DE1768518A1 - Herstellung aromatischer Amine - Google Patents
Herstellung aromatischer AmineInfo
- Publication number
- DE1768518A1 DE1768518A1 DE19681768518 DE1768518A DE1768518A1 DE 1768518 A1 DE1768518 A1 DE 1768518A1 DE 19681768518 DE19681768518 DE 19681768518 DE 1768518 A DE1768518 A DE 1768518A DE 1768518 A1 DE1768518 A1 DE 1768518A1
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- benzo
- titanium
- production
- aromatic amines
- 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.)
- Pending
Links
- 150000004982 aromatic amines Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 18
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 13
- 239000010936 titanium Substances 0.000 claims description 13
- 229910052719 titanium Inorganic materials 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 150000001502 aryl halides Chemical class 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000005915 ammonolysis reaction Methods 0.000 description 10
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
- SDUAXSKHZIJCSC-UHFFFAOYSA-N 4-chlorophenanthrene Chemical compound C1=CC=CC2=C3C(Cl)=CC=CC3=CC=C21 SDUAXSKHZIJCSC-UHFFFAOYSA-N 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- VQUOFRWKEZSLML-UHFFFAOYSA-N ClC1=CC=CC=C1.ClC1=CC=CC2=CC=CC=C12 Chemical compound ClC1=CC=CC=C1.ClC1=CC=CC2=CC=CC=C12 VQUOFRWKEZSLML-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910000464 lead oxide Inorganic materials 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-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
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- -1 aromatic halogen Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64039067A | 1967-05-22 | 1967-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768518A1 true DE1768518A1 (de) | 1971-11-18 |
Family
ID=24568049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768518 Pending DE1768518A1 (de) | 1967-05-22 | 1968-05-21 | Herstellung aromatischer Amine |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1768518A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1565987A (enrdf_load_stackoverflow) |
| GB (1) | GB1181914A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2536454C3 (de) * | 1975-08-16 | 1985-05-30 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von 2,4-Dinitroanilin |
| CN101343231B (zh) * | 2008-08-21 | 2011-12-07 | 苏州市罗森助剂有限公司 | 一种对硝基苯胺的生产方法 |
| WO2017006315A1 (en) * | 2015-07-05 | 2017-01-12 | Nayam Wings Ltd. | Wing-type sail system |
| CN109516921B (zh) * | 2018-11-12 | 2021-10-22 | 江苏扬农化工集团有限公司 | 一种制备对硝基苯胺的方法 |
-
1968
- 1968-05-21 FR FR1565987D patent/FR1565987A/fr not_active Expired
- 1968-05-21 GB GB24042/68A patent/GB1181914A/en not_active Expired
- 1968-05-21 DE DE19681768518 patent/DE1768518A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR1565987A (enrdf_load_stackoverflow) | 1969-05-02 |
| GB1181914A (en) | 1970-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0083442B1 (de) | Verfahren zur Herstellung von 2,4,6-Trichloranilin | |
| DE1768518A1 (de) | Herstellung aromatischer Amine | |
| EP0057861B1 (de) | Verfahren zur Herstellung von Nitroanilinen | |
| EP0057889B1 (de) | Verfahren zur Herstellung von 1-Alkyl-2-chlor-5-nitro-4-benzol-sulfonsäuren | |
| CH634825A5 (de) | Verfahren zur herstellung von p-hydroxyphenylglycin oder dessen n-alkyl- bzw. n,n-dialkylderivaten. | |
| EP0220135B1 (de) | Verfahren zur Herstellung von Chloranil | |
| EP0173202A2 (de) | Verfahren zur Herstellung von Chlor-o-nitroanilinen | |
| DE2831994A1 (de) | Verfahren zur herstellung von tobias- saeure | |
| DE1154799B (de) | Verfahren zur Herstellung von 4, 5-Dichlor- und 4, 5-Dibrom-naphthalin-1, 8-dicarbonsaeureanhydrid | |
| EP0070424B1 (de) | Verfahren zur Herstellung von N,N'-disubstituierten 3-Aminopropanamiden | |
| DE2424372C3 (de) | Verfahren zur Herstellung von Isonitrosoacetaniliden | |
| CH630596A5 (de) | Verfahren zur herstellung von 4-phenoxy-phenolen. | |
| DE2250106A1 (de) | Verfahren zur herstellung von 1,1'dianthrachinonylen | |
| DE2116159C3 (de) | Verfahren zur Herstellung von 4-Pyridylthio-essigsäure | |
| DE2613994A1 (de) | Verfahren zur herstellung von iminodiazetonitril | |
| DE2062040B2 (de) | Verfahren zur Überführung von Nitroimidazolen in ihre N-(2-Alkylthio)äthylderivate | |
| DE3115548A1 (de) | Verfahren zur herstellung von 1-alkylaminoanthrachinonen | |
| DE932125C (de) | Verfahren zur Umlagerung von Naphthalsaeure in Naphthalin-2, 6-dicarbonsaeure | |
| DE929191C (de) | Verfahren zur Herstellung von Aminocarbonsaeuren | |
| DE2405986C2 (de) | Verfahren zur Herstellung von reinen aromatischen o-Hydroxy-carbonsäurearylamiden | |
| DD205413A1 (de) | Verfahren zur herstellung von ammoniumtrioxalatoferrat (iii)-trihydrat | |
| DE1518818A1 (de) | Verfahren zur Herstellung von Guanidinderivaten | |
| DE1470090A1 (de) | Verfahren zur Herstellung von Derivaten der Naphthalsaeure | |
| DE1279684B (de) | Verfahren zur Herstellung von 4-Chlorsalicylsaeure | |
| DE2331791A1 (de) | Verfahren zur herstellung von aminohydroxyanthrachinonen |