JP6884756B2 - α−ダマスコンを調製する方法 - Google Patents
α−ダマスコンを調製する方法 Download PDFInfo
- Publication number
- JP6884756B2 JP6884756B2 JP2018508711A JP2018508711A JP6884756B2 JP 6884756 B2 JP6884756 B2 JP 6884756B2 JP 2018508711 A JP2018508711 A JP 2018508711A JP 2018508711 A JP2018508711 A JP 2018508711A JP 6884756 B2 JP6884756 B2 JP 6884756B2
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- JP
- Japan
- Prior art keywords
- dimethylundeca
- trien
- nitric acid
- mixture
- reaction
- 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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- CRIGTVCBMUKRSL-UHFFFAOYSA-N alpha-Damascone Natural products CC=CC(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-UHFFFAOYSA-N 0.000 title description 12
- CRIGTVCBMUKRSL-FNORWQNLSA-N 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enone Chemical compound C\C=C\C(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-FNORWQNLSA-N 0.000 title description 8
- -1 2,6,6-trimethylcyclohex-2-en-1-yl Chemical group 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 59
- 239000011541 reaction mixture Substances 0.000 claims description 40
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 33
- BGAGVDYLLDRYCL-ZRDIBKRKSA-N (5e)-6,10-dimethylundeca-1,5,9-trien-4-ol Chemical compound CC(C)=CCC\C(C)=C\C(O)CC=C BGAGVDYLLDRYCL-ZRDIBKRKSA-N 0.000 claims description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 32
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 27
- 229910017604 nitric acid Inorganic materials 0.000 claims description 26
- CBZXDMDVOPIIKD-UHFFFAOYSA-N 6,10-dimethylundeca-1,5,9-trien-4-one Chemical compound CC(C)=CCCC(C)=CC(=O)CC=C CBZXDMDVOPIIKD-UHFFFAOYSA-N 0.000 claims description 25
- 229910003480 inorganic solid Inorganic materials 0.000 claims description 20
- 239000007800 oxidant agent Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims description 17
- 239000011780 sodium chloride Substances 0.000 claims description 16
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 9
- 229910001882 dioxygen Inorganic materials 0.000 claims description 9
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 9
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 7
- BCJCJALHNXSXKE-UHFFFAOYSA-N azado Chemical group C1C(C2)CC3CC1N([O])C2C3 BCJCJALHNXSXKE-UHFFFAOYSA-N 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229910002001 transition metal nitrate Inorganic materials 0.000 claims description 4
- BGAGVDYLLDRYCL-UHFFFAOYSA-N 6,10-dimethylundeca-1,5,9-trien-4-ol Chemical compound CC(C)=CCCC(C)=CC(O)CC=C BGAGVDYLLDRYCL-UHFFFAOYSA-N 0.000 claims description 3
- WUXMSJQQHBZNIK-UHFFFAOYSA-N 9-hydroxy-9-azabicyclo[3.3.1]nonane Chemical group C1CCC2CCCC1N2O WUXMSJQQHBZNIK-UHFFFAOYSA-N 0.000 claims description 2
- LNMXAQDYIPHBOF-UHFFFAOYSA-N C1C(C2)C3CC2NC1C3 Chemical compound C1C(C2)C3CC2NC1C3 LNMXAQDYIPHBOF-UHFFFAOYSA-N 0.000 claims description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 2
- 150000008045 alkali metal halides Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims 1
