CN110467541A - A method of m-chlorobenzene nitrile is directly synthesized by m-chlorobenzoic acid and urea - Google Patents
A method of m-chlorobenzene nitrile is directly synthesized by m-chlorobenzoic acid and urea Download PDFInfo
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- CN110467541A CN110467541A CN201910819792.8A CN201910819792A CN110467541A CN 110467541 A CN110467541 A CN 110467541A CN 201910819792 A CN201910819792 A CN 201910819792A CN 110467541 A CN110467541 A CN 110467541A
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- nitrile
- chlorobenzene
- chlorobenzoic acid
- chlorobenzamide
- chlorobenzene nitrile
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Abstract
The present invention provides a kind of method for directly synthesizing m-chlorobenzene nitrile by m-chlorobenzoic acid and urea, belongs to technical field of organic chemistry, also belongs to organic fine chemicals technical field.The method of the synthesis m-chlorobenzene nitrile are as follows: m-chlorobenzoic acid and urea reaction generate contain between chlorobenzamide intermediate reaction mixture, the intermediate reaction mixture dehydration containing chlorobenzamide generates the mixture containing m-chlorobenzene nitrile；Mixture containing m-chlorobenzene nitrile is evaporated under reduced pressure out thick nitrile, thick nitrile is evaporated under reduced pressure to finished product m-chlorobenzene nitrile through washing, filtering, drying again.The synthetic method route is short, and easy to operate, easy control of reaction conditions, production cost is low, and environmental pollution is small, and the m-chlorobenzene nitrile quality synthesized is stablized.The intermediate reaction mixture of chlorobenzamide between containing is dehydrated using ultrasonic wave or microwave catalysis wherein, can significantly improve the yield and purity of m-chlorobenzene nitrile.
Description
Technical field
The invention belongs to technical field of organic chemistry, also belong to organic fine chemicals technical field, and in particular to a kind of
The method that m-chlorobenzene nitrile is directly synthesized by m-chlorobenzoic acid and urea.
Background technique
M-chlorobenzene nitrile also known as hydroxy pyrimidine, 3- chlorobenzonitrile are important fine chemicals and organic prepare intermediate.
Due to the chemical activity of the aromatic nitriles cyano of m-chlorobenzene nitrile, by hydrolyzing plus the reaction such as hydrogen, addition or polycondensation, one can be synthesized
Serial fine chemical product is to manufacture the important source material of pesticide, medicine, dyestuff, fragrance, resin etc., such as can be used between synthesis
Chlorobenzylamine, Bupropion.
At present there are mainly two types of the preparation methods of m-chlorobenzene nitrile, a kind of method is closed using m chlorobenzaldehyde and hydroxylamine hydrochloride
At m chlorobenzaldehyde oxime, m chlorobenzaldehyde oxime dehydration prepares m-chlorobenzene nitrile.This preparation method there are conversion ratios low, cost of material
High, the technical issues of toxicity is big, three-waste pollution is serious, high production cost；Another method is to pass through ammoxidation using m-chlorotoluene
It prepares m-chlorobenzene nitrile (ammonia oxidation prepares m-chlorobenzene nitrile), m-chlorotoluene, ammonia, air carry out gas-solid phase in the catalyst bed of material
Catalysis reaction controls reaction temperature at 430~450 DEG C, leads to cooling water by the straight trip pipe in fluidized bed and remove reaction heat.Fluidized bed
Gaseous product after reaction, the external cyclone water-separator through bed top are cooled to 160 by fractional distilling tube after recycling catalyst
DEG C or so, material is received into receiving magazine.When this use m-chlorotoluene prepares m-chlorobenzene nitrile by ammoxidation, it may occur however that deep
The side reactions such as degree oxidation, and it is high to catalyst and equipment requirement, investment is big, reaction temperature is high (300~500 DEG C), operation requires
It is high.
Summary of the invention
In view of the deficiency of the prior art, it is straight by m-chlorobenzoic acid and urea that the purpose of the present invention is to provide one kind
The method for being bonded into m-chlorobenzene nitrile, the synthetic method route is short, and easy to operate, easy control of reaction conditions, production cost is low, warp
Ji remarkable benefit, environmental pollution is small, and the m-chlorobenzene nitrile quality of synthesis is stablized.
To achieve the above object, the present invention is directly synthesized used by the method for m-chlorobenzene nitrile by m-chlorobenzoic acid and urea
Technical solution is: m-chlorobenzoic acid and urea reaction generate contain between chlorobenzamide intermediate reaction mixture, contain m-chloro
The intermediate reaction mixture dehydration of benzamide generates the mixture containing m-chlorobenzene nitrile；By the mixing containing m-chlorobenzene nitrile
Object is evaporated under reduced pressure out thick nitrile, and thick nitrile is evaporated under reduced pressure to finished product m-chlorobenzene nitrile through washing, filtering, drying again.
Preferably, the molar ratio of the m-chlorobenzoic acid and urea is 1:0.5~2.
Preferably, the molar ratio of the m-chlorobenzoic acid and urea is 1:1.1~1.5.
Preferably, the intermediate reaction mixture of chlorobenzamide between the m-chlorobenzoic acid and urea reaction generation contain
Reaction temperature is 140~180 DEG C, 1~4h of reaction time；The intermediate reaction mixture dehydration containing chlorobenzamide is anti-
The reaction temperature that the mixture containing m-chlorobenzene nitrile should be generated is 140~180 DEG C, 1~4h of reaction time.With m-chlorobenzoic acid and
Urea is that raw material directly synthesize m-chlorobenzene nitrile, and entire reaction process carries out stage by stage, i.e. m-chlorobenzoic acid and urea is 140
The intermediate reaction mixture of chlorobenzamide, following intermediate reaction mixture exist between reaction generation contains at a temperature of 180 DEG C
Dehydration generates the mixture containing m-chlorobenzene nitrile at a temperature of 230 280 DEG C.It can be seen from the experiment that if m-chlorobenzoic acid with
The reaction temperature of urea early period is controlled at 140 180 DEG C, reacts 1~4h, and the intermediate reaction for generating chlorobenzamide between containing is mixed
Object is closed, is then slowly heated up, temperature generates the mixture containing m-chlorobenzene nitrile, in this way in 230 280 DEG C of 1~4h of dehydration
Reaction controlling is carried out, yield is higher.
Preferably, it is described contain between chlorobenzamide intermediate reaction mixture dehydration generate containing m-chlorobenzene nitrile
The reaction temperature of mixture is 230~280 DEG C.
Preferably, it is described contain between chlorobenzamide intermediate reaction mixture dehydration generate containing m-chlorobenzene nitrile
It is dehydrated during mixture using Catalyzed by Ultrasonic Wave, the frequency of the Catalyzed by Ultrasonic Wave is 15~40KHz.Since organic matter exists
There is the side reaction of decomposition to be inclined under high temperature, after yield peaks, the reaction time increases instead because of product high temperature point
It solves and can continue to reduce yield with reaction time increase.Thus by reaction mass (chlorobenzamide) apply ultrasonic wave or
Person's microwave radiation carries out catalytic dehydration, can accelerate dehydration speed, reduces the resolving time of dehydration time and product,
And then improve yield.
Preferably, the frequency of the Catalyzed by Ultrasonic Wave is 20KHz.Under the frequency, the dehydration of chlorobenzamide
It is fastest, yield highest.
Preferably, it is described contain between chlorobenzamide intermediate reaction mixture dehydration generate containing m-chlorobenzene nitrile
It is dehydrated during mixture using microwave catalysis, the frequency of the microwave catalysis is 1~5GHz.The chlorobenzoyl between containing
It is dehydrated during the intermediate reaction mixture dehydration of amine using microwave catalysis, dehydration speed can be accelerated, reduced anti-
Between seasonable, the reason of improving yield, improving yield same ultrasonic wave.
Preferably, the frequency of the microwave catalysis is 2.45GHz.Under the frequency, the dehydration of chlorobenzamide
It is fastest, yield highest.
Beneficial effects of the present invention: using m-chlorobenzoic acid and urea as raw material, contained by m-chlorobenzoic acid and urea generation
There is the intermediate reaction mixture of a chlorobenzamide, the intermediate reaction mixture dehydration generation containing chlorobenzamide contains
There is the mixture of m-chlorobenzene nitrile, the mixture containing m-chlorobenzene nitrile handles to obtain finished product m-chlorobenzene nitrile, the party by physical method
The cost that method synthesizes m-chlorobenzene nitrile is low, simple process, and entire reaction can react synthesis can be continuous, controllable, between synthesis
6-chlorophenyl nitrile quality is stablized.
Using m-chlorobenzoic acid and urea as Material synthesis m-chlorobenzene nitrile, in entire reaction process, distillation and evaporation are got on
A small amount of raw material m-chlorobenzoic acid, intermediate product m-chlorobenzoic acid ammonium and chlorobenzamide thick nitrile separation after enter water phase,
By distillation and concentration, intermediate product can be recycled, and re-start reaction, and the raw material and intermediate product of recycling can be thrown again
Material recycles, and greatly reduces production cost.
In addition, the exhaust gas generated in entire reaction process is mainly ammonia and carbon dioxide, ammonia and carbon dioxide are logical
It crosses water and absorbs generation ammonium bicarbonate aqueous solution, with less exhaust gas discharge capacity, realize cleaning, environmental protection production；Meanwhile ammonium hydrogen carbonate water
Solution can be used as agriculture nitrogen fertilizer, realize waste utilization, save production cost.
Specific embodiment
Embodiment 1
First into the 10L ultrasonic constant-temperature kettle equipped with thermometer probe, supersonic generator probe and distillation column, it is added
The m-chlorobenzoic acid that 3000g content is 98.0%, the urea that 1370g total nitrogenous (N) amount is 46.3%, opens heating power supply heating,
When temperature rises to 145 DEG C of partial meltings, opening stirring, early period, reaction controlling reacted 3h at 140 180 DEG C, and generation contains m-chloro
The intermediate reaction mixture of benzamide.The molar ratio of m-chlorobenzoic acid and urea is 1:1.2.Pass through high performance liquid chromatography
The content for detecting chlorobenzamide among intermediate reaction mixture is 88.9%.The ammonia and carbon dioxide escaped in reaction process,
It is absorbed by water and generates ammonium bicarbonate aqueous solution.
Then it slowly heats up, keeps material constant in 230 250 DEG C of reaction 2h with constant temperature system, next proceed to heat up, temperature
Degree control reacts 2h at 250 270 DEG C, generates the mixture containing m-chlorobenzene nitrile；By the mixture decompression containing m-chlorobenzene nitrile
Thick nitrile is distilled out, distillation test residue contains the intermediate product (m-chlorobenzoic acid ammonium and chlorobenzamide) that reaction generates, stays
When feeding intake next time, the reaction was continued in ultrasonic constant-temperature kettle.Thick nitrile is evaporated under reduced pressure to finished product m-chloro through washing, filtering, drying again
Cyanophenyl.It is 96.4% by the content that high performance liquid chromatography detects finished product m-chlorobenzene nitrile.Calculated yield, in terms of m-chlorobenzoic acid,
The yield of finished product m-chlorobenzene nitrile is 59.7%.
Contain available raw material m-chlorobenzoic acid, intermediate product m-chlorobenzoic acid ammonium in the waste water that thick nitrile is generated through washing
Moisture is steamed by way of distillation and concentration with a chlorobenzamide, intermediate product is recycled, after dry, in lower secondary response
As part material investment reaction kettle, the reaction was continued.
Embodiment 2
First into the 10L ultrasonic constant-temperature kettle equipped with thermometer probe, supersonic generator probe and distillation column, it is added
The m-chlorobenzoic acid that 3000g content is 98.0% is added the urea that 1370g total nitrogenous (N) amount is 46.3%, opens heating power supply liter
Temperature, when temperature rises to 145 DEG C of partial meltings, opening stirring, reaction temperature early period is controlled at 140 180 DEG C, is reacted 3h, is generated
Intermediate reaction mixture containing chlorobenzamide.The molar ratio of m-chlorobenzoic acid and urea is 1:1.2.Pass through efficient liquid
Phase chromatography detects chlorobenzoyl amine content 88.3% among intermediate reaction mixture.The ammonia and dioxy escaped in reaction process
Change carbon, is absorbed by water and generate ammonium bicarbonate aqueous solution.
Then it slowly heats up, while opening supersonic generator, control ultrasonic frequency 20KHz, energy-gathered ultrasonic becomes
Width bar is directly immersed in autoclave body reaction liquid, and a large amount of energy is delivered directly in reaction medium, effectively converts electric energy
For it is ultrasonic can, and be controlled by generator change amplitude the size of ultrasonic energy, keep material constant with constant temperature system
It in 230 250 DEG C of reaction 2h, next proceeds to heat up, controls 250 270 DEG C of temperature, react 2h, generation contains m-chlorobenzene nitrile
Mixture, close supersonic generator.Mixture containing m-chlorobenzene nitrile is evaporated under reduced pressure out thick nitrile, distillation test residue contains
The intermediate product (m-chlorobenzoic acid ammonium and chlorobenzamide) for having reaction to generate, stays in ultrasonic constant-temperature kettle and feeds intake in next time
When the reaction was continued.Thick nitrile is evaporated under reduced pressure to finished product through washing, filtering, drying again.Finishing room is detected by high performance liquid chromatography
The content of 6-chlorophenyl nitrile is 97.0%.Calculated yield, in terms of m-chlorobenzoic acid, the yield 92.5% of finished product m-chlorobenzene nitrile
In the waste water that thick nitrile is generated through washing containing available raw material m-chlorobenzoic acid, intermediate product m-chlorobenzoic acid ammonium and
Chlorobenzamide steams moisture by way of distillation and concentration, recycles intermediate product, after dry, the conduct in lower secondary response
Part material puts into reaction kettle, and the reaction was continued.
Embodiment 3
First into the 1L microwave constent temperature kettle equipped with thermometer and distillation column, it is chlorobenzene first between 98.0% that 300g content, which is added,
Acid, the urea of 148g total nitrogenous (N) amount 46.3%, opens heating power supply heating, when temperature rises to 145 DEG C of partial meltings, opening is stirred
It mixes, early period, reaction controlling reacted 4h at 140 180 DEG C, generated the intermediate reaction mixture of chlorobenzamide between containing.M-chloro
The molar ratio of benzoic acid and urea is 1:1.3.Chlorobenzoyl amine content among reactant is detected by high performance liquid chromatography
89.1%.The ammonia and carbon dioxide escaped in reaction process is absorbed by water and generates ammonium bicarbonate aqueous solution.
Then it slowly heats up, keeps material constant in 230 250 DEG C of reaction 2h with constant temperature system, next proceed to heat up, temperature
Degree control reacts 2h at 250 270 DEG C, generates the mixture containing m-chlorobenzene nitrile.By the mixture decompression containing m-chlorobenzene nitrile
Thick nitrile is distilled out, distillation test residue contains the intermediate product (m-chlorobenzoic acid ammonium and chlorobenzamide) that reaction generates, stays
When feeding intake next time, the reaction was continued in microwave constent temperature kettle.Thick nitrile is evaporated under reduced pressure to finished product through washing, filtering, drying again.Pass through
The content that high performance liquid chromatography detects finished product m-chlorobenzene nitrile is 96.8%.Calculated yield, in terms of m-chlorobenzoic acid, finished product m-chloro
The yield 62.4% of cyanophenyl.
Contain available raw material m-chlorobenzoic acid, intermediate product m-chlorobenzoic acid ammonium in the waste water that thick nitrile is generated through washing
Moisture is steamed by way of distillation and concentration with a chlorobenzamide, intermediate product is recycled, after dry, in lower secondary response
As part material investment reaction kettle, the reaction was continued.
Embodiment 4
First into the 1L microwave constent temperature kettle equipped with thermometer and distillation column, it is chlorobenzene first between 98.0% that 300g content, which is added,
Acid, the urea that 148g total nitrogenous (N) amount is 46.3%, opens heating power supply heating, when temperature rises to 145 DEG C of partial meltings, opens
Stirring,
Reaction temperature early period is controlled at 140 180 DEG C, reacts 4h, generates the intermediate reaction mixture of chlorobenzamide between containing.
The molar ratio of m-chlorobenzoic acid and urea is 1:1.3.Chlorobenzamide among reactant is detected by high performance liquid chromatography to contain
Amount 89.1%.The ammonia and carbon dioxide escaped in reaction process is absorbed by water and generates ammonium bicarbonate aqueous solution.
Then it slowly heats up, while opening microwave generator, control microwave frequency 2.45GHz, adjust microwave output power,
Keep material constant in 230 250 DEG C of reaction 2h with constant temperature system, next proceed to heat up, controls 250 270 DEG C of temperature, reaction
2h generates the mixture containing m-chlorobenzene nitrile, closes microwave generator.Mixture containing m-chlorobenzene nitrile is evaporated under reduced pressure out slightly
Nitrile, distillation test residue contain the intermediate product (m-chlorobenzoic acid ammonium and chlorobenzamide) that reaction generates, and stay in microwave perseverance
When feeding intake next time, the reaction was continued in warm kettle.Thick nitrile is evaporated under reduced pressure to finished product through washing, filtering, drying again.Pass through efficient liquid phase
The content that chromatography detects finished product m-chlorobenzene nitrile is 97.3%.Calculated yield, in terms of m-chlorobenzoic acid, the receipts of finished product m-chlorobenzene nitrile
Rate 92.1%.
Contain available raw material m-chlorobenzoic acid, intermediate product m-chlorobenzoic acid ammonium in the waste water that thick nitrile is generated through washing
Moisture is steamed by way of distillation and concentration with a chlorobenzamide, intermediate product is recycled, after dry, in lower secondary response
As part material investment reaction kettle, the reaction was continued.
Comparative example 14 is it is found that using m-chlorobenzoic acid and urea as Material synthesis m-chlorobenzene nitrile, m-chlorobenzoic acid and urea
The intermediate reaction mixture of chlorobenzamide, mixes the intermediate reaction of chlorobenzamide between containing between reaction generation generation contains
Object carries out catalytic dehydration using ultrasonic wave or microwave, can significantly improve the yield and purity of m-chlorobenzene nitrile, m-chlorobenzene nitrile
Yield is up to 92%, and purity is up to 97%.In addition, to unreacted raw material (m-chlorobenzoic acid) and centre in entire reaction process
Product (m-chlorobenzoic acid ammonium and chlorobenzamide) is recycled, and not only reduces the discharge capacity of the three wastes, realize safety,
Cleaning, environmental protection production, and production cost can be significantly reduced.
The present invention is not limited in the above-mentioned embodiment enumerated, and can also have other embodiment, other embodiments side
Formula is as follows.
In other embodiments, the molar ratio of the m-chlorobenzoic acid and urea can also for except 1:1,1:1.2,1:1.3,
Any one ratio in the range of 1:0.5~2 outside 1:1.4.
In other embodiments, in the dehydration, the frequency of ultrasonic wave also can be controlled in addition to 20KHz 15
Any one frequency values within the scope of~40KHz.
In other embodiments, in the dehydration, the frequency of microwave also can be controlled in place 2.45KHz outside 1
Any one frequency values within the scope of~5GHz.
In other embodiments, the m-chlorobenzoic acid and urea reaction system reaction time early period can also be 1h or 2h
(reaction temperature early period is 140 180 DEG C) can also be not integral point time, such as 1.5 h, 2.8 h, 3.2 h etc.；The m-chloro
Benzoic acid and urea reaction system late phase reaction time are (when the dehydration of the intermediate reaction mixture containing chlorobenzamide
Between) it can also be 1 h, 2h, 3h, it can also be not integral point time, such as 1.2 h, 2.8 h, 3.6 h etc..
In other embodiments, the m-chlorobenzoic acid and urea reaction system reaction temperature early period (m-chlorobenzoic acid
And urea reaction generates the reaction temperature of the intermediate reaction mixture of chlorobenzamide between containing) it is also greater than 180 DEG C, between described
Chlorobenzoic acid and the urea reaction system late phase reaction temperature (dehydration of the intermediate reaction mixture containing chlorobenzamide
Temperature) reaction temperature can also for 180 250 DEG C, 270 280 DEG C or be greater than 280 DEG C.
Claims (9)
1. a kind of method for directly synthesizing m-chlorobenzene nitrile by m-chlorobenzoic acid and urea, it is characterised in that: m-chlorobenzoic acid and urine
The intermediate reaction mixture of chlorobenzamide, the intermediate reaction mixture containing chlorobenzamide are de- between element reaction generation contains
Water reaction generates the mixture containing m-chlorobenzene nitrile；Mixture containing m-chlorobenzene nitrile is evaporated under reduced pressure out thick nitrile, thick nitrile is through water
It washes, filter, drying and be evaporated under reduced pressure to finished product m-chlorobenzene nitrile again.
2. the method for synthesis m-chlorobenzene nitrile according to claim 1, it is characterised in that: the m-chlorobenzoic acid and urea
Molar ratio is 1:0.5~2.
3. the method for synthesis m-chlorobenzene nitrile according to claim 2, it is characterised in that: the m-chlorobenzoic acid and urea
Molar ratio is 1:1.1~1.5.
4. the method for synthesis m-chlorobenzene nitrile according to claim 3, it is characterised in that: the m-chlorobenzoic acid and urea are anti-
The reaction temperature that the intermediate reaction mixture of the chlorobenzamide containing between should be generated is 140~180 DEG C, 1~4h of reaction time；Institute
The intermediate reaction mixture dehydration for stating the chlorobenzamide containing between generates the reaction temperature of the mixture containing m-chlorobenzene nitrile
It is 180~280 DEG C, 1~4h of reaction time.
5. the method for synthesis m-chlorobenzene nitrile according to claim 4, it is characterised in that: it is described contain between chlorobenzamide
The reaction temperature that intermediate reaction mixture dehydration generates the mixture containing m-chlorobenzene nitrile is 230~270 DEG C.
6. it is according to claim 1-5 synthesis m-chlorobenzene nitrile method, it is characterised in that: it is described contain between chlorobenzene
The intermediate reaction mixture dehydration of formamide uses Catalyzed by Ultrasonic Wave during generating the mixture containing m-chlorobenzene nitrile
Dehydration, the frequency of the Catalyzed by Ultrasonic Wave are 15~40KHz.
7. the preparation method of m-chlorobenzene nitrile according to claim 6, it is characterised in that: the frequency of the Catalyzed by Ultrasonic Wave is
20KHz。
8. it is according to claim 1-5 synthesis m-chlorobenzene nitrile method, it is characterised in that: it is described contain between chlorobenzene
The intermediate reaction mixture dehydration of formamide is taken off during generating the mixture containing m-chlorobenzene nitrile using microwave catalysis
Water, the frequency of the microwave catalysis are 1~5GHz.
9. the method for synthesis m-chlorobenzene nitrile according to claim 8, it is characterised in that: the frequency of the microwave catalysis is
2.45GHz。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB831051A (en) * | 1956-02-28 | 1960-03-23 | Heyden Newport Chemical Corp | Improvements in or relating to production of polychlorobenzene compounds |
| US5965764A (en) * | 1997-08-06 | 1999-10-12 | Toray Industries, Inc. | Process for producing a nitrile |
| US6353126B1 (en) * | 1999-06-30 | 2002-03-05 | Creanova Inc. | Process for the production of malononitrile |
-
2019
- 2019-08-31 CN CN201910819792.8A patent/CN110467541A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB831051A (en) * | 1956-02-28 | 1960-03-23 | Heyden Newport Chemical Corp | Improvements in or relating to production of polychlorobenzene compounds |
| US5965764A (en) * | 1997-08-06 | 1999-10-12 | Toray Industries, Inc. | Process for producing a nitrile |
| US6353126B1 (en) * | 1999-06-30 | 2002-03-05 | Creanova Inc. | Process for the production of malononitrile |
Non-Patent Citations (4)
| Title |
|---|
| 易兵等: "对甲苯腈合成工艺改进", 《河南化工》 * |
| 蒲帅天等: "对甲基苯甲腈合成新工艺的研究", 《广东化工》 * |
| 郑延华等: "氯代苯甲酸的氰化", 《化学世界》 * |
| 陈华等: "苯甲腈合成新方法", 《淮海工学院学报》 * |
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