JPS6334858B2 - - Google Patents
Info
- Publication number
- JPS6334858B2 JPS6334858B2 JP55096306A JP9630680A JPS6334858B2 JP S6334858 B2 JPS6334858 B2 JP S6334858B2 JP 55096306 A JP55096306 A JP 55096306A JP 9630680 A JP9630680 A JP 9630680A JP S6334858 B2 JPS6334858 B2 JP S6334858B2
- Authority
- JP
- Japan
- Prior art keywords
- fluoride
- process according
- carried out
- reaction
- bromination
- 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.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 claims description 64
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 35
- 239000011698 potassium fluoride Substances 0.000 claims description 24
- 235000003270 potassium fluoride Nutrition 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 18
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- 230000031709 bromination Effects 0.000 claims description 16
- 238000005893 bromination reaction Methods 0.000 claims description 16
- LVZPKYYPPLUECL-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1 LVZPKYYPPLUECL-UHFFFAOYSA-N 0.000 claims description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 229910052742 iron Inorganic materials 0.000 claims description 11
- AIOKJVVAYNKWQP-UHFFFAOYSA-N 3-bromo-4-fluorobenzoyl fluoride Chemical compound FC(=O)C1=CC=C(F)C(Br)=C1 AIOKJVVAYNKWQP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002506 iron compounds Chemical group 0.000 claims description 10
- 239000011775 sodium fluoride Substances 0.000 claims description 9
- 235000013024 sodium fluoride Nutrition 0.000 claims description 9
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 9
- 150000001491 aromatic compounds Chemical class 0.000 claims description 7
- -1 Compound 4-fluoro-3-bromo-benzoyl fluoride Chemical class 0.000 claims description 6
- 239000012025 fluorinating agent Substances 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 230000001737 promoting effect Effects 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 2
- 238000003682 fluorination reaction Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 9
- ONELILMJNOWXSA-UHFFFAOYSA-N 3-bromo-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(Br)=C1 ONELILMJNOWXSA-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- CHOSHMAFWKKQQF-UHFFFAOYSA-N 3-bromo-4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Br)=C1 CHOSHMAFWKKQQF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- MFHPYLFZSCSNST-UHFFFAOYSA-N 1-chloro-2-(trichloromethyl)benzene Chemical compound ClC1=CC=CC=C1C(Cl)(Cl)Cl MFHPYLFZSCSNST-UHFFFAOYSA-N 0.000 description 2
- QLRKALMVPCQTMU-UHFFFAOYSA-N 2-bromo-1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C(Br)=C1 QLRKALMVPCQTMU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- FYIOXXUKFQPTJS-UHFFFAOYSA-N 2-(4-fluoro-3-phenoxyphenyl)-2-hydroxyacetonitrile Chemical compound N#CC(O)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 FYIOXXUKFQPTJS-UHFFFAOYSA-N 0.000 description 1
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical class CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- VLXNXMTVRWIUJZ-UHFFFAOYSA-N 4-Fluoro-3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 VLXNXMTVRWIUJZ-UHFFFAOYSA-N 0.000 description 1
- GIQURHRJQIPDKM-UHFFFAOYSA-N 4-fluorobenzoyl fluoride Chemical compound FC(=O)C1=CC=C(F)C=C1 GIQURHRJQIPDKM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- GGCCAAZVCUPTEE-UHFFFAOYSA-N S=[I] Chemical class S=[I] GGCCAAZVCUPTEE-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical class FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GSQACUNMFGRAKY-UHFFFAOYSA-N bromine;1,4-dioxane Chemical compound [Br].C1COCCO1 GSQACUNMFGRAKY-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/70—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
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
ãçºæã®è©³çŽ°ãªèª¬æã
æ¬çºæã¯ãæçš®ã®çœ®æãã³ãŸã€ã«ãã«ãªãªãã
ã³ãã®è£œæ³ã«é¢ããã
ã³ãã®è£œæ³ã«é¢ããã
æ¬çºæã¯æ°èŠååç©ãšããŠïŒâãã«ãªãâïŒâ
ããã¢âãã³ãŸã€ã«ãã«ãªãªããæäŸããã
ããã¢âãã³ãŸã€ã«ãã«ãªãªããæäŸããã
æ¬çºæã¯ãŸããïŒâãã«ãªãâïŒâããã¢âã
ã³ãŸã€ã«ãã«ãªãªãã®è£œæ³ã«ãããŠãæåã«ïœâ
ã¯ããâãã³ãŸããªã¯ããªããèçŽ åãã次ã«ã
ãªã¯ããã¡ãã«åºãéšåå æ°Žå解ããçããäžé
äœãåŒçŽ åå€ãšåå¿ãããããšãç¹åŸŽãšãã補æ³
ããæäŸããã
ã³ãŸã€ã«ãã«ãªãªãã®è£œæ³ã«ãããŠãæåã«ïœâ
ã¯ããâãã³ãŸããªã¯ããªããèçŽ åãã次ã«ã
ãªã¯ããã¡ãã«åºãéšåå æ°Žå解ããçããäžé
äœãåŒçŽ åå€ãšåå¿ãããããšãç¹åŸŽãšãã補æ³
ããæäŸããã
èçŽ åã¯äŸãã°åäœèçŽ ãèçŽ äŸäžååç©äŸã
ã°èåã¹ã«ããªã«ãŸãã¯èåæ²çŽ ããŸãã¯èçŽ å«
æé¯äœäŸãã°ãžãªããµã³âèçŽ ãçšããŠå®æœãã
åŸãã
ã°èåã¹ã«ããªã«ãŸãã¯èåæ²çŽ ããŸãã¯èçŽ å«
æé¯äœäŸãã°ãžãªããµã³âèçŽ ãçšããŠå®æœãã
åŸãã
æ¬çºæã®è£œæ³ã«ãããŠã¯ã奜é©ã«ã¯ïœâã¯ãã
âãã³ãŸããªã¯ããªãã第ïŒåå¿æ®µéã«ãããŠå
äœèçŽ ãšåå¿ããããäžå®å šåå¿ã«ããåçæ倱
ãé²ãããã«ãå°ãªããšãçã¢ã«éã®èçŽ ãå¿ èŠ
ã§ããããããã奜é©ã«ã¯å°éå°éã«ãŠçšããã
ããäŸãã°ïœâã¯ããâãã³ãŸããªã¯ããªãïŒã¢
ã«åœãïŒâ1.2ã奜é©ã«ã¯1.03â1.15ã¢ã«ã®èçŽ ã
çšãåŸãã
âãã³ãŸããªã¯ããªãã第ïŒåå¿æ®µéã«ãããŠå
äœèçŽ ãšåå¿ããããäžå®å šåå¿ã«ããåçæ倱
ãé²ãããã«ãå°ãªããšãçã¢ã«éã®èçŽ ãå¿ èŠ
ã§ããããããã奜é©ã«ã¯å°éå°éã«ãŠçšããã
ããäŸãã°ïœâã¯ããâãã³ãŸããªã¯ããªãïŒã¢
ã«åœãïŒâ1.2ã奜é©ã«ã¯1.03â1.15ã¢ã«ã®èçŽ ã
çšãåŸãã
åäœèçŽ ãçšããèçŽ åã¯ãå
šè¬ã«è³éŠæåå
ç©ã®æ žã®èçŽ åãä¿é²ããç©è³ªã®ååšäžã«å®æœã
ãããæ¯ãã®åŠãç©è³ªãšããŠã¯ãã¢ã«ãããŠã ã
éããã¿ã³ãäºéããã³ã¢ã³ãã¢ã³ã®ãã©ã€ãã
äŸãã°ã¯ããªãããããããŸãã¯ãšãŒãžãããã
ã³ç¡«åéããã³æ²çŽ ãæãããããåèšã®å çŽ ã®
ãã©ã€ããšããŠãããããçšããã¹ãå Žåã«ã¯ã
該å çŽ ãåäœåœ¢æ ã«ãŠåå¿æ··åç©ã«æ·»å ãããšå
åã§ããïŒãããã¯åäœèçŽ ãšã®åå¿ã«ãã€ãŠæ··
åç©äžã«ããããã圢æãããè³éŠæååç©ã®æ ž
ã®èçŽ åãä¿é²ããåã ã®ç©è³ªã®äŸãšããŠã¯æ¬¡ã®
ãã®ãæããããïŒå¡©åã¢ã«ãããŠã ãèåã¢ã«
ãããŠã ãéïŒïŒã¯ããªããéïŒïŒããã
ããåå¡©åãã¿ã³ãåèåãã¿ã³ãå¡©åäºéãè
åäºéãã¢ã³ãã¢ã³ïŒïŒã¯ããªããã¢ã³ãã¢ã³
ïŒïŒãããããç¡«åéããã³æ²çŽ ãéïŒïŒã¯
ããªããéïŒïŒãããããŸãã¯ç¡«åéã®åŠãé
ååç©ã奜é©ã«çšãããããç¡«åéãç¹ã«å¥œé©ã«
çšãããããè³éŠæååç©ã®æ žã®èçŽ åãä¿é²ã
ãããã®åèšã®ç©è³ªã¯ãåºçºææã®éã«å¯ŸããŠäŸ
ãã°0.01âïŒééïŒ ã奜é©ã«ã¯0.1âïŒééïŒ ã®
éã«ãŠåå¿æ··åç©ã«æ·»å ãããã
ç©ã®æ žã®èçŽ åãä¿é²ããç©è³ªã®ååšäžã«å®æœã
ãããæ¯ãã®åŠãç©è³ªãšããŠã¯ãã¢ã«ãããŠã ã
éããã¿ã³ãäºéããã³ã¢ã³ãã¢ã³ã®ãã©ã€ãã
äŸãã°ã¯ããªãããããããŸãã¯ãšãŒãžãããã
ã³ç¡«åéããã³æ²çŽ ãæãããããåèšã®å çŽ ã®
ãã©ã€ããšããŠãããããçšããã¹ãå Žåã«ã¯ã
該å çŽ ãåäœåœ¢æ ã«ãŠåå¿æ··åç©ã«æ·»å ãããšå
åã§ããïŒãããã¯åäœèçŽ ãšã®åå¿ã«ãã€ãŠæ··
åç©äžã«ããããã圢æãããè³éŠæååç©ã®æ ž
ã®èçŽ åãä¿é²ããåã ã®ç©è³ªã®äŸãšããŠã¯æ¬¡ã®
ãã®ãæããããïŒå¡©åã¢ã«ãããŠã ãèåã¢ã«
ãããŠã ãéïŒïŒã¯ããªããéïŒïŒããã
ããåå¡©åãã¿ã³ãåèåãã¿ã³ãå¡©åäºéãè
åäºéãã¢ã³ãã¢ã³ïŒïŒã¯ããªããã¢ã³ãã¢ã³
ïŒïŒãããããç¡«åéããã³æ²çŽ ãéïŒïŒã¯
ããªããéïŒïŒãããããŸãã¯ç¡«åéã®åŠãé
ååç©ã奜é©ã«çšãããããç¡«åéãç¹ã«å¥œé©ã«
çšãããããè³éŠæååç©ã®æ žã®èçŽ åãä¿é²ã
ãããã®åèšã®ç©è³ªã¯ãåºçºææã®éã«å¯ŸããŠäŸ
ãã°0.01âïŒééïŒ ã奜é©ã«ã¯0.1âïŒééïŒ ã®
éã«ãŠåå¿æ··åç©ã«æ·»å ãããã
æ¬çºæã®è£œæ³ã«ãããèçŽ åã¯ãç¡æº¶å€ã«ãŠå®
æœããåŸããããããäžæŽ»æ§æº¶å€äžã«ãŠå®æœãã
ããšãå¯èœã§ãããäžæŽ»æ§æº¶å€ã®äŸãšããŠã¯ãã
ãã²ã³åçåæ°ŽçŽ ãäŸãã°ã¡ãã¬ã³ã¯ããªããã¯
ãããã«ã ãïŒïŒïŒâãžã¯ãããšã¿ã³ããŸãã¯ã
ãªã¯ãããšãã¬ã³ãæãåŸãã
æœããåŸããããããäžæŽ»æ§æº¶å€äžã«ãŠå®æœãã
ããšãå¯èœã§ãããäžæŽ»æ§æº¶å€ã®äŸãšããŠã¯ãã
ãã²ã³åçåæ°ŽçŽ ãäŸãã°ã¡ãã¬ã³ã¯ããªããã¯
ãããã«ã ãïŒïŒïŒâãžã¯ãããšã¿ã³ããŸãã¯ã
ãªã¯ãããšãã¬ã³ãæãåŸãã
èçŽ åã¯å
šè¬ã«ãããã«é«ãããã枩床ã«ãŠå®
æœããããïŒäŸãšããŠã20ãâ70âã奜é©ã«ã¯30ã
â60âã®æž©åºŠãæãåŸãã
æœããããïŒäŸãšããŠã20ãâ70âã奜é©ã«ã¯30ã
â60âã®æž©åºŠãæãåŸãã
æ¬çºæã®è£œæ³ã®ç¬¬ïŒåå¿æ®µéã¯ãç¡æº¶å€äžã«ãŸ
ãã¯æº¶å€ãçšããŠå®æœãåŸãã溶å€ãçšããæé
ã®ããã«ã¯äžæŽ»æ§æº¶å€ãæãåŸãããããã®äŸãš
ããŠã¯ãæ¬çºæã®è£œæ³ã®ç¬¬ïŒåå¿æ®µéã«ã€ããŠæ¢
ã«æããããããã²ã³åçåæ°ŽçŽ äŸãã°ã¡ãã¬ã³
ã¯ããªããã¯ãããã«ã ãïŒïŒïŒâãžã¯ãããšã¿
ã³ãããªã¯ãããšãã¬ã³ãŸãã¯ã¯ãããã³ãŒã³ã
æããããã
ãã¯æº¶å€ãçšããŠå®æœãåŸãã溶å€ãçšããæé
ã®ããã«ã¯äžæŽ»æ§æº¶å€ãæãåŸãããããã®äŸãš
ããŠã¯ãæ¬çºæã®è£œæ³ã®ç¬¬ïŒåå¿æ®µéã«ã€ããŠæ¢
ã«æããããããã²ã³åçåæ°ŽçŽ äŸãã°ã¡ãã¬ã³
ã¯ããªããã¯ãããã«ã ãïŒïŒïŒâãžã¯ãããšã¿
ã³ãããªã¯ãããšãã¬ã³ãŸãã¯ã¯ãããã³ãŒã³ã
æããããã
ããªã¯ããã¡ãã«åºã®éšåå æ°Žå解ã¯ãå
šè¬ã«
第ïŒåå¿æ®µéã«ãŠæ°Žãæ·»å ããããšã«ãã€ãŠå®æœ
ããããæ°Žã¯äŸãã°ãã®ãŸãŸã®åœ¢ã«ãŠããŸãã¯é ž
ãå¡©ã®æ°Žæº¶æ¶²ã®åœ¢ã«ãŠæ·»å ããåŸããæ°Žããã®ãŸ
ãŸã®åœ¢ã«ãŠæ·»å ããã®ã奜ãŸããã
第ïŒåå¿æ®µéã«ãŠæ°Žãæ·»å ããããšã«ãã€ãŠå®æœ
ããããæ°Žã¯äŸãã°ãã®ãŸãŸã®åœ¢ã«ãŠããŸãã¯é ž
ãå¡©ã®æ°Žæº¶æ¶²ã®åœ¢ã«ãŠæ·»å ããåŸããæ°Žããã®ãŸ
ãŸã®åœ¢ã«ãŠæ·»å ããã®ã奜ãŸããã
å
šè¬ã«æ¬çºæã®è£œæ³ã®ç¬¬ïŒåå¿æ®µéã¯ãŸããè³
éŠæçã«çµåããããããããªã¯ããã¡ãã«åºã®
éšåå æ°Žå解ãä¿é²ããç©è³ªã®ååšäžã«ãŠãå®æœ
ãããããã®ç®çã®ããã«ã第ïŒåå¿æ®µéã«ãã
ãŠæ žã®èçŽ åãä¿é²ããããã«çšãããåŸãã®ãš
åãç©è³ªãçšãåŸããåèšã®ç©è³ªã®ãã¡ã第ïŒå
å¿æ®µéã®ããã«éååç©ã奜é©ã«çšãããããé
ããã²ã³åç©äŸãã°éïŒïŒã¯ããªããŸãã¯é
ïŒïŒãããããç¹ã«å¥œãŸãããè³éŠæçã«çµå
ããããããããªã¯ããã¡ãã«åºã®éšåå æ°Žå解
ãä¿é²ããããã®ç©è³ªã¯ãäŸãã°çšããããïœâ
ã¯ããâãã³ãŸããªã¯ããªãã«å¯ŸããŠ0.01âïŒé
éïŒ ã奜é©ã«ã¯0.1âïŒééïŒ ã®éã«ãŠçšããã
åŸãã
éŠæçã«çµåããããããããªã¯ããã¡ãã«åºã®
éšåå æ°Žå解ãä¿é²ããç©è³ªã®ååšäžã«ãŠãå®æœ
ãããããã®ç®çã®ããã«ã第ïŒåå¿æ®µéã«ãã
ãŠæ žã®èçŽ åãä¿é²ããããã«çšãããåŸãã®ãš
åãç©è³ªãçšãåŸããåèšã®ç©è³ªã®ãã¡ã第ïŒå
å¿æ®µéã®ããã«éååç©ã奜é©ã«çšãããããé
ããã²ã³åç©äŸãã°éïŒïŒã¯ããªããŸãã¯é
ïŒïŒãããããç¹ã«å¥œãŸãããè³éŠæçã«çµå
ããããããããªã¯ããã¡ãã«åºã®éšåå æ°Žå解
ãä¿é²ããããã®ç©è³ªã¯ãäŸãã°çšããããïœâ
ã¯ããâãã³ãŸããªã¯ããªãã«å¯ŸããŠ0.01âïŒé
éïŒ ã奜é©ã«ã¯0.1âïŒééïŒ ã®éã«ãŠçšããã
åŸãã
第ïŒåå¿æ®µéã«ãããéšåå æ°Žå解ã®ããã«å¿
èŠãªæ°Žã¯ãå šè¬ã«çºç±åå¿ãå¶åŸ¡äžã«ä¿ã¡åŸãã
ããªå·¥åã«åå¿æ··åç©ã«èšéæ·»å ããããæ¬çºæ
ã®è£œæ³ã«ãããŠå®å šåå¿ãéæããããã«ã¯ãåº
çºææã«å¯ŸããŠçã¢ã«éã®æ°Žãå¿ èŠã§ãããçã¢
ã«éããå°éã®æ°Žãçšãããšãäžå®å šåå¿ãšãªã
åçæ倱ãçãããåŸã€ãŠã第ïŒåå¿æ®µéã«ãã
ãŠåå¿ãå®çµãããããã«ã¯ã䜿çšåºçºææã«å¯Ÿ
ããŠçã¢ã«éãã幟åå€éã®æ°Žãéåžžçšããã
ããäŸãã°åºçºååç©ïŒã¢ã«åœãïŒâ1.2ã¢ã«ã
奜é©ã«ã¯1.05â1.15ã¢ã«ã®æ°ŽãçšãåŸãã
èŠãªæ°Žã¯ãå šè¬ã«çºç±åå¿ãå¶åŸ¡äžã«ä¿ã¡åŸãã
ããªå·¥åã«åå¿æ··åç©ã«èšéæ·»å ããããæ¬çºæ
ã®è£œæ³ã«ãããŠå®å šåå¿ãéæããããã«ã¯ãåº
çºææã«å¯ŸããŠçã¢ã«éã®æ°Žãå¿ èŠã§ãããçã¢
ã«éããå°éã®æ°Žãçšãããšãäžå®å šåå¿ãšãªã
åçæ倱ãçãããåŸã€ãŠã第ïŒåå¿æ®µéã«ãã
ãŠåå¿ãå®çµãããããã«ã¯ã䜿çšåºçºææã«å¯Ÿ
ããŠçã¢ã«éãã幟åå€éã®æ°Žãéåžžçšããã
ããäŸãã°åºçºååç©ïŒã¢ã«åœãïŒâ1.2ã¢ã«ã
奜é©ã«ã¯1.05â1.15ã¢ã«ã®æ°ŽãçšãåŸãã
ããããçã¢ã«éããéå°ã®éã«ãŠåå¿æ··åç©
äžã«ååšããæ°Žã¯ãæãŸãããªãå¯åå¿ãããã
ããåå¿ã®ããã«äžå¿ èŠãªéå°éã®æ°Žã¯ããã®ç®
çã®ããã«æ·»å ãããããªãã«ã¯ããªããšã®åå¿
ã«ãã€ãŠé€å»ããåŸããåæã«ãéå°éã®æ°Žãšå
å¿ããŠæãŸãããªãå¯çç©ãçãããããªåå¿æ··
åç©äžã®æåããããªãã«ã¯ããªããšåå¿ãã
ãŠãæ¬çºæã«åŸãæ¹æ³ã«ãã€ãŠèçŽ åãããããŠ
ããªã¯ããã¡ãã«åºãéšåå æ°Žå解ãããïœâã¯
ããâãã³ãŸããªã¯ããªããçããããšãå¯èœã§
ããã
äžã«ååšããæ°Žã¯ãæãŸãããªãå¯åå¿ãããã
ããåå¿ã®ããã«äžå¿ èŠãªéå°éã®æ°Žã¯ããã®ç®
çã®ããã«æ·»å ãããããªãã«ã¯ããªããšã®åå¿
ã«ãã€ãŠé€å»ããåŸããåæã«ãéå°éã®æ°Žãšå
å¿ããŠæãŸãããªãå¯çç©ãçãããããªåå¿æ··
åç©äžã®æåããããªãã«ã¯ããªããšåå¿ãã
ãŠãæ¬çºæã«åŸãæ¹æ³ã«ãã€ãŠèçŽ åãããããŠ
ããªã¯ããã¡ãã«åºãéšåå æ°Žå解ãããïœâã¯
ããâãã³ãŸããªã¯ããªããçããããšãå¯èœã§
ããã
éšåå æ°Žå解ã®ããã®æž©åºŠã®äŸãšããŠã¯20â
100âã奜é©ã«ã¯50â85âãæãåŸããå æ°Žå解
åå¿ãä¿é²ããããã«ã¯ãæåã«åå¿æ··åç©ã幟
åå ç±ãã次ã«æ°Žæ·»å é床ã«ããããã³ïŒãŸãã¯
åå¿æ··åç©ãå·åŽããããšã«ãã€ãŠãçºç±åå¿ã
ææ枩床ç¯å²å ã«ä¿ã€ããšãåŸçã§ããåŸãã
100âã奜é©ã«ã¯50â85âãæãåŸããå æ°Žå解
åå¿ãä¿é²ããããã«ã¯ãæåã«åå¿æ··åç©ã幟
åå ç±ãã次ã«æ°Žæ·»å é床ã«ããããã³ïŒãŸãã¯
åå¿æ··åç©ãå·åŽããããšã«ãã€ãŠãçºç±åå¿ã
ææ枩床ç¯å²å ã«ä¿ã€ããšãåŸçã§ããåŸãã
æ¬çºæã®è£œæ³ã®ç¬¬ïŒåå¿æ®µéã«ãããŠã¯ã第ïŒ
段éããã®åå¿çæç©ãåŒçŽ åå€äŸãã°åŒåã«ãª
ãŠã ãŸãã¯åŒåã»ã·ãŠã ãåå¿ãããã奜é©ã«ã¯
åŒçŽ åå€ããŠåŒåã«ãªãŠã ãçšãããããåŒåã«
ãªãŠã ã®ïŒéšãåŒåãããªãŠã ã§çœ®æããé©åãª
ãã°å¥ã®åŒçŽ åå€ãšã®æ··åç©ãšããŠçšããããšã
å¯èœã§ããã
段éããã®åå¿çæç©ãåŒçŽ åå€äŸãã°åŒåã«ãª
ãŠã ãŸãã¯åŒåã»ã·ãŠã ãåå¿ãããã奜é©ã«ã¯
åŒçŽ åå€ããŠåŒåã«ãªãŠã ãçšãããããåŒåã«
ãªãŠã ã®ïŒéšãåŒåãããªãŠã ã§çœ®æããé©åãª
ãã°å¥ã®åŒçŽ åå€ãšã®æ··åç©ãšããŠçšããããšã
å¯èœã§ããã
æ¬çºæã®è£œæ³ã«ãããèçŽ åã«ã¯ãå
šè¬ã«åºçº
ææïŒã¢ã«åœãïŒã¢ã«ã®åŒåã«ãªãŠã ãå¿ èŠã§ã
ããåŒåã«ãªãŠã ãå°éçšãããšãäžå®å šåå¿ã®
çµæãšããŠåçæ倱ãçããããããã«ãåå¿ã
å®çµãããã«ã¯åŒåã«ãªãŠã ããããã«éå°éã«
ãŠçšããã®ãåŸçã§ããã倧éå°éã®åŒåã«ãªãŠ
ã ãçšããŠããæ¬çºæã®è£œæ³ã«æªåœ±é¿ã¯ç¡ããã
ãããçµæžæ§ã®ç¹ããé©åã§ã¯ãªãããããã«äŸ
ãã°äœ¿çšïœâã¯ããâãã³ãŸããªã¯ããªãïŒã¢ã«
åœãïŒâïŒã¢ã«ã奜é©ã«ã¯2.5â3.5ã¢ã«ã®åŒåã«
ãªãŠã ãçšãåŸãã
ææïŒã¢ã«åœãïŒã¢ã«ã®åŒåã«ãªãŠã ãå¿ èŠã§ã
ããåŒåã«ãªãŠã ãå°éçšãããšãäžå®å šåå¿ã®
çµæãšããŠåçæ倱ãçããããããã«ãåå¿ã
å®çµãããã«ã¯åŒåã«ãªãŠã ããããã«éå°éã«
ãŠçšããã®ãåŸçã§ããã倧éå°éã®åŒåã«ãªãŠ
ã ãçšããŠããæ¬çºæã®è£œæ³ã«æªåœ±é¿ã¯ç¡ããã
ãããçµæžæ§ã®ç¹ããé©åã§ã¯ãªãããããã«äŸ
ãã°äœ¿çšïœâã¯ããâãã³ãŸããªã¯ããªãïŒã¢ã«
åœãïŒâïŒã¢ã«ã奜é©ã«ã¯2.5â3.5ã¢ã«ã®åŒåã«
ãªãŠã ãçšãåŸãã
第ïŒåå¿æ®µéã®ããã®åå¿æ··åç©ã«ãåŒåã«ãª
ãŠã å šéãïŒåºŠã«æ·»å ãåŸããããããåŒåã«ãª
ãŠã ã幟ã€ãã«ãäŸãã°ïŒåã«åããŠæ·»å ããã
ãšãã§ããããã®å€åœ¢ã«ãããŠã¯ã第ïŒåå¿æ®µé
éå§åã«åŒåã«ãªãŠã ã®å¹Ÿéšåãã奜é©ã«ã¯å šé
ã®çŽååãåå¿æ··åç©ã«æ·»å ããæ®ãã第ïŒåå¿
段éäžã«ïŒåã«ãŸãã¯ãã以äžã®åã«åããŠæ·»å
ããã第ïŒåå¿æ®µéäžã«ä»»æçã«æ·»å ããããã®
æ®ãã®éã®åŒåã«ãªãŠã ã¯ãããã«è£å©å€ãçšã
ãã«ããŸãã¯å¥œé©ã«ã¯æžæ¿æ¶²ã®åœ¢ã«ãŠçšãããåŸ
ããé©åãªãã°ããã®ç¬¬ïŒåå¿æ®µéã®ããã«çšã
ããã溶å€ã®å¹Ÿéšåãããæžæ¿å€ãšããŠå©çšãåŸ
ãã
ãŠã å šéãïŒåºŠã«æ·»å ãåŸããããããåŒåã«ãª
ãŠã ã幟ã€ãã«ãäŸãã°ïŒåã«åããŠæ·»å ããã
ãšãã§ããããã®å€åœ¢ã«ãããŠã¯ã第ïŒåå¿æ®µé
éå§åã«åŒåã«ãªãŠã ã®å¹Ÿéšåãã奜é©ã«ã¯å šé
ã®çŽååãåå¿æ··åç©ã«æ·»å ããæ®ãã第ïŒåå¿
段éäžã«ïŒåã«ãŸãã¯ãã以äžã®åã«åããŠæ·»å
ããã第ïŒåå¿æ®µéäžã«ä»»æçã«æ·»å ããããã®
æ®ãã®éã®åŒåã«ãªãŠã ã¯ãããã«è£å©å€ãçšã
ãã«ããŸãã¯å¥œé©ã«ã¯æžæ¿æ¶²ã®åœ¢ã«ãŠçšãããåŸ
ããé©åãªãã°ããã®ç¬¬ïŒåå¿æ®µéã®ããã«çšã
ããã溶å€ã®å¹Ÿéšåãããæžæ¿å€ãšããŠå©çšãåŸ
ãã
第ïŒåå¿æ®µéã«ãããŠåŒåã«ãªãŠã ã幟ã€ãã®
éšåã«åããŠæ·»å ããå Žåã«ã¯ãæ·»å ãããã¹ã
åŒåã«ãªãŠã ã®å šéã®çŽ50ã¢ã«ïŒ ã®éãŸã§ã®åŒå
ã«ãªãŠã ã®ç¬¬ïŒéšåãŸãã¯è€æ°ã®ç¬¬ïŒéšåãåŒå
ãããªãŠã ã§çœ®ãæããããšãå¯èœã§ãããåŒå
ãããªãŠã ã¯åŒåã«ãªãŠã ãããå®äŸ¡ã§ããã
ãã第ïŒåå¿æ®µéã®ãã®å€æ³ã奜ãŸããã
éšåã«åããŠæ·»å ããå Žåã«ã¯ãæ·»å ãããã¹ã
åŒåã«ãªãŠã ã®å šéã®çŽ50ã¢ã«ïŒ ã®éãŸã§ã®åŒå
ã«ãªãŠã ã®ç¬¬ïŒéšåãŸãã¯è€æ°ã®ç¬¬ïŒéšåãåŒå
ãããªãŠã ã§çœ®ãæããããšãå¯èœã§ãããåŒå
ãããªãŠã ã¯åŒåã«ãªãŠã ãããå®äŸ¡ã§ããã
ãã第ïŒåå¿æ®µéã®ãã®å€æ³ã奜ãŸããã
第ïŒåå¿æ®µéã¯å
šè¬ã«äžæŽ»æ§ã®æ¥µæ§ããã³äžæ§
溶å€äžã«ãŠå®æœããããæ¯ãã®åŠã溶å€ã®äŸãšã
ãŠã¯ãããã©ã¡ãã¬ã³ã¹ã«ãã³ããžã¡ãã«ã¹ã«ã
ã³ããã³ïŒ®âã¡ãã«ãããªãã³ãæããããã奜
é©ã«ã¯ããã©ã¡ãã¬ã³ã¹ã«ãã³ã溶å€ãšããŠçšã
ãããã
溶å€äžã«ãŠå®æœããããæ¯ãã®åŠã溶å€ã®äŸãšã
ãŠã¯ãããã©ã¡ãã¬ã³ã¹ã«ãã³ããžã¡ãã«ã¹ã«ã
ã³ããã³ïŒ®âã¡ãã«ãããªãã³ãæããããã奜
é©ã«ã¯ããã©ã¡ãã¬ã³ã¹ã«ãã³ã溶å€ãšããŠçšã
ãããã
第ïŒåå¿æ®µéã¯å
šè¬ã«é«ãããã枩床ã«ãŠå®æœ
äŸããããïŒäŸãšããŠ160â220âã奜é©ã«ã¯180
â220âã®æž©åºŠãæãåŸãã
äŸããããïŒäŸãšããŠ160â220âã奜é©ã«ã¯180
â220âã®æž©åºŠãæãåŸãã
åã
ã®åå¿ã®åã
ãçµäºããæã«ããã®åã
ã®
åå¿æ®µéã®åå¿çæç©ã¯ãåœæ¥è ã«æ¢ç¥ã®é©åãª
æ¹æ³ã«ãããäŸãã°èžçãŸãã¯åçµæ¶ã«ãã€ãŠä»
äžããããããšãã§ãããããŠæ¬¡ã®åå¿æ®µéã«çš
ãããåŸããããããäžéäœãåé¢ããã«ãæå
ã®ïŒã€ã®åå¿æ®µéãé ã«å®æœããããšãã§ããã
æ¬çºæã®è£œæ³ã®ãã®å¥œé©ãªå€æ³ã«ãããŠã¯ã第ïŒ
åå¿æ®µéã®åå¿ãç¡æº¶å€ã«ãŠæåã«å®æœãããã
ã®åŸå³åº§ã«ç¬¬ïŒåå¿æ®µéãåãåå¿åšäžã§å®æœ
ãããã®åå¿ã®ããã«å¥œé©ã«ã¯ãåèšã®é©åãªæº¶
å€ã®ïŒã€ãæ·»å ããã第ïŒåå¿æ®µéã«ããããã®
奜é©ãªæº¶å€æ·»å ã¯ã第ïŒåå¿æ®µéã®çºç±åå¿ãå¶
埡ããã®ã«åŸçã§ãããåèšã®åŠãã第ïŒåå¿æ®µ
éã¯å¥œé©ã«ã¯éååç©ã®ååšäžã«å®æœããããå
èšã®éååç©ã®ïŒã€ã¯ç¬¬ïŒåå¿æ®µéãšåæ§ã«ç¬¬ïŒ
åå¿æ®µéã®ããã«ãé©åã§ããããã第ïŒåå¿æ®µ
éãæ¯ãã®åŠãéååç©ã®ååšäžã«æ¢ã«å®æœãã
å Žåã«ã¯ã第ïŒåå¿æ®µéã«ãããŠæ¯ãã®åŠãéå
åç©ãæ·»å ããå¿ èŠã¯ãªããä»ã®å Žåã«ã¯ãæ¯ã
ã®åŠãé©åãªéååç©ãåŒç¶ã第ïŒåå¿æ®µéã®ã
ãã®åå¿æ··åç©ã«æ·»å ãåŸãã
åå¿æ®µéã®åå¿çæç©ã¯ãåœæ¥è ã«æ¢ç¥ã®é©åãª
æ¹æ³ã«ãããäŸãã°èžçãŸãã¯åçµæ¶ã«ãã€ãŠä»
äžããããããšãã§ãããããŠæ¬¡ã®åå¿æ®µéã«çš
ãããåŸããããããäžéäœãåé¢ããã«ãæå
ã®ïŒã€ã®åå¿æ®µéãé ã«å®æœããããšãã§ããã
æ¬çºæã®è£œæ³ã®ãã®å¥œé©ãªå€æ³ã«ãããŠã¯ã第ïŒ
åå¿æ®µéã®åå¿ãç¡æº¶å€ã«ãŠæåã«å®æœãããã
ã®åŸå³åº§ã«ç¬¬ïŒåå¿æ®µéãåãåå¿åšäžã§å®æœ
ãããã®åå¿ã®ããã«å¥œé©ã«ã¯ãåèšã®é©åãªæº¶
å€ã®ïŒã€ãæ·»å ããã第ïŒåå¿æ®µéã«ããããã®
奜é©ãªæº¶å€æ·»å ã¯ã第ïŒåå¿æ®µéã®çºç±åå¿ãå¶
埡ããã®ã«åŸçã§ãããåèšã®åŠãã第ïŒåå¿æ®µ
éã¯å¥œé©ã«ã¯éååç©ã®ååšäžã«å®æœããããå
èšã®éååç©ã®ïŒã€ã¯ç¬¬ïŒåå¿æ®µéãšåæ§ã«ç¬¬ïŒ
åå¿æ®µéã®ããã«ãé©åã§ããããã第ïŒåå¿æ®µ
éãæ¯ãã®åŠãéååç©ã®ååšäžã«æ¢ã«å®æœãã
å Žåã«ã¯ã第ïŒåå¿æ®µéã«ãããŠæ¯ãã®åŠãéå
åç©ãæ·»å ããå¿ èŠã¯ãªããä»ã®å Žåã«ã¯ãæ¯ã
ã®åŠãé©åãªéååç©ãåŒç¶ã第ïŒåå¿æ®µéã®ã
ãã®åå¿æ··åç©ã«æ·»å ãåŸãã
奜é©ã«ã¯æ¬çºæã®è£œæ³ã¯æ¬¡ã®åŠãã«å®æœãã
ãã
ãã
è³éŠæååç©ã®æ žã®èçŽ åãä¿é²ããã®ã«å¿
èŠ
ãªç©è³ªã§ããïœâã¯ããâãã³ãŸããªã¯ããªãã
ããã³é©åãªå Žåã«ã¯æº¶å€ãããæ¹æãããè£ çœ®
äžã«æåã«å°å ¥ããææ枩床ã«å ç±ããã次ã«æ¹
æããªããæ°æéã«ããã€ãŠæ·»å ããã奜é©ãªå€
æ³ã«ãããŠã¯ãåŒç¶ãæ°æéæ¹æããåŸã«ãé©å
ã§ãããšããŠåèšã«èšããã溶å€ã®ïŒã€ãæ·»å
ãããããŠãŸã奜é©ãªå€æ³ã«ãããšãåå¿æ··åç©
ã第ïŒåå¿æ®µéããéååç©ãå«ãã§ããªãå Žå
ã«ã¯ãåèšã®éååç©ã®ïŒã€ãæ·»å ããã次ã«ç¬¬
ïŒåå¿æ®µéã®ããã«æãŸãã枩床ã確ç«ããéžæ
ããã枩床ãä¿ããããããªé床ã«ãŠæ°Žã滎äžã
ãã
ãªç©è³ªã§ããïœâã¯ããâãã³ãŸããªã¯ããªãã
ããã³é©åãªå Žåã«ã¯æº¶å€ãããæ¹æãããè£ çœ®
äžã«æåã«å°å ¥ããææ枩床ã«å ç±ããã次ã«æ¹
æããªããæ°æéã«ããã€ãŠæ·»å ããã奜é©ãªå€
æ³ã«ãããŠã¯ãåŒç¶ãæ°æéæ¹æããåŸã«ãé©å
ã§ãããšããŠåèšã«èšããã溶å€ã®ïŒã€ãæ·»å
ãããããŠãŸã奜é©ãªå€æ³ã«ãããšãåå¿æ··åç©
ã第ïŒåå¿æ®µéããéååç©ãå«ãã§ããªãå Žå
ã«ã¯ãåèšã®éååç©ã®ïŒã€ãæ·»å ããã次ã«ç¬¬
ïŒåå¿æ®µéã®ããã«æãŸãã枩床ã確ç«ããéžæ
ããã枩床ãä¿ããããããªé床ã«ãŠæ°Žã滎äžã
ãã
ãã®ç®çã®ããã«ãé©åãªãã°åå¿æ··åç©ãé©
åãªå·¥åã«å·åŽãããæ·»å ãããæ°Žã¯åèšã®å°ã¢
ã«éå°éãå«ããæ°Žã®æ·»å äžã«ãå¡©åæ°ŽçŽ ãåå¿
æ··åç©ããæŸåºãããé©åãªåžåè£ çœ®äžã«è£éã
ãããå¡©åæ°ŽçŽ ã®æŸåºãçµã€ãæã«ãåå¿æ··åç©
ã«ããªãã«ã¯ããªããæ·»å ãããããªãã«ã¯ããª
ãã®éã¯ãå°ãªããšããéå°éã®æ°Žãé€å»ããã
ãŠåèšã®å¯çç©åœ¢æãé¶ã«ããã®ã«å åãªéã§ãª
ããã°ãªããªãããã®éããéå°éã®ããªãã«ã¯
ããªããæ·»å ããŠããæ¬çºæã®è£œæ³ã«æªåœ±é¿ã¯å
ãŒãããªãã溶å€ããã³éå°éã®ããªãã«ã¯ããª
ãã次ã«çåºãããææåå¿çæç©ãåæ§ã«èžç
ã«ãã€ãŠåé¢ããã
åãªå·¥åã«å·åŽãããæ·»å ãããæ°Žã¯åèšã®å°ã¢
ã«éå°éãå«ããæ°Žã®æ·»å äžã«ãå¡©åæ°ŽçŽ ãåå¿
æ··åç©ããæŸåºãããé©åãªåžåè£ çœ®äžã«è£éã
ãããå¡©åæ°ŽçŽ ã®æŸåºãçµã€ãæã«ãåå¿æ··åç©
ã«ããªãã«ã¯ããªããæ·»å ãããããªãã«ã¯ããª
ãã®éã¯ãå°ãªããšããéå°éã®æ°Žãé€å»ããã
ãŠåèšã®å¯çç©åœ¢æãé¶ã«ããã®ã«å åãªéã§ãª
ããã°ãªããªãããã®éããéå°éã®ããªãã«ã¯
ããªããæ·»å ããŠããæ¬çºæã®è£œæ³ã«æªåœ±é¿ã¯å
ãŒãããªãã溶å€ããã³éå°éã®ããªãã«ã¯ããª
ãã次ã«çåºãããææåå¿çæç©ãåæ§ã«èžç
ã«ãã€ãŠåé¢ããã
第ïŒåå¿æ®µéã«ã€ããŠã¯ã溶å€ãåŒåã«ãªãŠ
ã ãããã³ç¬¬ïŒåå¿æ®µéããã®åå¿çæç©ããæ¹
æããªããéžæããã枩床ã«æ°æéå ç±ãããèž
çã«ãã€ãŠç¬¬ïŒåå¿æ®µéã®åå¿æ··åç©ãåé¢ãã
ããšã«ãã€ãŠãïŒâãã«ãªãâïŒâããã¢âãã³
ãŸã€ã«ãã«ãªãªããåé¢ãããåŒåã«ãªãŠã ã®å¹Ÿ
éšåããåŒåãããªãŠã ã§çœ®ãæããã第ïŒåå¿
段éã®å€æ³ã®å Žåã«ã¯ã奜é©ãªæé ã¯æ¬¡ã®åŠãã§
ããïŒç¬¬ïŒåå¿æ®µéããã®åå¿çæç©ãã¢ã«ã«ãª
éå±ãã«ãªãªãå šéã®50ã¢ã«ïŒ ã«å¯Ÿå¿ããéã®åŒ
åãããªãŠã ãããã³æº¶å€ã®çŽååããæ¹æããª
ããææ枩床ã«æ°æéå ç±ãããæ®éã®æº¶å€äžã«
æžæ¿ããããããåŒåã«ãªãŠã ã次ã«ãã¢ã«ã«ãª
éå±ãã«ãªãªãå šéã®æ®ãã®50ã¢ã«ïŒ ã«å¯Ÿå¿ãã
éã«ãŠåå¿æ··åç©ã«æ·»å ãããåå¿æž©åºŠã«ãŠåŒç¶
ãæ°æéæ¹æããåŸã«ãåå¿æ··åç©ãåèšã®åŠã
ã«ä»äžããã
ã ãããã³ç¬¬ïŒåå¿æ®µéããã®åå¿çæç©ããæ¹
æããªããéžæããã枩床ã«æ°æéå ç±ãããèž
çã«ãã€ãŠç¬¬ïŒåå¿æ®µéã®åå¿æ··åç©ãåé¢ãã
ããšã«ãã€ãŠãïŒâãã«ãªãâïŒâããã¢âãã³
ãŸã€ã«ãã«ãªãªããåé¢ãããåŒåã«ãªãŠã ã®å¹Ÿ
éšåããåŒåãããªãŠã ã§çœ®ãæããã第ïŒåå¿
段éã®å€æ³ã®å Žåã«ã¯ã奜é©ãªæé ã¯æ¬¡ã®åŠãã§
ããïŒç¬¬ïŒåå¿æ®µéããã®åå¿çæç©ãã¢ã«ã«ãª
éå±ãã«ãªãªãå šéã®50ã¢ã«ïŒ ã«å¯Ÿå¿ããéã®åŒ
åãããªãŠã ãããã³æº¶å€ã®çŽååããæ¹æããª
ããææ枩床ã«æ°æéå ç±ãããæ®éã®æº¶å€äžã«
æžæ¿ããããããåŒåã«ãªãŠã ã次ã«ãã¢ã«ã«ãª
éå±ãã«ãªãªãå šéã®æ®ãã®50ã¢ã«ïŒ ã«å¯Ÿå¿ãã
éã«ãŠåå¿æ··åç©ã«æ·»å ãããåå¿æž©åºŠã«ãŠåŒç¶
ãæ°æéæ¹æããåŸã«ãåå¿æ··åç©ãåèšã®åŠã
ã«ä»äžããã
æ¬çºæã®è£œæ³ã«ãããŠã¯ãæ°èŠååç©ïŒâãã«
ãªãâïŒâããã¢âãã³ãŸã€ã«ãã«ãªãªãã¯ãå
å¿æ®µéå šãŠã«ããã€ãŠé«åçã«ãŠåŸããåŸããæ¬
çºæã®è£œæ³ã®åå¿æ®µéã®å šãŠãå®è³ªç床åã®å¯å
å¿ãªãã«é²è¡ããŠãå€ãã®ç°æ§äœãå«ãæ··åç©ã§
ã¯ãªããŠãåçŽãªèžçã«ãã€ãŠåé¢ããåŸãåå¿
æ··åç©ãåŸãããããšã¯æå€ã§ãããåå¿æ··åç©
ãé«æž©ã«ãŠèé ·ãªç±ã«ããããã第ïŒåå¿æ®µéã«
ã€ããŠãå®è³ªçå¯åå¿ãçããªãããšã¯ç¹ã«æå€
ã§ããã
ãªãâïŒâããã¢âãã³ãŸã€ã«ãã«ãªãªãã¯ãå
å¿æ®µéå šãŠã«ããã€ãŠé«åçã«ãŠåŸããåŸããæ¬
çºæã®è£œæ³ã®åå¿æ®µéã®å šãŠãå®è³ªç床åã®å¯å
å¿ãªãã«é²è¡ããŠãå€ãã®ç°æ§äœãå«ãæ··åç©ã§
ã¯ãªããŠãåçŽãªèžçã«ãã€ãŠåé¢ããåŸãåå¿
æ··åç©ãåŸãããããšã¯æå€ã§ãããåå¿æ··åç©
ãé«æž©ã«ãŠèé ·ãªç±ã«ããããã第ïŒåå¿æ®µéã«
ã€ããŠãå®è³ªçå¯åå¿ãçããªãããšã¯ç¹ã«æå€
ã§ããã
æ°èŠãªïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€ã«
ãã«ãªãªãã¯ãã¢ã«ã«ãªæ¡ä»¶äžã«ãŠé¹žåãããŠïŒ
âãã«ãªãâïŒâããã¢âå®æ¯éŠé žãçãåŸãã
ãã®é žã¯é«æŽ»æ§æ®ºè«å€ã®è£œé ã®ããã®éèŠãªäžé
äœã§ããããã®è£œé ã®ããã«ã¯ããããªãŠã ããš
ãã©ãŒãã§ïŒâãã«ãªãâïŒâããã¢âå®æ¯éŠé ž
ãïŒâãã«ãªãâïŒâããšããã·âå®æ¯éŠé žã«è»¢
åãããã®é žããéå ã«ãã€ãŠå¯Ÿå¿ãã³ãžã«ã¢ã«
ã³ãŒã«ãåŸãããã®ã¢ã«ã³ãŒã«ã¯æ¬¡ã«å¯Ÿå¿ããã
ã³ãºã¢ã«ãããã«é žåãããããšãã§ããããã¯
éå±ã·ã¢ã³åç©ãšåå¿ããããããŠÎ±âã·ã¢ãâ
ïŒâãã«ãªãâïŒâããšããã·âãã³ãžã«ã¢ã«ã³
ãŒã«ãçãåŸãããã®ã¢ã«ã³ãŒã«ã®ããŒã¡ã¹ãªã³
é žãšã¹ãã«ïŒpermethric acid estersïŒã¯ã蟲æ¥
ã«ããã害è«ãé§é€ããããã®é¡èãªæ®ºè«å€ã§ã
ãïŒDEâOSïŒç¬åœç¹èš±åºé¡å ¬éå ¬å ±ç¬¬2709264
å·ïŒã
ãã«ãªãªãã¯ãã¢ã«ã«ãªæ¡ä»¶äžã«ãŠé¹žåãããŠïŒ
âãã«ãªãâïŒâããã¢âå®æ¯éŠé žãçãåŸãã
ãã®é žã¯é«æŽ»æ§æ®ºè«å€ã®è£œé ã®ããã®éèŠãªäžé
äœã§ããããã®è£œé ã®ããã«ã¯ããããªãŠã ããš
ãã©ãŒãã§ïŒâãã«ãªãâïŒâããã¢âå®æ¯éŠé ž
ãïŒâãã«ãªãâïŒâããšããã·âå®æ¯éŠé žã«è»¢
åãããã®é žããéå ã«ãã€ãŠå¯Ÿå¿ãã³ãžã«ã¢ã«
ã³ãŒã«ãåŸãããã®ã¢ã«ã³ãŒã«ã¯æ¬¡ã«å¯Ÿå¿ããã
ã³ãºã¢ã«ãããã«é žåãããããšãã§ããããã¯
éå±ã·ã¢ã³åç©ãšåå¿ããããããŠÎ±âã·ã¢ãâ
ïŒâãã«ãªãâïŒâããšããã·âãã³ãžã«ã¢ã«ã³
ãŒã«ãçãåŸãããã®ã¢ã«ã³ãŒã«ã®ããŒã¡ã¹ãªã³
é žãšã¹ãã«ïŒpermethric acid estersïŒã¯ã蟲æ¥
ã«ããã害è«ãé§é€ããããã®é¡èãªæ®ºè«å€ã§ã
ãïŒDEâOSïŒç¬åœç¹èš±åºé¡å ¬éå ¬å ±ç¬¬2709264
å·ïŒã
åŸã€ãŠã該ããŒã¡ã¹ãªã³é
žãšã¹ãã«ã®è£œé ã®ã
ãã®éèŠãªååç©ã¯ãïŒâãã«ãªãâïŒâããã¢
âå®æ¯éŠé žã§ãããããã¯æ¢ç¥ã§ããããããŠã
ãã©ãã«ãªç¡Œé žäžã§ã®ïŒâããã¢âïŒâã¡ãã«â
ã¢ããªã³ã®ãžã¢ãŸåã«ãã€ãŠåŸãããïŒâãã«ãª
ãâïŒâããã¢âãã«ãšã³ã®é žåã«ãããå€æ®µé
ãããªã浪費ç補æ³ã«ããŠåŸããåŸãïŒCan.J.
Chem.31å·»ã2444ïŒ1960ïŒïŒããã®è£œæ³ã¯å¹Ÿã€ãã®
æ¬ ç¹ãæãïŒãããã«ãåŒçŽ ååå°å ¥æ¹æ³ã¯ãã
ã©ãã«ãªãç¡Œé žäžã«ãŠå®æœããããã®é žã¯ãžã¢ãŸ
åã®çµæãšããŠæ°ŽåãåŸãŠãè èå¹æãããã
ããããã«ãïŒâãã«ãªãâïŒâããã¢âãã«ãš
ã³ã®é žåã«ãããåçãäœãããšã¯ãé倧ãªæ¬ ç¹
ã§ãããæåŸã«ãïœâã¢ãããã«ãšã³ã¯ãæåã«
ã¢ã·ã«åãã次ã«èçŽ åãããæåŸã«ãCan.J.
Chem.ãloc.cit.ã«èšèŒã®åå¿ã·ãŒã±ã³ã¹ãå§ãåŸ
ãããã«ãªãåã«ãåã³ã¢ã»ãã«åºãé€å»ãããª
ããã°ãªããªãå·¥æ¥ççŽã®åºçºææã§ãããšã¿ãª
ãããã¹ãã§ããã
ãã®éèŠãªååç©ã¯ãïŒâãã«ãªãâïŒâããã¢
âå®æ¯éŠé žã§ãããããã¯æ¢ç¥ã§ããããããŠã
ãã©ãã«ãªç¡Œé žäžã§ã®ïŒâããã¢âïŒâã¡ãã«â
ã¢ããªã³ã®ãžã¢ãŸåã«ãã€ãŠåŸãããïŒâãã«ãª
ãâïŒâããã¢âãã«ãšã³ã®é žåã«ãããå€æ®µé
ãããªã浪費ç補æ³ã«ããŠåŸããåŸãïŒCan.J.
Chem.31å·»ã2444ïŒ1960ïŒïŒããã®è£œæ³ã¯å¹Ÿã€ãã®
æ¬ ç¹ãæãïŒãããã«ãåŒçŽ ååå°å ¥æ¹æ³ã¯ãã
ã©ãã«ãªãç¡Œé žäžã«ãŠå®æœããããã®é žã¯ãžã¢ãŸ
åã®çµæãšããŠæ°ŽåãåŸãŠãè èå¹æãããã
ããããã«ãïŒâãã«ãªãâïŒâããã¢âãã«ãš
ã³ã®é žåã«ãããåçãäœãããšã¯ãé倧ãªæ¬ ç¹
ã§ãããæåŸã«ãïœâã¢ãããã«ãšã³ã¯ãæåã«
ã¢ã·ã«åãã次ã«èçŽ åãããæåŸã«ãCan.J.
Chem.ãloc.cit.ã«èšèŒã®åå¿ã·ãŒã±ã³ã¹ãå§ãåŸ
ãããã«ãªãåã«ãåã³ã¢ã»ãã«åºãé€å»ãããª
ããã°ãªããªãå·¥æ¥ççŽã®åºçºææã§ãããšã¿ãª
ãããã¹ãã§ããã
å察ã«ãæ¬çºæã®è£œæ³ã®åºçºææã§ããïœâã¯
ããâãã³ãŸããªã¯ããªãã¯ãïœâã¯ããâãã«
ãšã³ã®å¡©çŽ åã«ãã容æã«æ¥è¿å¯èœã§ãã
ïŒHoubenâWeylãïŒïŒå·»ãGeorg Thiemeã
Stuttgart1962ãé 738ïŒããããŠæ¬çºæã®è£œæ³ã¯
è¥å¹²ã®é«åç段éã«ãŠæ¬çºæã«åŸã€ãŠïŒâãã«ãª
ãâïŒâããã¢âãã³ãŸã€ã«ãã«ãªãªããããã
ããããã¯å®è³ªçã«å®éçã«ïŒâãã«ãªãâïŒâ
ããã¢âå®æ¯éŠé žã«è»¢åããåŸãã
ããâãã³ãŸããªã¯ããªãã¯ãïœâã¯ããâãã«
ãšã³ã®å¡©çŽ åã«ãã容æã«æ¥è¿å¯èœã§ãã
ïŒHoubenâWeylãïŒïŒå·»ãGeorg Thiemeã
Stuttgart1962ãé 738ïŒããããŠæ¬çºæã®è£œæ³ã¯
è¥å¹²ã®é«åç段éã«ãŠæ¬çºæã«åŸã€ãŠïŒâãã«ãª
ãâïŒâããã¢âãã³ãŸã€ã«ãã«ãªãªããããã
ããããã¯å®è³ªçã«å®éçã«ïŒâãã«ãªãâïŒâ
ããã¢âå®æ¯éŠé žã«è»¢åããåŸãã
ãããã«ãæ¬çºæã®ããïŒã€ã®åŽé¢ã¯ãïŒâã
ã«ãªãâïŒâããã¢âå®æ¯éŠé žã®è£œæ³ã«ãããŠã
ïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€ã«ãã«ãªãª
ããæåã«ã¢ã«ã«ãªæ§ç©è³ªãšåå¿ãããïŒâãã«
ãªãâïŒâããã¢âå®æ¯éŠé žã次ã«é±é žã«ãã€
ãŠãçããå¡©ããéé¢ãããããšãç¹åŸŽãšãã補
æ³ã«é¢ããã
ã«ãªãâïŒâããã¢âå®æ¯éŠé žã®è£œæ³ã«ãããŠã
ïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€ã«ãã«ãªãª
ããæåã«ã¢ã«ã«ãªæ§ç©è³ªãšåå¿ãããïŒâãã«
ãªãâïŒâããã¢âå®æ¯éŠé žã次ã«é±é žã«ãã€
ãŠãçããå¡©ããéé¢ãããããšãç¹åŸŽãšãã補
æ³ã«é¢ããã
ã¢ã«ã«ãªæ§ç©è³ªã®äŸãšããŠã¯ã¢ã«ã«ãªéå±çé
ž
å¡©ãŸãã¯ã¢ã«ã«ãªéå±æ°Žé žåç©äŸãã°çé žãããª
ãŠã ãéçé žãããªãŠã ãçé žã«ãªãŠã ãéçé ž
ã«ãªãŠã ãæ°Žé žåã«ãªãŠã ãŸãã¯å¥œé©ã«ã¯æ°Žé žå
ãããªãŠã ãæãåŸãã
å¡©ãŸãã¯ã¢ã«ã«ãªéå±æ°Žé žåç©äŸãã°çé žãããª
ãŠã ãéçé žãããªãŠã ãçé žã«ãªãŠã ãéçé ž
ã«ãªãŠã ãæ°Žé žåã«ãªãŠã ãŸãã¯å¥œé©ã«ã¯æ°Žé žå
ãããªãŠã ãæãåŸãã
é±é
žã®äŸãšããŠã¯çé
žãç¡é
žãŸãã¯å¥œçã«ã¯å¡©
é žãŸãã¯ç¡«é žã®æ¿ãŸãã¯åžæ°Žæº¶æ¶²ãæãåŸãã
é žãŸãã¯ç¡«é žã®æ¿ãŸãã¯åžæ°Žæº¶æ¶²ãæãåŸãã
ïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€ã«ãã«ãª
ãªãããã®ïŒâãã«ãªãâïŒâããã¢âå®æ¯éŠé ž
ã®è£œé ã¯ãäŸãã°åå¿åªäœãšããŠã®æ°Žã®äžã«ãŠ20
â100âã«ãŠå®æœããåŸãã
ãªãããã®ïŒâãã«ãªãâïŒâããã¢âå®æ¯éŠé ž
ã®è£œé ã¯ãäŸãã°åå¿åªäœãšããŠã®æ°Žã®äžã«ãŠ20
â100âã«ãŠå®æœããåŸãã
æ¬çºæã®è£œæ³ã次ã®è£œé äŸã«ãã説æããã
äŸ ïŒ
2776ïœïŒ12ã¢ã«ïŒã®ïœâã¯ããâãã³ãŸããªã¯
ããªããïŒïœã®ç²æ«ç¡«åéããã³ïŒïœã®ç¡æ°Žé
ïŒïŒã¯ããªããæåã«ïŒãªããã«ïŒã€å£ãã©ã¹
ã³ã«å°å ¥ãã50âã«ãŠïŒâïŒæéã«ããã€ãŠæ¹æ
ããªãã2200ïœïŒ13.75ã¢ã«ïŒã®èçŽ ãæ·»å ããã
æ··åç©ã次ãã§ïŒâ10æéæ¹æãã3.2ãªããã«
ã®ïŒïŒïŒâãžã¯ãããšã¿ã³ã次ã«æ·»å ãã枩床ã
70âã«äžããçŽïŒâïŒæéã«ããã€ãŠ248ïœ
ïŒ13.75ã¢ã«ïŒã®æ°Žãèšéæ·»å ãããå¡©åæ°ŽçŽ ã®æŸ
åºãæ¢ãŸããšçŽãã«200mlã®ããªãã«ã¯ããªãã
åå¿æ··åç©ã«æ·»å ãããäºé žåç¡«é»ã®æŸåºãæ¢ãŸ
ã€ãæã«ã溶å€ããã³æ®çããªãã«ã¯ããªããç
åºãããïŒâã¯ããâïŒâããã¢âãã³ãŸã€ã«ã¯
ããªããåæ§ã«èžçã«ãã€ãŠåé¢ããã沞ç¹98
âïŒ0.5ããªããŒã«ã®ãã®2730ïœãåŸããããã
ãã¯çè«åéã®89ïŒ ã«å¯Ÿå¿ããã
ããªããïŒïœã®ç²æ«ç¡«åéããã³ïŒïœã®ç¡æ°Žé
ïŒïŒã¯ããªããæåã«ïŒãªããã«ïŒã€å£ãã©ã¹
ã³ã«å°å ¥ãã50âã«ãŠïŒâïŒæéã«ããã€ãŠæ¹æ
ããªãã2200ïœïŒ13.75ã¢ã«ïŒã®èçŽ ãæ·»å ããã
æ··åç©ã次ãã§ïŒâ10æéæ¹æãã3.2ãªããã«
ã®ïŒïŒïŒâãžã¯ãããšã¿ã³ã次ã«æ·»å ãã枩床ã
70âã«äžããçŽïŒâïŒæéã«ããã€ãŠ248ïœ
ïŒ13.75ã¢ã«ïŒã®æ°Žãèšéæ·»å ãããå¡©åæ°ŽçŽ ã®æŸ
åºãæ¢ãŸããšçŽãã«200mlã®ããªãã«ã¯ããªãã
åå¿æ··åç©ã«æ·»å ãããäºé žåç¡«é»ã®æŸåºãæ¢ãŸ
ã€ãæã«ã溶å€ããã³æ®çããªãã«ã¯ããªããç
åºãããïŒâã¯ããâïŒâããã¢âãã³ãŸã€ã«ã¯
ããªããåæ§ã«èžçã«ãã€ãŠåé¢ããã沞ç¹98
âïŒ0.5ããªããŒã«ã®ãã®2730ïœãåŸããããã
ãã¯çè«åéã®89ïŒ ã«å¯Ÿå¿ããã
第ïŒåå¿æ®µéã«ã€ããŠã¯ãåŸãããïŒâã¯ãã
âïŒâããã¢âãã³ãŸã€ã«ã¯ããªãã®å¹Ÿåããå³
ã¡1825ïœïŒïŒã¢ã«ïŒãã3250ïœã®ããã©ã¡ãã¬ã³
ã¹ã«ãã³ããã³1250ïœïŒ21ã¢ã«ïŒã®ç¡æ°ŽåŒåã«ãª
ãŠã ãšå ±ã«ïŒæéã«ããã€ãŠæ¹æããªãã210â
ã«å ç±ããã次ãã§èžçããããšã«ãã€ãŠã沞ç¹
92â95âïŒ18ããªããŒã«ã®1330ïœã®ïŒâãã«ãªã
âïŒâããã¢âãã³ãŸã€ã«ãã«ãªãªããåŸããã
ãã¯çè«éã®83ïŒ ã«å¯Ÿå¿ããã
âïŒâããã¢âãã³ãŸã€ã«ã¯ããªãã®å¹Ÿåããå³
ã¡1825ïœïŒïŒã¢ã«ïŒãã3250ïœã®ããã©ã¡ãã¬ã³
ã¹ã«ãã³ããã³1250ïœïŒ21ã¢ã«ïŒã®ç¡æ°ŽåŒåã«ãª
ãŠã ãšå ±ã«ïŒæéã«ããã€ãŠæ¹æããªãã210â
ã«å ç±ããã次ãã§èžçããããšã«ãã€ãŠã沞ç¹
92â95âïŒ18ããªããŒã«ã®1330ïœã®ïŒâãã«ãªã
âïŒâããã¢âãã³ãŸã€ã«ãã«ãªãªããåŸããã
ãã¯çè«éã®83ïŒ ã«å¯Ÿå¿ããã
äŸ ïŒ
æåã®ïŒã€ã®åå¿æ®µéãäŸïŒã®åŠãã«å®æœã
ãã次ã«1270ïœïŒïŒã¢ã«ïŒã®ïŒâã¯ããâïŒâã
ãã¢âãã³ãŸã€ã«ã¯ããªããã1150ïœã®ããã©ã¡
ãã¬ã³ã¹ã«ãã³ããã³315ïœïŒ7.5ã¢ã«ïŒã®ç¡æ°ŽåŒ
åãããªãŠã ãšå ±ã«ïŒæéæ¹æããªãã210âã«
å ç±ããã次ã«1150ïœã®ããã©ã¡ãã¬ã³ã¹ã«ãã³
äžã«æžæ¿ãããããã435ïœïŒ7.5ã¢ã«ïŒã®ç¡æ°ŽåŒ
åã«ãªãŠã ãåå¿æ··åç©ã«æ·»å ããæ··åç©ã210
âã«ãŠããã«ïŒæéæ¹æããã次ãã§èžçããã
ãšã«ãã€ãŠã873ïœã®ïŒâãã«ãªãâïŒâããã¢
âãã³ãŸã€ã«ãã«ãªãªããåŸããããã¯çè«éã®
79ïŒ ã«å¯Ÿå¿ããã
ãã次ã«1270ïœïŒïŒã¢ã«ïŒã®ïŒâã¯ããâïŒâã
ãã¢âãã³ãŸã€ã«ã¯ããªããã1150ïœã®ããã©ã¡
ãã¬ã³ã¹ã«ãã³ããã³315ïœïŒ7.5ã¢ã«ïŒã®ç¡æ°ŽåŒ
åãããªãŠã ãšå ±ã«ïŒæéæ¹æããªãã210âã«
å ç±ããã次ã«1150ïœã®ããã©ã¡ãã¬ã³ã¹ã«ãã³
äžã«æžæ¿ãããããã435ïœïŒ7.5ã¢ã«ïŒã®ç¡æ°ŽåŒ
åã«ãªãŠã ãåå¿æ··åç©ã«æ·»å ããæ··åç©ã210
âã«ãŠããã«ïŒæéæ¹æããã次ãã§èžçããã
ãšã«ãã€ãŠã873ïœã®ïŒâãã«ãªãâïŒâããã¢
âãã³ãŸã€ã«ãã«ãªãªããåŸããããã¯çè«éã®
79ïŒ ã«å¯Ÿå¿ããã
äŸïŒ ïŒåèäŸïŒ
1200mlã®æ°Žã®äžã«å«ãŸãã100ïœã®æ°Žé
žåãã
ãªãŠã ãæåã«åå¿å®¹åšã«å°å ¥ããæ¹æããªãã
265ïœã®ïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€ã«
ãã«ãªãªãã滎äžãããæ·»å ãçµäºããããŠåºäœ
ãå šãŠæº¶è§£ããæã«ã溶液ãæ¿å¡©é žã§é žæ§åã
ããæ²æ®¿ããçæç©ãå¥ãã埪ç°ç©ºæ°ãã€ãã
ããå ã§100âã«ãŠä¹Ÿç¥ããã252ïœïŒçè«åéã®
96ïŒ ïŒã®ïŒâãã«ãªãâïŒâããã¢âå®æ¯éŠé žã
åŸãããïŒèç¹ïŒ134â136âã
ãªãŠã ãæåã«åå¿å®¹åšã«å°å ¥ããæ¹æããªãã
265ïœã®ïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€ã«
ãã«ãªãªãã滎äžãããæ·»å ãçµäºããããŠåºäœ
ãå šãŠæº¶è§£ããæã«ã溶液ãæ¿å¡©é žã§é žæ§åã
ããæ²æ®¿ããçæç©ãå¥ãã埪ç°ç©ºæ°ãã€ãã
ããå ã§100âã«ãŠä¹Ÿç¥ããã252ïœïŒçè«åéã®
96ïŒ ïŒã®ïŒâãã«ãªãâïŒâããã¢âå®æ¯éŠé žã
åŸãããïŒèç¹ïŒ134â136âã
Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ ååç©ïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€
ã«ãã«ãªãªãã ïŒ ïŒâãã«ãªãâïŒâããã¢âãã³ãŸã€ã«ãã«
ãªãªãã®è£œæ³ã«ãããŠãïœâã¯ããâãã³ãŸâã
ãªã¯ããªããæåã«èçŽ åãã次ã«ããªã¯ããã¡
ãã«åºãéšåå æ°Žå解ããçããäžéäœãåŒçŽ å
å€ãšåå¿ãããããšãç¹åŸŽãšãã補æ³ã ïŒ è³éŠæååç©ã®æ žã®èçŽ åãä¿é²ããç©è³ªã®
ååšäžã«ããããŠé©åãªãã°äžæŽ»æ§æº¶å€ã®ååšäž
ã«ãŠãå çŽ ç¶èçŽ ãçšããŠèçŽ åãå®æœãããç¹
èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®è£œæ³ã ïŒ è³éŠæååç©ã®æ žã®èçŽ åãä¿é²ããç©è³ªãš
ããŠãå çŽ ç¶ãŸãã¯çµå圢æ ã®éãçšãããç¹èš±
è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®è£œæ³ã ïŒ ïœâã¯ããâãã³ãŸããªã¯ããªãïŒã¢ã«åœã
ïŒâ1.2ã¢ã«ã®èçŽ ãçšãããç¹èš±è«æ±ã®ç¯å²ç¬¬
ïŒãŸãã¯ïŒé èšèŒã®è£œæ³ã ïŒ è³éŠæååç©ã®æ žã®èçŽ åãä¿é²ããç©è³ª
ããïœâã¯ããâãã³ãŸããªã¯ããªãã«åºã¥ããŠ
0.01âïŒééïŒ ã®éã«ãŠçšãããç¹èš±è«æ±ã®ç¯å²
第ïŒãïŒãŸãã¯ïŒé èšèŒã®è£œæ³ã ïŒ èçŽ åã20ãâ70âã«ãŠå®æœãããç¹èš±è«æ±
ã®ç¯å²ç¬¬ïŒâïŒé ã®ããããäžé èšèŒã®è£œæ³ã ïŒ æ°Žãçšããè³éŠæçã«çµåããããªã¯ããã¡
ãã«åºã®å æ°Žå解ãä¿é²ããç©è³ªã®ååšäžã«ãã
ããŠé©åãªãã°äžæŽ»æ§æº¶å€ã®ååšäžã«ãŠãéšåå
æ°Žå解ãå®æœããéå°éã®æ°Žããã³ïŒãŸãã¯éå°
éã®æ°Žã«ãã€ãŠåœ¢æãããå¯çç©ããé©åãªãã°
ããªãã«ã¯ããªããšã®åå¿ã«ãã€ãŠãé€å»ããã
ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒâïŒé ã®ããããäžé èšèŒã®
補æ³ã ïŒ è³éŠæçã«çµåããããªã¯ããã¡ãã«åºã®å
æ°Žå解ãä¿é²ããç©è³ªãéååç©ã§ãããç¹èš±è«
æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®è£œæ³ã ïŒïŒ è³éŠæçã«çµåããããªã¯ããã¡ãã«åºã®
å æ°Žå解ãä¿é²ããç©è³ªãã䜿çšïœâã¯ããâã
ã³ãŸããªã¯ããªãã«å¯ŸããŠ0.01âïŒééïŒ ã®éã«
ãŠçšãããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒãŸãã¯ïŒé èšèŒã®
補æ³ã ïŒïŒ äžéçä»äžãç¡ãã«ãŠãèçŽ åããã³éšå
å æ°Žå解ãåäžåå¿åšäžã§å®æœãããç¹èš±è«æ±ã®
ç¯å²ç¬¬ïŒâïŒïŒé ã®ããããäžé èšèŒã®è£œæ³ã ïŒïŒ å æ°Žå解ã®ããã«ã䜿çšïœâã¯ããâãã³
ãŸããªã¯ããªãïŒã¢ã«åœãïŒâ1.2ã¢ã«ã®æ°Žãçš
ãããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒâïŒïŒé ã®ããããäž
é èšèŒã®è£œæ³ã ïŒïŒ å æ°Žå解ã20ãâ100âã«ãŠå®æœãããç¹èš±
è«æ±ã®ç¯å²ç¬¬ïŒâïŒïŒé ã®ããããäžé èšèŒã®è£œ
æ³ã ïŒïŒ åŒçŽ åå€ãšã®åå¿ã®ããã«ãäžæŽ»æ§æº¶å€ã®
ååšäžã«é«ãããã枩床ã«ãŠåŒåã«ãªãŠã ãçš
ãããã®å¹ŸéšåããåŒåãããªãŠã ã§çœ®ãæãã
ããšãã§ãããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒâïŒïŒé ã®ã
ãããäžé èšèŒã®è£œæ³ã ïŒïŒ ãã«ãªãªãã幟ã€ãã®éšåã«åããŠæ·»å ã
ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒïŒé èšèŒã®è£œæ³ã ïŒïŒ 第ïŒéšåãšããŠåŒåãããªãŠã ãæåã«æ·»
å ãã次ã«ç¬¬ïŒéšåãšããŠåŒåã«ãªãŠã ãæ·»å ã
ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒïŒãŸãã¯ïŒïŒé èšèŒã®è£œ
æ³ã ïŒïŒ åŒåã«ãªãŠã ã®50ã¢ã«ïŒ ããå€ããªãéã
åŒåãããªãŠã ã§çœ®ãæãããç¹èš±è«æ±ã®ç¯å²ç¬¬
ïŒïŒãïŒïŒãŸãã¯ïŒïŒé èšèŒã®è£œæ³ã ïŒïŒ 䜿çšïœâã¯ããâãã³ãŸããªã¯ããªãïŒã¢
ã«åœãïŒâïŒã¢ã«ã®ãã«ãªãªããçšãããç¹èš±è«
æ±ã®ç¯å²ç¬¬ïŒïŒâïŒïŒé ã®ããããäžé èšèŒã®è£œ
æ³ã ïŒïŒ åŒçŽ åãäžæŽ»æ§ã極æ§ãäžæ§ææ©æº¶å€äžã«
ãŠå®æœãããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒâïŒïŒé ã®ãã
ããäžé èšèŒã®è£œæ³ã ïŒïŒ åŒçŽ åã160ãâ220âã«ãŠå®æœãããç¹èš±
è«æ±ã®ç¯å²ç¬¬ïŒâïŒïŒé ã®ããããäžé èšèŒã®è£œ
æ³ã
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792928987 DE2928987A1 (de) | 1979-07-18 | 1979-07-18 | 4-fluor-3-brom-benzoylfluorid und verfahren zu seiner herstellung |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5616441A JPS5616441A (en) | 1981-02-17 |
JPS6334858B2 true JPS6334858B2 (ja) | 1988-07-12 |
Family
ID=6076017
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9630680A Granted JPS5616441A (en) | 1979-07-18 | 1980-07-16 | 44fluoroo33bromoobenzoylfluoride and manufacture thereof |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0024516B1 (ja) |
JP (1) | JPS5616441A (ja) |
BR (1) | BR8004448A (ja) |
DD (1) | DD153204A5 (ja) |
DE (2) | DE2928987A1 (ja) |
DK (1) | DK308880A (ja) |
HU (1) | HU183181B (ja) |
IL (1) | IL60604A (ja) |
PL (1) | PL128170B1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3006685C2 (de) * | 1980-02-22 | 1982-09-09 | Riedel-De Haen Ag, 3016 Seelze | 3-Brom-4-fluorbenzonitril und Verfahren zur Herstellung eines substituierten 3-Brom-4-fluorbenzols |
DE3140634A1 (de) * | 1981-10-13 | 1983-04-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von kernfluorierten benzoylfluoriden |
GB8324902D0 (en) * | 1983-09-16 | 1983-10-19 | Ici Plc | Chemical process |
DE4227371A1 (de) * | 1992-08-19 | 1994-02-24 | Bayer Ag | Verfahren zur Herstellung von 2,3,4-Trichlor-5-fluor-benzoylchlorid |
DE4414841A1 (de) * | 1994-04-28 | 1995-11-02 | Bayer Ag | Brom enthaltende aromatische Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Zwischenprodukte bei der Synthese von Wirkstoffen |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2062434A1 (ja) * | 1970-12-18 | 1972-06-22 | ||
US4113435A (en) * | 1973-07-16 | 1978-09-12 | Massachusetts Institute Of Technology | Cryogenically controlled direct fluorination apparatus |
DE2708190C2 (de) * | 1977-02-25 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von m-Brom-benzotrifluoriden |
DE2743144B2 (de) * | 1977-09-24 | 1979-09-06 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von m-Halogenbenzoylhalogeniden |
-
1979
- 1979-07-18 DE DE19792928987 patent/DE2928987A1/de not_active Withdrawn
-
1980
- 1980-07-09 EP EP80103922A patent/EP0024516B1/de not_active Expired
- 1980-07-09 DE DE8080103922T patent/DE3060704D1/de not_active Expired
- 1980-07-15 IL IL60604A patent/IL60604A/xx not_active IP Right Cessation
- 1980-07-16 DD DD222663A patent/DD153204A5/de unknown
- 1980-07-16 PL PL1980225701A patent/PL128170B1/pl unknown
- 1980-07-16 JP JP9630680A patent/JPS5616441A/ja active Granted
- 1980-07-17 HU HU801790A patent/HU183181B/hu not_active IP Right Cessation
- 1980-07-17 BR BR8004448A patent/BR8004448A/pt not_active IP Right Cessation
- 1980-07-17 DK DK308880A patent/DK308880A/da not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
BR8004448A (pt) | 1981-01-27 |
PL225701A1 (ja) | 1981-12-23 |
EP0024516A1 (de) | 1981-03-11 |
DE2928987A1 (de) | 1981-02-12 |
DD153204A5 (de) | 1981-12-30 |
DK308880A (da) | 1981-01-19 |
EP0024516B1 (de) | 1982-07-28 |
JPS5616441A (en) | 1981-02-17 |
IL60604A (en) | 1984-08-31 |
DE3060704D1 (en) | 1982-09-16 |
HU183181B (en) | 1984-04-28 |
IL60604A0 (en) | 1980-09-16 |
PL128170B1 (en) | 1984-01-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4439620A (en) | 2,4-Dichloro-5-fluorobenzoyl halide and a process for its preparation | |
JPS6334858B2 (ja) | ||
US4876376A (en) | Process for the halogenation, nitration and fluorination of aromatic derivatives | |
CA2090768A1 (en) | Process for the preparation of 2,4,5-trifluorobenzonitrile | |
EP0202838A2 (en) | Process for production of m-phenoxybenzyl alcohol | |
JP2502327B2 (ja) | ãžããšãã«ãšâãã«ååç©ã®è£œé æ¹æ³ | |
US4210766A (en) | Process for producing 2-halo-4-bromophenols | |
JPH0368534A (ja) | ããçŽ åãããå®æ¯éŠé žã®è£œé æ¹æ³ | |
JPH0223535B2 (ja) | ||
JP3677786B2 (ja) | ã¢ãªãŒã«ãªãã·ããããªã³é žã®è£œé æ³ | |
US4330366A (en) | Process for the preparation of halogenated benzoyl fluorides | |
EP0071833B1 (en) | Process for producing 4-benzoylpyrazoles | |
US3703597A (en) | Preparation of benzilic acid compounds | |
KR890003782B1 (ko) | ë-ì€ë¥Ží -ì¹íë ë-ë©í-í ë¡ê²í íëŒ-í ë¡ë©ížíëì ì ì¡°ë°©ë² | |
JPH0225896B2 (ja) | ||
JP3149537B2 (ja) | ïŒïœâãã«ãã«ãªãã¢ã«ã«ã³ã®è£œé æ³ | |
US5047584A (en) | Process for the preparation of pentahaloethoxy benzoyl halide compounds | |
JPS61200938A (ja) | ïŒïŒïŒâ²âãžããããã·ãžããšãã«ãšãŒãã«ã®è£œæ³ | |
JPH10168051A (ja) | ïŒïŒïŒâãžããã²ãâïŒâããªãã«ãªãã¡ãã«ãã³ãŸãããªã«ã®è£œé æ³ | |
US5430202A (en) | Process for the preparation of substantially fluorinated alkyl bromides | |
JP3261474B2 (ja) | ïŒâã¯ããâïŒïŒïŒâãžãã«ãªãå®æ¯éŠé žã®è£œé æ³ | |
JPS6350339B2 (ja) | ||
JPS6148A (ja) | αâã¯ããã¢ã»ãé ¢é žã¢ãã¡ãã«ã¢ããã®è£œé æ¹æ³ | |
JPH026340B2 (ja) | ||
JPH0443055B2 (ja) |