- FVHSUDLWWSRVOL-UHFFFAOYSA-N n-tert-butyl-2-methyl-1-phenylpropan-1-amine Chemical compound CC(C)(C)NC(C(C)C)C1=CC=CC=C1 FVHSUDLWWSRVOL-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000007254 oxidation reaction Methods 0.000 description 28
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 239000001301 oxygen Substances 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000006317 isomerization reaction Methods 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 14
- 229940043350 citral Drugs 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000001590 oxidative effect Effects 0.000 description 11
- 238000007363 ring formation reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000011261 inert gas Substances 0.000 description 10
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- SZQUEWJRBJDHSM-UHFFFAOYSA-N iron(3+);trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SZQUEWJRBJDHSM-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CYSFUFRXDOAOMP-UHFFFAOYSA-M magnesium;prop-1-ene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C=C CYSFUFRXDOAOMP-UHFFFAOYSA-M 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 241000134874 Geraniales Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- LLYCMZGLHLKPPU-UHFFFAOYSA-M perbromate Chemical compound [O-]Br(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-M 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 125000004971 nitroalkyl group Chemical group 0.000 description 3
- 150000004967 organic peroxy acids Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 241000894007 species Species 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CHOOCIQDWNAXQQ-UHFFFAOYSA-N 1,5,5-trimethylcyclohexene Chemical compound CC1=CCCC(C)(C)C1 CHOOCIQDWNAXQQ-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- MOQGCGNUWBPGTQ-UHFFFAOYSA-N 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde Chemical compound CC1=C(C=O)C(C)(C)CCC1 MOQGCGNUWBPGTQ-UHFFFAOYSA-N 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000004808 allyl alcohols Chemical class 0.000 description 2
- ZVZRJSHOOULAGB-UHFFFAOYSA-N alpha-Cyclocitral Chemical compound CC1=CCCC(C)(C)C1C=O ZVZRJSHOOULAGB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Chemical compound [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical group [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical class OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- AAUNBWYUJICUKP-UHFFFAOYSA-N hypoiodite Chemical compound I[O-] AAUNBWYUJICUKP-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- WQMNNHNWITXOAH-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].CC=[CH-] WQMNNHNWITXOAH-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 229910001960 metal nitrate Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000002976 peresters Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- JAAGVIUFBAHDMA-UHFFFAOYSA-M rubidium bromide Chemical compound [Br-].[Rb+] JAAGVIUFBAHDMA-UHFFFAOYSA-M 0.000 description 2
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CBZXDMDVOPIIKD-ZRDIBKRKSA-N (5E)-6,10-dimethylundeca-1,5,9-trien-4-one Chemical group C\C(=C/C(CC=C)=O)\CCC=C(C)C CBZXDMDVOPIIKD-ZRDIBKRKSA-N 0.000 description 1
- CVBRKUMLJLIZGY-VOTSOKGWSA-N (e)-4-methylhept-4-en-3-ol Chemical compound CC\C=C(/C)C(O)CC CVBRKUMLJLIZGY-VOTSOKGWSA-N 0.000 description 1
- CRIGTVCBMUKRSL-SMYYYNMVSA-N (z)-1-[(1r)-2,6,6-trimethylcyclohex-2-en-1-yl]but-2-en-1-one Chemical compound C\C=C/C(=O)[C@H]1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-SMYYYNMVSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- NALZTFARIYUCBY-UHFFFAOYSA-N 1-nitrobutane Chemical compound CCCC[N+]([O-])=O NALZTFARIYUCBY-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- CNIGTNPXWSLRPH-UHFFFAOYSA-N 2,2,4-trimethyl-1-oxidoimidazol-1-ium Chemical compound CC1=NC(C)(C)[N+]([O-])=C1 CNIGTNPXWSLRPH-UHFFFAOYSA-N 0.000 description 1
- 239000001895 2,6,6-trimethylcyclohex-2-ene-1-carbaldehyde Substances 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- NFPBWZOKGZKYRE-UHFFFAOYSA-N 2-propan-2-ylperoxypropane Chemical compound CC(C)OOC(C)C NFPBWZOKGZKYRE-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- YKXLOLXPAVQFLX-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienal Chemical compound CC(C)=CCCC(C)=CC=O.CC(C)=CCCC(C)=CC=O YKXLOLXPAVQFLX-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UXBLSWOMIHTQPH-UHFFFAOYSA-N 4-acetamido-TEMPO Chemical compound CC(=O)NC1CC(C)(C)N([O])C(C)(C)C1 UXBLSWOMIHTQPH-UHFFFAOYSA-N 0.000 description 1
- VHIVJUNIYOCPSI-UHFFFAOYSA-N 6,10-dimethylundeca-1,5,9-triene Chemical compound CC(C)=CCCC(C)=CCCC=C VHIVJUNIYOCPSI-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- DOFUNOBJYCBVBS-UHFFFAOYSA-N I(=O)(=O)O.N(=O)O Chemical compound I(=O)(=O)O.N(=O)O DOFUNOBJYCBVBS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101100496858 Mus musculus Colec12 gene Proteins 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910001964 alkaline earth metal nitrate Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- PRKQVKDSMLBJBJ-UHFFFAOYSA-N ammonium carbonate Chemical class N.N.OC(O)=O PRKQVKDSMLBJBJ-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000011162 ammonium carbonates Nutrition 0.000 description 1
- DVARTQFDIMZBAA-UHFFFAOYSA-O ammonium nitrate Chemical class [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N but-2-enal Chemical compound CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Inorganic materials [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-M chlorite Chemical compound [O-]Cl=O QBWCMBCROVPCKQ-UHFFFAOYSA-M 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940125782 compound 2 Drugs 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
- SOHOFAQPQODRIC-UHFFFAOYSA-N deca-1,5,9-trien-4-one Chemical compound C=CCCC=CC(=O)CC=C SOHOFAQPQODRIC-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- GEOVEUCEIQCBKH-UHFFFAOYSA-N hypoiodous acid Chemical compound IO GEOVEUCEIQCBKH-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- LLYCMZGLHLKPPU-UHFFFAOYSA-N perbromic acid Chemical compound OBr(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Inorganic materials [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 1
- WFUBYPSJBBQSOU-UHFFFAOYSA-M rubidium iodide Inorganic materials [Rb+].[I-] WFUBYPSJBBQSOU-UHFFFAOYSA-M 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical class [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- DAFQZPUISLXFBF-UHFFFAOYSA-N tetraoxathiolane 5,5-dioxide Chemical compound O=S1(=O)OOOO1 DAFQZPUISLXFBF-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/39—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
a)6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールを用意すること、
b)少なくとも1種の有機ニトロキシルラジカル、少なくとも1種の硝酸化合物及び無機固体の存在下、酸化剤で、ステップa)において用意された6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールを酸化して、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを生成すること、
c)ステップb)において得られた6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを、酸と反応させて、1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-2-エン-1-オンを生成すること
を含む、方法に関するものである。
本発明によれば、ステップa)は、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールの調製を含む。6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールは、例として、3,7-ジメチルオクタ-2,6-ジエナール(シトラール)をアリルマグネシウム化合物と反応させることによって、並びに当業者にとって既知であり、先行技術分野において十分に記載されているその他の方法によって、3,7-ジメチルオクタ-2,6-ジエナールから好都合な方法で得ることができる。
- S1群:脂肪族及び脂環式炭化水素、特に、5から12個の炭素原子を有する、アルカン及びシクロアルカン、並びにこれらのアルカン及びシクロアルカンの混合物、例えば、ペンタン、ヘキサン、ヘプタン、オクタン、リグロイン、石油エーテル又はシクロヘキサン、
- S2群:芳香族炭化水素、例えば、ベンゼン、トルエン、キシレン、エチルベンゼン又はテトラリン、及びそれらの混合物、
- S3群:脂肪族及び脂環式エーテル、例えば、メチル-tert.-ブチルエーテル、ジブチルエーテル、テトラヒドロフラン、1,4-ジオキサン又は1,2-ジメトキシエタン、
並びに前述の溶媒の混合物。
本発明のステップb)は、少なくとも1種の有機ニトロキシルラジカル、少なくとも1種の硝酸化合物及び無機固体の存在下、酸化剤で、ステップa)において用意された6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールを酸化して、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを生成することを含む。
- 適切なハロゲンは、例として、フッ素又は塩素である。
- 適切な塩素のオキシアニオンは、例として、次亜塩素酸塩、亜塩素酸塩、塩素酸塩又は過塩素酸塩である。
- 適切な臭素のオキシアニオンは、例として、次亜臭素酸塩、亜臭素酸塩、臭素酸塩又は過臭素酸塩である。
- 適切なヨウ素のオキシアニオンは、例として、次亜ヨウ素酸塩、亜ヨウ素酸塩、ヨウ素酸塩又は過ヨウ素酸塩である。
- 適切なジアルキルペルオキシドは、例として、ジイソプロピルペルオキシド又はジ(tert.-ブチル)ペルオキシドである。
- 適切な、有機又は無機過酸は、例えば、メタクロロ過安息香酸又は過酢酸、ペルオキソ二硫酸又はペルオキソ一硫酸である。
- 適切なペルエステルは、例として、ペルアセテート、例えば、tert.-ブチルペルアセテート又はtert.-ブチルフェニルペルアセテートである。
- 適切なヒドロペルオキシドは、例として、tert.-ブチルヒドロペルオキシドである。
- S1群:脂肪族及び脂環式炭化水素、特に、5から12個の炭素原子を有する、アルカン及びシクロアルカン、並びにこれらのアルカン及びシクロアルカンの混合物、例えば、ペンタン、ヘキサン、ヘプタン、オクタン、リグロイン、石油エーテル又はシクロヘキサン、
- S2群:芳香族炭化水素、例えば、ベンゼン、トルエン、キシレン、エチルベンゼン又はテトラリン、及びそれらの混合物、
- S3群:脂肪族及び脂環式エーテル、例えば、メチル-tert.-ブチルエーテル、ジブチルエーテル、テトラヒドロフラン、1,4-ジオキサン又は1,2-ジメトキエタン、
- S4群:ハロゲン化脂肪族炭化水素、例えば、ジクロロメタン、トリクロロメタン、テトラクロロメタン又はジクロロエタン、及びそれらの混合物、
- S5群:ハロゲン化芳香族炭化水素、例えば、クロロベンゼン、ジクロロベンゼン、2-クロロトルエン、3-クロロトルエン又は4-クロロトルエン、及びそれらの混合物、
並びに前述の溶媒の混合物。
本発明のステップc)は、ステップb)において得られた6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを酸と反応させて、1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-2-エン-1-オンを生成することを含む。
所望であれば、生成混合物中の1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-2-エン-1-オンの割合は、少量の1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-3-エン-1-オンを含む、本発明のステップc)において得られた1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-2-エン-1-オンに、追加の異性化ステップを受けさせることによって、さらに増加させてもよい。
シトラールからの6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールの合成(ステップa)
0℃から5℃の間の温度を維持しながら、乾燥THF(750ml)中のシトラール(100g、0.65mol)の撹拌された溶液に、アリルマグネシウムクロリド(362.6ml、THF中に2M、0.72mol)を、滴下で加えた。アリルマグネシウムクロリドの完全な添加後に、反応混合物を0℃で1時間撹拌し、反応の進行をTLCによってモニターした。反応の完了後に、混合物を、0〜10℃で飽和塩化アンモニウム溶液(500ml)を加えることによってクエンチした。水性層を酢酸エチル(3X50ml)によって抽出し、組み合わされた有機層を濃縮して、化合物2を127g生成した(99.5%)。
1HNMR (300 MHz, CDCl3) δ 1.53 (s, 3H), 1.61 (s, 6H), 1.94-2.07 (m, 4H), 2.18-2.23 (m, 2H), 4.34-4.36 (m, 1H), 5.01-5.14 (m, 4H), 7.72-5.75 (m, 1H).
TEMPO/硝酸鉄(III)九水和物/NaClを使用する、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンの合成(ステップb)
硝酸鉄(III)九水和物(2.0g、5.1mmol、0.1eq)、TEMPO(0.79g、5.1mmol、0.1eq)及び固体NaCl(0.29g、51mmol、0.1eq)を、25℃でトルエン50mlに加えた。この混合物に、実施例1において得られた6,10-ジメチルウンデカ-1,5,9-トリエン-4-オン(10.0g、51mmol、1eq)を25℃で加え、酸素雰囲気下(O2ガスを、反応混合物に、連続して通過させた)、3時間撹拌した。反応は、TLC及びHPLCによってモニターされ、50%の変換を示した。3時間の撹拌後に、追加量の硝酸鉄(III)九水和物(2.0g、5.1mmol、0.1eq)、TEMPO(0.79g、5.1mmol、0.1eq)、NaCl(0.29g、5.1mmol、0.1eq)を、25℃で反応混合物に再び加え、反応混合物を、次に、さらに2時間撹拌した。ほぼ95%の出発物質の消費後に(TLC及びHPLCに基づく)、反応混合物を、トルエン(20ml)を加えることによって希釈した。反応混合物を濾過して、無機物質を除去し、濾過物を飽和チオ硫酸ナトリウム溶液(150ml)、1N HCl(150ml)、飽和炭酸水素ナトリウム溶液(150ml)、ブライン(150ml)によって洗浄した。組み合わされた有機層を、硫酸ナトリウム上で乾燥させ、濃縮して、カラムクロマトグラフィーによって精製された粗化合物13.0gを生成した。精製された化合物の収率は、出発物質に対して72%であった。その他のバッチについては、粗化合物を蒸留によって精製した。
1HNMR (300 MHz, CDCl3) (EとZの異性体混合物) δ 1.63 (s, 3H), 1.68 (s, 3H), 1.9 (s, 1H), 2.07-2.09 (m,4H), 2.50-2.55 (m, 0.5H), 3.09-3.14 (m,1.5H), 5.0-5.23 (m, 3H), 5.84-5.93 (m, 1H), 6.01 (bs, 1H).
4-OH TEMPO/硝酸鉄(III)九水和物/NaClを使用する、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンの合成(ステップb)
硝酸鉄(III)九水和物(13.3g、32.9mmol、0.1eq)、4-ヒドロキシTEMPO(5.7g、32.9mmol、0.1eq)及び固体NaCl(1.9g、32.9mmol、0.1eq)を、25℃でトルエン350.0mlに加えた。この混合物に、実施例1において得られた6,10-ジメチルウンデカ-1,5,9-トリエン-4-オール(64.0g、329.8mmol、1eq)を加え、酸素雰囲気下(O2ガスを、反応混合物に、連続して通過させた)、45℃で3時間撹拌した。反応は、TLC及びHPLCによってモニターされ、50%の変換を示した。3時間の撹拌後に、追加量の硝酸鉄(III)九水和物(13.3g、32.9mmol、0.1eq)、4-ヒドロキシTEMPO(5.7g、32.9mmol、0.1eq)及びNaCl(1.9g、32.9mmol、0.1eq)を、45℃で反応混合物に再び加え、反応混合物を、次に、さらに2時間撹拌した。ほぼ95%の出発物質の消費後に(TLC及びHPLCに基づく)、反応混合物を、トルエン(100.0ml)を加えることによって希釈した。反応混合物を濾過して、無機物質を除去し、濾過物を飽和チオ硫酸ナトリウム溶液(250.0ml)、1N HCl(250.0ml)、飽和炭酸水素ナトリウム溶液(300.0ml)、ブライン(250.0ml)によって洗浄した。組み合わされた有機層を、硫酸ナトリウム上で乾燥させ、濃縮して、粗化合物61.0gを生成し、80℃/1.8mbarでの真空蒸留によって精製して、生成物30.0g(収率:50%)を得た。
1HNMR (300 MHz, CDCl3) (EとZの異性体混合物) δ 1.63 (s, 3H), 1.68 (s, 3H), 1.9 (s, 1H), 2.07-2.09 (m,4H), 2.50-2.55 (m, 0.5H), 3.09-3.14 (m,1.5H), 5.0-5.23 (m, 3H), 5.84-5.93 (m, 1H), 6.01 (bs, 1H).
TEMPO/硝酸鉄(III)九水和物/LiClを使用する、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンの合成(ステップb)
実施例2の方法を、NaClの代わりにLiClの同じモル量を使用して繰り返した。出発物質の変換は、90%であった。カラムクロマトグラフィーによる精製の後で、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを、70%の収率で得た。
TEMPO/硝酸鉄(III)九水和物/KClを使用する、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンの合成(ステップb)
実施例2の方法を、NaClの代わりにKClの同じモル量を使用して繰り返した。出発物質の変換は、50%であった。カラムクロマトグラフィーによる精製の後で、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを、35%の収率で得た。
HNO3/4-OH TEMPOを使用する、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンの合成(ステップb)
硝酸(70%)(0.22g、2.57mmol、0.1eq)、4-ヒドロキシTEMPO(0.44g、2.57mmol、0.1eq)及び固体NaCl(0.15g、2.57mmol、0.1eq)を、20℃で、ジクロロメタン25.0mlに加えた。この混合物に、実施例1において得られた6,10-ジメチルウンデカ-1,5,9-トリエン-4-オール(5.0g、25.7mmol、1eq)を加え、酸素雰囲気下(O2ガスを、反応混合物に、連続して通過させた)、20℃で3時間撹拌した。反応は、TLC及びHPLCによってモニターされ、50%の変換を示した。3時間の撹拌後に、追加量の硝酸(70%)(0.22g、2.57mmol、0.1eq)、4-ヒドロキシTEMPO(0.44g、2.57mmol、0.1eq)及びNaCl(0.15g、2.57mmol、0.1eq)を、20℃で反応混合物に再び加え、反応混合物を、次に、さらに2時間撹拌した。ほぼ95%の出発物質の消費後に(TLC及びHPLCに基づく)、反応混合物を、トルエン(20.0ml)を加えることによって希釈した。反応混合物を濾過して、無機物質を除去し、濾過物を飽和チオ硫酸ナトリウム溶液(100.0ml)、1N HCl(100.0ml)、飽和炭酸水素ナトリウム溶液(150.0ml)、ブライン(100.0ml)によって洗浄した。組み合わされた有機層を、硫酸ナトリウム上で乾燥させ、濃縮して、粗化合物5.0gを生成し、80℃/1.8mbarでの真空蒸留によって精製して、生成物3.0g(収率:60%)を得た。
1HNMR (300 MHz, CDCl3) (EとZの異性体混合物) δ 1.63 (s, 3H), 1.68 (s, 3H), 1.9 (s, 1H), 2.07-2.09 (m,4H), 2.50-2.55 (m, 0.5H), 3.09-3.14 (m,1.5H), 5.0-5.23 (m, 3H), 5.84-5.93 (m, 1H), 6.01 (bs, 1H).
1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-2-エン-1-オン(α-ダマスコン)の合成(ステップc)
トルエン(20ml)中の1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-2-エン-1-オン(2g、10.4mmol)の溶液に、室温で、リン酸(1.52、15mmol)を加え、混合物を、次に、3時間、80℃まで加熱した。次に、反応混合物を室温まで冷却し、次に、水(20ml)を加えることによってクエンチした。水性層を酢酸エチル(2x20ml)によって抽出し、組み合わされた有機層を、収集し、硫酸ナトリウム上で乾燥させ、濃縮した。粗化合物をカラムクロマトグラフィーによって精製して、45%の収率で所望のα-ダマスコン0.9gを得た。
1HNMR (300 MHz, CDCl3) δ 0.83 (s, 3H), 0.88 (s, 3H), 1.15-1.36 (m, 1H), 1.60 (brs, 3H), 1.64-1.78 (m, 1H), 1.92 (brd, 3H), 2.0-2.25 (m, 2H), 2.90 (s, 1H), 5.55-5.56 (bs, 1H), 6.25 (br d,1H), 6.80-6.86 (m, 1H).
Claims (15)
a)6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールを用意すること、
b)少なくとも1種の有機ニトロキシルラジカル、少なくとも1種の硝酸化合物、及びアルカリ金属ハロゲン化物又はアルカリ土類金属ハロゲン化物から選択される無機固体の存在下、次亜塩素酸塩、過酸化水素又は分子状酸素から選択される酸化剤で、ステップa)において用意された6,10-ジメチルウンデカ-1,5,9-トリエン-4-オールを酸化して、6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを生成すること、
c)ステップb)において得られた6,10-ジメチルウンデカ-1,5,9-トリエン-4-オンを、無機酸から選択される酸と反応させて、1-(2,6,6-トリメチルシクロヘキサ-2-エン-1-イル)ブタ-2-エン-1-オンを生成すること
を含む、方法。
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