CN105218401B - The method that continuity method synthesizes benzene acetonitrile - Google Patents
The method that continuity method synthesizes benzene acetonitrile Download PDFInfo
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Abstract
The invention discloses a kind of method that continuity method synthesizes benzene acetonitrile, it is related to the technical field of compound preparation that cyano group is connected hexa-atomic aromatic ring by saturated carbon chains.Comprise the following steps：The temperature of microreactor is adjusted to 80 400 DEG C, sodium cyanide solution and phase transfer catalyst mixed liquor, and benzyl chloride are continuously injected into microreactor respectively, reaction time is 20 300s in microreactor, directly obtains the aqueous solution of benzene acetonitrile.The yield of benzene acetonitrile is the method increase, the generation of side reaction is reduced, reaction can be made quickly to carry out, production efficiency is high, is greatlyd save manually, cost is low, Automated condtrol is easy to implement, and product quality is preferably, for follow-up post processing advantageously.
Description
Technical field
The present invention relates to the technical field of compound preparation that cyano group is connected hexa-atomic aromatic ring by saturated carbon chains.
Background technology
Benzene acetonitrile is a kind of very important intermediate, and downstream product phenylacetic acid is the precursor of important penicillin synthesis
Matter, it can also be used to essence and flavoring agent industry.The method for synthesizing benzene acetonitrile, usually using still reaction, batch (-type) is carried out, reaction life
Into impurity it is more, and production efficiency is relatively low, and especially benzene acetonitrile has special penetrating odor, the shortcoming of batch production
Just seem especially prominent.The patent CN201942626U for having Shandong Liaocheng ZhongShengLanRui chemical engineering Co., Ltd discloses entitled《Benzene
The apparatus and method of continuous cyanogenation in acetonitrile production》Patent, using many reactors being used in series, lead between reactor
The mode of overflow pipe connection is crossed, can be carried out continuously benzene acetonitrile production, the labor intensity of workman is substantially reduced, and crude product purity is
97.0-98.5%.Such a continuous reaction apparatus is carried out continuously cyanogenation, still, and its reaction time is still longer, used
Equipment is more, and floor space is big.
The content of the invention
, should the technical problem to be solved in the present invention is to provide a kind of method that utilization microreactor continuity method synthesizes benzene acetonitrile
Method improves the yield of benzene acetonitrile, reduces the generation of side reaction, and reaction can be made quickly to carry out, and production efficiency is high, saves significantly
About artificial, cost is low, is easy to implement Automated condtrol, and product quality is preferably, for follow-up post processing advantageously.
In order to solve the above technical problems, the technical solution used in the present invention is：A kind of continuity method synthesizes the side of benzene acetonitrile
Method, it is characterised in that comprise the following steps：Adjust microreactor temperature to 80-400 DEG C, by sodium cyanide solution with mutually turn
Shifting catalyst mixed liquor, and benzyl chloride are continuously injected into microreactor respectively, and reaction time is 20- in microreactor
300s, directly obtains the aqueous solution of benzene acetonitrile.
It is preferred that, it is further comprising the steps of：The aqueous solution of benzene acetonitrile obtained above is passed through into continuous extraction separation equipment
Benzene acetonitrile crude product is separated with waste water, benzene acetonitrile crude product is obtained.
It is preferred that, the mol ratio of Cymag and benzyl chloride is 1-1.2 in sodium cyanide solution：1.
It is preferred that, phase transfer catalyst be benzyltriethylammoinium chloride, TBAB, benzyl diethylammonium chloride or
Tetrabutylammonium chloride.
It is further preferred that the consumption of phase transfer catalyst is the 0.1-5 ‰ of benzyl chloride quality.
It is preferred that, the mass concentration of sodium cyanide solution is 5-30%.
It is further preferred that the mass concentration of sodium cyanide solution is 10-25%.
It is preferred that, the temperature of microreactor is 150-400 DEG C.
It is preferred that, the benzene acetonitrile crude product that continuous extraction separation equipment is obtained is used for rectifying, isolated waste water, into three
Useless processing system.
Suitable microreactor for the inventive method can be from the mechanism such as healthy and free from worry is obtained.
