JP2019069922A - 高純度トリフルオロメチル基置換芳香族ケトンの製造方法 - Google Patents
高純度トリフルオロメチル基置換芳香族ケトンの製造方法 Download PDFInfo
- Publication number
- JP2019069922A JP2019069922A JP2017197648A JP2017197648A JP2019069922A JP 2019069922 A JP2019069922 A JP 2019069922A JP 2017197648 A JP2017197648 A JP 2017197648A JP 2017197648 A JP2017197648 A JP 2017197648A JP 2019069922 A JP2019069922 A JP 2019069922A
- Authority
- JP
- Japan
- Prior art keywords
- substituted aromatic
- aromatic ketone
- trifluoromethyl group
- acid
- grignard reagent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000008365 aromatic ketones Chemical class 0.000 title claims abstract description 56
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title abstract description 9
- -1 benzotrifluoride compound Chemical class 0.000 claims abstract description 45
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 38
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 38
- 230000007062 hydrolysis Effects 0.000 claims abstract description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 24
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 21
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 26
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 3
- YTJFIDLEESXWOY-UHFFFAOYSA-N 1-phenyl-2-(trifluoromethyl)butan-1-one Chemical compound CCC(C(F)(F)F)C(=O)C1=CC=CC=C1 YTJFIDLEESXWOY-UHFFFAOYSA-N 0.000 claims 1
- LBWMQVOHFPLVBY-UHFFFAOYSA-N 3,3,3-trifluoro-1-phenylpropan-1-one Chemical group FC(F)(F)CC(=O)C1=CC=CC=C1 LBWMQVOHFPLVBY-UHFFFAOYSA-N 0.000 claims 1
- FFSQUPZKCFPFEM-UHFFFAOYSA-N 3,3,3-trifluoro-2-methyl-1-phenylpropan-1-one Chemical compound FC(F)(F)C(C)C(=O)C1=CC=CC=C1 FFSQUPZKCFPFEM-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 23
- 239000000194 fatty acid Substances 0.000 abstract description 23
- 229930195729 fatty acid Natural products 0.000 abstract description 23
- 239000000243 solution Substances 0.000 abstract description 20
- 238000004821 distillation Methods 0.000 abstract description 17
- 239000012071 phase Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 18
- 239000012535 impurity Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 14
- 239000002585 base Substances 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- FYDUUODXZQITBF-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1C(F)(F)F FYDUUODXZQITBF-UHFFFAOYSA-N 0.000 description 8
- DGRVQOKCSKDWIH-UHFFFAOYSA-N 1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Cl DGRVQOKCSKDWIH-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- PUSBIOFSWWHNDD-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1C(F)(F)F PUSBIOFSWWHNDD-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZOCAQYAKJXLAQG-UHFFFAOYSA-N 4-chlorobutyl propanoate Chemical compound CCC(=O)OCCCCCl ZOCAQYAKJXLAQG-UHFFFAOYSA-N 0.000 description 5
- DLQYFLOTXUYGDH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl] propanoate Chemical compound CCC(=O)OC1=CC=CC=C1C(F)(F)F DLQYFLOTXUYGDH-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PYLDCZJUHYVOAF-UHFFFAOYSA-N 4-chlorobutyl acetate Chemical compound CC(=O)OCCCCCl PYLDCZJUHYVOAF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- GNFCRFCIPJLCLB-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(F)(F)F GNFCRFCIPJLCLB-UHFFFAOYSA-N 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012847 fine chemical Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 2
- WNUZXEJZBRNZKG-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]butan-1-one Chemical compound CCCC(=O)C1=CC=CC=C1C(F)(F)F WNUZXEJZBRNZKG-UHFFFAOYSA-N 0.000 description 2
- RWXUNIMBRXGNEP-UHFFFAOYSA-N 1-bromo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Br RWXUNIMBRXGNEP-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-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
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZUVAACFIEPYYOP-UHFFFAOYSA-N methoxycyclopropane Chemical compound COC1CC1 ZUVAACFIEPYYOP-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HBEXQIRQRKAXDH-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]pentan-1-one Chemical compound CCCCC(=O)C1=CC=CC=C1C(F)(F)F HBEXQIRQRKAXDH-UHFFFAOYSA-N 0.000 description 1
- OLROVMGGICDDJG-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]butan-1-one Chemical compound CCCC(=O)C1=CC=CC(C(F)(F)F)=C1 OLROVMGGICDDJG-UHFFFAOYSA-N 0.000 description 1
- ABXGMGUHGLQMAW-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C(F)(F)F)=C1 ABXGMGUHGLQMAW-UHFFFAOYSA-N 0.000 description 1
- KBVQREWJMPESHT-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]pentan-1-one Chemical compound CCCCC(=O)C1=CC=CC(C(F)(F)F)=C1 KBVQREWJMPESHT-UHFFFAOYSA-N 0.000 description 1
- UBTPNKXHYILGJU-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC(C(F)(F)F)=C1 UBTPNKXHYILGJU-UHFFFAOYSA-N 0.000 description 1
- BULGSEUYSPGOCC-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]butan-1-one Chemical compound CCCC(=O)C1=CC=C(C(F)(F)F)C=C1 BULGSEUYSPGOCC-UHFFFAOYSA-N 0.000 description 1
- HHAISVSEJFEWBZ-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(C(F)(F)F)C=C1 HHAISVSEJFEWBZ-UHFFFAOYSA-N 0.000 description 1
- YCECQFKWCCEISA-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]pentan-1-one Chemical compound CCCCC(=O)C1=CC=C(C(F)(F)F)C=C1 YCECQFKWCCEISA-UHFFFAOYSA-N 0.000 description 1
- QFKOWENRSZZLPK-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=C(C(F)(F)F)C=C1 QFKOWENRSZZLPK-UHFFFAOYSA-N 0.000 description 1
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
- YTCGOUNVIAWCMG-UHFFFAOYSA-N 1-chloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Cl)=C1 YTCGOUNVIAWCMG-UHFFFAOYSA-N 0.000 description 1
- PSABUFWDVWCFDP-UHFFFAOYSA-N 2,2-dimethylheptane Chemical compound CCCCCC(C)(C)C PSABUFWDVWCFDP-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- JPKKMFOXWKNEEN-UHFFFAOYSA-N 2-methylcholine Chemical compound CC(O)C[N+](C)(C)C JPKKMFOXWKNEEN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WXMPHCXJKNKNBX-UHFFFAOYSA-N CC(OCc1cc(C(F)(F)F)ccc1)=O Chemical compound CC(OCc1cc(C(F)(F)F)ccc1)=O WXMPHCXJKNKNBX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GSBKRFGXEJLVMI-UHFFFAOYSA-N Nervonyl carnitine Chemical compound CCC[N+](C)(C)C GSBKRFGXEJLVMI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- XNTQTOLGQFJZMO-UHFFFAOYSA-N benzyl(trimethyl)phosphanium Chemical group C[P+](C)(C)CC1=CC=CC=C1 XNTQTOLGQFJZMO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- ZJHQDSMOYNLVLX-UHFFFAOYSA-N diethyl(dimethyl)azanium Chemical compound CC[N+](C)(C)CC ZJHQDSMOYNLVLX-UHFFFAOYSA-N 0.000 description 1
- RBECNRCKEQGFRU-UHFFFAOYSA-N diethyl(dimethyl)phosphanium Chemical group CC[P+](C)(C)CC RBECNRCKEQGFRU-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical compound C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- IQLVJVXTKNBZRC-UHFFFAOYSA-N ethyl(trimethyl)phosphanium Chemical group CC[P+](C)(C)C IQLVJVXTKNBZRC-UHFFFAOYSA-N 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical class [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- VCAVAURZPNANDQ-UHFFFAOYSA-N ethyl-hexadecyl-dimethylazanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC VCAVAURZPNANDQ-UHFFFAOYSA-N 0.000 description 1
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- AHCKRTXGDNIJSK-UHFFFAOYSA-N methyl(trioctyl)phosphanium Chemical group CCCCCCCC[P+](C)(CCCCCCCC)CCCCCCCC AHCKRTXGDNIJSK-UHFFFAOYSA-N 0.000 description 1
- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
- UARUINOVQHEYKN-UHFFFAOYSA-M methyl(tripropyl)azanium;iodide Chemical compound [I-].CCC[N+](C)(CCC)CCC UARUINOVQHEYKN-UHFFFAOYSA-M 0.000 description 1
- PLNPRGLZZXAKGE-UHFFFAOYSA-N methyl(tripropyl)phosphanium Chemical group CCC[P+](C)(CCC)CCC PLNPRGLZZXAKGE-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- HTKPDYSCAPSXIR-UHFFFAOYSA-N octyltrimethylammonium ion Chemical compound CCCCCCCC[N+](C)(C)C HTKPDYSCAPSXIR-UHFFFAOYSA-N 0.000 description 1
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical group CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical group C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- XOGCTUKDUDAZKA-UHFFFAOYSA-N tetrapropylphosphanium Chemical compound CCC[P+](CCC)(CCC)CCC XOGCTUKDUDAZKA-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
- XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical group CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- TZWFFXFQARPFJN-UHFFFAOYSA-N triethyl(methyl)phosphanium Chemical group CC[P+](C)(CC)CC TZWFFXFQARPFJN-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- IKANSXQHJXBNIN-UHFFFAOYSA-N trimethyl(octadecyl)phosphanium Chemical compound CCCCCCCCCCCCCCCCCC[P+](C)(C)C IKANSXQHJXBNIN-UHFFFAOYSA-N 0.000 description 1
- NVQBNLRCSAEYHZ-UHFFFAOYSA-N trimethyl(octyl)phosphanium Chemical compound CCCCCCCC[P+](C)(C)C NVQBNLRCSAEYHZ-UHFFFAOYSA-N 0.000 description 1
- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical compound C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明の高純度トリフルオロメチル基置換芳香族ケトンの製造方法は、下記一般式(1)で示されるハロゲン置換ベンゾトリフルオライド化合物を出発基質とする。
検出器 : FID
カラム :TC−17,0.32mmφ×60m,0.25μm(J&W社製)
カラム温度:50℃(3.0分保持)→(10℃/分)→250℃(3.0分保持)
注入口温度:250℃
検出器温度:250℃
全流量 :62.6mL/分 (He 141.9kPa)
スプリット比:1/20
サンプル注入量:1.0μL
2. サンプル
10mlメスフラスコにサンプル0.2gを、電子上皿天秤を使用し秤量する。これにアセトンを加え、メスアップした溶液をサンプル溶液とした。
テトラヒドロフラン75.0g(1.04mol;nacalai tesque社製)、マグネシウム粉末5.1g(0.208mol;中央工産社製)、LiCl 2.5g(0.08mol;nacalai tesque社製)を温度計付き四つ口フラスコ(容量200ml)に投入し、系内を窒素置換しながら、撹拌した。これに1mol/LエチルマグネシウムブロミドTHF溶液0.5g(東京化成社製)を添加し、系内の水分を除去した。続いて、臭化エチル 0.44g(0.004mol;和光純薬社製)を加えた。暫く撹拌し、発熱が起こることを確認した。次に反応液温度45〜50℃に保ちながら、o−クロロベンゾトリフルオライド36.1g(0.2mol;和光純薬社製)を徐々に滴下した。滴下終了後、45℃で5時間撹拌しながら、熟成した。熟成後、トルエン 10.8gを加えて、希釈し、グリニャール試薬溶液を得た。
実施例1において、無水酢酸19.8g(0.19mol)を無水プロピオン酸25.2g(0.19mol;和光純薬社製)に変更した以外は、実施例1と同様に反応を行った。塩基性条件下での加水分解処理を行った後、油相に含まれる不純物プロピオン酸クロロブチルエステルおよびプロピオン酸トリフルオロメチルフェニルエステルの含有量は、含まれる2’−トリフルオロメチルプロピオフェノンに対して、それぞれ0.2%、0.1%であった。
実施例1において、塩基性条件下での加水分解処理を行わず、油相を取得した。この油相に含まれる不純物 酢酸クロロブチルエステルおよび酢酸トリフルオロメチルフェニルエステルの含有量は、含まれる2’−トリフルオロメチルアセトフェノンに対して、それぞれ2.5%、1.2%であった。これを減圧蒸留(減圧度0.4〜1.3kPa、留出温度95〜100℃)した結果、トータル収率62.5%(原料o−クロロベンゾトリフルオライド基準)で、GC純度97.2%の2’-トリフルオロメチルアセトフェノンを得た。不純物として、酢酸クロロブチルエステル 1.2%および酢酸トリフルオロメチルフェニルエステルの含有量は、0.7%であった。
実施例2において、塩基性条件下での加水分解処理を行わず、油相を取得した。この油相に含まれる不純物 プロピオン酸クロロブチルエステルおよびプロピオン酸トリフルオロメチルフェニルエステルの含有量は、含まれる2’−トリフルオロメチルプロピオフェノンに対して、それぞれ3.1%、1.4%であった。これを減圧蒸留(減圧度0.4〜1.3kPa、留出温度105〜110℃)した結果、トータル収率68.2%(原料o−クロロベンゾトリフルオライド基準)で、GC純度96.8%の2’−トリフルオロメチルプロピオフェノンを得た。不純物として、プロピオン酸クロロブチルエステル 1.5%およびプロピオン酸トリフルオロメチルフェニルエステルの含有量は、0.9%であった。
実施例1において、テトラn−ブチルアンモニウムプロミドを入れずに加水分解処理を行った以外、実施例1と同様に反応を行った。油相に含まれる不純物 酢酸クロロブチルエステルおよび酢酸トリフルオロメチルフェニルエステルの含有量は、含まれる2’−トリフルオロメチルアセトフェノンに対して、それぞれ0.5%、0.3%であった。さらに加水分解処理時間を延長し、10時間行ったところ、それぞれ0.3%、0.2%となった。
実施例2において、テトラn−ブチルアンモニウムプロミドを入れずに加水分解処理を行った以外、実施例2と同様に反応を行った。油相に含まれる不純物 プロピオン酸クロロブチルエステルおよびプロピオン酸トリフルオロメチルフェニルエステルの含有量は、含まれる2’−トリフルオロメチルプロピオフェノンに対して、それぞれ0.4%、0.2%であった。さらに加水分解処理時間を延長し、10時間行ったところ、それぞれ0.3%、0.1%となった。
Claims (5)
- 前記塩基を含む水溶液を用いて、塩基性条件下で加水分解する際、相関移動触媒を共存させる請求項1に記載の高純度トリフルオロメチル基置換芳香族ケトンの製造方法。
- 酸無水物が、無水酢酸、無水プロピオン酸または無水酪酸である請求項1または2記載の高純度トリフルオロメチル基置換芳香族ケトンの製造方法。
- トリフルオロメチル基置換芳香族ケトンが、トリフルオロメチルアセトフェノン、トリフルオロメチルプロピオフェノン、または、トリフルオロメチルブチロフェノンである請求項1から3のいずれか記載の高純度トリフルオロメチル基置換芳香族ケトンの製造方法。
- 塩基を含む水溶液を用いて加水分解処理する際に、処理温度40〜100℃で実施する請求項1〜4のいずれか記載の高純度トリフルオロメチル基置換芳香族ケトンの製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017197648A JP6830051B2 (ja) | 2017-10-11 | 2017-10-11 | 高純度トリフルオロメチル基置換芳香族ケトンの製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017197648A JP6830051B2 (ja) | 2017-10-11 | 2017-10-11 | 高純度トリフルオロメチル基置換芳香族ケトンの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019069922A true JP2019069922A (ja) | 2019-05-09 |
JP6830051B2 JP6830051B2 (ja) | 2021-02-17 |
Family
ID=66440630
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017197648A Active JP6830051B2 (ja) | 2017-10-11 | 2017-10-11 | 高純度トリフルオロメチル基置換芳香族ケトンの製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6830051B2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11840507B2 (en) | 2020-08-19 | 2023-12-12 | Arxada Ag | Process for the preparation of phenyl ketones |
CN117222615A (zh) * | 2020-08-19 | 2023-12-12 | 阿尔萨达股份公司 | 用于制备苯基酮的方法 |
-
2017
- 2017-10-11 JP JP2017197648A patent/JP6830051B2/ja active Active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11840507B2 (en) | 2020-08-19 | 2023-12-12 | Arxada Ag | Process for the preparation of phenyl ketones |
CN117222615A (zh) * | 2020-08-19 | 2023-12-12 | 阿尔萨达股份公司 | 用于制备苯基酮的方法 |
JP7441378B2 (ja) | 2020-08-19 | 2024-02-29 | アークサーダ・アー・ゲー | フェニルケトンの調製方法 |
Also Published As
Publication number | Publication date |
---|---|
JP6830051B2 (ja) | 2021-02-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2019069922A (ja) | 高純度トリフルオロメチル基置換芳香族ケトンの製造方法 | |
JP6086163B2 (ja) | 2’−トリフルオロメチル基置換芳香族ケトンの製造方法 | |
CN102757455B (zh) | 环丙基硼酸的制备方法 | |
JP5211876B2 (ja) | 高純度2’−トリフルオロメチルプロピオフェノンの製造方法 | |
WO1994024086A1 (en) | Process for producing 2-fluoroisobutyric acid or ester thereof | |
CN109485541B (zh) | 一种制备1h,1h,2h-全氟-1-辛烯的方法 | |
JP2018043956A (ja) | β−アルコキシプロピオン酸エステルの製造方法 | |
CN104447230B (zh) | 一种4-甲氧基苯乙烯的制备方法 | |
CN108863717B (zh) | 一种高效地制备炔醇的方法 | |
CN111072455B (zh) | 一种微反应器连续制备五氟苯酚的方法 | |
JP6225788B2 (ja) | 1,1,1,5,5,5−ヘキサフルオロアセチルアセトンの製造方法 | |
CN106046046A (zh) | 一种三(三甲基硅烷基)亚磷酸酯的制备方法 | |
JP2019104702A (ja) | 3’−トリフルオロメチル基置換芳香族ケトンの製造方法 | |
JP2021054745A (ja) | 2′,3′−ジメチル芳香族ケトンの製造方法 | |
JP2001322955A (ja) | 2−ブロモ−3,3,3−トリフルオロプロペンの製造方法 | |
JP2016069299A (ja) | 2−トリフルオロメチル安息香酸エステルの製造方法 | |
US11066422B2 (en) | Method of producing cycloalkyl(trifluoromethyl)benzene | |
JP2010001222A (ja) | アルコール類の製造方法 | |
JP6753193B2 (ja) | 2−ヒドロキシ−2−メチル−1−プロピル(メタ)アクリレートおよび/または3−ヒドロキシ−3−メチル−1−ブチル(メタ)アクリレートの製造方法、ならびに、精製方法および組成物 | |
JP4281258B2 (ja) | 2−ブチルオクタン二酸の製造法 | |
JP6194353B2 (ja) | ラバンジュラールの製造方法 | |
JP6341040B2 (ja) | 1,1,1,5,5,5−ヘキサフルオロアセチルアセトンの製造方法 | |
WO2002051798A1 (en) | PROCESS FOR PRODUCING β-KETONITRILE COMPOUND | |
KR20220092200A (ko) | 부산물 생성을 억제하는 크레졸의 제조 방법 | |
WO2011152501A1 (ja) | 長鎖飽和脂肪族一級アルコールの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190722 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200611 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200630 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200819 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210112 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210125 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6830051 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |