JPH0222744B2 - - Google Patents
Info
- Publication number
- JPH0222744B2 JPH0222744B2 JP56197769A JP19776981A JPH0222744B2 JP H0222744 B2 JPH0222744 B2 JP H0222744B2 JP 56197769 A JP56197769 A JP 56197769A JP 19776981 A JP19776981 A JP 19776981A JP H0222744 B2 JPH0222744 B2 JP H0222744B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst system
- reaction
- compound
- weight
- oxidizing
- 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 - Lifetime
Links
- 239000003054 catalyst Substances 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000007800 oxidant agent Substances 0.000 claims description 34
- 239000011541 reaction mixture Substances 0.000 claims description 22
- 229910000510 noble metal Inorganic materials 0.000 claims description 17
- 230000001590 oxidative effect Effects 0.000 claims description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000003512 tertiary amines Chemical class 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 229910001882 dioxygen Inorganic materials 0.000 claims description 7
- 150000002736 metal compounds Chemical class 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 5
- 150000003673 urethanes Chemical class 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000010970 precious metal Substances 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- 238000006479 redox reaction Methods 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 31
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- -1 hydroxyl compound Chemical class 0.000 description 20
- 239000002904 solvent Substances 0.000 description 14
- 150000003141 primary amines Chemical class 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000004053 quinones Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 2
- VBQNYYXVDQUKIU-UHFFFAOYSA-N 1,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl VBQNYYXVDQUKIU-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- BIECFEMCDBQPTL-UHFFFAOYSA-N 2-(chloroamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1NCl BIECFEMCDBQPTL-UHFFFAOYSA-N 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IWKQHIPRQDPRKC-UHFFFAOYSA-N ClC1=CC=C2C(C3=C(C=CC(C3=CC2=C1)=O)O)=O Chemical compound ClC1=CC=C2C(C3=C(C=CC(C3=CC2=C1)=O)O)=O IWKQHIPRQDPRKC-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
- IPPWILKGXFOXHO-UHFFFAOYSA-N chloranilic acid Chemical compound OC1=C(Cl)C(=O)C(O)=C(Cl)C1=O IPPWILKGXFOXHO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 125000003375 sulfoxide group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- 150000004055 1,2-benzoquinones Chemical class 0.000 description 1
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- SPJXZYLLLWOSLQ-UHFFFAOYSA-N 1-[(1-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical class C1CCCCC1(N)CC1(N)CCCCC1 SPJXZYLLLWOSLQ-UHFFFAOYSA-N 0.000 description 1
- ATUGSVASGVDJPC-UHFFFAOYSA-N 1-[bis(1-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical class C1CCCCC1(N)C(C1(N)CCCCC1)C1(N)CCCCC1 ATUGSVASGVDJPC-UHFFFAOYSA-N 0.000 description 1
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical class C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- YHAROSAFXOQKCZ-UHFFFAOYSA-N 1-benzofuran-2-ol Chemical class C1=CC=C2OC(O)=CC2=C1 YHAROSAFXOQKCZ-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- PMOCDYOEOUEPAN-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C(=O)O)=CC=C3C(=O)C2=C1 PMOCDYOEOUEPAN-UHFFFAOYSA-N 0.000 description 1
- LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 1
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical class NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 description 1
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 229940075142 2,5-diaminotoluene Drugs 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- KJGPMAHVCDFRBN-UHFFFAOYSA-N 2,6-dichloroanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 KJGPMAHVCDFRBN-UHFFFAOYSA-N 0.000 description 1
- HEFXYRDPFRWXBB-UHFFFAOYSA-N 2-(2-chlorophenyl)cyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC=CC=C1C1=CC(=O)C=CC1=O HEFXYRDPFRWXBB-UHFFFAOYSA-N 0.000 description 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- HJXPGCTYMKCLTR-UHFFFAOYSA-N 2-bromo-9,9-diethylfluorene Chemical compound C1=C(Br)C=C2C(CC)(CC)C3=CC=CC=C3C2=C1 HJXPGCTYMKCLTR-UHFFFAOYSA-N 0.000 description 1
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- FCMRHMPITHLLLA-UHFFFAOYSA-N 2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1N FCMRHMPITHLLLA-UHFFFAOYSA-N 0.000 description 1
- 150000004786 2-naphthols Chemical class 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- OXAUFLJQLMOTSU-UHFFFAOYSA-N 3,4-dimethyl-2-nitroaniline Chemical class CC1=CC=C(N)C([N+]([O-])=O)=C1C OXAUFLJQLMOTSU-UHFFFAOYSA-N 0.000 description 1
- MHQULXYNBKWNDF-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diamine Chemical class CC1=CC=C(N)C(N)=C1C MHQULXYNBKWNDF-UHFFFAOYSA-N 0.000 description 1
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- SQPWWLJPTAUAME-UHFFFAOYSA-N 4-(1,1,2,2,2-pentachloroethyl)aniline Chemical compound NC1=CC=C(C(Cl)(Cl)C(Cl)(Cl)Cl)C=C1 SQPWWLJPTAUAME-UHFFFAOYSA-N 0.000 description 1
- ADUMIBSPEHFSLA-UHFFFAOYSA-N 4-[bis(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 ADUMIBSPEHFSLA-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- AYGGQJHJRFZDFH-UHFFFAOYSA-N 5,7-dichloro-1h-indole-2,3-dione Chemical compound ClC1=CC(Cl)=CC2=C1NC(=O)C2=O AYGGQJHJRFZDFH-UHFFFAOYSA-N 0.000 description 1
- NAQNRFQILKDCBK-UHFFFAOYSA-N 5-amino-2-(4-chloroanilino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1NC1=CC=C(Cl)C=C1 NAQNRFQILKDCBK-UHFFFAOYSA-N 0.000 description 1
- HYLOSPCJTPLXSF-UHFFFAOYSA-N 5-amino-2-anilinobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1NC1=CC=CC=C1 HYLOSPCJTPLXSF-UHFFFAOYSA-N 0.000 description 1
- LVNDUJYMLJDECN-UHFFFAOYSA-N 5-methylbenzene-1,3-diamine Chemical compound CC1=CC(N)=CC(N)=C1 LVNDUJYMLJDECN-UHFFFAOYSA-N 0.000 description 1
- DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XZAHJRZBUWYCBM-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methanamine Chemical class NCC1(CN)CCCCC1 XZAHJRZBUWYCBM-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 229940058934 aminoquinoline antimalarials Drugs 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical class C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical class CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- OWEZJUPKTBEISC-UHFFFAOYSA-N decane-1,1-diamine Chemical class CCCCCCCCCC(N)N OWEZJUPKTBEISC-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- UTVVREMVDJTZAC-UHFFFAOYSA-N furan-2-amine Chemical class NC1=CC=CO1 UTVVREMVDJTZAC-UHFFFAOYSA-N 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical class CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
- SHLTXWFNRJQZTQ-UHFFFAOYSA-N n-chloro-2-methylaniline Chemical compound CC1=CC=CC=C1NCl SHLTXWFNRJQZTQ-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- RHAGYXLHGYNLAX-UHFFFAOYSA-N octane-1,1-diamine Chemical class CCCCCCCC(N)N RHAGYXLHGYNLAX-UHFFFAOYSA-N 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- GPCKFIWBUTWTDH-UHFFFAOYSA-N pentane-3,3-diamine Chemical class CCC(N)(N)CC GPCKFIWBUTWTDH-UHFFFAOYSA-N 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical class NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical group C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- FNXKBSAUKFCXIK-UHFFFAOYSA-M sodium;hydrogen carbonate;8-hydroxy-7-iodoquinoline-5-sulfonic acid Chemical class [Na+].OC([O-])=O.C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 FNXKBSAUKFCXIK-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
ãã®çºæã¯ãé
žåå€ã®ååšäžã«ãããã³å°ããš
ãïŒã€ã®è²Žéå±ãŸãã¯å°ãªããšãïŒã€ã®è²Žéå±å
åç©ã®ååšäžã®åæ¹ã§ã第ïŒçŽã¢ãã³ãææ©ãã
ããã·ã«ååç©ããã³äžé žåççŽ ãšåå¿ãããã
ã®åå¿ãããã€ãååç©ãŸãã¯ããã€ãååç©ã«
転æãããååç©ã®ååšäžã«è¡ãããããšã«ãã
ãŠã¬ã¿ã³ïŒã«ã«ããã³é žãšã¹ãã«ãŸãã¯ã«ã«ãã¡
ãŒãïŒã®æ°èŠãªè£œé æ¹æ³ã«é¢ããã äžè¬çã«ææ©ã€ãœã·ã¢ããŒãã¯å¯Ÿå¿ããã¢ãã³
ããã¹ã²ã³ãšåå¿ãããããšã«ãã€ãŠåæ¥çã«ã€
ããããããããå«ããã¹ã²ã³ã®è£œé ã®ããã®é«
ãå¡©çŽ ã®èŠæ±ããã³é«ããšãã«ã®ãŒã³ã¹ãã®ãã
ã«ããã¹ã²ã³ã䜿ãå¿ èŠã®ãªãææ©ã€ãœã·ã¢ããŒ
ããåŸãããšã«ã€ããŠã®åæ¥çã«å®è¡ã§ããæ¹æ³
ãèŠåºãããã«å€ãã®åªåãããªãã®éçºãããŠ
ãããïŒã€ã®ãããæ¹æ³ã¯ç¬¬ïŒçŽã¢ãã³ãäžé žå
ççŽ ããã³ææ©ããããã·ã«ååç©ããã³ç©ºæ°ãŸ
ãã¯ææ©ãããååç©ã®ããšãé žåå€ãšåå¿ãã
ãŠå¯Ÿå¿ãããŠã¬ã¿ã³ã圢æããç¶ããŠããããŠã€
ãããããŠã¬ã¿ã³ãã€ãœã·ã¢ããŒãããã³ããã
ãã·ã«åºãå«ãååç©ã«åå²ããããšã§ããããŠ
ã¬ã¿ã³ãã€ããããã®ãã®ãã¹ã²ã³ã䜿ããªãæ¹
æ³ã¯ããšãã°ãã€ãå ¬éå ¬å ±ç¬¬2910132å·ãŸãã¯
ãã€ãå ¬éå ¬å ±ç¬¬2908251å·ïŒEPâOS No.
0016346ãŸãã¯ç±³åœåºé¡ç¬¬125394å·ã1980幎ïŒæ
27æ¥åºé¡ïŒã«èšè¿°ãããããããã®ïŒã€ã®å è¡å
è¡ç©ã®ãã¡ã®ç¬¬ïŒã®ãã®ã«èšè¿°ãããæ¹æ³ã«ãã
ãŠã第ïŒçŽã¢ãã³ã¯ãäžé žåççŽ ãææ©ãããã
ã·ã«ååç©ããã³é žåå€ãšããŠã®ååç¶é žçŽ ãŸã
ã¯ãããååç©ã奜ãŸããã¯è²Žéå±è§Šåªã«å ããŠ
å©è§ŠåªãšããŠäœ¿çšãããåå¿æ··åç©ã«å€§ããäžæº¶
æ§ã§ããå¡©åç©å«æç¡æ©åºäœã®ãå šäœãšããŠã®æ··
åç©ã«å¯ŸããŠïŒããïŒééïŒ ãåå¿ãããããšã«
ãã€ãŠè§Šåªçã«ãªãã·ã«ã«ããã«åããããåé¡
ã®å è¡åè¡ç©ã«ããã·ã¹ãã ã«ãããŠãå¡©åç©å«
æååç©ã®æ¯èŒçé«å«éã®ããã«ãè èã®åé¡ã
å ç«ã€ãŠåè¡ãããæ¹æ³ã«çãããããã«å ããŠ
ç¡æ©è§Šåªæåãå®è³ªçã«äžæº¶æ§ã§ãããšããäºå®
ã¯ãå ¬ç¥æ¹æ³ã®åæ¥çãªå®æœã«å³ãã圱é¿ããäž
å©çã§ããã ãããã€ãŠãã®çºæã®ç®çã¯äžèšã®åºçºç©è³ªã
ããŠã¬ã¿ã³ã®æ¹è¯ããã補é æ¹æ³ããã®æ¹æ³ã«ã
ããŠå®è³ªçã«äžæº¶æ§ã§ããããŸãã¯è èæ§ã®è§Šåª
æåã䜿çšããå¿ èŠããªãããŸããã®æ¹æ³ã«ãã
ãŠãåå¿æ··åç©äžã®ãããã®ãã®ã®ããšãæåã®
å²åãå šãããªãæžå°ããããã ãã®çºæã«ãããšããã®ç®çã¯ä»¥äžã«è©³è¿°ãã
ãæ¹æ³ã«ãã€ãŠéæãããã ãã®çºæã¯ ïœ ç¬¬ïŒçŽã¢ãã³ã ïœ å°ããšãïŒã€ã®ããããã·ã«åºãå«ãåå
ç©ãããã³ ïœ äžé žåççŽ ãšã ïœ é žåå€ããã³ ïœ å çŽ ã®åšæè¡šã®ç¬¬å¯æããã®å°ããšãïŒã€
ã®è²Žéå±ããã³ïŒãŸãã¯è²Žéå±ååç©ãå«ã觊
åªç³»ã®ååšäžã«ã åå¿ãããããšã«ãã€ãŠãŠã¬ã¿ã³ã補é ããæ¹
æ³ã«ãããŠããã®åå¿ããä»å çãªæåãšããŠå°
ããšãïŒã€ã®é žåããããã€ãååç©ããã³ïŒãŸ
ãã¯åå¿æ¡ä»¶ã®äžã§é žåããããã€ãååç©ã«è»¢
æãããå°ããšãïŒã€ã®ååç©ãå«ã觊åªç³»ïœ ã®
ååšäžã«è¡ãããããšãç¹åŸŽãšããæ¹æ³ã«é¢ã
ãã ãã®çºæã«ããæ¹æ³ã®ããã®åºçºç©è³ªã¯ ïœ ç¬¬ïŒçŽã¢ãã³ã ïœ ããããã·ã«åºãå«ãææ©ååç©ã ïœ äžé žåççŽ ããã³ ïœ é žåå€ ã§ããã é©åãªç¬¬ïŒçŽã¢ãã³ã¯å°ããšãïŒã€ã®ç¬¬ïŒçŽã¢
ããåºãå«ããããªãææ©ååç©ãç¹ã«å°ããšã
ïŒã€ã®èèªæçãèç°æçãè³éŠæçããŸãã¯è€
çŽ ç°çã«çµåããã¢ããåºã§ãã€ãŠä»»æçã«ãã
ã«å®èœåºãå«ãã§ããããã®ãå å«ãããããªã
第ïŒçŽã¢ãã³ã§ãããè³éŠæãŸãã¯èèªæã¢ãã¢
ãã³ãŸãã¯ãžã¢ãã³ãç¹ã«ç¬¬ïŒçŽã¢ãã³åºããé¢
ããŠãããªãä»ã®é žåæ§ã®çœ®æåºãå«ãŸãªãã¢ã
ã¢ãã³ã䜿çšããããšã奜ãŸãããã¢ãã³ã¯äžè¬
ã«31ãã3000ãŸã§ã®ç¯å²ã奜ãŸããã¯31ãã400
ãŸã§ã®ç¯å²ããã³ããç¹ã«å¥œãŸããã¯31ãã200
ãŸã§ã®ç¯å²ã®ååéãæããã é©åãªè³éŠæãŸãã¯è€çŽ ç°ã¢ãã³ã®äŸã¯ã¢ããª
ã³ãïŒïŒïŒâãžã¢ãããã³ãŒã³ãïŒïŒïŒâãžã¢ã
ããã³ãŒã³ãç°æ§äœã®ã¯ããã¢ããªã³ãïŒïŒïŒâ
ãžã¯ããã¢ããªã³ãïŒâã€ãœãããã«ã¢ããªã³ã
ïœâãã«ã€ãžã³ãã¯ãããã«ã€ãžã³ããã·ãªãž
ã³ãã¢ã«ã³ãã·ã¢ããªã³ãïŒâãã³ã¿ã¯ãããšã
ã«ã¢ããªã³ãïŒâãããã¢ããªã³ãïŒâãããã¢
ããªã³ãïŒâãããã¢ããªã³ãïŒïŒïŒâãžã¢ãã
ãã«ãšã³ãïŒïŒïŒâãžã¢ãããã«ãšã³ãïŒïŒïŒâ
ãžã¢ãããã«ãšã³ãïŒïŒïŒâãžã¢ãããã«ãšã³ã
ïŒïŒïŒâãžã¢ãããã«ãšã³ãïŒïŒïŒâãžã¢ããã
ã«ãšã³ãïŒâã¢ããâïŒâããããã«ãšã³ãïŒâ
ã¢ããâïŒâããããã«ãšã³ãïŒâã¢ããâïŒâ
ããããã«ãšã³ãã¢ããããšããŒã«é¡ããžã¢ãã
ãã·ã¬ã³é¡ãã¢ããããããã·ã¬ã³é¡ãã¢ããã
ãã¿ã¬ã³é¡ãã¢ããã¢ã³ãã©ã»ã³é¡ãã¯ããã¢ã
ãå®æ¯éŠé žé¡ãã¯ããã¢ããå®æ¯éŠé žãšã¹ãã«
é¡ãã¢ãããã³ãŒã³ã¹ã«ãã³é žé¡ãïŒïŒ4â²âãžã¢
ãããžããšãã«ã¡ã¿ã³ãïŒïŒ2â²âãžã¢ãããžããš
ãã«ã¡ã¿ã³ãïŒïŒïŒâãžã¢ãããžããšãã«ã¡ã¿
ã³ãããªã¹âïŒïŒâã¢ããããšãã«ïŒâã¡ã¿ã³ãã¢
ããããªãžã³é¡ãã¢ãããããªã³é¡ãã¢ãããã
ãŒã«é¡ãã¢ãããã©ã³é¡ãã¢ããããªããšã³é¡ã
ãŸãã¯ïŒâã¢ãããã³ãŸãã¢ãŸãŒã«é¡ã§ããã é©åãªèç°æ第ïŒçŽã¢ãã³ã®äŸã¯ã¢ããã·ã¯ã
ãã¿ã³ãã¢ããã·ã¯ããã³ã¿ã³ãã·ã¯ãããã·ã«
ã¢ãã³ãïŒïŒïŒâãžã¢ããã·ã¯ããããµã³ãïŒïŒ
ïŒâãžã¢ããã·ã¯ããããµã³ãïŒïŒïŒâãžã¢ãã
ã·ã¯ããããµã³ããã¹ïŒã¢ããã·ã¯ãããã·ã«ïŒ
âã¡ã¿ã³é¡ãããªã¹âïŒã¢ããâã·ã¯ãããã·ã«ïŒ
âã¡ã¿ã³é¡ã§ããã èèªæ第ïŒçŽã¢ãã³ã®ã°ã«ãŒãã®äŸã¯ã¡ãã«ã¢
ãã³ããšãã«ã¢ãã³ãïŒâãããã«ã¢ãã³ãïŒâ
ãããã«ã¢ãã³ãïŒâããã«ã¢ãã³ãïŒâããã«
ã¢ãã³ãã€ãœããã«ã¢ãã³ã第ïŒçŽâããã«ã¢ã
ã³ãïŒâãã³ãã«ã¢ãã³ãïŒâããã·ã«ã¢ãã³ã
ïŒâãããã«ã¢ãã³ãïŒâãªã¯ãã«ã¢ãã³ãïŒâ
ãã·ã«ã¢ãã³ãïŒâããã·ã«ã¢ãã³ããšãã¬ã³ãž
ã¢ãã³ãïŒïŒïŒâãžã¢ãããããã³ãïŒïŒïŒâãž
ã¢ãããããã³ããžã¢ãããã¿ã³é¡ããžã¢ããã
ã³ã¿ã³é¡ããžã¢ãããããµã³é¡ããžã¢ãããªã¯ã¿
ã³é¡ããžã¢ãããã«ã³é¡ããã³ãžã«ã¢ãã³ããã¹
âïŒã¢ããã¡ãã«ïŒâã·ã¯ããããµã³é¡ããã¹â
ïŒã¢ããã¡ãã«ïŒâãã³ãŒã³ãÏâã¢ããã«ã«ãã³
é žãšã¹ãã«é¡ãÏâã¢ããã«ã«ãã³é žãããªã«é¡
ã§ããã ç¹ã«å¥œãŸãã第ïŒçŽã¢ãã³ã¯ç¹ã«ã¢ããªã³ã眮
æã¢ããªã³é¡ãç°æ§äœã®ãžã¢ãããã«ãšã³é¡ãã
ã³ïŒïŒ4â²âãžã¢ãããžããšãã«ã¡ã¿ã³ã®ããšãè³
éŠæ第ïŒçŽã¢ãã³ã§ããã é©åãªããããã·ã«åºãæããååç©ïœã¯å°ã
ãšãïŒã€ã®ã¢ã«ã³ãŒã«çãŸãã¯ããšããŒã«çã«çµ
åããããããã·ã«åºãå«ã¿ããããŠäžè¬ã«32ã
ã2000ãŸã§ã®ç¯å²ã奜ãŸããã¯32ãã300ãŸã§ã®
ç¯å²ã®ååéãæãããããªãææ©ååç©ã§ã
ããã¢ã«ã³ãŒã«é¡ã¯ããšããŒã«é¡ããã奜ãŸã
ãã é©åãªã¢ã«ã³ãŒã«ã¯ããšãã°32ãã300ã®ç¯å²
ã®ååéãæããã¢ã«ã³ãŒã«ã§ãããåé¡ã®ã¢ã«
ã³ãŒã«ã¯ãããªãçŽéã®ãŸãã¯åæãããã¢ãã
ã€ããªãã¯ãŸãã¯ããªãã€ããªãã¯ã¢ã«ã«ããŒã«
ãŸãã¯ã¢ã«ã±ããŒã«ããããªãã¢ããã€ããªãã¯
ãŸãã¯ããªãã€ããªãã¯ã·ã¯ãã¢ã«ã«ããŒã«ãã·
ã¯ãã¢ã«ã±ããŒã«ãŸãã¯ã¢ã©ã«ã«ããŒã«ã§ãã€ãŠ
ããããäžæŽ»æ§ã®çœ®æåºãå«ããããªãã¢ã«ã³ãŒ
ã«ããŸãé©åã§ãããé©åãªçœ®æåºã¯ãããšãã°
ããã²ã³ååãã¹ã«ããã·ãåºãã¹ã«ãã³åºãã«
ã«ããã«ãŸãã¯ã«ã«ãã³é žãšã¹ãã«åºã§ããããš
ãŒãã«ããªãããå«ãã¢ã«ã³ãŒã«ããŸãååçã«
ã¯é©åã§ãããé©åãªã¢ã«ã³ãŒã«ã®äŸã¯ã¡ã¿ããŒ
ã«ããšã¿ããŒã«ãïœâãããããŒã«ãã€ãœããã
ããŒã«ãïœâãã¿ããŒã«ãïœâãã³ã¿ããŒã«ãïœ
âãããµããŒã«ãã·ã¯ããããµããŒã«ããã³ãžã«
ã¢ã«ã³ãŒã«ãã·ã¯ããšã¿ããŒã«ããšãã¬ã³ã°ãªã³
ãŒã«ããžãšãã¬ã³ã°ãªã³ãŒã«ããããã¬ã³ã°ãªã³
ãŒã«ããžãããã¬ã³ã°ãªã³ãŒã«ãã°ãªã»ããŒã«ã
ãããµã³ããªãªãŒã«ãŸãã¯ããªã¡ãããŒã«ããã
ã³ã§ãããé«çŽã¢ã«ã³ãŒã«ã䜿çšããããªãã°ã
ãã®çºæã«ããæ¹æ³ã«ãããåºçºæåïœãšããŠäž
å¡©åºæ§ã¢ãã³é¡ã䜿çšãããã¹ãã§ãããéã«ã
é«çŽã¢ãã³ïœã䜿çšããããªãã°ãäžå®èœæ§ãã
ããã·ã«ååç©ïœã䜿çšãããã¹ãã§ãããïŒã
ãïŒççŽ ååãå«ãã¢ããã€ããªãã¯èèªæã¢ã«
ã³ãŒã«ããã®çºæã«ããæ¹æ³ã«ãããŠå¥œãŸãã䜿
çšãããã é©åãªããšããŒã«ã¯ãç¹ã«94ãã600ãŸã§ã®ç¯
å²ã®ãç¹ã«94ãã300ãŸã§ã®ç¯å²ã®ååéãæã
ãããšããŒã«ãããšãã°ããšããŒã«ãαâããã
ãŒã«ãβâããããŒã«ãã¢ã³ãã©ããŒã«ãããšã
ã³ã¹ããŒã«ãããããã·ãã³ãŸãã©ã³é¡ãããã
ãã·ãããªã³é¡ããã³ãããšãã°ãžããããã·ã
ã³ãŒã³é¡ããžããããã·ããã¿ã¬ã³é¡ãïŒïŒ4â²â
ãžããããã·ãžããšãã«ã¡ã¿ã³ããã¹ããšããŒã«
ããã©ã¬ããŒã«ãŸãã¯ãããã°ã«ã·ããŒã«ã§ã
ããäžæŽ»æ§ã®çœ®æåºãå«ãäžèšã®ã¿ã€ãã®ãããª
ãããšããŒã«ããŸãé©åã§ãããé©åãªçœ®æåº
ã¯ãããšãã°ããã²ã³ååãã¹ã«ããã·ãåºãã¹
ã«ãã³åºãã«ã«ããã·ã«åºãŸãã¯ã«ã«ãã³é žãšã¹
ãã«åºããããåºãã¢ã«ãã«åºãã¢ãªãŒã«åºãã¢
ã«ã³ãã·åºããã³ã¢ããã·åºã§ããã ç¹ã«å¥œãŸããããšããŒã«ã¯ããšããŒã«ãç°æ§äœ
ã®ã¯ããããšããŒã«é¡ããã¹ããšããŒã«ïŒ¡ãïŒâ
ã€ãœããããã·ããšããŒã«ããã³ïŒâããããã·
âïŒïŒ2â²âãžã¡ãã«âïŒïŒïŒâãžããããã³ãŸã
ã©ã³ã§ããã ãã®çºæã«ããæ¹æ³ã®å®æœã«ãããŠããããã
ã·ã«åºãå«ãææ©ååç©ã¯äžè¬ã«åå¿æ··åç©äžã«
ååšãã第ïŒçŽã¢ãã³åºã®ïŒã¢ã«åœãïŒãã200
ã¢ã«ãŸã§ã奜ãŸããã¯ïŒãã50ã¢ã«ãŸã§ã®ããã
ãã·ã«åºãååšãããããªéã«ãããŠäœ¿çšãã
ããåå¿æ¡ä»¶ã®äžã§æ¶²äœã§ããæ¯èŒçè²»çšã®å®ã
ããããã·ã«ååç©ãäžè¬çã«äœ¿çšãããã®ã§ã
ãããã®éå°ã¯ãã®çºæããæ¹æ³ã®ããã®åå¿åª
質ïŒæº¶åªïŒãšããŠåœ¹ç«ã€ã äžé žåççŽ ã¯ãã®çºæã«ããæ¹æ³ã«ãããä»ã®
åå¿äœïœãšããŠäœ¿çšãããããã®åºçºç©è³ªã¯äžè¬
ã«è£œé ãããã¹ããŠã¬ã¿ã³ã®ã¢ã«åœãïŒããã³30
ã¢ã«ã®éã®äžé žåççŽ ã«çžåœããéã«ãããŠäœ¿çš
ããããæèšããã°ãïŒãã30ã¢ã«ãŸã§ã®äžé žå
ççŽ ãåå¿æ··åç©ã«ååšãã第ïŒçŽã¢ããåºã®å
ã¢ã«ã«å¯ŸããŠäžè¬ã«äœ¿çšãããã çŽåã®åœ¢ã«ããããŸãã¯çªçŽ ãŸãã¯äºé žåççŽ
ã®ããšãäžæŽ»æ§ã¬ã¹ãšã®æ··åç©ã®åœ¢ã«ããããç¹
ã«ç©ºæ°ã®åœ¢ã«ãããååç¶é žçŽ ãé žåå€ïœãšããŠ
䜿çšãããããååç¶é žçŽ ã®ååšäžã«ãããŠããª
ãã·ã«ã«ããã«åã¯æ¬¡ã®äžè¬åŒã«åŸã€ãŠçèµ·ã
ãã RNH2ïŒïŒïŒ2O2ïŒCOïŒRâ²OHâ
RNHCO2Râ²ïŒH2O æèšããã°ãïŒã¢ã«ã®äžé žåççŽ ãš1/2ã¢ã«ã®
é žçŽ ãçæããåãŠã¬ã¿ã³ã®ããã«å¿ èŠã§ããã
äžè¬çã«ååç¶é žçŽ ã¯å®è³ªçã«ååŠéè«éããå
å¿ãããã¹ãã¢ããåºã«å¯ŸããŠå®è³ªçã«ïŒåéå°
éã«ãããŠäœ¿çšããããé žåå€ã«å¯ŸããŠææãªã¢
ã«ã³ãŒã«ïœã䜿çšãããå Žåã¯ãé žé žåå€ïœãšã
ãŠäœ¿çšãããé žçŽ ã¯æåïœã«ãããã¢ããåºã«å¯Ÿ
ããŠæºååŠéè«éã«ãããŠäœ¿çšããããšãå§ãã
ãããããã®ããšã¯é žçŽ ãäžèšã®çåŒã«ãã€ãŠå¿
èŠãªåœéã®60ããã³100ïŒ ã®éã«çžåœããéã«ã
ããŠäœ¿çšãããããšãå åã§ããããšãæå³ã
ãããšããã®ã¯é žåå€ã«ææãªã¢ã«ã³ãŒã«ã䜿çš
ãããå ŽåãæãŸãããªãé žååå¿ã«ãã€ãŠã€ã
ãããåéã®æ倱ã¯é žåå€ïœã®æºååŠéè«éã䜿
çšããããšã«ãã€ãŠã€ããããåéã®æ倱ããã
ããã«æ·±å»ã§ããããããã§ãããããã«å ããŠ
