JPH0556334B2 - - Google Patents
Info
- Publication number
- JPH0556334B2 JPH0556334B2 JP85132089A JP13208985A JPH0556334B2 JP H0556334 B2 JPH0556334 B2 JP H0556334B2 JP 85132089 A JP85132089 A JP 85132089A JP 13208985 A JP13208985 A JP 13208985A JP H0556334 B2 JPH0556334 B2 JP H0556334B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- formula
- ether
- organic solvent
- 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 - Fee Related
Links
- 239000003054 catalyst Substances 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- -1 trifluoromethyl- Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 13
- 239000003495 polar organic solvent Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002955 isolation Methods 0.000 claims description 12
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 229910000510 noble metal Inorganic materials 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- WGAXJEXVOSVLFY-UHFFFAOYSA-N 1-(2,4-dinitrophenoxy)-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O WGAXJEXVOSVLFY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229940031826 phenolate Drugs 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000005932 reductive alkylation reaction Methods 0.000 description 6
- WZEPMNYUOAOPIK-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)OCC(OC)N Chemical compound C(C)(=O)NC1=CC=C(C=C1)OCC(OC)N WZEPMNYUOAOPIK-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- IFQVEYUAIINTRX-UHFFFAOYSA-N 2-methoxyethoxybenzene Chemical compound COCCOC1=CC=CC=C1 IFQVEYUAIINTRX-UHFFFAOYSA-N 0.000 description 3
- MTNLEKFLKGGTKS-UHFFFAOYSA-N 4-(2,4-diaminophenoxy)benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OC1=CC=C(N)C=C1N MTNLEKFLKGGTKS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- QRGALPKVWIQXKQ-UHFFFAOYSA-N n-[4-(2-amino-2-methoxyethoxy)phenyl]propanamide Chemical compound CCC(=O)NC1=CC=C(OCC(N)OC)C=C1 QRGALPKVWIQXKQ-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SEJFWAWYAJTLJD-UHFFFAOYSA-N 1-(2,3-dinitrophenoxy)-2,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C(=C(C=CC=2)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O SEJFWAWYAJTLJD-UHFFFAOYSA-N 0.000 description 2
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 2
- CVYZVNVPQRKDLW-UHFFFAOYSA-N 2,4-dinitroanisole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CVYZVNVPQRKDLW-UHFFFAOYSA-N 0.000 description 2
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 2
- GGVZNGYEHJHVMK-UHFFFAOYSA-N 2-(2-methoxyethoxy)aniline Chemical compound COCCOC1=CC=CC=C1N GGVZNGYEHJHVMK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- BIBOUMJSDFPHJJ-UHFFFAOYSA-N N-[4-[2-(ethylamino)-2-methoxyethoxy]phenyl]propanamide Chemical compound CCNC(OC)COC1=CC=C(NC(=O)CC)C=C1 BIBOUMJSDFPHJJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- XTKBLPKQFBQFTC-UHFFFAOYSA-N n-[3-(ethylamino)-4-methoxyphenyl]acetamide Chemical compound CCNC1=CC(NC(C)=O)=CC=C1OC XTKBLPKQFBQFTC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 description 1
- ADHVQCZSFFSNCV-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzene-1,2-diamine Chemical compound COCCOC1=CC=CC(N)=C1N ADHVQCZSFFSNCV-UHFFFAOYSA-N 0.000 description 1
- BFLWXPJTAKXXKT-UHFFFAOYSA-N 3-methoxybenzene-1,2-diamine Chemical compound COC1=CC=CC(N)=C1N BFLWXPJTAKXXKT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YNQNTUVMQPQFEW-UHFFFAOYSA-N methyl 2-hydroxyacetate;sodium Chemical compound [Na].COC(=O)CO YNQNTUVMQPQFEW-UHFFFAOYSA-N 0.000 description 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- BTJCIVXKBILNPY-UHFFFAOYSA-N n-[3-(diethylamino)-4-methoxyphenyl]acetamide Chemical compound CCN(CC)C1=CC(NC(C)=O)=CC=C1OC BTJCIVXKBILNPY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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
æ¬çºæã®å¯Ÿè±¡ã¯ã極æ§ææ©æº¶å€äžã§ã®ïŒïŒïŒâ
ãžãããã¯ãã«ãã³ãŒã³ãšã¢ã«ã«ãªéå±ã¢ã«ã³ã¬
ãŒãåã¯âããšãã¬ãŒããšã®ïŒïŒïŒâãžãããã
ãšãã«ãšãŒãã«ãžã®åå¿ãééå±è§Šåªåã³è§Šåªé
ã®çªçŽ å«æææ©å¡©åºã®ååšäžã§ã®è©²ãšãŒãã«ã®
ïŒïŒïŒâãžã¢ããããšãã«ãšãŒãã«ãžã®éå ãïŒ
âã¢ã·ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«
ãžã®éžæçã¢ã·ã«ååã³ééå±è§Šåªåã³è§Šåªéã®
çªçŽ å«æææ©å¡©åºã®ååšäžã§ã®è©²ãšãŒãã«ã®ã¢ã«
ãããã§ã®éå çã¢ã«ãã«åã«ããïŒâã¢ã·ã«ã¢
ããâïŒâã¢ã«ãã«ã¢ããâããšãã«ãšãŒãã«ã®
補æ³ã§ããã ïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³ããã®ïŒâã¢
ã·ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«ã®è£œ
é ã¯ååçã«æç®äžå ¬ç¥ã§ããïŒæ¬§å·ç¹èš±ç¬¬
0011048å·ïŒã䜵ãããã§èšèŒã®ïŒïŒïŒâãžããã¯
ãã«ãã³ãŒã³ãšã¢ã«ã³ãŒã«ïŒã¢ã«ã«ãªæ¶²åã¯ã¢ã«
ã³ãŒã«ïŒã¢ã«ã«ãªæ°Žé žåç©ãšãåå¿ãããŠå¯Ÿå¿ã
ãïŒïŒïŒâãžãããããšãã«ãšãŒãã«ãšããå Žå
ïŒïŒïŒâãžãããããšããŒã«ã®çæãå®å šã«æé€
ããããšãã§ãããããã«ãããã®å¯çæç©ã®çµ
è²»ã®ãããåé¢ã匷å¶çã«å¿ èŠã«ãªããäœãšãªã
ã°ãã®åŸã®æ®µéã«æŒããŠãããååšãããšãåå¿
