GB832153A - Catalytic hydrogenation of the dinitro derivatives of toluene - Google Patents
Catalytic hydrogenation of the dinitro derivatives of tolueneInfo
- Publication number
- GB832153A GB832153A GB23830/58A GB2383058A GB832153A GB 832153 A GB832153 A GB 832153A GB 23830/58 A GB23830/58 A GB 23830/58A GB 2383058 A GB2383058 A GB 2383058A GB 832153 A GB832153 A GB 832153A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogenation
- dinitro
- iron
- dinitrocompound
- dinitrotoluenes
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title abstract 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title abstract 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 title 1
- GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical class CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 abstract 1
- XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical class CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 abstract 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 abstract 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 abstract 1
- 229910001018 Cast iron Inorganic materials 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000008367 deionised water Substances 0.000 abstract 1
- 229910021641 deionized water Inorganic materials 0.000 abstract 1
- VMMLSJNPNVTYMN-UHFFFAOYSA-N dinitromethylbenzene Chemical class [O-][N+](=O)C([N+]([O-])=O)C1=CC=CC=C1 VMMLSJNPNVTYMN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 159000000014 iron salts Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 abstract 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical class NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 abstract 1
- 238000003969 polarography Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002002 slurry Substances 0.000 abstract 1
- 229910001220 stainless steel Inorganic materials 0.000 abstract 1
- 239000010935 stainless steel Substances 0.000 abstract 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Diaminotoluenes are produced by the catalytic hydrogenation of the corresponding dinitrotoluenes in the molten state, the dinitrocompound used containing less than 500 parts per million, preferably less than 200 p.p.m., of nitrophenols or nitrocresols whereby the hydrogenation can be safely carried out at a temperature between 90 DEG and 135 DEG C. at ordinary or slightly elevated pressure, without the formation of tarry by-products. The dinitrocompound may be prepared by nitrating toluene or mono-nitrotoluene in stainless-steel equipment which does not introduce ionizable iron salts into the product. If cast-iron equipment is used for the nitration, the crude dinitro-compound must be washed with dilute nitric acid, to remove iron, prior to washing with alkali and water. The nitrophenol or nitrocresol content of the dinitro-compound can be determined by polarographic analysis. Examples 1, 2, 4 and 5 relate to the reduction of a mixture of 2,4- and 2,6-dinitrotoluenes to the corresponding tolylene diamines using a palladium-on-charcoal catalyst, which is introduced into the reactor in the form of a slurry in deionized water. In Example 5, a nickel-on-silica catalyst is used. Example 3 relates to the hydrogenation of 2,4-dinitrotoluene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US832153XA | 1957-07-30 | 1957-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB832153A true GB832153A (en) | 1960-04-06 |
Family
ID=22176916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23830/58A Expired GB832153A (en) | 1957-07-30 | 1958-07-24 | Catalytic hydrogenation of the dinitro derivatives of toluene |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB832153A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3093685A (en) * | 1960-10-21 | 1963-06-11 | Gen Aniline & Film Corp | Catalytic reduction of aromatic mononitro compounds |
| US3149161A (en) * | 1960-10-27 | 1964-09-15 | Gen Aniline & Film Corp | Catalytic reduction of 3-chloronitro benzene |
| EP0002308A1 (en) * | 1977-11-24 | 1979-06-13 | The Clayton Aniline Company Limited | Catalytic hydrogenation process for the manufacture of aromatic amines |
| US7026269B2 (en) | 2000-07-04 | 2006-04-11 | Basf Aktiengesellschaft | Metallic hydrogenation catalysts, production and use thereof |
| EP1935870A1 (en) | 2006-12-19 | 2008-06-25 | Bayer MaterialScience AG | Method for manufacturing toluylendiamines through catalytic hydration of dinitrotoluols |
| CN113563213A (en) * | 2021-08-30 | 2021-10-29 | 淄博晟亿弘新材料科技有限公司 | Preparation method of 3, 5-diaminobenzoic acid |
-
1958
- 1958-07-24 GB GB23830/58A patent/GB832153A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3093685A (en) * | 1960-10-21 | 1963-06-11 | Gen Aniline & Film Corp | Catalytic reduction of aromatic mononitro compounds |
| US3149161A (en) * | 1960-10-27 | 1964-09-15 | Gen Aniline & Film Corp | Catalytic reduction of 3-chloronitro benzene |
| EP0002308A1 (en) * | 1977-11-24 | 1979-06-13 | The Clayton Aniline Company Limited | Catalytic hydrogenation process for the manufacture of aromatic amines |
| US7026269B2 (en) | 2000-07-04 | 2006-04-11 | Basf Aktiengesellschaft | Metallic hydrogenation catalysts, production and use thereof |
| EP1935870A1 (en) | 2006-12-19 | 2008-06-25 | Bayer MaterialScience AG | Method for manufacturing toluylendiamines through catalytic hydration of dinitrotoluols |
| US7511176B2 (en) | 2006-12-19 | 2009-03-31 | Bayer Materialscience Ag | Process for the preparation of toluenediamines by catalytic hydrogenation of dinitrotoluenes |
| CN113563213A (en) * | 2021-08-30 | 2021-10-29 | 淄博晟亿弘新材料科技有限公司 | Preparation method of 3, 5-diaminobenzoic acid |
| CN113563213B (en) * | 2021-08-30 | 2024-03-22 | 淄博晟亿弘新材料科技有限公司 | Preparation method of 3, 5-diaminobenzoic acid |
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