CN1594279A - Process and apparatus for producing o-phenylenediamine - Google Patents
Process and apparatus for producing o-phenylenediamine Download PDFInfo
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- CN1594279A CN1594279A CN 200410025783 CN200410025783A CN1594279A CN 1594279 A CN1594279 A CN 1594279A CN 200410025783 CN200410025783 CN 200410025783 CN 200410025783 A CN200410025783 A CN 200410025783A CN 1594279 A CN1594279 A CN 1594279A
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- phenylene diamine
- orthodichlorobenzene
- coil pipe
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000008569 process Effects 0.000 title abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 93
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims abstract description 50
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 46
- 238000005915 ammonolysis reaction Methods 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052802 copper Inorganic materials 0.000 claims abstract description 14
- 239000010949 copper Substances 0.000 claims abstract description 14
- 239000000376 reactant Substances 0.000 claims abstract description 8
- 238000012360 testing method Methods 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 10
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 10
- 229940045803 cuprous chloride Drugs 0.000 claims description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000009413 insulation Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 claims 1
- 230000010363 phase shift Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 230000006872 improvement Effects 0.000 description 8
- 239000002994 raw material Substances 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000002932 luster Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000035800 maturation Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- 150000004818 1,2-dichlorobenzenes Chemical class 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
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 241000721047 Danaus plexippus Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001546 nitrifying effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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Abstract
The invention provides a process for producing o-phenylendiamine comprising the steps of, charging ortho dichlorobenzene, ammonia into high temperature, high pressure container, proceeding ammonolysis reaction at the presence of catalyst, analyzing and separating the obtained reactant, charging ortho dichlorobenzene, liquid ammonia, copper catalyst, phase shift catalyst into pipe type reactor continuously for ammonolysis reaction. The invention also discloses a production apparatus for realizing the method.
Description
Technical field:
The present invention relates to a kind of synthetic method and device of fragrant organic amine, the high-pressure channelization synthetic method and the device of particularly a kind of chemical intermediate---O-Phenylene Diamine.
Background technology:
O-Phenylene Diamine is a kind of important organic chemical industry's intermediate, except being used for DYE PRODUCTION, or the main raw material of systemic fungicide such as pesticide carbendazim, benzene monarch spirit, (methyl) thiophanate.The route that many synthetic orthodichlorobenzenes are arranged at present, wherein three outbalance routes are as follows:
One, document Rev.Chim., 1976,27 (5): 394～401, be starting raw material with the o-Nitrochlorobenzene, obtain the O-Phenylene Diamine product through ammonification, reduction, reaction formula is as follows:
This operational path maturation, the total recoverys in two steps are about 64%, and wherein the aminating reaction of the first step is according to the document pesticide industry, and 1976, in 7:18～20 report is arranged, obtained the better result of canalization production technique.But the toxicity of this reaction raw materials and intermediate is higher, and step working condition influences worker health, and the raw material o-Nitrochlorobenzene is under-supply sometimes in addition, enlarges to produce to be restricted.
Two, the synthetic route of american documentation literature USP4207261 report, be to be starting raw material with the santochlor, under proper temperature, carry out nitratedly obtaining 2, the 5-dichloronitrobenzene, dichloronitrobenzene (I) with gained carries out ammonolysis reaction with strong aqua again, then obtains 4-chloro-2-N-methyl-p-nitroaniline (II) after treatment.And then will go up step gained intermediate (II) and carry out shortening and dechlorination reaction, promptly get the finished product O-Phenylene Diamine after the processing.Reaction formula is as follows
The santochlor nitration reaction is no coupling product almost, and three step building-up reactions yields are all higher, but nitrifying process need be used nitration mixture, to the equipment requirements height, pollutes greatly, uses aborning at present.
Three, patent Britain GB440697 and Japanese JP57027133 are catalyzer with copper in autoclave, and orthodichlorobenzene carries out ammonolysis reaction, the O-Phenylene Diamine of higher yields.Reaction formula is as follows
This method has two important practical problemss not solve, and the one, the ins and outs of the sepn process of O-Phenylene Diamine are not open, and the 2nd, the recovery problem of catalyzer.Japan Cao Da industrial is studied this, but the details of research contents is not announced yet.Still formula ammonia is separated maturation of technology, but the defective that exists is: the first, and intermittent reaction, the operating time is long, and equipment capacity is less; The second, the still formula ammonolysis reaction time is long, High Temperature High Pressure, and side product sodium chloride is very serious to the corrosion of equipment, and facility investment increases, and has potential safety hazard; The 3rd, long-time pyroreaction exerts an adverse impact to the color and luster of product, dyestuff intermediate particularly, and the color and luster influence is more serious.
Summary of the invention:
At the technical problem that exists in the prior art, the invention provides and a kind ofly realize serialization production, cost is low, yield is high, good, the eco-friendly O-Phenylene Diamine synthetic method of security and employed device.
The present invention is for reaching above purpose, be to realize: a kind of method of producing O-Phenylene Diamine is provided by such technical scheme, comprise and earlier orthodichlorobenzene, ammonia are put into high temperature, high pressure vessel, carry out ammonolysis reaction under the effect of catalyzer, the gained reactant is analyzed again and separated, this orthodichlorobenzene, liquefied ammonia, copper catalyst, phase-transfer catalyst enter continuously and carry out ammonolysis reaction in the pipeline reactor.
The weight ratio of liquefied ammonia and orthodichlorobenzene is 0.8～1.27: 1, and the weight of described copper catalyst is 0.25%～0.5% of orthodichlorobenzene, and the weight ratio of described copper catalyst and phase-transfer catalyst is 1: 1; Temperature of reaction is 150～200 ℃ in the described ammonolysis reaction, and reaction pressure is 15～18Mpa, and the residence time of reactant in pipeline reactor is 20～60 minutes.
As a kind of improvement of method of the present invention: orthodichlorobenzene, liquefied ammonia, copper catalyst, phase-transfer catalyst earlier in premixer, through after high pressure, the stirring at normal temperature, enter pipeline reactor again; Pressure in the premixer equals the pressure of ammonolysis reaction.
As another improvement of method of the present invention: copper catalyst, phase-transfer catalyst dissolve in weak ammonia or the water in advance, enter premixer again, and the concentration of this weak ammonia is≤30%.
As another improvement of method of the present invention: copper catalyst is a cuprous chloride, and phase-transfer catalyst is the quaternary ammonium salt catalyzer.
A kind of device of realizing producing the O-Phenylene Diamine method, comprise test tank 1 that orthodichlorobenzene is provided, mainly provide catalyzer test tank 2, provide liquefied ammonia test tank 3, in establish the pipeline reactor 17 of coil pipe 18, well heater 16 links to each other with pipeline reactor 17; The exit end of test tank 1 is provided with high-pressure metering pump 4, and high-pressure metering pump 4 connects the entrance end of coil pipe 18 by pipeline 7; The exit end of test tank 2 is provided with high-pressure metering pump 5, and high-pressure metering pump 5 connects the entrance end of coil pipe 18 by pipeline 8; The exit end of test tank 3 is provided with high-pressure metering pump 6, and high-pressure metering pump 6 connects the entrance end of coil pipe 18 by pipeline 9; The exit end of coil pipe 18 connects insulation expander 22 by pipe 20, and pipe 20 is provided with reducing valve 19; Insulation expander 22 is provided with outlet 21 and outlet 23.
A kind of improvement as device of the present invention: the exit end of pipeline 7,8,9 all connects the entrance end of premixer 13, and the exit end of this premixer 13 is by the entrance end of pipeline 15 connection coil pipes 18, and premixer 13 links to each other with force (forcing) pump 24.
Another improvement as device of the present invention: the internal diameter of coil pipe 18 is 3mm.
Another improvement as device of the present invention: pipeline 7 is provided with stopping valve 10, and pipeline 8 is provided with stopping valve 11, and pipeline 9 is provided with stopping valve 12, and pipeline 15 is provided with stopping valve 14.
Among the present invention, the density of the density ≈ water of weak ammonia, orthodichlorobenzene: liquefied ammonia: water (density ratio)=1.3059: 0.6386: 1.
The present invention adopts the device of canalization to produce O-Phenylene Diamine, and with the blank pipe alternative reaction still of suitable diameter, the bearing pressure ability is strong, and security is good, easy control of reaction conditions, and all right suitable reduction temperature of reaction makes that the color and luster of product is good.Present method adopts catalyzer is dissolved in weak ammonia or the water in advance, can make catalyzer enter reacting pipe (this moment, weak ammonia only played the effect of catalyst-solvent, and itself does not participate in ammonolysis reaction) continuously equably with weak ammonia or water metering; The forced-flow of material in reaction tubes substitutes in the still and stirs, and energy simplified apparatus technology is saved investment; Can realize serialization production, the productive rate height, constant product quality, industrial a small amount of investment of needs just can realize scale operation.Ammonia unnecessary in the ammonolysis reaction can reclaim, and can not cause the pollution to environment.
Embodiment:
Be elaborated below in conjunction with 1 pair of embodiment of accompanying drawing:
Embodiment 1: a kind of reaction unit, comprise test tank 1 that orthodichlorobenzene is provided, mainly provide catalyzer test tank 2, provide liquefied ammonia test tank 3, in establish pipeline reactor 17, the premixer 13 of coil pipe 18, well heater 16 links to each other with pipeline reactor 17, and this well heater 16 can be selected oil bath heater; Premixer 13 links to each other with force (forcing) pump 24, and it is required pressure that force (forcing) pump 24 can keep the pressure in the premixer 13.For the ease of observation jar interior raw material, test tank 1 and test tank 2 are designed to the test tank that glass is made; The test tank 3 usefulness stainless steels that hold liquefied ammonia are made, and the surface of test tank 3 is provided with gage glass.The exit end of test tank 1 is provided with high-pressure metering pump 4, and high-pressure metering pump 4 connects the entrance end of premixer 13 by pipeline 7; Equally, the exit end of test tank 2 is provided with high-pressure metering pump 5, and high-pressure metering pump 5 connects the entrance end of premixer 13 by pipeline 8; Equally, the exit end of test tank 3 is provided with high-pressure metering pump 6, and high-pressure metering pump 6 connects the entrance end of premixer 13 by pipeline 9.The exit end of premixer 13 passes through the entrance end that pipeline 15 connects coil pipes 18, and the exit end of coil pipe 18 is incubated expanders 22 by pipe 20 connections, is provided with reducing valve 19 on pipe 20; By opening reducing valve 19, make to enter insulation expander 22 after the reactant decompression.Insulation expander 22 is provided with outlet 21 and outlet 23, and outlet 21 is used for collecting the unnecessary ammonia in reaction back, and outlet 23 is used for collecting the reaction products therefrom.Coil pipe 18 is 6mm for external diameter, and internal diameter is the high pressure resistant pipe of 3mm, and the length of this coil pipe 18 is about 50m.(the length computation formula of coil pipe 18 is: the flow velocity * residence time of reactant in pipeline reactor.) on pipeline 7, being provided with stopping valve 10, described pipeline 8 is provided with stopping valve 11, and described pipeline 9 is provided with stopping valve 12, is provided with stopping valve 14 on pipeline 15; These 4 stopping valve are in normally open at work, and the purpose that adds these stopping valve is to be convenient to dismounting in order keeping in repair, to clean.
Reaction method is as follows: add orthodichlorobenzene in the test tank 1, adding concentration is 25% weak ammonia in the test tank 2, contains 1% cuprous chloride and 1% Tetrabutyl amonium bromide in this weak ammonia, adds liquefied ammonia in the test tank 3.Open high-pressure metering pump 4,5,6 simultaneously, the top hole pressure of high-pressure metering pump 4,5,6 all is set to 18Mpa.Control the interior material of three test tanks with throughput ratio (test tank 1: test tank 2: test tank 3) be 3: 1: 5, the pipeline 7,8,9 that passes through equably separately injects premixers 13, carry out stirring at normal temperature in premixer 13, the pressure of premixer 13 remains on 18Mpa.(at this moment, the weight ratio of actual cuprous chloride and liquefied ammonia is 0.255%: 1; The weight ratio of liquefied ammonia and orthodichlorobenzene is 0.815: 1.) then, the mixture that comes out from premixer 13 enters coil pipe 18 by managing 15, keeps about 0.15ml/ mass flow of second in coil pipe 18, mixture from advance coil pipe 18, to the time that goes out coil pipe 18, promptly ammonolysis reaction residence Time Calculation value is 39.25 minutes.Ammonolysis reaction temperature in the coil pipe 18 is 200 ℃, and pressure is 18Mpa.By opening reducing valve 19, make reactant decompression back enter insulation expander 22 by managing 20, collect unnecessary ammonia from exporting 21; From exporting 23 collecting reaction products, and cooling becomes solidliquid mixture.
To react the gained solid analyzes and separates: simple distillation; still-process adds 1% Sodium sulfhydrate protection, just can collect under the 2.5cmHg overhead product between 196～200 ℃ of the temperature; just can obtain fusing point behind the hot water recrystallization and be 102～103 ℃ O-Phenylene Diamine product, yield 63%.
Embodiment 2: reaction unit is with embodiment 1.Adding concentration is 15% weak ammonia in the test tank 2, contains 0.979% cuprous chloride and 0.979% Tetrabutyl amonium bromide in this weak ammonia.Regulate orthodichlorobenzene: weak ammonia: the throughput ratio of liquefied ammonia=enter pipeline at 1.5: 1: 3.3, the top hole pressure of high-pressure metering pump 4,5,6 all is set to 15Mpa.(this moment, the weight ratio of actual cuprous chloride and liquefied ammonia was 0.5%: 1; The weight ratio of liquefied ammonia and orthodichlorobenzene is 1.076: 1.) 150 ℃ of ammonolysis reaction temperature in the control coil pipe 18, pressure 15Mpa keeps the about 0.3ml/ mass flow of second, ammonolysis reaction residence Time Calculation value is 19.625 minutes, all the other production methods obtain the O-Phenylene Diamine product of similar performance with embodiment 1, yield about 56%.
Embodiment 3: reaction unit is with embodiment 1.Adding concentration is 5% weak ammonia in the test tank 2, contains 1% cuprous chloride and 1% Tetrabutyl amonium bromide in this weak ammonia.Regulate the throughput ratio orthodichlorobenzene: weak ammonia: liquefied ammonia=enter pipeline at 2: 1: 5, the top hole pressure of high-pressure metering pump 4,5,6 all is set to 16Mpa.(this moment, the weight ratio of actual cuprous chloride and liquefied ammonia was 0.38%: 1, and the weight ratio of liquefied ammonia and orthodichlorobenzene is 1.223: 1.) 175 ℃ of control reaction temperature, pressure 16Mpa keeps the about 0.1ml/ mass flow of second, and ammonolysis reaction residence Time Calculation value is 58.88 minutes, and all the other production methods are with embodiment 1.Obtain the O-Phenylene Diamine product of similar performance, yield 68%.
Embodiment 4: reaction unit is with embodiment 1.Add entry in the test tank 2, contain 0.8% cuprous chloride and 0.8% Tetrabutyl amonium bromide in the water.Regulate the throughput ratio orthodichlorobenzene: water: liquefied ammonia=enter pipeline at 2: 1: 3.3, the top hole pressure of high-pressure metering pump 4,5,6 all is set to 17Mpa.(this moment, the weight ratio of actual cuprous chloride and liquefied ammonia was 0.31%: 1, and the weight ratio of liquefied ammonia and orthodichlorobenzene is 0.807: 1.) 175 ℃ of control reaction temperature, pressure 17Mpa keeps the about 0.1ml/ mass flow of second, and ammonolysis reaction residence Time Calculation value is 58.88 minutes, and all the other production methods are with embodiment 1.Obtain the O-Phenylene Diamine product of similar performance, yield 65%.
The above only is several embodiments of the present invention; should be pointed out that for the person of ordinary skill of the art, can also make many modification and improvement; for example change the concentration of dilute ammonia solution, all modification or improvement all should be considered as protection scope of the present invention.
Claims (9)
1, a kind of method of producing O-Phenylene Diamine, comprise and earlier orthodichlorobenzene, ammonia are put into high temperature, high pressure vessel, carry out ammonolysis reaction under the effect of catalyzer, the gained reactant is analyzed again and separated, it is characterized in that: described orthodichlorobenzene, liquefied ammonia, copper catalyst, phase-transfer catalyst enter continuously and carry out ammonolysis reaction in the pipeline reactor.
2, the method for production O-Phenylene Diamine according to claim 1, it is characterized in that: the weight ratio of described liquefied ammonia and orthodichlorobenzene is 0.8～1.27: 1, the weight of described copper catalyst is 0.25%～0.5% of orthodichlorobenzene, and the weight ratio of described copper catalyst and phase-transfer catalyst is 1: 1; Temperature of reaction is 150～200 ℃ in the described ammonolysis reaction, and reaction pressure is 15～18Mpa, and the residence time of reactant in pipeline reactor is 20～60 minutes.
3, the method for production O-Phenylene Diamine according to claim 1 and 2 is characterized in that: described orthodichlorobenzene, liquefied ammonia, copper catalyst, phase-transfer catalyst elder generation enter pipeline reactor again in premixer, through after high pressure, the stirring at normal temperature; Pressure in the described premixer equals the pressure of ammonolysis reaction.
4, the method for production O-Phenylene Diamine according to claim 3 is characterized in that: described copper catalyst, phase-transfer catalyst dissolve in weak ammonia or the water in advance, enter premixer again, and the concentration of described weak ammonia is≤30%.
5, the method for production O-Phenylene Diamine according to claim 4 is characterized in that: described copper catalyst is a cuprous chloride, and phase-transfer catalyst is the quaternary ammonium salt catalyzer.
6, a kind of device of producing O-Phenylene Diamine, it is characterized in that: comprise test tank (1) that orthodichlorobenzene is provided, mainly provide catalyzer test tank (2), provide liquefied ammonia test tank (3), in establish the pipeline reactor (17) of coil pipe (18), well heater (16) links to each other with described pipeline reactor (17); The exit end of described test tank (1) is provided with high-pressure metering pump (4), and high-pressure metering pump (4) connects the entrance end of coil pipe (18) by pipeline (7); The exit end of described test tank (2) is provided with high-pressure metering pump (5), and high-pressure metering pump (5) connects the entrance end of coil pipe (18) by pipeline (8); The exit end of described test tank (3) is provided with high-pressure metering pump (6), and high-pressure metering pump (6) connects the entrance end of coil pipe (18) by pipeline (9); The exit end of coil pipe (18) connects insulation expander (22) by pipe (20), and described pipe (20) is provided with reducing valve (19); Described insulation expander (22) is provided with outlet (21) and outlet (23).
7, the device of production O-Phenylene Diamine according to claim 6, it is characterized in that: the exit end of described pipeline (7), (8), (9) all connects the entrance end of premixer (13), the exit end of described premixer (13) is by the entrance end of pipeline (15) connection coil pipe (18), and described premixer (13) links to each other with force (forcing) pump (24).
8, according to the device of claim 6 or 7 described production O-Phenylene Diamines, it is characterized in that: described coil pipe (18) internal diameter is 3mm.
9, the device of production O-Phenylene Diamine according to claim 8, it is characterized in that: described pipeline (7) is provided with stopping valve (10), described pipeline (8) is provided with stopping valve (11), and described pipeline (9) is provided with stopping valve (12), and described pipeline (15) is provided with stopping valve (14).
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| CN102276479A (en) * | 2011-06-28 | 2011-12-14 | 江苏科圣化工机械有限公司 | Method and device for producing p-phenylenediamine by using liquid phase continuous hydrogenation method |
| CN102491905A (en) * | 2011-11-18 | 2012-06-13 | 江苏科圣化工装备工程有限公司 | Method and device for co-production of o-phenylenediamine and p-phenylenediamine |
| CN102695696A (en) * | 2009-12-29 | 2012-09-26 | 可隆工业株式会社 | Aromatic diamine and method for manufacturing the same, and aramid fiber and method for manufacturing the same |
| CN102924294A (en) * | 2012-10-22 | 2013-02-13 | 江苏康恒化工有限公司 | Method for preparing o-phenylenediamine from o-chloroaniline |
| CN101462966B (en) * | 2008-12-31 | 2013-03-20 | 安徽巨元化工有限公司 | Purification method for exquisite o-phenylenediamine |
| CN103145563A (en) * | 2013-03-29 | 2013-06-12 | 中北大学 | Method for co-producing p-phenylenediamine and o-phenylenediamine |
| CN103435495A (en) * | 2013-05-08 | 2013-12-11 | 如皋市金陵化工有限公司 | Purification process for o-phenylenediamine |
| CN105085277A (en) * | 2014-05-22 | 2015-11-25 | 江苏扬农化工集团有限公司 | Method for preparing 2,3-/2,6-dichloroaniline |
| CN106008240A (en) * | 2016-05-20 | 2016-10-12 | 浙江鸿盛化工有限公司 | Preparation method of benzophenone acid derivate and used production device |
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2004
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| CN103435495A (en) * | 2013-05-08 | 2013-12-11 | 如皋市金陵化工有限公司 | Purification process for o-phenylenediamine |
| CN103435495B (en) * | 2013-05-08 | 2016-03-09 | 如皋市金陵化工有限公司 | The purifying technique of O-Phenylene Diamine |
| CN105085277A (en) * | 2014-05-22 | 2015-11-25 | 江苏扬农化工集团有限公司 | Method for preparing 2,3-/2,6-dichloroaniline |
| CN106008240A (en) * | 2016-05-20 | 2016-10-12 | 浙江鸿盛化工有限公司 | Preparation method of benzophenone acid derivate and used production device |
| CN111039798A (en) * | 2019-12-23 | 2020-04-21 | 浙江闰土研究院有限公司 | Environment-friendly preparation method of 2-chloro-4-nitro-6-bromo-aniline |
| CN112371072A (en) * | 2020-11-05 | 2021-02-19 | 浙江迪邦化工有限公司 | System and process for continuously producing diazonium salt solution |
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