ã®éè¡åã³çæç©ã®å質ã«ã€ããŠå§æ«ã«å°ãåé¡
ãçããããã§ããããããã€ãŠããã®ããã«å
äžå®¹åšæ³ã«æãéããããšãã§ããªãã殎å·ç¹èš±
第0011048å·ã«ããã°ïŒïŒïŒâãžãããããšãã«
ãšãŒãã«ã®éå ã¯æ°ŽçŽ ãµãå²æ°äžã§è²Žéå±è§Šåªã®
ååšäžä¿é²å€ãšããŠã®ææ©çªçŽ å¡©åºãæ·»å ããã«
éè¡ãããããã«ããèããçºç±çãªåå¿ãåå
ã«èª¿ç¯ããããšãã§ããªãããããŠäžååãªæž©åºŠ
å¶åŸ¡ã¯å質åã³åçãäœäžãããé»è²ã®å¯çæç©
ã®çæç©ããããããïŒïŒïŒâãžã¢ããâããšã
ã«ãšãŒãã«ã®ã¢ã·ã«åã®å ŽåïŒæ®Žå·ç¹èš±ç¬¬
0011048å·ïŒææã®ïŒâã¢ã·ã«ã¢ããâïŒâã¢ã
ãâããšãã«ãšãŒãã«ãçæããã°ããã§ãªãã
åå¿æ··åç©ã¯ãã®ã»ãã«åžžã«è¥å¹²ã®åå¿ããŠããª
ãåºçºææåã³äºã¢ã·ã«åååç©ãå«æãããé¡
䌌ã®éžæçåé¡ã¯éå çã¢ã«ãã«åäŸãã°ãã€ã
ç¹èš±åºé¡å ¬é第2745552å·å ¬å ±åã¯ã¹ã€ã¹ç¹èš±ç¬¬
310827å·æ现æžã«ç€ºãããæ¡ä»¶äžã«æŒããéå ç
ã¢ã«ãã«åã®å ŽååŸæ¥ååã«è§£æ±ºã§ããªãã€ãã æ¬çºæè ã¯é©ãã¹ãããšã«ãäžè¬åŒ(1) ïŒåŒäžR1ã¯ã¢ã«ãã«ïŒC1âC4ïŒåã¯ã¢ã«ã³ã
ã·ïŒC1âC4ïŒâã¢ã«ãã«ïŒC1âC4ïŒåºåã¯ããšã
ã«åºâããã¯å¡©çŽ âåã¯èçŽ ååãã¢ã«ãã«
ïŒC1âC4ïŒãã¢ã«ã³ãã·ïŒC1âC4ïŒãããªãã«ãªã
ã¡ãã«âãã«ã«ãã³é žã¢ããâãâNHâã¢ã«ã
ã«ïŒC1âC4ïŒãâïŒã¢ã«ãã«ïŒC1âC4ïŒïŒ2ãâSO2
âNH2ãâSO2âNHâã¢ã«ãã«ïŒC1âC4ïŒãâ
SO2âïŒã¢ã«ãã«ïŒC1âC4ïŒïŒ2ãã¢ã»ãã«ããã³
ãŸã€ã«ã¢ããâåã¯âNHâCOâã¢ã«ãã«ïŒC1
âC4ïŒåºã«ãã眮æãããŠããããšãã§ããâ
ããR2ã¯
ãžãããã¯ãã«ãã³ãŒã³ãšã¢ã«ã«ãªéå±ã¢ã«ã³ã¬
ãŒãåã¯âããšãã¬ãŒããšã®ïŒïŒïŒâãžãããã
ãšãã«ãšãŒãã«ãžã®åå¿ãééå±è§Šåªåã³è§Šåªé
ã®çªçŽ å«æææ©å¡©åºã®ååšäžã§ã®è©²ãšãŒãã«ã®
ïŒïŒïŒâãžã¢ããããšãã«ãšãŒãã«ãžã®éå ãïŒ
âã¢ã·ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«
ãžã®éžæçã¢ã·ã«ååã³ééå±è§Šåªåã³è§Šåªéã®
çªçŽ å«æææ©å¡©åºã®ååšäžã§ã®è©²ãšãŒãã«ã®ã¢ã«
ãããã§ã®éå çã¢ã«ãã«åã«ããïŒâã¢ã·ã«ã¢
ããâïŒâã¢ã«ãã«ã¢ããâããšãã«ãšãŒãã«ã®
補æ³ã§ããã ïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³ããã®ïŒâã¢
ã·ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«ã®è£œ
é ã¯ååçã«æç®äžå ¬ç¥ã§ããïŒæ¬§å·ç¹èš±ç¬¬
0011048å·ïŒã䜵ãããã§èšèŒã®ïŒïŒïŒâãžããã¯
ãã«ãã³ãŒã³ãšã¢ã«ã³ãŒã«ïŒã¢ã«ã«ãªæ¶²åã¯ã¢ã«
ã³ãŒã«ïŒã¢ã«ã«ãªæ°Žé žåç©ãšãåå¿ãããŠå¯Ÿå¿ã
ãïŒïŒïŒâãžãããããšãã«ãšãŒãã«ãšããå Žå
ïŒïŒïŒâãžãããããšããŒã«ã®çæãå®å šã«æé€
ããããšãã§ãããããã«ãããã®å¯çæç©ã®çµ
è²»ã®ãããåé¢ã匷å¶çã«å¿ èŠã«ãªããäœãšãªã
ã°ãã®åŸã®æ®µéã«æŒããŠãããååšãããšãåå¿
ã®éè¡åã³çæç©ã®å質ã«ã€ããŠå§æ«ã«å°ãåé¡
ãçããããã§ããããããã€ãŠããã®ããã«å
äžå®¹åšæ³ã«æãéããããšãã§ããªãã殎å·ç¹èš±
第0011048å·ã«ããã°ïŒïŒïŒâãžãããããšãã«
ãšãŒãã«ã®éå ã¯æ°ŽçŽ ãµãå²æ°äžã§è²Žéå±è§Šåªã®
ååšäžä¿é²å€ãšããŠã®ææ©çªçŽ å¡©åºãæ·»å ããã«
éè¡ãããããã«ããèããçºç±çãªåå¿ãåå
ã«èª¿ç¯ããããšãã§ããªãããããŠäžååãªæž©åºŠ
å¶åŸ¡ã¯å質åã³åçãäœäžãããé»è²ã®å¯çæç©
ã®çæç©ããããããïŒïŒïŒâãžã¢ããâããšã
ã«ãšãŒãã«ã®ã¢ã·ã«åã®å ŽåïŒæ®Žå·ç¹èš±ç¬¬
0011048å·ïŒææã®ïŒâã¢ã·ã«ã¢ããâïŒâã¢ã
ãâããšãã«ãšãŒãã«ãçæããã°ããã§ãªãã
åå¿æ··åç©ã¯ãã®ã»ãã«åžžã«è¥å¹²ã®åå¿ããŠããª
ãåºçºææåã³äºã¢ã·ã«åååç©ãå«æãããé¡
䌌ã®éžæçåé¡ã¯éå çã¢ã«ãã«åäŸãã°ãã€ã
ç¹èš±åºé¡å ¬é第2745552å·å ¬å ±åã¯ã¹ã€ã¹ç¹èš±ç¬¬
310827å·æ现æžã«ç€ºãããæ¡ä»¶äžã«æŒããéå ç
ã¢ã«ãã«åã®å ŽååŸæ¥ååã«è§£æ±ºã§ããªãã€ãã æ¬çºæè ã¯é©ãã¹ãããšã«ãäžè¬åŒ(1) ïŒåŒäžR1ã¯ã¢ã«ãã«ïŒC1âC4ïŒåã¯ã¢ã«ã³ã
ã·ïŒC1âC4ïŒâã¢ã«ãã«ïŒC1âC4ïŒåºåã¯ããšã
ã«åºâããã¯å¡©çŽ âåã¯èçŽ ååãã¢ã«ãã«
ïŒC1âC4ïŒãã¢ã«ã³ãã·ïŒC1âC4ïŒãããªãã«ãªã
ã¡ãã«âãã«ã«ãã³é žã¢ããâãâNHâã¢ã«ã
ã«ïŒC1âC4ïŒãâïŒã¢ã«ãã«ïŒC1âC4ïŒïŒ2ãâSO2
âNH2ãâSO2âNHâã¢ã«ãã«ïŒC1âC4ïŒãâ
SO2âïŒã¢ã«ãã«ïŒC1âC4ïŒïŒ2ãã¢ã»ãã«ããã³
ãŸã€ã«ã¢ããâåã¯âNHâCOâã¢ã«ãã«ïŒC1
âC4ïŒåºã«ãã眮æãããŠããããšãã§ããâ
ããR2ã¯
ãåŒãã¢ã«ãã«ïŒC1âC4ïŒåºããR3
ã¯ã¢ã«ãã«ïŒC1âC4ïŒåºãæå³ããïŒ
ã§ç€ºãããïŒâã¢ã·ã«ã¢ããâïŒâã¢ã«ãã«ã¢ã
ãâããšãã«ãšãŒãã«ãïŒïŒïŒâãžãããã¯ãã«
ãã³ãŒã³ããåºçºãããŠæ¬¡ã®æ§ã«ããŠæå©ã«ãã
ãŠé«åçã§è£œé ããããšãã§ããããšãèŠåºã
ããå³ã¡ïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³ã極æ§
ææ©æº¶å€äžã§ç¡æ°Žçã«äžè¬åŒ(2) R1âOMe (2) ïŒåŒäžR1ã¯åèšã®æå³ãæããMeã¯ã¢ã«ã«ãª
éå±ååã§ããïŒ ã§ç€ºãããã¢ã«ã«ãªéå±ã¢ã«ã³ã¬ãŒãåã¯âããš
ãã¬ãŒããšâ30âã100âã奜ãŸããã¯ïŒâã10
âã®æž©åºŠã§ãå Žåã«ãã䜿çšææ©æº¶å€ã«äŸåããŠ
å å§äžã«åå¿ãããŠãäžè¬åŒ(3) ïŒåŒäžR1ã¯åèšã®æå³ãæããïŒ ã§ç€ºãããïŒïŒïŒâãžãããããšãã«ãšãŒãã«ãš
ãããããäžéåé¢åŸåã¯å¥œãŸããã¯äžéåé¢ã
ãã«æ¥µæ§ææ©æº¶å€å¥œãŸããã¯å¡©çŽ 亀æãè¡ããã
åäžæº¶å€äžã§ãæ°ŽçŽ ãµãå²æ°äžã§åšæç³»ã®ç¬¬ïŒæ
ã®è²Žéå±è§ŠåªïŒã«ãããŠã ãçœéïŒåã³è§Šåªéã®
ææ©çªçŽ å¡©åºïŒä¿é²å€ïŒã®ååšäž50ã120â奜ãŸ
ããã¯50ã60âã®æž©åºŠã§å Žåã«ãã䜿çšææ©æº¶å€
ã«äŸåããŠå å§äžã察å¿ããïŒïŒïŒâãžã¢ããã
ãšãã«ãšãŒãã«ã«éå ãããããäžéåé¢åŸåã¯
奜ãŸããã¯äžéåé¢ããã«æ¥µæ§ææ©æº¶å€å¥œãŸãã
ã¯éå ãè¡ãããåäžæº¶å€äžã§â30âãïŒ90â奜
ãŸããã¯ïŒïŒãâ15âã®æž©åºŠã§ãå Žåã«ãã䜿çš
ææ©æº¶å€ã«äŸåããŠå å§äžãéžæçã«ã¢ã·ã«åã
ãŠäžè¬åŒ(4) ïŒåŒäžR1åã³R2ã¯åèšã®æå³ãæããïŒ ã§ç€ºããã察å¿ããïŒâã¢ã·ã«ã¢ããâïŒâã¢ã
ãâããšãã«ãšãŒãã«ãšãããããäžéåé¢åŸå
ã¯å¥œãŸããã¯äžéåé¢ããã«æ¥µæ§ææ©æº¶å€äžã§äž
è¬åŒ(5) ïŒåŒäžR3ã¯åèšã®æå³ãæããïŒ ã§ç€ºãããã¢ã«ãããã§æ°ŽçŽ ãµãå²æ°äžã«æŒãŠåš
æç³»ã®ç¬¬ïŒæã®è²Žéå±è§ŠåªïŒã«ãããŠã ãçœéïŒ
åã³è§Šåªéã®ææ©çªçŽ å¡©åºïŒä¿é²å€ïŒã®ååšäž30
ã120â奜ãŸããã¯50ã60âã®æž©åºŠã§ãå Žåã«ã
ã䜿çšææ©æº¶å€ã«äŸåããŠå å§äžãéžæçã«ã¢ã«
ãã«åããŠäžèšäžè¬åŒ(1)ã®ååç©ãšããã é©ãã¹ãçµæã«é¢ããåã ã®æ®µéã«é¢ããŠã
ïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³ãã¢ã«ã«ãªéå±
æ°Žé žåç©ã®ä»£ãã«ã¢ã«ã«ãªéå±ã¢ã«ã³ã¬ãŒãåã¯
âããšãã¬ãŒããšåå¿ãããå ŽåïŒïŒïŒâãžãã
ãããšãã«åºã®æãŸãããªãçæãå®å šã«é¿ãã
ããã°ããã§ãªãåããã«ç¶ãïŒïŒïŒâãžããã
ããšãã«ãšãŒãã«ã®éå ã®å Žåã®ïŒïŒïŒâãžã¢ã
ãããšãã«ãšãŒãã«ã®åçãèããæ¹åãããã
ãšãé©ãã¹ãããšãšèããªããã°ãªããªãã ïŒïŒïŒâãžãããããšãã«ãšãŒãã«ã®æ¥è§Šéå
ã®å Žåã觊åªéã®ææ©çªçŽ å¡©åºäŸãã°ããªãšãã«
ã¢ãã³ã®æ·»å ã¯çºç±åå¿ã®äžæ§ãªé²è¡ãä¿èšŒãã
ããã«ãã€ãŠå質åã³åçã®åäžãããããããš
ã¯é©ãã¹ãããšãšèããªããã°ãªããªãã ïŒâã¢ã·ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒ
ãã«ã®ç®çååç©ãžã®éå çã¢ã«ãã«åã«é¢ã
ãŠã觊åªéã®ææ©çªçŽ å¡©åºäŸãã°äœçŽããªã¢ã«ã
ã«ã¢ãã³ã®ååšäžã§ã®è²Žéå±è§Šåªã®äœ¿çšã¯é«ã転
åçãããè¯å¥œãªéžæçåã³é«åçãçãããã
ããšã¯é©ãã¹ãããšã§ãã€ãã æ¬æ¹æ³ã®å®æœã«é¢ããŠæ¬¡ã®éã詳述ããïŒ æ¥µæ§ææ©æº¶å€äŸãã°ïŒâïŒåã®ççŽ ååãæã
ãçŽéåã¯æåãã¢ã«ã«ããŒã«äŸãã°ã¡ã¿ããŒã«
åã¯ãšã¿ããŒã«åã¯çŽéåã¯æåãã¢ã«ãã«
ïŒC1âC4ïŒã¢ã»ããŒãäŸãã°ãšãã«ã¢ã»ããŒãã
ãããã«ã¢ã»ããŒããïœâããã«ã¢ã»ããŒãåã¯
ã€ãœâããã«ã¢ã»ããŒãåã¯ã°ãªã³ãŒã«åã¯ã°ãª
ã³ãŒã«ãšãŒãã«äŸãã°ãžãšãã¬ã³ã°ãªã³ãŒã«åã¯
ã¡ãã«ã°ãªã³ãŒã«äžã®ïŒïŒïŒâãžãããã¯ãã«ã
ã³ãŒã³ã®æº¶æ¶²ã«ãåèšã®ææ©æº¶å€æå©ã«ã¯ïŒïŒïŒ
âãžãããã¯ãã«ãã³ãŒã³ã溶解ãããŠäœ¿çšãã
åäžæº¶å€äžã«æº¶ãããã¢ã«ã«ãªéå±ã¢ã«ã³ã¬ãŒã
åã¯âããšãã¬ãŒãã®æº¶æ¶²ãäžèšã®æž©åºŠç¯å²å 奜
ãŸããã¯ïŒã10âã®æž©åºŠç¯å²å ã§æ»Žå ããããšã
æå©ã§ãããäž¡åå¿æåã¯çã¢ã«éã§äœ¿çšãã
ãã 次ã®æ®µéïŒãã³ãŒã³æ žã®ïŒïŒïŒâäœã«æŒããäž¡
ãããåºã®éå ïŒã®å Žååšæç³»ã®ç¬¬ïŒæã®è²Žéå±
觊åªãšããŠäŸãã°çœéãé žåçœéåã¯ãã©ãžãŠã
ã倫ã é©åœãªæ äœææäŸãã°ãçåã¯ç¡«é žããªãŠ
ã äžã§äœ¿çšããããã®é觊åªã¯æå©ã«ã¯ïŒïŒïŒâ
ãžãããããšãã«ãšãŒãã«ïŒã¢ã«åœã0.5â10ïœ
奜ãŸããã¯ïŒâïŒïœã®éã§äœ¿çšãããããã®å Žå
åæ§ã«è§Šåªéã§äœ¿çšãããææ©çªçŽ å¡©åºãšããŠã¯
äŸãã°è³éŠæå¡©åºäŸãã°ããªãžã³åã¯ãããªã³å
ã¯è€çŽ ç°åŒå¡©åºäŸãã°ã¢ã«ããªã³åã¯ããªã¢ã«ã
ã«ïŒC1âC4ïŒã¢ãã³äŸãã°ããªãšãã«ã¢ãã³å
ã¯ããªâïœâããã«ã¢ãã³åã¯ãžã¢ã«ãã«ïŒC1
âC4ïŒã¢ãã³äŸãã°ãžã€ãœãããã«ã¢ãã³åã¯
æŽã«ã¢ã«ãã«æ®åºäžã«ïŒâïŒåã®ççŽ ååãæã
ãããªã¢ã«ãããŒã«ã¢ãã³äŸãã°ããªãšã¿ããŒã«
ã¢ãã³ãèæ ®ããããã®éææ©çªçŽ å¡©åºã¯æå©ã«
ã¯äœ¿çšãããïŒïŒïŒâãžãããããšãã«ãšãŒãã«
ã«å¯ŸãïŒãïŒééïŒ å¥œãŸããã¯ïŒã1.5ééïŒ ã®
éã§äœ¿çšããããã€ãã§ãªããããã®åå¿æ®µéã§
ã¯ç¬¬äžåå¿æ®µéïŒå¡©çŽ 亀æïŒã®å Žåãšåã極æ§æ
æ©æº¶å€ã䜿çšãããã 第äžåå¿æ®µéã§èµ·ããããã³ãŒã³æ žã®ïŒâäœã«
ååšããã¢ããåºã®éžæçã¢ã·ã«åã¯åæ§ã«ç¬¬äž
段éïŒå¡©çŽ 亀æïŒã«æŒãŠäœ¿çšãããã®ãšåã極æ§
ææ©æº¶å€äžã§éè¡ããããã¢ã·ã«åå€ãšããŠã¯äž
è¬åŒ ïŒã¢ã«ãã«ïŒC1âC4ïŒCOïŒ2Oå㯠ã¢ã«ãã«ïŒC1âC4ïŒâCOâããã²ã³ ïŒåŒäžããã²ã³ã¯å¥œãŸããã¯å¡©çŽ ååãæå³ã
ãïŒ ã§ç€ºãããã«ã«ãã³é žç¡æ°Žç©åã¯ã«ã«ãã³é žãã
ã²ã³åç©ãèæ ®ãããã åæ§ã«ç¬¬ååå¿æ®µéïŒãã³ãŒã³æ žã®ïŒâäœã«åš
ãã¢ããåºã®éžæçã¢ã«ãã«åïŒã¯ç¬¬äžåå¿æ®µé
ã§äœ¿çšããã極æ§ææ©æº¶å€äžã§å®æœãããã ãã®å Žå䜿çšããã貎éå±è§Šåªåã³è§Šåªéã§äœ¿
çšãããææ©çªçŽ å¡©åºã«é¢ããŠã¯ãåèšã®ïŒïŒïŒ
âãžãããããšãã«ãšãŒãã«ã®éå ã®å Žåã«èšèŒ
ã®è§Šåªåã³ææ©çªçŽ å¡©åºã®å Žåãšåããã®ãèæ ®
ãããããã®å Žå貎éå±è§Šåªã¯æå©ã«ã¯ïŒâã¢ã·
ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«ïŒã¢ã«
åœãïŒâ10ïœå¥œãŸããã¯ïŒâïŒïœã®éã§äœ¿çšãã
ãããã®å Žåææ©å¡©åºã¯æå©ã«ã¯äœ¿çšïŒâã¢ã·ã«
ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«ã«å¯ŸãïŒ
ã10é»éïŒ å¥œãŸããã¯ïŒãïŒééïŒ ã®éã§äœ¿çšã
ããã ã¢ã«ãããã¯æå©ã«ã¯ãäžèšäžè¬åŒ(4)ã®ååç©
ã«å¯Ÿã20â80ã¢ã«ïŒ 奜ãŸããã¯25ã¢ã«ïŒ ã®éå°ã§
䜿çšãããã ïŒâã¢ã·ã«ã¢ããâïŒâã¢ã«ãã«ã¢ããâããš
ãã«ãšãŒãã«ã¯åæ£ææã§è£œé ããããã®äŸ¡å€ã®
é«ãåé§ç©è³ªã§ããïŒãã«ã®ãŒç¹èš±ç¬¬634032å·æ
现æžïŒã äŸ ïŒ ã¡ãã«ã°ãªã³ãŒã«407ïœäžãããªãŠã ã¡ãã«ã°
ãªã³ã¬ãŒã98ïœïŒïŒã¢ã«ïŒã®æº¶æ¶²ã«ã¡ãã«ã°ãªã³
ãŒã«482ïœäžïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³
202.6ïœïŒïŒã¢ã«ïŒãïŒâ10âã§1/2æé以å ã«æ»Ž
å ãããåŒãç¶ããŠïŒæéåŸæ¹æããæ²æ®¿ããå¡©
åãããªãŠã ããå¥ããã液ã«ããªãšãã«ã¢ãã³
12.6ïœåã³è§ŠåªïŒçäžã®ãã©ãžãŠã ïŒïŒ ïŒïŒïœã
å ãããæ··åç©ã50â60âåã³10â30ããŒã«ã®æ°Ž
çŽ å§ã§æ°ŽçŽ åããã觊åªããå¥ãã溶液äžã®ïŒâ
ãžã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ã®å«æ
éãäºç¡é žæ»Žå®ã«ãã枬å®ããïŒåççè«å€ã®94
ïŒ ïŒãã¡ãã«ã°ãªã³ãŒã«åã³æ°Žãæžå§ïŒ22mmïŒèž
çã«ããé€å»ããæ®çç©ãã¡ã¿ããŒã«735ïœäžã«
溶解ãããããã®åŸã®æº¶æ¶²ã«é žåãã°ãã·ãŠã
20.2ïœïŒ0.5ã¢ã«ïŒãå ããã次ã«ïŒâ15âã§ç¡
æ°Žé ¢é ž93.9ïœïŒ0.92ã¢ã«ïŒãïŒ 1/2æé以å ã«æ»Ž
å ãããã®éïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâ
βâã¡ããã·ãšããã·ãã³ãŒã³ãé«ãéžæçã§åŸ
ããããçæç©ååžãHPLCâåæïŒãHPLCãâ
é«å§æ¶²äœã¯ãããã°ã©ãã€ãŒïŒã«ãã枬å®ããïŒ ïŒïŒïŒâãžã¢ããâαâã¡ããã·ãšããã·ãã³
ãŒã³ ïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ãã
ã·ãšããã·ãã³ãŒã³ 89ïŒ ïŒïŒïŒâãžã¢ã»ãã«ã¢ããâβâã¡ããã·ãšã
ãã·ãã³ãŒã³ ïŒïŒ æ··åç©ïŒïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ïŒâ§0.5ã¢ã«ïŒ665.7ïœ
ã掻æ§ç12.5ïœåã³ããããå12.5ïœã§æž æŸå
ããããªãšãã«ã¢ãã³6.3ïœåã³è§ŠåªïŒçäžãã©
ãžãŠã ïŒïŒ ïŒ2.5ïœãå ãããæ··åç©ã«ã¢ã»ãã¢
ã«ããã26.6ïœïŒ0.6ã¢ã«ïŒãå ãã50â60âå
ã³40â80ããŒã«ã®æ°ŽçŽ å§ã§æ°ŽçŽ åããã觊åªãã
åããã¡ã¿ããŒã«ã倧æ°å§ã§çåºããçæç©ãæ°Ž
200ïœã«ããæ²æ®¿ã«ããåé¢ããã ã¢ã«ãã«åã®éžæ床ïŒHPLCâåæïŒïŒ ã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ããã·ãš
ããã·ãã³ãŒã³ 4.6ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ 93ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ 2.4ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ã®åçã¯äœ¿çšïŒïŒïŒâ
ãžãããã¯ãã«ãã³ãŒã³ã«å¯Ÿãçè«å€ã®72ïŒ ã§ã
ããèç¹72â73âãããªãšãã«ã¢ãã³12.6ïœã®ä»£
ãã«ãžã€ãœãããã«ã¢ãã³12.6ïœã䜿çšããããŠ
ãã®ä»ã¯åèšãšåæ§ã«å®æœããã°ç®ççæç©ã®å
çåã³çµæã«é¢ããŠåäžã®çµæãåŸãããã ããªãšãã«ã¢ãã³12.6ïœã®ä»£ãã«ããªâïœâã
ãã«ã¢ãã³12.6ïœã䜿çšããããŠãã®ä»ã¯åèšãš
åæ§ã«å®æœããã°ç®ççæç©ã®åçåã³çµæã«é¢
ããŠåäžã®çµæãåŸãããã äŸ ïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ããâïŒâããããª
ãã«ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ïŒäŸ
ïŒãšåæ§ã«è£œé ïŒ119ïœïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã掻æ§
ç6.3ïœåã³ããããå6.3ïœã§æž æŸåããããã®
åŸã液ã«ããªãšãã«ã¢ãã³6.3ïœåã³è§ŠåªïŒçäž
ãã©ãžãŠã ïŒïŒ ïŒ2.5ïœãå ãããåŒãç¶ããŠã¢
ã»ãã¢ã«ããã33.3ïœïŒ0.75ã¢ã«ïŒã®ååšäžïŒæ
é以å ã«50â60âåã³40â80ããŒã«ã®æ°ŽçŽ å§ã§æ°Ž
çŽ åãããåå¿æº¶æ¶²ãã觊åªãåé¢ããåŸãçªçŽ
ã®äžã§ã¡ã¿ããŒã«åã³æ°Žãèžçã«ãã€ãŠé€å»ã
ãã次ã«180ïœã®æ°Žãæ·»å ããããšã«ãã€ãŠçæ
ç©ãæ²æ®¿ãããåžåŒãéãã20ïŒ é£å¡©æº¶æ¶²100ïœ
ã§æŽæµãããïŒâãšãã«ã¢ããâïŒâããããªã
ã«ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ã®åç
ã¯ã䜿çšããïŒâã¢ããâïŒâããããªãã«ã¢ã
ãâβâã¡ããã·ãšããã·ãã³ãŒã³ã«å¯Ÿããçè«
å€ã®84ïŒ ã§ããã 也ç¥è©Šæã®èç¹ïŒ78â80âã ã¢ã«ãã«åã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ããâïŒâããããªãã«ã¢ããâβâã¡
ããã·ãšããã·ãã³ãŒã³ ïŒïŒ ïŒâãšãã«ã¢ããâïŒâããããªãã«ã¢ããâ
βâã¡ããã·ãšããã·ãã³ãŒã³ 93.5ïŒ ïŒâãžãšãã«ã¢ããâïŒâããããªãã«ã¢ãã
âβâã¡ããã·ãšããã·ãã³ãŒã³ 2.5ïŒ äŸ ïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ããã¢ããœãŒã«ïŒäŸïŒãšåæ§ã«è£œé ïŒ90ïœ
ïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã«ããªãšãã«ã¢ãã³6.3ïœåã³
觊åªïŒçäžãã©ãžãŠã ïŒïŒ ïŒ2.5ïœãå ãããæ··
åç©ãã¢ã»ãã¢ã«ããã26.4ïœïŒ0.6ã¢ã«ïŒã®å
åšäž40â60ããŒã«ã®æ°ŽçŽ å§åã³50â60âã®æž©åºŠã§
ïŒæé以å ã«æ°ŽçŽ åããã觊åªã®ãå¥åŸã¡ã¿ããŒ
ã«ãã¡ã¿ããŒã«ãèžçã«ãã€ãŠé€å»ããçæç©ã
æ°Ž200ïœã®æ·»å ã«ããæ²æ®¿ããããïŒâã¢ã»ãã«
ã¢ããâïŒâãšãã«ã¢ããã¢ããœãŒã«ã®åçã¯ç
è«å€ã®86ïŒ ã§ãããèç¹94â102âã ã¢ã«ãã«åã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããã¢ããœãŒã«
ïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâã¢ã
ãœãŒã« 96ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâã¢
ããœãŒã« ïŒïŒ äŸ ïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ãããžããšãã«ãšãŒãã«ïŒäŸïŒãšåæ§ã«è£œé ïŒ
121ïœïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã«ããªãšãã«ã¢ãã³6.3
ïœåã³è§ŠåªïŒçäžãã©ãžãŠã ïŒïŒ ïŒ2.5ïœãå ã
ããæ··åç©ãã¢ã»ãã¢ã«ããã28.6ïœïŒ0.65ã¢
ã«ïŒã®ååšäžïŒæé50â60âåã³40â80ããŒã«ã®
æ°ŽçŽ å§ã§æ°ŽçŽ åããã觊åªã®ãå¥åŸæº¶å€ãèžçã«
ããé€å»ããçæç©ãæ°Ž200ïœã®æ·»å ã«ããæ²æ®¿
ãããã ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ãããžããš
ãã«ãšãŒãã«ã®åçã¯çè«å€ã®88ïŒ ã§ããã èç¹109â110âã ã¢ã«ãã«åã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâãžããšãã«
ãšãŒãã« ïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâãžã
ãšãã«ãšãŒãã« 89ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâãž
ããšãã«ãšãŒãã« ïŒïŒ äŸ ïŒïŒéå çã¢ã«ãã«åã«é¢ããæ¯èŒäŸïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ïŒäŸïŒã«
ãã補é ïŒ112ïœïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã60ïŒ ã©ããŒ
ããã±ã«4.3ïœåã³ã¢ã»ãã¢ã«ããã28.6ïœïŒ0.65
ã¢ã«ïŒã®ååšäž60â70âåã³40â80ããŒã«ã®æ°ŽçŽ
å§ã§æ°ŽçŽ åããã觊åªã®ãå¥åŸçæç©ãæ°Ž200ïœ
ã®æ·»å ã«ããæ²æ®¿ãããã ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ã®åçã¯çè«å€ã®71ïŒ
ã§ããã åå¿ã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ãã
ã·ãšããã·ãã³ãŒã³ 15ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ 77ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ ïŒïŒ äŸ ïŒïŒéå çã¢ã«ãã«åã«é¢ããæ¯èŒäŸïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ïŒ0.5ã¢
ã«ïŒã®æº¶æ¶²ããããªãšãã«ã¢ãã³6.3ïœãããã±
ã«âããããåâ觊åªïŒRCH55ïŒïŒã¡ãŒã«ãŒ
RuhrchemieïŒïŒïœåã³ã¢ã»ãã¢ã«ããã33ïœ
ïŒ0.75ã¢ã«ïŒãïŒ ïŒ1/2æéã§60â85âåã³40â
80ããŒã«ã®æ°ŽçŽ å§ã«æŒãŠæ°ŽçŽ åããã觊åªã®ãå¥
åŸæº¶å€ãèžçã«ãã€ãŠé€å»ããçæç©ãæ°Ž200ïœ
ã®æ·»å ã«ããæ²æ®¿ãããã ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ã®åçã¯çè«å€ã®11ïŒ
ã§ããã éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ãã
ã·ãšããã·ãã³ãŒã³ 68ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ 14ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ 18ïŒ äŸ ïŒïŒæ¯èŒäŸïŒ 溶èããïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³213
ïœãã¡ã¿ããŒã«632ïœã«å°å ¥ããæ¹æããªãã溶
解ããããæ¹æãããŠãã溶液ã«ããã圢ã®åºåœ¢
æ°Žé žåãããªãŠã 42ïœããåå¿æº¶æ¶²ãå ç±ãããŠ
éæµäžã§ç·©ããã«æ²žéš°ããæ§ã«ãæ·»å ãããæ°Žé ž
åãããªãŠã å šéã®æ·»å åŸïŒæééæµäžå ç±ã
ããåŒãç¶ããŠå·åŽããïŒæ®Žå·ç¹èš±ç¬¬0011048å·
æ现æžã®äŸïŒã®åå¿æ®µéïŒåç §ïŒã ãã®æ§ã«åŸãããæžæ¿æ¶²ïŒïŒïŒïŒâãžãããã¢
ããœãŒã«ãå«æïŒããã©ãžãŠã ïŒïŒ ïŒçäžã§60â
ã«æŒãŠæ°ŽçŽ åãããã®éïŒïŒïŒâãžã¢ããã¢ããœ
ãŒã«ã®åçã¯çè«å€ã®95.2ïŒ ã«çžåœããã äŸ ïŒïŒæ¯èŒäŸïŒ äŸïŒãšåæ§ã«ãããªãŠã ã¡ãã¬ãŒãã®ã¡ã¿ããŒ
ã«æ§æº¶æ¶²ã«1/2æé以å ã«ïŒâ10âã§ïŒïŒïŒâãž
ãããã¯ãã«ãã³ãŒã³ã®ã¡ã¿ããŒã«æ§æº¶æ¶²ã滎å
ããããŠïŒæéåŸæ¹æããŠè£œé ãããïŒïŒïŒâãž
ãããã¢ããœãŒã«ãå«æããæžæ¿æ¶²ã«45ïœã®æ°Ž
ïŒå³ã¡æ®Žå·ç¹èš±ç¬¬0011048å·æ现æžã®äŸïŒã«å¥æ³ãš
ããŠæèšãããŠãã50ïŒ ã®èæ§ãœãŒã氎溶液ã®æ·»
å ãçšããå Žåã«ããã®äŸïŒã®åå¿æ®µéïŒã«åŸã
åå¿æ··åç©äžã«ååšãããšæãããéã®æ°ŽïŒãå
ãããäŸïŒãšåæ§ã«éè¡ãããæ¥è§Šéå åŸïŒïŒïŒ
âãžã¢ããã¢ããœãŒã«ã®åçã¯çè«å€ã®87.6ïŒ ã
åŸãããã«éãã¬ã äŸ ïŒ ã¡ã¿ããŒã«440éšäžïŒïŒïŒâãžãããã¯ãã«ã
ã³ãŒã³202.5ïœã®æžæ¿æ¶²ã«å®€æž©ã§60å以å ã«ã¡ã¿
ããŒã«äžãããªãŠã ã¡ãã¬ãŒãã®30ïŒ æº¶æ¶²189.1
ïœãæµãããã®é枩床ã¯55â60âã«é«ãŸããã¡ã¿
ããŒã«160éšåã³ããªãšãã«ã¢ãã³ïŒéšã®æ·»å åŸ
ãã©ãžãŠã ïŒïŒ ïŒçäžã§60âã«æŒãŠæ°ŽçŽ åããã
ïŒïŒïŒâãžã¢ããã¢ããœãŒã«ã®åçã¯çè«å€ã®
98.0ïŒ ã§ããã
ãâããšãã«ãšãŒãã«ãïŒïŒïŒâãžãããã¯ãã«
ãã³ãŒã³ããåºçºãããŠæ¬¡ã®æ§ã«ããŠæå©ã«ãã
ãŠé«åçã§è£œé ããããšãã§ããããšãèŠåºã
ããå³ã¡ïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³ã極æ§
ææ©æº¶å€äžã§ç¡æ°Žçã«äžè¬åŒ(2) R1âOMe (2) ïŒåŒäžR1ã¯åèšã®æå³ãæããMeã¯ã¢ã«ã«ãª
éå±ååã§ããïŒ ã§ç€ºãããã¢ã«ã«ãªéå±ã¢ã«ã³ã¬ãŒãåã¯âããš
ãã¬ãŒããšâ30âã100âã奜ãŸããã¯ïŒâã10
âã®æž©åºŠã§ãå Žåã«ãã䜿çšææ©æº¶å€ã«äŸåããŠ
å å§äžã«åå¿ãããŠãäžè¬åŒ(3) ïŒåŒäžR1ã¯åèšã®æå³ãæããïŒ ã§ç€ºãããïŒïŒïŒâãžãããããšãã«ãšãŒãã«ãš
ãããããäžéåé¢åŸåã¯å¥œãŸããã¯äžéåé¢ã
ãã«æ¥µæ§ææ©æº¶å€å¥œãŸããã¯å¡©çŽ 亀æãè¡ããã
åäžæº¶å€äžã§ãæ°ŽçŽ ãµãå²æ°äžã§åšæç³»ã®ç¬¬ïŒæ
ã®è²Žéå±è§ŠåªïŒã«ãããŠã ãçœéïŒåã³è§Šåªéã®
ææ©çªçŽ å¡©åºïŒä¿é²å€ïŒã®ååšäž50ã120â奜ãŸ
ããã¯50ã60âã®æž©åºŠã§å Žåã«ãã䜿çšææ©æº¶å€
ã«äŸåããŠå å§äžã察å¿ããïŒïŒïŒâãžã¢ããã
ãšãã«ãšãŒãã«ã«éå ãããããäžéåé¢åŸåã¯
奜ãŸããã¯äžéåé¢ããã«æ¥µæ§ææ©æº¶å€å¥œãŸãã
ã¯éå ãè¡ãããåäžæº¶å€äžã§â30âãïŒ90â奜
ãŸããã¯ïŒïŒãâ15âã®æž©åºŠã§ãå Žåã«ãã䜿çš
ææ©æº¶å€ã«äŸåããŠå å§äžãéžæçã«ã¢ã·ã«åã
ãŠäžè¬åŒ(4) ïŒåŒäžR1åã³R2ã¯åèšã®æå³ãæããïŒ ã§ç€ºããã察å¿ããïŒâã¢ã·ã«ã¢ããâïŒâã¢ã
ãâããšãã«ãšãŒãã«ãšãããããäžéåé¢åŸå
ã¯å¥œãŸããã¯äžéåé¢ããã«æ¥µæ§ææ©æº¶å€äžã§äž
è¬åŒ(5) ïŒåŒäžR3ã¯åèšã®æå³ãæããïŒ ã§ç€ºãããã¢ã«ãããã§æ°ŽçŽ ãµãå²æ°äžã«æŒãŠåš
æç³»ã®ç¬¬ïŒæã®è²Žéå±è§ŠåªïŒã«ãããŠã ãçœéïŒ
åã³è§Šåªéã®ææ©çªçŽ å¡©åºïŒä¿é²å€ïŒã®ååšäž30
ã120â奜ãŸããã¯50ã60âã®æž©åºŠã§ãå Žåã«ã
ã䜿çšææ©æº¶å€ã«äŸåããŠå å§äžãéžæçã«ã¢ã«
ãã«åããŠäžèšäžè¬åŒ(1)ã®ååç©ãšããã é©ãã¹ãçµæã«é¢ããåã ã®æ®µéã«é¢ããŠã
ïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³ãã¢ã«ã«ãªéå±
æ°Žé žåç©ã®ä»£ãã«ã¢ã«ã«ãªéå±ã¢ã«ã³ã¬ãŒãåã¯
âããšãã¬ãŒããšåå¿ãããå ŽåïŒïŒïŒâãžãã
ãããšãã«åºã®æãŸãããªãçæãå®å šã«é¿ãã
ããã°ããã§ãªãåããã«ç¶ãïŒïŒïŒâãžããã
ããšãã«ãšãŒãã«ã®éå ã®å Žåã®ïŒïŒïŒâãžã¢ã
ãããšãã«ãšãŒãã«ã®åçãèããæ¹åãããã
ãšãé©ãã¹ãããšãšèããªããã°ãªããªãã ïŒïŒïŒâãžãããããšãã«ãšãŒãã«ã®æ¥è§Šéå
ã®å Žåã觊åªéã®ææ©çªçŽ å¡©åºäŸãã°ããªãšãã«
ã¢ãã³ã®æ·»å ã¯çºç±åå¿ã®äžæ§ãªé²è¡ãä¿èšŒãã
ããã«ãã€ãŠå質åã³åçã®åäžãããããããš
ã¯é©ãã¹ãããšãšèããªããã°ãªããªãã ïŒâã¢ã·ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒ
ãã«ã®ç®çååç©ãžã®éå çã¢ã«ãã«åã«é¢ã
ãŠã觊åªéã®ææ©çªçŽ å¡©åºäŸãã°äœçŽããªã¢ã«ã
ã«ã¢ãã³ã®ååšäžã§ã®è²Žéå±è§Šåªã®äœ¿çšã¯é«ã転
åçãããè¯å¥œãªéžæçåã³é«åçãçãããã
ããšã¯é©ãã¹ãããšã§ãã€ãã æ¬æ¹æ³ã®å®æœã«é¢ããŠæ¬¡ã®éã詳述ããïŒ æ¥µæ§ææ©æº¶å€äŸãã°ïŒâïŒåã®ççŽ ååãæã
ãçŽéåã¯æåãã¢ã«ã«ããŒã«äŸãã°ã¡ã¿ããŒã«
åã¯ãšã¿ããŒã«åã¯çŽéåã¯æåãã¢ã«ãã«
ïŒC1âC4ïŒã¢ã»ããŒãäŸãã°ãšãã«ã¢ã»ããŒãã
ãããã«ã¢ã»ããŒããïœâããã«ã¢ã»ããŒãåã¯
ã€ãœâããã«ã¢ã»ããŒãåã¯ã°ãªã³ãŒã«åã¯ã°ãª
ã³ãŒã«ãšãŒãã«äŸãã°ãžãšãã¬ã³ã°ãªã³ãŒã«åã¯
ã¡ãã«ã°ãªã³ãŒã«äžã®ïŒïŒïŒâãžãããã¯ãã«ã
ã³ãŒã³ã®æº¶æ¶²ã«ãåèšã®ææ©æº¶å€æå©ã«ã¯ïŒïŒïŒ
âãžãããã¯ãã«ãã³ãŒã³ã溶解ãããŠäœ¿çšãã
åäžæº¶å€äžã«æº¶ãããã¢ã«ã«ãªéå±ã¢ã«ã³ã¬ãŒã
åã¯âããšãã¬ãŒãã®æº¶æ¶²ãäžèšã®æž©åºŠç¯å²å 奜
ãŸããã¯ïŒã10âã®æž©åºŠç¯å²å ã§æ»Žå ããããšã
æå©ã§ãããäž¡åå¿æåã¯çã¢ã«éã§äœ¿çšãã
ãã 次ã®æ®µéïŒãã³ãŒã³æ žã®ïŒïŒïŒâäœã«æŒããäž¡
ãããåºã®éå ïŒã®å Žååšæç³»ã®ç¬¬ïŒæã®è²Žéå±
觊åªãšããŠäŸãã°çœéãé žåçœéåã¯ãã©ãžãŠã
ã倫ã é©åœãªæ äœææäŸãã°ãçåã¯ç¡«é žããªãŠ
ã äžã§äœ¿çšããããã®é觊åªã¯æå©ã«ã¯ïŒïŒïŒâ
ãžãããããšãã«ãšãŒãã«ïŒã¢ã«åœã0.5â10ïœ
奜ãŸããã¯ïŒâïŒïœã®éã§äœ¿çšãããããã®å Žå
åæ§ã«è§Šåªéã§äœ¿çšãããææ©çªçŽ å¡©åºãšããŠã¯
äŸãã°è³éŠæå¡©åºäŸãã°ããªãžã³åã¯ãããªã³å
ã¯è€çŽ ç°åŒå¡©åºäŸãã°ã¢ã«ããªã³åã¯ããªã¢ã«ã
ã«ïŒC1âC4ïŒã¢ãã³äŸãã°ããªãšãã«ã¢ãã³å
ã¯ããªâïœâããã«ã¢ãã³åã¯ãžã¢ã«ãã«ïŒC1
âC4ïŒã¢ãã³äŸãã°ãžã€ãœãããã«ã¢ãã³åã¯
æŽã«ã¢ã«ãã«æ®åºäžã«ïŒâïŒåã®ççŽ ååãæã
ãããªã¢ã«ãããŒã«ã¢ãã³äŸãã°ããªãšã¿ããŒã«
ã¢ãã³ãèæ ®ããããã®éææ©çªçŽ å¡©åºã¯æå©ã«
ã¯äœ¿çšãããïŒïŒïŒâãžãããããšãã«ãšãŒãã«
ã«å¯ŸãïŒãïŒééïŒ å¥œãŸããã¯ïŒã1.5ééïŒ ã®
éã§äœ¿çšããããã€ãã§ãªããããã®åå¿æ®µéã§
ã¯ç¬¬äžåå¿æ®µéïŒå¡©çŽ 亀æïŒã®å Žåãšåã極æ§æ
æ©æº¶å€ã䜿çšãããã 第äžåå¿æ®µéã§èµ·ããããã³ãŒã³æ žã®ïŒâäœã«
ååšããã¢ããåºã®éžæçã¢ã·ã«åã¯åæ§ã«ç¬¬äž
段éïŒå¡©çŽ 亀æïŒã«æŒãŠäœ¿çšãããã®ãšåã極æ§
ææ©æº¶å€äžã§éè¡ããããã¢ã·ã«åå€ãšããŠã¯äž
è¬åŒ ïŒã¢ã«ãã«ïŒC1âC4ïŒCOïŒ2Oå㯠ã¢ã«ãã«ïŒC1âC4ïŒâCOâããã²ã³ ïŒåŒäžããã²ã³ã¯å¥œãŸããã¯å¡©çŽ ååãæå³ã
ãïŒ ã§ç€ºãããã«ã«ãã³é žç¡æ°Žç©åã¯ã«ã«ãã³é žãã
ã²ã³åç©ãèæ ®ãããã åæ§ã«ç¬¬ååå¿æ®µéïŒãã³ãŒã³æ žã®ïŒâäœã«åš
ãã¢ããåºã®éžæçã¢ã«ãã«åïŒã¯ç¬¬äžåå¿æ®µé
ã§äœ¿çšããã極æ§ææ©æº¶å€äžã§å®æœãããã ãã®å Žå䜿çšããã貎éå±è§Šåªåã³è§Šåªéã§äœ¿
çšãããææ©çªçŽ å¡©åºã«é¢ããŠã¯ãåèšã®ïŒïŒïŒ
âãžãããããšãã«ãšãŒãã«ã®éå ã®å Žåã«èšèŒ
ã®è§Šåªåã³ææ©çªçŽ å¡©åºã®å Žåãšåããã®ãèæ ®
ãããããã®å Žå貎éå±è§Šåªã¯æå©ã«ã¯ïŒâã¢ã·
ã«ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«ïŒã¢ã«
åœãïŒâ10ïœå¥œãŸããã¯ïŒâïŒïœã®éã§äœ¿çšãã
ãããã®å Žåææ©å¡©åºã¯æå©ã«ã¯äœ¿çšïŒâã¢ã·ã«
ã¢ããâïŒâã¢ããâããšãã«ãšãŒãã«ã«å¯ŸãïŒ
ã10é»éïŒ å¥œãŸããã¯ïŒãïŒééïŒ ã®éã§äœ¿çšã
ããã ã¢ã«ãããã¯æå©ã«ã¯ãäžèšäžè¬åŒ(4)ã®ååç©
ã«å¯Ÿã20â80ã¢ã«ïŒ 奜ãŸããã¯25ã¢ã«ïŒ ã®éå°ã§
䜿çšãããã ïŒâã¢ã·ã«ã¢ããâïŒâã¢ã«ãã«ã¢ããâããš
ãã«ãšãŒãã«ã¯åæ£ææã§è£œé ããããã®äŸ¡å€ã®
é«ãåé§ç©è³ªã§ããïŒãã«ã®ãŒç¹èš±ç¬¬634032å·æ
现æžïŒã äŸ ïŒ ã¡ãã«ã°ãªã³ãŒã«407ïœäžãããªãŠã ã¡ãã«ã°
