GB596287A - Improvements in the production of aromatic amines - Google Patents
Improvements in the production of aromatic aminesInfo
- Publication number
- GB596287A GB596287A GB167444A GB167444A GB596287A GB 596287 A GB596287 A GB 596287A GB 167444 A GB167444 A GB 167444A GB 167444 A GB167444 A GB 167444A GB 596287 A GB596287 A GB 596287A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- water
- mono
- mixture
- reaction temperature
- 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 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 12
- 238000006243 chemical reaction Methods 0.000 abstract 8
- 239000003054 catalyst Substances 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 5
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical group [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 abstract 5
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 239000007788 liquid Substances 0.000 abstract 4
- 239000003610 charcoal Substances 0.000 abstract 3
- 150000002828 nitro derivatives Chemical class 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 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 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- -1 nitro hydrocarbons Chemical class 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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)
Abstract
<PICT:0596287/III/1> Aromatic amines are prepared by the reduction of mono-nitro-aromatic hydrocarbons with hydrogen in the presence of hydrogenation catalyst wherein the reaction temperature is controlled by introducing a mixture of the nitrohydrocarbons and liquid water into the reaction zone at a plurality of points and immediately vaporizing the water under the reaction temperature. The water is preferably present in an amount of from 1 to 9 volumes of liquid water per volume of nitro compound. A preferred catalyst is molybdenum sulphide deposited on charcoal, the molybdenum sulphide comprising from 10-80 per cent. and preferably 15 per cent. of the mixture. The apparatus used to carry out the invention comprises a reactor 12 into which is passed a mixture of mono-nitro-hydrocarbon and hydrogen from lines 5 and 6 respectively via heat exchanger 8 and preheater 10. The products pass down the reactor 12 through catalyst chambers 13a, 13b, 13c and 13d. In accordance with the invention the reaction temperature is controlled by admitting part of the nitro compound from the storage chamber 1 via lines 4 and 25 where it is contacted with water added through line 26, and admitted into reactor through a pluralty of points 29a, 29b and 29c, preferably in the spaces between the catalyst beds. Water withdrawn from reactor 12 along with the products of reaction is separated in the separator 20, withdrawn through line 23 and recycled to the water inlet 26.ALSO:Aromatic amines are prepared by the reduction of mononitro aromatic hydrocarbons with hydrogen in the presence of a hydrogenation catalyst, wherein the reaction temperature is controlled by introducing a mixture of the nitro hydrocarbons and liquid water into the reaction zone at a plurality of points and immediately vaporizing the water under the reaction temperature. The water is preferably present in an amount of from 1 to 9 volumes of liquid water per volume of nitro compound. A preferred catalyst is molybdenum sulphide deposited on charcoal, the molybdenum sulphide comprising from 10-8 per cent and preferably 15 per cent by weight of the mixture. In an example an apparatus is described. The specific embodyment of the invention described is the reduction of nitro xylene isomers. For this purpose xylene is nitrated and the dinitro compounds removed by distillation. The mono-nitro-xylenes are then reduced with hydrogen under a pressure of 650 to 700 lbs. in the presence of 15 per cent by weight of molybdenum sulphide deposited on charcoal, the mono-nitro-xylenes being introduced at a plurality of points in admixture with 2-2 parts by weight of water per part of mono-nitro-xylenes.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB596287A true GB596287A (en) | 1948-01-01 |
Family
ID=1626935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB167444A Expired GB596287A (en) | 1944-01-28 | Improvements in the production of aromatic amines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB596287A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003043726A1 (en) * | 2001-11-20 | 2003-05-30 | Consejo Superior De Investigaciones Cientificas | Test unit for studying catalysts in reactions involving a short contact time between the catalyst and the reagents |
| EP1484312A1 (en) * | 2003-06-04 | 2004-12-08 | Bayer MaterialScience AG | Process for preparing aromatic amines |
| WO2011113491A1 (en) * | 2010-03-18 | 2011-09-22 | Huntsman International Llc | Process for the conversion of aromatic nitro compound into amines |
-
1944
- 1944-01-28 GB GB167444A patent/GB596287A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003043726A1 (en) * | 2001-11-20 | 2003-05-30 | Consejo Superior De Investigaciones Cientificas | Test unit for studying catalysts in reactions involving a short contact time between the catalyst and the reagents |
| ES2187387A1 (en) * | 2001-11-20 | 2003-06-01 | Univ Politecnica De Valencia C | Test unit for studying catalysts in reactions involving a short contact time between the catalyst and the reagents |
| EP1484312A1 (en) * | 2003-06-04 | 2004-12-08 | Bayer MaterialScience AG | Process for preparing aromatic amines |
| US7122701B2 (en) | 2003-06-04 | 2006-10-17 | Bayer Aktiengesellschaft | Process for preparing aromatic amines |
| WO2011113491A1 (en) * | 2010-03-18 | 2011-09-22 | Huntsman International Llc | Process for the conversion of aromatic nitro compound into amines |
| CN102811996A (en) * | 2010-03-18 | 2012-12-05 | 亨茨曼国际有限公司 | Process For The Conversion Of Aromatic Nitro Compound Into Amines |
| RU2518110C1 (en) * | 2010-03-18 | 2014-06-10 | ХАНТСМЭН ИНТЕРНЭШНЛ ЭлЭлСи | Method of converting aromatic nitrocompound in amines |
| CN102811996B (en) * | 2010-03-18 | 2014-10-01 | 亨茨曼国际有限公司 | Process For The Conversion Of Aromatic Nitro Compound Into Amines |
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