It is using the beneficial effect produced by above-mentioned technical proposal：
（1）The present invention carries out the synthetic reaction of benzene acetonitrile using microreactor, by the proportioning, the reaction that control reaction raw materials
The process conditions such as temperature, reaction time, make the raw material in microreactor react completely, react the aqueous solution of obtained benzene acetonitrile
Benzene acetonitrile crude product is separated with waste water by continuous extraction separation equipment, obtained benzene acetonitrile crude product is directly entered rectifying system
System, realizes continuous production, and production efficiency is high, greatlys save manually, cost is low, is easy to implement Automated condtrol.
（2）The present invention is reacted using microreactor, the synthetic reaction of benzene acetonitrile can be made quickly to carry out, in 20-300s
It can react complete, the reaction time significantly shortens, reduce the generation of side reaction, improve the yield of benzene acetonitrile.
（3）The present invention is reacted using microreactor, microreactor static mixing element close to the inner portion, and it is special to be formed
Flow pattern, good mixing effect.In addition, the minitype channel construction of microreactor, makes it have bigger mass transfer contact area, bigger changes
Hot specific surface area, its heat and mass efficiency high.
（4）The present invention can not only carry out cyanogenation serialization, and pass through in terms of post processing continuous extraction point
It can be also carried out continuously from equipment, reduce further artificial operation, pass through the process of the present invention, benzene acetonitrile crude product purity
More than 98.5%, its yield is more than 96%.
Brief description of the drawings
The present invention is further detailed explanation with reference to the accompanying drawings and detailed description；
Fig. 1 is the process chart of the present invention.
Embodiment
Embodiment 1
The temperature control of microreactor is adjusted first at 180 DEG C, under plunger pumping action, by 12kmol mass concentrations
13% sodium cyanide solution and phase transfer catalyst benzyl diethylammonium chloride（The consumption of phase transfer catalyst is benzyl chloride matter
The 1 ‰ of amount）Mixed liquor, and 10kmol benzyl chloride liquid are continuously injected into microreactor respectively, and the residence time controls in 150s, directly
The aqueous solution for obtaining benzene acetonitrile is connect, the quality of benzene acetonitrile, crude product purity 98.5% are monitored by GC.Obtained benzene acetonitrile it is water-soluble
Liquid is in continuous extraction separation equipment（Extract centrifuge）In the presence of, the aqueous solution of obtained benzene acetonitrile is centrifuged,
What is isolated from light phase mouth is benzene acetonitrile crude product, and benzene acetonitrile crude yield is 97.5%, from heavy phase isolate for useless sodium chloride water
Solution, obtained benzene acetonitrile crude product is directly entered distillation system, realizes continuous production.Isolated waste water, into three
Useless processing system.
Embodiment 2
The temperature control of microreactor is adjusted first at 250 DEG C, under plunger pumping action, by 12kmol 13% cyaniding
Sodium water solution and phase transfer catalyst benzyl diethylammonium chloride（The consumption of phase transfer catalyst is the 0.5 ‰ of benzyl chloride quality）
Mixed liquor, and 10kmol benzyl chloride liquid are continuously injected into microreactor, and the residence time is controlled in 100s, directly obtains benzene acetonitrile
The aqueous solution, pass through GC monitor benzene acetonitrile quality, crude product purity 98.6%.Obtained benzene acetonitrile feed liquid is separated in continuous extraction
Equipment（Extract centrifuge）In the presence of, obtained benzene acetonitrile feed liquid is centrifuged, from light phase mouth, isolate is benzene
Acetonitrile crude product, benzene acetonitrile crude yield is 97.7%, from heavy phase isolate for useless sodium-chloride water solution, obtained benzene acetonitrile is thick
Product are directly entered distillation system, realize continuous production.Isolated waste water, into three-protection design system.
Embodiment 3
The temperature control of microreactor is adjusted first at 400 DEG C, under plunger pumping action, by 12kmol 13% cyaniding
Sodium water solution and phase transfer catalyst benzyltriethylammoinium chloride（The consumption of phase transfer catalyst is the 0.8 ‰ of benzyl chloride quality）
Mixed liquor, and 10kmol benzyl chloride liquid are continuously injected into microreactor, and the residence time is controlled in 20s, directly obtains benzene acetonitrile
The aqueous solution, pass through GC monitor benzene acetonitrile quality, crude product purity 98.5%.Obtained benzene acetonitrile feed liquid is separated in continuous extraction
Equipment（Extract centrifuge）In the presence of, obtained benzene acetonitrile feed liquid is centrifuged, from light phase mouth, isolate is benzene
Acetonitrile crude product, benzene acetonitrile crude yield is 97.6%, from heavy phase isolate for useless sodium-chloride water solution, obtained benzene acetonitrile is thick
Product are directly entered distillation system, realize continuous production.
