DE2853769C3 - Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthält - Google Patents
Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthältInfo
- Publication number
- DE2853769C3 DE2853769C3 DE2853769A DE2853769A DE2853769C3 DE 2853769 C3 DE2853769 C3 DE 2853769C3 DE 2853769 A DE2853769 A DE 2853769A DE 2853769 A DE2853769 A DE 2853769A DE 2853769 C3 DE2853769 C3 DE 2853769C3
- Authority
- DE
- Germany
- Prior art keywords
- methanol
- column
- isobutene
- mtb
- via line
- 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
Links
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 108
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 title claims description 86
- 239000000203 mixture Substances 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 13
- 229930195733 hydrocarbon Natural products 0.000 title claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 234
- -1 C 4 hydrocarbon Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000000047 product Substances 0.000 description 38
- 239000004793 Polystyrene Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- 239000001273 butane Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2853769A DE2853769C3 (de) | 1978-12-13 | 1978-12-13 | Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthält |
| PT70318A PT70318A (fr) | 1978-12-13 | 1979-10-16 | Procede destine a la production simultanee d'ether butilique-methyl-terc. pur (mbt) et une melange de hydrocarbure-c4 largement exempte de isobutene |
| AR279111A AR218791A1 (es) | 1978-12-13 | 1979-11-30 | Procedimiento de preparacion simultanea de eter metil-butilico terciario puro y mezcla de hidrocarburos c4 sustancialmente exenta de isobuteno |
| NO793925A NO149659C (no) | 1978-12-13 | 1979-12-03 | Fremgangsmaate til samtidig fremstilling av ren metyl-tert.-butyleter og vidtgaaende isobutenfri c4-hydrokarbonblanding |
| US06/100,058 US4282389A (en) | 1978-12-13 | 1979-12-04 | Process for the simultaneous manufacture of pure MTBE and a substantially isobutene-free mixture of C4 -hydrocarbons |
| FR7929755A FR2444021A1 (fr) | 1978-12-13 | 1979-12-04 | Procede de preparation simultanee d'ether methyl-tertiobutylique pur et d'un melange d'hydrocarbures en c4 largement exempt d'isobutene |
| YU2970/79A YU39574B (en) | 1978-12-13 | 1979-12-06 | Process of simultaneously producing pure methyl-tert-butylether (mtb) and a mixture of c4-hydrocarbons substantially free of isobutene |
| FI793844A FI69052C (fi) | 1978-12-13 | 1979-12-10 | Foerfarande foer samtidig framstaellning av ren mtb och i stort sett isobutenfri c4-kolvaeteblandning |
| SE7910153A SE445110B (sv) | 1978-12-13 | 1979-12-10 | Forfarande for samtidig framstellning av ren metyl-t-butyleter och en c?714-kolveteblandning med en isobutenhalt under 0,25 vikt-% |
| IT51047/79A IT1164090B (it) | 1978-12-13 | 1979-12-11 | Procedimento ed impianto per produrre etere metil-terz.butilico puro e miscela di idrocarburi c4 ampiamente esente da isobutene |
| PL22032079A PL220320A1 (US06724976-20040420-M00002.png) | 1978-12-13 | 1979-12-11 | |
| CA341,648A CA1128552A (en) | 1978-12-13 | 1979-12-11 | Process for the simultaneous manufacture of pure mtb and a substantially isobutene-free mixture of c.sub.4-hydrocarbons |
| ES486823A ES486823A1 (es) | 1978-12-13 | 1979-12-12 | Procedimiento para la produccion simultanea de mtb puro y una mezcla de hidrocarburos de cuatro atomos de carbono practicamente libre de isobuteno |
| BR7908129A BR7908129A (pt) | 1978-12-13 | 1979-12-12 | Processo para simultanea producao de mtb puro e de mistura de hidrocarbonetos c4 consideravelmente isenta de isobuteno |
| NL7908945A NL7908945A (nl) | 1978-12-13 | 1979-12-12 | Werkwijze voor de gelijktijdige bereiding van zuiver mtb en een nagenoeg isobuteenvrij mengsel van 4 koolstofatomen bevattende koolwaterstoffen. |
| AT0783179A AT370713B (de) | 1978-12-13 | 1979-12-12 | Verfahren zur gleichzeitigen herstellung von reinem methyl-tert.butylaether (mtb) und einem weitgehend isobutenfreiem c4-kohlenwasserstoffgemisch |
| GB7942889A GB2040924B (en) | 1978-12-13 | 1979-12-12 | Process for the simultaneous manufacture of pure methyl t butyl ether and a substantially isobutane-free mixture of c-hydrocarbons |
| RO7999517A RO79319A (ro) | 1978-12-13 | 1979-12-12 | Procedeu de obtinere simultana a eterului metil-tert-butilic si a unui amestec de hidrocarburi c4 |
| IL58936A IL58936A (en) | 1978-12-13 | 1979-12-12 | Simultaneous manufacture of pure methyl tert.-butyl ether and an isobutene-free mixture of c4-hydrocarbons |
| BE0/198539A BE880581A (fr) | 1978-12-13 | 1979-12-12 | Procede de production simultanee d'ether methyl-t-butylique pur et d'un melange d'hydrocarbures en c4 sensiblement exempt d'isobutene |
| DD79217602A DD147664A5 (de) | 1978-12-13 | 1979-12-12 | Verfahren zur gleichzeitigen herstellung von reinem methyl-tert.-butylether |
| SU792853139A SU1367854A3 (ru) | 1978-12-13 | 1979-12-12 | Способ получени метил-трет-бутилового эфира |
| JP16089979A JPS5592326A (en) | 1978-12-13 | 1979-12-13 | Simultaneous manufacture of pure methyllterttbutylether and c44hydrocarbon mixture scarecely containing isobutene |
| HU79HU298A HU182501B (en) | 1978-12-13 | 1979-12-13 | Process for producing pure methyl-terc-butylether and a mixture of hydrocarbons of four caraon atoms containing less than 0,25% isobuthene in simultaneous reaction |
| CS798765A CS236457B2 (en) | 1978-12-13 | 1979-12-13 | Method of pure methyl-tert.buthylether and hydrocarbon mixture simultaneous production with 4 isobutene-free carbon atoms |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2853769A DE2853769C3 (de) | 1978-12-13 | 1978-12-13 | Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthält |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2853769A1 DE2853769A1 (de) | 1980-06-19 |
| DE2853769B2 DE2853769B2 (de) | 1980-10-09 |
| DE2853769C3 true DE2853769C3 (de) | 1989-03-16 |
Family
ID=6057031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2853769A Expired DE2853769C3 (de) | 1978-12-13 | 1978-12-13 | Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthält |
Country Status (25)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629769C3 (de) * | 1976-07-02 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther |
| DE3024147C2 (de) * | 1980-06-27 | 1983-05-05 | Edeleanu Gmbh, 6000 Frankfurt | Verfahren zur Auftrennung der bei der Verätherung von niederen i-Olefinen mit Methanol anfallenden Reaktionsprodukte |
| DE3036481A1 (de) * | 1980-09-27 | 1982-05-19 | EC Erdölchemie GmbH, 5000 Köln | Verfahren zur gemeinsamen herstellung von c 4 -oligomeren und alkyl-tert.-butylethern |
| DE3116780A1 (de) * | 1981-04-28 | 1982-11-04 | Veba Oel AG, 4660 Gelsenkirchen-Buer | Verfahren zur herstellung von sec.-butylalkohol und sec.-butyl-tert.-butylether |
| DE3116779A1 (de) * | 1981-04-28 | 1982-11-04 | Veba Oel AG, 4660 Gelsenkirchen-Buer | Verfahren zur herstellung von alkoholen und aethern |
| US4371718A (en) * | 1981-07-02 | 1983-02-01 | Phillips Petroleum Company | Using butenes to fractionate methanol from methyl-tertiary-butyl ether |
| DE3148109A1 (de) * | 1981-12-04 | 1983-06-09 | EC Erdölchemie GmbH, 5000 Köln | Verfahren zur herstellung von methyl-tert.-butylether (mtbe) und weitgehend von i-buten und vom methanol befreiten kohlenwasserstoff-raffinaten |
| US4413150A (en) * | 1981-12-18 | 1983-11-01 | Uop Inc. | Two product process for methyl tertiary butyl ether production |
| US4510022A (en) * | 1983-08-08 | 1985-04-09 | Lloyd Berg | Separation of isopropyl ether from isopropanol and water by extractive distillation |
| US4558168A (en) * | 1985-06-19 | 1985-12-10 | Air Products And Chemicals, Inc. | Production of high purity butene-1 from an n-butane feedstock |
| US4571439A (en) * | 1985-07-22 | 1986-02-18 | Tenneco Oil Company | Method for controlled oligomerization/etherification of propylene |
| US4761504A (en) * | 1986-12-29 | 1988-08-02 | Uop Inc. | Integrated process for high octane alkylation and etherification |
| US4797133A (en) * | 1986-12-29 | 1989-01-10 | Uop Inc. | Process for recovery of butene-1 from mixed C4 hydrocarbons |
| US4925989A (en) * | 1987-06-01 | 1990-05-15 | Texaco Inc. | MTBE preparation from isobutylene/TBA and methanol in presence of an acid resin catalyst |
| US5210327A (en) * | 1992-05-15 | 1993-05-11 | Uop | Etherification with skeletal olefin isomerization |
| US5276212A (en) * | 1992-12-29 | 1994-01-04 | Uop | Etherification with intermediate skeletal olefin isomerization |
