst Francais Du Petrol | Verfahren zur herstellung von olefinen |
| EP1365005B1 (en) | 1995-11-28 | 2005-10-19 | Shell Internationale Researchmaatschappij B.V. | Process for producing lubricating base oils |
| US6203694B1 (en) * | 1998-05-13 | 2001-03-20 | Phillips Petroleum Company | Conversion of heavy hydrocarbon to aromatics and light olefins |
| CN100378203C (zh) | 2003-06-23 | 2008-04-02 | 国际壳牌研究有限公司 | 制备润滑基础油的方法 |
| EP1812533B1 (en) | 2004-11-18 | 2011-02-16 | Shell Internationale Research Maatschappij B.V. | Process to prepare a gas oil |
| BRPI0517785A (pt) | 2004-11-18 | 2008-10-21 | Shell Int Research | processo para otimizar o rendimento de óleos de base a partir de uma alimentação derivada de fischer-tropsch |
| WO2006122585A1 (en) | 2005-05-19 | 2006-11-23 | Shell Internationale Research Maatschappij B.V. | Quenching fluid |
| WO2006136594A1 (en) | 2005-06-23 | 2006-12-28 | Shell Internationale Research Maatschappij B.V. | Electrical oil formulation |
| EP1899443A1 (en) | 2005-07-01 | 2008-03-19 | Shell Internationale Research Maatschappij B.V. | Process to prepare a blended brightstock |
| BRPI0820104A2 (pt) | 2007-12-07 | 2015-05-05 | Shell Int Research | Formulação de óleo de base, óleo elétrico ou fluído hidráulico, método para preparar uma formulação de óleo de base, uso de um gasóleo derivado de fischer-tropsch, e, método para melhorar as propriedades de fluxo a frio e/ou redução da viscosidade cinemática de uma formulação de óleo de base |
| EP2075314A1 (en) | 2007-12-11 | 2009-07-01 | Shell Internationale Research Maatschappij B.V. | Grease formulations |
| EP2100946A1 (en) | 2008-09-08 | 2009-09-16 | Shell Internationale Researchmaatschappij B.V. | Oil formulations |
| US9587183B2 (en) | 2011-12-16 | 2017-03-07 | Shell Oil Company | Integrated gas-to-liquid condensate process and apparatus |
| US20150322351A1 (en) | 2012-12-17 | 2015-11-12 | Shell Oil Company | Integrated gas-to-liquid condensate process |
| WO2014095815A1 (en) | 2012-12-17 | 2014-06-26 | Shell Internationale Research Maatschappij B.V. | Integrated gas-to-liquid condensate process |
| EP3169753B1 (en) | 2014-07-17 | 2020-06-10 | SABIC Global Technologies B.V. | Upgrading hydrogen deficient streams using hydrogen donor streams in a hydropyrolysis process |
| CN111943799A (zh) * | 2020-09-07 | 2020-11-17 | 天津市创举科技股份有限公司 | 一种以含烯烃的原料生产异辛烯的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2322025A (en) * | 1939-04-03 | 1943-06-15 | Universal Oil Prod Co | Conversion of hydrocarbons |
| US3211635A (en) * | 1961-04-14 | 1965-10-12 | Phillips Petroleum Co | Production of olefins from paraffins and acetylenes |
| US3267170A (en) * | 1964-06-30 | 1966-08-16 | Exxon Research Engineering Co | Process for forming olefins by hydrogen transfer |
| US3321545A (en) * | 1964-06-30 | 1967-05-23 | Exxon Research Engineering Co | Olefins by hydrogen transfer |
| US3267171A (en) * | 1965-02-18 | 1966-08-16 | Exxon Research Engineering Co | Process for forming olefins by hydrogen transfer |
| DE1925439C3 (de) * | 1969-05-19 | 1978-11-02 | Institut Neftechimitscheskogo Sinteza Imeni A.V. Toptschieva Akademii Nauk Ssr, Moskau | Verfahren zur Durchführung von Prozessen in einem Reaktionsgefäß mit katalytisch aktiver, semipermeabler Trennwand |
| US3855327A (en) * | 1971-07-08 | 1974-12-17 | Phillips Petroleum Co | Hydrogenation of unsaturated compounds |
| IT1028290B (it) * | 1975-01-10 | 1979-01-30 | Snam Progetti | Procedimento per la preparazione di complessi di metalli dell viii gruppo del sistema periodico e loro impiego quali catalizzatori di trasferimento di idrogeno in fage eterogenea |
| US4546204A (en) * | 1983-11-07 | 1985-10-08 | Imperial Chemical Industries Australia Limited | Process for the manufacture of methyl t-butyl ether |
| US4684755A (en) * | 1985-09-27 | 1987-08-04 | Ici Australia Limited | Catalyzed process |
| US4975097A (en) * | 1987-12-08 | 1990-12-04 | Mobil Oil Corporation | Iso-olefin etherification, upgrading and paraffin transhydrogenation |
| US5047070A (en) * | 1988-04-11 | 1991-09-10 | Mobil Oil Corporation | Integrated process for production of gasoline and ether from alcohol with feedstock extraction |
| US5160424A (en) * | 1989-11-29 | 1992-11-03 | Mobil Oil Corporation | Hydrocarbon cracking, dehydrogenation and etherification process |
| GB9208154D0 (en) * | 1991-05-03 | 1992-05-27 | Ici Plc | Transhydrogenation |
| DE69312481T2 (de) * | 1992-04-14 | 1998-02-05 | Inst Francais Du Petrol | Verfahren zur herstellung von olefinen |
-
1992
- 1992-10-26 GB GB929222416A patent/GB9222416D0/en active Pending
-
1993
- 1993-10-15 DK DK93923005.8T patent/DK0665871T3/da active
- 1993-10-15 ES ES93923005T patent/ES2099483T3/es not_active Expired - Lifetime
- 1993-10-15 CA CA002146119A patent/CA2146119C/en not_active Expired - Fee Related
- 1993-10-15 EP EP93923005A patent/EP0665871B1/en not_active Expired - Lifetime
- 1993-10-15 KR KR1019950701607A patent/KR100275346B1/ko not_active Expired - Fee Related
- 1993-10-15 AU AU52840/93A patent/AU5284093A/en not_active Abandoned
- 1993-10-15 US US08/407,019 patent/US5837127A/en not_active Expired - Fee Related
- 1993-10-15 WO PCT/GB1993/002136 patent/WO1994010264A1/en active IP Right Grant
- 1993-10-15 JP JP51042394A patent/JP3452318B2/ja not_active Expired - Fee Related
- 1993-10-15 DE DE69307336T patent/DE69307336T2/de not_active Expired - Fee Related
- 1993-10-19 IN IN1177DE1993 patent/IN187932B/en unknown
- 1993-10-20 ZA ZA937790A patent/ZA937790B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR950704448A (ko) | 1995-11-20 |
| GB9222416D0 (en) | 1992-12-09 |
| JP3452318B2 (ja) | 2003-09-29 |
| WO1994010264A1 (en) | 1994-05-11 |
| AU5284093A (en) | 1994-05-24 |
| CA2146119A1 (en) | 1994-05-11 |
| DE69307336T2 (de) | 1997-04-24 |
| DK0665871T3 (da) | 1997-06-30 |
| IN187932B (en, 2012) | 2002-07-27 |
| EP0665871B1 (en) | 1997-01-08 |
| EP0665871A1 (en) | 1995-08-09 |
| JPH08502535A (ja) | 1996-03-19 |
| ES2099483T3 (es) | 1997-05-16 |
| KR100275346B1 (ko) | 2000-12-15 |
| US5837127A (en) | 1998-11-17 |
| DE69307336D1 (de) | 1997-02-20 |
| ZA937790B (en) | 1994-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |