CN103086895A - Method for preparing aromatic amine from mixed nitrochlorobenzene - Google Patents
Method for preparing aromatic amine from mixed nitrochlorobenzene Download PDFInfo
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- CN103086895A CN103086895A CN2011103383717A CN201110338371A CN103086895A CN 103086895 A CN103086895 A CN 103086895A CN 2011103383717 A CN2011103383717 A CN 2011103383717A CN 201110338371 A CN201110338371 A CN 201110338371A CN 103086895 A CN103086895 A CN 103086895A
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Abstract
The invention provides a method for preparing aromatic amine by using mixed nitrochlorobenzene as a raw material. The method comprises the steps that: mixed nitrochlorobenzene is subjected to ammonolysis, deamination stripping, cooling crystallization, and centrifugal separation, such that a material comprising mixed nitroanilide is obtained; the material can be subjected to catalytic hydrogenation in an alcohol solvent, and p-phenylenediamine and o-phenylenediamine products can be prepared through separation; or before catalytic hydrogenation, part of p-nitroanilide is separated; and hydrogenation is carried out, such that p-phenylenediamine and o-phenylenediamine products can be prepared. According to the aromatic amine preparation method, the mixed nitrochlorobenzene raw material can be used in phenylenediamine production without separation, such that a product material separation process of a traditional production process is simplified, and energy consumption during production process is reduced. The method is economical and highly efficient, and the product has high purity.
Description
(1) technical field
The present invention relates to a kind of method that is prepared aromatic amine by the mixing nitro-chlorobenzene.
(2) background technology
chlorobenzene is important dyestuff, pesticide intermediate, set out by it, pass through again a series of organic synthesis unit processes, can make again various baroque intermediates, pass through the nitration mixture adiabatic nitration as chlorobenzene, can obtain the p-Nitrophenyl chloride of massfraction 60～65%, the m-nitrochlorobenzene of 34～39% o-Nitrochlorobenzene and trace, industrial way is to be used further to follow-up synthetic or processing after above-mentioned isomers is separated at present, but the nitro-chlorobenzene system is adjacent, right, between the position three kinds of isomer boiling point difference very little, nitro-chlorobenzene is heat-sensitive substance, belong to difficult separation mixture in the rectifying field, for traditional Crystallization Separation, owing to can forming the low body that melts altogether between the nitro-chlorobenzene isomer, simple crystallization can't realize separating fully, and material loss is larger.Most producer all adopts the method for rectifying and crystallization phases combination, and still there is the problem that technical requirements is high and separating energy consumption is larger in the separation of Chlorobenzene Nitration gained nitro-chlorobenzene system isomer.
In the technology of existing disclosed preparation to (neighbour) N-methyl-p-nitroaniline; still after to separate to (neighbour) nitro-chlorobenzene as raw material; prepare through the ammonia solution respectively; the raw material pre-treatment is required to improve; there is separation difficulty, prepares the defective that link is many, energy consumption is high; thereby cause production cost to improve, the problem that the environment protection difficulty strengthens.
(3) summary of the invention
The objective of the invention is for the investment of present production technique existence high, separation costs is high, large and the situation that is difficult to administer of quantity of three wastes provides a kind of and prepares the method for aromatic amine as raw material to mix nitro-chlorobenzene, and it is short that the method has technical process, speed of response is fast, selectivity is high, and sepn process is simple, and production cost is low, security is reliable, and production process is without the advantage of the three wastes.
The technical solution used in the present invention is:
A kind of method that is prepared aromatic amine by the mixing nitro-chlorobenzene, described method comprises:
(1) the mixing nitro-chlorobenzene of melting and ammoniacal liquor carry out ammonolysis reaction 5.5h～12h under 160～190 ℃, 3.5～10MPa condition, after reaction finishes, with reaction solution remove crystallisation by cooling after free ammonia and unreacted nitro-chlorobenzene, centrifugation obtains comprising the material that mixes N-methyl-p-nitroaniline, mother liquor condensing crystal after centrifugal separates, recyclable ammonium chloride wherein; The molar ratio of described mixing nitro-chlorobenzene and ammonia is 1: 6～16, and described ammoniacal liquor mass concentration is 15～50%; Described mixing nitro-chlorobenzene is that chlorobenzene is through the mixture of the nitrated p-Nitrophenyl chloride that makes, o-Nitrochlorobenzene and m-nitrochlorobenzene, in this mixture, p-Nitrophenyl chloride quality percentage composition is 30～68%, o-Nitrochlorobenzene quality percentage composition is 30～68%, and m-nitrochlorobenzene quality percentage composition is no more than 2% (generally 1%～2%);
Removing of free ammonia and unreacted nitro-chlorobenzene can adopt conventional cooling, ammonia excretion decompression or stripping mode to remove, and described cooling, decompression preferably are cooled to below 145 ℃, are decompressed to below 0.5MPa.Adopt the water vapor stripping to remove free ammonia and unreacted nitro-chlorobenzene, the stripping temperature is preferably 100～120 ℃.Adopt the water vapour stripping to remove free ammonia and unreacted nitro-chlorobenzene, specifically refer in temperature is the stripping tower of 100～120 ℃, ammonia solution material meets with the water vapour that rises under being drenched by the top of tower, form azeotropic, carry out removing free ammonia and m-nitrochlorobenzene after mass transfer, purification.Described stripping tower can be autoclave or with the stripping tower of column plate.
What (2) obtain in step (1) comprises the material that mixes N-methyl-p-nitroaniline, add solvent, catalyzer, carried out catalytic hydrogenation reaction 1.5～5 hours under 50～140 ℃, 0.3～2.0MPa, obtain comprising the product of benzene mixed diamines, the product of benzene mixed diamines then carries out rectifying separation and obtains Ursol D, O-Phenylene Diamine product after Separation and Recovery catalyzer, dealcoholysis dehydration; Described solvent is the alcohol of C1～C4; Described catalyzer is the conventional catalyzer that is used for shortening, as nickel catalyzator (comprising skeleton nickel, carrier nickel, reduced nickel and nickel borides), palladium catalyst (comprising palladous oxide, palladium black and carrier palladium) and platinum catalyst (comprising platinum oxide, platinum black and carrier platinum) etc.; The quality consumption of described catalyzer is for mixing 0.2%～5% of N-methyl-p-nitroaniline quality of material, and the mass ratio of described mixing N-methyl-p-nitroaniline material and solvent is 1: 1～6.
The involved chemical equation of the inventive method is as follows:
In described step (2), the described material that mixes N-methyl-p-nitroaniline that comprises, first be warmed up to 50～80 ℃ after adding solvent, N-methyl-p-nitroaniline is all dissolved, then progressively reduce temperature of charge to 10～30 ℃, after crystallization, centrifugation went out the part p-Nitroaniline, centrifuge mother liquor added catalyzer to carry out catalytic hydrogenation reaction again and prepares phenylenediamine.
Preferably, the ammonia concn that in step (1), ammonolysis reaction adds is 25～43%, and the molar ratio that mixes ammonia in nitro-chlorobenzene and ammoniacal liquor is 1: 7～12, and the ammonia solution time is 6h～10h.
In step (2), catalyzer is preferably skeleton nickel, carrier nickel, palladium carbon (Pd/C) or platinum.
In described step (2), rectifying separation is carried out under reduced pressure, preferably carries out under 15～70mHg, and tower top distillates O-Phenylene Diamine, distillates Ursol D at the bottom of tower.
The method that is prepared aromatic amine by the mixing nitro-chlorobenzene of the present invention, compared to traditional will the mixing carrying out respectively the ammonia solution after nitro-chlorobenzene raw material rectifying separation and prepare corresponding p-Nitroaniline and o-Nitraniline, carry out respectively by it technique that shortening prepares Ursol D and O-Phenylene Diamine again, its beneficial effect is mainly reflected in:
1. the pre-treatment that mixes the nitro-chlorobenzene raw material is required and can greatly reduce, thereby can reduce the preparation link, reduce energy consumption; Simultaneously with separate N-methyl-p-nitroaniline or phenylenediamine is compared, Separation of Nitrochlorobenzene is more difficult, exists technical process long, equipment complexity, the problem such as operational load is large.
2. with after Separation of Nitrochlorobenzene carry out the ammonia solution and compare with catalyst hydrogenation technique, mix nitroxyl chloride phenylamino solution and catalytic hydrogenation process and have that the preparation link is few, three wastes generation seldom, the characteristics such as energy consumption is low.
3. more be applicable to large-scale industrial production by mixing the direct ammonia solution of nitro-chlorobenzene and shortening, can plan as a whole to utilize, reduce production costs.
(4) description of drawings
Fig. 1 serves as reasons and mixes nitro-chlorobenzene and prepare the phenylenediamine process flow sheet;
(5) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1:
The mixing nitro-chlorobenzene 615kg of molten (is made by the nitration mixture adiabatic nitration by chlorobenzene, contain trace impurity, wherein the p-Nitrophenyl chloride mass content is 65.3%, and the o-Nitrochlorobenzene mass content is 33.2%, and the m-nitrochlorobenzene mass content is 0.8%) pump into 3M
3In stirred autoclave, mix with the ammoniacal liquor of the 2220kg that comes autogamy ammonia tank 30% (w/w) under whipped state, heat up and control temperature ammonolysis reaction 10 hours under 170～185 ℃, the condition of pressure at 3.5～4.9MPa, then be down to about 145 ℃ beginning ammonia excretions, the expellant gas water absorbs, and is used for preparation ammonia solution raw material ammonia water, and the reactor material after ammonia excretion pumps into stripping tower, with 0.5MPa steam stripping, overhead condensation reclaims ammonia and nitro-chlorobenzene.Material after stripping is cooling, cools to 30 ℃ of crystallizations, through standing sedimentation, centrifugation, obtains mixing N-methyl-p-nitroaniline 527kg, and centrifuge mother liquor can further be processed condensing crystal and reclaim ammonium chloride.
Take mixing N-methyl-p-nitroaniline 527kg obtained above, take methyl alcohol as solvent, skeleton nickel (Raney's nickel, Raney Ni) as catalyzer, carry out the low pressure liquid phase catalytic hydrogenation, 80 ℃ of temperature, carried out hydrogenating reduction under the condition of hydrogen pressure 1.5MPa 4 hours, methanol usage is 1600kg, and catalyst levels is 15.5kg, hydrogenation reaction finishes, dealcoholysis dehydration, then rectification under vacuum separates, and (carry out under 15～70mHg, 170～195 ℃, tower top distillates O-Phenylene Diamine, distillate Ursol D at the bottom of tower) go out Ursol D 261kg, O-Phenylene Diamine 132kg, purity is more than 99%.
Embodiment 2:
The mixing nitro-chlorobenzene 650kg of molten (is made by the nitration mixture adiabatic nitration by chlorobenzene, contain trace impurity, wherein the p-Nitrophenyl chloride mass content is 64%, and the o-Nitrochlorobenzene mass content is 34.5%, and the m-nitrochlorobenzene mass content is 0.7%) pump into 3M
3In the reactor that band stirs, mix with 33% (w/w) ammoniacal liquor of the 2350kg that comes autogamy ammonia tank under whipped state, heat up and control temperature ammonolysis reaction 10 hours under 160～182 ℃, the condition of pressure at 4.0～4.9MPa, then be cooled to about 145 ℃ beginning ammonia excretions, reactor material after ammonia excretion pumps into stripping tower, with 0.5MPa steam stripping, overhead condensation reclaims ammonia and nitro-chlorobenzene, material after stripping is through cooling, cool to 35 ℃ of crystallizations, through standing sedimentation, centrifugation, obtain mixing N-methyl-p-nitroaniline 552kg.
Take mixing N-methyl-p-nitroaniline 552kg obtained above, take ethanol as solvent, palladium carbon (10%Pd/C) is as catalyzer, carry out the low pressure liquid phase catalytic hydrogenation, 80 ℃ of temperature were carried out hydrogenating reduction 3.5 hours under the condition of hydrogen pressure 1.2MPa, the ethanol consumption is 1500kg, catalyst levels is 13.9kg, and hydrogenation reaction finishes, the dealcoholysis dehydration, rectification under vacuum again (separation condition is with embodiment 1), isolate Ursol D 269k,, O-Phenylene Diamine 144kg, purity is more than 99%.
Embodiment 3:
The mixing nitro-chlorobenzene 615kg (p-Nitrophenyl chloride is 65.3%, o-Nitrochlorobenzene 33.2%, m-nitrochlorobenzene 0.8%) of molten is pumped into 3M
3In stirred autoclave, mix with 30% the ammoniacal liquor of the 2220kg that comes autogamy ammonia tank under whipped state, heat up and control temperature ammonolysis reaction 10 hours under 170～185 ℃, the condition of pressure at 3.5～4.9MPa, then be down to about 145 ℃ beginning ammonia excretions, the expellant gas water absorbs, and is used for preparation ammonia solution raw material ammonia water, and the reactor material after ammonia excretion pumps into stripping tower, with 0.5MPa steam stripping, overhead condensation reclaims ammonia and nitro-chlorobenzene.Material after stripping is cooling, cools to 30 ℃ of crystallizations, through standing sedimentation, centrifugation, obtains mixing N-methyl-p-nitroaniline 527kg, and centrifuge mother liquor can further be processed condensing crystal and reclaim ammonium chloride.
Take mixing N-methyl-p-nitroaniline 350kg obtained above, add methyl alcohol 1000kg, be warmed up to 70 ℃ under whipped state, keep methanol eddy, all dissolve to N-methyl-p-nitroaniline, progressively reduce temperature of charge to 20 ℃, crystallization, filtration are filtered filter cake and are obtained p-Nitroaniline 128kg through vacuum-drying.Centrifuge mother liquor is squeezed into the hydrogenation still, add 5.2kgPt as catalyzer, carry out liquid phase catalytic hydrogenation, temperature 70 C, carried out hydrogenating reduction under the condition of hydrogen pressure 1.5MPa 4 hours, hydrogenation reaction finishes, the dealcoholysis dehydration, Ursol D 75kg, O-Phenylene Diamine 88kg are isolated in rectification under vacuum again (separation condition is with embodiment 1), and purity is more than 99%.
Claims (5)
1. one kind by the method for mixing nitro-chlorobenzene and prepare aromatic amine, and described method comprises:
(1) the mixing nitro-chlorobenzene of melting and ammoniacal liquor carry out ammonolysis reaction 5.5h～12h under 160～190 ℃, 3.5～10MPa condition, after reaction finishes, with reaction solution remove crystallisation by cooling after free ammonia and unreacted nitro-chlorobenzene, centrifugation obtains comprising the material that mixes N-methyl-p-nitroaniline; The molar ratio of described mixing nitro-chlorobenzene and ammonia is 1: 6～16, and described ammoniacal liquor mass concentration is 15～50%; Described mixing nitro-chlorobenzene is that chlorobenzene is through the mixture of the nitrated p-Nitrophenyl chloride that makes, o-Nitrochlorobenzene and m-nitrochlorobenzene;
What (2) obtain in step (1) comprises the material that mixes N-methyl-p-nitroaniline, add solvent, catalyzer, carried out catalytic hydrogenation reaction 1.5～5 hours under 50～140 ℃, 0.3～2.0MPa, obtain comprising the product of benzene mixed diamines, the product of benzene mixed diamines then carries out rectifying separation and obtains Ursol D, O-Phenylene Diamine product after Separation and Recovery catalyzer, dealcoholysis dehydration; Described solvent is the alcohol of C1～C4; The quality consumption of described catalyzer is for mixing 0.2%～5% of N-methyl-p-nitroaniline quality of material, and the mass ratio of described mixing N-methyl-p-nitroaniline material and solvent is 1: 1～6.
2. the method for claim 1, it is characterized in that in described step (2), the described material that mixes N-methyl-p-nitroaniline that comprises, first be warmed up to 50～80 ℃ after adding solvent, N-methyl-p-nitroaniline is all dissolved, then progressively reduce temperature of charge to 10～30 ℃, after crystallization, centrifugation went out the part p-Nitroaniline, centrifuge mother liquor added catalyzer to carry out catalytic hydrogenation reaction again and prepares phenylenediamine.
3. the method for claim 1, is characterized in that the ammonia concn that in step (1), ammonolysis reaction adds is 25～43%, and the molar ratio that mixes ammonia in nitro-chlorobenzene and ammoniacal liquor is 1: 7～12, and the ammonia solution time is 6h～10h.
4. the method for claim 1, is characterized in that in step (2), catalyzer is skeleton nickel, carrier nickel, palladium carbon or platinum.
5. the method for claim 1 is characterized in that: in described step (2), rectifying separation is carried out under 15～70mHg, and tower top distillates O-Phenylene Diamine, distillates Ursol D at the bottom of tower.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103420850A (en) * | 2013-07-19 | 2013-12-04 | 浙江闰土股份有限公司 | Continuous production method of paranitroaniline |
| CN103787893A (en) * | 2013-11-20 | 2014-05-14 | 南通波涛化工有限公司 | O-phenylenediamine medium-pressure catalytic hydrogenation process |
| CN107488117A (en) * | 2017-07-13 | 2017-12-19 | 安徽东至广信农化有限公司 | A kind of preparation method of intermediate o-phenylenediamine for carbendazim production |
| CN110156609A (en) * | 2019-05-09 | 2019-08-23 | 江苏扬农化工集团有限公司 | A method of purification paranitroanilinum |
| CN113582852A (en) * | 2020-04-30 | 2021-11-02 | 浙江省常山长盛化工有限公司 | Method for producing dinitroaniline |
| CN115160150A (en) * | 2022-06-30 | 2022-10-11 | 国药集团化学试剂有限公司 | Preparation method of high-purity p-phenylenediamine |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103420850A (en) * | 2013-07-19 | 2013-12-04 | 浙江闰土股份有限公司 | Continuous production method of paranitroaniline |
| CN103787893A (en) * | 2013-11-20 | 2014-05-14 | 南通波涛化工有限公司 | O-phenylenediamine medium-pressure catalytic hydrogenation process |
| CN107488117A (en) * | 2017-07-13 | 2017-12-19 | 安徽东至广信农化有限公司 | A kind of preparation method of intermediate o-phenylenediamine for carbendazim production |
| CN110156609A (en) * | 2019-05-09 | 2019-08-23 | 江苏扬农化工集团有限公司 | A method of purification paranitroanilinum |
| CN110156609B (en) * | 2019-05-09 | 2022-04-22 | 江苏扬农化工集团有限公司 | Method for purifying p-nitroaniline |
| CN113582852A (en) * | 2020-04-30 | 2021-11-02 | 浙江省常山长盛化工有限公司 | Method for producing dinitroaniline |
| CN115160150A (en) * | 2022-06-30 | 2022-10-11 | 国药集团化学试剂有限公司 | Preparation method of high-purity p-phenylenediamine |
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