CN109651193A - A kind of synthetic method of benzoyl cyanide - Google Patents

A kind of synthetic method of benzoyl cyanide Download PDF

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Publication number
CN109651193A
CN109651193A CN201910056947.7A CN201910056947A CN109651193A CN 109651193 A CN109651193 A CN 109651193A CN 201910056947 A CN201910056947 A CN 201910056947A CN 109651193 A CN109651193 A CN 109651193A
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China
Prior art keywords
benzoyl cyanide
cyanide
benzoyl
synthetic method
chlorobenzoyl chloride
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CN201910056947.7A
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Chinese (zh)
Inventor
徐国想
徐松
李绍锁
汪港
谷训刚
李国庆
张允冰
刘学峰
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Jiangsu Jia Mai Chemical Co Ltd
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Jiangsu Jia Mai Chemical Co Ltd
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Priority to CN201910056947.7A priority Critical patent/CN109651193A/en
Publication of CN109651193A publication Critical patent/CN109651193A/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/14Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of synthetic methods of benzoyl cyanide, using Cymag and chlorobenzoyl chloride as raw material, using the mixture of Macrogol 600 and tri-n-octyl methyl ammonium chloride as phase transfer catalyst, using water or glycerol as cocatalyst, it reacts at 60 DEG C -110 DEG C with chlorobenzoyl chloride, benzoyl cyanide crude product and byproduct of reaction are made after reaction time 3-5 hour, under the action of the solvent, benzoyl cyanide fine work is made after the crude product is washed, separation.The present invention synthesizes the technique of benzoyl cyanide by simple method, in order to reduce pollution, turns harm into good, and need to be handled using alkaline chlorination process, cyanide is made by active oxychloride, destruction, to generate nontoxic sodium chloride under strongly alkaline conditions.And solvent is recyclable applies, therefore the synthetic method has the characteristics that pollute small, high conversion rate, easy to operate.

Description

A kind of synthetic method of benzoyl cyanide
Technical field
The present invention relates to field of fine chemical more particularly to a kind of synthetic methods of benzoyl cyanide.
Background technique
It is colourless squamous crystal under benzoyl cyanide room temperature, is a kind of important fine-chemical intermediate, is widely used in The synthesis of pesticide and medicine, such as: herbicide metamitron, benzene piperazine are net, medical gastrodyn etc..The synthetic method of benzoyl cyanide has: Chlorobenzoyl chloride and cuprous cyanide reaction method, chlorobenzoyl chloride and benzoyl oxide and Cymag reaction method, dimethylamine catalysis hydrogen cyanide method, Cymag and chlorobenzoyl chloride reaction method.But chlorobenzoyl chloride and reaction temperature needed for cuprous cyanide reaction method are about 210 DEG C high, are taken Between longer and yield it is low, improved method be added ultra-fine grain diameter Cymag and a certain amount of second cyanogen, cuprous cyanide can be reduced Dosage, reaction temperature is reduced, but still can not solve the problems, such as mantoquita recycling and heavy metal pollution, so its industrialized production Value is little.Chlorobenzoyl chloride and benzoyl oxide and Cymag reaction method are the problem is that benzoyl cyanide and benzoyl oxide are difficult to point From.Dimethylamine catalysis hydrogen cyanide method need to use the hydrogen cyanide of severe toxicity, and the more difficult and risk of operation is very big, and the requirement ratio to equipment It is more harsh.Cymag and when chlorobenzoyl chloride reaction method newer synthetic method its need phase transfer catalyst and a small amount of polar object Matter, the method mild condition and pollution it is small.The selection of its phase transfer catalyst is emphasis.
The type of phase transfer catalyst has very much, again includes quaternary ammonium salt, quaternary alkylphosphonium salt, sulfonium salt such as father-in-law's salt, this is a kind of Use phase transfer catalyst earlier;Polyether class comprising crown ether, polyethylene glycol and its derivative, big ring type amidogen polyether.In view of Application of the phase transfer catalyst in organic synthesis is more and more wider, and the effect of the phase transfer catalyst of unifunctional base cannot expire The existing demand of foot, therefore there are a series of multi-functional phase transfer catalysis (PTC)s being made of the phase transfer catalyst of single function base Agent, such as: polyethylene glycol, the combination of father-in-law's salt, polyethylene glycol, crown ether combination, quaternary ammonium salt, crown ether combination etc. optimize organic conjunction with this At route.
In conclusion traditional technique has the problem of heavy metal pollution, simultaneously because temperature and time demand is higher, institute It is low to cause conversion ratio, and benzoyl cyanide is difficult to separate with benzoyl oxide, and dimethylamine catalysis hydrogen cyanide method need to use severe toxicity Hydrogen cyanide, operate more difficult and risk it is very big.
Summary of the invention
The purpose of the present invention is to solve disadvantages existing in the prior art, such as: traditional technique has heavy metal-polluted The problem of dye, simultaneously because temperature and time demand is higher, so it is low to cause conversion ratio, and benzoyl cyanide and benzoyl oxide It is difficult to separate, dimethylamine catalysis hydrogen cyanide method need to use the hydrogen cyanide of severe toxicity, and it is very big to operate more difficult and risk.
To achieve the goals above, present invention employs following technical solutions:
A kind of synthetic method of benzoyl cyanide, using Cymag and chlorobenzoyl chloride as raw material, using toluene as solvent, with poly- second two Alcohol 600 and tri-n-octyl methyl ammonium chloride are mixing phase transfer catalyst, using water or glycerol as cocatalyst, at 60 DEG C -110 DEG C Chlorobenzoyl chloride is added dropwise in temperature range, after chlorobenzoyl chloride is added dropwise, heat preservation reflux, and tracking reaction process is composed with gas, to It can stop flowing back when the mass fraction of chlorobenzoyl chloride is less than 0.1% in reaction solution, benzoyl cyanide crude product is obtained by filtration simultaneously in about 4h Filter residue is washed with toluene, merging filtrate simultaneously isolates solvent and benzoyl cyanide, and solvent is recyclable to be applied, the matter of gained benzoyl cyanide Measuring score is 99%, yield 96%-97%.
Further, phase transfer catalyst used in the synthesis process of benzoyl cyanide is the catalysis of different single function bases The novel and multifunctional base phase transfer catalyst of agent composition, the i.e. combination of polyethylene glycol and father-in-law's salt.It is preferred that Macrogol 600 is pungent with three The mixture of methyl ammonium, Macrogol 600 dosage are the 0.1%-0.5% of chlorobenzoyl chloride quality, and Macrogol 600 Mass ratio with tri-n-octyl methyl ammonium chloride is 1:1.
Further, using toluene as solvent in the synthesis process of benzoyl cyanide, using water or glycerol as cocatalyst.Benzoyl The dropping temperature of chlorine is 60 DEG C -110 DEG C.
Compared with prior art, the beneficial effects of the present invention are: the present invention synthesizes benzoyl cyanide by simple method Technique is turned harm into good to reduce pollution, need to be handled using alkaline chlorination process, make cyanide under strongly alkaline conditions by Active oxychloride, destruction generate nontoxic sodium chloride.And solvent is recycled and applies, therefore the synthetic method is small with pollution, turns The features such as rate is high, easy to operate.
Detailed description of the invention
Fig. 1 is a kind of synthetic method response diagram of benzoyl cyanide proposed by the present invention.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.
