CA1076745A - Process for making polystyrene - Google Patents
Process for making polystyreneInfo
- Publication number
- CA1076745A CA1076745A CA283,790A CA283790A CA1076745A CA 1076745 A CA1076745 A CA 1076745A CA 283790 A CA283790 A CA 283790A CA 1076745 A CA1076745 A CA 1076745A
- Authority
- CA
- Canada
- Prior art keywords
- styrene monomer
- cation generator
- solution
- temperature
- styrene
- 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
- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000004793 Polystyrene Substances 0.000 title claims abstract description 24
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 21
- 230000008569 process Effects 0.000 title claims description 32
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 77
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- 150000001768 cations Chemical class 0.000 claims abstract description 41
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 62
- 229910015900 BF3 Inorganic materials 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000003085 diluting agent Substances 0.000 claims description 24
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000011347 resin Substances 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011230 binding agent Substances 0.000 abstract description 3
- 239000002243 precursor Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000004014 plasticizer Substances 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 35
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000003426 co-catalyst Substances 0.000 description 9
- 238000010538 cationic polymerization reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 sulfuric Chemical class 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005112 continuous flow technique Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940058172 ethylbenzene Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical class OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71558576A | 1976-08-18 | 1976-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076745A true CA1076745A (en) | 1980-04-29 |
Family
ID=24874665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA283,790A Expired CA1076745A (en) | 1976-08-18 | 1977-07-29 | Process for making polystyrene |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4112209A (OSRAM) |
| JP (1) | JPS5324382A (OSRAM) |
| BE (1) | BE857807A (OSRAM) |
| CA (1) | CA1076745A (OSRAM) |
| DE (1) | DE2736653C2 (OSRAM) |
| FR (1) | FR2362164A1 (OSRAM) |
| GB (1) | GB1545992A (OSRAM) |
| IT (1) | IT1079833B (OSRAM) |
| NL (1) | NL181504C (OSRAM) |
| SE (1) | SE423394B (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594391A (en) * | 1984-05-21 | 1986-06-10 | The Dow Chemical Company | Impact-modified monovinylidene aromatic polymer injection molding resins |
| US4833223A (en) * | 1987-12-14 | 1989-05-23 | Borg-Warner Chemicals, Inc. | High molecular weight polystyrene and method |
| US5288677A (en) * | 1991-06-28 | 1994-02-22 | Exxon Chemical Patents Inc. | Immobilized Lewis acid catalysts |
| US5691431A (en) * | 1996-01-18 | 1997-11-25 | Exxon Chemical Patents Inc. | Cationic polymerization catalyzed by lewis acid catalysts supported on porous polymer substrate |
| US6218573B1 (en) | 1998-07-02 | 2001-04-17 | Rpc Inc. | Methods of recovering catalyst in solution in the oxidation of cyclohexane to adipic acid |
| US6340420B1 (en) | 1998-07-06 | 2002-01-22 | Rpc Inc. | Methods of treating the oxidation mixture of hydrocarbons to respective dibasic acids |
| JP2002542214A (ja) | 1999-04-20 | 2002-12-10 | アールピーシー インコーポレイテッド | 触媒の水溶液中で水およびシクロヘキサノンを酢酸と置換する方法 |
| WO2008008169A2 (en) * | 2006-07-07 | 2008-01-17 | Univation Technologies, Llc | Using electrical probes for detecting impurities in reactor systems |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2499796A (en) * | 1945-01-08 | 1950-03-07 | Chem Dev Corp | Polystyrene resin and polymerization process |
| DE1160618B (de) * | 1962-10-24 | 1964-01-02 | Grace W R & Co | Verfahren zur Herstellung von kristallinem Polystyrol |
| US3385905A (en) * | 1966-02-18 | 1968-05-28 | Dow Chemical Co | Preparation of oligomers of monoalkenyl aromatic monomers |
| US3769359A (en) * | 1972-06-07 | 1973-10-30 | Universal Oil Prod Co | Dimerization of styrene compounds |
| US3763256A (en) * | 1972-06-07 | 1973-10-02 | Universal Oil Prod Co | Dimerization of styrene compounds |
| US3859268A (en) * | 1973-03-09 | 1975-01-07 | Monsanto Co | Continuous mass polymerization of poly alkenyl aromatic polymers |
| DE2402277C2 (de) * | 1974-01-18 | 1982-05-19 | Basf Ag, 6700 Ludwigshafen | Verstärkte thermoplastische Kunststoffe |
-
1977
- 1977-06-30 US US05/811,511 patent/US4112209A/en not_active Expired - Lifetime
- 1977-07-25 US US05/818,686 patent/US4161573A/en not_active Expired - Lifetime
- 1977-07-29 CA CA283,790A patent/CA1076745A/en not_active Expired
- 1977-08-09 NL NLAANVRAGE7708765,A patent/NL181504C/xx not_active IP Right Cessation
- 1977-08-13 DE DE2736653A patent/DE2736653C2/de not_active Expired
- 1977-08-16 BE BE180187A patent/BE857807A/xx not_active IP Right Cessation
- 1977-08-17 IT IT50694/77A patent/IT1079833B/it active
- 1977-08-17 SE SE7709290-6A patent/SE423394B/xx not_active IP Right Cessation
- 1977-08-17 GB GB34595/77A patent/GB1545992A/en not_active Expired
- 1977-08-17 FR FR7725093A patent/FR2362164A1/fr active Granted
- 1977-08-18 JP JP9908677A patent/JPS5324382A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4112209A (en) | 1978-09-05 |
| SE423394B (sv) | 1982-05-03 |
| SE7709290L (sv) | 1978-02-19 |
| NL7708765A (nl) | 1978-02-21 |
| DE2736653A1 (de) | 1978-02-23 |
| JPS5324382A (en) | 1978-03-07 |
| NL181504B (nl) | 1987-04-01 |
| GB1545992A (en) | 1979-05-16 |
| FR2362164B1 (OSRAM) | 1980-02-01 |
| NL181504C (nl) | 1987-09-01 |
| BE857807A (fr) | 1978-02-16 |
| DE2736653C2 (de) | 1984-04-12 |
| JPS6246561B2 (OSRAM) | 1987-10-02 |
| FR2362164A1 (fr) | 1978-03-17 |
| IT1079833B (it) | 1985-05-13 |
| US4161573A (en) | 1979-07-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |