JP5916855B2 - シクロヘプテンの製造法 - Google Patents
シクロヘプテンの製造法 Download PDFInfo
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- JP5916855B2 JP5916855B2 JP2014519497A JP2014519497A JP5916855B2 JP 5916855 B2 JP5916855 B2 JP 5916855B2 JP 2014519497 A JP2014519497 A JP 2014519497A JP 2014519497 A JP2014519497 A JP 2014519497A JP 5916855 B2 JP5916855 B2 JP 5916855B2
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- JP
- Japan
- Prior art keywords
- group
- derivative
- cycloheptene
- atoms
- formula
- 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.)
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- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 70
- 239000003054 catalyst Substances 0.000 claims description 38
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 19
- ZCNSOBXQEHNQMJ-UHFFFAOYSA-N heptadeca-1,8-diene Chemical compound CCCCCCCCC=CCCCCCC=C ZCNSOBXQEHNQMJ-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000003197 catalytic effect Effects 0.000 claims description 13
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- UGBFRCHGZFHSBC-UHFFFAOYSA-N cycloheptanecarbaldehyde Chemical compound O=CC1CCCCCC1 UGBFRCHGZFHSBC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001933 cycloheptenes Chemical class 0.000 claims description 7
- 230000006324 decarbonylation Effects 0.000 claims description 7
- 238000006606 decarbonylation reaction Methods 0.000 claims description 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 7
- 238000005895 oxidative decarboxylation reaction Methods 0.000 claims description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 claims description 6
- CIYPNZYEUZQIHN-UHFFFAOYSA-N cycloheptanecarbonyl chloride Chemical compound ClC(=O)C1CCCCCC1 CIYPNZYEUZQIHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 238000006471 dimerization reaction Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002888 oleic acid derivatives Chemical class 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 238000005649 metathesis reaction Methods 0.000 description 20
- -1 chlorine or bromine Chemical class 0.000 description 19
- 238000009835 boiling Methods 0.000 description 18
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
- 238000000066 reactive distillation Methods 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- VJHGSLHHMIELQD-UHFFFAOYSA-N nona-1,8-diene Chemical compound C=CCCCCCC=C VJHGSLHHMIELQD-UHFFFAOYSA-N 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZCNSOBXQEHNQMJ-BMRADRMJSA-N (8e)-heptadeca-1,8-diene Chemical compound CCCCCCCC\C=C\CCCCCC=C ZCNSOBXQEHNQMJ-BMRADRMJSA-N 0.000 description 3
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HSNQNPCNYIJJHT-ISLYRVAYSA-N trans-octadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCC HSNQNPCNYIJJHT-ISLYRVAYSA-N 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- ZRPFJAPZDXQHSM-UHFFFAOYSA-L 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole;dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)(Cl)=C1N(C=2C(=CC(C)=CC=2C)C)CCN1C1=C(C)C=C(C)C=C1C ZRPFJAPZDXQHSM-UHFFFAOYSA-L 0.000 description 2
- RUKVGXGTVPPWDD-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)imidazolidine Chemical group CC1=CC(C)=CC(C)=C1N1CN(C=2C(=CC(C)=CC=2C)C)CC1 RUKVGXGTVPPWDD-UHFFFAOYSA-N 0.000 description 2
