JP2015074785A5 - - Google Patents
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- Publication number
- JP2015074785A5 JP2015074785A5 JP2014208290A JP2014208290A JP2015074785A5 JP 2015074785 A5 JP2015074785 A5 JP 2015074785A5 JP 2014208290 A JP2014208290 A JP 2014208290A JP 2014208290 A JP2014208290 A JP 2014208290A JP 2015074785 A5 JP2015074785 A5 JP 2015074785A5
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- hydrocarbyl
- group
- lewis base
- lewis
- 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.)
- Granted
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 68
- 239000002879 Lewis base Substances 0.000 claims description 63
- 150000007527 lewis bases Chemical class 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 51
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- 239000002904 solvent Substances 0.000 claims description 44
- 239000002841 Lewis acid Substances 0.000 claims description 43
- 150000007517 lewis acids Chemical class 0.000 claims description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- -1 halogen anion Chemical class 0.000 claims description 23
- 239000003999 initiator Substances 0.000 claims description 23
- 150000002576 ketones Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 239000008096 xylene Substances 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000003849 aromatic solvent Substances 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- 150000004292 cyclic ethers Chemical class 0.000 claims description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000011968 lewis acid catalyst Substances 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 150000003568 thioethers Chemical class 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 5
- 229920001083 polybutene Polymers 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 1
- 125000000746 allylic group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000003839 salts Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/052,490 | 2013-10-11 | ||
| US14/052,490 US9631038B2 (en) | 2013-10-11 | 2013-10-11 | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015074785A JP2015074785A (ja) | 2015-04-20 |
| JP2015074785A5 true JP2015074785A5 (enExample) | 2019-01-31 |
| JP6532664B2 JP6532664B2 (ja) | 2019-06-19 |
Family
ID=51687843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014208290A Active JP6532664B2 (ja) | 2013-10-11 | 2014-10-09 | 高反応性オレフィン機能性ポリマーを作製する重合開始系および方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9631038B2 (enExample) |
| EP (1) | EP2860206B1 (enExample) |
| JP (1) | JP6532664B2 (enExample) |
| KR (1) | KR102065510B1 (enExample) |
| CN (1) | CN104558304B (enExample) |
| CA (1) | CA2866525C (enExample) |
| ES (1) | ES2737074T3 (enExample) |
| SG (1) | SG10201405955XA (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9156924B2 (en) * | 2013-03-12 | 2015-10-13 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
| US9771442B2 (en) * | 2015-05-13 | 2017-09-26 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
| SG11201806357PA (en) * | 2016-02-16 | 2018-08-30 | Basf Se | Process for preparing high-reactivity isobutene homo- or copolymers |
| CA3014685C (en) * | 2016-02-16 | 2024-05-28 | Basf Se | Process for preparing high-reactivity isobutene homo- or copolymers |
| SG11201810402PA (en) * | 2016-07-22 | 2018-12-28 | Basf Se | Process for preparing high-reactivity isobutene homo- or copolymers |
| CN106496538B (zh) * | 2016-10-19 | 2021-12-03 | 安徽红太阳新材料有限公司 | 一种高分子量聚己内酯的合成方法 |
| US10167352B1 (en) * | 2017-06-28 | 2019-01-01 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
| US10047174B1 (en) | 2017-06-28 | 2018-08-14 | Infineum International Limited | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
| US10174138B1 (en) * | 2018-01-25 | 2019-01-08 | University Of Massachusetts | Method for forming highly reactive olefin functional polymers |
| KR102301668B1 (ko) | 2018-07-27 | 2021-09-14 | 주식회사 엘지화학 | 폴리부텐 올리고머의 제조 방법 |
| US10829573B1 (en) | 2019-05-21 | 2020-11-10 | Infineum International Limited | Method for forming highly reactive olefin functional polymers |
| CN113661185B (zh) | 2019-08-19 | 2023-12-29 | 株式会社Lg化学 | 有机硼酸盐类催化剂、使用它制备异丁烯低聚物的方法和由此制备的异丁烯低聚物 |
| EP3943518A1 (en) | 2020-07-22 | 2022-01-26 | Indian Oil Corporation Limited | Polymerization catalyst system and process to produce highly reactive polyisobutylene |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2682531A (en) | 1951-03-31 | 1954-06-29 | Standard Oil Dev Co | Zirconium tetrachloride-ether complexes as low temperature polymerization catalyst |
| JPS4839599A (enExample) | 1971-09-20 | 1973-06-11 | ||
| US3850897A (en) | 1971-11-26 | 1974-11-26 | Snam Progetti | Procedure for the production of polymers and copolymers of isobutylene |
| DE2702604C2 (de) | 1977-01-22 | 1984-08-30 | Basf Ag, 6700 Ludwigshafen | Polyisobutene |
| CA2019908A1 (en) | 1989-12-28 | 1991-06-28 | Rudolf Lukas | Graft copolymers and the method and initiation system for preparation thereof |
| GB9025839D0 (en) | 1990-11-28 | 1991-01-09 | Bp Chem Int Ltd | Cationic polymerisation of 1-olefins |
| US5286823A (en) | 1991-06-22 | 1994-02-15 | Basf Aktiengesellschaft | Preparation of highly reactive polyisobutenes |
| US5350819A (en) | 1993-02-19 | 1994-09-27 | Exxon Chemical Patents Inc. | Carbocationic catalysts and process for using said catalysts |
| WO1994028036A1 (en) | 1993-05-20 | 1994-12-08 | Exxon Chemical Patents Inc. | Heterogeneous lewis acid-type catalysts |
| JP3203917B2 (ja) | 1993-11-30 | 2001-09-04 | ソニー株式会社 | プロジェクタ用アクティブマトリクス液晶表示パネル |
| DE69513810T2 (de) | 1994-03-31 | 2000-05-25 | Infineum Usa Lp | Polymerisationsreaktionen von kohlenwasserstoffen mit lewissäure enthaltende trägerkatalysatoren |
| US5710225A (en) | 1996-08-23 | 1998-01-20 | The Lubrizol Corporation | Heteropolyacid catalyzed polymerization of olefins |
| DE19704482A1 (de) | 1997-02-06 | 1998-08-13 | Basf Ag | Verfahren zur Herstellung von halogenfreiem, reaktivem Polyisobuten |
| DE19734176A1 (de) | 1997-08-07 | 1999-02-11 | Basf Ag | Verfahren zur Herstellung von halogenfreiem, reaktivem Polyisobuten |
| US6407186B1 (en) | 1997-12-12 | 2002-06-18 | Basf Aktiengesellschaft | Method for producing low-molecular, highly reactive polyisobutylene |
| CA2330529A1 (en) | 1998-06-12 | 1999-12-16 | Univation Technologies Llc | Olefin polymerization process using activated lewis acid-base complexes |
| US6346585B1 (en) | 1999-06-24 | 2002-02-12 | The Lubrizol Corporation | Ammonium heteropolyacid catalized polymerization of olefins |
| US6407170B1 (en) | 1999-06-24 | 2002-06-18 | The Lubrizol Corporation | Dispersants prepared from high polydispersity olefin polymers |
| JP2001017864A (ja) * | 1999-07-06 | 2001-01-23 | Kawamura Inst Of Chem Res | エポキシ化触媒及び該触媒を用いたオレフィン類のエポキシ化物の製造方法 |
| US6562913B1 (en) | 1999-09-16 | 2003-05-13 | Texas Petrochemicals Lp | Process for producing high vinylidene polyisobutylene |
| DE19952030A1 (de) | 1999-10-28 | 2001-05-03 | Basf Ag | Verfahren zur Herstellung von hochreaktiven Polyisobutenen |
| US6858690B2 (en) | 1999-11-15 | 2005-02-22 | Exxonmobil Chemical Patents Inc. | Process for polymerizing cationically polymerizable monomers |
| JP3735026B2 (ja) * | 2000-02-17 | 2006-01-11 | 住友化学株式会社 | シタロプラムの製造方法、およびその中間体とその製造方法 |
| DE10035298A1 (de) | 2000-07-18 | 2002-01-31 | Basf Ag | Verfahren zur Herstellung von Polysiobutenen |
| WO2002040553A1 (de) | 2000-11-17 | 2002-05-23 | Basf Aktiengesellschaft | Verfahren zur desaktivierung und rückgewinnung von bortrifluorid bei der herstellung von polyisobutenen |
| DE10061715A1 (de) | 2000-12-12 | 2002-06-13 | Basf Ag | Verfahren zur Herstellung von Homo- und Copolymeren des Isobutens |
| DE10118182A1 (de) | 2001-04-11 | 2002-10-17 | Basf Ag | Verfahren zur Aufarbeitung eines flüssigen Reaktionsaustrages der kationischen Polymerisation von Isobuten |
| DE10211418A1 (de) | 2002-03-15 | 2003-09-25 | Bayer Ag | Verfahren zur Herstellung hochreaktiver Polyisobutene |
| AU2003254173A1 (en) | 2002-08-13 | 2004-02-25 | Exxonmobil Chemical Patents Inc. | Process for polymerizing cationically polymerizable monomers |
| AU2003297458A1 (en) | 2002-12-20 | 2004-07-22 | Exxonmobil Chemical Patents Inc. | Polymerization processes |
| CN100402558C (zh) | 2002-12-20 | 2008-07-16 | 埃克森美孚化学专利公司 | 聚合方法 |
| DE10303212A1 (de) | 2003-01-24 | 2004-08-05 | Basf Ag | Verfahren zur Herstellung von Polyisobuten |
| DE10356768A1 (de) | 2003-12-04 | 2005-07-07 | Universität Karlsruhe (TH) - Körperschaft des öffentlichen Rechts | Verfahren zur Herstellung von Salzen schwach koordinierender Anionen, derartige Salze sowie deren Verwendung |
| US20080269440A1 (en) | 2005-01-05 | 2008-10-30 | Rudolf Faust | Polymerization of Olefins |
| DE102005055818A1 (de) | 2005-11-21 | 2007-05-24 | Basf Ag | Verfahren zur Herstellung von hochreaktiven Isobutenhomo- oder -copolymeren mittels metallhaltiger Katalysatorkomplexe |
| WO2008095933A1 (de) | 2007-02-09 | 2008-08-14 | Basf Se | Verfahren zur polymerisation von ethylenisch ungesättigten monomeren |
| US8394897B2 (en) | 2008-03-25 | 2013-03-12 | Chevron Oronite Company Llc | Production of vinylidene-terminated polyolefins via quenching with monosulfides |
| US20090258803A1 (en) | 2008-04-14 | 2009-10-15 | Harrison James J | Copolymers made with quasi-living polyolefins and unsaturated acidic reagents, dispersants using same, and methods of making same |
| US8063154B2 (en) | 2008-06-24 | 2011-11-22 | The University Of Southern Mississippi | Preparation of exo-olefin terminated polyolefins via quenching with alkoxysilanes or ethers |
| CN101613423B (zh) * | 2008-06-27 | 2011-05-18 | 北京化工大学 | 一种用于合成高反应活性聚异丁烯的引发体系 |
| US8530577B2 (en) | 2008-06-30 | 2013-09-10 | Fina Technology, Inc. | Compatibilized polypropylene heterophasic copolymer and polylactic acid blends for injection molding applications |
| WO2010139684A1 (de) | 2009-06-05 | 2010-12-09 | Basf Se | Verbindung aus einem protonierten aromaten und einem schwach koordinierenden anion als polymerisationskatalysator für isobuten oder ein isobuten-haltiges monomerengemisch |
| CN101955558B (zh) | 2009-07-15 | 2013-03-13 | 北京化工大学 | 制备高反应活性聚异丁烯及其共聚物的引发体系 |
| EP2496613B1 (de) | 2009-11-04 | 2015-07-01 | Basf Se | Verfahren zur herstellung von homo- oder copolymeren |
| US8349977B2 (en) | 2010-02-17 | 2013-01-08 | Basf Se | Process for preparing high-reactivity isobutene homo- or copolymers |
| BR112012020302B1 (pt) * | 2010-02-17 | 2021-08-17 | Basf Se | Processo para preparar homo- ou copolímeros de isobuteno de alta reatividade |
| US9562117B2 (en) | 2010-11-30 | 2017-02-07 | Basf Se | Preparation of derivatives of isobutene copolymers |
| BR112014002551A2 (pt) | 2011-08-11 | 2017-03-14 | Basf Se | processo para preparar homo ou copolímeros de isobuteno de alta reatividade, e, polímeros de isobuteno |
| US8697820B2 (en) * | 2011-08-11 | 2014-04-15 | Basf Se | Process for preparing high-reactivity isobutene homo- or copolymers |
| US9034998B2 (en) | 2011-12-16 | 2015-05-19 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
| US9156924B2 (en) * | 2013-03-12 | 2015-10-13 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
| US9771442B2 (en) | 2015-05-13 | 2017-09-26 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
-
2013
- 2013-10-11 US US14/052,490 patent/US9631038B2/en active Active
-
2014
- 2014-09-22 SG SG10201405955XA patent/SG10201405955XA/en unknown
- 2014-10-03 EP EP14187668.0A patent/EP2860206B1/en active Active
- 2014-10-03 ES ES14187668T patent/ES2737074T3/es active Active
- 2014-10-08 CA CA2866525A patent/CA2866525C/en active Active
- 2014-10-09 JP JP2014208290A patent/JP6532664B2/ja active Active
- 2014-10-10 KR KR1020140136958A patent/KR102065510B1/ko active Active
- 2014-10-10 CN CN201410532755.6A patent/CN104558304B/zh active Active
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