JPS6322034A - 触媒使用によるパラフィンからのオレフィンの合成方法 - Google Patents
触媒使用によるパラフィンからのオレフィンの合成方法Info
- Publication number
- JPS6322034A JPS6322034A JP62108736A JP10873687A JPS6322034A JP S6322034 A JPS6322034 A JP S6322034A JP 62108736 A JP62108736 A JP 62108736A JP 10873687 A JP10873687 A JP 10873687A JP S6322034 A JPS6322034 A JP S6322034A
- Authority
- JP
- Japan
- Prior art keywords
- complex
- alkene
- ethylene
- electrons
- bis
- 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.)
- Granted
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 58
- 239000003054 catalyst Substances 0.000 title claims description 23
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 239000012188 paraffin wax Substances 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 58
- 239000005977 Ethylene Substances 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 49
- -1 cyclopentadienyl iridium Chemical compound 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 229910052741 iridium Inorganic materials 0.000 claims description 19
- 229910052723 transition metal Inorganic materials 0.000 claims description 17
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 15
- 150000003624 transition metals Chemical class 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 10
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 9
- 229910052762 osmium Inorganic materials 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- 150000005671 trienes Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052756 noble gas Inorganic materials 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 27
- 239000007789 gas Substances 0.000 description 20
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 20
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000000370 acceptor Substances 0.000 description 8
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 8
- 150000002503 iridium Chemical class 0.000 description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000003446 ligand Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical group CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- MMNVVSQEHMLKRG-UHFFFAOYSA-L dichloroosmium;1,2,3,4,5,6-hexamethylbenzene Chemical compound Cl[Os]Cl.CC1=C(C)C(C)=C(C)C(C)=C1C MMNVVSQEHMLKRG-UHFFFAOYSA-L 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- YHHHHJCAVQSFMJ-FNORWQNLSA-N (3e)-deca-1,3-diene Chemical compound CCCCCC\C=C\C=C YHHHHJCAVQSFMJ-FNORWQNLSA-N 0.000 description 2
- GVRWIAHBVAYKIZ-FNORWQNLSA-N (e)-dec-3-ene Chemical compound CCCCCC\C=C\CC GVRWIAHBVAYKIZ-FNORWQNLSA-N 0.000 description 2
- SOVOPSCRHKEUNJ-VQHVLOKHSA-N (e)-dec-4-ene Chemical compound CCCCC\C=C\CCC SOVOPSCRHKEUNJ-VQHVLOKHSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 2
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- XBWNESHTWDZGRR-UHFFFAOYSA-N C(=CC=CC)[Ir] Chemical compound C(=CC=CC)[Ir] XBWNESHTWDZGRR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 2
- WUWBOMZBJBMSFD-UHFFFAOYSA-N [Re].[CH]1C=CC=C1 Chemical compound [Re].[CH]1C=CC=C1 WUWBOMZBJBMSFD-UHFFFAOYSA-N 0.000 description 2
- BNNFTTSQQXHNPA-UHFFFAOYSA-N [Rh]C1C=CC=C1 Chemical compound [Rh]C1C=CC=C1 BNNFTTSQQXHNPA-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- YKNMBTZOEVIJCM-UHFFFAOYSA-N dec-2-ene Chemical compound CCCCCCCC=CC YKNMBTZOEVIJCM-UHFFFAOYSA-N 0.000 description 2
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 229960004624 perflexane Drugs 0.000 description 2
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- UHVVNJURNLKSII-UHFFFAOYSA-N 1,2-dimethyl-4-oct-1-enylbenzene Chemical compound CCCCCCC=CC1=CC=C(C)C(C)=C1 UHVVNJURNLKSII-UHFFFAOYSA-N 0.000 description 1
- QLDZGSZDEDZKAS-UHFFFAOYSA-N 1,2-dimethyl-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(C)C(C)=C1 QLDZGSZDEDZKAS-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BFJYEESAIZCXKK-UHFFFAOYSA-N C(=CC=CC)[Re] Chemical compound C(=CC=CC)[Re] BFJYEESAIZCXKK-UHFFFAOYSA-N 0.000 description 1
- QOGYEMAGRQAHCX-UHFFFAOYSA-N C1(C=CC=C1)[OsH3] Chemical class C1(C=CC=C1)[OsH3] QOGYEMAGRQAHCX-UHFFFAOYSA-N 0.000 description 1
- ZWNRNBMUVUUZCL-UHFFFAOYSA-N C1(C=CC=C1)[Tc] Chemical compound C1(C=CC=C1)[Tc] ZWNRNBMUVUUZCL-UHFFFAOYSA-N 0.000 description 1
- ZDMOERFNODLVDF-UHFFFAOYSA-N C=C.C=C.C=C.[Ru] Chemical compound C=C.C=C.C=C.[Ru] ZDMOERFNODLVDF-UHFFFAOYSA-N 0.000 description 1
