CS204017B2 - Method of producing p-nitroso-diphenyl-hydroxylamines - Google Patents
Method of producing p-nitroso-diphenyl-hydroxylamines Download PDFInfo
- Publication number
- CS204017B2 CS204017B2 CS78167A CS16778A CS204017B2 CS 204017 B2 CS204017 B2 CS 204017B2 CS 78167 A CS78167 A CS 78167A CS 16778 A CS16778 A CS 16778A CS 204017 B2 CS204017 B2 CS 204017B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- reaction
- mol
- nitroso
- nitrosobenzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 18
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 239000003377 acid catalyst Substances 0.000 claims abstract description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 95
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 68
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 21
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 18
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- XVFKQAMBMSXMAQ-UHFFFAOYSA-N 1,1,1-trifluoropropane-2-sulfonic acid Chemical compound FC(F)(F)C(C)S(O)(=O)=O XVFKQAMBMSXMAQ-UHFFFAOYSA-N 0.000 claims 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 abstract description 55
- 239000002253 acid Substances 0.000 abstract description 22
- -1 aromatic sulfonic acids Chemical class 0.000 abstract description 4
- 239000000376 reactant Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 12
- 238000001035 drying Methods 0.000 description 10
- 239000005457 ice water Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229960001701 chloroform Drugs 0.000 description 9
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000006471 dimerization reaction Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- JAMGZOIOVGVZOI-UHFFFAOYSA-N (n-phenylanilino) nitrite Chemical class C=1C=CC=CC=1N(ON=O)C1=CC=CC=C1 JAMGZOIOVGVZOI-UHFFFAOYSA-N 0.000 description 4
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- TWLBRQVYXPMCFK-UHFFFAOYSA-N 1-methyl-2-nitrosobenzene Chemical compound CC1=CC=CC=C1N=O TWLBRQVYXPMCFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000447 dimerizing effect Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- JSEVUNYSFUYUEO-UHFFFAOYSA-N 1-fluoro-3-nitrosobenzene Chemical compound FC1=CC=CC(N=O)=C1 JSEVUNYSFUYUEO-UHFFFAOYSA-N 0.000 description 2
- NSGVPXKWKUZSAY-UHFFFAOYSA-N 1-nitro-2-nitrosobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=O NSGVPXKWKUZSAY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000270295 Serpentes Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IBSXAAOLHMGYLZ-UHFFFAOYSA-N methyl 2-nitrosobenzoate Chemical compound COC(=O)C1=CC=CC=C1N=O IBSXAAOLHMGYLZ-UHFFFAOYSA-N 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- CONCDOSRNXFJNN-UHFFFAOYSA-N 1,2-dipropylpyrrolidine Chemical class CCCC1CCCN1CCC CONCDOSRNXFJNN-UHFFFAOYSA-N 0.000 description 1
- ICYPOGVRNGUWNP-UHFFFAOYSA-N 1,3-dichloro-2-nitrosobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=O ICYPOGVRNGUWNP-UHFFFAOYSA-N 0.000 description 1
- OFQRRUGDGASXKM-UHFFFAOYSA-N 1,3-dimethyl-2-nitrosobenzene Chemical compound CC1=CC=CC(C)=C1N=O OFQRRUGDGASXKM-UHFFFAOYSA-N 0.000 description 1
- HDLCHVIFMRMBJP-UHFFFAOYSA-N 1,4-dichloro-2-nitrosobenzene Chemical compound ClC1=CC=C(Cl)C(N=O)=C1 HDLCHVIFMRMBJP-UHFFFAOYSA-N 0.000 description 1
- AYGXDXVGROLVJK-UHFFFAOYSA-N 1-chloro-2-nitrosobenzene Chemical compound ClC1=CC=CC=C1N=O AYGXDXVGROLVJK-UHFFFAOYSA-N 0.000 description 1
- ZNTJGNOQDHOIIX-UHFFFAOYSA-N 1-chloro-3-nitrosobenzene Chemical compound ClC1=CC=CC(N=O)=C1 ZNTJGNOQDHOIIX-UHFFFAOYSA-N 0.000 description 1
- RBKIPVPBQBMGNJ-UHFFFAOYSA-N 1-methoxy-2-nitrosobenzene Chemical compound COC1=CC=CC=C1N=O RBKIPVPBQBMGNJ-UHFFFAOYSA-N 0.000 description 1
- QMYICKNKPIKZIK-UHFFFAOYSA-N 1-nitroso-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=O)=C1 QMYICKNKPIKZIK-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000287219 Serinus canaria Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- POYFGNZHAOKCIC-UHFFFAOYSA-N benzene;nitrous acid Chemical compound ON=O.C1=CC=CC=C1 POYFGNZHAOKCIC-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BBLDUGKYPWLKPO-UHFFFAOYSA-N methanesulfonic acid;(n-phenylanilino) nitrite Chemical compound CS(O)(=O)=O.C=1C=CC=CC=1N(ON=O)C1=CC=CC=C1 BBLDUGKYPWLKPO-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- BKEPCQKPZRIPIH-UHFFFAOYSA-N n-(2-fluoro-4-nitrosophenyl)-n-(3-fluorophenyl)hydroxylamine Chemical compound C=1C=C(N=O)C=C(F)C=1N(O)C1=CC=CC(F)=C1 BKEPCQKPZRIPIH-UHFFFAOYSA-N 0.000 description 1
- ZRZFIXGPHKXFAR-UHFFFAOYSA-N n-(2-nitro-4-nitrosophenyl)-n-(3-nitrophenyl)hydroxylamine Chemical compound C=1C=C(N=O)C=C([N+]([O-])=O)C=1N(O)C1=CC=CC([N+]([O-])=O)=C1 ZRZFIXGPHKXFAR-UHFFFAOYSA-N 0.000 description 1
- IMMRRCMMCZUAFS-UHFFFAOYSA-N n-(3-methyl-4-nitrosophenyl)-n-(2-methylphenyl)hydroxylamine Chemical compound CC1=CC=CC=C1N(O)C1=CC=C(N=O)C(C)=C1 IMMRRCMMCZUAFS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NLRKCXQQSUWLCH-IDEBNGHGSA-N nitrosobenzene Chemical class O=N[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 NLRKCXQQSUWLCH-IDEBNGHGSA-N 0.000 description 1
- CYGSXDXRHXMAOV-UHFFFAOYSA-N o-cresol hydrogen sulfate Chemical compound CC1=CC=CC=C1OS(O)(=O)=O CYGSXDXRHXMAOV-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2703919A DE2703919C2 (de) | 1977-01-31 | 1977-01-31 | Verfahren zur Herstellung von p-Nitroso-diphenylhydroxylaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS204017B2 true CS204017B2 (en) | 1981-03-31 |
Family
ID=5999983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS78167A CS204017B2 (en) | 1977-01-31 | 1978-01-09 | Method of producing p-nitroso-diphenyl-hydroxylamines |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4129740A (en, 2012) |
| JP (1) | JPS5395927A (en, 2012) |
| BE (1) | BE863286A (en, 2012) |
| BR (1) | BR7800548A (en, 2012) |
| CA (1) | CA1106854A (en, 2012) |
| CH (1) | CH632231A5 (en, 2012) |
| CS (1) | CS204017B2 (en, 2012) |
| DD (1) | DD134517A5 (en, 2012) |
| DE (1) | DE2703919C2 (en, 2012) |
| ES (1) | ES465875A1 (en, 2012) |