é žåå€ãç¹ã«é žçŽ ã®æºååŠéè«éã䜿çšãããå Ž
åãçæããåå¿æ··åç©ã¯ãã®çºæã«ããæ¹æ³ã®
ããã«å䜿çšãããååå¯èœã®åºçºã¢ãã³ãå«
ããããããªãããæãŸãããªãé žååå¿ã«ãã€
ãŠç Žå£ãããã¢ã«ã³ãŒã«ã¯ååãããªãã ããããªãããé©åãªé žåå€ïœã¯ããŸãé žåã
ãç¡æ©ã®å€§ããã€ãªã³æ§ã®ããã³ç¹ã«çš®ã ã®åå
䟡ã®çšåºŠã«ãããŠçããããšãã§ããæ¯èŒçé«ã
åå䟡ã®çšåºŠã«ãããéå±ã®å¡©ã®ãããªååç©ã§
ãããããšãã°å¡©åç©ãèåç©ãæ°Žé žåç©ãç¡«é ž
å¡©ãé žæ§ç¡«é žå¡©ããªã³é žå¡©ãç¡é žå¡©ãçé žå¡©ã®é°
ã€ãªã³ã¯ãããèªèº«ã«å¯ŸããŠãŸãã¯ä»ã®ãã®æã
ã¯ãªããœé°ã€ãªã³ãšã®çµåãã«ãããŠé©åã§ãã
ã®ã§å¯Ÿã€ãªã³ã®æ§è³ªã¯ããã§ã¯éèŠã§ãªããåæ§
ã«ææ©å¯Ÿã€ãªã³ãããšãã°ã«ã«ãã³é žå¡©ãç¡«é ž
å¡©ããªã³é žå¡©ãã¢ã«ã³ã¬ãŒããŸãã¯ããšãã¬ãŒã
ã€ãªã³ããŸãé°ã€ãªã³ãšããŠååšãããã é«ãéœæ§ã®åå䟡ã®çšåºŠã«ãããååçªå·22ã
ã29ïŒ42ïŒ47ïŒ50ïŒ51ïŒ58ïŒ74ïŒ80ãã83ããã³
92ãæããéå±ã®é¡äŒŒã®å€§ããã€ãªã³æ§ã®ååç©
ããã®çºæã®ç®çã®ããã®ç¡æ©é žåå€ãšããŠç¹ã«
奜ãŸãã䜿çšãããããã®ã¿ã€ãã®ç¡æ©é žåå€ã
䜿çšãããå Žåãæå°ã®è èå¹æããã³åå¿æ··å
ç©äžã®æçšåºŠã®æº¶è§£åºŠãæãããã®ãéžæããã
ãšã奜ãŸãããé žåå€ã®è èæ§ããã³æº¶è§£åºŠã®å
æ¹ã¯ã¢ããåºãå«ãåºçºç©è³ªã®æ··åç©ãšããã³ïŒ
ãŸãã¯è§Šåªç³»ã®ææ©æåãšè€åããããšã«ãã€ãŠ
奜éœåã«åœ±é¿ãããã 倧ããã€ãªã³æ§ã®ç¡æ©é žåå€ã䜿çšãããå Žå
ãªãã·ã«ã«ããã«ååå¿ã¯ããšãã°æ¬¡ã®äžè¬åŒã«
ãããã€ãŠçèµ·ããã RNH2ïŒïŒïŒaMn+ïŒCOïŒRâ²OHâ RNHCO2Râ²ïŒïŒïŒaM(n-a)ïŒ2H+ ãã®åŒã«ãããŠMn+ã¯ãªãã·ã«ã«ããã«ååå¿
ã«ãããŠé»åãåãäžããé žåã®åºŠåïŒn+ãæ
ããéå±ã§ããã ãã®ã¿ã€ãã®ç¡æ©é žåå€ïœãæä»çã«äœ¿çšãã
ãå Žåããããã¯äžè¬çã«ïŒïŒïœãã10ïŒïœã°ã©
ã åœéã奜ãŸããã¯ïŒïŒïœããïŒïŒïœã°ã©ã åœé
ã®ç¡é žååç©ã第ïŒçŽã¢ããåºã®ïŒã¢ã«åœãåå¿
æ··åç©äžã«å©çšããããããªéã«ãããŠçšããã
ãã ä»ã®é©åãªé žåå€ïœã¯ãã®é žååã®ããã«ãã®
çºæã«ããåå¿æ¡ä»¶ã®äžã«ãããŠã¢ãã³ïœãé žå
ããããšãã§ããããã€ãææ©ååç©ã§ãããã
ã®ã¿ã€ãã®ããã€ãææ©ååç©ã¯ãããšãã°çœ®æ
ãŸãã¯é眮æ圢ã®ïœâãã³ãŸããã³ãïœâãã³ãŸ
ããã³ããããããã³ãã¢ã³ãã©ããã³ãå å«ã
ãã é©åãªçœ®æåºã¯ç¹ã«ããšãã°ãã«ã«ãã³é žãã¹
ã«ãã³é žãŸãã¯ã·ã¢ãåºåæ§ã«ãããèªèº«ãŸãã¯
ä»ã®ãã®ãšã®çµåãã«ãããããã²ã³çœ®æåºã®ã
ãšãé žååãå¢å€§ããé»ååžåŒåºã§ãããäŸã®ã
ãæ¹ã«ããäžèšã®ãããã®ããã³ã«å ããŠãå©è§Š
åªãšããŠã®äœ¿çšã®ããã«é©åãªä»¥äžã«è¿°ã¹ããã
ã€ãååç©ã¯ãŸãããã€ãååç©ãšããŠäœ¿çšãã
ãããããã€ãé žåå€ãæä»çã«äœ¿çšãããå Ž
åããããã®ãã®ã¯äžè¬ã«ããã€ãæ§é ã®å°ããš
ãïŒã¢ã«ãããªãã¡ããšãã°ïœâãã³ãŸããã³ã
䜿çšãããå Žåããã®ããã³ã®å°ããšãïŒã¢ã«ã
æåïœã«ããã第ïŒçŽã¢ããåºã®ã¢ã«æ¯ã«å©çšã
ãããããªéã«ãããŠçšããããããã®çºæã«ã
ãããã€ãé žåå€ïœã第ïŒçŽã¢ãã³ã®ãªãã·ã«ã«
ããã«åã«äœ¿çšãããå Žåãåå¿ã¯æ¬¡ã®èª¬æåŒã«
ãã€ãŠçèµ·ããã äŸã®ããæ¹ã«ããè¿°ã¹ãããããã€ãé žåå€ã
ãã®çºæã®æ¹æ³ã«ãããŠäœ¿çšãããå Žåãããã
ã®ãã®ã¯äžèšã®åå¿åŒã«çžåœããååŠéè«éãã
ååŠéè«éã®ïŒåãŸã§ã®ç¯å²ã奜ãŸããã¯ååŠé
è«éã®ïŒãã1.5åã®éãŸã§ã®ç¯å²ã«ãããŠç¹ã«
奜ãŸããçšãããããäŸã®ããæ¹ã«ããè¿°ã¹ãã
ãçš®ã ã®é žåå€ãåæã«äœ¿çšãããå Žåãããã
ã®ãã®ã䜿çšãããéã¯å¿è«ããã«å¿ããŠæžå°ã
ããããäŸã®ããæ¹ã«ããè¿°ã¹ãããã€ãªã³æ§ã
ãã³ïŒãŸãã¯ããã€ãé žåå€ãæä»çã«äœ¿çšãã
ãå Žåãååšããé žåã«ææãªã¢ã«ã³ãŒã«ã¯ãå
åç¶é žçŽ ã䜿çšãããå Žåãããé žåã«ããç Žå£
ãããå±éºæ§ããã€ãšå°ãªãããããã€ãŠïŒã€ã®
åŸã«è¿°ã¹ãé žåå€ã¯äžè¬ã«æºååŠéè«ã«ãããŠäœ¿
çšãããªãããšããã®ã¯ããã¯åéã®æ倱ã«å°ã³
ãã«ãããªãããã§ããã ãã®çºæã«ããæ¹æ³ã¯è§Šåªç³»ïœ ã®ååšäžã«è¡ãª
ãããããããã®è§Šåªç³»ã¯e1å çŽ ã®åšæè¡šã®ç¬¬
å¯æã®å°ããšãïŒã€ã®è²Žéå±ã®ååç©ããã³ïŒ
ãŸãã¯å°ããšãïŒã€ã®è²Žéå±ããã³e2å°ããšãïŒ
ã€ã®é žåããããã€ãååç©ããã³ïŒãŸãã¯åå¿
æ¡ä»¶äžã§é žåããããã€ãååç©ã«è»¢æãããå°
ããšãïŒã€ã®ååç©ãå«ãã 觊åªæåe1ã¯å çŽ ã®åšæ衚第å¯æã®éé¢ã®
貎éå±ãŸãã¯ãããã®éå±ã®ååç©ãããªãã
ãã貎éå±ã¯åå¿æ··åç©ã«å¯æº¶æ§ã®åœ¢ãããšãã°
å¡©åç©ãèåç©ãæ²åç©ãå¡©çŽ è€åäœãèçŽ è€å
äœãæ²çŽ è€åäœãé ¢é žå¡©ãã¢ã»ãã«ã¢ã»ãããŒã
ããã³ä»ã®å¯æº¶æ§è²Žéå±ååç©ã®åœ¢ã«ãããŠç¹ã«
æå©ã«å ããããã奜ãŸãã貎éå±ã¯ãã©ãžãŠ
ã ãã«ãããŠã ããã³ããžãŠã ã§ããããã©ãžãŠ
ã ãç¹ã«å¯æº¶æ§ã®å¡©åãã©ãžãŠã ãŸãã¯é ¢é žãã©
ãžãŠã ã®åœ¢ã«ãããŠäœ¿çšããããšãç¹ã«å¥œãŸã
ãã 觊åªæåe1ã®ããã®å¥œãŸããæ¿åºŠã¯äžè¬ã«è²Žé
å±ãšããŠè¡šããããŸããããããªãã°äœ¿çšããã
溶åªãå«ãå šäœã«å¯ŸããŠãïŒãã100ppmã®ç¯å²ã
奜ãŸããã¯ïŒãã100ppmã®ç¯å²å ã§ããã貎é
å±ã®ããé«ãæ¿åºŠãå¯èœã§ããããããã¯è²Žéå±
ã®å¯èœãªæ倱ã®ããã«çµæžçã§ãªãããšããã®ã¯
ãŠã¬ã¿ã³ã®åéã®å¢å ããªãããã§ããã 觊åªæåe2ã¯é žåããããã€ãååç©ããã³ïŒ
ãŸãã¯åå¿æ¡ä»¶äžã«é žåããããã€ãååç©ã«è»¢
æãããååç©ã§ãããããã€ãååç©ã¯ãããš
ãã°âã¶ã»ã±ãã¹ã㪠ãªã 㶠ããã€ã ã³
ã³ããŠã³ãïŒThe Chemistry of the Quinoid
CompoundïŒâ第ïŒéšããã³ç¬¬ïŒéšã«èšè¿°ããã
ååç©ã§ããããŸãããšãã°ææãŸãã¯ææåé§
ç©è³ªãšããŠå±¡ã ã€ãããããã®ãšè§£ããããåå
çã«ã¯ããã®çºæã«ãã觊åªæåe2ã¯ãã®çºæã«
ããåå¿æ¡ä»¶ã®äžã§è§Šåªæåe1äžã«ååšãã貎é
å±ãé žå段éãŒããããã©ã¹ã®é žå段éã«ãŸã§é ž
åããããšãã§ããã¿ã€ãã®ããã€ãååç©ãç¹
ã«ãã®çºæã«ããæ¡ä»¶ã®äžã§ç¹ã«å¥œãŸãã䜿çšã
ãããã©ãžãŠã ãé žå段éãŒãããé žå段éïŒïŒ
ãŸã§è»¢æãããã¿ã€ãã®ãã®ãããªãããã ããããªããããã®ã¿ã€ãã®ããã€ãååç©ã
䜿çšãã代ãã«ãäžèšã®ã¿ã€ãã®ããã€ãååç©
ã«è»¢æãããååç©ãããªãã¡ãé žååå¿ïŒãã®
çºæã«ããæ¹æ³ã«ãããŠäœ¿çšãããé žåå€ïœã«ã
ã€ãŠã€ããããïŒã«ããããœã«ããªã·ã¹ã«ããã
ãŸãã¯è±é¢åå¿ã«ããäžèšã®ã¿ã€ãã®ããã€ãå
åç©ã«è»¢æãããååç©ããã®çºæã«ãã觊åªæ
åe2ãšããŠäœ¿çšããããã é©åãªããã€ã觊åªæåe2ã¯ã眮æãŸãã¯é眮
æã®ãªã«ããŒããã³ãã©ãŒããã³ãå€æ žããã³ã
ãã³è€çŽ ç°ããã³ããã³ãããã®ã€ãããâã¢
ã«ãã«ãŸãã¯ïŒ®âã¢ãªãŒã«ã€ããèªå°äœãããšã
ã°ïœâããã©ã¯ãããã³ãŸããã³ãïœâããã©ã¯
ãããã³ãŸããã³ãïŒïŒïŒâãžã¯ããâïŒïŒïŒâ
ãžããããã·âïœâãã³ãŸããã³ãïŒâã¯ããã
ãšãã«âïŒïŒïŒâãã³ãŸããã³ãïŒïŒïŒâãžã¯ã
ããããããã³ãã¢ã³ãã©ããã³ãïŒâã¯ããã¢
ã³ãã©ããã³ãïŒâã¯ããâïŒâããããã·â
ïŒïŒ10âã¢ã³ãã©ããã³ãïŒâãããã¢ã³ãã©ã
ãã³âïŒâã«ã«ãã³é žãïŒïŒïŒâãžã¯ããã¢ã³ã
ã©ããã³ãïŒïŒïŒâãžã¯ããã¢ã³ãã©ããã³ã
ïŒïŒïŒâãžã¯ããã¢ã³ãã©ããã³ãïŒïŒïŒâãžã
ãããã·ã¢ã³ãã©ããã³ãã¢ã»ãããã¬ã³ãžãª
ã³ãïŒïŒïŒâãžã¯ããâ1Hâã€ã³ããŒã«âïŒïŒ
ïŒâãžãªã³ãã€ã³ãžãŽãŸãã¯ïŒïŒïŒâãžãããâ
ïŒïŒïŒâããã¯ãµãªã³ãžãªã³ã§ããã ããšãã°ãH.G.ãã€ã·ãã€åã³K.A.ã¯ã³è
ããªãã·ããŒã·ãšã³âãªãã¯ã·ãšã³ããªããŒã
ïŒH.G.Cassidy and K.A.KunâOxidationâ
Reduction PolymerâïŒïŒPolymer Review
Vol.11ãInterscience Publ New York1965ïŒã«
èšè¿°ãããã¿ã€ãã®éåäœã®ããã€ãååç©ããŸ
ã觊åªæåe2ãšããŠäœ¿çšããããã«é©åã§ããã 奜ãŸããããã€ãååç©ã¯ãããšãã°å¡©çŽ ãè
çŽ ãã·ã¢ããã«ã«ãã³é žãŸãã¯ã¹ã«ãã³é žåºã®ã
ãšãé»ååžåŒæ§ã®çœ®æåºã®ïŒãŸãã¯ããããå€ã
ã«ãã€ãŠçœ®æãããããã«ãã€ãŠãã®é žååãå¢
倧ãããã觊åªæåe2ãšããŠäœ¿çšããã®ã«ç¹ã«å¥œ
ãŸããããã€ãååç©ã¯ãããšãã°ïœâããã©ã¯
ããâãã³ãŸããã³ãïœâããã©ã¯ãããã³ãŸã
ãã³ãïŒïŒïŒâãžã¯ããâïŒïŒïŒâãžããããã·
âïœâãã³ãŸããã³ãïŒïŒïŒâãžã¯ãããããã
ãã³ãïŒâã¯ããâïŒâããããã·âïŒïŒ10âã¢
ã³ãã©ããã³ãïŒïŒïŒâãžã¯ããã¢ã³ãã©ããã³
ããã³ïŒïŒïŒâãžã¯ããâã¢ã³ãã©ããã³ã§ã
ãã 觊åªæåe2ãšããŠäœ¿çšããã®ã«é©åãªããã€ã
ååç©ã®äºåçãªæ®µéã¯ãããšãã°ã察å¿ããã
ãã€ã觊åªæåã®ã±ã¿ãŒã«ããã³ãããã®æåã®
æ°ŽçŽ åããã圢ãç¹ã«ãã€ããããã³é¡ã§ããã
åæ§ã«ãããšãã°ã¹ã«ãã³é žãã«ã«ãã³é žããã
ããŸãã¯ã·ã¢ãåºã«ãã眮æãããããŸãã¯ç°ã·
ã¹ãã äžã«æ¢ã«ãªããœåºãå«ãè³éŠæã¢ãã³ãã
ã³å€æ žè³éŠæååç©ã¯é žååå¿æ¡ä»¶ãããšãã°å
åç¶é žçŽ ã«ãã€ãŠãã®çºæã«ããããã€ã觊åªæ
åe2ã«è»¢æããããããã€ã觊åªæåe2ã®ããã«
é©åãªäºåçãªæ®µéã¯äžèšã®ããã³ã®ã±ã¿ãŒã«ã
ãã³ãããããã³ãŸãã¯ïŒâã¢ããâïŒâïŒããš
ãã«âã¢ããïŒâãã³ãŒã³ã¹ã«ãã³é žãïŒâã¢ã
ãâïŒâãïŒïŒâã¯ããããšãã«ïŒâã¢ãããâãã³
ãŒã³ã¹ã«ãã³é žãïŒïŒ4â²âãžã¢ããâïŒïŒïŒïŒâ
ãžããšãã«ïŒâïŒïŒ3â²âãžã¹ã«ãã³é žãïŒâã¢ã
ããã³ãŒã³ã¹ã«ãã³é žããã³ãã³ãºã¢ã³ã¹ãã³â
ïŒâã«ã«ãã³ããã«ã§ããã ãã®çºæã«ãã觊åªæåe2ã¯äžè¬ã«äœ¿çšããã
溶åªãå«ãåå¿æ··åç©ã®å šéã«å¯ŸããŠ0.1ééïŒ
ããïŒééïŒ ãŸã§ã®æ¿åºŠã«ãããŠã奜ãŸããã¯
0.5ããïŒééïŒ ãŸã§ã®æ¿åºŠã«ãããŠåå¿ç³»ã«å
ããããã ããããããšãããããã€ãååç©ã¯é žåå€ïœ
ããã³è§Šåªæåïœ ã®äºéã®äœçšãè¡ãªãããšãã§
ããããã®å Žåããã¡ããé žåå€ïœã®éã«å¯Ÿãã
åè¿°ã®èŠ³å¯ã«èª¿åããŠããå€ãã®ããã€ãååç©
ã䜿çšããããšãå¿ èŠã§ããã ãã®çºæã«ãã䜿çšããã觊åªæåïœ ã¯ããã
以å€ã®æåãšããŠä»»æçã«æãçš®ã®éå±ååç©e3
ããã³ïŒãŸãã¯ç¬¬ïŒçŽã¢ãã³ãå«ã¿ããã ä»»æçãªè§Šåªæåe3ã¯ãã°ãã·ãŠã ååç©ãç¹
ã«ãã°ãã·ãŠã ã®ç¡æ©ãŸãã¯ææ©å¡©ãŸãã¯åå¿æ¡
件äžã§é žåéå åå¿ãããããšãã§ããå çŽ ã®åš
æè¡šã®ç¬¬ããæäž»æããã³ïŒãŸãã¯ç¬¬ãã
å¯æã®å çŽ ã®ååç©ãããªããããåå¿æ··åç©
äžã«å°ããšãäžéšå溶解ããããã®ã§ãã€ãŠãå
åçªå·12ïŒ22ãã29ïŒ41ïŒ47ïŒ58ããã³92ãæã
ãéå±ã®ååç©ãä»»æçãªè§Šåªæåe3ãšããŠå¥œãŸ
ãã䜿çšããããç¹ã«å¥œãŸãã觊åªæåe3ã¯ã¯ã
ã ããã³ã¬ã³ãã³ãã«ããé ãã»ãªãŠã ãŸãã¯ã
ã°ãã·ãŠã ã®é ¢é žå¡©ãç¡é žå¡©ãŸãã¯å¡©åç©ãä»»æ
çã«ã¯ãããã®éå±å¡©ã®æ°Žåç©ãŸãã¯ã¢ãã³è€å
äœã®åœ¢ã«ããããã®ã§ãããããšãã°å¡©åã¢ã³ã¢
ããŠã ã®ããšã掻æ§åããå¡©åç©ãšå ±ã«ã觊åªæ
åe3ãšããŠäŸã®æ¹æ³ã«ãã€ãŠè¿°ã¹ãããéå±ã®é ž
åç©ã䜿çšããããšããŸãå¯èœã§ããã觊åªæå
e3ã䜿çšããããšãæå³ãããªãã°ã觊åªæåe1
ã«å¯ŸããŠïŒãã10ã¢ã«åã®éã«ãããŠäžè¬ã«çšã
ããããäžè¬çã«ãããã¯è§Šåªæåe3ã䜿çšãã
ã溶åªãå«ãåå¿æ··åç©ã®å šééã«å¯ŸããŠ0.1é
éïŒ ãŸã§ã®éã«ãããŠäœ¿çšããããããšãæå³ã
ãã ä»»æçãªè§Šåªæåe4ã¯ã觊åªç³»ã«ãããŠè§Šåªæ
åe1é žå圢ã®ãããããã³åå¿æ··åç©äžã«ååšã
ãåºçºååç©ã®é¯åå¹æããã®ç®çã®ããã«äžé©
åœã§ããå Žåã«ã¯ãä»»æçã«è§Šåªæåe3ã®ããã«
é¯åå€ã®äœçšããã第ïŒçŽã¢ãã³ãããªãããã
ååçã«ã¯ãããªã第ïŒçŽã¢ãã³ããªãã¡ãèèª
æçãèç°æçãè³éŠèèªæçããã³ïŒãŸãã¯è³
éŠæçã«çµåãã第ïŒçŽã¢ããåºãŸãã¯è€çŽ ç°ã®
éšåã圢æãã第ïŒçŽã¢ããåºãå å«ããã¿ã€ã
ã®ç¬¬ïŒçŽã¢ãã³ã䜿çšããããšãå¯èœã§ãããé©
åãªç¬¬ïŒçŽã¢ãã³ã¯ãããšãã°ãããªãšãã«ã¢ã
ã³ããžã€ãœãããã«ã¡ãã«ã¢ãã³ãã·ã¯ãããã·
ã«ãžãšãã«ã¢ãã³ãããªããšãã«ã¢ãã³ãïŒïŒ®
âãžãšãã«ã¢ããªã³ãâããšãã«ãããªãžã³ã
ããªãžã³ããããªã³ãïŒïŒïŒâãžã¢ã¶âïŒïŒïŒïŒïŒ
ïŒïŒâãã·ã¯ããªã¯ã¿ã³ãŸãã¯ããªããžã³ã§ããã
奜ãŸãã第ïŒçŽã¢ãã³e4ã¯ããªãšãã«ã¢ãã³ã
ïŒïŒ®âãžãšãã«ã¢ããªã³ããã³ããªãžã³ã§ã
ããäžèšã®ç¬¬ïŒçŽã¢ãã³ã¯è§Šåªæåe1ããã³ä»»æ
çã«ã¯e3ã®éå±é¯å¡©ã®åœ¢ã«ãããŠãŸã䜿çšããã
ãã觊åªæåe1ããã³ïŒãŸãã¯ä»»æçã«ã¯e3ãé ž
å圢ã«ãããŠäœ¿çšããããªãã°ããã®ïŒããã
ã®ïŒæåã掻æ§åããç®çã®ããã«æ°Žé žåç©ã®åœ¢
ã«ãããŠç¬¬ïŒçŽã¢ãã³ã䜿çšããããšãæå©ã§ã
ããä»»æçãªè§Šåªæåe4ã¯äœ¿çšããã溶åªãå«ã
åå¿æ··åç©ã®å šéã«å¯ŸããŠ10ééïŒ ãŸã§ã®éã«ã
ããŠããŸã奜ãŸããã¯0.5ããïŒééïŒ ã®éã«ã
ããŠäœ¿çšããããããããªããã觊åªæåe4ã¯ãŸ
ããã倧éã«äœ¿çšããããã ãã®çºæã«ããåå¿ã¯æº¶åªã®ååšãŸãã¯äžååš
ã®äžã«è¡ãªãããããäžè¬çã«éå°ã«å¥œãŸãã䜿
çšãããææ©ããããã·ã«ååç©ã溶åªãšããŠåœ¹
ç«ã€ãããããªãããåå¿æ··åç©å šéã®80ééïŒ
ãããå€éã®äžæŽ»æ§æº¶åªã䜿çšããããšããŸãå¯
èœã§ãããéå°ã«äœ¿çšãããããããã·ã«ååç©
ãŸãã¯äžæŽ»æ§æº¶åªã®ãããã§ãã€ãŠãã䜿çšãã
ã溶åªã®éã¯ãçºç±æ§ã®ãŠã¬ã¿ã³çæåå¿ã®åå¿
ç±ã枩床ã®åèªãããªãäžæãªãã«æ¶å€±ãããã
ããªããæ¹ã§è©äŸ¡ãããã°ãªããªãããããã
ã«ãäžè¬çã«ããã®çºæã«ããæ¹æ³ã¯ã溶åªãå«
ãå šåå¿æ··åç©ã«å¯ŸããŠïŒãã50ééïŒ ã奜ãŸã
ãã¯ïŒãã20ééïŒ ã®ã¢ããååç©ïœã®æ¿åºŠã䜿
çšããŠè¡ãªãããã é©åãªæº¶åªã¯ãããšãã°ãã³ãŒã³ããã«ãšã³ã
ãã·ã¬ã³ãã¯ãããã³ãŒã³ããžã¯ãããã³ãŒã³ã
ããªã¯ãããã³ãŒã³ãã¯ããããã¿ã¬ã³ãã·ã¯ã
ãããµã³ãã¡ãã«ã·ã¯ããããµã³ãã¯ããã·ã¯ã
ãããµã³ãã¡ãã¬ã³ã¯ãã©ã€ããåå¡©åççŽ ãã
ãã©ã¯ãããšã¿ã³ãããªã¯ããããªãã«ãªããšã¿
ã³ããã³è§Šåªæåe4ãšããŠèšè¿°ãããã¿ã€ãã®ç¬¬
ïŒçŽã¢ãã³ãšåæ§ã®ååç©ã®ããšãä»»æçã«ãã
ã²ã³çœ®æãããè³éŠæãèç°æããã³èèªæçå
æ°ŽçŽ ã®ããšãåå¿æåããã³è§Šåªç³»ã®åæ¹ã«äžæŽ»
æ§ã§ãã溶åªã§ããã åå¿æž©åºŠã¯äžè¬çã«100âãã300âãŸã§ã®ç¯å²
å ãç¹ã«100âãã250âãŸã§ã®ç¯å²å ãç¹ã«æå©
ã«ã¯140âãã220âãŸã§ã®ç¯å²å ã§ãããå§åã¯
液çžã®ååšãåžžã«ä¿èšŒããããããªæ¹æ³ã«ãã€ãŠ
枬å®ãããã°ãªããããããŠäžè¬ã«ïŒãã
500barç¹ã«æå©ã«ã¯30ãã300barãŸã§ã®ç¯å²å
ã§ããã 䜿çšããã第ïŒçŽã¢ãã³ããã³ããããã·åå
ç©ã«ãã€ãŠãå®éçãªåå¿ã«å¿ èŠãšãããåå¿æ
éã¯ãæ°åããæ°æéã®éã§ããã ãã®çºæã«ããæ¹æ³ã¯é£ç¶çãŸãã¯åååŒã§è¡
ãªããããæçµçæç©ïŒãŠã¬ã¿ã³ïŒãé«åºŠã«æº¶è§£
ãã溶åªã䜿çšããããšãæå©ã§ãããåå¿æ··å
ç©ãå§åãã解æŸããããããŠ50ããã³80âã®é
ã«å·åŽãããåŸã觊åªæåe1ããe3ããã³é¯åã
ãã圢ã®ãã®e4ïŒããã䜿çšããããšãïŒã¯å€é
ã®æº¶åªäžã«å®è³ªçã«ãŸãã¯å®å šã«æ²ãã³ãããæ
ãå Žåã«ã¯ã觊åªæ··åç©ã®æ²ãã³ãéæãããã
ã«ãåå¿æ··åç©ããã®ããšã®å®¹ç©ã®70ããã³50ïŒ
ã®éã«æ¿çž®ãããããšãæå©ã§ããã觊åªæ··åç©
ã¯éæãã¯é å¿ã«ãããŠã¬ã¿ã³å«æ溶液ããå
é¢ããããããã®æ¹æ³ã«ãã€ãŠåé¢ããã觊åªæ
åe1ããe3ãŸã§ããã³ä»»æçã«e4ã¯æ®ãã©ã®å Žå
å埪ç°ããããããŠãããã¯ååŠçã«æ¹å€ããã
ãã觊åªçã«åã³æŽ»æ§ã«ãªãããŠã¬ã¿ã³ã¯ãããš
ãã°æº¶åªãèžçºãããããšã«ãã€ãŠæ¶²ããåé¢
ããããããŠããšãã°ç空èžçãŸãã¯çµæ¶åã«ã
ã€ãŠç²Ÿè£œããããå¡©ã®ãããªç¡æ©é žåå€ãŸãã¯ã
ãã³ã®ãããªé žåå€ã䜿çšãããå Žåãäœæ¥ã¯å
æ§ã«è¡ãªããããåå¿åŸã«éå 圢ã«ãããŠããã
ãé žåå€ã¯è§Šåªæåe1ããe3ãŸã§ãå€éã«å«ã¿ã
ãããŠããšãã°ããããã®ååšã«ãããŠåã³é žå
ããããããŠãããã®è§Šåªãšãã€ããã«åå¿ã«æ»
ãããã ãã®çºæã«ããæçµçæç©ïŒãŠã¬ã¿ã³ïŒã¯ã殺
è«å€ãšããŠããŸãã¯æ®ºè«å€ã®è£œé ã®ããã®äžé補
åãšããŠã®äœ¿çšã®ããã«é©åœã§ãããããããªã
ãããããã¯ãããã«ããã€ãœã·ã¢ããŒããã€ã
ãããã®åºçºåæãšããŠäž»ãšããŠèå³ããããã€
ãœã·ã¢ããŒãã®ãã®è£œé ã¯ãã®çºæã«ããæçµç
æç©ã®ç±å解ã«ããå ¬ç¥ã®ããæ¹ã«ãããŠè¡ãªã
ããã ãã®çºæã«ããæ¹æ³ã¯ä»¥äžã®å®æœäŸã«ãã説æ
ããããããã®çºæã¯å®æœäŸã«é瀺ãããæ¡ä»¶ã«
å¶éããããã®ã§ã¯ãªãããŠã¬ã¿ã³åéã¯ããã
ãã®å Žåãã¢ã«ïŒ ã«ãããŠäœ¿çšãããã¢ãã³ã«å¯Ÿ
ãããã®ã§ããã äŸ ïŒ ïŒè§Šåªæåe2ã䜿çšããªãæ¯èŒäŸïŒ 次ã®çµæãæããæ··åç©474ïœããšãã¡ã«åŒã
ã®1.3Lã®çŽéŒè£œãªãŒãã¯ã¬ãŒãã«å°å ¥ãããã é ¢é žãã©ãžãŠã 42ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 211ppm ãšã¿ããŒã« 91.4ééïŒ ã¢ããªã³ 8.6ééïŒ 100barã®äžé žåççŽ ããã³25barã®ç©ºæ°ã宀枩
ã«ãããŠãªãŒãã¯ã¬ãŒãäžã«å°å ¥ãããããªãŒã
ã¯ã¬ãŒãã®å 容ç©ã¯æ¹æããªãã180âã«å ç±ã
ãããããŠãã®æž©åºŠã§ïŒæéåå¿ãç¶ããã宀枩
ã«ãŸã§å·åŽããåŸããªãŒãã¯ã¬ãŒãã¯ææ°ããã
ãããŠç¬¬ïŒã®åæ§ãªåå¿ã®æ®µéãæ°ããCOïŒç©º
æ°æ··åç©ã«ãã€ãŠè¡ãªããããããããã«ãã¢ã
ãªã³ã«å¯Ÿããã»ãŒ1.4é žååœéã®å šéã倧æ°äžã®
é žçŽ ã®åœ¢ã«ãããŠå°å ¥ããããã¬ã¹ã¯ãããã°ã©
ãã€ãŒã«ãã液ç¶åå¿æ··åç©ã®åæã¯ããšãã«ãŠ
ã¬ã¿ã³ã®åéã¯äœ¿çšãããã¢ããªã³ã«å¯ŸããŠ4.5
ïŒ ã«ãªãããšã瀺ãã äŸ ïŒâïŒ ãããã®äŸã¯äŸïŒãšã®æ¯èŒã«ãã觊åªæåe2ã®
觊åªæŽ»æ§ã瀺ããäŸïŒããïŒãŸã§ã«ãããŠè§Šåªæ
åe2ã¯ããã€ãååç©ã§ããããäŸïŒããïŒãŸã§
ã«ãããŠããã¯ããã€ãååç©ã®äºåç段éã§ã
ããæ段ã¯äŸïŒãšåæ§ã§ããã次ã®çµæã®æ··åç©
483ïœã䜿çšãããã é ¢é žãã©ãžãŠã 41ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 207ppm 觊åªæåe2 1.8ééïŒ ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ çµæã¯ç¬¬ïŒè¡šã«è¿°ã¹ãããã
ãïŒã€ã®è²Žéå±ãŸãã¯å°ãªããšãïŒã€ã®è²Žéå±å
åç©ã®ååšäžã®åæ¹ã§ã第ïŒçŽã¢ãã³ãææ©ãã
ããã·ã«ååç©ããã³äžé žåççŽ ãšåå¿ãããã
ã®åå¿ãããã€ãååç©ãŸãã¯ããã€ãååç©ã«
転æãããååç©ã®ååšäžã«è¡ãããããšã«ãã
ãŠã¬ã¿ã³ïŒã«ã«ããã³é žãšã¹ãã«ãŸãã¯ã«ã«ãã¡
ãŒãïŒã®æ°èŠãªè£œé æ¹æ³ã«é¢ããã äžè¬çã«ææ©ã€ãœã·ã¢ããŒãã¯å¯Ÿå¿ããã¢ãã³
ããã¹ã²ã³ãšåå¿ãããããšã«ãã€ãŠåæ¥çã«ã€
ããããããããå«ããã¹ã²ã³ã®è£œé ã®ããã®é«
ãå¡©çŽ ã®èŠæ±ããã³é«ããšãã«ã®ãŒã³ã¹ãã®ãã
ã«ããã¹ã²ã³ã䜿ãå¿ èŠã®ãªãææ©ã€ãœã·ã¢ããŒ
ããåŸãããšã«ã€ããŠã®åæ¥çã«å®è¡ã§ããæ¹æ³
ãèŠåºãããã«å€ãã®åªåãããªãã®éçºãããŠ
ãããïŒã€ã®ãããæ¹æ³ã¯ç¬¬ïŒçŽã¢ãã³ãäžé žå
ççŽ ããã³ææ©ããããã·ã«ååç©ããã³ç©ºæ°ãŸ
ãã¯ææ©ãããååç©ã®ããšãé žåå€ãšåå¿ãã
ãŠå¯Ÿå¿ãããŠã¬ã¿ã³ã圢æããç¶ããŠããããŠã€
ãããããŠã¬ã¿ã³ãã€ãœã·ã¢ããŒãããã³ããã
ãã·ã«åºãå«ãååç©ã«åå²ããããšã§ããããŠ
ã¬ã¿ã³ãã€ããããã®ãã®ãã¹ã²ã³ã䜿ããªãæ¹
æ³ã¯ããšãã°ãã€ãå ¬éå ¬å ±ç¬¬2910132å·ãŸãã¯
ãã€ãå ¬éå ¬å ±ç¬¬2908251å·ïŒEPâOS No.
0016346ãŸãã¯ç±³åœåºé¡ç¬¬125394å·ã1980幎ïŒæ
27æ¥åºé¡ïŒã«èšè¿°ãããããããã®ïŒã€ã®å è¡å
è¡ç©ã®ãã¡ã®ç¬¬ïŒã®ãã®ã«èšè¿°ãããæ¹æ³ã«ãã
ãŠã第ïŒçŽã¢ãã³ã¯ãäžé žåççŽ ãææ©ãããã
ã·ã«ååç©ããã³é žåå€ãšããŠã®ååç¶é žçŽ ãŸã
ã¯ãããååç©ã奜ãŸããã¯è²Žéå±è§Šåªã«å ããŠ
å©è§ŠåªãšããŠäœ¿çšãããåå¿æ··åç©ã«å€§ããäžæº¶
æ§ã§ããå¡©åç©å«æç¡æ©åºäœã®ãå šäœãšããŠã®æ··
åç©ã«å¯ŸããŠïŒããïŒééïŒ ãåå¿ãããããšã«
ãã€ãŠè§Šåªçã«ãªãã·ã«ã«ããã«åããããåé¡
ã®å è¡åè¡ç©ã«ããã·ã¹ãã ã«ãããŠãå¡©åç©å«
æååç©ã®æ¯èŒçé«å«éã®ããã«ãè èã®åé¡ã
å ç«ã€ãŠåè¡ãããæ¹æ³ã«çãããããã«å ããŠ
ç¡æ©è§Šåªæåãå®è³ªçã«äžæº¶æ§ã§ãããšããäºå®
ã¯ãå ¬ç¥æ¹æ³ã®åæ¥çãªå®æœã«å³ãã圱é¿ããäž
å©çã§ããã ãããã€ãŠãã®çºæã®ç®çã¯äžèšã®åºçºç©è³ªã
ããŠã¬ã¿ã³ã®æ¹è¯ããã補é æ¹æ³ããã®æ¹æ³ã«ã
ããŠå®è³ªçã«äžæº¶æ§ã§ããããŸãã¯è èæ§ã®è§Šåª
æåã䜿çšããå¿ èŠããªãããŸããã®æ¹æ³ã«ãã
ãŠãåå¿æ··åç©äžã®ãããã®ãã®ã®ããšãæåã®
å²åãå šãããªãæžå°ããããã ãã®çºæã«ãããšããã®ç®çã¯ä»¥äžã«è©³è¿°ãã
ãæ¹æ³ã«ãã€ãŠéæãããã ãã®çºæã¯ ïœ ç¬¬ïŒçŽã¢ãã³ã ïœ å°ããšãïŒã€ã®ããããã·ã«åºãå«ãåå
ç©ãããã³ ïœ äžé žåççŽ ãšã ïœ é žåå€ããã³ ïœ å çŽ ã®åšæè¡šã®ç¬¬å¯æããã®å°ããšãïŒã€
ã®è²Žéå±ããã³ïŒãŸãã¯è²Žéå±ååç©ãå«ã觊
åªç³»ã®ååšäžã«ã åå¿ãããããšã«ãã€ãŠãŠã¬ã¿ã³ã補é ããæ¹
æ³ã«ãããŠããã®åå¿ããä»å çãªæåãšããŠå°
ããšãïŒã€ã®é žåããããã€ãååç©ããã³ïŒãŸ
ãã¯åå¿æ¡ä»¶ã®äžã§é žåããããã€ãååç©ã«è»¢
æãããå°ããšãïŒã€ã®ååç©ãå«ã觊åªç³»ïœ ã®
ååšäžã«è¡ãããããšãç¹åŸŽãšããæ¹æ³ã«é¢ã
ãã ãã®çºæã«ããæ¹æ³ã®ããã®åºçºç©è³ªã¯ ïœ ç¬¬ïŒçŽã¢ãã³ã ïœ ããããã·ã«åºãå«ãææ©ååç©ã ïœ äžé žåççŽ ããã³ ïœ é žåå€ ã§ããã é©åãªç¬¬ïŒçŽã¢ãã³ã¯å°ããšãïŒã€ã®ç¬¬ïŒçŽã¢
ããåºãå«ããããªãææ©ååç©ãç¹ã«å°ããšã
ïŒã€ã®èèªæçãèç°æçãè³éŠæçããŸãã¯è€
çŽ ç°çã«çµåããã¢ããåºã§ãã€ãŠä»»æçã«ãã
ã«å®èœåºãå«ãã§ããããã®ãå å«ãããããªã
第ïŒçŽã¢ãã³ã§ãããè³éŠæãŸãã¯èèªæã¢ãã¢
ãã³ãŸãã¯ãžã¢ãã³ãç¹ã«ç¬¬ïŒçŽã¢ãã³åºããé¢
ããŠãããªãä»ã®é žåæ§ã®çœ®æåºãå«ãŸãªãã¢ã
ã¢ãã³ã䜿çšããããšã奜ãŸãããã¢ãã³ã¯äžè¬
ã«31ãã3000ãŸã§ã®ç¯å²ã奜ãŸããã¯31ãã400
ãŸã§ã®ç¯å²ããã³ããç¹ã«å¥œãŸããã¯31ãã200
ãŸã§ã®ç¯å²ã®ååéãæããã é©åãªè³éŠæãŸãã¯è€çŽ ç°ã¢ãã³ã®äŸã¯ã¢ããª
ã³ãïŒïŒïŒâãžã¢ãããã³ãŒã³ãïŒïŒïŒâãžã¢ã
ããã³ãŒã³ãç°æ§äœã®ã¯ããã¢ããªã³ãïŒïŒïŒâ
ãžã¯ããã¢ããªã³ãïŒâã€ãœãããã«ã¢ããªã³ã
ïœâãã«ã€ãžã³ãã¯ãããã«ã€ãžã³ããã·ãªãž
ã³ãã¢ã«ã³ãã·ã¢ããªã³ãïŒâãã³ã¿ã¯ãããšã
ã«ã¢ããªã³ãïŒâãããã¢ããªã³ãïŒâãããã¢
ããªã³ãïŒâãããã¢ããªã³ãïŒïŒïŒâãžã¢ãã
ãã«ãšã³ãïŒïŒïŒâãžã¢ãããã«ãšã³ãïŒïŒïŒâ
ãžã¢ãããã«ãšã³ãïŒïŒïŒâãžã¢ãããã«ãšã³ã
ïŒïŒïŒâãžã¢ãããã«ãšã³ãïŒïŒïŒâãžã¢ããã
ã«ãšã³ãïŒâã¢ããâïŒâããããã«ãšã³ãïŒâ
ã¢ããâïŒâããããã«ãšã³ãïŒâã¢ããâïŒâ
ããããã«ãšã³ãã¢ããããšããŒã«é¡ããžã¢ãã
ãã·ã¬ã³é¡ãã¢ããããããã·ã¬ã³é¡ãã¢ããã
ãã¿ã¬ã³é¡ãã¢ããã¢ã³ãã©ã»ã³é¡ãã¯ããã¢ã
ãå®æ¯éŠé žé¡ãã¯ããã¢ããå®æ¯éŠé žãšã¹ãã«
é¡ãã¢ãããã³ãŒã³ã¹ã«ãã³é žé¡ãïŒïŒ4â²âãžã¢
ãããžããšãã«ã¡ã¿ã³ãïŒïŒ2â²âãžã¢ãããžããš
ãã«ã¡ã¿ã³ãïŒïŒïŒâãžã¢ãããžããšãã«ã¡ã¿
ã³ãããªã¹âïŒïŒâã¢ããããšãã«ïŒâã¡ã¿ã³ãã¢
ããããªãžã³é¡ãã¢ãããããªã³é¡ãã¢ãããã
ãŒã«é¡ãã¢ãããã©ã³é¡ãã¢ããããªããšã³é¡ã
ãŸãã¯ïŒâã¢ãããã³ãŸãã¢ãŸãŒã«é¡ã§ããã é©åãªèç°æ第ïŒçŽã¢ãã³ã®äŸã¯ã¢ããã·ã¯ã
ãã¿ã³ãã¢ããã·ã¯ããã³ã¿ã³ãã·ã¯ãããã·ã«
ã¢ãã³ãïŒïŒïŒâãžã¢ããã·ã¯ããããµã³ãïŒïŒ
ïŒâãžã¢ããã·ã¯ããããµã³ãïŒïŒïŒâãžã¢ãã
ã·ã¯ããããµã³ããã¹ïŒã¢ããã·ã¯ãããã·ã«ïŒ
âã¡ã¿ã³é¡ãããªã¹âïŒã¢ããâã·ã¯ãããã·ã«ïŒ
âã¡ã¿ã³é¡ã§ããã èèªæ第ïŒçŽã¢ãã³ã®ã°ã«ãŒãã®äŸã¯ã¡ãã«ã¢
ãã³ããšãã«ã¢ãã³ãïŒâãããã«ã¢ãã³ãïŒâ
ãããã«ã¢ãã³ãïŒâããã«ã¢ãã³ãïŒâããã«
ã¢ãã³ãã€ãœããã«ã¢ãã³ã第ïŒçŽâããã«ã¢ã
ã³ãïŒâãã³ãã«ã¢ãã³ãïŒâããã·ã«ã¢ãã³ã
ïŒâãããã«ã¢ãã³ãïŒâãªã¯ãã«ã¢ãã³ãïŒâ
ãã·ã«ã¢ãã³ãïŒâããã·ã«ã¢ãã³ããšãã¬ã³ãž
ã¢ãã³ãïŒïŒïŒâãžã¢ãããããã³ãïŒïŒïŒâãž
ã¢ãããããã³ããžã¢ãããã¿ã³é¡ããžã¢ããã
ã³ã¿ã³é¡ããžã¢ãããããµã³é¡ããžã¢ãããªã¯ã¿
ã³é¡ããžã¢ãããã«ã³é¡ããã³ãžã«ã¢ãã³ããã¹
âïŒã¢ããã¡ãã«ïŒâã·ã¯ããããµã³é¡ããã¹â
ïŒã¢ããã¡ãã«ïŒâãã³ãŒã³ãÏâã¢ããã«ã«ãã³
é žãšã¹ãã«é¡ãÏâã¢ããã«ã«ãã³é žãããªã«é¡
ã§ããã ç¹ã«å¥œãŸãã第ïŒçŽã¢ãã³ã¯ç¹ã«ã¢ããªã³ã眮
æã¢ããªã³é¡ãç°æ§äœã®ãžã¢ãããã«ãšã³é¡ãã
ã³ïŒïŒ4â²âãžã¢ãããžããšãã«ã¡ã¿ã³ã®ããšãè³
éŠæ第ïŒçŽã¢ãã³ã§ããã é©åãªããããã·ã«åºãæããååç©ïœã¯å°ã
ãšãïŒã€ã®ã¢ã«ã³ãŒã«çãŸãã¯ããšããŒã«çã«çµ
åããããããã·ã«åºãå«ã¿ããããŠäžè¬ã«32ã
ã2000ãŸã§ã®ç¯å²ã奜ãŸããã¯32ãã300ãŸã§ã®
ç¯å²ã®ååéãæãããããªãææ©ååç©ã§ã
ããã¢ã«ã³ãŒã«é¡ã¯ããšããŒã«é¡ããã奜ãŸã
ãã é©åãªã¢ã«ã³ãŒã«ã¯ããšãã°32ãã300ã®ç¯å²
ã®ååéãæããã¢ã«ã³ãŒã«ã§ãããåé¡ã®ã¢ã«
ã³ãŒã«ã¯ãããªãçŽéã®ãŸãã¯åæãããã¢ãã
ã€ããªãã¯ãŸãã¯ããªãã€ããªãã¯ã¢ã«ã«ããŒã«
ãŸãã¯ã¢ã«ã±ããŒã«ããããªãã¢ããã€ããªãã¯
ãŸãã¯ããªãã€ããªãã¯ã·ã¯ãã¢ã«ã«ããŒã«ãã·
ã¯ãã¢ã«ã±ããŒã«ãŸãã¯ã¢ã©ã«ã«ããŒã«ã§ãã€ãŠ
ããããäžæŽ»æ§ã®çœ®æåºãå«ããããªãã¢ã«ã³ãŒ
ã«ããŸãé©åã§ãããé©åãªçœ®æåºã¯ãããšãã°
ããã²ã³ååãã¹ã«ããã·ãåºãã¹ã«ãã³åºãã«
ã«ããã«ãŸãã¯ã«ã«ãã³é žãšã¹ãã«åºã§ããããš
ãŒãã«ããªãããå«ãã¢ã«ã³ãŒã«ããŸãååçã«
ã¯é©åã§ãããé©åãªã¢ã«ã³ãŒã«ã®äŸã¯ã¡ã¿ããŒ
ã«ããšã¿ããŒã«ãïœâãããããŒã«ãã€ãœããã
ããŒã«ãïœâãã¿ããŒã«ãïœâãã³ã¿ããŒã«ãïœ
âãããµããŒã«ãã·ã¯ããããµããŒã«ããã³ãžã«
ã¢ã«ã³ãŒã«ãã·ã¯ããšã¿ããŒã«ããšãã¬ã³ã°ãªã³
ãŒã«ããžãšãã¬ã³ã°ãªã³ãŒã«ããããã¬ã³ã°ãªã³
ãŒã«ããžãããã¬ã³ã°ãªã³ãŒã«ãã°ãªã»ããŒã«ã
ãããµã³ããªãªãŒã«ãŸãã¯ããªã¡ãããŒã«ããã
ã³ã§ãããé«çŽã¢ã«ã³ãŒã«ã䜿çšããããªãã°ã
ãã®çºæã«ããæ¹æ³ã«ãããåºçºæåïœãšããŠäž
å¡©åºæ§ã¢ãã³é¡ã䜿çšãããã¹ãã§ãããéã«ã
é«çŽã¢ãã³ïœã䜿çšããããªãã°ãäžå®èœæ§ãã
ããã·ã«ååç©ïœã䜿çšãããã¹ãã§ãããïŒã
ãïŒççŽ ååãå«ãã¢ããã€ããªãã¯èèªæã¢ã«
ã³ãŒã«ããã®çºæã«ããæ¹æ³ã«ãããŠå¥œãŸãã䜿
çšãããã é©åãªããšããŒã«ã¯ãç¹ã«94ãã600ãŸã§ã®ç¯
å²ã®ãç¹ã«94ãã300ãŸã§ã®ç¯å²ã®ååéãæã
ãããšããŒã«ãããšãã°ããšããŒã«ãαâããã
ãŒã«ãβâããããŒã«ãã¢ã³ãã©ããŒã«ãããšã
ã³ã¹ããŒã«ãããããã·ãã³ãŸãã©ã³é¡ãããã
ãã·ãããªã³é¡ããã³ãããšãã°ãžããããã·ã
ã³ãŒã³é¡ããžããããã·ããã¿ã¬ã³é¡ãïŒïŒ4â²â
ãžããããã·ãžããšãã«ã¡ã¿ã³ããã¹ããšããŒã«
ããã©ã¬ããŒã«ãŸãã¯ãããã°ã«ã·ããŒã«ã§ã
ããäžæŽ»æ§ã®çœ®æåºãå«ãäžèšã®ã¿ã€ãã®ãããª
ãããšããŒã«ããŸãé©åã§ãããé©åãªçœ®æåº
ã¯ãããšãã°ããã²ã³ååãã¹ã«ããã·ãåºãã¹
ã«ãã³åºãã«ã«ããã·ã«åºãŸãã¯ã«ã«ãã³é žãšã¹
ãã«åºããããåºãã¢ã«ãã«åºãã¢ãªãŒã«åºãã¢
ã«ã³ãã·åºããã³ã¢ããã·åºã§ããã ç¹ã«å¥œãŸããããšããŒã«ã¯ããšããŒã«ãç°æ§äœ
ã®ã¯ããããšããŒã«é¡ããã¹ããšããŒã«ïŒ¡ãïŒâ
ã€ãœããããã·ããšããŒã«ããã³ïŒâããããã·
âïŒïŒ2â²âãžã¡ãã«âïŒïŒïŒâãžããããã³ãŸã
ã©ã³ã§ããã ãã®çºæã«ããæ¹æ³ã®å®æœã«ãããŠããããã
ã·ã«åºãå«ãææ©ååç©ã¯äžè¬ã«åå¿æ··åç©äžã«
ååšãã第ïŒçŽã¢ãã³åºã®ïŒã¢ã«åœãïŒãã200
ã¢ã«ãŸã§ã奜ãŸããã¯ïŒãã50ã¢ã«ãŸã§ã®ããã
ãã·ã«åºãååšãããããªéã«ãããŠäœ¿çšãã
ããåå¿æ¡ä»¶ã®äžã§æ¶²äœã§ããæ¯èŒçè²»çšã®å®ã
ããããã·ã«ååç©ãäžè¬çã«äœ¿çšãããã®ã§ã
ãããã®éå°ã¯ãã®çºæããæ¹æ³ã®ããã®åå¿åª
質ïŒæº¶åªïŒãšããŠåœ¹ç«ã€ã äžé žåççŽ ã¯ãã®çºæã«ããæ¹æ³ã«ãããä»ã®
åå¿äœïœãšããŠäœ¿çšãããããã®åºçºç©è³ªã¯äžè¬
ã«è£œé ãããã¹ããŠã¬ã¿ã³ã®ã¢ã«åœãïŒããã³30
ã¢ã«ã®éã®äžé žåççŽ ã«çžåœããéã«ãããŠäœ¿çš
ããããæèšããã°ãïŒãã30ã¢ã«ãŸã§ã®äžé žå
ççŽ ãåå¿æ··åç©ã«ååšãã第ïŒçŽã¢ããåºã®å
ã¢ã«ã«å¯ŸããŠäžè¬ã«äœ¿çšãããã çŽåã®åœ¢ã«ããããŸãã¯çªçŽ ãŸãã¯äºé žåççŽ
ã®ããšãäžæŽ»æ§ã¬ã¹ãšã®æ··åç©ã®åœ¢ã«ããããç¹
ã«ç©ºæ°ã®åœ¢ã«ãããååç¶é žçŽ ãé žåå€ïœãšããŠ
䜿çšãããããååç¶é žçŽ ã®ååšäžã«ãããŠããª
ãã·ã«ã«ããã«åã¯æ¬¡ã®äžè¬åŒã«åŸã€ãŠçèµ·ã
ãã RNH2ïŒïŒïŒ2O2ïŒCOïŒRâ²OHâ
RNHCO2Râ²ïŒH2O æèšããã°ãïŒã¢ã«ã®äžé žåççŽ ãš1/2ã¢ã«ã®
é žçŽ ãçæããåãŠã¬ã¿ã³ã®ããã«å¿ èŠã§ããã
äžè¬çã«ååç¶é žçŽ ã¯å®è³ªçã«ååŠéè«éããå
å¿ãããã¹ãã¢ããåºã«å¯ŸããŠå®è³ªçã«ïŒåéå°
éã«ãããŠäœ¿çšããããé žåå€ã«å¯ŸããŠææãªã¢
ã«ã³ãŒã«ïœã䜿çšãããå Žåã¯ãé žé žåå€ïœãšã
ãŠäœ¿çšãããé žçŽ ã¯æåïœã«ãããã¢ããåºã«å¯Ÿ
ããŠæºååŠéè«éã«ãããŠäœ¿çšããããšãå§ãã
ãããããã®ããšã¯é žçŽ ãäžèšã®çåŒã«ãã€ãŠå¿
èŠãªåœéã®60ããã³100ïŒ ã®éã«çžåœããéã«ã
ããŠäœ¿çšãããããšãå åã§ããããšãæå³ã
ãããšããã®ã¯é žåå€ã«ææãªã¢ã«ã³ãŒã«ã䜿çš
ãããå ŽåãæãŸãããªãé žååå¿ã«ãã€ãŠã€ã
ãããåéã®æ倱ã¯é žåå€ïœã®æºååŠéè«éã䜿
çšããããšã«ãã€ãŠã€ããããåéã®æ倱ããã
ããã«æ·±å»ã§ããããããã§ãããããã«å ããŠ
é žåå€ãç¹ã«é žçŽ ã®æºååŠéè«éã䜿çšãããå Ž
åãçæããåå¿æ··åç©ã¯ãã®çºæã«ããæ¹æ³ã®
ããã«å䜿çšãããååå¯èœã®åºçºã¢ãã³ãå«
ããããããªãããæãŸãããªãé žååå¿ã«ãã€
ãŠç Žå£ãããã¢ã«ã³ãŒã«ã¯ååãããªãã ããããªãããé©åãªé žåå€ïœã¯ããŸãé žåã
ãç¡æ©ã®å€§ããã€ãªã³æ§ã®ããã³ç¹ã«çš®ã ã®åå
䟡ã®çšåºŠã«ãããŠçããããšãã§ããæ¯èŒçé«ã
åå䟡ã®çšåºŠã«ãããéå±ã®å¡©ã®ãããªååç©ã§
ãããããšãã°å¡©åç©ãèåç©ãæ°Žé žåç©ãç¡«é ž
å¡©ãé žæ§ç¡«é žå¡©ããªã³é žå¡©ãç¡é žå¡©ãçé žå¡©ã®é°
ã€ãªã³ã¯ãããèªèº«ã«å¯ŸããŠãŸãã¯ä»ã®ãã®æã
ã¯ãªããœé°ã€ãªã³ãšã®çµåãã«ãããŠé©åã§ãã
ã®ã§å¯Ÿã€ãªã³ã®æ§è³ªã¯ããã§ã¯éèŠã§ãªããåæ§
ã«ææ©å¯Ÿã€ãªã³ãããšãã°ã«ã«ãã³é žå¡©ãç¡«é ž
å¡©ããªã³é žå¡©ãã¢ã«ã³ã¬ãŒããŸãã¯ããšãã¬ãŒã
ã€ãªã³ããŸãé°ã€ãªã³ãšããŠååšãããã é«ãéœæ§ã®åå䟡ã®çšåºŠã«ãããååçªå·22ã
ã29ïŒ42ïŒ47ïŒ50ïŒ51ïŒ58ïŒ74ïŒ80ãã83ããã³
92ãæããéå±ã®é¡äŒŒã®å€§ããã€ãªã³æ§ã®ååç©
ããã®çºæã®ç®çã®ããã®ç¡æ©é žåå€ãšããŠç¹ã«
奜ãŸãã䜿çšãããããã®ã¿ã€ãã®ç¡æ©é žåå€ã
䜿çšãããå Žåãæå°ã®è èå¹æããã³åå¿æ··å
ç©äžã®æçšåºŠã®æº¶è§£åºŠãæãããã®ãéžæããã
ãšã奜ãŸãããé žåå€ã®è èæ§ããã³æº¶è§£åºŠã®å
æ¹ã¯ã¢ããåºãå«ãåºçºç©è³ªã®æ··åç©ãšããã³ïŒ
ãŸãã¯è§Šåªç³»ã®ææ©æåãšè€åããããšã«ãã€ãŠ
奜éœåã«åœ±é¿ãããã 倧ããã€ãªã³æ§ã®ç¡æ©é žåå€ã䜿çšãããå Žå
ãªãã·ã«ã«ããã«ååå¿ã¯ããšãã°æ¬¡ã®äžè¬åŒã«
ãããã€ãŠçèµ·ããã RNH2ïŒïŒïŒaMn+ïŒCOïŒRâ²OHâ RNHCO2Râ²ïŒïŒïŒaM(n-a)ïŒ2H+ ãã®åŒã«ãããŠMn+ã¯ãªãã·ã«ã«ããã«ååå¿
ã«ãããŠé»åãåãäžããé žåã®åºŠåïŒn+ãæ
ããéå±ã§ããã ãã®ã¿ã€ãã®ç¡æ©é žåå€ïœãæä»çã«äœ¿çšãã
ãå Žåããããã¯äžè¬çã«ïŒïŒïœãã10ïŒïœã°ã©
ã åœéã奜ãŸããã¯ïŒïŒïœããïŒïŒïœã°ã©ã åœé
ã®ç¡é žååç©ã第ïŒçŽã¢ããåºã®ïŒã¢ã«åœãåå¿
æ··åç©äžã«å©çšããããããªéã«ãããŠçšããã
ãã ä»ã®é©åãªé žåå€ïœã¯ãã®é žååã®ããã«ãã®
çºæã«ããåå¿æ¡ä»¶ã®äžã«ãããŠã¢ãã³ïœãé žå
ããããšãã§ããããã€ãææ©ååç©ã§ãããã
ã®ã¿ã€ãã®ããã€ãææ©ååç©ã¯ãããšãã°çœ®æ
ãŸãã¯é眮æ圢ã®ïœâãã³ãŸããã³ãïœâãã³ãŸ
ããã³ããããããã³ãã¢ã³ãã©ããã³ãå å«ã
ãã é©åãªçœ®æåºã¯ç¹ã«ããšãã°ãã«ã«ãã³é žãã¹
ã«ãã³é žãŸãã¯ã·ã¢ãåºåæ§ã«ãããèªèº«ãŸãã¯
ä»ã®ãã®ãšã®çµåãã«ãããããã²ã³çœ®æåºã®ã
ãšãé žååãå¢å€§ããé»ååžåŒåºã§ãããäŸã®ã
ãæ¹ã«ããäžèšã®ãããã®ããã³ã«å ããŠãå©è§Š
åªãšããŠã®äœ¿çšã®ããã«é©åãªä»¥äžã«è¿°ã¹ããã
ã€ãååç©ã¯ãŸãããã€ãååç©ãšããŠäœ¿çšãã
ãããããã€ãé žåå€ãæä»çã«äœ¿çšãããå Ž
åããããã®ãã®ã¯äžè¬ã«ããã€ãæ§é ã®å°ããš
ãïŒã¢ã«ãããªãã¡ããšãã°ïœâãã³ãŸããã³ã
䜿çšãããå Žåããã®ããã³ã®å°ããšãïŒã¢ã«ã
æåïœã«ããã第ïŒçŽã¢ããåºã®ã¢ã«æ¯ã«å©çšã
ãããããªéã«ãããŠçšããããããã®çºæã«ã
ãããã€ãé žåå€ïœã第ïŒçŽã¢ãã³ã®ãªãã·ã«ã«
ããã«åã«äœ¿çšãããå Žåãåå¿ã¯æ¬¡ã®èª¬æåŒã«
ãã€ãŠçèµ·ããã äŸã®ããæ¹ã«ããè¿°ã¹ãããããã€ãé žåå€ã
ãã®çºæã®æ¹æ³ã«ãããŠäœ¿çšãããå Žåãããã
ã®ãã®ã¯äžèšã®åå¿åŒã«çžåœããååŠéè«éãã
ååŠéè«éã®ïŒåãŸã§ã®ç¯å²ã奜ãŸããã¯ååŠé
è«éã®ïŒãã1.5åã®éãŸã§ã®ç¯å²ã«ãããŠç¹ã«
奜ãŸããçšãããããäŸã®ããæ¹ã«ããè¿°ã¹ãã
ãçš®ã ã®é žåå€ãåæã«äœ¿çšãããå Žåãããã
ã®ãã®ã䜿çšãããéã¯å¿è«ããã«å¿ããŠæžå°ã
ããããäŸã®ããæ¹ã«ããè¿°ã¹ãããã€ãªã³æ§ã
ãã³ïŒãŸãã¯ããã€ãé žåå€ãæä»çã«äœ¿çšãã
ãå Žåãååšããé žåã«ææãªã¢ã«ã³ãŒã«ã¯ãå
åç¶é žçŽ ã䜿çšãããå Žåãããé žåã«ããç Žå£
ãããå±éºæ§ããã€ãšå°ãªãããããã€ãŠïŒã€ã®
åŸã«è¿°ã¹ãé žåå€ã¯äžè¬ã«æºååŠéè«ã«ãããŠäœ¿
çšãããªãããšããã®ã¯ããã¯åéã®æ倱ã«å°ã³
ãã«ãããªãããã§ããã ãã®çºæã«ããæ¹æ³ã¯è§Šåªç³»ïœ ã®ååšäžã«è¡ãª
ãããããããã®è§Šåªç³»ã¯e1å çŽ ã®åšæè¡šã®ç¬¬
å¯æã®å°ããšãïŒã€ã®è²Žéå±ã®ååç©ããã³ïŒ
ãŸãã¯å°ããšãïŒã€ã®è²Žéå±ããã³e2å°ããšãïŒ
ã€ã®é žåããããã€ãååç©ããã³ïŒãŸãã¯åå¿
æ¡ä»¶äžã§é žåããããã€ãååç©ã«è»¢æãããå°
ããšãïŒã€ã®ååç©ãå«ãã 觊åªæåe1ã¯å çŽ ã®åšæ衚第å¯æã®éé¢ã®
貎éå±ãŸãã¯ãããã®éå±ã®ååç©ãããªãã
ãã貎éå±ã¯åå¿æ··åç©ã«å¯æº¶æ§ã®åœ¢ãããšãã°
å¡©åç©ãèåç©ãæ²åç©ãå¡©çŽ è€åäœãèçŽ è€å
äœãæ²çŽ è€åäœãé ¢é žå¡©ãã¢ã»ãã«ã¢ã»ãããŒã
ããã³ä»ã®å¯æº¶æ§è²Žéå±ååç©ã®åœ¢ã«ãããŠç¹ã«
æå©ã«å ããããã奜ãŸãã貎éå±ã¯ãã©ãžãŠ
ã ãã«ãããŠã ããã³ããžãŠã ã§ããããã©ãžãŠ
ã ãç¹ã«å¯æº¶æ§ã®å¡©åãã©ãžãŠã ãŸãã¯é ¢é žãã©
ãžãŠã ã®åœ¢ã«ãããŠäœ¿çšããããšãç¹ã«å¥œãŸã
ãã 觊åªæåe1ã®ããã®å¥œãŸããæ¿åºŠã¯äžè¬ã«è²Žé
å±ãšããŠè¡šããããŸããããããªãã°äœ¿çšããã
溶åªãå«ãå šäœã«å¯ŸããŠãïŒãã100ppmã®ç¯å²ã
奜ãŸããã¯ïŒãã100ppmã®ç¯å²å ã§ããã貎é
å±ã®ããé«ãæ¿åºŠãå¯èœã§ããããããã¯è²Žéå±
ã®å¯èœãªæ倱ã®ããã«çµæžçã§ãªãããšããã®ã¯
ãŠã¬ã¿ã³ã®åéã®å¢å ããªãããã§ããã 觊åªæåe2ã¯é žåããããã€ãååç©ããã³ïŒ
ãŸãã¯åå¿æ¡ä»¶äžã«é žåããããã€ãååç©ã«è»¢
æãããååç©ã§ãããããã€ãååç©ã¯ãããš
ãã°âã¶ã»ã±ãã¹ã㪠ãªã 㶠ããã€ã ã³
ã³ããŠã³ãïŒThe Chemistry of the Quinoid
CompoundïŒâ第ïŒéšããã³ç¬¬ïŒéšã«èšè¿°ããã
ååç©ã§ããããŸãããšãã°ææãŸãã¯ææåé§
ç©è³ªãšããŠå±¡ã ã€ãããããã®ãšè§£ããããåå
çã«ã¯ããã®çºæã«ãã觊åªæåe2ã¯ãã®çºæã«
ããåå¿æ¡ä»¶ã®äžã§è§Šåªæåe1äžã«ååšãã貎é
å±ãé žå段éãŒããããã©ã¹ã®é žå段éã«ãŸã§é ž
åããããšãã§ããã¿ã€ãã®ããã€ãååç©ãç¹
ã«ãã®çºæã«ããæ¡ä»¶ã®äžã§ç¹ã«å¥œãŸãã䜿çšã
ãããã©ãžãŠã ãé žå段éãŒãããé žå段éïŒïŒ
ãŸã§è»¢æãããã¿ã€ãã®ãã®ãããªãããã ããããªããããã®ã¿ã€ãã®ããã€ãååç©ã
䜿çšãã代ãã«ãäžèšã®ã¿ã€ãã®ããã€ãååç©
ã«è»¢æãããååç©ãããªãã¡ãé žååå¿ïŒãã®
çºæã«ããæ¹æ³ã«ãããŠäœ¿çšãããé žåå€ïœã«ã
ã€ãŠã€ããããïŒã«ããããœã«ããªã·ã¹ã«ããã
ãŸãã¯è±é¢åå¿ã«ããäžèšã®ã¿ã€ãã®ããã€ãå
åç©ã«è»¢æãããååç©ããã®çºæã«ãã觊åªæ
åe2ãšããŠäœ¿çšããããã é©åãªããã€ã觊åªæåe2ã¯ã眮æãŸãã¯é眮
æã®ãªã«ããŒããã³ãã©ãŒããã³ãå€æ žããã³ã
ãã³è€çŽ ç°ããã³ããã³ãããã®ã€ãããâã¢
ã«ãã«ãŸãã¯ïŒ®âã¢ãªãŒã«ã€ããèªå°äœãããšã
ã°ïœâããã©ã¯ãããã³ãŸããã³ãïœâããã©ã¯
ãããã³ãŸããã³ãïŒïŒïŒâãžã¯ããâïŒïŒïŒâ
ãžããããã·âïœâãã³ãŸããã³ãïŒâã¯ããã
ãšãã«âïŒïŒïŒâãã³ãŸããã³ãïŒïŒïŒâãžã¯ã
ããããããã³ãã¢ã³ãã©ããã³ãïŒâã¯ããã¢
ã³ãã©ããã³ãïŒâã¯ããâïŒâããããã·â
ïŒïŒ10âã¢ã³ãã©ããã³ãïŒâãããã¢ã³ãã©ã
ãã³âïŒâã«ã«ãã³é žãïŒïŒïŒâãžã¯ããã¢ã³ã
ã©ããã³ãïŒïŒïŒâãžã¯ããã¢ã³ãã©ããã³ã
ïŒïŒïŒâãžã¯ããã¢ã³ãã©ããã³ãïŒïŒïŒâãžã
ãããã·ã¢ã³ãã©ããã³ãã¢ã»ãããã¬ã³ãžãª
ã³ãïŒïŒïŒâãžã¯ããâ1Hâã€ã³ããŒã«âïŒïŒ
ïŒâãžãªã³ãã€ã³ãžãŽãŸãã¯ïŒïŒïŒâãžãããâ
ïŒïŒïŒâããã¯ãµãªã³ãžãªã³ã§ããã ããšãã°ãH.G.ãã€ã·ãã€åã³K.A.ã¯ã³è
ããªãã·ããŒã·ãšã³âãªãã¯ã·ãšã³ããªããŒã
ïŒH.G.Cassidy and K.A.KunâOxidationâ
Reduction PolymerâïŒïŒPolymer Review
Vol.11ãInterscience Publ New York1965ïŒã«
èšè¿°ãããã¿ã€ãã®éåäœã®ããã€ãååç©ããŸ
ã觊åªæåe2ãšããŠäœ¿çšããããã«é©åã§ããã 奜ãŸããããã€ãååç©ã¯ãããšãã°å¡©çŽ ãè
çŽ ãã·ã¢ããã«ã«ãã³é žãŸãã¯ã¹ã«ãã³é žåºã®ã
ãšãé»ååžåŒæ§ã®çœ®æåºã®ïŒãŸãã¯ããããå€ã
ã«ãã€ãŠçœ®æãããããã«ãã€ãŠãã®é žååãå¢
倧ãããã觊åªæåe2ãšããŠäœ¿çšããã®ã«ç¹ã«å¥œ
ãŸããããã€ãååç©ã¯ãããšãã°ïœâããã©ã¯
ããâãã³ãŸããã³ãïœâããã©ã¯ãããã³ãŸã
ãã³ãïŒïŒïŒâãžã¯ããâïŒïŒïŒâãžããããã·
âïœâãã³ãŸããã³ãïŒïŒïŒâãžã¯ãããããã
ãã³ãïŒâã¯ããâïŒâããããã·âïŒïŒ10âã¢
ã³ãã©ããã³ãïŒïŒïŒâãžã¯ããã¢ã³ãã©ããã³
ããã³ïŒïŒïŒâãžã¯ããâã¢ã³ãã©ããã³ã§ã
ãã 觊åªæåe2ãšããŠäœ¿çšããã®ã«é©åãªããã€ã
ååç©ã®äºåçãªæ®µéã¯ãããšãã°ã察å¿ããã
ãã€ã觊åªæåã®ã±ã¿ãŒã«ããã³ãããã®æåã®
æ°ŽçŽ åããã圢ãç¹ã«ãã€ããããã³é¡ã§ããã
åæ§ã«ãããšãã°ã¹ã«ãã³é žãã«ã«ãã³é žããã
ããŸãã¯ã·ã¢ãåºã«ãã眮æãããããŸãã¯ç°ã·
ã¹ãã äžã«æ¢ã«ãªããœåºãå«ãè³éŠæã¢ãã³ãã
ã³å€æ žè³éŠæååç©ã¯é žååå¿æ¡ä»¶ãããšãã°å
åç¶é žçŽ ã«ãã€ãŠãã®çºæã«ããããã€ã觊åªæ
åe2ã«è»¢æããããããã€ã觊åªæåe2ã®ããã«
é©åãªäºåçãªæ®µéã¯äžèšã®ããã³ã®ã±ã¿ãŒã«ã
ãã³ãããããã³ãŸãã¯ïŒâã¢ããâïŒâïŒããš
ãã«âã¢ããïŒâãã³ãŒã³ã¹ã«ãã³é žãïŒâã¢ã
ãâïŒâãïŒïŒâã¯ããããšãã«ïŒâã¢ãããâãã³
ãŒã³ã¹ã«ãã³é žãïŒïŒ4â²âãžã¢ããâïŒïŒïŒïŒâ
ãžããšãã«ïŒâïŒïŒ3â²âãžã¹ã«ãã³é žãïŒâã¢ã
ããã³ãŒã³ã¹ã«ãã³é žããã³ãã³ãºã¢ã³ã¹ãã³â
ïŒâã«ã«ãã³ããã«ã§ããã ãã®çºæã«ãã觊åªæåe2ã¯äžè¬ã«äœ¿çšããã
溶åªãå«ãåå¿æ··åç©ã®å šéã«å¯ŸããŠ0.1ééïŒ
ããïŒééïŒ ãŸã§ã®æ¿åºŠã«ãããŠã奜ãŸããã¯
0.5ããïŒééïŒ ãŸã§ã®æ¿åºŠã«ãããŠåå¿ç³»ã«å
ããããã ããããããšãããããã€ãååç©ã¯é žåå€ïœ
ããã³è§Šåªæåïœ ã®äºéã®äœçšãè¡ãªãããšãã§
ããããã®å Žåããã¡ããé žåå€ïœã®éã«å¯Ÿãã
åè¿°ã®èŠ³å¯ã«èª¿åããŠããå€ãã®ããã€ãååç©
ã䜿çšããããšãå¿ èŠã§ããã ãã®çºæã«ãã䜿çšããã觊åªæåïœ ã¯ããã
以å€ã®æåãšããŠä»»æçã«æãçš®ã®éå±ååç©e3
ããã³ïŒãŸãã¯ç¬¬ïŒçŽã¢ãã³ãå«ã¿ããã ä»»æçãªè§Šåªæåe3ã¯ãã°ãã·ãŠã ååç©ãç¹
ã«ãã°ãã·ãŠã ã®ç¡æ©ãŸãã¯ææ©å¡©ãŸãã¯åå¿æ¡
件äžã§é žåéå åå¿ãããããšãã§ããå çŽ ã®åš
æè¡šã®ç¬¬ããæäž»æããã³ïŒãŸãã¯ç¬¬ãã
å¯æã®å çŽ ã®ååç©ãããªããããåå¿æ··åç©
äžã«å°ããšãäžéšå溶解ããããã®ã§ãã€ãŠãå
åçªå·12ïŒ22ãã29ïŒ41ïŒ47ïŒ58ããã³92ãæã
ãéå±ã®ååç©ãä»»æçãªè§Šåªæåe3ãšããŠå¥œãŸ
ãã䜿çšããããç¹ã«å¥œãŸãã觊åªæåe3ã¯ã¯ã
ã ããã³ã¬ã³ãã³ãã«ããé ãã»ãªãŠã ãŸãã¯ã
ã°ãã·ãŠã ã®é ¢é žå¡©ãç¡é žå¡©ãŸãã¯å¡©åç©ãä»»æ
çã«ã¯ãããã®éå±å¡©ã®æ°Žåç©ãŸãã¯ã¢ãã³è€å
äœã®åœ¢ã«ããããã®ã§ãããããšãã°å¡©åã¢ã³ã¢
ããŠã ã®ããšã掻æ§åããå¡©åç©ãšå ±ã«ã觊åªæ
åe3ãšããŠäŸã®æ¹æ³ã«ãã€ãŠè¿°ã¹ãããéå±ã®é ž
åç©ã䜿çšããããšããŸãå¯èœã§ããã觊åªæå
e3ã䜿çšããããšãæå³ãããªãã°ã觊åªæåe1
ã«å¯ŸããŠïŒãã10ã¢ã«åã®éã«ãããŠäžè¬ã«çšã
ããããäžè¬çã«ãããã¯è§Šåªæåe3ã䜿çšãã
ã溶åªãå«ãåå¿æ··åç©ã®å šééã«å¯ŸããŠ0.1é
éïŒ ãŸã§ã®éã«ãããŠäœ¿çšããããããšãæå³ã
ãã ä»»æçãªè§Šåªæåe4ã¯ã觊åªç³»ã«ãããŠè§Šåªæ
åe1é žå圢ã®ãããããã³åå¿æ··åç©äžã«ååšã
ãåºçºååç©ã®é¯åå¹æããã®ç®çã®ããã«äžé©
åœã§ããå Žåã«ã¯ãä»»æçã«è§Šåªæåe3ã®ããã«
é¯åå€ã®äœçšããã第ïŒçŽã¢ãã³ãããªãããã
ååçã«ã¯ãããªã第ïŒçŽã¢ãã³ããªãã¡ãèèª
æçãèç°æçãè³éŠèèªæçããã³ïŒãŸãã¯è³
éŠæçã«çµåãã第ïŒçŽã¢ããåºãŸãã¯è€çŽ ç°ã®
éšåã圢æãã第ïŒçŽã¢ããåºãå å«ããã¿ã€ã
ã®ç¬¬ïŒçŽã¢ãã³ã䜿çšããããšãå¯èœã§ãããé©
åãªç¬¬ïŒçŽã¢ãã³ã¯ãããšãã°ãããªãšãã«ã¢ã
ã³ããžã€ãœãããã«ã¡ãã«ã¢ãã³ãã·ã¯ãããã·
ã«ãžãšãã«ã¢ãã³ãããªããšãã«ã¢ãã³ãïŒïŒ®
âãžãšãã«ã¢ããªã³ãâããšãã«ãããªãžã³ã
ããªãžã³ããããªã³ãïŒïŒïŒâãžã¢ã¶âïŒïŒïŒïŒïŒ
ïŒïŒâãã·ã¯ããªã¯ã¿ã³ãŸãã¯ããªããžã³ã§ããã
奜ãŸãã第ïŒçŽã¢ãã³e4ã¯ããªãšãã«ã¢ãã³ã
ïŒïŒ®âãžãšãã«ã¢ããªã³ããã³ããªãžã³ã§ã
ããäžèšã®ç¬¬ïŒçŽã¢ãã³ã¯è§Šåªæåe1ããã³ä»»æ
çã«ã¯e3ã®éå±é¯å¡©ã®åœ¢ã«ãããŠãŸã䜿çšããã
ãã觊åªæåe1ããã³ïŒãŸãã¯ä»»æçã«ã¯e3ãé ž
å圢ã«ãããŠäœ¿çšããããªãã°ããã®ïŒããã
ã®ïŒæåã掻æ§åããç®çã®ããã«æ°Žé žåç©ã®åœ¢
ã«ãããŠç¬¬ïŒçŽã¢ãã³ã䜿çšããããšãæå©ã§ã
ããä»»æçãªè§Šåªæåe4ã¯äœ¿çšããã溶åªãå«ã
åå¿æ··åç©ã®å šéã«å¯ŸããŠ10ééïŒ ãŸã§ã®éã«ã
ããŠããŸã奜ãŸããã¯0.5ããïŒééïŒ ã®éã«ã
ããŠäœ¿çšããããããããªããã觊åªæåe4ã¯ãŸ
ããã倧éã«äœ¿çšããããã ãã®çºæã«ããåå¿ã¯æº¶åªã®ååšãŸãã¯äžååš
ã®äžã«è¡ãªãããããäžè¬çã«éå°ã«å¥œãŸãã䜿
çšãããææ©ããããã·ã«ååç©ã溶åªãšããŠåœ¹
ç«ã€ãããããªãããåå¿æ··åç©å šéã®80ééïŒ
ãããå€éã®äžæŽ»æ§æº¶åªã䜿çšããããšããŸãå¯
èœã§ãããéå°ã«äœ¿çšãããããããã·ã«ååç©
ãŸãã¯äžæŽ»æ§æº¶åªã®ãããã§ãã€ãŠãã䜿çšãã
ã溶åªã®éã¯ãçºç±æ§ã®ãŠã¬ã¿ã³çæåå¿ã®åå¿
ç±ã枩床ã®åèªãããªãäžæãªãã«æ¶å€±ãããã
ããªããæ¹ã§è©äŸ¡ãããã°ãªããªãããããã
ã«ãäžè¬çã«ããã®çºæã«ããæ¹æ³ã¯ã溶åªãå«
ãå šåå¿æ··åç©ã«å¯ŸããŠïŒãã50ééïŒ ã奜ãŸã
ãã¯ïŒãã20ééïŒ ã®ã¢ããååç©ïœã®æ¿åºŠã䜿
çšããŠè¡ãªãããã é©åãªæº¶åªã¯ãããšãã°ãã³ãŒã³ããã«ãšã³ã
ãã·ã¬ã³ãã¯ãããã³ãŒã³ããžã¯ãããã³ãŒã³ã
ããªã¯ãããã³ãŒã³ãã¯ããããã¿ã¬ã³ãã·ã¯ã
ãããµã³ãã¡ãã«ã·ã¯ããããµã³ãã¯ããã·ã¯ã
ãããµã³ãã¡ãã¬ã³ã¯ãã©ã€ããåå¡©åççŽ ãã
ãã©ã¯ãããšã¿ã³ãããªã¯ããããªãã«ãªããšã¿
ã³ããã³è§Šåªæåe4ãšããŠèšè¿°ãããã¿ã€ãã®ç¬¬
ïŒçŽã¢ãã³ãšåæ§ã®ååç©ã®ããšãä»»æçã«ãã
ã²ã³çœ®æãããè³éŠæãèç°æããã³èèªæçå
æ°ŽçŽ ã®ããšãåå¿æåããã³è§Šåªç³»ã®åæ¹ã«äžæŽ»
æ§ã§ãã溶åªã§ããã åå¿æž©åºŠã¯äžè¬çã«100âãã300âãŸã§ã®ç¯å²
å ãç¹ã«100âãã250âãŸã§ã®ç¯å²å ãç¹ã«æå©
ã«ã¯140âãã220âãŸã§ã®ç¯å²å ã§ãããå§åã¯
液çžã®ååšãåžžã«ä¿èšŒããããããªæ¹æ³ã«ãã€ãŠ
枬å®ãããã°ãªããããããŠäžè¬ã«ïŒãã
500barç¹ã«æå©ã«ã¯30ãã300barãŸã§ã®ç¯å²å
ã§ããã 䜿çšããã第ïŒçŽã¢ãã³ããã³ããããã·åå
ç©ã«ãã€ãŠãå®éçãªåå¿ã«å¿ èŠãšãããåå¿æ
éã¯ãæ°åããæ°æéã®éã§ããã ãã®çºæã«ããæ¹æ³ã¯é£ç¶çãŸãã¯åååŒã§è¡
ãªããããæçµçæç©ïŒãŠã¬ã¿ã³ïŒãé«åºŠã«æº¶è§£
ãã溶åªã䜿çšããããšãæå©ã§ãããåå¿æ··å
ç©ãå§åãã解æŸããããããŠ50ããã³80âã®é
ã«å·åŽãããåŸã觊åªæåe1ããe3ããã³é¯åã
ãã圢ã®ãã®e4ïŒããã䜿çšããããšãïŒã¯å€é
ã®æº¶åªäžã«å®è³ªçã«ãŸãã¯å®å šã«æ²ãã³ãããæ
ãå Žåã«ã¯ã觊åªæ··åç©ã®æ²ãã³ãéæãããã
ã«ãåå¿æ··åç©ããã®ããšã®å®¹ç©ã®70ããã³50ïŒ
ã®éã«æ¿çž®ãããããšãæå©ã§ããã觊åªæ··åç©
ã¯éæãã¯é å¿ã«ãããŠã¬ã¿ã³å«æ溶液ããå
é¢ããããããã®æ¹æ³ã«ãã€ãŠåé¢ããã觊åªæ
åe1ããe3ãŸã§ããã³ä»»æçã«e4ã¯æ®ãã©ã®å Žå
å埪ç°ããããããŠãããã¯ååŠçã«æ¹å€ããã
ãã觊åªçã«åã³æŽ»æ§ã«ãªãããŠã¬ã¿ã³ã¯ãããš
ãã°æº¶åªãèžçºãããããšã«ãã€ãŠæ¶²ããåé¢
ããããããŠããšãã°ç空èžçãŸãã¯çµæ¶åã«ã
ã€ãŠç²Ÿè£œããããå¡©ã®ãããªç¡æ©é žåå€ãŸãã¯ã
ãã³ã®ãããªé žåå€ã䜿çšãããå Žåãäœæ¥ã¯å
æ§ã«è¡ãªããããåå¿åŸã«éå 圢ã«ãããŠããã
ãé žåå€ã¯è§Šåªæåe1ããe3ãŸã§ãå€éã«å«ã¿ã
ãããŠããšãã°ããããã®ååšã«ãããŠåã³é žå
ããããããŠãããã®è§Šåªãšãã€ããã«åå¿ã«æ»
ãããã ãã®çºæã«ããæçµçæç©ïŒãŠã¬ã¿ã³ïŒã¯ã殺
è«å€ãšããŠããŸãã¯æ®ºè«å€ã®è£œé ã®ããã®äžé補
åãšããŠã®äœ¿çšã®ããã«é©åœã§ãããããããªã
ãããããã¯ãããã«ããã€ãœã·ã¢ããŒããã€ã
ãããã®åºçºåæãšããŠäž»ãšããŠèå³ããããã€
ãœã·ã¢ããŒãã®ãã®è£œé ã¯ãã®çºæã«ããæçµç
æç©ã®ç±å解ã«ããå ¬ç¥ã®ããæ¹ã«ãããŠè¡ãªã
ããã ãã®çºæã«ããæ¹æ³ã¯ä»¥äžã®å®æœäŸã«ãã説æ
ããããããã®çºæã¯å®æœäŸã«é瀺ãããæ¡ä»¶ã«
å¶éããããã®ã§ã¯ãªãããŠã¬ã¿ã³åéã¯ããã
ãã®å Žåãã¢ã«ïŒ ã«ãããŠäœ¿çšãããã¢ãã³ã«å¯Ÿ
ãããã®ã§ããã äŸ ïŒ ïŒè§Šåªæåe2ã䜿çšããªãæ¯èŒäŸïŒ 次ã®çµæãæããæ··åç©474ïœããšãã¡ã«åŒã
ã®1.3Lã®çŽéŒè£œãªãŒãã¯ã¬ãŒãã«å°å ¥ãããã é ¢é žãã©ãžãŠã 42ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 211ppm ãšã¿ããŒã« 91.4ééïŒ ã¢ããªã³ 8.6ééïŒ 100barã®äžé žåççŽ ããã³25barã®ç©ºæ°ã宀枩
ã«ãããŠãªãŒãã¯ã¬ãŒãäžã«å°å ¥ãããããªãŒã
ã¯ã¬ãŒãã®å 容ç©ã¯æ¹æããªãã180âã«å ç±ã
ãããããŠãã®æž©åºŠã§ïŒæéåå¿ãç¶ããã宀枩
ã«ãŸã§å·åŽããåŸããªãŒãã¯ã¬ãŒãã¯ææ°ããã
ãããŠç¬¬ïŒã®åæ§ãªåå¿ã®æ®µéãæ°ããCOïŒç©º
æ°æ··åç©ã«ãã€ãŠè¡ãªããããããããã«ãã¢ã
ãªã³ã«å¯Ÿããã»ãŒ1.4é žååœéã®å šéã倧æ°äžã®
é žçŽ ã®åœ¢ã«ãããŠå°å ¥ããããã¬ã¹ã¯ãããã°ã©
ãã€ãŒã«ãã液ç¶åå¿æ··åç©ã®åæã¯ããšãã«ãŠ
ã¬ã¿ã³ã®åéã¯äœ¿çšãããã¢ããªã³ã«å¯ŸããŠ4.5
ïŒ ã«ãªãããšã瀺ãã äŸ ïŒâïŒ ãããã®äŸã¯äŸïŒãšã®æ¯èŒã«ãã觊åªæåe2ã®
觊åªæŽ»æ§ã瀺ããäŸïŒããïŒãŸã§ã«ãããŠè§Šåªæ
åe2ã¯ããã€ãååç©ã§ããããäŸïŒããïŒãŸã§
ã«ãããŠããã¯ããã€ãååç©ã®äºåç段éã§ã
ããæ段ã¯äŸïŒãšåæ§ã§ããã次ã®çµæã®æ··åç©
483ïœã䜿çšãããã é ¢é žãã©ãžãŠã 41ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 207ppm 觊åªæåe2 1.8ééïŒ ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ çµæã¯ç¬¬ïŒè¡šã«è¿°ã¹ãããã
ãè¡šã
äŸ 10
æ段ã¯æ¬¡ã®çµæã®æ··åç©487ïœã䜿çšããäŸïŒ
ã«ããããšåæ§ã§ããã é ¢é žãã©ãžãŠã 41ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 206ppm ïœâããã©ã¯ãããã³ãŸããã³
1.7ééïŒ ïŒ®ïŒïŒ®âãžãšãã«ã¢ããªã³ 0.8ééïŒ ãšã¿ããŒã« 89.0ééïŒ ã¢ããªã³ 8.4ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 72.6ïŒ äŸ 11 æ段ã¯æ¬¡ã®çµæã®æ··åç©483ïœã䜿çšããäŸïŒ
ã«èšèŒãããã®ãšåæ§ã§ããã é ¢é žãã©ãžãŠã 41ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 207ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ ãšã¿ããŒã« 48.3ééïŒ ã¢ããªã³ 8.4ééïŒ ãªã«ãâãžã¯ãããã³ãŒã³41.5ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 71.8ïŒ äŸ 12â17 ãããã®äŸã¯è§Šåªæåe1ãšããŠçš®ã ã®è²Žéå±ã®
觊åªæŽ»æ§ã瀺ãããã®æ段ã¯æ¬¡ã®çµæãæããå
å¿æ··åç©483ïœã䜿çšãããããšãé€ããŠäŸïŒã«
èšèŒããããšåæ§ã§ããã 觊åªæåe1ïŒ 104ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 207ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ åŸãããçµæã¯ç¬¬ïŒè¡šã«è¿°ã¹ããããäŸ12ã¯ã
ã®çºæã«ãã觊åªæåe1ãªãã®æ¯èŒäŸã§ããã
ã«ããããšåæ§ã§ããã é ¢é žãã©ãžãŠã 41ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 206ppm ïœâããã©ã¯ãããã³ãŸããã³
1.7ééïŒ ïŒ®ïŒïŒ®âãžãšãã«ã¢ããªã³ 0.8ééïŒ ãšã¿ããŒã« 89.0ééïŒ ã¢ããªã³ 8.4ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 72.6ïŒ äŸ 11 æ段ã¯æ¬¡ã®çµæã®æ··åç©483ïœã䜿çšããäŸïŒ
ã«èšèŒãããã®ãšåæ§ã§ããã é ¢é žãã©ãžãŠã 41ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 207ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ ãšã¿ããŒã« 48.3ééïŒ ã¢ããªã³ 8.4ééïŒ ãªã«ãâãžã¯ãããã³ãŒã³41.5ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 71.8ïŒ äŸ 12â17 ãããã®äŸã¯è§Šåªæåe1ãšããŠçš®ã ã®è²Žéå±ã®
觊åªæŽ»æ§ã瀺ãããã®æ段ã¯æ¬¡ã®çµæãæããå
å¿æ··åç©483ïœã䜿çšãããããšãé€ããŠäŸïŒã«
èšèŒããããšåæ§ã§ããã 觊åªæåe1ïŒ 104ppm é ¢é žç¬¬ïŒé ïŒæ°Žåç© 207ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ åŸãããçµæã¯ç¬¬ïŒè¡šã«è¿°ã¹ããããäŸ12ã¯ã
ã®çºæã«ãã觊åªæåe1ãªãã®æ¯èŒäŸã§ããã
ãè¡šã
äŸ 18
ãã®äŸã¯ã觊åªæåe1ããã³e2ã觊åªæåe3ã
ãã³e4ã®äžååšäžã«ãããŠãããŠã¬ã¿ã³çæåå¿
ã觊åªããããšã瀺ãããã®æ段ã¯æ¬¡ã®çµæã®å
å¿æ··åç©482ïœã䜿çšãããããšãé€ããŠäŸïŒã«
èšèŒããããšåæ§ã§ããã å¡©åãã©ãžãŠã 44ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 54.6ïŒ äŸ 19â23 æ段ã¯æ¬¡ã®çµæã®æ··åç©223ïœãå ¥ãã0.7LçŽ
éŒãªãŒãã¯ã¬ãŒãã䜿çšãããããšãé€ããŠäŸïŒ
ã«èšèŒããããšåæ§ã§ããã å¡©åãã©ãžãŠã 22ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ è§Šåªæåe3ïŒ 90ppm ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ çµæã¯è¡šïŒã«ç€ºãããã
ãã³e4ã®äžååšäžã«ãããŠãããŠã¬ã¿ã³çæåå¿
ã觊åªããããšã瀺ãããã®æ段ã¯æ¬¡ã®çµæã®å
å¿æ··åç©482ïœã䜿çšãããããšãé€ããŠäŸïŒã«
èšèŒããããšåæ§ã§ããã å¡©åãã©ãžãŠã 44ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 54.6ïŒ äŸ 19â23 æ段ã¯æ¬¡ã®çµæã®æ··åç©223ïœãå ¥ãã0.7LçŽ
éŒãªãŒãã¯ã¬ãŒãã䜿çšãããããšãé€ããŠäŸïŒ
ã«èšèŒããããšåæ§ã§ããã å¡©åãã©ãžãŠã 22ppm ïœâããã©ã¯ãããã³ãŸããã³
1.8ééïŒ è§Šåªæåe3ïŒ 90ppm ãšã¿ããŒã« 89.8ééïŒ ã¢ããªã³ 8.4ééïŒ çµæã¯è¡šïŒã«ç€ºãããã
ãè¡šã
äŸ 24
ãã®äŸã¯å埪ç°ããã觊åªã®è§ŠåªæŽ»æ§ã瀺ãã
æ²ãã³ããåºäœã¯äŸïŒã«ãããŠèšèŒããããšåæ§
ã«åŸãããã¿ã€ãã®çæç©æ··åç©ããå»ããã
åŒç¶ããŠ50âã«ãããŠä¹Ÿç¥ãããã次ã®çµæãæ
ããæ··åç©111ïœã0.3LçŽéŒè£œãªãŒãã¯ã¬ãŒãã
çšããäŸïŒã«ããããšåãæ¡ä»¶ã®äžã§åå¿ãã
ãã ååããã觊åªæ··åç© 8.4ééïŒ ãšã¿ããŒã« 89.8ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 62.4ïŒ äŸ 25â29 次ã®çµæã®æ··åç©111.4ïœã0.3LçŽéŒè£œãªãŒã
ã¯ã¬ãŒãã«å ¥ããããã é ¢é žãã©ãžãŠã 90ppm é ¢é žé ïŒæ°Žåç© 450ppm ããã©ã¯ããâïœâãã³ãŸããã³
1.8ééïŒ ã¢ããªã³ 8.4ééïŒ ããããã·æåïœïŒïŒè¡šïŒåç §ïŒ
89.8ééïŒ äžé žåççŽ 100barã空æ°25barã宀枩ã«ãããŠ
å°å ¥ããããããããã«ã¢ããªã³ã«å¯ŸããŠã»ãŒ
0.7é žååœéã倧æ°é žçŽ ã®åœ¢ã«ãããŠå°å ¥ãããã
ãªãŒãã¯ã¬ãŒãã®å 容ç©ã¯180âã«ãããŠïŒæé
åå¿ãç¶ãããå·åŽåŸã次ã®ãŠã¬ã¿ã³åéãã¬ã¹
ã¯ãããã°ã©ãã€ãŒã«ããåæã«åŸã€ãŠåŸãã
ãã
æ²ãã³ããåºäœã¯äŸïŒã«ãããŠèšèŒããããšåæ§
ã«åŸãããã¿ã€ãã®çæç©æ··åç©ããå»ããã
åŒç¶ããŠ50âã«ãããŠä¹Ÿç¥ãããã次ã®çµæãæ
ããæ··åç©111ïœã0.3LçŽéŒè£œãªãŒãã¯ã¬ãŒãã
çšããäŸïŒã«ããããšåãæ¡ä»¶ã®äžã§åå¿ãã
ãã ååããã觊åªæ··åç© 8.4ééïŒ ãšã¿ããŒã« 89.8ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 62.4ïŒ äŸ 25â29 次ã®çµæã®æ··åç©111.4ïœã0.3LçŽéŒè£œãªãŒã
ã¯ã¬ãŒãã«å ¥ããããã é ¢é žãã©ãžãŠã 90ppm é ¢é žé ïŒæ°Žåç© 450ppm ããã©ã¯ããâïœâãã³ãŸããã³
1.8ééïŒ ã¢ããªã³ 8.4ééïŒ ããããã·æåïœïŒïŒè¡šïŒåç §ïŒ
89.8ééïŒ äžé žåççŽ 100barã空æ°25barã宀枩ã«ãããŠ
å°å ¥ããããããããã«ã¢ããªã³ã«å¯ŸããŠã»ãŒ
0.7é žååœéã倧æ°é žçŽ ã®åœ¢ã«ãããŠå°å ¥ãããã
ãªãŒãã¯ã¬ãŒãã®å 容ç©ã¯180âã«ãããŠïŒæé
åå¿ãç¶ãããå·åŽåŸã次ã®ãŠã¬ã¿ã³åéãã¬ã¹
ã¯ãããã°ã©ãã€ãŒã«ããåæã«åŸã€ãŠåŸãã
ãã
ãè¡šã
äŸ 30
次ã®çµæã®æ··åç©129.4ïœã0.3LçŽéŒè£œãªãŒã
ã¯ã¬ãŒãã«å°å ¥ãããã é ¢é žãã©ãžãŠã 31ppm é ¢é žé ïŒæ°Žåç© 232ppm ããã©ã¯ããâïœâãã³ãŸããã³
1.5ééïŒ ããªãžã³ 5.4ééïŒ ïœâãã³ãŸããã³ 8.5ééïŒ ïŒ0.1ã¢ã«ïŒ ã¢ããªã³ 7.3ééïŒ ïŒ0.1ã¢ã«ïŒ ãšã¿ããŒã« 77.3ééïŒ CO120barã宀枩ã«ãããŠå°å ¥ãããã180âã«
ãããïŒæéã®åå¿æéåŸãããšãã«ãŠã¬ã¿ã³ã®
åéã¯ãã¬ã¹ã¯ãããã°ã©ãã€ãŒã«ãã34ïŒ ã«ãª
ãã äŸ 31 æ段ã¯æ¬¡ã®çµæã®åºçºæ··åç©127.8ïœãçšãã
äŸ31ã«èšèŒããããšåæ§ã§ããã é ¢é žãã©ãžãŠã 31ppm ããã©ã¯ããâïœâãã³ãŸããã³
1.6ééïŒ å¡©å第ïŒé 5.5ééïŒ ïŒ0.05ã¢ã«ïŒ é žå第ïŒé 3.4ééïŒ ïŒ0.05ã¢ã«ïŒ ããªãžã³ 3.9ééïŒ ã¢ããªã³ 7.4ééïŒ ïŒ0.1ã¢ã«ïŒ ãšã¿ããŒã« 78.2ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 40ïŒ äŸ 32 次ã®çµæã®æ··åç©216.7ïœã0.7LçŽéŒè£œãªãŒã
ã¯ã¬ãŒãäžã«å°å ¥ãããã é ¢é žãã©ãžãŠã 50ppm é ¢é žé ïŒæ°Žåç© 250ppm ïŒïŒïŒâãžã¯ãããããããã³
2.2ééïŒ ç¬¬ïŒçŽããã«ã¢ãã³ 5.5ééïŒ ãšã¿ããŒã« 92.3ééïŒ CO100barããã³ç©ºæ°25barã宀枩ã«ãããŠå°
å ¥ããããããã«ãã第ïŒçŽããã«ã¢ãã³ã«å¯Ÿã
ãŠã»ãŒïŒïŒïŒé žååœéã倧æ°é žçŽ ã®åœ¢ã«ãããŠå°
å ¥ãããããªãŒãã¯ã¬ãŒãã®å 容ç©ã¯180âã«ã
ããŠïŒæéæ¹æããªããåå¿ãç¶ãããå·åŽåŸã
ã¬ã¹ã¯ãããã°ã©ãã€ãŒã«ããåæã¯32ïŒ ã®ïŒ®â
第ïŒçŽããã«âïœâãšãã«ãŠã¬ã¿ã³ã®åéã瀺
ãã
ã¯ã¬ãŒãã«å°å ¥ãããã é ¢é žãã©ãžãŠã 31ppm é ¢é žé ïŒæ°Žåç© 232ppm ããã©ã¯ããâïœâãã³ãŸããã³
1.5ééïŒ ããªãžã³ 5.4ééïŒ ïœâãã³ãŸããã³ 8.5ééïŒ ïŒ0.1ã¢ã«ïŒ ã¢ããªã³ 7.3ééïŒ ïŒ0.1ã¢ã«ïŒ ãšã¿ããŒã« 77.3ééïŒ CO120barã宀枩ã«ãããŠå°å ¥ãããã180âã«
ãããïŒæéã®åå¿æéåŸãããšãã«ãŠã¬ã¿ã³ã®
åéã¯ãã¬ã¹ã¯ãããã°ã©ãã€ãŒã«ãã34ïŒ ã«ãª
ãã äŸ 31 æ段ã¯æ¬¡ã®çµæã®åºçºæ··åç©127.8ïœãçšãã
äŸ31ã«èšèŒããããšåæ§ã§ããã é ¢é žãã©ãžãŠã 31ppm ããã©ã¯ããâïœâãã³ãŸããã³
1.6ééïŒ å¡©å第ïŒé 5.5ééïŒ ïŒ0.05ã¢ã«ïŒ é žå第ïŒé 3.4ééïŒ ïŒ0.05ã¢ã«ïŒ ããªãžã³ 3.9ééïŒ ã¢ããªã³ 7.4ééïŒ ïŒ0.1ã¢ã«ïŒ ãšã¿ããŒã« 78.2ééïŒ ããšãã«ãŠã¬ã¿ã³ã®åé 40ïŒ äŸ 32 次ã®çµæã®æ··åç©216.7ïœã0.7LçŽéŒè£œãªãŒã
ã¯ã¬ãŒãäžã«å°å ¥ãããã é ¢é žãã©ãžãŠã 50ppm é ¢é žé ïŒæ°Žåç© 250ppm ïŒïŒïŒâãžã¯ãããããããã³
2.2ééïŒ ç¬¬ïŒçŽããã«ã¢ãã³ 5.5ééïŒ ãšã¿ããŒã« 92.3ééïŒ CO100barããã³ç©ºæ°25barã宀枩ã«ãããŠå°
å ¥ããããããã«ãã第ïŒçŽããã«ã¢ãã³ã«å¯Ÿã
ãŠã»ãŒïŒïŒïŒé žååœéã倧æ°é žçŽ ã®åœ¢ã«ãããŠå°
å ¥ãããããªãŒãã¯ã¬ãŒãã®å 容ç©ã¯180âã«ã
ããŠïŒæéæ¹æããªããåå¿ãç¶ãããå·åŽåŸã
ã¬ã¹ã¯ãããã°ã©ãã€ãŒã«ããåæã¯32ïŒ ã®ïŒ®â
第ïŒçŽããã«âïœâãšãã«ãŠã¬ã¿ã³ã®åéã瀺
ãã
Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ ïœ ç¬¬ïŒçŽã¢ãã³ã ïœ å°ãªããšãïŒã€ã®ããããã·ã«åºãå«ãåå
ç©ããã³ ïœ äžé žåççŽ ãš ïœ é žåå€ããã³ïŒãŸãã¯ ïœ å çŽ ã®åšæè¡šã®ç¬¬å¯æããã®å°ãªããšãïŒ
ã€ã®è²Žéå±ããã³ïŒãŸãã¯è²Žéå±ååç©ãå«ã
觊åªç³»ã®ååšäžã« åå¿ãããããšã«ãã€ãŠãŠã¬ã¿ã³ã補é ããæ¹
æ³ã«ãããŠã åå¿ãããïŒã€ã®æåãšããŠå°ãªããšãïŒã€ã®
é žåããããã€ãååç©ããã³ïŒãŸãã¯åå¿æ¡ä»¶
äžã«é žåããããã€ãååç©ã«è»¢æãããå°ãªã
ãšãïŒã€ã®ååç©ãå«ã觊åªç³»ïœ ã®ååšäžã«è¡ãª
ãããããšãç¹åŸŽãšããæ¹æ³ã ïŒ ååç¶é žçŽ ããã³ïŒãŸãã¯å€§ããã€ãªã³æ§ã®
