CA1042141A - Process for the high yield preparation of trans-structure polymers of conjugated diolefins - Google Patents
Process for the high yield preparation of trans-structure polymers of conjugated diolefinsInfo
- Publication number
- CA1042141A CA1042141A CA231,723A CA231723A CA1042141A CA 1042141 A CA1042141 A CA 1042141A CA 231723 A CA231723 A CA 231723A CA 1042141 A CA1042141 A CA 1042141A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- trans
- vanadium
- hydrocarbons
- compounds
- 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 16
- 229920000642 polymer Polymers 0.000 title claims abstract description 15
- 150000001993 dienes Chemical class 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 229910052736 halogen Chemical group 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 150000003682 vanadium compounds Chemical class 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 12
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000005287 vanadyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001399 aluminium compounds Chemical class 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- -1 vanadium halides Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229940077746 antacid containing aluminium compound Drugs 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 abstract description 6
- 229920001519 homopolymer Polymers 0.000 abstract description 3
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002899 organoaluminium compounds Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 9
- 229940045605 vanadium Drugs 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- LVZPKYYPPLUECL-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1 LVZPKYYPPLUECL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000004695 complexes Chemical class 0.000 description 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 1
- PALZAXLZULBBHA-UHFFFAOYSA-N dimethylazanide;vanadium(4+) Chemical compound [V+4].C[N-]C.C[N-]C.C[N-]C.C[N-]C PALZAXLZULBBHA-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25936/74A IT1017870B (it) | 1974-08-02 | 1974-08-02 | Procedimento per la preparazione in alta resa di polimeri a strut tura trans delle diolefine coniu gate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042141A true CA1042141A (en) | 1978-11-07 |
Family
ID=11218189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,723A Expired CA1042141A (en) | 1974-08-02 | 1975-07-17 | Process for the high yield preparation of trans-structure polymers of conjugated diolefins |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5137977A (en, 2012) |
| AU (1) | AU8323775A (en, 2012) |
| BE (1) | BE832059A (en, 2012) |
| CA (1) | CA1042141A (en, 2012) |
| CH (1) | CH606146A5 (en, 2012) |
| CS (1) | CS192550B2 (en, 2012) |
| DD (1) | DD119251A5 (en, 2012) |
| DE (1) | DE2534495A1 (en, 2012) |
| DK (1) | DK351775A (en, 2012) |
| FR (1) | FR2280647A1 (en, 2012) |
| GB (1) | GB1519471A (en, 2012) |
| HU (1) | HU171173B (en, 2012) |
| IL (1) | IL47731A0 (en, 2012) |
| IT (1) | IT1017870B (en, 2012) |
| LU (1) | LU73115A1 (en, 2012) |
| NL (1) | NL7509278A (en, 2012) |
| NO (1) | NO752706L (en, 2012) |
| SE (1) | SE7508743L (en, 2012) |
| SU (1) | SU735171A3 (en, 2012) |
| ZA (1) | ZA754585B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481995A (en) * | 1981-09-14 | 1984-11-13 | Bridgestone Tire Co., Ltd. | Pneumatic radial tires |
-
1974
- 1974-08-02 IT IT25936/74A patent/IT1017870B/it active
-
1975
- 1975-07-16 ZA ZA00754585A patent/ZA754585B/xx unknown
- 1975-07-17 CA CA231,723A patent/CA1042141A/en not_active Expired
- 1975-07-17 GB GB30115/75A patent/GB1519471A/en not_active Expired
- 1975-07-18 IL IL47731A patent/IL47731A0/xx unknown
- 1975-07-21 AU AU83237/75A patent/AU8323775A/en not_active Expired
- 1975-07-29 FR FR7523699A patent/FR2280647A1/fr active Granted
- 1975-07-31 LU LU73115A patent/LU73115A1/xx unknown
- 1975-07-31 DD DD187607A patent/DD119251A5/xx unknown
- 1975-07-31 CH CH1007975A patent/CH606146A5/xx not_active IP Right Cessation
- 1975-07-31 CS CS755359A patent/CS192550B2/cs unknown
- 1975-08-01 HU HU75SA00002823A patent/HU171173B/hu unknown
- 1975-08-01 NO NO752706A patent/NO752706L/no unknown
- 1975-08-01 BE BE158886A patent/BE832059A/xx not_active IP Right Cessation
- 1975-08-01 SE SE7508743A patent/SE7508743L/xx unknown
- 1975-08-01 JP JP50093241A patent/JPS5137977A/ja active Pending
- 1975-08-01 DK DK351775A patent/DK351775A/da unknown
- 1975-08-01 DE DE19752534495 patent/DE2534495A1/de active Pending
- 1975-08-01 SU SU752159096A patent/SU735171A3/ru active
- 1975-08-04 NL NL7509278A patent/NL7509278A/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481995A (en) * | 1981-09-14 | 1984-11-13 | Bridgestone Tire Co., Ltd. | Pneumatic radial tires |
Also Published As
| Publication number | Publication date |
|---|---|
| CS192550B2 (en) | 1979-08-31 |
| GB1519471A (en) | 1978-07-26 |
| LU73115A1 (en, 2012) | 1976-03-02 |
| FR2280647A1 (fr) | 1976-02-27 |
| IT1017870B (it) | 1977-08-10 |
| DK351775A (da) | 1976-02-03 |
| BE832059A (fr) | 1976-02-02 |
| FR2280647B1 (en, 2012) | 1980-07-25 |
| ZA754585B (en) | 1976-07-28 |
| JPS5137977A (en, 2012) | 1976-03-30 |
| IL47731A0 (en) | 1975-11-25 |
| HU171173B (hu) | 1977-11-28 |
| SU735171A3 (ru) | 1980-05-15 |
| SE7508743L (sv) | 1976-02-03 |
| NL7509278A (nl) | 1976-02-04 |
| AU8323775A (en) | 1977-01-27 |
| NO752706L (en, 2012) | 1976-02-03 |
| CH606146A5 (en, 2012) | 1978-10-31 |
| DD119251A5 (en, 2012) | 1976-04-12 |
| DE2534495A1 (de) | 1976-02-12 |
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