DE671419T1 - Herstellung von Polybutenen. - Google Patents
Herstellung von Polybutenen.Info
- Publication number
- DE671419T1 DE671419T1 DE0671419T DE95301302T DE671419T1 DE 671419 T1 DE671419 T1 DE 671419T1 DE 0671419 T DE0671419 T DE 0671419T DE 95301302 T DE95301302 T DE 95301302T DE 671419 T1 DE671419 T1 DE 671419T1
- Authority
- DE
- Germany
- Prior art keywords
- process according
- butene
- range
- catalyst
- feedstock
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 22
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 18
- 239000003054 catalyst Substances 0.000 claims 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 6
- 229930195733 hydrocarbon Natural products 0.000 claims 6
- 150000002430 hydrocarbons Chemical class 0.000 claims 6
- 239000007858 starting material Substances 0.000 claims 6
- 238000006116 polymerization reaction Methods 0.000 claims 5
- 229910015900 BF3 Inorganic materials 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 229920002367 Polyisobutene Polymers 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 3
- 238000010538 cationic polymerization reaction Methods 0.000 claims 3
- 239000002685 polymerization catalyst Substances 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 239000003426 co-catalyst Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- -1 diene compounds Chemical class 0.000 claims 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims 2
- 150000002170 ethers Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 238000005227 gel permeation chromatography Methods 0.000 claims 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000007670 refining Methods 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000001282 iso-butane Substances 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9404368A GB9404368D0 (en) | 1994-03-07 | 1994-03-07 | Production of polyisobutenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE671419T1 true DE671419T1 (de) | 1996-09-19 |
Family
ID=10751418
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69502425T Expired - Lifetime DE69502425T2 (de) | 1994-03-07 | 1995-02-28 | Herstellung von Polybutenen |
| DE0671419T Pending DE671419T1 (de) | 1994-03-07 | 1995-02-28 | Herstellung von Polybutenen. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69502425T Expired - Lifetime DE69502425T2 (de) | 1994-03-07 | 1995-02-28 | Herstellung von Polybutenen |
Country Status (11)
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19619267A1 (de) * | 1996-05-13 | 1997-11-20 | Basf Ag | Verfahren zur Herstellung von mittelmolekularem, hochreaktivem Polyisobuten |
| FR2749015B1 (fr) * | 1996-05-24 | 1998-07-03 | Bp Chemicals Snc | Procede de polymerisation d'olefine(s) |
| DE19646405A1 (de) * | 1996-11-11 | 1998-05-14 | Erdoelchemie Gmbh | Verfahren zur Oligomerisierung von i-Buten |
| FR2757505B1 (fr) * | 1996-12-23 | 1999-02-19 | Inst Francais Du Petrole | Procede de production d'isobutene de haute purete combinant une distillation reactive d'hydroisomerisation, une distillation et une isomerisation squelettale |
| FR2757506B1 (fr) * | 1996-12-23 | 1999-02-19 | Inst Francais Du Petrole | Procede de production d'isobutene de haute purete combinant une distillation reactive d'hydroisomerisation et une isomerisation squelettale |
| US6300444B1 (en) | 1998-08-25 | 2001-10-09 | Nippon Petrochemicals Company, Limited | Process for producing butene polymer |
| JP4489202B2 (ja) * | 1999-02-23 | 2010-06-23 | 新日本石油株式会社 | ブテンポリマーの製造方法 |
| CN1156494C (zh) * | 1999-02-23 | 2004-07-07 | 日本石油化学株式会社 | 丁烯聚合物的制造方法 |
| US6562913B1 (en) | 1999-09-16 | 2003-05-13 | Texas Petrochemicals Lp | Process for producing high vinylidene polyisobutylene |
| EP1242464B1 (en) | 1999-09-16 | 2011-04-27 | TPC Group LLC | Process for preparing polyolefin products |
| US6884858B2 (en) | 1999-10-19 | 2005-04-26 | Texas Petrochemicals Lp | Process for preparing polyolefin products |
| US6992152B2 (en) | 1999-10-19 | 2006-01-31 | Texas Petrochemicals Lp | Apparatus and method for controlling olefin polymerization process |
| US7037999B2 (en) | 2001-03-28 | 2006-05-02 | Texas Petrochemicals Lp | Mid-range vinylidene content polyisobutylene polymer product and process for producing the same |
| US6858188B2 (en) | 2003-05-09 | 2005-02-22 | Texas Petrochemicals, Lp | Apparatus for preparing polyolefin products and methodology for using the same |
| KR100486044B1 (ko) * | 2000-11-13 | 2005-04-29 | 대림산업 주식회사 | 폴리부텐의 제조방법 |
| DE10061715A1 (de) | 2000-12-12 | 2002-06-13 | Basf Ag | Verfahren zur Herstellung von Homo- und Copolymeren des Isobutens |
| DE10061727A1 (de) | 2000-12-12 | 2002-06-13 | Basf Ag | Verfahren zur Herstellung von Polyisobutenen |
| DE10125583A1 (de) | 2001-05-25 | 2002-11-28 | Basf Ag | Verfahren zur Herstellung von Homo- und Copolymeren des Isobutens |
| DE10162567A1 (de) | 2001-12-19 | 2003-07-03 | Basf Ag | Polyisobutene und Polyisobutenderivate für Schmierstoffzusammensetzungen |
| DE10215108A1 (de) * | 2002-04-05 | 2003-10-16 | Basf Ag | Polyisobutenamine |
| US6933351B2 (en) * | 2003-06-20 | 2005-08-23 | Infineum International Limited | Process for forming polyalkenyl acylating agents |
| US7339007B2 (en) * | 2003-06-20 | 2008-03-04 | Infineum International Limited | Low sediment process for thermally reacting highly reactive polymers and enophiles |
| DE502007007119D1 (de) * | 2006-02-23 | 2011-06-16 | Basf Se | Verfahren zur herstellung von polyisobutylen mit einem gehalt an endständigen doppelbindungen von mehr als 50% aus einem technischen 1-buten-, 2-buten |
| US20100234542A1 (en) * | 2006-06-06 | 2010-09-16 | Basf Se | Preparation of reactive, essentially halogen-free polyisobutenes from c4-hydrocarbon mixtures which are low in isobutene |
| CN101600674B (zh) | 2006-11-30 | 2013-09-11 | 巴斯夫欧洲公司 | 烯烃的加氢甲酰化方法 |
| KR100851639B1 (ko) | 2007-03-22 | 2008-08-13 | 대림산업 주식회사 | 고농도 이소부텐을 이용한 고반응성 폴리이소부텐의제조방법 |
| US20100298507A1 (en) | 2009-05-19 | 2010-11-25 | Menschig Klaus R | Polyisobutylene Production Process With Improved Efficiencies And/Or For Forming Products Having Improved Characteristics And Polyisobutylene Products Produced Thereby |
| US8710147B2 (en) | 2009-12-18 | 2014-04-29 | Chevron Oronite Company Llc. | Carbonyl-ene functionalized polyolefins |
| US8673275B2 (en) | 2010-03-02 | 2014-03-18 | Basf Se | Block copolymers and their use |
| CA2789068A1 (en) | 2010-03-02 | 2011-09-06 | Basf Se | Block copolymers and their use |
| JP5343041B2 (ja) * | 2010-06-18 | 2013-11-13 | Ｊｘ日鉱日石エネルギー株式会社 | オレフィン重合体の製造方法 |
| US11072570B2 (en) | 2012-01-09 | 2021-07-27 | Basf Se | Process for continuously preparing polyisobutylene |
| SG10201605034SA (en) | 2012-01-09 | 2016-08-30 | Basf Se | Method for the continuous production of polyisobutylene |
| WO2014070354A1 (en) * | 2012-10-31 | 2014-05-08 | Washington State University | Stable mixed oxide catalysts for direct conversion of ethanol to isobutene and process for making |
| KR101458404B1 (ko) | 2013-01-17 | 2014-11-05 | 대림산업 주식회사 | 폴리부텐의 제조 방법 |
| EP3205674B1 (en) * | 2013-06-05 | 2022-08-03 | DL Chemical CO., LTD | Apparatus and method for preparing polybutene having various molecular weights |
| KR101511701B1 (ko) * | 2013-07-30 | 2015-04-13 | 대림산업 주식회사 | 폴리부텐 제조 시 사용되는 원료의 재순환 장치 및 방법 |
| KR101511708B1 (ko) | 2013-08-28 | 2015-04-13 | 대림산업 주식회사 | 폴리부텐 제조 시 발생되는 할로겐의 제거 장치 및 방법 |
| KR101658545B1 (ko) * | 2014-08-22 | 2016-09-21 | 대림산업 주식회사 | 폴리부텐의 제조방법 |
| US9617366B1 (en) | 2016-03-03 | 2017-04-11 | Tpc Group Llc | Low-fluoride, reactive polyisobutylene |
| WO2017151339A1 (en) | 2016-03-03 | 2017-09-08 | Tpc Group Llc | Low-fluoride, reactive polyisobutylene |
| US9617363B1 (en) | 2016-03-03 | 2017-04-11 | Tpc Group Llc | Low-fluoride, reactive polyisobutylene |
| US12129319B2 (en) | 2018-12-17 | 2024-10-29 | Arlanxeo Singapore Pte. Ltd. | Process for the production of isoolefin polymers using a tertiary ether |
| CA3122590A1 (en) | 2018-12-21 | 2020-06-25 | Arlanxeo Singapore Pte. Ltd. | Continuous process for producing halogenated isoolefin copolymer |
| WO2020132742A1 (en) | 2018-12-27 | 2020-07-02 | ARLANXEO Canada Inc. | Process for producing chlorinated butyl rubber |
| EP3943518A1 (en) | 2020-07-22 | 2022-01-26 | Indian Oil Corporation Limited | Polymerization catalyst system and process to produce highly reactive polyisobutylene |
| US11845705B2 (en) * | 2021-08-17 | 2023-12-19 | Saudi Arabian Oil Company | Processes integrating hydrocarbon cracking with metathesis for producing propene |
| US20230167208A1 (en) * | 2021-11-30 | 2023-06-01 | Braskem S.A. | Heterogeneous catalyst for highly-reactive polyisobutylene |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2775577A (en) * | 1952-12-23 | 1956-12-25 | Exxon Research Engineering Co | Controlled isobutylene polymerization |
| DE2702604C2 (de) * | 1977-01-22 | 1984-08-30 | Basf Ag, 6700 Ludwigshafen | Polyisobutene |
| FR2463802A1 (fr) * | 1979-08-21 | 1981-02-27 | Inst Francais Du Petrole | Procede de valorisation des coupes c4 olefiniques |
| US4358574A (en) * | 1981-01-19 | 1982-11-09 | Exxon Research & Engineering Co. | Production of hydrocarbon resins and products resulting therefrom |
| GB8329082D0 (en) * | 1983-11-01 | 1983-12-07 | Bp Chem Int Ltd | Low molecular weight polymers of 1-olefins |
| US5068490A (en) * | 1989-08-18 | 1991-11-26 | Amoco Corporation | BF3-tertiary etherate complexes for isobutylene polymerization |
| US5254649A (en) * | 1990-11-28 | 1993-10-19 | Bp Chemicals Limited | Cationic polymerization of 1-olefins |
| BE1006694A5 (fr) * | 1991-06-22 | 1994-11-22 | Basf Ag | Procede de preparation de polyisobutenes extremement reactifs. |
| US5416176A (en) * | 1994-06-16 | 1995-05-16 | Phillips Petroleum Company | Method for controlling the feed composition to a process for polymerizing isobutylene |
-
1994
- 1994-03-07 GB GB9404368A patent/GB9404368D0/en active Pending
-
1995
- 1995-02-28 EP EP95301302A patent/EP0671419B1/en not_active Expired - Lifetime
- 1995-02-28 DE DE69502425T patent/DE69502425T2/de not_active Expired - Lifetime
- 1995-02-28 DE DE0671419T patent/DE671419T1/de active Pending
- 1995-03-01 US US08/396,674 patent/US5674955A/en not_active Expired - Lifetime
- 1995-03-02 IN IN351DE1995 patent/IN190180B/en unknown
- 1995-03-06 MY MYPI95000551A patent/MY115946A/en unknown
- 1995-03-07 HU HU9500686A patent/HU218306B/hu unknown
- 1995-03-07 CN CNB951040537A patent/CN1178967C/zh not_active Expired - Lifetime
- 1995-03-07 JP JP04761495A patent/JP3942655B2/ja not_active Expired - Lifetime
- 1995-03-07 BR BR9500835A patent/BR9500835A/pt not_active IP Right Cessation
- 1995-03-07 KR KR1019950004640A patent/KR100362545B1/ko not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP3942655B2 (ja) | 2007-07-11 |
| MY115946A (en) | 2003-10-31 |
| KR100362545B1 (ko) | 2003-02-07 |
| IN190180B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2003-06-28 |
| JPH07268033A (ja) | 1995-10-17 |
| EP0671419B1 (en) | 1998-05-13 |
| HU218306B (en) | 2000-07-28 |
| KR950032300A (ko) | 1995-12-20 |
| CN1178967C (zh) | 2004-12-08 |
| CN1120049A (zh) | 1996-04-10 |
| HU9500686D0 (en) | 1995-04-28 |
| EP0671419A1 (en) | 1995-09-13 |
| HUT71633A (en) | 1996-01-29 |
| DE69502425T2 (de) | 1998-09-03 |
| DE69502425D1 (de) | 1998-06-18 |
| US5674955A (en) | 1997-10-07 |
| GB9404368D0 (en) | 1994-04-20 |
| BR9500835A (pt) | 1995-10-31 |
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