CN109553537A - A kind of paranitroanilinum synthesis technology - Google Patents
A kind of paranitroanilinum synthesis technology Download PDFInfo
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- CN109553537A CN109553537A CN201811489420.5A CN201811489420A CN109553537A CN 109553537 A CN109553537 A CN 109553537A CN 201811489420 A CN201811489420 A CN 201811489420A CN 109553537 A CN109553537 A CN 109553537A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
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Abstract
The present invention relates to synthesis technology fields, and in particular to a kind of paranitroanilinum synthesis technology, preparation step include that preheating, hybrid reaction, azeotropic hydrolysis and separating-purifying four are most of;The present invention provides a kind of paranitroanilinum synthesis technologies, azeotropic hydrolysis process is carried out by reducing temperature, utilize the congener generated in nitration reaction and the correlation for reacting the temperature carried out, reduce the activation capacity that electrophilic reaction replaces, improve the selectivity that group generates para-compound on phenyl ring, it is that side reaction substance passes through hydrolysed filtrate removing by the neighbour generated in reaction, guarantee the purity for the final product that final step is filtered under diminished pressure, the present invention is not needed compared to traditional handicraft using expensive special solvent, it does not require to carry out waterless operation, simplify the condition requirement of technique, the purity is high for the final product paranitroanilinum being prepared, realize the efficient utilization to reaction mass.
Description
Technical field
The present invention relates to product synthesis technology fields, and in particular to a kind of paranitroanilinum synthesis technology.
Background technique
Paranitroanilinum, yellow needles, high poison, Yi Shenghua.It is slightly soluble in cold water, is dissolved in boiling water, ethyl alcohol, ether, benzene
And acid solution.It is widely used in the artificial synthesized chemicals of dye industry, is the intermediate of a variety of printing and dyeing and medication chemistry product,
It can be used for analytical reagent.
Nitroaniline be also be the particularly important intermediate of dye industry, can be directly used for synthesis kind have: directly it is sun-proof
Black G, direct green B, BE, 2B-2N, black green NB, directly ash D, Acid Black 10B, ATT, disperse red P-4G, sun are from deep yellow 2RL, fur
Black D, p-phenylenediamine, ortho-chlor-para nitraniline, chloro- 4 nitroaniline of 2.6- bis-, 5- nitro -2- chlorophenol etc., can also synthetic pesticide
Botran, medicine card willow are swollen;It simultaneously or the raw material of anti-aging agent, light stabilizer, developer etc., is a kind of important organic synthesis
Raw material.
There is unstable product quality, reactions for the intermittent ammonolysis process production technology that domestic manufacturer generallys use
Period is long, and production energy consumption is high, while generating the defect of a large amount of brine wastes, as Environmental Protection in China requires to be increasingly stringenter, urgently
Need to develop it is new it is environmental-friendly, low energy consumption, the paranitroanilinum new technique for synthesizing of stable product quality, it is raw to be just able to satisfy enterprise
At and environmental and ecological protection common prescription.
Summary of the invention
Therefore, the present invention provides a kind of paranitroanilinum synthesis technology, the present invention does not need to make compared to traditional handicraft
It with expensive special solvent, does not require to carry out waterless operation, simplifies the condition requirement of technique, the final product pair being prepared
The purity is high of nitroaniline, and conversion ratio can reach 95% or more, realize and utilize to the Efficient Conversion of reaction mass, realization
Good economical benefit.
In order to achieve the above object, the present invention is achieved by the following technical programs:
A kind of paranitroanilinum synthesis technology, comprising the following steps:
(1) it preheats: paranitrochlorobenzene is dissolved in suitable solvent, adjust pH value to 6.5-8.5, being put into temperature is
85-95 DEG C, revolving speed obtains mixture A to stir 30-60min in the blender of 160-200r/min;
(2) it hybrid reaction: will be put into reactor by mixture A, ammonium hydroxide and the phase transfer catalyst of heating, wherein mixing
Closing the ratio between amount of substance of object A and ammonium hydroxide is 1:5-1:10, is reacted at high temperature, and the pressure for reacting progress is 2.0-
5.0MPa obtains mixture B after being cooled to room temperature;
(3) azeotropic hydrolyzes: sodium carbonate liquor will be added in mixture B, adjusting pH value to 9.5-10 is total at 45-55 DEG C
Boiling water solution, obtains mixture C;
(4) separating-purifying: mixture C is led into cooling water temperature, processing is filtered under diminished pressure after cooling, isolates p-nitrophenyl
Amine.
Preferably, solvent described in step (1) is dimethyl ether or toluene.
Preferably, sodium hydroxide or potassium hydroxide is used to carry out pH value adjusting in the step (1) and step (3).
Preferably, the concentration quality of ammonium hydroxide described in step (2) is 30% or more.
Preferably, the time reacted in step (2) is 2-4h.
Preferably, the type of reactor described in step (2) is fixed bed catalytic reactor, shell and tube reactor or continuous
Stirred tank.
Preferably, the type of phase transfer catalyst described in step (2) is BTEAC, TEBA, 4-propyl bromide or 12
Alkyl trimethyl ammonium chloride is one such or several mixtures.
Preferably, temperature after cooling is 5-20 DEG C in step (2).
The utility model has the advantages that
In the technique that the present invention synthesizes, the p-nitrophenyl as synthesis material is dissolved in solvent carrying out at preheating first
Reason enables what p-nitrophenyl can be more uniform to be dispersed among ammonium hydroxide, molten by the way that powdered raw material to be dispersed in by heating
Among agent, using the product between solvent, effectively improve in the classification of filling material effect in hybrid reaction step between mixing liquid
Fruit enables two component materials to be further uniformly distributed on molecular level, and compared to traditional handicraft do not need using
Expensive special solvent does not require to carry out waterless operation, simplifies the condition requirement of technique;By being added in hybrid reaction
Enter the activation energy that phase transfer catalyst participates in reaction reduction reaction together, so that raw material object is not had to also proper energy salts substances can be efficient
Conversion, avoids the waste water for generating a large amount of saliferous, it is difficult to carry out waste water environmental protection treatment;And after completing hybrid reaction, by adding
Enter sodium carbonate liquor, under the reaction condition for promoting pH value, reduces temperature and carry out azeotropic hydrolysis process, using in nitration reaction
The activation capacity that the congener of generation replaces with the correlation for reacting the temperature carried out, reduction electrophilic reaction, improves group and exists
The selectivity that para-compound is generated on phenyl ring removes the neighbour generated in reaction for side reaction substance by hydrolysed filtrate,
Guarantee the purity for the final product that final step is filtered under diminished pressure.
The purity is high of the preparation-obtained final product paranitroanilinum of synthesis technology provided by the invention, and conversion ratio can
Reach 95% or more, realizes to the Efficient Conversion utilization of reaction mass and good economic effect.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention,
Technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is the present invention one
Divide embodiment, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making
Every other embodiment obtained, shall fall within the protection scope of the present invention under the premise of creative work.
Embodiment 1:
A kind of paranitroanilinum synthesis technology, comprising the following steps:
(1) it preheating: paranitrochlorobenzene is dissolved in suitable solvent, adjusting pH value to 6.5, being put into temperature is 95 DEG C,
40min is stirred in the blender that revolving speed is 180r/min, obtains mixture A;
(2) it hybrid reaction: will be put into reactor by mixture A, ammonium hydroxide and the phase transfer catalyst of heating, wherein mixing
Closing the ratio between amount of substance of object A and ammonium hydroxide is 1:5-, is reacted at high temperature, and the pressure for reacting progress is 3.5MPa, is cooled to
Mixture B is obtained after room temperature;
(3) azeotropic hydrolyzes: sodium carbonate liquor will be added in mixture B, adjust pH value to 9.5, azeotropic hydrolyzes at 50 DEG C,
Obtain mixture C;
(4) separating-purifying: mixture C is led into cooling water temperature, processing is filtered under diminished pressure after cooling, isolates p-nitrophenyl
Amine.
Solvent is dimethyl ether in step (1).
Step (1) carries out pH value adjusting using sodium hydroxide, uses potassium hydroxide to carry out pH value adjusting in step (3).
The concentration quality of ammonium hydroxide is 35% in step (2).
The time reacted in step (2) is 2.5h.
The type of reactor is fixed bed catalytic reactor in step (2).
The type of phase transfer catalyst described in step (2) is BTEAC.
Temperature after cooling is 8 DEG C in step (4).
Embodiment 2:
A kind of paranitroanilinum synthesis technology, comprising the following steps:
(1) it preheats: paranitrochlorobenzene is dissolved in suitable solvent, adjust pH value to 6.5-8.5, being put into temperature is 88
DEG C, 60min is stirred in the blender that revolving speed is 160r/min, obtains mixture A;
(2) it hybrid reaction: will be put into reactor by mixture A, ammonium hydroxide and the phase transfer catalyst of heating, wherein mixing
Closing the ratio between amount of substance of object A and ammonium hydroxide is 1:7, is reacted at high temperature, and the pressure for reacting progress is 2.5MPa, is cooled to room
Mixture B is obtained after temperature;
(3) azeotropic hydrolyzes: sodium carbonate liquor will be added in mixture B, adjust pH value to 10, azeotropic hydrolyzes at 55 DEG C,
Obtain mixture C;
(4) separating-purifying: mixture C is led into cooling water temperature, processing is filtered under diminished pressure after cooling, isolates p-nitrophenyl
Amine.
Solvent is toluene in step (1).
It is all made of potassium hydroxide in step (1) and step (3) and carries out pH value adjusting.
The concentration quality of ammonium hydroxide is 40% or more in step (2).
The time reacted in step (2) is 3.5h.
The type of reactor is shell and tube reactor in step (2).
The type of phase transfer catalyst is the mixture of BTEAC and 4-propyl bromide in step (2).
Temperature after cooling is 10 DEG C in step (4).
Embodiment 3:
A kind of paranitroanilinum synthesis technology, comprising the following steps:
(1) it preheating: paranitrochlorobenzene is dissolved in suitable solvent, adjusting pH value to 8.5, being put into temperature is 95 DEG C,
45min is stirred in the blender that revolving speed is 200r/min, obtains mixture A;
(2) it hybrid reaction: will be put into reactor by mixture A, ammonium hydroxide and the phase transfer catalyst of heating, wherein mixing
Closing the ratio between amount of substance of object A and ammonium hydroxide is 1:10, is reacted at high temperature, and the pressure for reacting progress is 5.0MPa, is cooled to
Mixture B is obtained after room temperature;
(3) azeotropic hydrolyzes: sodium carbonate liquor will be added in mixture B, adjust pH value to 10, azeotropic hydrolyzes at 50 DEG C,
Obtain mixture C;
(4) separating-purifying: mixture C is led into cooling water temperature, processing is filtered under diminished pressure after cooling, isolates p-nitrophenyl
Amine.
Solvent is toluene in step (1).
PH value adjusting is carried out using sodium hydroxide in step (1) and step (3).
The concentration quality of ammonium hydroxide is 38% or more in step (2).
The time reacted in step (2) is 3.5h.
The type continuous stirred tank of reactor in step (2).
The type of phase transfer catalyst is TEBA, 4-propyl bromide and dodecyl trimethyl ammonium chloride in step (2)
Mixture.
Temperature after cooling is 20 DEG C in step (4).
Embodiment 4:
A kind of paranitroanilinum synthesis technology, comprising the following steps:
(1) it preheating: paranitrochlorobenzene is dissolved in suitable solvent, adjusting pH value to 7.0, being put into temperature is 86 DEG C,
55min is stirred in the blender that revolving speed is 160r/min, obtains mixture A;
(2) it hybrid reaction: will be put into reactor by mixture A, ammonium hydroxide and the phase transfer catalyst of heating, wherein mixing
Closing the ratio between amount of substance of object A and ammonium hydroxide is 1:9, is reacted at high temperature, and the pressure for reacting progress is 5.0MPa, is cooled to room
Mixture B is obtained after temperature;
(3) azeotropic hydrolyzes: sodium carbonate liquor will be added in mixture B, adjust pH value to 9.5, azeotropic hydrolyzes at 52 DEG C,
Obtain mixture C.
(4) separating-purifying: mixture C is led into cooling water temperature, processing is filtered under diminished pressure after cooling, isolates p-nitrophenyl
Amine.
Solvent is dimethyl ether in step (1).
Step (1) carries out pH value adjusting using sodium hydroxide, uses potassium hydroxide to carry out pH value adjusting in step (3).
The concentration quality of ammonium hydroxide is 30% or more in step (2).
The time reacted in step (2) is 2h.
The type of reactor is fixed bed catalytic reactor in step (2).
The type of phase transfer catalyst described in step (2) is dodecyl trimethyl ammonium chloride.
Temperature after cooling is 5-20 DEG C in step (4).
Embodiment 5:
A kind of paranitroanilinum synthesis technology, comprising the following steps:
(1) it preheating: paranitrochlorobenzene is dissolved in suitable solvent, adjusting pH value to 6.5, being put into temperature is 90 DEG C,
35min is stirred in the blender that revolving speed is 200r/min, obtains mixture A;
(2) it hybrid reaction: will be put into reactor by mixture A, ammonium hydroxide and the phase transfer catalyst of heating, wherein mixing
Closing the ratio between amount of substance of object A and ammonium hydroxide is 1:5, is reacted at high temperature, and the pressure for reacting progress is 3.5MPa, is cooled to room
Mixture B is obtained after temperature;
(3) azeotropic hydrolyzes: sodium carbonate liquor will be added in mixture B, adjust pH value to 9.5, azeotropic hydrolyzes at 55 DEG C,
Obtain mixture C;
(4) separating-purifying: mixture C is led into cooling water temperature, processing is filtered under diminished pressure after cooling, isolates p-nitrophenyl
Amine.
Solvent described in step (1) is toluene.
It is all made of potassium hydroxide in step (1) and step (3) and carries out pH value adjusting.
The concentration quality of ammonium hydroxide is 40% or more in step (2).
The time reacted in step (2) is 3.5h.
The type of reactor described in step (2) is continuous stirred tank.
The type of phase transfer catalyst described in step (2) is the mixture of BTEAC, TEBA and 4-propyl bromide.
Temperature after cooling is 20 DEG C in step (4).
The paranitroanilinum obtained by above-described embodiment carries out gas chromatographic analysis and calculates conversion ratio, and test result is such as
Following table:
Embodiment | Gas chromatographic analysis purity | Conversion ratio |
Embodiment 1 | 95.5% | 96% |
Embodiment 2 | 96.2% | 95% |
Embodiment 3 | 96.4% | 96% |
Embodiment 4 | 97.0% | 98% |
Embodiment 5 | 95.8% | 97% |
By above-mentioned test result it is found that the preparation-obtained final product paranitroanilinum of synthesis technology provided by the present invention
Purity is high, and conversion ratio can reach 95% or more, realize and utilize to the Efficient Conversion of reaction mass, the economic effect of realization
It is good.
It should be noted that, in this document, relational terms such as first and second and the like are used merely to a reality
Body or operation are distinguished with another entity or operation, are deposited without necessarily requiring or implying between these entities or operation
In any actual relationship or order or sequence.Moreover, the terms "include", "comprise" or its any other variant are intended to
Non-exclusive inclusion, so that the process, method, article or equipment including a series of elements is not only wanted including those
Element, but also including other elements that are not explicitly listed, or further include for this process, method, article or equipment
Intrinsic element.In the absence of more restrictions, the element limited by sentence "including a ...", it is not excluded that
There is also other identical elements in process, method, article or equipment including element.
The above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations;Although with reference to the foregoing embodiments
Invention is explained in detail, those skilled in the art should understand that: it still can be to aforementioned each implementation
Technical solution documented by example is modified or equivalent replacement of some of the technical features;And these modification or
Replacement, the spirit and scope for technical solution of various embodiments of the present invention that it does not separate the essence of the corresponding technical solution.
Claims (8)
1. a kind of paranitroanilinum synthesis technology, which comprises the following steps:
(1) it preheats: paranitrochlorobenzene is dissolved in suitable solvent, adjust pH value to 6.5-8.5, being put into temperature is 85-95
DEG C, 30-60min is stirred in the blender that revolving speed is 160-200r/min, obtains mixture A;
(2) it hybrid reaction: will be put into reactor by mixture A, ammonium hydroxide and the phase transfer catalyst of heating, wherein mixture
The ratio between amount of substance of A and ammonium hydroxide is 1:5-1:10, is reacted at high temperature, and the pressure for reacting progress is 2.0-5.0MPa, cold
But to obtaining mixture B after room temperature;
(3) azeotropic hydrolyzes: sodium carbonate liquor will be added in mixture B, adjusting pH value is to 9.5-10, the azeotropic water at 45-55 DEG C
Solution, obtains mixture C;
(4) separating-purifying: mixture C is led into cooling water temperature, processing is filtered under diminished pressure after cooling, isolates paranitroanilinum.
2. a kind of paranitroanilinum synthesis technology according to claim 1, it is characterised in that: described in the step (1)
Solvent is dimethyl ether or toluene.
3. a kind of paranitroanilinum synthesis technology according to claim 1, it is characterised in that: the step (1) and step
(3) pH value adjusting is carried out using sodium hydroxide or potassium hydroxide in.
4. a kind of paranitroanilinum synthesis technology according to claim 1, it is characterised in that: described in the step (2)
The concentration quality of ammonium hydroxide is 30% or more.
5. a kind of paranitroanilinum synthesis technology according to claim 1, it is characterised in that: reaction in the step (2)
Time be 2-4h.
6. a kind of paranitroanilinum synthesis technology according to claim 1, it is characterised in that: described in the step (2)
The type of reactor is fixed bed catalytic reactor, shell and tube reactor or continuous stirred tank.
7. a kind of paranitroanilinum synthesis technology according to claim 1, it is characterised in that: described in the step (2)
The type of phase transfer catalyst be BTEAC, TEBA, 4-propyl bromide or dodecyl trimethyl ammonium chloride it is one such or
Several mixtures.
8. a kind of paranitroanilinum synthesis technology according to claim 1, it is characterised in that: cooling in the step (4)
Temperature afterwards is 5-20 DEG C.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
CN113663727A (en) * | 2021-09-18 | 2021-11-19 | 黔南高新区绿色化工技术研究院有限公司 | Preparation method of supported catalyst with high specific surface area and application of supported catalyst in p-nitroaniline synthesis |
CN113694916A (en) * | 2021-09-17 | 2021-11-26 | 黔南高新区绿色化工技术研究院有限公司 | Method for synthesizing p-nitroaniline based on hierarchical porous carbon fiber supported phase transfer catalyst |
-
2018
- 2018-12-06 CN CN201811489420.5A patent/CN109553537A/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
CN113694916A (en) * | 2021-09-17 | 2021-11-26 | 黔南高新区绿色化工技术研究院有限公司 | Method for synthesizing p-nitroaniline based on hierarchical porous carbon fiber supported phase transfer catalyst |
CN113694916B (en) * | 2021-09-17 | 2024-02-20 | 黔南高新区绿色化工技术研究院有限公司 | Method for synthesizing paranitroaniline based on hierarchical pore carbon fiber supported phase transfer catalyst |
CN113663727A (en) * | 2021-09-18 | 2021-11-19 | 黔南高新区绿色化工技术研究院有限公司 | Preparation method of supported catalyst with high specific surface area and application of supported catalyst in p-nitroaniline synthesis |
CN113663727B (en) * | 2021-09-18 | 2024-02-20 | 黔南高新区绿色化工技术研究院有限公司 | Preparation method of supported catalyst with high specific surface area and application of supported catalyst in synthesis of p-nitroaniline |
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