In the description of the present invention, it is to be understood that, term " on ", "lower", "front", "rear", "left", "right", "top", The orientation or positional relationship of the instructions such as "bottom", "inner", "outside" is to be based on the orientation or positional relationship shown in the drawings, merely to just In description the present invention and simplify description, rather than the device or element of indication or suggestion meaning must have a particular orientation, with Specific orientation construction and operation, therefore be not considered as limiting the invention.
The synthetic method of one benzoyl cyanide of embodiment
By 100mL toluene, the solid sodium cyanide of 23.7g 97%, 0.06g Macrogol 600,0.06g tricaprylmethyl chlorine Change ammonium, 0.1g water is put into 250mL four-hole boiling flask, unlatching device for absorbing tail gas, stirring, recirculated cooling water.Heating device is opened, It begins to warm up.When the temperature of reaction solution rises to 60 DEG C, the cock of constant pressure funnel is opened, starts that 57.4g benzoyl is added dropwise Chlorine pays attention to maintaining reaction temperature between 60 DEG C to 85 DEG C.Chlorobenzoyl chloride about 1.5h is dripped off, and after being added dropwise, it is anti-to continue reflux Tracking reaction process should and be sampled, when the mass fraction of chlorobenzoyl chloride in reaction solution is less than 0.1%, reaction terminates, and about needs 4h. After being cooled to 35 DEG C -45 DEG C, filtering, filter residue is washed in two times with 40mL toluene, collects filtrate.51.4g matter is obtained after handling filtrate Measure the benzoyl cyanide that score is 99%, yield 96.1%.The solvent toluene isolated is recyclable to be applied.
The cyanide (predominantly Cymag) that byproduct sodium chloride contains is handled with alkaline chlorination process, makes cyanide strong By active oxychloride, destruction under alkaline condition, nontoxic available sodium chloride is generated.
The synthetic method of embodiment dibenzoyl cyanogen
By 100mL toluene, the solid sodium cyanide of 23.7g 97%, 0.3g Macrogol 600,0.3g tricaprylmethyl chlorination In ammonium, 0.6g water investment 250mL four-hole boiling flask, device for absorbing tail gas, stirring, recirculated cooling water are opened.Heating device is opened, is opened Begin to heat.When the temperature of reaction solution rises to 60 DEG C, the cock of constant pressure funnel is opened, starts that 57.4g chlorobenzoyl chloride is added dropwise, Pay attention to maintaining reaction temperature between 60 DEG C to 85 DEG C.Chlorobenzoyl chloride about 1.5h is dripped off, and after being added dropwise, continues back flow reaction simultaneously Sampling tracking reaction process, when the mass fraction of chlorobenzoyl chloride in reaction solution is less than 0.1%, reaction terminates, and about needs 4h.Cooling To after 35 DEG C -45 DEG C, filtering, filter residue is washed in two times with 40mL toluene, collects filtrate.51.8g mass point is obtained after handling filtrate The benzoyl cyanide that number is 99%, yield 96.9%.The solvent toluene isolated is recyclable to be applied.
The cyanide (predominantly Cymag) that byproduct sodium chloride contains is handled with alkaline chlorination process, makes cyanide strong By active oxychloride, destruction under alkaline condition, nontoxic available sodium chloride is generated.
The synthetic method of embodiment dibenzoyl cyanogen
By 100mL toluene, the solid sodium cyanide of 23.7g 97%, 0.06g Macrogol 600,0.06g tricaprylmethyl chlorine Change ammonium, 0.1g water is put into 250mL four-hole boiling flask, unlatching device for absorbing tail gas, stirring, recirculated cooling water.Heating device is opened, It begins to warm up.When the temperature of reaction solution rises to 85 DEG C, the cock of constant pressure funnel is opened, starts that 57.4g benzoyl is added dropwise Chlorine pays attention to maintaining reaction temperature between 85 DEG C to 110 DEG C.Chlorobenzoyl chloride about 1.5h is dripped off, and after being added dropwise, it is anti-to continue reflux Tracking reaction process should and be sampled, when the mass fraction of chlorobenzoyl chloride in reaction solution is less than 0.1%, reaction terminates, and about needs 4h. After being cooled to 35 DEG C -45 DEG C, filtering, filter residue is washed in two times with 40mL toluene, collects filtrate.51.7g matter is obtained after handling filtrate Measure the benzoyl cyanide that score is 99%, yield 96.7%.The solvent toluene isolated is recyclable to be applied.
The cyanide (predominantly Cymag) that byproduct sodium chloride contains is handled with alkaline chlorination process, makes cyanide strong By active oxychloride, destruction under alkaline condition, nontoxic available sodium chloride is generated.
The synthetic method of example IV benzoyl cyanide
By 100mL toluene, the solid sodium cyanide of 23.7g 97%, 0.3g Macrogol 600,0.3g tricaprylmethyl chlorination In ammonium, 0.6g water investment 250mL four-hole boiling flask, device for absorbing tail gas, stirring, recirculated cooling water are opened.Heating device is opened, is opened Begin to heat.When the temperature of reaction solution rises to 85 DEG C, the cock of constant pressure funnel is opened, starts that 57.4g chlorobenzoyl chloride is added dropwise, Pay attention to maintaining reaction temperature between 85 DEG C to 110 DEG C.Chlorobenzoyl chloride about 1.5h is dripped off, and after being added dropwise, continues back flow reaction And tracking reaction process is sampled, when the mass fraction of chlorobenzoyl chloride in reaction solution is less than 0.1%, reaction terminates, and about needs 4h.Drop To after 35 DEG C -45 DEG C, filtering, filter residue is washed temperature in two times with 40mL toluene, collects filtrate.51.5g mass is obtained after handling filtrate The benzoyl cyanide that score is 99%, yield 96.3%.The solvent toluene isolated is recyclable to be applied.
The cyanide (predominantly Cymag) that byproduct sodium chloride contains is handled with alkaline chlorination process, makes cyanide strong By active oxychloride, destruction under alkaline condition, nontoxic available sodium chloride is generated.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto, Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.

Claims (6)

1. a kind of synthetic method of benzoyl cyanide, it is characterised in that step are as follows: using Cymag and chlorobenzoyl chloride as raw material, with poly- second The mixture of glycol 600 and tri-n-octyl methyl ammonium chloride is phase transfer catalyst, using water or glycerol as cocatalyst, 60 DEG C- It reacts at 110 DEG C with chlorobenzoyl chloride, benzoyl cyanide crude product and byproduct of reaction is made after reaction time 3-5 hour, Under the action of solvent, benzoyl cyanide fine work is made after the crude product is washed, separation.
2. a kind of synthetic method of benzoyl cyanide according to claim 1, which is characterized in that the solvent is toluene.
3. a kind of synthetic method of benzoyl cyanide according to claim 1, which is characterized in that the Macrogol 600 and The mass ratio of tri-n-octyl methyl ammonium chloride is 1:1.
4. a kind of synthetic method of benzoyl cyanide according to claim 1, which is characterized in that the Macrogol 600 is used Amount is the 0.1%-0.5% of chlorobenzoyl chloride quality.
5. a kind of synthetic method of benzoyl cyanide according to claim 1, which is characterized in that the cocatalyst dosage is The 0.2%-1.0% of chlorobenzoyl chloride quality.
6. a kind of synthetic method of benzoyl cyanide according to claim 1, which is characterized in that the byproduct of reaction uses Alkaline chlorination process is handled.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113880729A (en) * 2021-10-29 2022-01-04 邯郸市瑞田农药有限公司 Preparation method for synthesizing benzoyl cyanide by catalyst catalysis

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113880729A (en) * 2021-10-29 2022-01-04 邯郸市瑞田农药有限公司 Preparation method for synthesizing benzoyl cyanide by catalyst catalysis
CN113880729B (en) * 2021-10-29 2024-04-26 邯郸市瑞田农药有限公司 Preparation method for synthesizing benzoyl cyanide by catalyst catalysis

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