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- PAZQYDJGLKSCSI-UHFFFAOYSA-N Heptabarbital Chemical compound C=1CCCCCC=1C1(CC)C(=O)NC(=O)NC1=O PAZQYDJGLKSCSI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 238000010535 acyclic diene metathesis reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- UDWHYAPPVOEOMP-UHFFFAOYSA-L dichloro(phenylsulfanylmethylidene)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CSC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 UDWHYAPPVOEOMP-UHFFFAOYSA-L 0.000 description 2
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- LWRDQHOZTAOILO-UHFFFAOYSA-N incadronic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)NC1CCCCCC1 LWRDQHOZTAOILO-UHFFFAOYSA-N 0.000 description 2
- 229950006971 incadronic acid Drugs 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CCSPVZLISFXOKP-UHFFFAOYSA-N 4-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-3-bromo-2-[(3-bromopyridin-2-yl)-phenylmethyl]-5,6-dichloro-3h-pyridine;ruthenium Chemical compound [Ru].CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=C1C(Cl)=C(Cl)N=C(C(C=2C=CC=CC=2)C=2C(=CC=CN=2)Br)C1Br CCSPVZLISFXOKP-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- LSTKNZAMFRGXCG-WLHGVMLRSA-N Bencyclane fumarate Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=CC=1CC1(OCCCN(C)C)CCCCCC1 LSTKNZAMFRGXCG-WLHGVMLRSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241001125671 Eretmochelys imbricata Species 0.000 description 1
- URNZEXXAAKELRB-UHFFFAOYSA-L FC(C(=O)[O-])(F)F.[Ru+2].CC(C#N)(C)C.CC(C#N)(C)C.CC(C#N)(C)C.CC(C#N)(C)C.FC(C(=O)[O-])(F)F Chemical compound FC(C(=O)[O-])(F)F.[Ru+2].CC(C#N)(C)C.CC(C#N)(C)C.CC(C#N)(C)C.CC(C#N)(C)C.FC(C(=O)[O-])(F)F URNZEXXAAKELRB-UHFFFAOYSA-L 0.000 description 1
- 208000037147 Hypercalcaemia Diseases 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- TUHBQGUMJPQNAC-UHFFFAOYSA-L [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichloro-(3-pyridin-2-ylpropylidene)ruthenium Chemical compound CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=[Ru](Cl)(Cl)=CCCC1=CC=CC=N1 TUHBQGUMJPQNAC-UHFFFAOYSA-L 0.000 description 1
- ZDJCARGGZRTYFH-UHFFFAOYSA-L [1,3-bis(2-methylphenyl)imidazolidin-2-ylidene]-dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)Cl.CC1=CC=CC=C1N1CCN(C=2C(=CC=CC=2)C)[C]1 ZDJCARGGZRTYFH-UHFFFAOYSA-L 0.000 description 1
- XIKDJLYMOIRUHT-UHFFFAOYSA-L [Ru](Cl)Cl.C(=CC(C)C)=C1C(C(CCC1)P(C1CCCCC1)C1CCCCC1)=C1N(CCN1C)C Chemical compound [Ru](Cl)Cl.C(=CC(C)C)=C1C(C(CCC1)P(C1CCCCC1)C1CCCCC1)=C1N(CCN1C)C XIKDJLYMOIRUHT-UHFFFAOYSA-L 0.000 description 1
- IUIWJUFIMGSIMI-UHFFFAOYSA-L [Ru](Cl)Cl.C(C)(C)OC1=C(C=C(C=C1)S(=O)(=O)N(C)C)C=C1C(CCCC1)P(C1CCCCC1)C1CCCCC1 Chemical compound [Ru](Cl)Cl.C(C)(C)OC1=C(C=C(C=C1)S(=O)(=O)N(C)C)C=C1C(CCCC1)P(C1CCCCC1)C1CCCCC1 IUIWJUFIMGSIMI-UHFFFAOYSA-L 0.000 description 1
- UFPRQRPIPUMSSW-UHFFFAOYSA-N [Ru].CC1=C(C(=CC(=C1)C)C)C1(C=C2C(CCCC2Cl)(P(C2CCCCC2)C2CCCCC2)Cl)C(C(=CC=C1)C1=C(C=C(C=C1C)C)C)=C1NCCN1 Chemical compound [Ru].CC1=C(C(=CC(=C1)C)C)C1(C=C2C(CCCC2Cl)(P(C2CCCCC2)C2CCCCC2)Cl)C(C(=CC=C1)C1=C(C=C(C=C1C)C)C)=C1NCCN1 UFPRQRPIPUMSSW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- FYJJXENSONZJRG-UHFFFAOYSA-N bencyclane Chemical compound C=1C=CC=CC=1CC1(OCCCN(C)C)CCCCCC1 FYJJXENSONZJRG-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- PNPBGYBHLCEVMK-UHFFFAOYSA-L benzylidene(dichloro)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-L 0.000 description 1