| FR (1) | FR2378745B1 (en, 2012) |
| GB (1) | GB1560719A (en, 2012) |
| HU (1) | HU179106B (en, 2012) |
| IT (1) | IT1102812B (en, 2012) |
| NL (1) | NL7800276A (en, 2012) |
| PL (1) | PL110765B1 (en, 2012) |
| RO (1) | RO74630A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2961447D1 (en) * | 1978-08-18 | 1982-01-28 | Akzo Nv | Process for the preparation of p-nitroso-diphenylhydroxylamines |
| JPH05321449A (ja) * | 1992-05-18 | 1993-12-07 | Kokuyo Co Ltd | 床部材 |
| DE19922405A1 (de) * | 1999-05-14 | 2000-11-16 | Bayer Ag | Verfahren zur Herstellung von (4-Nitrosophenyl)phenylhydroxylamin |
| DE10055221A1 (de) | 2000-11-08 | 2002-05-29 | Bayer Ag | Verfahren zur Herstellung von 4-Aminodiphenylamin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1147237B (de) * | 1961-04-06 | 1963-04-18 | Bayer Ag | Verfahren zur Herstellung von N-Phenyl-N-(4-nitrosophenyl)-hydroxylamin |
| GB1257984A (en, 2012) * | 1969-04-24 | 1971-12-22 | ||
| US3933848A (en) * | 1971-07-28 | 1976-01-20 | Standard Oil Company | Process for the preparation of phenylamines and carbazoles |
-
1977
- 1977-01-31 DE DE2703919A patent/DE2703919C2/de not_active Expired
-
1978
- 1978-01-09 CS CS78167A patent/CS204017B2/cs unknown
- 1978-01-10 FR FR7800565A patent/FR2378745B1/fr not_active Expired
- 1978-01-10 NL NL7800276A patent/NL7800276A/xx not_active Application Discontinuation
- 1978-01-11 ES ES465875A patent/ES465875A1/es not_active Expired
- 1978-01-20 CH CH59778A patent/CH632231A5/de not_active IP Right Cessation
- 1978-01-23 IT IT47741/78A patent/IT1102812B/it active
- 1978-01-25 PL PL1978204212A patent/PL110765B1/pl unknown
- 1978-01-25 BE BE184609A patent/BE863286A/xx not_active IP Right Cessation
- 1978-01-27 DD DD78203454A patent/DD134517A5/xx unknown
- 1978-01-30 BR BR7800548A patent/BR7800548A/pt unknown
- 1978-01-30 HU HU78AO459A patent/HU179106B/hu unknown
- 1978-01-30 RO RO7893049A patent/RO74630A/ro unknown
- 1978-01-30 US US05/873,327 patent/US4129740A/en not_active Expired - Lifetime
- 1978-01-30 CA CA295,886A patent/CA1106854A/en not_active Expired
- 1978-01-31 GB GB3810/78A patent/GB1560719A/en not_active Expired
- 1978-01-31 JP JP980878A patent/JPS5395927A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1102812B (it) | 1985-10-07 |
| HU179106B (en) | 1982-08-28 |
| RO74630A (ro) | 1980-11-30 |
| GB1560719A (en) | 1980-02-06 |
| JPS6238346B2 (en, 2012) | 1987-08-17 |
| NL7800276A (nl) | 1978-08-02 |
| CH632231A5 (de) | 1982-09-30 |
| DD134517A5 (de) | 1979-03-07 |
| US4129740A (en) | 1978-12-12 |
| BE863286A (fr) | 1978-05-16 |
| FR2378745B1 (fr) | 1985-06-21 |
| BR7800548A (pt) | 1978-09-12 |
| DE2703919B1 (de) | 1978-07-27 |
| FR2378745A1 (fr) | 1978-08-25 |
| ES465875A1 (es) | 1978-09-16 |
| JPS5395927A (en) | 1978-08-22 |
| IT7847741A0 (it) | 1978-01-23 |
| DE2703919C2 (de) | 1979-03-29 |
| PL204212A1 (pl) | 1979-04-09 |
| CA1106854A (en) | 1981-08-11 |
| PL110765B1 (en) | 1980-07-31 |
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