- VPSULBJUKFCKKU-UHFFFAOYSA-N CC1=C(C(=C(C1(C)[Ir])C)C)C Chemical compound CC1=C(C(=C(C1(C)[Ir])C)C)C VPSULBJUKFCKKU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- OUZOFFLVSMHGTI-UHFFFAOYSA-N [Os].CC1=C(C(=C(C(=C1C)C)C)C)C Chemical compound [Os].CC1=C(C(=C(C(=C1C)C)C)C)C OUZOFFLVSMHGTI-UHFFFAOYSA-N 0.000 description 1
- RTUIXZGDLFAXNI-UHFFFAOYSA-N [Os].CC1=CC=CC=C1 Chemical compound [Os].CC1=CC=CC=C1 RTUIXZGDLFAXNI-UHFFFAOYSA-N 0.000 description 1
- CNEIMZJYKSMEFK-UHFFFAOYSA-N [TcH4] Chemical class [TcH4] CNEIMZJYKSMEFK-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- BCSIRJLFQGSTNT-UHFFFAOYSA-N cyclooctyl(trimethyl)silane Chemical compound C[Si](C)(C)C1CCCCCCC1 BCSIRJLFQGSTNT-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WTZBVIIGQDJARG-UHFFFAOYSA-N decyl(trimethyl)silane Chemical compound CCCCCCCCCC[Si](C)(C)C WTZBVIIGQDJARG-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- LLTSEQQACAHCPR-UHFFFAOYSA-L dichloroosmium;1-methyl-4-propan-2-ylbenzene Chemical compound Cl[Os]Cl.CC(C)C1=CC=C(C)C=C1 LLTSEQQACAHCPR-UHFFFAOYSA-L 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- ZHKRBCQSLSTSAO-UHFFFAOYSA-N dodecyl(trimethyl)silane Chemical compound CCCCCCCCCCCC[Si](C)(C)C ZHKRBCQSLSTSAO-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- DBPBAPSFGLNQOX-UHFFFAOYSA-N iridium trihydride Chemical compound [IrH3] DBPBAPSFGLNQOX-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 210000004196 psta Anatomy 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/50—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor
- C07C5/52—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor with a hydrocarbon as an acceptor, e.g. hydrocarbon disproportionation, i.e. 2CnHp -> CnHp+q + CnHp-q
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/859,696 US4670621A (en) | 1986-05-05 | 1986-05-05 | Catalytic synthesis of olefins from paraffins |
| US859696 | 1986-05-05 | ||
| US37231 | 1987-04-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6322034A true JPS6322034A (ja) | 1988-01-29 |
| JPH0440332B2 JPH0440332B2 (cg-RX-API-DMAC7.html) | 1992-07-02 |
Family
ID=25331522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62108736A Granted JPS6322034A (ja) | 1986-05-05 | 1987-05-01 | 触媒使用によるパラフィンからのオレフィンの合成方法 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4670621A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS6322034A (cg-RX-API-DMAC7.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57202679A (en) * | 1981-06-08 | 1982-12-11 | Matsushita Electric Industrial Co Ltd | Sheathed heater |
| JPH0499733A (ja) * | 1990-08-13 | 1992-03-31 | Agency Of Ind Science & Technol | エチレンを用いる炭化水素の変換方法 |
| JP2018009029A (ja) * | 2014-11-28 | 2018-01-18 | 旭化成株式会社 | 炭化水素の製造方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4751344A (en) * | 1986-05-05 | 1988-06-14 | Ethyl Corporation | Catalytic synthesis of olefins from paraffins |
| WO2005017950A2 (ja) * | 2003-08-19 | 2005-02-24 | Tosoh Corporation | 有機イリジウム化合物、その製法、及び膜の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524898A (en) * | 1968-10-29 | 1970-08-18 | Ethyl Corp | Homogeneous dehydrogenation of paraffins |
| US3721718A (en) * | 1969-03-24 | 1973-03-20 | Phillips Petroleum Co | Conversion of olefins using complexes of fe,ru,os,rh or ir with organoaluminums |
| DE2149934C3 (de) * | 1970-10-13 | 1978-06-08 | Anic S.P.A., Palermo (Italien) | Verfahren zur Herstellung von ungesättigten Kohlenwasserstoffverbindungen |
| US4191846A (en) * | 1973-11-15 | 1980-03-04 | Phillips Petroleum Company | Catalytic dehydrogenation process |
| DE2727245C3 (de) * | 1977-06-16 | 1980-06-26 | Brintzinger, Hans, Prof. Dr., 7750 Konstanz | Polymergebundene CyclopentadienylÜbergangsmetall-Verbindungen und ihre Ligand-Substitutions-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren |
-
1986
- 1986-05-05 US US06/859,696 patent/US4670621A/en not_active Expired - Fee Related
-
1987
- 1987-05-01 JP JP62108736A patent/JPS6322034A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57202679A (en) * | 1981-06-08 | 1982-12-11 | Matsushita Electric Industrial Co Ltd | Sheathed heater |
| JPH0499733A (ja) * | 1990-08-13 | 1992-03-31 | Agency Of Ind Science & Technol | エチレンを用いる炭化水素の変換方法 |
| JP2018009029A (ja) * | 2014-11-28 | 2018-01-18 | 旭化成株式会社 | 炭化水素の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4670621A (en) | 1987-06-02 |
| JPH0440332B2 (cg-RX-API-DMAC7.html) | 1992-07-02 |
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