ç¡æ©é žåå€ããã³ïŒãŸãã¯é žåããããã€ãåå
ç©ãé žåå€ïœãšããŠäœ¿çšãããããšãç¹åŸŽãšãã
ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ äœ¿çšããã觊åªç³»ïœ ãããïŒã€ã®æåãšããŠ
CrïŒMnïŒCoïŒCuããã³Mgãããªã矀ã®å çŽ ã®
å°ãªããšãïŒã€ã®ååç©ã§ãã€ãŠãåå¿æ¡ä»¶äžã«
é žåéå åå¿ãããããã®ãå«ã觊åªç³»ã§ããã
ãšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ãŸãã¯ç¬¬ïŒ
é ã«èšèŒã®æ¹æ³ã ïŒ äœ¿çšããã觊åªç³»ïœ ãããïŒã€æåãšããŠå°
ãªããšãïŒã€ã®ç¬¬ïŒçŽã¢ãã³ãå«ã觊åªç³»ã§ãã
ããšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã第ïŒé
ã®ããããã«èšèŒã®æ¹æ³ã ïŒ äœ¿çšããã觊åªç³»ïœ ãåå¿æ··åç©ã®å šééã«
察ããŠè²Žéå±ãšããŠè¡šãããã5ppmãã100ppm
ã®å°ãªããšãïŒã€ã®è²Žéå±ããã³ïŒãŸãã¯å°ãªã
ãšãïŒã€ã®è²Žéå±ååç©ãå«ã觊åªç³»ã§ããããš
ãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã第ïŒé ã®ã
ãããã«èšèŒã®æ¹æ³ã ïŒ äœ¿çšããã觊åªç³»ïœ ãåå¿æ··åç©ã®å šééã«
察ããŠ0.1ããïŒééïŒ ã®å°ãªããšãïŒã€ã®é žå
ããããã€ãååç©ããã³ïŒãŸãã¯åå¿æ¡ä»¶ã®äž
ã§é žåããããã€ãååç©ã«è»¢æãããå°ãªããš
ãïŒã€ã®ååç©ãå«ã觊åªç³»ã§ããããšãç¹åŸŽãš
ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã第ïŒé ã®ããããã«
èšèŒã®æ¹æ³ã ïŒ äœ¿çšããã觊åªç³»ïœ ãåå¿æ··åç©ã®å šééã«
察ããŠ0.1ééïŒ ãŸã§ã®CrïŒMnïŒCoïŒCuããã³
Mgãããªã矀ã®å çŽ ã®ååç©ã§ãã€ãŠãåå¿æ¡
件ã®äžã§é žåéå åå¿ãããããã®ããã³ïŒãŸã
ã¯10ééïŒ ãŸã§ã®ç¬¬ïŒçŽã¢ãã³ãå«ã觊åªç³»ã§ã
ãããšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã第ïŒ
é ã®ããããã«èšèŒã®æ¹æ³ã ïŒ åå¿ãïŒãã500barãŸã§ã®ç¯å²ã«ãããå§
åããã³100âãã250âãŸã§ã®ç¯å²ã«ããã枩床
ã«ãããŠè¡ãªãããããšãç¹åŸŽãšããç¹èš±è«æ±ã®
ç¯å²ç¬¬ïŒé ã第ïŒé ã®ããããã«èšèŒã®æ¹æ³ã ïŒ åå¿ãåå¿æ··åç©ã®å šééã«å¯ŸããŠ80ééïŒ
ãŸã§ã®äžæŽ»æ§æº¶åªã®ååšäžã«ãããŠè¡ãªãããã
ãšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã第ïŒé ã®
ããããã«èšèŒã®æ¹æ³ã ïŒïŒ æçµçæç©ãšããŠåŸããããŠã¬ã¿ã³ãä»»æ
çã«éå ããã圢ã«ãããé žåå€ãå«ã觊åªç³»ïœ
ããèžçããã³ïŒãŸãã¯æ¿Ÿéã«ããåé¢ãããã
ããŠè§Šåªç³»ïœ ãä»»æçã«ãéå ããã圢ã«ãããŠ
ä»»æçã«ååšããé žåå€ã®åé žååŸã«å䜿çšãã
ãããšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã第ïŒ
é ã®ããããã«èšèŒã®æ¹æ³ã
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803046982 DE3046982A1 (de) | 1980-12-12 | 1980-12-12 | Verfahren zur herstellung von urethanen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57126459A JPS57126459A (en) | 1982-08-06 |
| JPH0222744B2 true JPH0222744B2 (ja) | 1990-05-21 |
Family
ID=6119063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56197769A Granted JPS57126459A (en) | 1980-12-12 | 1981-12-10 | Manufacture of polyurethane |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4582923A (ja) |
| EP (1) | EP0054218B1 (ja) |
| JP (1) | JPS57126459A (ja) |
| DE (2) | DE3046982A1 (ja) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806674A (en) * | 1985-02-20 | 1989-02-21 | E. I. Du Pont De Nemours And Company | Preparation of urethanes by oxidative carbonylation of amines using copper carboxylates as oxidants |
| US4876379A (en) * | 1987-09-21 | 1989-10-24 | Amoco Corporation | Oxidative alkoxycarbonylation of amines and amine derivatives |
| US5502241A (en) * | 1990-02-06 | 1996-03-26 | Council Of Scientific & Industrial Research | Process for the preparation of alkyl carbamates |
| US5194660A (en) * | 1990-12-21 | 1993-03-16 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing carbamates and isocyanates |
| US5233010A (en) * | 1992-10-15 | 1993-08-03 | Monsanto Company | Process for preparing isocyanate and carbamate ester products |
| US5298651A (en) * | 1992-10-15 | 1994-03-29 | Monsanto Company | Process for preparing isocyanates using phosphazine catalysts |
| US5349081A (en) * | 1993-01-21 | 1994-09-20 | Monsanto Company | Process for preparing isocyanates |
| US5451697A (en) * | 1993-12-27 | 1995-09-19 | Monsanto Company | Process for preparing isocyanates |
| DE10250249A1 (de) * | 2002-10-28 | 2004-05-13 | Sgl Carbon Ag | Mischungen fÌr WÀrmespeicher |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641092A (en) * | 1966-11-25 | 1972-02-08 | Hercules Inc | Isocyanate synthesis from amines and carbon monoxide catalyzed by pdcl2 |
| DE2808980A1 (de) * | 1978-03-02 | 1979-09-13 | Bayer Ag | Verfahren zur herstellung von urethanen |
| DE2838754A1 (de) * | 1978-09-06 | 1980-03-20 | Bayer Ag | Verfahren zur herstellung von urethanen |
| DE2908250A1 (de) * | 1979-03-02 | 1980-09-11 | Bayer Ag | Verfahren zur herstellung von urethanen |
| DE2908251A1 (de) * | 1979-03-02 | 1980-09-11 | Bayer Ag | Verfahren zur herstellung von urethanen |
| DE2908252A1 (de) * | 1979-03-02 | 1980-09-11 | Bayer Ag | Verfahren zur herstellung von urethanen |
| DE2910132A1 (de) * | 1979-03-15 | 1980-09-25 | Basf Ag | Verfahren zur herstellung von aromatischen urethanen |
| US4266070A (en) * | 1979-05-25 | 1981-05-05 | Halcon Research And Development Corp. | Catalytic process for the manufacture of urethanes |
| US4260781A (en) * | 1979-05-25 | 1981-04-07 | Halcon Research And Development Corp. | Process for the manufacture of carbamates |
| US4251667A (en) * | 1979-06-06 | 1981-02-17 | Atlantic Richfield Company | Process for the preparation of aromatic urethanes |
| DE2945961A1 (de) * | 1979-11-14 | 1981-06-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur rueckfuehrung des edelmetallkatalysators zur herstellung aromatischer urethane |
-
1980
- 1980-12-12 DE DE19803046982 patent/DE3046982A1/de not_active Withdrawn
-
1981
- 1981-12-01 EP EP81110031A patent/EP0054218B1/de not_active Expired
- 1981-12-01 DE DE8181110031T patent/DE3166521D1/de not_active Expired
- 1981-12-10 JP JP56197769A patent/JPS57126459A/ja active Granted
-
1985
- 1985-05-17 US US06/735,249 patent/US4582923A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3046982A1 (de) | 1982-07-15 |
| JPS57126459A (en) | 1982-08-06 |
| EP0054218A1 (de) | 1982-06-23 |
| DE3166521D1 (en) | 1984-11-08 |
| EP0054218B1 (de) | 1984-10-03 |
| US4582923A (en) | 1986-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4297501A (en) | Process for the preparation of urethanes | |
| EP0266222B1 (en) | High purity process for the preparation of 4,6-diamino-1,3-benzenediol | |
| EP0000563B1 (en) | Process for preparing aromatic urethanes | |
| JPH0222744B2 (ja) | ||
| US4186269A (en) | Process for producing an aromatic urethane | |
| EP0312931B1 (en) | Process for the preparation of amino-1,3 benzenediol | |
| US4134880A (en) | Process for producing an aromatic urethane from nitro compounds, hydroxyl compounds and carbon monoxide using metal-Lewis acid-ammonia catalyst systems | |
| CA1192570A (en) | Process for the preparation of urethanes | |
| CA1133008A (en) | Process for the production of urethanes | |
| US4304922A (en) | Process for the preparation of urethane | |
| US5001265A (en) | Aqueous reduction process for halo-nitro-phenols | |
| US4976679A (en) | Process for producing a urethane and a carbonic acid ester | |
| US4678856A (en) | Method of manufacturing aromatic urethane and intermediate product thereof | |
| CA1291155C (en) | Process for the preparation of carbamates | |
| EP0359519B1 (en) | A process for producing carbamic acid esters | |
| JPS617246A (ja) | ãããè³éŠæååç©ããã®è³éŠæãŠã¬ã¿ã³é¡ã®è£œæ³ | |
| US5068384A (en) | Phosphate salts of AB-polybenzoxazole monomer | |
| EP0029460B1 (en) | Process for preparing aromatic urethane | |
| BE1013489A6 (fr) | Procede pour la preparation de carbamates aromatiques a partir de composes nitro-aromatiques. | |
| JPS5811943B2 (ja) | è³éŠæãŠã¬ã¿ã³ååç©ã®è£œé æ¹æ³ | |
| JPS60193958A (ja) | è³éŠæãŠã¬ã¿ã³ã®è£œé æ¹æ³ | |
| JPS5811942B2 (ja) | è³éŠæãŠã¬ã¿ã³ã®ç²Ÿè£œæ¹æ³ | |
| US5117036A (en) | Preparation of aromatic carbamates | |
| JPS61191664A (ja) | è³éŠæã«ã«ãããé žã¢ãªâã«ãšã¹ãã«ã®è£œæ³ | |
| SK140689A3 (en) | Preparation method of the primary aromatic amines and/or diamines |