DE2257485A1 - Verfahren zur herstellung von polymeren und copolymeren von isobutylen und die dabei erhaltenen produkte - Google Patents
Verfahren zur herstellung von polymeren und copolymeren von isobutylen und die dabei erhaltenen produkteInfo
- Publication number
- DE2257485A1 DE2257485A1 DE2257485A DE2257485A DE2257485A1 DE 2257485 A1 DE2257485 A1 DE 2257485A1 DE 2257485 A DE2257485 A DE 2257485A DE 2257485 A DE2257485 A DE 2257485A DE 2257485 A1 DE2257485 A1 DE 2257485A1
- Authority
- DE
- Germany
- Prior art keywords
- isobutylene
- isoprene
- reaction
- polymers
- copolymers
- 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
- 229920000642 polymer Polymers 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 21
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 15
- 229920001577 copolymer Polymers 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims 1
- 229920005549 butyl rubber Polymers 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- -1 carbonium ions Chemical class 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 229960003750 ethyl chloride Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CSNJTIWCTNEOSW-UHFFFAOYSA-N carbamothioylsulfanyl carbamodithioate Chemical compound NC(=S)SSC(N)=S CSNJTIWCTNEOSW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 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
- C08F10/14—Monomers containing five or more carbon atoms
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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT31728/71A IT946104B (it) | 1971-11-26 | 1971-11-26 | Procedimeno per la produzione di polimeri e copolimeri dell isobu tene e prodotti ottenuti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2257485A1 true DE2257485A1 (de) | 1973-06-07 |
Family
ID=11234278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257485A Pending DE2257485A1 (de) | 1971-11-26 | 1972-11-23 | Verfahren zur herstellung von polymeren und copolymeren von isobutylen und die dabei erhaltenen produkte |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5243238B2 (cs) |
| AT (1) | AT319591B (cs) |
| AU (1) | AU472858B2 (cs) |
| BE (1) | BE791779A (cs) |
| CA (1) | CA998496A (cs) |
| CH (1) | CH553229A (cs) |
| CS (1) | CS179976B2 (cs) |
| DD (1) | DD104799A5 (cs) |
| DE (1) | DE2257485A1 (cs) |
| ES (1) | ES409265A1 (cs) |
| FR (1) | FR2160888B1 (cs) |
| GB (1) | GB1407420A (cs) |
| HU (1) | HU167166B (cs) |
| IN (1) | IN138882B (cs) |
| IT (1) | IT946104B (cs) |
| LU (1) | LU66531A1 (cs) |
| NL (1) | NL153890B (cs) |
| PL (1) | PL94405B1 (cs) |
| RO (1) | RO62848A (cs) |
| SU (1) | SU493975A3 (cs) |
| ZA (2) | ZA727774B (cs) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3066123A (en) * | 1958-09-10 | 1962-11-27 | Exxon Research Engineering Co | Activated friedel-crafts catalysts for polymerization |
| FR1413467A (fr) * | 1963-11-01 | 1965-10-08 | Exxon Research Engineering Co | Procédé de préparation d'un catalyseur |
-
0
- BE BE791779D patent/BE791779A/xx unknown
-
1971
- 1971-11-26 IT IT31728/71A patent/IT946104B/it active
-
1972
- 1972-10-19 AU AU47933/72A patent/AU472858B2/en not_active Expired
- 1972-11-01 ZA ZA727774A patent/ZA727774B/xx unknown
- 1972-11-01 ZA ZA727772A patent/ZA727772B/xx unknown
- 1972-11-16 CS CS7200007785A patent/CS179976B2/cs unknown
- 1972-11-21 FR FR7241222A patent/FR2160888B1/fr not_active Expired
- 1972-11-23 DE DE2257485A patent/DE2257485A1/de active Pending
- 1972-11-24 RO RO7200072928A patent/RO62848A/ro unknown
- 1972-11-24 SU SU1852397A patent/SU493975A3/ru active
- 1972-11-24 GB GB5452972A patent/GB1407420A/en not_active Expired
- 1972-11-24 DD DD167141A patent/DD104799A5/xx unknown
- 1972-11-24 HU HUSA2429A patent/HU167166B/hu unknown
- 1972-11-24 LU LU66531A patent/LU66531A1/xx unknown
- 1972-11-24 CA CA157,502A patent/CA998496A/en not_active Expired
- 1972-11-24 AT AT1005972A patent/AT319591B/de not_active IP Right Cessation
- 1972-11-24 PL PL1972159062A patent/PL94405B1/pl unknown
- 1972-11-25 ES ES409265A patent/ES409265A1/es not_active Expired
- 1972-11-25 CH CH1719472A patent/CH553229A/fr not_active IP Right Cessation
- 1972-11-27 JP JP47118134A patent/JPS5243238B2/ja not_active Expired
- 1972-11-27 NL NL727216040A patent/NL153890B/xx unknown
- 1972-11-29 IN IN2026/72A patent/IN138882B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA727772B (en) | 1973-08-29 |
| LU66531A1 (cs) | 1973-02-01 |
| HU167166B (cs) | 1975-08-28 |
| IN138882B (cs) | 1976-04-10 |
| GB1407420A (en) | 1975-09-24 |
| JPS5243238B2 (cs) | 1977-10-28 |
| CA998496A (en) | 1976-10-12 |
| ZA727774B (en) | 1973-08-29 |
| FR2160888B1 (cs) | 1975-03-28 |
| SU493975A3 (ru) | 1975-11-28 |
| RO62848A (fr) | 1977-11-15 |
| AU472858B2 (en) | 1976-06-10 |
| ES409265A1 (es) | 1976-03-01 |
| AT319591B (de) | 1974-12-27 |
| FR2160888A1 (cs) | 1973-07-06 |
| CH553229A (fr) | 1974-08-30 |
| AU4793372A (en) | 1974-04-26 |
| JPS4864176A (cs) | 1973-09-05 |
| DD104799A5 (cs) | 1974-03-20 |
| CS179976B2 (en) | 1977-12-30 |
| BE791779A (fr) | 1973-03-16 |
| NL7216040A (cs) | 1973-05-29 |
| PL94405B1 (pl) | 1977-08-31 |
| NL153890B (nl) | 1977-07-15 |
| IT946104B (it) | 1973-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OHW | Rejection |