CN102199094A - Production method of parachloroaniline - Google Patents
Production method of parachloroaniline Download PDFInfo
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- CN102199094A CN102199094A CN2011100871916A CN201110087191A CN102199094A CN 102199094 A CN102199094 A CN 102199094A CN 2011100871916 A CN2011100871916 A CN 2011100871916A CN 201110087191 A CN201110087191 A CN 201110087191A CN 102199094 A CN102199094 A CN 102199094A
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- CN
- China
- Prior art keywords
- acid amide
- reactor
- chlorobenzoic acid
- production method
- methyl alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a production method of parachloroaniline, relating to the technical field of chemical production, particularly to a production process of parachloroaniline. In the production method, methanol is used as a solvent, and the addition of dechlorination inhibitor can lower reaction temperature, lower reaction pressure and improve reaction conversion rate. The reaction materials are subjected to sealed filtering, the catalyst is recycled, water is separated out and sampling analysis shows that the parachloroaniline content is 98.3% and the yield reaches 97.76%.
Description
Technical field
The present invention relates to chemical production technical field, particularly the production technique of p-Chlorobenzoic acid amide.
Background technology
P-Chlorobenzoic acid amide also is medicine (favorable to the people peaceful, Phenacetin), pesticide intermediate mainly as the intermediate of preparation azoic dyestuff and Naphthol AS-LB, and red 202 the intermediate of making paints also is used to produce the coupler of colour cinefilm.Pure product are colourless to faint yellow crystallization, 69.5 ℃ of fusing points, 232 ℃ of boiling points, 113 ℃ of flash-points. be dissolved in hot water, be soluble in alcohol, ether, acetone and dithiocarbonic anhydride.
The production of existing p-Chlorobenzoic acid amide is raw material with the p-Nitrophenyl chloride mainly, makes p-Chlorobenzoic acid amide through reduction reaction.Reducing process has iron powder reducing method, zinc powder reduction method, hydrogenating reduction method etc.The zinc powder reduction method is higher because of production cost, and big production generally do not adopted.The iron powder reducing method is difficult for handling because of the iron mud that produces, and environmental pollution is heavier, and manufacturer has stopped using this method substantially.The hydrogenating reduction method utilizes skeletal nickel catalyst, ethanol reduction p-Nitrophenyl chloride to prepare p-Chlorobenzoic acid amide, though this method is applicable to continuous mass production, but easily produces the shortcoming that by product, product yield are not high and production cost is high in process of production.
Summary of the invention
The object of the invention is to propose a kind of environmental protection, a kind of production method of p-Chlorobenzoic acid amide efficiently.
It is solvent that the present invention adopts with methyl alcohol, adds dechlorination inhibitor hydrogenating reduction p-Nitrophenyl chloride and produces p-Chlorobenzoic acid amide.
It is solvent that new production method adopts methyl alcohol, produces p-Chlorobenzoic acid amide with dechlorination inhibitor hydrogenating reduction p-Nitrophenyl chloride.
The present invention is solvent with methyl alcohol, adds the dechlorination inhibitor and makes that temperature of reaction is low, reaction pressure is low, and reaction conversion ratio is higher.Reaction mass is recycled catalyzer after airtight filtration, divide the water sampling analysis, content 98.3%, and yield reaches 97.76%.
Concrete steps of the present invention are as follows:
1) aqueous solution of methyl alcohol, dechlorination inhibitor, p-Nitrophenyl chloride and nickel-alumina catalyst is added reactor respectively after, closed reactor;
2) with air in the nitrogen replacement reactor;
3) with the double displacement gas reactor of hydrogen;
4) stir and make reactor be warming up to 55 ± 5 ℃ after, feed hydrogen, heat up, under reactor temperature is 75～80 ℃, the condition of pressure 0.80～0.85MPa, carry out hydrogenation reduction;
5) reaction finishes the back blowing, and filtered while hot is isolated nickel-alumina catalyst;
6) reaction mixture was obtained p-Chlorobenzoic acid amide behind the water in static minute.
Advantage of the present invention is:
1, is solvent with methyl alcohol, is easy to recycle, can reduce production costs;
2, add the dechlorination inhibitor and participate in reaction, it is higher that by product reduces transformation efficiency less, can improve product yield;
3, temperature of reaction is low, pressure is low, speed fast (3-3.5 hour), reaction process relatively are easy to control;
4, adopt the closed strainer, recycle catalyzer, reduce the products production cost.
The mass ratio that feeds intake of methyl alcohol of the present invention, dechlorination inhibitor and p-Nitrophenyl chloride is 1.21 ︰, 0.045 ︰ 1.
Embodiment
One, weighing:
Take by weighing 800kg methyl alcohol, 30kg dechlorination inhibitor, 660kg p-Nitrophenyl chloride respectively.
7 kg nickel-alumina catalysts and 3 kg water are mixed, form the nickel-alumina catalyst aqueous solution, stand-by.
Two, produce p-Chlorobenzoic acid amide:
1, methyl alcohol, dechlorination inhibitor, p-Nitrophenyl chloride and the nickel-alumina catalyst aqueous solution are added reactor successively.
2, closed reactor is with air in replacement reaction kettle of nitrogen of 0.3Mpa.
3, use the twice replaced reaction gas reactor of nitrogen of 0.3Mpa again.
4, with 0.5Mpa hydrogen continuous quadratic replacement(metathesis)reaction gas reactor.
5, closed reactor, be warming up to 55 ℃ after, open agitator in the reactor.
6, feed hydrogen and carry out hydrogenating reduction, the control reactor temperature is 75～80 ℃, pressure 0.80～0.85MPa, about 3-3.5 of reaction times hour, finishes.
7, filtered while hot is carried out recycling with nickel-alumina catalyst.
8, with remaining reaction mixture static after, tell lower floor's moisture, obtain the upper strata p-Chlorobenzoic acid amide.
Reaction process equation of the present invention:
Cl(C
6H
4)NO
2+3H
2→Cl(C
6H
4)NH
2+2H
2O
Three, detect:
The sampling analysis product purity is 98.3%, and product yield is 97.76%.
Claims (3)
1. a kind of production method of p-Chlorobenzoic acid amide, it is characterized in that adopting methyl alcohol is solvent, produces p-Chlorobenzoic acid amide with dechlorination inhibitor hydrogenating reduction p-Nitrophenyl chloride.
2. according to a kind of production method of the described p-Chlorobenzoic acid amide of claim 1, it is characterized in that may further comprise the steps:
1) aqueous solution of methyl alcohol, dechlorination inhibitor, p-Nitrophenyl chloride and nickel-alumina catalyst is added reactor respectively after, closed reactor;
2) with air in the nitrogen replacement reactor;
3) with the double displacement gas reactor of hydrogen;
4) stir and make reactor be warming up to 55 ± 5 ℃ after, feed hydrogen, heat up, under reactor temperature is 75～80 ℃, the condition of pressure 0.80～0.85MPa, carry out hydrogenation reduction;
5) reaction finishes the back blowing, and filtered while hot is isolated nickel-alumina catalyst;
6) reaction mixture was obtained p-Chlorobenzoic acid amide behind the water in static minute.
3. according to a kind of production method of the described p-Chlorobenzoic acid amide of claim 2, the mass ratio that feeds intake that it is characterized in that described methyl alcohol, dechlorination inhibitor and p-Nitrophenyl chloride is 1.21 ︰, 0.045 ︰ 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100871916A CN102199094A (en) | 2011-04-08 | 2011-04-08 | Production method of parachloroaniline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100871916A CN102199094A (en) | 2011-04-08 | 2011-04-08 | Production method of parachloroaniline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102199094A true CN102199094A (en) | 2011-09-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011100871916A Pending CN102199094A (en) | 2011-04-08 | 2011-04-08 | Production method of parachloroaniline |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102199094A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960936A (en) * | 1987-12-31 | 1990-10-02 | Ciba-Geigy Corporation | Process for the preparation of halogenated aromatic primary amines |
| CN1962608A (en) * | 2006-11-24 | 2007-05-16 | 中北大学 | Catalytic hydrogenation method for preparing 3,4-dichloroaniline |
| CN101333169A (en) * | 2007-03-01 | 2008-12-31 | 淮安嘉诚高新化工股份有限公司 | Method for producing o-chloroaniline |
| CN101774930A (en) * | 2010-02-10 | 2010-07-14 | 江苏康恒化工有限公司 | Method for preparing m-chloro aniline |
| CN101774931A (en) * | 2010-02-10 | 2010-07-14 | 江苏康恒化工有限公司 | Method for preparing o-chloroaniline by catalytic hydrogenation |
-
2011
- 2011-04-08 CN CN2011100871916A patent/CN102199094A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960936A (en) * | 1987-12-31 | 1990-10-02 | Ciba-Geigy Corporation | Process for the preparation of halogenated aromatic primary amines |
| CN1962608A (en) * | 2006-11-24 | 2007-05-16 | 中北大学 | Catalytic hydrogenation method for preparing 3,4-dichloroaniline |
| CN101333169A (en) * | 2007-03-01 | 2008-12-31 | 淮安嘉诚高新化工股份有限公司 | Method for producing o-chloroaniline |
| CN101774930A (en) * | 2010-02-10 | 2010-07-14 | 江苏康恒化工有限公司 | Method for preparing m-chloro aniline |
| CN101774931A (en) * | 2010-02-10 | 2010-07-14 | 江苏康恒化工有限公司 | Method for preparing o-chloroaniline by catalytic hydrogenation |
Non-Patent Citations (2)
| Title |
|---|
| 于万朋等: "催化加氢制备4-氯苯胺工艺研究", 《河北化工》, vol. 32, no. 12, 31 December 2009 (2009-12-31), pages 26 - 27 * |
| 胡拖平等: "单氯代硝基苯加氢还原时脱氯规律的研究", 《染料工业》, vol. 37, no. 6, 30 June 2000 (2000-06-30), pages 11 - 12 * |
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Application publication date: 20110928 |