Embodiment 4
The temperature control of microreactor is adjusted first at 180 DEG C, under plunger pumping action, by 11kmol 13% cyaniding
Sodium water solution and phase transfer catalyst benzyltriethylammoinium chloride（The consumption of phase transfer catalyst is the 2 ‰ of benzyl chloride quality）It is mixed
Liquid is closed, and 10kmol benzyl chloride liquid is continuously injected into microreactor, the residence time is controlled in 70s, directly obtains benzene acetonitrile
The aqueous solution, the quality of benzene acetonitrile, crude product purity 98.6% are monitored by GC.Obtained benzene acetonitrile feed liquid is set in continuous extraction separation
It is standby（Extract centrifuge）In the presence of, obtained benzene acetonitrile feed liquid is centrifuged, from light phase mouth, isolate is benzene second
Nitrile crude product, benzene acetonitrile crude yield is 97.7%, from heavy phase isolate for useless sodium-chloride water solution, obtained benzene acetonitrile crude product
Distillation system is directly entered, continuous production is realized.
Embodiment 5
The temperature control of microreactor is adjusted first at 80 DEG C, under plunger pumping action, by 10kmol mass concentrations
10% sodium cyanide solution and phase transfer catalyst TBAB（The consumption of phase transfer catalyst is benzyl chloride quality
0.1‰）Mixed liquor, and 10kmol benzyl chloride liquid are continuously injected into microreactor, and the residence time is controlled in 300s, is directly obtained
The aqueous solution of benzene acetonitrile, the quality of benzene acetonitrile, crude product purity 98.6% are monitored by GC.The aqueous solution of obtained benzene acetonitrile is even
Continuous extraction and stripping apparatus（Extract centrifuge）In the presence of, the aqueous solution of obtained benzene acetonitrile is centrifuged, from light phase
What mouth was isolated is benzene acetonitrile crude product, and benzene acetonitrile crude yield is 97.5%, from heavy phase isolate for useless sodium-chloride water solution,
Obtained benzene acetonitrile crude product is directly entered distillation system, realizes continuous production.Isolated waste water, into three-protection design
System.
Embodiment 6
The temperature control of microreactor is adjusted first at 320 DEG C, under plunger pumping action, by 11kmol mass concentrations
25% sodium cyanide solution and phase transfer catalyst TBAB（The consumption of phase transfer catalyst is benzyl chloride quality
5‰）Mixed liquor, and 10kmol benzyl chloride liquid are continuously injected into microreactor, and the residence time is controlled in 200s, directly obtains benzene
The aqueous solution of acetonitrile, the quality of benzene acetonitrile, crude product purity 98.7% are monitored by GC.The aqueous solution of obtained benzene acetonitrile is continuous
Extraction and stripping apparatus（Extract centrifuge）In the presence of, the aqueous solution of obtained benzene acetonitrile is centrifuged, from light phase mouthful
What is isolated is benzene acetonitrile crude product, and benzene acetonitrile crude yield is 98.1%, from heavy phase isolate for useless sodium-chloride water solution, obtain
To benzene acetonitrile crude product be directly entered distillation system, realize continuous production.Isolated waste water, into three-protection design system
System.
Embodiment 7
The temperature control of microreactor is adjusted first at 150 DEG C, it is under plunger pumping action, 10.5kmol mass is dense
The sodium cyanide solution and phase transfer catalyst tetrabutylammonium chloride of degree 5%（The consumption of phase transfer catalyst is benzyl chloride quality
3.5‰）Mixed liquor, and 10kmol benzyl chloride liquid are continuously injected into microreactor, and the residence time is controlled in 250s, is directly obtained
The aqueous solution of benzene acetonitrile, the quality of benzene acetonitrile, crude product purity 98.6% are monitored by GC.The aqueous solution of obtained benzene acetonitrile is even
Continuous extraction and stripping apparatus（Extract centrifuge）In the presence of, the aqueous solution of obtained benzene acetonitrile is centrifuged, from light phase
What mouth was isolated is benzene acetonitrile crude product, and benzene acetonitrile crude yield is 98.2%, from heavy phase isolate for useless sodium-chloride water solution,
Obtained benzene acetonitrile crude product is directly entered distillation system, realizes continuous production.Isolated waste water, into three-protection design
System.
Embodiment 8
The temperature control of microreactor is adjusted first at 220 DEG C, it is under plunger pumping action, 11.5kmol mass is dense
The sodium cyanide solution and phase transfer catalyst tetrabutylammonium chloride of degree 30%（The consumption of phase transfer catalyst is benzyl chloride quality
1 ‰）Mixed liquor, and 10kmol benzyl chloride liquid are continuously injected into microreactor, and the residence time is controlled in 180s, is directly obtained
The aqueous solution of benzene acetonitrile, the quality of benzene acetonitrile, crude product purity 98.6% are monitored by GC.The aqueous solution of obtained benzene acetonitrile is even
Continuous extraction and stripping apparatus（Extract centrifuge）In the presence of, the aqueous solution of obtained benzene acetonitrile is centrifuged, from light phase
What mouth was isolated is benzene acetonitrile crude product, and benzene acetonitrile crude yield is 98.0%, from heavy phase isolate for useless sodium-chloride water solution,
Obtained benzene acetonitrile crude product is directly entered distillation system, realizes continuous production.Isolated waste water, into three-protection design
System.
The inventive method improves the yield of benzene acetonitrile, reduces the generation of side reaction, and reaction can be made quickly to carry out, production
Efficiency high, is greatlyd save manually, cost is low, is easy to implement Automated condtrol, and product quality is preferably, for follow-up rear place
Reason is advantageously.
Claims (4)
1. a kind of method that continuity method synthesizes benzene acetonitrile, it is characterised in that comprise the following steps：
The temperature of microreactor is adjusted to 150-400 DEG C, by sodium cyanide solution and phase transfer catalyst mixed liquor, and benzyl chloride
It is continuously injected into respectively in microreactor, reaction time is 20-300s in microreactor, directly obtains the water-soluble of benzene acetonitrile
Liquid；
The mol ratio of Cymag and benzyl chloride is 1-1.2 in sodium cyanide solution：1；
Phase transfer catalyst is benzyltriethylammoinium chloride, TBAB, benzyl diethylammonium chloride or tetrabutyl chlorination
Ammonium；
The consumption of phase transfer catalyst is the 0.1-5 ‰ of benzyl chloride quality；
The mass concentration of sodium cyanide solution is 5-30%.
2. the method that continuity method according to claim 1 synthesizes benzene acetonitrile, it is characterised in that further comprising the steps of：Will
The aqueous solution of benzene acetonitrile obtained above is separated benzene acetonitrile crude product with waste water by continuous extraction separation equipment, obtains benzene
Acetonitrile crude product.
3. the method that continuity method according to claim 1 synthesizes benzene acetonitrile, it is characterised in that the quality of sodium cyanide solution
Concentration is 10-25%.
4. the method that continuity method according to claim 2 synthesizes benzene acetonitrile, it is characterised in that continuous extraction separation equipment is obtained
The benzene acetonitrile crude product arrived is used for rectifying, isolated waste water, into three-protection design system.
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106083628B (en) * | 2016-06-01 | 2018-06-26 | 河北大学 | A kind of method for preparing p-chlorophenylglycine |
| CN106278861B (en) * | 2016-08-24 | 2019-05-14 | 河北诚信集团有限公司 | A method of preparing substituted phenylacetic acid |
| CN107698433A (en) * | 2017-09-12 | 2018-02-16 | 潍坊滨海石油化工有限公司 | The preparation method of phenylacetic acid |
| CN109232312A (en) * | 2018-09-30 | 2019-01-18 | 营创三征(营口)精细化工有限公司 | The method for continuously synthesizing of benzene acetonitrile |
| CN110218162A (en) * | 2019-04-04 | 2019-09-10 | 江苏万年长药业有限公司 | The continuous preparation method of one kind (R) -4- cyano-3-hydroxy ethyl butyrate |
| CN110841585A (en) * | 2019-10-14 | 2020-02-28 | 吴剑华 | Benzyl cyanide production device and use method thereof |
| CN111138316A (en) * | 2020-01-14 | 2020-05-12 | 营口德瑞化工有限公司 | Synthesis method of phenylacetonitrile |
| CN111253284B (en) * | 2020-03-11 | 2023-08-04 | 青岛雪洁助剂有限公司 | Benzyl cyanide production device and process with continuous whole process |
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