ãªã³ã¬ãŒã98ïœïŒïŒã¢ã«ïŒã®æº¶æ¶²ã«ã¡ãã«ã°ãªã³
ãŒã«482ïœäžïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³
202.6ïœïŒïŒã¢ã«ïŒãïŒâ10âã§1/2æé以å ã«æ»Ž
å ãããåŒãç¶ããŠïŒæéåŸæ¹æããæ²æ®¿ããå¡©
åãããªãŠã ããå¥ããã液ã«ããªãšãã«ã¢ãã³
12.6ïœåã³è§ŠåªïŒçäžã®ãã©ãžãŠã ïŒïŒ ïŒïŒïœã
å ãããæ··åç©ã50â60âåã³10â30ããŒã«ã®æ°Ž
çŽ å§ã§æ°ŽçŽ åããã觊åªããå¥ãã溶液äžã®ïŒâ
ãžã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ã®å«æ
éãäºç¡é žæ»Žå®ã«ãã枬å®ããïŒåççè«å€ã®94
ïŒ ïŒãã¡ãã«ã°ãªã³ãŒã«åã³æ°Žãæžå§ïŒ22mmïŒèž
çã«ããé€å»ããæ®çç©ãã¡ã¿ããŒã«735ïœäžã«
溶解ãããããã®åŸã®æº¶æ¶²ã«é žåãã°ãã·ãŠã
20.2ïœïŒ0.5ã¢ã«ïŒãå ããã次ã«ïŒâ15âã§ç¡
æ°Žé ¢é ž93.9ïœïŒ0.92ã¢ã«ïŒãïŒ 1/2æé以å ã«æ»Ž
å ãããã®éïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâ
βâã¡ããã·ãšããã·ãã³ãŒã³ãé«ãéžæçã§åŸ
ããããçæç©ååžãHPLCâåæïŒãHPLCãâ
é«å§æ¶²äœã¯ãããã°ã©ãã€ãŒïŒã«ãã枬å®ããïŒ ïŒïŒïŒâãžã¢ããâαâã¡ããã·ãšããã·ãã³
ãŒã³ ïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ãã
ã·ãšããã·ãã³ãŒã³ 89ïŒ ïŒïŒïŒâãžã¢ã»ãã«ã¢ããâβâã¡ããã·ãšã
ãã·ãã³ãŒã³ ïŒïŒ æ··åç©ïŒïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ïŒâ§0.5ã¢ã«ïŒ665.7ïœ
ã掻æ§ç12.5ïœåã³ããããå12.5ïœã§æž æŸå
ããããªãšãã«ã¢ãã³6.3ïœåã³è§ŠåªïŒçäžãã©
ãžãŠã ïŒïŒ ïŒ2.5ïœãå ãããæ··åç©ã«ã¢ã»ãã¢
ã«ããã26.6ïœïŒ0.6ã¢ã«ïŒãå ãã50â60âå
ã³40â80ããŒã«ã®æ°ŽçŽ å§ã§æ°ŽçŽ åããã觊åªãã
åããã¡ã¿ããŒã«ã倧æ°å§ã§çåºããçæç©ãæ°Ž
200ïœã«ããæ²æ®¿ã«ããåé¢ããã ã¢ã«ãã«åã®éžæ床ïŒHPLCâåæïŒïŒ ã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ããã·ãš
ããã·ãã³ãŒã³ 4.6ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ 93ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ 2.4ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ã®åçã¯äœ¿çšïŒïŒïŒâ
ãžãããã¯ãã«ãã³ãŒã³ã«å¯Ÿãçè«å€ã®72ïŒ ã§ã
ããèç¹72â73âãããªãšãã«ã¢ãã³12.6ïœã®ä»£
ãã«ãžã€ãœãããã«ã¢ãã³12.6ïœã䜿çšããããŠ
ãã®ä»ã¯åèšãšåæ§ã«å®æœããã°ç®ççæç©ã®å
çåã³çµæã«é¢ããŠåäžã®çµæãåŸãããã ããªãšãã«ã¢ãã³12.6ïœã®ä»£ãã«ããªâïœâã
ãã«ã¢ãã³12.6ïœã䜿çšããããŠãã®ä»ã¯åèšãš
åæ§ã«å®æœããã°ç®ççæç©ã®åçåã³çµæã«é¢
ããŠåäžã®çµæãåŸãããã äŸ ïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ããâïŒâããããª
ãã«ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ïŒäŸ
ïŒãšåæ§ã«è£œé ïŒ119ïœïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã掻æ§
ç6.3ïœåã³ããããå6.3ïœã§æž æŸåããããã®
åŸã液ã«ããªãšãã«ã¢ãã³6.3ïœåã³è§ŠåªïŒçäž
ãã©ãžãŠã ïŒïŒ ïŒ2.5ïœãå ãããåŒãç¶ããŠã¢
ã»ãã¢ã«ããã33.3ïœïŒ0.75ã¢ã«ïŒã®ååšäžïŒæ
é以å ã«50â60âåã³40â80ããŒã«ã®æ°ŽçŽ å§ã§æ°Ž
çŽ åãããåå¿æº¶æ¶²ãã觊åªãåé¢ããåŸãçªçŽ
ã®äžã§ã¡ã¿ããŒã«åã³æ°Žãèžçã«ãã€ãŠé€å»ã
ãã次ã«180ïœã®æ°Žãæ·»å ããããšã«ãã€ãŠçæ
ç©ãæ²æ®¿ãããåžåŒãéãã20ïŒ é£å¡©æº¶æ¶²100ïœ
ã§æŽæµãããïŒâãšãã«ã¢ããâïŒâããããªã
ã«ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ã®åç
ã¯ã䜿çšããïŒâã¢ããâïŒâããããªãã«ã¢ã
ãâβâã¡ããã·ãšããã·ãã³ãŒã³ã«å¯Ÿããçè«
å€ã®84ïŒ ã§ããã 也ç¥è©Šæã®èç¹ïŒ78â80âã ã¢ã«ãã«åã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ããâïŒâããããªãã«ã¢ããâβâã¡
ããã·ãšããã·ãã³ãŒã³ ïŒïŒ ïŒâãšãã«ã¢ããâïŒâããããªãã«ã¢ããâ
βâã¡ããã·ãšããã·ãã³ãŒã³ 93.5ïŒ ïŒâãžãšãã«ã¢ããâïŒâããããªãã«ã¢ãã
âβâã¡ããã·ãšããã·ãã³ãŒã³ 2.5ïŒ äŸ ïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ããã¢ããœãŒã«ïŒäŸïŒãšåæ§ã«è£œé ïŒ90ïœ
ïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã«ããªãšãã«ã¢ãã³6.3ïœåã³
觊åªïŒçäžãã©ãžãŠã ïŒïŒ ïŒ2.5ïœãå ãããæ··
åç©ãã¢ã»ãã¢ã«ããã26.4ïœïŒ0.6ã¢ã«ïŒã®å
åšäž40â60ããŒã«ã®æ°ŽçŽ å§åã³50â60âã®æž©åºŠã§
ïŒæé以å ã«æ°ŽçŽ åããã觊åªã®ãå¥åŸã¡ã¿ããŒ
ã«ãã¡ã¿ããŒã«ãèžçã«ãã€ãŠé€å»ããçæç©ã
æ°Ž200ïœã®æ·»å ã«ããæ²æ®¿ããããïŒâã¢ã»ãã«
ã¢ããâïŒâãšãã«ã¢ããã¢ããœãŒã«ã®åçã¯ç
è«å€ã®86ïŒ ã§ãããèç¹94â102âã ã¢ã«ãã«åã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããã¢ããœãŒã«
ïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâã¢ã
ãœãŒã« 96ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâã¢
ããœãŒã« ïŒïŒ äŸ ïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ãããžããšãã«ãšãŒãã«ïŒäŸïŒãšåæ§ã«è£œé ïŒ
121ïœïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã«ããªãšãã«ã¢ãã³6.3
ïœåã³è§ŠåªïŒçäžãã©ãžãŠã ïŒïŒ ïŒ2.5ïœãå ã
ããæ··åç©ãã¢ã»ãã¢ã«ããã28.6ïœïŒ0.65ã¢
ã«ïŒã®ååšäžïŒæé50â60âåã³40â80ããŒã«ã®
æ°ŽçŽ å§ã§æ°ŽçŽ åããã觊åªã®ãå¥åŸæº¶å€ãèžçã«
ããé€å»ããçæç©ãæ°Ž200ïœã®æ·»å ã«ããæ²æ®¿
ãããã ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ãããžããš
ãã«ãšãŒãã«ã®åçã¯çè«å€ã®88ïŒ ã§ããã èç¹109â110âã ã¢ã«ãã«åã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâãžããšãã«
ãšãŒãã« ïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâãžã
ãšãã«ãšãŒãã« 89ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâãž
ããšãã«ãšãŒãã« ïŒïŒ äŸ ïŒïŒéå çã¢ã«ãã«åã«é¢ããæ¯èŒäŸïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ïŒäŸïŒã«
ãã補é ïŒ112ïœïŒ0.5ã¢ã«ïŒã®æº¶æ¶²ã60ïŒ ã©ããŒ
ããã±ã«4.3ïœåã³ã¢ã»ãã¢ã«ããã28.6ïœïŒ0.65
ã¢ã«ïŒã®ååšäž60â70âåã³40â80ããŒã«ã®æ°ŽçŽ
å§ã§æ°ŽçŽ åããã觊åªã®ãå¥åŸçæç©ãæ°Ž200ïœ
ã®æ·»å ã«ããæ²æ®¿ãããã ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ã®åçã¯çè«å€ã®71ïŒ
ã§ããã åå¿ã®éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ãã
ã·ãšããã·ãã³ãŒã³ 15ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ 77ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ ïŒïŒ äŸ ïŒïŒéå çã¢ã«ãã«åã«é¢ããæ¯èŒäŸïŒ ã¡ã¿ããŒã«395ïœäžïŒâã¢ã»ãã«ã¢ããâïŒâ
ã¢ããâβâã¡ããã·ãšããã·ãã³ãŒã³ïŒ0.5ã¢
ã«ïŒã®æº¶æ¶²ããããªãšãã«ã¢ãã³6.3ïœãããã±
ã«âããããåâ觊åªïŒRCH55ïŒïŒã¡ãŒã«ãŒ
RuhrchemieïŒïŒïœåã³ã¢ã»ãã¢ã«ããã33ïœ
ïŒ0.75ã¢ã«ïŒãïŒ ïŒ1/2æéã§60â85âåã³40â
80ããŒã«ã®æ°ŽçŽ å§ã«æŒãŠæ°ŽçŽ åããã觊åªã®ãå¥
åŸæº¶å€ãèžçã«ãã€ãŠé€å»ããçæç©ãæ°Ž200ïœ
ã®æ·»å ã«ããæ²æ®¿ãããã ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ã®åçã¯çè«å€ã®11ïŒ
ã§ããã éžæçïŒHPLCâåæïŒïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâã¢ããâβâã¡ãã
ã·ãšããã·ãã³ãŒã³ 68ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãšãã«ã¢ããâβâ
ã¡ããã·ãšããã·ãã³ãŒã³ 14ïŒ ïŒâã¢ã»ãã«ã¢ããâïŒâãžãšãã«ã¢ããâβ
âã¡ããã·ãšããã·ãã³ãŒã³ 18ïŒ äŸ ïŒïŒæ¯èŒäŸïŒ 溶èããïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³213
ïœãã¡ã¿ããŒã«632ïœã«å°å ¥ããæ¹æããªãã溶
解ããããæ¹æãããŠãã溶液ã«ããã圢ã®åºåœ¢
æ°Žé žåãããªãŠã 42ïœããåå¿æº¶æ¶²ãå ç±ãããŠ
éæµäžã§ç·©ããã«æ²žéš°ããæ§ã«ãæ·»å ãããæ°Žé ž
åãããªãŠã å šéã®æ·»å åŸïŒæééæµäžå ç±ã
ããåŒãç¶ããŠå·åŽããïŒæ®Žå·ç¹èš±ç¬¬0011048å·
æ现æžã®äŸïŒã®åå¿æ®µéïŒåç §ïŒã ãã®æ§ã«åŸãããæžæ¿æ¶²ïŒïŒïŒïŒâãžãããã¢
ããœãŒã«ãå«æïŒããã©ãžãŠã ïŒïŒ ïŒçäžã§60â
ã«æŒãŠæ°ŽçŽ åãããã®éïŒïŒïŒâãžã¢ããã¢ããœ
ãŒã«ã®åçã¯çè«å€ã®95.2ïŒ ã«çžåœããã äŸ ïŒïŒæ¯èŒäŸïŒ äŸïŒãšåæ§ã«ãããªãŠã ã¡ãã¬ãŒãã®ã¡ã¿ããŒ
ã«æ§æº¶æ¶²ã«1/2æé以å ã«ïŒâ10âã§ïŒïŒïŒâãž
ãããã¯ãã«ãã³ãŒã³ã®ã¡ã¿ããŒã«æ§æº¶æ¶²ã滎å
ããããŠïŒæéåŸæ¹æããŠè£œé ãããïŒïŒïŒâãž
ãããã¢ããœãŒã«ãå«æããæžæ¿æ¶²ã«45ïœã®æ°Ž
ïŒå³ã¡æ®Žå·ç¹èš±ç¬¬0011048å·æ现æžã®äŸïŒã«å¥æ³ãš
ããŠæèšãããŠãã50ïŒ ã®èæ§ãœãŒã氎溶液ã®æ·»
å ãçšããå Žåã«ããã®äŸïŒã®åå¿æ®µéïŒã«åŸã
åå¿æ··åç©äžã«ååšãããšæãããéã®æ°ŽïŒãå
ãããäŸïŒãšåæ§ã«éè¡ãããæ¥è§Šéå åŸïŒïŒïŒ
âãžã¢ããã¢ããœãŒã«ã®åçã¯çè«å€ã®87.6ïŒ ã
åŸãããã«éãã¬ã äŸ ïŒ ã¡ã¿ããŒã«440éšäžïŒïŒïŒâãžãããã¯ãã«ã
ã³ãŒã³202.5ïœã®æžæ¿æ¶²ã«å®€æž©ã§60å以å ã«ã¡ã¿
ããŒã«äžãããªãŠã ã¡ãã¬ãŒãã®30ïŒ æº¶æ¶²189.1
ïœãæµãããã®é枩床ã¯55â60âã«é«ãŸããã¡ã¿
ããŒã«160éšåã³ããªãšãã«ã¢ãã³ïŒéšã®æ·»å åŸ
ãã©ãžãŠã ïŒïŒ ïŒçäžã§60âã«æŒãŠæ°ŽçŽ åããã
ïŒïŒïŒâãžã¢ããã¢ããœãŒã«ã®åçã¯çè«å€ã®
98.0ïŒ ã§ããã
Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ äžè¬åŒ(1) ïŒåŒäžR1ã¯ã¢ã«ãã«ïŒC1âC4ïŒåã¯ã¢ã«ã³ã
ã·ïŒC1âC4ïŒâã¢ã«ãã«ïŒC1âC4ïŒåºåã¯ããšã
ã«åºâããã¯å¡©çŽ âåã¯èçŽ ååãã¢ã«ãã«
ïŒC1âC4ïŒãã¢ã«ã³ãã·ïŒC1âC4ïŒãããªãã«ãªã
ã¡ãã«âãã«ã«ãã³é žã¢ããâãâNHâã¢ã«ã
ã«ïŒC1âC4ïŒãâïŒã¢ã«ãã«ïŒC1âC4ïŒïŒ2ãâSO2
âNH2ãâSO2âNHâã¢ã«ãã«ïŒC1âC4ïŒãâ
SO2âïŒã¢ã«ãã«ïŒC1âC4ïŒïŒ2ãã¢ã»ãã«ããã³
ãŸã€ã«ã¢ããâåã¯âNHâCOâã¢ã«ãã«ïŒC1
âC4ïŒåºã«ãã眮æãããŠããããšãã§ããâ
ããR2ã¯ãåŒãã¢ã«ãã«ïŒC1âC4ïŒåºããR3 ã¯ã¢ã«ãã«ïŒC1âC4ïŒåºãæå³ããïŒ ã§ç€ºãããïŒâã¢ã·ã«ã¢ããâïŒâã¢ã«ãã«ã¢ã
ãâããšãã«ãšãŒãã«ã補é ããæ¹æ³ã«æŒãŠã
ïŒïŒïŒâãžãããã¯ãã«ãã³ãŒã³ã極æ§ææ©æº¶å€
äžã§ç¡æ°Žçã«äžè¬åŒ(2) R1âOMe ïŒåŒäžR1ã¯åèšã®æå³ãæããMeã¯ã¢ã«ã«ãª
éå±ååã§ããïŒ ã§ç€ºãããã¢ã«ã«ãªéå±ã¢ã«ã³ã¬ãŒãåã¯âããš
ãã¬ãŒããšâ30âã100âã®æž©åºŠã§åå¿ãããŠã
äžè¬åŒ(3) ïŒåŒäžR1ã¯åèšã®æå³ãæããïŒ ã§ç€ºãããïŒïŒïŒâãžãããããšãã«ãšãŒãã«ãš
ãããããäžéåé¢åŸåã¯å¥œãŸããã¯äžéåé¢ã
ãã«æ¥µæ§ææ©æº¶å€å¥œãŸããã¯å¡©çŽ 亀æãè¡ããã
åäžæº¶å€äžã§ãæ°ŽçŽ ãµãå²æ°äžã§åšæç³»ã®ç¬¬ïŒæ
ã®è²Žéå±è§ŠåªïŒã«ãããŠã ãçœéïŒåã³è§Šåªéã®
ææ©çªçŽ å¡©åºã®ååšäž50ã120âã®æž©åºŠã§å¯Ÿå¿ã
ãïŒïŒïŒâãžã¢ããããšãã«ãšãŒãã«ã«éå ãã
ãããäžéåé¢åŸåã¯å¥œãŸããã¯äžéåé¢ããã«
極æ§ææ©æº¶å€äžãâ30ãïŒ90âã®æž©åºŠã§éžæçã«
ã¢ã·ã«åããŠãäžè¬åŒ(4) ïŒåŒäžR1åã³R2ã¯åèšã®æå³ãæããïŒ ã§ç€ºããã察å¿ããïŒâã¢ã·ã«ã¢ããâïŒâã¢ã
ãâããšãã«ãšãŒãã«ãšãããããäžéåé¢åŸå
ã¯å¥œãŸããã¯äžéåé¢ããã«æ¥µæ§ææ©æº¶å€äžã§äž
è¬åŒ(5) ïŒåŒäžR3ã¯åèšã®æå³ãæããïŒ ã§ç€ºãããã¢ã«ãããã§æ°ŽçŽ ãµãå²æ°äžã«æŒãŠåš
æç³»ã®ç¬¬ïŒæã®è²Žéå±è§ŠåªïŒã«ãããŠã ãçœéïŒ
åã³è§Šåªéã®ææ©çªçŽ å¡©åºã®ååšäž30ã120âã®
枩床ã§éžæçã«ã¢ã«ãã«åããããšãç¹åŸŽãšãã
äžèšè£œé æ¹æ³ã ïŒ å段éã®åå¿ã極æ§ææ©æº¶å€ãšããŠã®ïŒâïŒ
åã®ççŽ ååãæããçŽéåã¯æåãã¢ã«ã«ããŒ
ã«åã¯ã°ãªã³ãŒã«åã¯ã°ãªã³ãŒã«ãšãŒãã«äžã§å®
æœããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ éå åã³éžæçã¢ã«ãã«åãçªçŽ å«æææ©å¡©
åºãšããŠã®ããªãžã³ããããªã³ãã¢ã«ããªã³ãã
ãªã¢ã«ãã«ïŒC1âC4ïŒã¢ãã³ããžã¢ã«ãã«ïŒC1
âC4ïŒã¢ãã³åã¯ã¢ã«ãã«æ®åºäžã«ïŒâïŒåã®
ççŽ ååãæããããªã¢ã«ãããŒã«ã¢ãã³ã®ååš
äžå®æœããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé åã¯ç¬¬ïŒé èšèŒ
ã®æ¹æ³ã
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3422809.8 | 1984-06-20 | ||
| DE3422809 | 1984-06-20 | ||
| DE3437665A DE3437665A1 (de) | 1984-06-20 | 1984-10-13 | Verfahren zur herstellung von 4-acylamino-2-alkylamino-phenylethern |
| DE3437665.8 | 1984-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6117549A JPS6117549A (ja) | 1986-01-25 |
| JPH0556334B2 true JPH0556334B2 (ja) | 1993-08-19 |
Family
ID=25822287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60132089A Granted JPS6117549A (ja) | 1984-06-20 | 1985-06-19 | ïŒâã¢ã·ã«ã¢ããâïŒâã¢ã«ãã«ã¢ããâããšãã«ãšãŒãã«ã®è£œæ³ |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0165564B1 (ja) |
| JP (1) | JPS6117549A (ja) |
| DE (2) | DE3437665A1 (ja) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3519983A1 (de) * | 1985-06-04 | 1986-12-04 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 2,4-dinitrophenol-alkoxy-alkylethern |
| DE3519982A1 (de) * | 1985-06-04 | 1986-12-04 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von 2,4-dinitrophenylethern |
| JPS63157244U (ja) * | 1987-03-30 | 1988-10-14 | ||
| EP0285109B1 (de) * | 1987-04-02 | 1992-09-16 | Ciba-Geigy Ag | Verfahren zur Herstellung von 2-Amino-4-acylaminophenylethern |
| DE3804621A1 (de) * | 1988-02-13 | 1989-08-24 | Hoechst Ag | Verfahren zur herstellung von 4-acylamino-2-amino-alkoxybenzolen |
| FR2638453B1 (fr) * | 1988-10-28 | 1991-06-07 | Oreal | Ortho-aminophenols 5-substitues, procede pour les preparer et leur utilisation pour la teinture d'oxydation des fibres keratiniques |
| EP0415884A1 (de) * | 1989-08-28 | 1991-03-06 | Ciba-Geigy Ag | Verfahren zur Herstellung von aromatischen Aminen |
| JP5313703B2 (ja) * | 2009-01-16 | 2013-10-09 | å 山工æ¥æ ªåŒäŒç€Ÿ | ãšã³ã³ãŒãä»é§åäŒéçšãã«ãåã³ãã®è£œé æ¹æ³ã䞊ã³ã«ãå転æ€åºã·ã¹ãã |
| CN104557598A (zh) * | 2015-01-21 | 2015-04-29 | å®åŸœçæºåå·¥æéå ¬åž | 2-ç²æ°§åº-5-ä¹é °æ°šåºè¯èºçåæå·¥èº |
| CN114436876B (zh) * | 2020-10-30 | 2023-03-14 | äžåœç§åŠé¢å€§è¿ååŠç©çç 究æ | äžç§2-æ°šåº-4-ä¹é °æ°šåºè¯ç²éçè¿ç»åææ¹æ³ |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011048B1 (en) * | 1978-09-11 | 1982-01-27 | Toms River Chemical Corporation | A process for the manufacture of substantially pure 3-amino-4-alkoxy-acylanilides from 2,4-dinitrochlorobenzene |
| JPS5618945A (en) * | 1979-07-25 | 1981-02-23 | Sumitomo Chem Co Ltd | Preparation of 2,4-diaminophenyl ether |
| DE3222013A1 (de) * | 1982-06-11 | 1983-12-15 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von kernsubstituierten n-alkylanilinen |
-
1984
- 1984-10-13 DE DE3437665A patent/DE3437665A1/de not_active Withdrawn
-
1985
- 1985-06-13 EP EP85107326A patent/EP0165564B1/de not_active Expired
- 1985-06-13 DE DE8585107326T patent/DE3562913D1/de not_active Expired
- 1985-06-19 JP JP60132089A patent/JPS6117549A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6117549A (ja) | 1986-01-25 |
| DE3562913D1 (en) | 1988-06-30 |
| DE3437665A1 (de) | 1986-01-02 |
| EP0165564A2 (de) | 1985-12-27 |
| EP0165564A3 (en) | 1987-01-14 |
| EP0165564B1 (de) | 1988-05-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6133454A (en) | Method for preparing a substituted perhydroisoindole | |
| JPH0556334B2 (ja) | ||
| US4760183A (en) | Process for the preparation of aromatic dialkylamines | |
| US5616799A (en) | Process for the preparation of glycoloylanilides | |
| KR101653025B1 (ko) | 2-ìë¯žë ž-4-ížëŠ¬í룚ì€ë¡ë©ížíŒëŠ¬ëë¥ì ì ì¡° ë°©ë² | |
| US5886232A (en) | Process for preparing substituted cyclohexanones | |
| US3947405A (en) | Process for making neohesperidine dihydrochalcone | |
| US5744648A (en) | Process for the manufacture of 1, 3-cyclohexanedione | |
| US20220153699A1 (en) | Synthesis of 4-amino-5-methyl-1h-pyridin-2(1h)-on (intermediate compound for the synthesis of the mr antagonist finerenone) from 2-chloro-5-methyl-4-nitro-pyridine-1-oxide using the intermediate compound 2-chloro-5-methyl-4-pyridinamine | |
| US5808086A (en) | Process for preparing bis (2-hydroxyphenyl-3-benztriazole) methanes | |
| US4231962A (en) | 3-Phenoxybenzylideneamines and 3-benzylbenzylideneamines | |
| PL181513B1 (pl) | Sposób wytwarzania N-podstawionych estrów glicyny lub N-podstawionej glicyny, sposób wytwarzania pochodnych indoksylu oraz sposób wytwarzania pochodnych indygo PL | |
| HU194537B (en) | Improved process for preparing 9-carbamoyl-9-/3-amino-propyl/-fluorene derivatives | |
| US5571928A (en) | 4-amino-3-hydroxy-phthalimidine, and a process for the preparation thereof | |
| US3455987A (en) | P-hydroxylaminobenzoylaminoacetonitriles and preparation thereof | |
| EP0007738A1 (en) | Process for producing 2-amino-4-acylaminophenyl ether and 2,4-diaminophenyl ether | |
| US6121492A (en) | Method for preparing 2-trifluoro-methoxy-aniline | |
| JP3505991B2 (ja) | ïŒïŒïŒâãžçœ®æã¢ã³ãã©ãã«ã¢ããã®è£œé æ³ | |
| US5047586A (en) | Process for the preparation of 4-acylamino-2-aminoalkoxybenzenes | |
| JP4187828B2 (ja) | ããã²ãâïŒïŒïŒïœïŒâããªãã³ã®è£œé æ¹æ³ | |
| EP0990639A1 (en) | Process for producing n-cyclopropylanilines and intermediates used therefor | |
| US5498725A (en) | Process for preparing 5-aminodihydropyrrole intermediate thereof and process for preparing said intermediate | |
| JPH05117214A (ja) | ãžããšãã«ã¢ãã³èªå°äœã®è£œé æ³ | |
| US2599653A (en) | Gamma-nitro-gamma-carbalkoxy butyraldehydes and process | |
| JP2533565B2 (ja) | ïŒâïŒïŒâããããã·ãã§ãã«ïŒâã·ã¯ããããµã³ã«ã«ãã³é žåã³ïŒââããããã·ããã§ãã«âïŒâã«ã«ãã³é žã®è£œé æ¹æ³ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |