JP4229365B2 - 大環状ケトンの製造方法 - Google Patents
大環状ケトンの製造方法 Download PDFInfo
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- JP4229365B2 JP4229365B2 JP2002567888A JP2002567888A JP4229365B2 JP 4229365 B2 JP4229365 B2 JP 4229365B2 JP 2002567888 A JP2002567888 A JP 2002567888A JP 2002567888 A JP2002567888 A JP 2002567888A JP 4229365 B2 JP4229365 B2 JP 4229365B2
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- JP
- Japan
- Prior art keywords
- vinyl
- cyclododecanol
- macrocyclic
- formula
- methyl
- 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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- 150000002576 ketones Chemical class 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 37
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 23
- -1 alkali metal cation Chemical class 0.000 claims description 19
- XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 17
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- YHKZFLIVVILEFF-UHFFFAOYSA-N 1-ethenylcyclopentadecan-1-ol Chemical compound C=CC1(O)CCCCCCCCCCCCCC1 YHKZFLIVVILEFF-UHFFFAOYSA-N 0.000 claims description 4
- NVTRONXAOSFWKI-UHFFFAOYSA-N 1-ethynylcyclotridecan-1-ol Chemical compound C#CC1(O)CCCCCCCCCCCC1 NVTRONXAOSFWKI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004808 allyl alcohols Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- AOGAEGCZICSVDH-UHFFFAOYSA-N 1-ethenylcyclotetradecan-1-ol Chemical compound C=CC1(O)CCCCCCCCCCCCC1 AOGAEGCZICSVDH-UHFFFAOYSA-N 0.000 claims description 3
- ZFHZNFLGVOTYEV-UHFFFAOYSA-N 1-ethenylcyclotridecan-1-ol Chemical compound C=CC1(O)CCCCCCCCCCCC1 ZFHZNFLGVOTYEV-UHFFFAOYSA-N 0.000 claims description 3
- FZVVUGYGZQTZQV-UHFFFAOYSA-N 1-ethenylcycloundecan-1-ol Chemical compound C=CC1(O)CCCCCCCCCC1 FZVVUGYGZQTZQV-UHFFFAOYSA-N 0.000 claims description 3
- QKVDJLTXEWVTLK-UHFFFAOYSA-N 1-prop-1-en-2-ylcycloundecan-1-ol Chemical compound CC(=C)C1(O)CCCCCCCCCC1 QKVDJLTXEWVTLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- MKXNXOZPYAPYMS-UHFFFAOYSA-N 1-(2-methylprop-1-enyl)cyclododecan-1-ol Chemical compound CC(C)=CC1(O)CCCCCCCCCCC1 MKXNXOZPYAPYMS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 2
- FFVHXGZXDRXFLQ-UHFFFAOYSA-N Hydroxy-cyclopentadecan Natural products OC1CCCCCCCCCCCCCC1 FFVHXGZXDRXFLQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 52
- 239000007858 starting material Substances 0.000 description 29
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- 125000004122 cyclic group Chemical group 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 238000009834 vaporization Methods 0.000 description 13
- 230000008016 vaporization Effects 0.000 description 13
- 239000011261 inert gas Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- ALHUZKCOMYUFRB-UHFFFAOYSA-N 3-methylcyclopentadecan-1-one Chemical compound CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000010453 quartz Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 8
- VHUGWUBIUBBUAF-UHFFFAOYSA-N cyclotridecanone Chemical compound O=C1CCCCCCCCCCCC1 VHUGWUBIUBBUAF-UHFFFAOYSA-N 0.000 description 8
- 238000006049 ring expansion reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000003747 Grignard reaction Methods 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000006062 fragmentation reaction Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- GHCVPKCRECQSRF-UHFFFAOYSA-N 2-methylcyclotetradecan-1-one Chemical compound CC1CCCCCCCCCCCCC1=O GHCVPKCRECQSRF-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000013467 fragmentation Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- IKDAAKTZPNAEIT-UHFFFAOYSA-N 1-ethenylcyclododecan-1-ol Chemical compound C=CC1(O)CCCCCCCCCCC1 IKDAAKTZPNAEIT-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- FUGDHQXYVPQGLJ-UHFFFAOYSA-N cyclotetradecanone Chemical compound O=C1CCCCCCCCCCCCC1 FUGDHQXYVPQGLJ-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- FKMGCQMEGBBGTK-UHFFFAOYSA-N 1-prop-1-ynylcyclododecan-1-ol Chemical compound CC#CC1(O)CCCCCCCCCCC1 FKMGCQMEGBBGTK-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 description 4
- 238000000023 Kugelrohr distillation Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000001793 charged compounds Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- SXOZDDAFVJANJP-UHFFFAOYSA-N cyclodecanone Chemical compound O=C1CCCCCCCCC1 SXOZDDAFVJANJP-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000005337 ground glass Substances 0.000 description 4
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000011403 purification operation Methods 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- YBONARFWOXNGNV-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclododecan-1-ol Chemical compound C=1CCCCC=1C1(O)CCCCCCCCCCC1 YBONARFWOXNGNV-UHFFFAOYSA-N 0.000 description 3
- DEFNUDNHTUZJAL-UHFFFAOYSA-N 1-bromo-2-methylprop-1-ene Chemical compound CC(C)=CBr DEFNUDNHTUZJAL-UHFFFAOYSA-N 0.000 description 3
- IZUAYBMCJPTUJF-UHFFFAOYSA-N 1-ethenylcyclodecan-1-ol Chemical compound C=CC1(O)CCCCCCCCC1 IZUAYBMCJPTUJF-UHFFFAOYSA-N 0.000 description 3
- DCHDUZYXRMNPCU-UHFFFAOYSA-N 1-ethynylcyclododecan-1-ol Chemical compound C#CC1(O)CCCCCCCCCCC1 DCHDUZYXRMNPCU-UHFFFAOYSA-N 0.000 description 3
- ZYJBQFHXDNIOHI-UHFFFAOYSA-N 3,4-dimethylcyclotetradecan-1-one Chemical compound CC1CCCCCCCCCCC(=O)CC1C ZYJBQFHXDNIOHI-UHFFFAOYSA-N 0.000 description 3
- AEDBWISKZYJPSI-UHFFFAOYSA-N 3-methylcycloheptadecan-1-one Chemical compound CC1CCCCCCCCCCCCCCC(=O)C1 AEDBWISKZYJPSI-UHFFFAOYSA-N 0.000 description 3
- VPQWBNWSLZYYFH-UHFFFAOYSA-N 3-methylcyclotetradecan-1-one Chemical compound CC1CCCCCCCCCCCC(=O)C1 VPQWBNWSLZYYFH-UHFFFAOYSA-N 0.000 description 3
- ZXGRDXNTJLIVDJ-UHFFFAOYSA-N 5-methylcycloheptadecan-1-one Chemical compound CC1CCCCCCCCCCCCC(=O)CCC1 ZXGRDXNTJLIVDJ-UHFFFAOYSA-N 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WRSXHGHFNWOBER-UHFFFAOYSA-N 1-ethenylcyclooctan-1-ol Chemical compound C=CC1(O)CCCCCCC1 WRSXHGHFNWOBER-UHFFFAOYSA-N 0.000 description 2
- YVFKCLVVUXZYJI-UHFFFAOYSA-N 1-ethenylcyclopropan-1-ol Chemical compound C=CC1(O)CC1 YVFKCLVVUXZYJI-UHFFFAOYSA-N 0.000 description 2
- MUXFTAAVCXSKLT-UHFFFAOYSA-N 1-prop-1-en-2-ylcyclododecan-1-ol Chemical compound CC(=C)C1(O)CCCCCCCCCCC1 MUXFTAAVCXSKLT-UHFFFAOYSA-N 0.000 description 2
- UBQWVFBZWLCGBB-UHFFFAOYSA-N 1-prop-1-ynylcyclotridecan-1-ol Chemical compound CC#CC1(O)CCCCCCCCCCCC1 UBQWVFBZWLCGBB-UHFFFAOYSA-N 0.000 description 2
- JJUNXABENLJLAY-UHFFFAOYSA-N 2-Methylcyclododecanone Chemical compound CC1CCCCCCCCCCC1=O JJUNXABENLJLAY-UHFFFAOYSA-N 0.000 description 2
- DHDBSYATKTZPGN-UHFFFAOYSA-N 4-ethylcyclotetradecan-1-one Chemical compound CCC1CCCCCCCCCCC(=O)CC1 DHDBSYATKTZPGN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000003997 cyclic ketones Chemical class 0.000 description 2
- KBQDZEMXPBDNGH-UHFFFAOYSA-N cycloheptadecanone Chemical compound O=C1CCCCCCCCCCCCCCCC1 KBQDZEMXPBDNGH-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- UPOSSYJVWXLPTA-UHFFFAOYSA-N cycloundecanone Chemical compound O=C1CCCCCCCCCC1 UPOSSYJVWXLPTA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000005710 macrocyclization reaction Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 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 2
- 210000003739 neck Anatomy 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KVVRUOOPLTUXAP-UHFFFAOYSA-N (1-ethenylcyclopropyl)oxy-trimethylsilane Chemical compound C[Si](C)(C)OC1(C=C)CC1 KVVRUOOPLTUXAP-UHFFFAOYSA-N 0.000 description 1
- 239000001807 (9E)-cycloheptadec-9-en-1-one Substances 0.000 description 1
- NNQDMQVWOWCVEM-NSCUHMNNSA-N (e)-1-bromoprop-1-ene Chemical compound C\C=C\Br NNQDMQVWOWCVEM-NSCUHMNNSA-N 0.000 description 1
- INAPQSHUJPCDID-UHFFFAOYSA-N 1-(cyclohexen-1-yl)dodecan-1-one Chemical compound CCCCCCCCCCCC(=O)C1=CCCCC1 INAPQSHUJPCDID-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- GLXYPBZVIGWFQH-UHFFFAOYSA-N 1-but-2-en-2-ylcyclododecan-1-ol Chemical compound CC=C(C)C1(O)CCCCCCCCCCC1 GLXYPBZVIGWFQH-UHFFFAOYSA-N 0.000 description 1
- BUAKPITZELZWNI-UHFFFAOYSA-N 1-chlorocyclohexene Chemical compound ClC1=CCCCC1 BUAKPITZELZWNI-UHFFFAOYSA-N 0.000 description 1
- PWZIHGYESYMIMT-UHFFFAOYSA-N 1-ethenyl-2-ethylcyclododecan-1-ol Chemical compound CCC1CCCCCCCCCCC1(O)C=C PWZIHGYESYMIMT-UHFFFAOYSA-N 0.000 description 1
- OXVPBNZTCNHKHF-UHFFFAOYSA-N 1-ethenylcyclopentadecan-1-ol 1-ethenylcyclotetradecan-1-ol 1-ethenylcyclotridecan-1-ol 1-ethenylcycloundecan-1-ol Chemical compound C(=C)C1(CCCCCCCCCCCCCC1)O.C(=C)C1(CCCCCCCCCCCCC1)O.C(=C)C1(CCCCCCCCCCCC1)O.C(=C)C1(CCCCCCCCCC1)O OXVPBNZTCNHKHF-UHFFFAOYSA-N 0.000 description 1
- MWUCCOJPMBEKCH-UHFFFAOYSA-N 1-prop-1-enylcyclododecan-1-ol Chemical compound CC=CC1(O)CCCCCCCCCCC1 MWUCCOJPMBEKCH-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PHMRPWPDDRGGGF-UHFFFAOYSA-N 2-bromoprop-1-ene Chemical compound CC(Br)=C PHMRPWPDDRGGGF-UHFFFAOYSA-N 0.000 description 1
- FFOPFQLVZUTCDO-UHFFFAOYSA-N 2-ethylcyclotetradecan-1-one Chemical compound CCC1CCCCCCCCCCCCC1=O FFOPFQLVZUTCDO-UHFFFAOYSA-N 0.000 description 1
- KOAKSLIQYIECBS-UHFFFAOYSA-N 3,3-dimethylcyclotetradecan-1-one Chemical compound CC1(C)CCCCCCCCCCCC(=O)C1 KOAKSLIQYIECBS-UHFFFAOYSA-N 0.000 description 1
- ZZTZYXZLFDBWNT-UHFFFAOYSA-N 4-methylcyclotetradecan-1-one Chemical compound CC1CCCCCCCCCCC(=O)CC1 ZZTZYXZLFDBWNT-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000006550 Oxy-Cope rearrangement reaction Methods 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- BKVIQODYSREJQH-UHFFFAOYSA-M [Br-].CC(C)=C[Mg+] Chemical compound [Br-].CC(C)=C[Mg+] BKVIQODYSREJQH-UHFFFAOYSA-M 0.000 description 1
- LFTYALBVGVNGLI-UHFFFAOYSA-M [Br-].CC([Mg+])=C Chemical compound [Br-].CC([Mg+])=C LFTYALBVGVNGLI-UHFFFAOYSA-M 0.000 description 1
- 238000006657 acyloin condensation reaction Methods 0.000 description 1
- 238000005865 alkene metathesis reaction Methods 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZKVZSBSZTMPBQR-UHFFFAOYSA-N cycloheptadec-9-en-1-one Chemical compound O=C1CCCCCCCC=CCCCCCCC1 ZKVZSBSZTMPBQR-UHFFFAOYSA-N 0.000 description 1
- LXJDKGYSHYYKFJ-UHFFFAOYSA-N cyclohexadecanone Chemical compound O=C1CCCCCCCCCCCCCCC1 LXJDKGYSHYYKFJ-UHFFFAOYSA-N 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- LLWGDNREPDWSRL-UHFFFAOYSA-N cyclopentadec-2-en-1-one Chemical compound O=C1CCCCCCCCCCCCC=C1 LLWGDNREPDWSRL-UHFFFAOYSA-N 0.000 description 1
- RYRDADIPPFMIQM-UHFFFAOYSA-N cyclotetradec-2-en-1-one Chemical compound O=C1CCCCCCCCCCCC=C1 RYRDADIPPFMIQM-UHFFFAOYSA-N 0.000 description 1
- JDPQWHLMBJZURR-UHFFFAOYSA-N decan-5-one Chemical compound CCCCCC(=O)CCCC JDPQWHLMBJZURR-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005828 desilylation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical compound C=CC1CC1 YIWFBNMYFYINAD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- JWIKKFZLSSZWRK-UHFFFAOYSA-N hexadecan-4-one Chemical compound CCCCCCCCCCCCC(=O)CCC JWIKKFZLSSZWRK-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 1
- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
- QBNOPZJAURRQCE-UHFFFAOYSA-M magnesium;prop-1-yne;bromide Chemical compound [Mg+2].[Br-].CC#[C-] QBNOPZJAURRQCE-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- HHQOJAVJSCPMAC-UHFFFAOYSA-N octadecan-7-one Chemical compound CCCCCCCCCCCC(=O)CCCCCC HHQOJAVJSCPMAC-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- ZWCKQRPRESZLKC-UHFFFAOYSA-N pentadec-2-yn-4-ol Chemical compound CCCCCCCCCCCC(O)C#CC ZWCKQRPRESZLKC-UHFFFAOYSA-N 0.000 description 1
- QCJWNUNXTZOXCF-UHFFFAOYSA-N pentadecan-4-one Chemical compound CCCCCCCCCCCC(=O)CCC QCJWNUNXTZOXCF-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004801 process automation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010518 undesired secondary reaction Methods 0.000 description 1
- 238000007158 vacuum pyrolysis Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/607—Unsaturated compounds containing a keto groups being part of a ring of a seven-to twelve-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/413—Saturated compounds containing a keto group being part of a ring of a seven- to twelve-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- 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
-
- 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
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01103613A EP1236707A1 (de) | 2001-02-22 | 2001-02-22 | Verfahren zur Herstellung makrocyclischer Ketone |
| PCT/EP2002/001644 WO2002068372A1 (de) | 2001-02-22 | 2002-02-15 | Verfahren zur herstellung makrocyclischer ketone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004527497A JP2004527497A (ja) | 2004-09-09 |
| JP2004527497A5 JP2004527497A5 (cg-RX-API-DMAC7.html) | 2005-12-22 |
| JP4229365B2 true JP4229365B2 (ja) | 2009-02-25 |
Family
ID=8176502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002567888A Expired - Fee Related JP4229365B2 (ja) | 2001-02-22 | 2002-02-15 | 大環状ケトンの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6951964B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP1236707A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4229365B2 (cg-RX-API-DMAC7.html) |
| CN (2) | CN100371311C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE428680T1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE50213445D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2324338T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002068372A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1236707A1 (de) | 2001-02-22 | 2002-09-04 | Givaudan SA | Verfahren zur Herstellung makrocyclischer Ketone |
| CN101979367B (zh) * | 2010-10-22 | 2014-03-05 | 刘畅 | 3-甲基大环酮的制备方法 |
| CN104379547B (zh) * | 2012-06-13 | 2017-05-17 | 巴斯夫欧洲公司 | 制备大环酮的方法 |
| JP6502884B2 (ja) * | 2016-03-14 | 2019-04-17 | 株式会社 東邦アーステック | 3−メチルシクロアルケノン類の製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2852344A1 (de) * | 1978-12-04 | 1980-06-26 | Basf Ag | In 1-stellung substituierte cyclododecane und cyclododecene und ihre verwendung als duftstoffe |
| JPH11322662A (ja) * | 1998-05-07 | 1999-11-24 | Takasago Internatl Corp | 5−シクロヘキサデセン−1−オンの製造法および製造装置 |
| EP1236707A1 (de) | 2001-02-22 | 2002-09-04 | Givaudan SA | Verfahren zur Herstellung makrocyclischer Ketone |
-
2001
- 2001-02-22 EP EP01103613A patent/EP1236707A1/de not_active Withdrawn
-
2002
- 2002-02-15 CN CNB2006100682788A patent/CN100371311C/zh not_active Expired - Fee Related
- 2002-02-15 AT AT02719851T patent/ATE428680T1/de not_active IP Right Cessation
- 2002-02-15 WO PCT/EP2002/001644 patent/WO2002068372A1/de not_active Ceased
- 2002-02-15 ES ES02719851T patent/ES2324338T3/es not_active Expired - Lifetime
- 2002-02-15 US US10/469,177 patent/US6951964B2/en not_active Expired - Lifetime
- 2002-02-15 CN CNB028044630A patent/CN1255368C/zh not_active Expired - Fee Related
- 2002-02-15 JP JP2002567888A patent/JP4229365B2/ja not_active Expired - Fee Related
- 2002-02-15 EP EP02719851A patent/EP1362023B1/de not_active Expired - Lifetime
- 2002-02-15 DE DE50213445T patent/DE50213445D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1362023B1 (de) | 2009-04-15 |
| DE50213445D1 (cg-RX-API-DMAC7.html) | 2009-05-28 |
| CN1255368C (zh) | 2006-05-10 |
| ATE428680T1 (de) | 2009-05-15 |
| EP1362023A1 (de) | 2003-11-19 |
| CN1824636A (zh) | 2006-08-30 |
| JP2004527497A (ja) | 2004-09-09 |
| ES2324338T3 (es) | 2009-08-05 |
| EP1236707A1 (de) | 2002-09-04 |
| US6951964B2 (en) | 2005-10-04 |
| US20040082816A1 (en) | 2004-04-29 |
| WO2002068372A1 (de) | 2002-09-06 |
| CN1489566A (zh) | 2004-04-14 |
| CN100371311C (zh) | 2008-02-27 |
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