CN104098477A - Device and method for production of o-chloroaniline through continuous catalytic hydrogenation reduction of o-nitro chloro benzene - Google Patents
Device and method for production of o-chloroaniline through continuous catalytic hydrogenation reduction of o-nitro chloro benzene Download PDFInfo
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Abstract
The invention discloses a device and method for production of o-chloroaniline through continuous catalytic hydrogenation reduction of o-nitro chloro benzene. The method comprises the following steps: o-nitro chloro benzene, a catalyst and a dechlorination inhibitor are put into a hydrogenation reactor, and bottom materials are distributed well; nitrogen and hydrogen are sequentially used for displacing a system completely; a feed valve is opened, the o-nitro chloro benzene and the dechlorination inhibitor are continuously fed into the hydrogenation reactor, wherein the mass ratio of the o-nitro chloro benzene to the catalyst to the dechlorination inhibitor is 1:(0.001-0.005):(0.001-0.005); hydrogen is fed into the hydrogenation reactor for hydrogenation reaction, wherein the reaction temperature is 60-100 DEG C and the pressure is 0.5-1.5 MPa; hydrogenated liquid enters a heat exchanger firstly through a circulating pump and then passes through a cross-flow filter; the catalyst and part of hydrogenated liquid as well as fresh raw materials together enter an ejector for circulation, and the other part of the hydrogenated liquid is extracted out continuously, and o-chloroaniline is obtained after treatment. The device and the method disclosed by the invention have advantages that the production cycle is short, the catalyst selectivity is high, the dechlorination rate is low, the yield is high, the quality is stable, the equipment efficiency is high and continuous production is realized.
Description
Technical field
The present invention relates to Ortho-Chloro aniline production equipment and method, be specifically related to the also device and method of original production Ortho-Chloro aniline of a kind of o-Nitrochlorobenzene continuous catalytic hydrogenation.
Background technology
Ortho-Chloro aniline is a kind of important organic chemical industry's intermediate, is widely used in urethane, agricultural chemicals, medicine and dyestuffs industries.Ortho-Chloro aniline is reduced and made by o-Nitrochlorobenzene, and traditional method of reducing has iron powder reducing method, sodium sulfide reducing method, electrolytic reduction and catalytic hydrogenating reduction method.Iron powder reducing method and sodium sulfide reducing method are heavy owing to polluting, energy consumption is high, has listed superseded process directory in China; Electrolytic reduction facility investment is large, energy consumption is too high; Catalytic hydrogenating reduction method has the advantages such as technical process is short, energy consumption is low, the three wastes are few, is a kind of process for cleanly preparing.Therefore the production method that, catalytic hydrogenating reduction Fa Shi Ortho-Chloro aniline manufacturing enterprise generally adopts.
Catalytic hydrogenating reduction is produced Ortho-Chloro aniline and is mostly adopted autoclave batch production at present, in intermittent type hydrogenating reduction process, every production one still material all will pass through pressure testing, displacement, reaction and return to initial conditions etc. again, this batch production going round and beginning again, production cycle is long, investment is large, and plant factor is low, complex operation, labour intensity is large, catalyzer is short work-ing life, and hydrogen loss is large, unstable product quality, the mixing of gas-liquid-solid three-phase simultaneously relies on to stir to be carried out, mass transfer effect is poor, and side reaction is many, and dechlorination rate is high.
Patent CN101774931A provides a kind of method that adopts fixed-bed reactor serialization to produce Ortho-Chloro aniline, the method taking ethyl acetate as solvent, nickelalloy as the organic amine such as catalyzer, Dyhard RU 100 be dechlorination inhibitor, catalytic hydrogenating reduction o-Nitrochlorobenzene, the consumption of catalyzer is the 5-20wt% of o-Nitrochlorobenzene, the consumption of dechlorination inhibitor is the 10-60wt% of catalyst levels, the selectivity of Ortho-Chloro aniline is greater than 99%, and dechlorination rate is less than 0.3%, and product yield is at 90-93.5%.The method catalyst selectivity is poor, and dechlorination rate is high, and product yield is poor, and the consumption of catalyzer and dechlorination inhibitor is large, need to reclaim dechlorination inhibitor and solvent, and the regeneration of catalyzer and replacing are inconvenient in addition.
Summary of the invention
The object of the invention is to: the also device and method of original production Ortho-Chloro aniline of a kind of o-Nitrochlorobenzene continuous catalytic hydrogenation is provided, that the device and method that Ortho-Chloro aniline is produced in this serialization has is with short production cycle, catalyst selectivity is high, dechlorination rate is low, product yield is high, constant product quality, technical process are simple, plant efficiency high, the production efficiency that effectively improves o-Nitrochlorobenzene hydrogenating reduction and produce Ortho-Chloro aniline.
Technical solution of the present invention is: the production equipment of this Ortho-Chloro aniline comprises hydrogenator, recycle pump, interchanger, cross-flow filter and injector, injector is installed at hydrogenator top, hydrogenator bottom is connected with the import of recycle pump by pipeline, circulation pump outlet is connected with the import of interchanger by pipeline, the outlet of interchanger is connected with the import of cross-flow filter by pipeline, the outlet of cross-flow filter is connected with the import of injector by pipeline, and entirety forms the device of continuous catalytic hydrogenation reduction reaction production Ortho-Chloro aniline.
Wherein, hydrogenator is provided with chuck, material is heated up for the hydrogenation starting stage.
The production method of this Ortho-Chloro aniline comprises the following steps: o-Nitrochlorobenzene, noble metal catalyst, dechlorination inhibitor are dropped into the good bed material of cloth in hydrogenator, and by clean intrasystem air displacement, then with hydrogen, nitrogen replacement is clean with nitrogen; Then open feed valve, o-Nitrochlorobenzene and dechlorination inhibitor are sent into hydrogenator continuously, wherein the mass ratio of o-Nitrochlorobenzene, noble metal catalyst, dechlorination inhibitor is 1:0.001-0.005:0.001-0.005, pass into hydrogen, carry out hydrogenation reduction, hydrogenation reaction temperature is that 60-100 DEG C, pressure are 0.5-1.5MPa; In hydrogenator, first the hydride of mixed catalyst enters interchanger by recycle pump and removes reaction heat maintenance system temperature of reaction, pass through again cross-flow filter, catalyzer enters injector with partial hydrogenation liquid and fresh o-Nitrochlorobenzene and goes circulation together with dechlorination inhibitor, another part hydride reaction solution from cross-flow filter exports continuous extraction, enter water-and-oil separator and remove moisture, send into again rectifying separation operation, obtain Ortho-Chloro aniline product.
Wherein, described catalyzer is platinum carbon (Pt/C) catalyzer, and the mass percent of platinum is 1-5%.
Wherein, described dechlorination inhibitor is organic amine compound, is the one in diethylamine, triethylamine, Monoethanolamine MEA BASF, diethanolamine, trolamine, aniline, Dyhard RU 100, pyridine and pyridines low molecular compound, piperidines and piperidines.
The present invention, compared with existing Ortho-Chloro aniline production equipment and method, has following advantage:
1, the use of hydrogenation reaction unit injection device and recycle pump, not only make reaction system obtain high mass transfer effect, improved speed of reaction, also make whole reaction system realize circulation fast, ensured that the temperature in reaction system is impartial everywhere, reaction can steadily and fast be carried out; Simultaneously splendid mass transfer effect, makes that speed of response is fast, the reaction times is short, has greatly improved throughput; Good heat-transfer effect, makes hydrogenation reaction even, reduces the generation of side reaction, has improved quality product and yield.
2, equipment volume is little, and technical process is simple, and the Ortho-Chloro aniline production equipment of a set of 10,000 t/a only needs two 2.5m
3the reactor of left and right, is 1/20th of tank reactor volume, and facility investment is saved greatly, 10 times of left and right that the still reaction technological equipment investment of same throughput is technique of the present invention.
3, precious metal (Pt/C) catalyst utilization is high, and consumption is few, is only the 0.1-0.5% of o-Nitrochlorobenzene quality, thereby has saved running cost and investment.
4, the consumption of dechlorination inhibitor is the 0.1-0.5% of o-Nitrochlorobenzene quality, and the consumption of dechlorination inhibitor is very little, does not need to reclaim.
5, hydrogenation reaction adopts external heat exchanger, makes heat interchanging area not be subject to the restriction of reactor capacity and reaction mass, according to the size of need of production configuration heat exchanger area.
Brief description of the drawings
Fig. 1 is the also process flow sheet of original production Ortho-Chloro aniline of o-Nitrochlorobenzene continuous catalytic hydrogenation.
In figure: 1 hydrogenator, 2 recycle pumps, 3 interchanger, 4 cross-flow filters, 5 injectors.
Embodiment
Further illustrate technical solution of the present invention below in conjunction with embodiment, these embodiment can not be interpreted as it is the restriction to technical scheme.
As shown in Figure 1, the production equipment of this Ortho-Chloro aniline is made up of hydrogenator 1, recycle pump 2, interchanger 3, cross-flow filter 4 and injector 5, injector 5 is installed at hydrogenator 1 top, hydrogenator 1 bottom is connected with the import of recycle pump 2 by pipeline, the outlet of recycle pump 2 is connected with the import of interchanger 3 by pipeline, the outlet of interchanger 3 is connected with the import of cross-flow filter 4 by pipeline, the outlet of cross-flow filter 4 is connected with the import of injector 5 by pipeline, and entirety forms the device of continuous catalytic hydrogenation reduction reaction production Ortho-Chloro aniline.
Wherein, hydrogenator 1 is provided with chuck, material is heated up for the hydrogenation starting stage.
Embodiment 1: platinum carbon (Pt/C) catalyzer that is 1% by o-Nitrochlorobenzene, platinum mass percent, diethylamine dechlorination inhibitor drop into the good bed material of cloth in hydrogenator is by clean intrasystem air displacement, cleaner by nitrogen replacement with hydrogen with nitrogen; Then open feed valve, o-Nitrochlorobenzene and dechlorination inhibitor are sent into hydrogenator continuously, wherein the mass ratio of o-Nitrochlorobenzene, noble metal catalyst, dechlorination inhibitor is 1:0.001:0.001, pass into hydrogen, carry out hydrogenation reduction, hydrogenation reaction temperature is that 60 DEG C, pressure are 0.5MPa; In hydrogenator, first the hydride of mixed catalyst enters interchanger by recycle pump and removes reaction heat maintenance system temperature of reaction, pass through again cross-flow filter, catalyzer enters injector with partial hydrogenation liquid and fresh o-Nitrochlorobenzene and goes circulation together with dechlorination inhibitor, another part hydride reaction solution from cross-flow filter exports continuous extraction, enter water-and-oil separator and remove moisture, send into again rectifying separation operation, obtain Ortho-Chloro aniline product.Transformation efficiency is 100%, selectivity 99.7%, and dechlorination rate is less than 0.07%, product content 99.7%, yield 99.5%.
Embodiment 2: platinum carbon (Pt/C) catalyzer that is 3% by o-Nitrochlorobenzene, platinum mass percent, trolamine dechlorination inhibitor drop into the good bed material of cloth in hydrogenator is by clean intrasystem air displacement, cleaner by nitrogen replacement with hydrogen with nitrogen; Then open feed valve, o-Nitrochlorobenzene and dechlorination inhibitor are sent into hydrogenator continuously, wherein the mass ratio of o-Nitrochlorobenzene, noble metal catalyst, dechlorination inhibitor is 1:0.003:0.003, pass into hydrogen, carry out hydrogenation reduction, hydrogenation reaction temperature is that 80 DEG C, pressure are 1.0MPa; In hydrogenator, first the hydride of mixed catalyst enters interchanger by recycle pump and removes reaction heat maintenance system temperature of reaction, pass through again cross-flow filter, catalyzer enters injector with partial hydrogenation liquid and fresh o-Nitrochlorobenzene and goes circulation together with dechlorination inhibitor, another part hydride reaction solution from cross-flow filter exports continuous extraction, enter water-and-oil separator and remove moisture, send into again rectifying separation operation, obtain Ortho-Chloro aniline product.Transformation efficiency is 100%, selectivity 99.6%, and dechlorination rate is less than 0.05%, product content 99.7%, yield 99.4%.
Embodiment 3: platinum carbon (Pt/C) catalyzer that is 5% by o-Nitrochlorobenzene, platinum mass percent, pyridine dechlorination inhibitor drop into the good bed material of cloth in hydrogenator is by clean intrasystem air displacement, cleaner by nitrogen replacement with hydrogen with nitrogen; Then open feed valve, o-Nitrochlorobenzene and dechlorination inhibitor are sent into hydrogenator continuously, wherein the mass ratio of o-Nitrochlorobenzene, noble metal catalyst, dechlorination inhibitor is 1:0.005:0.005, pass into hydrogen, carry out hydrogenation reduction, hydrogenation reaction temperature is that 100 DEG C, pressure are 1.5MPa; In hydrogenator, first the hydride of mixed catalyst enters interchanger by recycle pump and removes reaction heat maintenance system temperature of reaction, pass through again cross-flow filter, catalyzer enters injector with partial hydrogenation liquid and fresh o-Nitrochlorobenzene and goes circulation together with dechlorination inhibitor, another part hydride reaction solution from cross-flow filter exports continuous extraction, enter water-and-oil separator and remove moisture, send into again rectifying separation operation, obtain Ortho-Chloro aniline product.Transformation efficiency is 100%, selectivity 99.7%, and dechlorination rate is less than 0.05%, product content 99.8%, yield 99.5%.
Claims (5)
1. the also device of original production Ortho-Chloro aniline of o-Nitrochlorobenzene continuous catalytic hydrogenation, it is characterized in that: the production equipment of this Ortho-Chloro aniline is by hydrogenator (1), recycle pump (2), interchanger (3), cross-flow filter (4) and injector (5) composition, injector (5) is installed at hydrogenator (1) top, hydrogenator (1) bottom is connected with the import of recycle pump (2) by pipeline, the outlet of recycle pump (2) is connected with the import of interchanger (3) by pipeline, the outlet of interchanger (3) is connected with the import of cross-flow filter (4) by pipeline, the outlet of cross-flow filter (4) is connected with the import of injector (5) by pipeline, entirety forms the device of continuous catalytic hydrogenation reduction reaction production Ortho-Chloro aniline.
2. the also device of original production Ortho-Chloro aniline of o-Nitrochlorobenzene continuous catalytic hydrogenation according to claim 1, is characterized in that: hydrogenator (1) is provided with chuck.
3. the also method of original production Ortho-Chloro aniline of o-Nitrochlorobenzene continuous catalytic hydrogenation, the production method that it is characterized in that this Ortho-Chloro aniline comprises the following steps: o-Nitrochlorobenzene, noble metal catalyst, dechlorination inhibitor are dropped into the good bed material of cloth in hydrogenator, by clean intrasystem air displacement, then with hydrogen, nitrogen replacement is clean with nitrogen; Then open feed valve, o-Nitrochlorobenzene and dechlorination inhibitor are sent into hydrogenator continuously, wherein the mass ratio of o-Nitrochlorobenzene, noble metal catalyst, dechlorination inhibitor is 1:0.001-0.005:0.001-0.005, pass into hydrogen, carry out hydrogenation reduction, hydrogenation reaction temperature is that 60-100 DEG C, pressure are 0.5-1.5MPa; In hydrogenator, first the hydride of mixed catalyst enters interchanger by recycle pump and removes reaction heat maintenance system temperature of reaction, pass through again cross-flow filter, catalyzer enters injector with partial hydrogenation liquid and fresh o-Nitrochlorobenzene and goes circulation together with dechlorination inhibitor, another part hydride reaction solution from cross-flow filter exports continuous extraction, enter water-and-oil separator and remove moisture, send into again rectifying separation operation, obtain Ortho-Chloro aniline product.
4. the also method of original production Ortho-Chloro aniline of o-Nitrochlorobenzene continuous catalytic hydrogenation according to claim 3, is characterized in that: described catalyzer is platinum carbon (Pt/C) catalyzer, and the mass percent of platinum is 1-5%.
5. the also method of original production Ortho-Chloro aniline of o-Nitrochlorobenzene continuous catalytic hydrogenation according to claim 3, it is characterized in that: described dechlorination inhibitor is organic amine compound, is the one in diethylamine, triethylamine, Monoethanolamine MEA BASF, diethanolamine, trolamine, aniline, Dyhard RU 100, pyridine and pyridines low molecular compound, piperidines and piperidines.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935916A (en) * | 2017-10-27 | 2018-04-20 | 江苏仁欣化工股份有限公司 | The method that catalytic hydrogenation produces permanent violet intermediate |
| CN114349644A (en) * | 2020-10-13 | 2022-04-15 | 中石化南京化工研究院有限公司 | Method for preparing dichloroaniline from byproduct mixed dichlorobenzene |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101333169A (en) * | 2007-03-01 | 2008-12-31 | 淮安嘉诚高新化工股份有限公司 | Production method of o-chloroaniline |
| CN103936559A (en) * | 2014-04-15 | 2014-07-23 | 淮安嘉诚高新化工股份有限公司 | Method for continuously producing resorcin |
-
2014
- 2014-07-28 CN CN201410361829.4A patent/CN104098477A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101333169A (en) * | 2007-03-01 | 2008-12-31 | 淮安嘉诚高新化工股份有限公司 | Production method of o-chloroaniline |
| CN103936559A (en) * | 2014-04-15 | 2014-07-23 | 淮安嘉诚高新化工股份有限公司 | Method for continuously producing resorcin |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935916A (en) * | 2017-10-27 | 2018-04-20 | 江苏仁欣化工股份有限公司 | The method that catalytic hydrogenation produces permanent violet intermediate |
| CN114349644A (en) * | 2020-10-13 | 2022-04-15 | 中石化南京化工研究院有限公司 | Method for preparing dichloroaniline from byproduct mixed dichlorobenzene |
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Application publication date: 20141015 |