JPS5814423B2 - 塩素化芳香族アミンの製造法 - Google Patents
塩素化芳香族アミンの製造法Info
- Publication number
- JPS5814423B2 JPS5814423B2 JP51131838A JP13183876A JPS5814423B2 JP S5814423 B2 JPS5814423 B2 JP S5814423B2 JP 51131838 A JP51131838 A JP 51131838A JP 13183876 A JP13183876 A JP 13183876A JP S5814423 B2 JPS5814423 B2 JP S5814423B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- hydrogenation
- charcoal
- sulfide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000004982 aromatic amines Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229910000510 noble metal Inorganic materials 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims description 9
- 150000003464 sulfur compounds Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000003112 inhibitor Substances 0.000 description 22
- 238000005984 hydrogenation reaction Methods 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003610 charcoal Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 150000003568 thioethers Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- -1 chlorinated aromatic nitro compounds Chemical class 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000010970 precious metal Substances 0.000 description 4
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- DMGFVJVLVZOSOE-UHFFFAOYSA-N 3-amino-4-chlorobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1Cl DMGFVJVLVZOSOE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006298 dechlorination reaction Methods 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000002407 reforming Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- IBRBMZRLVYKVRF-UHFFFAOYSA-N 1,2,4-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1Cl IBRBMZRLVYKVRF-UHFFFAOYSA-N 0.000 description 1
- ZYJBTGNUWOMRBG-UHFFFAOYSA-N 1,2,5-trichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(Cl)=C1Cl ZYJBTGNUWOMRBG-UHFFFAOYSA-N 0.000 description 1
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
- VZDUQPHKUBZMLW-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC=C1 VZDUQPHKUBZMLW-UHFFFAOYSA-N 0.000 description 1
- JXQYHZAVIRPVKM-UHFFFAOYSA-N 1-chloro-2,5-dimethoxy-3-nitrobenzene Chemical compound COC1=CC(Cl)=C(OC)C([N+]([O-])=O)=C1 JXQYHZAVIRPVKM-UHFFFAOYSA-N 0.000 description 1
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- PCIHIUCCINHORT-UHFFFAOYSA-N 2,6-dichloro-3-nitrobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC([N+]([O-])=O)=C1Cl PCIHIUCCINHORT-UHFFFAOYSA-N 0.000 description 1
- FLZUSUKBKOZJLG-UHFFFAOYSA-N 2-(4-chloro-2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1[N+]([O-])=O FLZUSUKBKOZJLG-UHFFFAOYSA-N 0.000 description 1
- DLJPNXLHWMRQIQ-UHFFFAOYSA-N 2-chloro-1-methoxy-4-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C=C1Cl DLJPNXLHWMRQIQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- DKTRZBWXGOPYIX-UHFFFAOYSA-N 3-chloro-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C(Cl)=C1 DKTRZBWXGOPYIX-UHFFFAOYSA-N 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- FSGTULQLEVAYRS-UHFFFAOYSA-N 4,5-dichloro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O FSGTULQLEVAYRS-UHFFFAOYSA-N 0.000 description 1
- ABEUJUYEUCCZQF-UHFFFAOYSA-N 4-chloro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(Cl)=CC=C1[N+]([O-])=O ABEUJUYEUCCZQF-UHFFFAOYSA-N 0.000 description 1
- NSMZCUAVEOTJDS-UHFFFAOYSA-N 4-chloro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(Cl)=CC=C1[N+]([O-])=O NSMZCUAVEOTJDS-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
- QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 150000004887 dithianes Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- AAIMUHANAAXZIF-UHFFFAOYSA-L platinum(2+);sulfite Chemical compound [Pt+2].[O-]S([O-])=O AAIMUHANAAXZIF-UHFFFAOYSA-L 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000035484 reaction time Effects 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
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
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 |
|---|---|---|---|
| DE2549900A DE2549900C3 (de) | 1975-11-06 | 1975-11-06 | Verfahren zur Herstellung chlorierter aromatischer Amine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5259121A JPS5259121A (en) | 1977-05-16 |
| JPS5814423B2 true JPS5814423B2 (ja) | 1983-03-18 |
Family
ID=5961112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51131838A Expired JPS5814423B2 (ja) | 1975-11-06 | 1976-11-04 | 塩素化芳香族アミンの製造法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4059627A (enExample) |
| JP (1) | JPS5814423B2 (enExample) |
| BE (1) | BE848003A (enExample) |
| CH (1) | CH620419A5 (enExample) |
| DE (1) | DE2549900C3 (enExample) |
| FR (1) | FR2330669A1 (enExample) |
| GB (1) | GB1530338A (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000805A1 (en) * | 1977-08-13 | 1979-02-21 | The Clayton Aniline Company Limited | Catalytic hydrogenation process for the manufacture of chlorinated aromatic amines |
| US4297509A (en) * | 1980-03-25 | 1981-10-27 | Union Carbide Corporation | Process for preparing alkali metal salts 3-amino-2, 5-dichlorobenzoic acid |
| DE3042242A1 (de) | 1980-11-08 | 1982-06-09 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von m-halogensubstituierten anilinen |
| US4760187A (en) * | 1981-08-14 | 1988-07-26 | E. I. Du Pont De Nemours And Company | Process for reducing chloronitrobenzenes using ruthenium with a minor amount of platinum as the catalyst |
| US4500736A (en) * | 1982-09-02 | 1985-02-19 | Merck & Co., Inc. | Hydrogenation of 3-trichlorovinylnitrobenzene |
| JPS5955855A (ja) * | 1982-09-27 | 1984-03-31 | Mitsui Toatsu Chem Inc | ３，３′−ジアミノジフエニルメタンの製造方法 |
| JPS60130553A (ja) * | 1983-12-19 | 1985-07-12 | Central Glass Co Ltd | ４−クロロ−２−トリフルオロメチルアニリンの製造方法 |
| US4960936A (en) * | 1987-12-31 | 1990-10-02 | Ciba-Geigy Corporation | Process for the preparation of halogenated aromatic primary amines |
| DE3821013A1 (de) * | 1988-06-22 | 1989-12-28 | Hoechst Ag | Verfahren zur herstellung von 4-chlor-2,5-dimethoxyanilin |
| DE3824625A1 (de) * | 1988-07-20 | 1990-01-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur hydrierung von (alpha),(beta)-ungesaettigten ketonen |
| FR2649979B1 (fr) * | 1989-07-20 | 1992-01-17 | Rhone Poulenc Chimie | Procede d'hydrogenation de derives halogeno nitroaromatiques en presence d'un derive soufre |
| FR2664590B1 (fr) * | 1990-07-16 | 1994-04-01 | Rhone Poulenc Chimie | Procede d'hydrogenation de derives halogeno nitroaromatiques en presence d'un derive soufre. |
| EP0473552A1 (de) * | 1990-08-31 | 1992-03-04 | Ciba-Geigy Ag | Verfahren zur Herstellung von halogenierten aromatischen primären Aminen |
| US5432284A (en) * | 1993-09-08 | 1995-07-11 | G. D. Searle & Co. | Process for the preparation of heterocyclic alkylamide derivatives |
| DE4334432A1 (de) * | 1993-10-08 | 1995-04-13 | Hoechst Ag | Verfahren zur Herstellung von 5-Fluoranthranilsäurealkylestern und/oder 5-Fluoranthranilsäure |
| DE4339209A1 (de) * | 1993-11-17 | 1995-05-18 | Hoechst Ag | Verfahren zur Herstellung von substituierten Chinazolin-2,4-dionen |
| DE4428535A1 (de) * | 1994-08-12 | 1996-02-15 | Bayer Ag | Verfahren zur selektiven Herstellung von fluorierten aromatischen Aminen und fluorierte aromatische Amine mit besonders niedrigen Gehalten an defluorierten Anteilen |
| DE4441145A1 (de) * | 1994-11-18 | 1996-05-23 | Hoechst Ag | Verfahren zur Herstellung von substituierten Chinazolin-2,4-dionen |
| DE19543475A1 (de) * | 1995-11-22 | 1997-05-28 | Bayer Ag | Verfahren zur Herstellung von 2-Amino-6-chlorphenyl-alkylsulfanen und 2-Amino-6-chlorphenyl-isopropylsulfan |
| DE19630228A1 (de) * | 1996-07-26 | 1998-01-29 | Bayer Ag | Verfahren zur Herstellung von 2-Trifluormethoxy-anilin |
| US6034276A (en) * | 1999-03-22 | 2000-03-07 | Eastman Chemical Company | Process for preparing 1-chloro-2,4-diaminobenzene |
| JP5105296B2 (ja) | 2005-12-02 | 2012-12-26 | エヌ・イーケムキャット株式会社 | 官能基選択的水素化触媒、及び官能基選択的水素化方法 |
| JP2010501679A (ja) * | 2006-08-24 | 2010-01-21 | カリフォルニア インスティテュート オブ テクノロジー | 炭化水素を製造するための方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538161A (en) * | 1967-10-20 | 1970-11-03 | Uniroyal Inc | Reductive alkylation of aromatic amino compounds utilizing platinum metal selendies and tellurides as catalysts |
| DE1643379A1 (de) * | 1967-12-04 | 1971-05-27 | Bayer Ag | Verfahren zur Herstellung halogenierter aromatischer Amine |
| US3739026A (en) * | 1969-12-03 | 1973-06-12 | Goodyear Tire & Rubber | Reductive alkylation reactions using modified nickel catalyst systems |
| US3920743A (en) * | 1973-06-04 | 1975-11-18 | Hoechst Ag | Process of preparing aromatic amines |
| JPS5726262B2 (enExample) * | 1973-11-06 | 1982-06-03 |
-
1975
- 1975-11-06 DE DE2549900A patent/DE2549900C3/de not_active Expired
-
1976
- 1976-11-01 US US05/737,645 patent/US4059627A/en not_active Expired - Lifetime
- 1976-11-02 CH CH1382276A patent/CH620419A5/de not_active IP Right Cessation
- 1976-11-02 GB GB45503/76A patent/GB1530338A/en not_active Expired
- 1976-11-04 JP JP51131838A patent/JPS5814423B2/ja not_active Expired
- 1976-11-05 FR FR7633510A patent/FR2330669A1/fr active Granted
- 1976-11-05 BE BE2055428A patent/BE848003A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2549900B2 (de) | 1980-05-29 |
| FR2330669A1 (fr) | 1977-06-03 |
| US4059627A (en) | 1977-11-22 |
| DE2549900A1 (de) | 1977-05-12 |
| CH620419A5 (enExample) | 1980-11-28 |
| GB1530338A (en) | 1978-10-25 |
| JPS5259121A (en) | 1977-05-16 |
| DE2549900C3 (de) | 1981-02-05 |
| BE848003A (fr) | 1977-05-05 |
| FR2330669B1 (enExample) | 1981-07-10 |
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