CN102816074A - Synthesis method of p-n-butylaniline - Google Patents
Synthesis method of p-n-butylaniline Download PDFInfo
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- CN102816074A CN102816074A CN2012103051932A CN201210305193A CN102816074A CN 102816074 A CN102816074 A CN 102816074A CN 2012103051932 A CN2012103051932 A CN 2012103051932A CN 201210305193 A CN201210305193 A CN 201210305193A CN 102816074 A CN102816074 A CN 102816074A
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Abstract
The invention relates to a synthesis method of p-n-butylaniline. The method provided in the invention comprises the steps of: a. adding aniline, n-butanol and a catalyst into a reactor to perform a condensation reaction; b. hydrolyzing a reaction product, and conducting oil-water separation, thus obtaining a crude product; and c. subjecting the crude product to reduced pressure rectification so as to obtain p-n-butylaniline. The method is characterized in that: in step a, the aniline, the n-butanol and the catalyst that are added into the reactor are in a weight ratio of 1:(0.8-1.1):(0.4-0.85), the temperature of the condensation reaction is 220-240DEG C, the pressure of the condensation reaction is 2-5.0MPa, and the time of the condensation reaction is 6-24 hours; in the reaction process, the reactor discharges the reaction generated water out of the reaction system. The invention provided in the invention can improve the conversion rate and reduce the separation difficulty.
Description
Technical field
The present invention relates to a kind of compound method to n-butyl aniline.
Background technology
The production of prior art is mainly following three kinds to the method for n-butyl aniline: butylbenzene restore nitrification method, 4-butyl-1-bromobenzene ammonolysis process, aniline and butanols direct synthesis technique.
In butylbenzene restore nitrification method, the nitration reaction hazardous, nitrated and reduction produces a large amount of waste water and solid waste, and is more hard to manage.
4-butyl-1-bromobenzene ammonolysis process is high to equipment requirements, and reaction conditions is relatively harsher, and product needed is used multiple SX, and industriallization is difficult.
Comparatively speaking; Aniline and butanols direct synthesis technique have that three-waste pollution is less, product purity is than advantages such as height; It adds aniline, butanols and catalyzer in the reactor drum and synthesizes, and the reaction products therefrom can obtain n-butyl aniline through comparatively terse technologies such as hydrolysis, rectifying.Yet existing this method in process of production, aspects such as proportion of raw materials, reaction pressure, reaction times is provided with unreasonable, has that conversion rate of products is not high, the shortcoming of separation difficulty.
Summary of the invention
Technical problem to be solved by this invention is to overcome deficiency of the prior art and a kind of compound method to n-butyl aniline is provided, and can improve transformation efficiency, reduce separating difficulty.
The technical scheme that the present invention solves the problems of the technologies described above employing is: a kind of compound method to n-butyl aniline comprises the steps: a, aniline, butanols and catalyzer is added in the reaction unit carry out condensation reaction; Product after b, reaction are accomplished carries out oily water separation after hydrolysis, obtain the product bullion; C, the product bullion is obtained n-butyl aniline through rectification under vacuum; It is characterized in that:
Among the step a, add aniline, propyl carbinol and catalyzer in the reactor drum by weight being 1: (0.8～1.1): (0.4～0.85), setting-up point are 220～240 ℃, and condensation reaction pressure 2.0～5.0 MPa, condensation reaction time are 6～24 hours; In the reaction process, reaction unit will react the water that generates and discharge reaction system.
Among the step a of the present invention, aniline, propyl carbinol and catalyzer in the adding reactor drum are by weight being 1:0.8:0.4, and setting-up point is 220 ℃, and condensation reaction pressure 2.0 MPa, condensation reaction time are 6 hours.
Among the step a of the present invention, aniline, propyl carbinol and catalyzer in the adding reactor drum are by weight being 1:1.1:0.85, and setting-up point is 240 ℃, and condensation reaction pressure 5.0 MPa, condensation reaction time are 24 hours.
Among the step a of the present invention, aniline, propyl carbinol and catalyzer in the adding reactor drum are by weight being 1:0.95:0.8, and setting-up point is 230 ℃, and condensation reaction pressure 3.0 MPa, condensation reaction time are 12 hours.
Catalyzer of the present invention is a Lewis acid.
The present invention compared with prior art has following advantage and effect: 1, suitable reaction temperature, reaction times, reaction pressure, reduced the generation of by product, and environmental; 2, proper raw material proportioning, the transformation efficiency of raising product reduces cost; 3, on technology, will react the water that generates and remove, and break chemical equilibrium, and improve transformation efficiency, products therefrom gets final product through hydrolysis, rectifying.The present invention is simple and practical, and raw material is easy to get, and the transformation efficiency of reaction can improve 20%, and reacted product content improves, and makes to be prone to rectifying, and product purity is more than 98% after the rectifying, and cost reduces, and three waste discharge is few.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
Below in conjunction with accompanying drawing and through embodiment the present invention is described further.
Referring to Fig. 1, technical process of the present invention is following:
A, with aniline, propyl carbinol and catalyzer by weight being 1: (0.8～1.1): (0.4～0.85) adds in the reaction unit and carries out condensation reaction; Setting-up point is 220～240 ℃; Condensation reaction pressure 2.0～5.0 MPa, condensation reaction time are 6～24 hours; In the reaction process, reaction unit is controlled reflux ratio 0.5～2.0 simultaneously through reducing valve and will be reacted the water that generates and slip out through rectifying tower, and aniline and product are got back in the still, open heating system and guarantee stablizing of temperature of reaction system; Catalyzer is a Lewis acid, has improved speed of response more;
Product after b, reaction are accomplished, i.e. reaction solution oily water separation after hydrolysis, the simple layering of reaction solution is water and catalyzer in the lower floor, can directly apply mechanically to be used for synthesizing next time, the upper strata is the synthetics that the reaction back generates, and is the product bullion;
C, product bullion obtain n-butyl aniline through rectification under vacuum again, and can in rectifying, reclaim residue aniline; Surplus article after a rectifying is accomplished can repeat distillation, promptly before heat up in a steamer and repeat distillation.
Embodiment 1:
A, aniline, propyl carbinol and catalyzer are carried out condensation reaction in 1:0.8:0.4 adds reaction unit, setting-up point is 220 ℃, and condensation reaction pressure 2.0 MPa, condensation reaction time are 6 hours; In the reaction process, reaction unit is controlled reflux ratio 0.5～2.0 simultaneously through reducing valve and will be reacted the water that generates and slip out through rectifying tower, and aniline and product are got back in the still, open heating system and guarantee stablizing of temperature of reaction system; Catalyzer is a Lewis acid;
Product after b, reaction are accomplished, i.e. reaction solution oily water separation after hydrolysis, the simple layering of reaction solution is water and catalyzer in the lower floor, can directly apply mechanically to be used for synthesizing next time, the upper strata is the synthetics that the reaction back generates, and is the product bullion;
C, product bullion obtain n-butyl aniline through rectification under vacuum again, and can in rectifying, reclaim residue aniline; Surplus article after a rectifying is accomplished can repeat distillation, promptly before heat up in a steamer and repeat distillation.
Embodiment 2:
A, aniline, propyl carbinol and catalyzer are carried out condensation reaction in 1:1.1:0.85 adds reaction unit, setting-up point is 240 ℃, and condensation reaction pressure 5.0 MPa, condensation reaction time are 24 hours; In the reaction process, reaction unit is controlled reflux ratio 0.5～2.0 simultaneously through reducing valve and will be reacted the water that generates and slip out through rectifying tower, and aniline and product are got back in the still, open heating system and guarantee stablizing of temperature of reaction system; Catalyzer is a Lewis acid;
Product after b, reaction are accomplished, i.e. reaction solution oily water separation after hydrolysis, the simple layering of reaction solution is water and catalyzer in the lower floor, can directly apply mechanically to be used for synthesizing next time, the upper strata is the synthetics that the reaction back generates, and is the product bullion;
C, product bullion obtain n-butyl aniline through rectification under vacuum again, and can in rectifying, reclaim residue aniline; Surplus article after a rectifying is accomplished can repeat distillation, promptly before heat up in a steamer and repeat distillation.
Embodiment 3:
A, aniline, propyl carbinol and catalyzer are carried out condensation reaction in 1:0.95:0.8 adds reaction unit, setting-up point is 230 ℃, and condensation reaction pressure 3.0 MPa, condensation reaction time are 12 hours; In the reaction process, reaction unit is controlled reflux ratio 0.5～2.0 simultaneously through reducing valve and will be reacted the water that generates and slip out through rectifying tower, and aniline and product are got back in the still, open heating system and guarantee stablizing of temperature of reaction system; Catalyzer is a Lewis acid;
Product after b, reaction are accomplished, i.e. reaction solution oily water separation after hydrolysis, the simple layering of reaction solution is water and catalyzer in the lower floor, can directly apply mechanically to be used for synthesizing next time, the upper strata is the synthetics that the reaction back generates, and is the product bullion;
C, product bullion obtain n-butyl aniline through rectification under vacuum again, and can in rectifying, reclaim residue aniline; Surplus article after a rectifying is accomplished can repeat distillation, promptly before heat up in a steamer and repeat distillation.
Claims (5)
1. the compound method to n-butyl aniline comprises the steps: a, aniline, butanols and catalyzer is added in the reaction unit carry out condensation reaction; Product after b, reaction are accomplished carries out oily water separation after hydrolysis, obtain the product bullion; C, the product bullion is obtained n-butyl aniline through rectification under vacuum; It is characterized in that:
Among the step a, add aniline, propyl carbinol and catalyzer in the reactor drum by weight being 1: (0.8～1.1): (0.4～0.85), setting-up point are 220～240 ℃, and condensation reaction pressure 2.0～5.0 MPa, condensation reaction time are 6～24 hours; In the reaction process, reaction unit will react the water that generates and discharge reaction system.
2. the compound method to n-butyl aniline according to claim 1; It is characterized in that: among the step a, aniline, butanols and catalyzer in the adding reactor drum are by weight being 1:0.8:0.4, and setting-up point is 220 ℃; Condensation reaction pressure 2.0 MPa, condensation reaction time are 24 hours.
3. the compound method to n-butyl aniline according to claim 1; It is characterized in that: among the step a; Aniline, butanols and catalyzer in the adding reactor drum are by weight being 1:1.1:0.85; Setting-up point is 240 ℃, and condensation reaction pressure 5.0 MPa, condensation reaction time are 6 hours.
4. the compound method to n-butyl aniline according to claim 1; It is characterized in that: among the step a; Aniline, butanols and catalyzer in the adding reactor drum are by weight being 1:0.95:0.8; Setting-up point is 230 ℃, and condensation reaction pressure 3.0 MPa, condensation reaction time are 12 hours.
5. according to the described compound method to n-butyl aniline of the arbitrary claim of claim 1～4, it is characterized in that: described catalyzer is a Lewis acid.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110372520A (en) * | 2019-07-18 | 2019-10-25 | 浙江工业大学 | A kind of process for catalytic synthesis of pair of n-butyl aniline |
Citations (4)
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|---|---|---|---|---|
| EP0375333A2 (en) * | 1988-12-19 | 1990-06-27 | The Dow Chemical Company | Method for the reductive methylation of primary amines |
| EP0713858A1 (en) * | 1994-11-22 | 1996-05-29 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Improved process for the preparation of propargyl ammonium-chloride derivatives |
| CN1141912A (en) * | 1996-05-09 | 1997-02-05 | 河南省科学院化学研究所 | Preparation aromatic amine compound |
| CN1264362A (en) * | 1997-06-16 | 2000-08-23 | 梅瑞尔公司 | Method for preparing 4-(alkyl)-3-alkoxy-aniline compounds |
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- 2012-08-27 CN CN2012103051932A patent/CN102816074A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0375333A2 (en) * | 1988-12-19 | 1990-06-27 | The Dow Chemical Company | Method for the reductive methylation of primary amines |
| EP0713858A1 (en) * | 1994-11-22 | 1996-05-29 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Improved process for the preparation of propargyl ammonium-chloride derivatives |
| CN1141912A (en) * | 1996-05-09 | 1997-02-05 | 河南省科学院化学研究所 | Preparation aromatic amine compound |
| CN1264362A (en) * | 1997-06-16 | 2000-08-23 | 梅瑞尔公司 | Method for preparing 4-(alkyl)-3-alkoxy-aniline compounds |
Non-Patent Citations (1)
| Title |
|---|
| 马琳: "对-正丁基苯胺合成工艺的研究", 《中国优秀硕士学位论文全文数据库工程科技I辑》, no. 10, 8 October 2008 (2008-10-08) * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110372520A (en) * | 2019-07-18 | 2019-10-25 | 浙江工业大学 | A kind of process for catalytic synthesis of pair of n-butyl aniline |
| CN110372520B (en) * | 2019-07-18 | 2022-07-26 | 浙江工业大学 | Catalytic synthesis method of p-n-butylaniline |
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