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 description 1
- UNOMOKBVBBHHMU-UHFFFAOYSA-N benzylidene-dicyclohexyl-(4,4-dichlorocyclohexyl)-lambda5-phosphane ruthenium Chemical compound [Ru].ClC1(Cl)CCC(CC1)P(=Cc1ccccc1)(C1CCCCC1)C1CCCCC1 UNOMOKBVBBHHMU-UHFFFAOYSA-N 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 150000001932 cycloheptanes Chemical class 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- UCDVULRIJNJVEV-UHFFFAOYSA-L dichloro(3-methylbut-2-enylidene)ruthenium;tricyclopentylphosphane Chemical compound Cl[Ru]Cl.[CH][CH][C](C)C.C1CCCC1P(C1CCCC1)C1CCCC1.C1CCCC1P(C1CCCC1)C1CCCC1 UCDVULRIJNJVEV-UHFFFAOYSA-L 0.000 description 1
- HVJJUDAMOHYMRL-UHFFFAOYSA-L dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)Cl HVJJUDAMOHYMRL-UHFFFAOYSA-L 0.000 description 1
- KMKCJXPECJFQPQ-UHFFFAOYSA-L dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium;tricyclohexylphosphane Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1 KMKCJXPECJFQPQ-UHFFFAOYSA-L 0.000 description 1
- NMUNQTSQYLEOMN-UHFFFAOYSA-L dichloro-[4,5-dimethyl-1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]-(thiophen-2-ylmethylidene)ruthenium;tricyclohexylphosphane Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1.C=1C=CSC=1C=[Ru](Cl)(Cl)=C1N(C=2C(=CC(C)=CC=2C)C)C(C)=C(C)N1C1=C(C)C=C(C)C=C1C NMUNQTSQYLEOMN-UHFFFAOYSA-L 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011984 grubbs catalyst Substances 0.000 description 1
- 229940016462 heptabarbital Drugs 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000011987 hoveyda–grubbs catalyst Substances 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 208000030915 hypercalcemia disease Diseases 0.000 description 1
- ATQYNBNTEXNNIK-UHFFFAOYSA-N imidazol-2-ylidene Chemical group [C]1NC=CN1 ATQYNBNTEXNNIK-UHFFFAOYSA-N 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 150000003281 rhenium Chemical class 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2078—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by a transformation in which at least one -C(=O)-O- moiety is eliminated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- 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
-
- 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
- C07C2531/24—Phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11173656 | 2011-07-12 | ||
| EP11173656.7 | 2011-07-12 | ||
| PCT/EP2012/062944 WO2013007561A1 (de) | 2011-07-12 | 2012-07-03 | Verfahren zur herstellung von cyclohepten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014524915A JP2014524915A (ja) | 2014-09-25 |
| JP5916855B2 true JP5916855B2 (ja) | 2016-05-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014519497A Expired - Fee Related JP5916855B2 (ja) | 2011-07-12 | 2012-07-03 | シクロヘプテンの製造法 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2731923B1 (enExample) |
| JP (1) | JP5916855B2 (enExample) |
| KR (1) | KR20140054030A (enExample) |
| CN (1) | CN103649027B (enExample) |
| IN (1) | IN2014CN00746A (enExample) |
| WO (1) | WO2013007561A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX356142B (es) | 2012-06-13 | 2018-05-16 | Basf Se | Metodo para producir cetonas macrociclicas. |
| GB201604110D0 (en) * | 2016-03-10 | 2016-04-20 | Givaudan Sa | Preparation of macrocyclic lactones |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3109040A (en) | 1960-05-23 | 1963-10-29 | Armour & Co | Preparation of terminally unsaturated olefins from aliphatic carboxylic acids |
| US5077447A (en) | 1990-09-28 | 1991-12-31 | Henkel Research Corporation | Process for making olefins |
| WO1996004289A1 (en) | 1992-04-03 | 1996-02-15 | California Institute Of Technology | High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof |
| DE4321692A1 (de) | 1993-06-30 | 1995-01-12 | Basf Ag | Verfahren zur Herstellung von cyclischen Ketonen |
| US5831108A (en) | 1995-08-03 | 1998-11-03 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
| KR100569619B1 (ko) | 1997-06-25 | 2006-04-11 | 시바 스페셜티 케미칼스 홀딩 인크. | 루테늄 및 오스뮴 카르벤 촉매 |
| DE19815275B4 (de) | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
| FR2796639A1 (fr) | 1999-07-21 | 2001-01-26 | Rhodia Chimie Sa | Procede de preparation d'un acide carboxylique |
| DE60140455D1 (de) | 2000-08-10 | 2009-12-24 | Trustees Boston College | Wiederverwendbare methathese-katalysatoren |
| US6759537B2 (en) | 2001-03-23 | 2004-07-06 | California Institute Of Technology | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
| ATE348835T1 (de) | 2002-01-22 | 2007-01-15 | Univ Gent | Metallkomplexe für die metathese |
| EP1394190B1 (de) * | 2002-07-31 | 2007-01-03 | Saltigo GmbH | Metathesekatalysatoren |
| US7411093B2 (en) * | 2004-12-20 | 2008-08-12 | Hoffman-La Roche Inc. | Aminocycloalkanes as DPP-IV inhibitors |
| JP5406525B2 (ja) | 2005-07-04 | 2014-02-05 | ツァナン・サイテック・カンパニー・リミテッド | ルテニウム錯体配位子、ルテニウム錯体、固定化ルテニウム錯体触媒及びその調製方法と用途 |
| JP5612304B2 (ja) * | 2006-04-11 | 2014-10-22 | エージェンシー フォー サイエンス， テクノロジー アンド リサーチ | 閉環メタセシスのための触媒 |
| FR2909382B1 (fr) | 2006-11-30 | 2009-01-23 | Enscr | Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines |
| DE102008008299B3 (de) | 2008-02-08 | 2009-08-13 | Leibniz-Institut für Oberflächenmodifizierung e.V. | Latente photoaktivierbare Präkatalysatoren für die Metathesepolymerisation |
| US8044043B2 (en) * | 2008-04-11 | 2011-10-25 | Bristol-Myers Squibb Company | CGRP receptor antagonists |
| US9410205B2 (en) | 2010-02-18 | 2016-08-09 | New York University | Methods for predicting survival in metastatic melanoma patients |
-
2012
- 2012-07-03 IN IN746CHN2014 patent/IN2014CN00746A/en unknown
- 2012-07-03 WO PCT/EP2012/062944 patent/WO2013007561A1/de not_active Ceased
- 2012-07-03 EP EP12733089.2A patent/EP2731923B1/de not_active Not-in-force
- 2012-07-03 JP JP2014519497A patent/JP5916855B2/ja not_active Expired - Fee Related
- 2012-07-03 CN CN201280034094.3A patent/CN103649027B/zh not_active Expired - Fee Related
- 2012-07-03 KR KR1020147003259A patent/KR20140054030A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013007561A1 (de) | 2013-01-17 |
| CN103649027A (zh) | 2014-03-19 |
| EP2731923B1 (de) | 2015-09-09 |
| IN2014CN00746A (enExample) | 2015-04-03 |
| EP2731923A1 (de) | 2014-05-21 |
| CN103649027B (zh) | 2016-04-20 |
| JP2014524915A (ja) | 2014-09-25 |
| KR20140054030A (ko) | 2014-05-08 |
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