CN1068575C - 碳桥式双环戊二烯化合物的合成工艺 - Google Patents
碳桥式双环戊二烯化合物的合成工艺 Download PDFInfo
- Publication number
- CN1068575C CN1068575C CN96110141A CN96110141A CN1068575C CN 1068575 C CN1068575 C CN 1068575C CN 96110141 A CN96110141 A CN 96110141A CN 96110141 A CN96110141 A CN 96110141A CN 1068575 C CN1068575 C CN 1068575C
- Authority
- CN
- China
- Prior art keywords
- compound
- carbon
- methyl
- cyclopentadienyl
- indenyl
- 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 - Lifetime
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- -1 dicyclic pentylene compound Chemical class 0.000 title claims abstract description 95
- 238000000034 method Methods 0.000 title claims description 15
- 230000008569 process Effects 0.000 title claims description 9
- 230000002194 synthesizing effect Effects 0.000 title 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000003513 alkali Substances 0.000 claims abstract description 12
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 10
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 22
- 238000005516 engineering process Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000010953 base metal Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 239000002633 crown compound Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910000765 intermetallic Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000001412 amines Chemical group 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 16
- 150000002469 indenes Chemical class 0.000 description 15
- 235000010290 biphenyl Nutrition 0.000 description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000001294 propane Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 7
- 150000002220 fluorenes Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 4
- CAYKGPJSXROKPC-UHFFFAOYSA-N 1-(2-methyl-1h-inden-4-yl)naphthalene Chemical class C1=CC=C2C(C3=CC=CC4=C3C=C(C4)C)=CC=CC2=C1 CAYKGPJSXROKPC-UHFFFAOYSA-N 0.000 description 4
- KXYGKDBONOVZOM-UHFFFAOYSA-N 1h-cyclopenta[a]naphthalene Chemical compound C1=CC=CC2=C3CC=CC3=CC=C21 KXYGKDBONOVZOM-UHFFFAOYSA-N 0.000 description 4
- BSHJHVHMLRKHBZ-UHFFFAOYSA-N 2-ethyl-1h-indene Chemical class C1=CC=C2CC(CC)=CC2=C1 BSHJHVHMLRKHBZ-UHFFFAOYSA-N 0.000 description 4
- YSAXEHWHSLANOM-UHFFFAOYSA-N 2-methyl-1h-indene Chemical class C1=CC=C2CC(C)=CC2=C1 YSAXEHWHSLANOM-UHFFFAOYSA-N 0.000 description 4
- XFNIQDLAPZZUMH-UHFFFAOYSA-N 2-methyl-4,6-di(propan-2-yl)-1h-indene Chemical class CC(C)C1=CC(C(C)C)=CC2=C1C=C(C)C2 XFNIQDLAPZZUMH-UHFFFAOYSA-N 0.000 description 4
- PALKYCKNNSVUHG-UHFFFAOYSA-N 2-methyl-4-phenyl-2,3-dihydro-1h-indene Chemical compound C=12CC(C)CC2=CC=CC=1C1=CC=CC=C1 PALKYCKNNSVUHG-UHFFFAOYSA-N 0.000 description 4
- RKJHJMAZNPASHY-UHFFFAOYSA-N 2-methyl-9h-fluorene Chemical class C1=CC=C2C3=CC=C(C)C=C3CC2=C1 RKJHJMAZNPASHY-UHFFFAOYSA-N 0.000 description 4
- COOKKJGOGWACMY-UHFFFAOYSA-N 3-methyl-1h-indene Chemical class C1=CC=C2C(C)=CCC2=C1 COOKKJGOGWACMY-UHFFFAOYSA-N 0.000 description 4
- QKTNNHZEFGFOQG-UHFFFAOYSA-N 3-tert-butyl-1h-indene Chemical class C1=CC=C2C(C(C)(C)C)=CCC2=C1 QKTNNHZEFGFOQG-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- SXHYRWYROWWEMH-UHFFFAOYSA-N C(C)C1CC2=CC=CC(=C2C1)C1=CC=CC=C1 Chemical compound C(C)C1CC2=CC=CC(=C2C1)C1=CC=CC=C1 SXHYRWYROWWEMH-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- UCIKZESDXASJNG-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C([Zr+2])C=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C([Zr+2])C=CC2=C1 UCIKZESDXASJNG-UHFFFAOYSA-L 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- SPFZKMMPGXBEPX-UHFFFAOYSA-N 1-propyl-1h-indene Chemical compound C1=CC=C2C(CCC)C=CC2=C1 SPFZKMMPGXBEPX-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- LQOBMKYCRQDMTN-UHFFFAOYSA-N 3-(2-ethylphenyl)pentan-3-amine;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1C(N)(CC)CC LQOBMKYCRQDMTN-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- IEKPDJDYFASRFB-UHFFFAOYSA-N 1-ethyl-1h-indene Chemical compound C1=CC=C2C(CC)C=CC2=C1 IEKPDJDYFASRFB-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- FWCKYKDIIQDTRL-UHFFFAOYSA-N 1-tert-butyl-2-methylcyclopenta-1,3-diene Chemical compound CC1=C(C(C)(C)C)CC=C1 FWCKYKDIIQDTRL-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-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
- QWJWPDHACGGABF-UHFFFAOYSA-N 5,5-dimethylcyclopenta-1,3-diene Chemical compound CC1(C)C=CC=C1 QWJWPDHACGGABF-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- CYVBVBFBHYTUJO-UHFFFAOYSA-N C1=CC=CC1.C1(=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1=CC=CC1.C1(=CC=CC=C1)C1=CC=CC=C1 CYVBVBFBHYTUJO-UHFFFAOYSA-N 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 description 2
- PZBZKFMEUOKJCL-UHFFFAOYSA-N CCC1=CC=CC1.CN(C)C Chemical compound CCC1=CC=CC1.CN(C)C PZBZKFMEUOKJCL-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- XXLYENUUBJNSOL-UHFFFAOYSA-N cyclopenta-1,3-diene N,N-dimethylmethanamine Chemical compound CN(C)C.C1C=CC=C1 XXLYENUUBJNSOL-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- MRNOGRFKOQUFBC-UHFFFAOYSA-N 1-butyl-1h-indene Chemical group C1=CC=C2C(CCCC)C=CC2=C1 MRNOGRFKOQUFBC-UHFFFAOYSA-N 0.000 description 1
- BLPGWZAQVVZJOA-UHFFFAOYSA-N 1-butyl-9h-fluorene Chemical group C1C2=CC=CC=C2C2=C1C(CCCC)=CC=C2 BLPGWZAQVVZJOA-UHFFFAOYSA-N 0.000 description 1
- NWFVDKHZNWEXAD-UHFFFAOYSA-N 1-tert-butylcyclopenta-1,3-diene Chemical compound CC(C)(C)C1=CC=CC1 NWFVDKHZNWEXAD-UHFFFAOYSA-N 0.000 description 1
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- DFZYPLLGAQIQTD-UHFFFAOYSA-N 2,7-ditert-butyl-9h-fluorene Chemical compound CC(C)(C)C1=CC=C2C3=CC=C(C(C)(C)C)C=C3CC2=C1 DFZYPLLGAQIQTD-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- AHQZRFBZJSCKAV-UHFFFAOYSA-N 2-methylcyclopenta-1,3-diene Chemical compound CC1=CCC=C1 AHQZRFBZJSCKAV-UHFFFAOYSA-N 0.000 description 1
- WNMZSWBQRXSFFM-UHFFFAOYSA-N 2-tert-butylcyclopenta-1,3-diene Chemical compound CC(C)(C)C1=CCC=C1 WNMZSWBQRXSFFM-UHFFFAOYSA-N 0.000 description 1
- IUHDHPFKWALSKK-UHFFFAOYSA-N C(C)(C)(C)C=1CC2=C(C=CC=C2C1)C(C)(C)C Chemical class C(C)(C)(C)C=1CC2=C(C=CC=C2C1)C(C)(C)C IUHDHPFKWALSKK-UHFFFAOYSA-N 0.000 description 1
- UTOQPLFXNJEMJL-UHFFFAOYSA-N CCC.C=CC=CC Chemical compound CCC.C=CC=CC UTOQPLFXNJEMJL-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- UGVVIPAIDGTTNN-UHFFFAOYSA-N C[Zr]C Chemical compound C[Zr]C UGVVIPAIDGTTNN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- KKDBZWZRJNRBGA-UHFFFAOYSA-L Cl[Ti]Cl.[CH]1C=CC=C1 Chemical compound Cl[Ti]Cl.[CH]1C=CC=C1 KKDBZWZRJNRBGA-UHFFFAOYSA-L 0.000 description 1
- 244000124209 Crocus sativus Species 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 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
- 239000012043 crude product Substances 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- HXWGXXDEYMNGCT-UHFFFAOYSA-M decyl(trimethyl)azanium;chloride Chemical class [Cl-].CCCCCCCCCC[N+](C)(C)C HXWGXXDEYMNGCT-UHFFFAOYSA-M 0.000 description 1
- PLMFYJJFUUUCRZ-UHFFFAOYSA-M decyltrimethylammonium bromide Chemical class [Br-].CCCCCCCCCC[N+](C)(C)C PLMFYJJFUUUCRZ-UHFFFAOYSA-M 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/15—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentadiene ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/867—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an aldehyde or a ketone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19523595A DE19523595A1 (de) | 1995-06-30 | 1995-06-30 | Verfahren zur Herstellung einer kohlenstoffverbrückten Biscyclopentadienverbindung |
| DE19523595.9 | 1995-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1148038A CN1148038A (zh) | 1997-04-23 |
| CN1068575C true CN1068575C (zh) | 2001-07-18 |
Family
ID=7765522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96110141A Expired - Lifetime CN1068575C (zh) | 1995-06-30 | 1996-06-27 | 碳桥式双环戊二烯化合物的合成工艺 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5670681A (enExample) |
| EP (1) | EP0751143B1 (enExample) |
| JP (1) | JP3856870B2 (enExample) |
| KR (1) | KR970001287A (enExample) |
| CN (1) | CN1068575C (enExample) |
| AT (1) | ATE205175T1 (enExample) |
| AU (1) | AU5619996A (enExample) |
| BR (1) | BR9602932A (enExample) |
| CA (1) | CA2180219A1 (enExample) |
| DE (2) | DE19523595A1 (enExample) |
| NO (1) | NO962760L (enExample) |
| TW (1) | TW399035B (enExample) |
| ZA (1) | ZA965506B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1272924B (it) * | 1995-01-23 | 1997-07-01 | Spherilene Srl | Procedimento per la preparazione di composti ciclopentadienilici e composti cosi' ottenibili |
| DE19637669A1 (de) | 1996-09-16 | 1998-03-19 | Hoechst Ag | Verfahren zur Herstellung einer methylenverbrückten Biscyclopentadienylverbindung |
| PL330222A1 (en) | 1997-03-29 | 1999-05-10 | Montell Technology Company Bv | Metalocenes and catalysts for use in polymerisation of olefins |
| CA2257132A1 (en) * | 1997-03-29 | 1998-10-08 | Montell Technology Company B.V. | Process for preparing cyclopentadienyl compounds |
| US7273957B2 (en) * | 1999-05-04 | 2007-09-25 | Catalytic Distillation Technologies | Process for the production of gasoline stocks |
| DE19922020A1 (de) * | 1999-05-12 | 2000-11-16 | Targor Gmbh | Übergangsmetallverbindung, Katalysatorsystem, Verfahren zu seiner Herstellung und seine Verwendung zur Polymerisation von Olefinen |
| EP1095944B1 (en) | 1999-10-26 | 2004-03-17 | Repsol Quimica S.A. | Single-carbon bridged bis cyclopentadienyl compounds and metallocene complexes thereof |
| US7145049B2 (en) * | 2003-07-25 | 2006-12-05 | Catalytic Distillation Technologies | Oligomerization process |
| US7157592B1 (en) | 2005-12-30 | 2007-01-02 | Property Development Corporation International Ltd., Inc. | Method for producing organo-metallic compounds of cyclopentadiene |
| KR200453882Y1 (ko) * | 2009-06-26 | 2011-06-01 | 한국전력공사 | 송풍기용 제어장치 |
| RU2413711C1 (ru) * | 2009-07-15 | 2011-03-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Способ получения олигомеров индена |
| RU2415122C1 (ru) * | 2009-07-15 | 2011-03-27 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Способ получения димеров индена |
| US20110179697A1 (en) * | 2010-01-27 | 2011-07-28 | Asiacom Group Investments, Inc. | Method for Production of Metallocenes Preventing Nitrogen Oxides Emission in Combustion of Fuels in Motors |
| CN103664469B (zh) * | 2012-09-18 | 2015-05-27 | 中国石油天然气股份有限公司 | 一类含环戊二烯的星形化合物及其制备方法 |
| EP3686209A1 (en) | 2019-01-28 | 2020-07-29 | LANXESS Organometallics GmbH | Process for producing metallocenes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5030757A (en) * | 1990-05-07 | 1991-07-09 | Ethyl Corporation | Phase transfer catalyst recovery |
| US5420320A (en) * | 1994-06-08 | 1995-05-30 | Phillips Petroleum Company | Method for preparing cyclopentadienyl-type ligands and metallocene compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892851A (en) * | 1988-07-15 | 1990-01-09 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
| DE3929693A1 (de) * | 1989-09-07 | 1991-03-14 | Hoechst Ag | Verfahren zur herstellung eines polyolefinwachses |
| ATE198893T1 (de) * | 1993-11-24 | 2001-02-15 | Targor Gmbh | Metallocene, verfahren zu ihrer herstellung und ihrer verwendung als katalysatoren |
| DE4406110A1 (de) * | 1994-02-25 | 1995-08-31 | Witco Gmbh | Verbrückte Cyclopentadienylmagnesium-Verbindungen und Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Metallocenen |
| US5563284A (en) * | 1994-09-09 | 1996-10-08 | Phillips Petroleum Company | Cyclopentadienyl-type ligands, metallocenes, catalyst systems, preparation, and use |
| US5569746A (en) * | 1995-01-23 | 1996-10-29 | Albemarle Corporation | Process for preparing alkylsubstituted cyclopentadienyl metallocene compounds |
| IT1272924B (it) * | 1995-01-23 | 1997-07-01 | Spherilene Srl | Procedimento per la preparazione di composti ciclopentadienilici e composti cosi' ottenibili |
-
1995
- 1995-06-30 DE DE19523595A patent/DE19523595A1/de not_active Ceased
-
1996
- 1996-06-19 EP EP96109834A patent/EP0751143B1/de not_active Expired - Lifetime
- 1996-06-19 AT AT96109834T patent/ATE205175T1/de not_active IP Right Cessation
- 1996-06-19 DE DE59607614T patent/DE59607614D1/de not_active Expired - Lifetime
- 1996-06-26 AU AU56199/96A patent/AU5619996A/en not_active Abandoned
- 1996-06-27 CN CN96110141A patent/CN1068575C/zh not_active Expired - Lifetime
- 1996-06-28 ZA ZA965506A patent/ZA965506B/xx unknown
- 1996-06-28 NO NO962760A patent/NO962760L/no not_active Application Discontinuation
- 1996-06-28 KR KR1019960024830A patent/KR970001287A/ko not_active Withdrawn
- 1996-06-28 CA CA002180219A patent/CA2180219A1/en not_active Abandoned
- 1996-06-28 BR BR9602932A patent/BR9602932A/pt not_active IP Right Cessation
- 1996-06-28 US US08/671,956 patent/US5670681A/en not_active Expired - Lifetime
- 1996-07-01 TW TW085107948A patent/TW399035B/zh not_active IP Right Cessation
- 1996-07-01 JP JP17098196A patent/JP3856870B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5030757A (en) * | 1990-05-07 | 1991-07-09 | Ethyl Corporation | Phase transfer catalyst recovery |
| US5420320A (en) * | 1994-06-08 | 1995-05-30 | Phillips Petroleum Company | Method for preparing cyclopentadienyl-type ligands and metallocene compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9602932A (pt) | 1998-04-22 |
| ZA965506B (en) | 1997-01-31 |
| JPH0920694A (ja) | 1997-01-21 |
| EP0751143A2 (de) | 1997-01-02 |
| KR970001287A (ko) | 1997-01-24 |
| JP3856870B2 (ja) | 2006-12-13 |
| DE19523595A1 (de) | 1997-01-02 |
| DE59607614D1 (de) | 2001-10-11 |
| CN1148038A (zh) | 1997-04-23 |
| ATE205175T1 (de) | 2001-09-15 |
| NO962760D0 (no) | 1996-06-28 |
| CA2180219A1 (en) | 1996-12-31 |
| TW399035B (en) | 2000-07-21 |
| EP0751143B1 (de) | 2001-09-05 |
| EP0751143A3 (de) | 1998-05-06 |
| NO962760L (no) | 1997-01-02 |
| US5670681A (en) | 1997-09-23 |
| AU5619996A (en) | 1997-01-09 |
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