| US5985100A (en) * | 1995-08-30 | 1999-11-16 | Basf Aktiengesellschaft | Process for separating butanol and dibutyl ether by means of dual-pressure distillation |
| US6660898B1 (en) * | 2000-11-03 | 2003-12-09 | Fortum Oil & Gas Oy | Process for dimerizing light olefins to produce a fuel component |
| EP1388528B1 (de) | 2002-08-06 | 2015-04-08 | Evonik Degussa GmbH | Verfahren zur Oligomerisierung von Isobuten in n-Buten-haltigen Kohlenwasserstoffströmen |
| DE102005062699A1 (de) * | 2005-12-28 | 2007-09-06 | Oxeno Olefinchemie Gmbh | Verfahren zur Feinreinigung von 1-Buten-haltigen Strömen |
| JP6350259B2 (ja) * | 2013-12-27 | 2018-07-04 | 東レ株式会社 | 芳香族化合物異性体の製造方法 |
| WO2016046296A1 (en) | 2014-09-26 | 2016-03-31 | Total Research & Technology Feluy | Modified crystalline aluminosilicate for dehydration of alcohols |
| CN105859530B (zh) * | 2015-01-23 | 2018-04-06 | 上海优华系统集成技术有限公司 | 一种稳定塔与mtbe装置催化精馏塔联合循环设备 |
| WO2017005719A1 (en) | 2015-07-09 | 2017-01-12 | Total Research & Technology Feluy | Modified crystalline aluminosilicate for dehydration of alcohols |
| CN109890503B (zh) | 2016-09-09 | 2022-03-29 | 道达尔研究技术弗吕公司 | 使用改性的结晶铝硅酸盐对一元醇脱水的工艺 |
| EP3655384B1 (en) * | 2017-07-19 | 2024-07-10 | SABIC Global Technologies B.V. | Use of mtbe raffinate in the production of propylene |
| CN113058283A (zh) * | 2021-03-01 | 2021-07-02 | 中国石油化工股份有限公司 | Mtbe装置甲醇回收系统及工艺 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1012686B (it) * | 1974-05-21 | 1977-03-10 | Snam Progetti | Procedimento per la preparazione di eteri ter alchilici |
| IT1012690B (it) * | 1974-05-21 | 1977-03-10 | Snam Progetti | Procedimento per la produzione di eteri ter alchilici |
| US3940450A (en) * | 1974-12-16 | 1976-02-24 | Texaco Inc. | Preparation and recovery of ethers |
| FR2312483A1 (fr) * | 1975-05-30 | 1976-12-24 | Erap | Procede de fabrication d'un alkyl tertiobutyl-ether a partir d'une coupe d'hydrocarbures en c4 |
| DE2629769C3 (de) * | 1976-07-02 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther |
| DE2705538A1 (de) * | 1977-02-10 | 1978-08-17 | Basf Ag | Verfahren zur reindarstellung von methyl-tert.-butylaether |
| US4148695A (en) * | 1978-07-27 | 1979-04-10 | Texaco Inc. | Preparation and recovery of ethers |
-
1978
- 1978-12-13 DE DE2853769A patent/DE2853769C3/de not_active Expired
-
1979
- 1979-10-16 PT PT70318A patent/PT70318A/pt unknown
- 1979-11-30 AR AR279111A patent/AR218791A1/es active
- 1979-12-03 NO NO793925A patent/NO149659C/no unknown
- 1979-12-04 US US06/100,058 patent/US4282389A/en not_active Expired - Lifetime
- 1979-12-04 FR FR7929755A patent/FR2444021A1/fr active Granted
- 1979-12-06 YU YU2970/79A patent/YU39574B/xx unknown
- 1979-12-10 SE SE7910153A patent/SE445110B/sv not_active IP Right Cessation
- 1979-12-10 FI FI793844A patent/FI69052C/fi not_active IP Right Cessation
- 1979-12-11 PL PL22032079A patent/PL220320A1/xx unknown
- 1979-12-11 IT IT51047/79A patent/IT1164090B/it active
- 1979-12-11 CA CA341,648A patent/CA1128552A/en not_active Expired
- 1979-12-12 GB GB7942889A patent/GB2040924B/en not_active Expired
- 1979-12-12 SU SU792853139A patent/SU1367854A3/ru active
- 1979-12-12 ES ES486823A patent/ES486823A1/es not_active Expired
- 1979-12-12 IL IL58936A patent/IL58936A/xx not_active IP Right Cessation
- 1979-12-12 BR BR7908129A patent/BR7908129A/pt unknown
- 1979-12-12 AT AT0783179A patent/AT370713B/de not_active IP Right Cessation
- 1979-12-12 DD DD79217602A patent/DD147664A5/de not_active IP Right Cessation
- 1979-12-12 NL NL7908945A patent/NL7908945A/nl not_active Application Discontinuation
- 1979-12-12 RO RO7999517A patent/RO79319A/ro unknown
- 1979-12-12 BE BE0/198539A patent/BE880581A/fr not_active IP Right Cessation
- 1979-12-13 CS CS798765A patent/CS236457B2/cs unknown
- 1979-12-13 HU HU79HU298A patent/HU182501B/hu not_active IP Right Cessation
- 1979-12-13 JP JP16089979A patent/JPS5592326A/ja active Granted
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAM | Search report available | ||
| OAP | Request for examination filed | ||
| OC | Search report available | ||
| OD | Request for examination | ||
| 8263 | Opposition against grant of a patent | ||
| 8227 | New person/name/address of the applicant |
Free format text: HUELS AG, 4370 MARL, DE |
|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |