AU698582B2 - Conversion of methanol to gasoline - Google Patents
Conversion of methanol to gasolineInfo
- Publication number
- AU698582B2 AU698582B2 AU42811/96A AU4281196A AU698582B2 AU 698582 B2 AU698582 B2 AU 698582B2 AU 42811/96 A AU42811/96 A AU 42811/96A AU 4281196 A AU4281196 A AU 4281196A AU 698582 B2 AU698582 B2 AU 698582B2
- Authority
- AU
- Australia
- Prior art keywords
- gas
- temperature
- mtg
- product
- reactor
- 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.)
- Ceased
Links
- 238000006243 chemical reaction Methods 0.000 title claims description 176
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title description 292
- 239000003502 gasoline Substances 0.000 title description 27
- 239000007789 gas Substances 0.000 claims description 486
- 150000002430 hydrocarbons Chemical class 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 88
- 239000003054 catalyst Substances 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 86
- 239000003085 diluting agent Substances 0.000 claims description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 67
- 230000008569 process Effects 0.000 claims description 61
- -1 alkoxy compound Chemical class 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 230000036961 partial effect Effects 0.000 claims description 37
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000047 product Substances 0.000 description 152
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 100
- 229930195733 hydrocarbon Natural products 0.000 description 84
- 239000004215 Carbon black (E152) Substances 0.000 description 78
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 48
- 239000006227 byproduct Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 239000012467 final product Substances 0.000 description 9
- 230000032683 aging Effects 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000003345 natural gas Substances 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000012495 reaction gas Substances 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000013459 approach Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000011027 product recovery Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- WGSMMQXDEYYZTB-UHFFFAOYSA-N 1,2,4,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C=C1C.CC1=CC(C)=C(C)C=C1C WGSMMQXDEYYZTB-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003034 coal gas Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000013627 low molecular weight specie Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Output Control And Ontrol Of Special Type Engine (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/336,430 US5602289A (en) | 1994-11-09 | 1994-11-09 | Conversion of methanol to gasoline |
| US08/336430 | 1994-11-09 | ||
| PCT/US1995/014397 WO1996015082A1 (en) | 1994-11-09 | 1995-11-07 | Conversion of methanol to gasoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4281196A AU4281196A (en) | 1996-06-06 |
| AU698582B2 true AU698582B2 (en) | 1998-11-05 |
Family
ID=23316064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU42811/96A Ceased AU698582B2 (en) | 1994-11-09 | 1995-11-07 | Conversion of methanol to gasoline |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5602289A (OSRAM) |
| EP (1) | EP0790967B1 (OSRAM) |
| JP (1) | JP3732514B2 (OSRAM) |
| AU (1) | AU698582B2 (OSRAM) |
| CA (1) | CA2204775A1 (OSRAM) |
| DE (1) | DE69519999T2 (OSRAM) |
| DK (1) | DK0790967T3 (OSRAM) |
| MY (1) | MY133693A (OSRAM) |
| NO (1) | NO972121L (OSRAM) |
| WO (1) | WO1996015082A1 (OSRAM) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997036845A1 (en) * | 1996-04-01 | 1997-10-09 | Starchem Technologies, Inc. | Fixed bed conversion of methoxy compounds to olefins |
| BR9812534A (pt) * | 1997-09-24 | 2000-07-25 | Christiaan P Van Dijk | Processo de leito fixo para conversão de metanol com catalisador de peneira molecular de fosfato de sìlico alumina |
| US7232936B1 (en) | 2000-02-22 | 2007-06-19 | Exxonmobil Chemical Patents Inc. | Conversion of oxygenate to olefins with staged injection of oxygenate |
| US7205447B2 (en) * | 2002-12-23 | 2007-04-17 | Exxonmobil Chemical Patents Inc. | Process for removing aldehydes and/or ketones from an olefinic stream |
| WO2007108014A1 (en) * | 2006-03-20 | 2007-09-27 | Cri Ehf | Process for producing liquid fuel from carbon dioxide and water |
| CN102617282B (zh) * | 2006-05-30 | 2014-06-25 | 星化学技术公司 | 甲醇的生产方法和体系 |
| US8415518B2 (en) * | 2006-08-03 | 2013-04-09 | Exxonmobil Chemical Patents Inc. | Production of light olefins |
| CA2783154C (en) * | 2006-12-13 | 2014-08-12 | Haldor Topsoee A/S | Process for the synthesis of hydrocarbon constituents of gasoline |
| US20080260631A1 (en) | 2007-04-18 | 2008-10-23 | H2Gen Innovations, Inc. | Hydrogen production process |
| AU2008327945B2 (en) * | 2007-11-19 | 2011-08-11 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefinic product |
| WO2009065848A1 (en) * | 2007-11-19 | 2009-05-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefinic product |
| WO2009129610A1 (en) | 2008-04-21 | 2009-10-29 | Karen Sue Kelly | Production of hydrocarbon liquids |
| US20110054128A1 (en) * | 2009-08-31 | 2011-03-03 | Guang Cao | Controlling Prime Olefin Ratio In An Oxygenates-To-Olefins Reaction |
| DE102009046790B9 (de) | 2009-11-17 | 2013-05-08 | Chemieanlagenbau Chemnitz Gmbh | Verfahren zur Erzeugung von Kohlenwasserstoffen, insbesondere Benzin, aus Synthesegas |
| US9249064B2 (en) | 2009-11-20 | 2016-02-02 | Cri, Ehf | Storage of intermittent renewable energy as fuel using carbon containing feedstock |
| FR2959749B1 (fr) | 2010-05-06 | 2012-06-01 | Inst Francais Du Petrole | Procede flexible de transformation de l'ethanol en distillats moyens. |
| JP5798821B2 (ja) | 2011-07-15 | 2015-10-21 | 三菱重工業株式会社 | メタノールからガソリンを製造するともに発電する方法およびシステム |
| JP5812781B2 (ja) | 2011-09-21 | 2015-11-17 | 三菱重工業株式会社 | メタノールからガソリンと水素を製造する方法および装置 |
| DE102011114367A1 (de) | 2011-09-27 | 2013-03-28 | Lurgi Gmbh | Verfahren und Anlage zur Herstellung von Olefinen aus Dimethylether |
| GB201120398D0 (en) * | 2011-11-25 | 2012-01-11 | Air Fuel Synthesis Ltd | Carbon dioxide convertion process |
| GB201120399D0 (en) | 2011-11-25 | 2012-01-11 | Air Fuel Synthesis Ltd | Convertion of carbon dioxide |
| JP6116801B2 (ja) * | 2012-01-17 | 2017-04-19 | 三菱重工業株式会社 | ガソリンを製造するシステム又は方法 |
| DE102012104128A1 (de) | 2012-05-11 | 2013-11-14 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Verfahren zur Herstellung kurzkettiger Olefine mit verlängerter Zykluszeit |
| DE102013102980A1 (de) | 2013-03-22 | 2014-09-25 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Verfahren zur Herstellung kurzkettiger Olefine aus Oxygenaten |
| WO2022153214A1 (en) | 2021-01-15 | 2022-07-21 | Cri, Ehf | Methanol synthesis reactor |
| US12491484B2 (en) | 2021-01-15 | 2025-12-09 | CRI, hf | Reactor for synthesis of methanol or other products |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4404414A (en) * | 1982-09-28 | 1983-09-13 | Mobil Oil Corporation | Conversion of methanol to gasoline |
| US4547602A (en) * | 1983-11-03 | 1985-10-15 | Mobil Oil Corporation | Reactor sequencing system for converting oxygenates to hydrocarbons |
| US4814536A (en) * | 1987-12-15 | 1989-03-21 | Mobil Oil Corporation | Conversion of oxygenates to gasoline at variable space velocity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3391349A (en) * | 1965-06-18 | 1968-07-02 | Forsvarets Forsknings | Microwave oscillator having a delay line surrounding the interaction chamber |
| US3931349A (en) * | 1974-09-23 | 1976-01-06 | Mobil Oil Corporation | Conversion of methanol to gasoline components |
| US4035430A (en) * | 1976-07-26 | 1977-07-12 | Mobil Oil Corporation | Conversion of methanol to gasoline product |
-
1994
- 1994-11-09 US US08/336,430 patent/US5602289A/en not_active Expired - Fee Related
-
1995
- 1995-11-07 DK DK95941364T patent/DK0790967T3/da active
- 1995-11-07 MY MYPI95003376A patent/MY133693A/en unknown
- 1995-11-07 JP JP51615296A patent/JP3732514B2/ja not_active Expired - Fee Related
- 1995-11-07 DE DE69519999T patent/DE69519999T2/de not_active Expired - Fee Related
- 1995-11-07 CA CA002204775A patent/CA2204775A1/en not_active Abandoned
- 1995-11-07 WO PCT/US1995/014397 patent/WO1996015082A1/en not_active Ceased
- 1995-11-07 AU AU42811/96A patent/AU698582B2/en not_active Ceased
- 1995-11-07 EP EP95941364A patent/EP0790967B1/en not_active Expired - Lifetime
-
1997
- 1997-05-07 NO NO972121A patent/NO972121L/no not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4404414A (en) * | 1982-09-28 | 1983-09-13 | Mobil Oil Corporation | Conversion of methanol to gasoline |
| US4547602A (en) * | 1983-11-03 | 1985-10-15 | Mobil Oil Corporation | Reactor sequencing system for converting oxygenates to hydrocarbons |
| US4814536A (en) * | 1987-12-15 | 1989-03-21 | Mobil Oil Corporation | Conversion of oxygenates to gasoline at variable space velocity |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3732514B2 (ja) | 2006-01-05 |
| MY133693A (en) | 2007-11-30 |
| NO972121D0 (no) | 1997-05-07 |
| WO1996015082A1 (en) | 1996-05-23 |
| EP0790967A4 (OSRAM) | 1997-08-27 |
| US5602289A (en) | 1997-02-11 |
| CA2204775A1 (en) | 1996-05-23 |
| NO972121L (no) | 1997-07-07 |
| DE69519999D1 (de) | 2001-03-01 |
| EP0790967B1 (en) | 2001-01-24 |
| DK0790967T3 (da) | 2001-06-18 |
| AU4281196A (en) | 1996-06-06 |
| DE69519999T2 (de) | 2001-09-06 |
| JPH10506668A (ja) | 1998-06-30 |
| EP0790967A1 (en) | 1997-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |