CA1222346A - Continuous preparation of isobutylene polymers - Google Patents
Continuous preparation of isobutylene polymersInfo
- Publication number
- CA1222346A CA1222346A CA000444590A CA444590A CA1222346A CA 1222346 A CA1222346 A CA 1222346A CA 000444590 A CA000444590 A CA 000444590A CA 444590 A CA444590 A CA 444590A CA 1222346 A CA1222346 A CA 1222346A
- Authority
- CA
- Canada
- Prior art keywords
- zone
- solution
- polymerization
- monomers
- isobutylene
- 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 group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 229920000642 polymer Polymers 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 39
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 18
- 239000003999 initiator Substances 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 3
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000243 solution Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 21
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 17
- 238000002156 mixing Methods 0.000 description 13
- 239000001273 butane Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 5
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 4
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 3
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000518994 Conta Species 0.000 description 2
- 229920008712 Copo Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229940037003 alum Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000004821 Contact adhesive Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 241000695274 Processa Species 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- SUAICDWVYXQSNC-UHFFFAOYSA-N butane;2-methylpropane Chemical compound CCCC.CC(C)C SUAICDWVYXQSNC-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- -1 ethyl aluminum dibrom Chemical compound 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000001294 propane 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
- 238000007789 sealing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/08—Butenes
- C08F10/10—Isobutene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833300155 DE3300155A1 (de) | 1983-01-05 | 1983-01-05 | Verfahren zur kontinuierlichen herstellung von isobutylenpolymerisaten |
| DEP3300155.3 | 1983-01-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1222346A true CA1222346A (en) | 1987-05-26 |
Family
ID=6187734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000444590A Expired CA1222346A (en) | 1983-01-05 | 1984-01-03 | Continuous preparation of isobutylene polymers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4558104A (enExample) |
| EP (1) | EP0115635B2 (enExample) |
| JP (1) | JPS59136304A (enExample) |
| AT (1) | ATE18415T1 (enExample) |
| CA (1) | CA1222346A (enExample) |
| DE (2) | DE3300155A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3802176A1 (de) * | 1988-01-26 | 1989-08-03 | Basf Ag | Copolymerisate des isobutylens mit chloracetylierten oder alkylaminoacylierten styrolen, deren herstellung und ihre verwendung zur herstellung von polyurethanen bzw. epoxidharzen oder vernetzten polymerisatmassen |
| US5177288A (en) * | 1988-11-25 | 1993-01-05 | Exxon Chemical Patents Inc. | Polybutene process |
| WO1991014719A2 (en) * | 1990-03-26 | 1991-10-03 | Exxon Chemical Patents Inc. | Improved polybutene process |
| DE4224097A1 (de) | 1992-07-22 | 1994-01-27 | Basf Ag | Die Verwendung von Polyisobutylen für die Entsorgung schadstoffhaltiger Feststoffe und Stäube |
| US5506316A (en) * | 1993-02-19 | 1996-04-09 | Exxon Chemical Patents Inc. | Carbocationic catalysts and process for using said catalysts |
| EP0645402A1 (en) * | 1993-09-24 | 1995-03-29 | Bp Chemicals S.N.C. | Polybutenes |
| DE19525035A1 (de) * | 1995-07-10 | 1997-01-16 | Bayer Ag | Verfahren zur Herstellung von Polyisoolefinen mittels neuer Initiatorsysteme |
| CN1188430C (zh) * | 1999-09-16 | 2005-02-09 | 得克萨斯石油化学产品公司 | 制备聚烯烃的方法 |
| US6992152B2 (en) * | 1999-10-19 | 2006-01-31 | Texas Petrochemicals Lp | Apparatus and method for controlling olefin polymerization process |
| US6858188B2 (en) * | 2003-05-09 | 2005-02-22 | Texas Petrochemicals, Lp | Apparatus for preparing polyolefin products and methodology for using the same |
| EP1937729A1 (de) * | 2005-10-11 | 2008-07-02 | Basf Se | Verfahren zur herstellung von polyisobuten |
| 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 |
| CN102453183B (zh) * | 2010-10-14 | 2013-09-04 | 中国石油天然气股份有限公司 | 一种异烯烃共聚物的制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2491710A (en) * | 1943-06-16 | 1949-12-20 | Standard Oil Dev Co | Nozzle process for making butyl rubber |
| US2405480A (en) * | 1944-10-05 | 1946-08-06 | Standard Oil Dev Co | Polymerization process |
| US2533058A (en) * | 1944-11-23 | 1950-12-05 | Standard Oil Dev Co | Method for polymerizing olefins |
| US2506793A (en) | 1947-01-13 | 1950-05-09 | Fmc Corp | Method of producing fresh whole peeled potato products |
| US2561226A (en) * | 1948-11-18 | 1951-07-17 | Standard Oil Dev Co | Method of polymerizing olefins at subatmospheric temperatures |
| US2772255A (en) | 1952-12-22 | 1956-11-27 | Exxon Research Engineering Co | Polymerization process |
| DE1071340B (de) | 1956-03-08 | 1959-12-17 | Esso Research and Engineering Company Elizabeth N J (V St A) | Verfahren zur Herstellung von Polyisoolefmcn |
| US2906791A (en) * | 1957-03-06 | 1959-09-29 | Exxon Research Engineering Co | Butene dehydrogenation followed by oil and water quenching of the dehydrogenation product effluent |
| US3129205A (en) | 1958-11-03 | 1964-04-14 | Exxon Research Engineering Co | Reactor flushing system |
| BE613811A (enExample) | 1958-12-31 | |||
| US3455890A (en) | 1964-11-18 | 1969-07-15 | Exxon Research Engineering Co | Catalyst for olefin polymerization |
| GB1157043A (en) * | 1966-05-17 | 1969-07-02 | Exxon Research Engineering Co | Low Bulk Viscosity Mastic Compositions |
| GB1157048A (en) * | 1966-07-04 | 1969-07-02 | Vepa Ag | Process and device for the West Treatment of Textile Materials |
| GB1542319A (en) | 1975-11-26 | 1979-03-14 | Exxon Research Engineering Co | Halogenated organoaluminium catalyst compositions and method of their preparation |
| DE2860946D1 (en) | 1977-09-14 | 1981-11-12 | Bp Chem Int Ltd | Process for producing polyisobutenes |
| DE2849280A1 (de) | 1978-11-14 | 1980-05-29 | Bayer Ag | Polymerisate aus viskosen dimethacrylaten in form von perlen |
| DE2936361A1 (de) * | 1979-09-08 | 1981-04-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von polyisobutylenen |
| EP0048627A1 (en) * | 1980-09-24 | 1982-03-31 | BP Chemicals Limited | Catalyst system for cationic (co)polymerisation of 1-olefins |
| US4400493A (en) * | 1982-04-07 | 1983-08-23 | Cosden Technology, Inc. | Polymerization of isobutylene |
-
1983
- 1983-01-05 DE DE19833300155 patent/DE3300155A1/de not_active Withdrawn
- 1983-12-27 EP EP83113135A patent/EP0115635B2/de not_active Expired - Lifetime
- 1983-12-27 DE DE8383113135T patent/DE3362476D1/de not_active Expired
- 1983-12-27 AT AT83113135T patent/ATE18415T1/de not_active IP Right Cessation
- 1983-12-28 US US06/566,292 patent/US4558104A/en not_active Expired - Fee Related
- 1983-12-28 JP JP58245633A patent/JPS59136304A/ja active Granted
-
1984
- 1984-01-03 CA CA000444590A patent/CA1222346A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0115635B1 (de) | 1986-03-05 |
| EP0115635B2 (de) | 1990-08-01 |
| JPH0532409B2 (enExample) | 1993-05-17 |
| US4558104A (en) | 1985-12-10 |
| JPS59136304A (ja) | 1984-08-04 |
| EP0115635A1 (de) | 1984-08-15 |
| ATE18415T1 (de) | 1986-03-15 |
| DE3362476D1 (en) | 1986-04-10 |
| DE3300155A1 (de) | 1984-07-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |