CN113620836A - Preparation method of acetonitrile - Google Patents
Preparation method of acetonitrile Download PDFInfo
- Publication number
- CN113620836A CN113620836A CN202110927263.7A CN202110927263A CN113620836A CN 113620836 A CN113620836 A CN 113620836A CN 202110927263 A CN202110927263 A CN 202110927263A CN 113620836 A CN113620836 A CN 113620836A
- Authority
- CN
- China
- Prior art keywords
- acetonitrile
- monoethylamine
- reaction
- hydrogen
- reactor
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8953—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of acetonitrile, which comprises the following steps: vaporizing monoethylamine and adding Cu-Zn-Pt/Al2O3Is used as a catalyst and is subjected to gas-solid reaction with hydrogen in a reactor, wherein the reaction pressure in the reactor is kept between 0.01MPa and 0.05MPa, and the reaction temperature is between 380 and 420 ℃; discharging the hydrogen after the reaction, cooling the residual materials, rectifying and separating the cooled residual materials one by one to obtain monoethylamine and acetonitrile, and purifying the acetonitrile to obtain a preparation product. According to the technical scheme, the acetonitrile is directly generated by using the monoethylamine, no water is generated in the reaction process, the dehydration process is avoided, the per-pass conversion rate of the raw materials is high, the selectivity is good, the generated hydrogen can be used as a byproduct, and the process flow is simple.
Description
Technical Field
The invention relates to the technical field of acetonitrile preparation processes, in particular to a preparation method of acetonitrile.
Background
Acetonitrile is widely used as a chemical reaction solvent, and particularly used as a solvent for synthesis of pharmaceutical intermediates, a solvent for purification, a solvent for liquid chromatography, a solvent for DNA synthesis/purification, a solvent for synthesis of organic light-emitting materials, a solvent for cleaning electronic devices, and the like. Various applications require high purity of acetonitrile.
Currently, commercially available acetonitrile is mainly obtained by recovering and purifying crude acetonitrile, and the crude acetonitrile is obtained by producing acrylonitrile and methacrylonitrile as byproducts through the oxidation of propylene or isobutene and ammonia gas. The crude acetonitrile as a by-product contains many impurities such as allyl cyanide, propanol, oxazole, acetone, hydrocyanic acid, methyl acrylonitrile, acrolein, propionaldehyde, butene cyanide, methyl acrylate, methacrylic acid, methyl acetate, methyl methacrylate and the like.
The existing method for preparing high-purity acetonitrile needs to carry out multi-step purification on crude acetonitrile to remove impurities such as propionitrile, acrylonitrile and the like in the crude acetonitrile. For example, cn200680015870.x discloses a method for purifying acetonitrile, and also mentions a series of acetonitrile purification methods; for example, one of the process routes mentioned in CN 101774944B, in which ethylamine, or ethanol/acetaldehyde ammonia, is directly oxidized with oxygen to produce acetonitrile with high selectivity, would have a large amount of water generated in the process, and the use of conventional distilled water azeotroped with acetonitrile increases the energy consumption in separating water.
Disclosure of Invention
In order to solve the problems, the invention provides the preparation method of the acetonitrile, the acetonitrile is directly generated by using the monoethylamine through gas-solid phase reaction, no water is generated in the reaction process, the dehydration process is avoided, the per-pass conversion rate of the raw materials is high, the selectivity is good, the generated hydrogen can be used as a byproduct, and the process flow is simple.
In order to achieve the above object, the present invention provides a method for preparing acetonitrile, comprising:
vaporizing monoethylamine and adding Cu-Zn-Pt/Al2O3Is used as a catalyst and is subjected to gas-solid reaction with hydrogen in a reactor, wherein the reaction pressure in the reactor is kept between 0.01MPa and 0.05MPa, and the reaction temperature is between 380 and 420 ℃;
discharging the hydrogen after the reaction, cooling the residual materials, rectifying and separating the cooled residual materials one by one to obtain monoethylamine and acetonitrile, and purifying the acetonitrile to obtain a preparation product.
In the above technical solution, preferably, the catalystIn the chemical agent, the weight percentage of Cu is 20-25%, Zn is 12-18%, Pt is 0.2%, and the rest is Al2O3。
In the above technical solution, preferably, the monoethylamine is input into a vaporizer to be vaporized, and the hydrogen is input into the vaporizer by a compressor, so that the vaporized monoethylamine and the hydrogen enter the fixed bed reactor together to react.
In the above technical solution, preferably, the hydrogen is discharged in time after the reaction in the reactor is completed, so that the reaction pressure in the reactor is maintained at 0.01MPa to 0.05 MPa.
In the above technical solution, preferably, the monoethylamine is input through a metering pump, and the feeding rate corresponding to the monoethylamine is 50ml/h for every 1000ml of catalyst in the reactor.
In the above technical solution, preferably, the Cu-Zn-Pt/Al2O3The preparation method of the catalyst comprises the following steps:
mixing Al (OH)3Preparing sodium metaaluminate solution by using 40% NaOH, neutralizing and precipitating by using nitric acid, aging, filtering, washing, rolling ball forming, drying and roasting to obtain spherical Al with the diameter of 3mm2O3A carrier;
preparing mixed solution of nitrates of Cu, Zn and Pt according to a certain proportion, and adding Al2O3The carrier is impregnated, dried and then put into a muffle furnace and roasted for 6 hours at 490 ℃ to prepare the catalyst.
In the above technical solution, preferably, the reactor adopts a closed cycle structure, and the discharged hydrogen is collected.
In the above technical solution, preferably, the separated monoethylamine is returned to continue the cyclic reaction.
Compared with the prior art, the invention has the beneficial effects that: the acetonitrile is directly generated by using monoethylamine through gas-solid phase reaction, no water is generated in the reaction process, the dehydration process is avoided, the per-pass conversion rate of the raw materials is high, the selectivity is good, the generated hydrogen can be used as a byproduct, and the process flow is simple.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The invention is described in further detail below:
the preparation method of the acetonitrile provided by the invention comprises the following steps:
vaporizing monoethylamine and adding Cu-Zn-Pt/Al2O3Is used as a catalyst and is subjected to gas-solid reaction with hydrogen in a reactor, wherein the reaction pressure in the reactor is kept between 0.01MPa and 0.05MPa, and the reaction temperature is between 380 and 420 ℃;
discharging the hydrogen after the reaction, cooling the residual materials, rectifying and separating the cooled residual materials one by one to obtain monoethylamine and acetonitrile, and purifying the acetonitrile to obtain a preparation product.
In the embodiment, the acetonitrile is directly generated by using the monoethylamine through the gas-solid phase reaction, no water is generated in the reaction process, the dehydration process is avoided, the per-pass conversion rate of the raw materials is high, the selectivity is good, the generated hydrogen can be used as a byproduct, and the process flow is simple.
Specifically, the preparation method uses monoethylamine as a raw material and uses Cu-Zn-Pt/Al2O3The method is characterized in that the method is carried out in a gas-solid phase by adopting a continuous process, monoethylamine is input into a vaporizer, hydrogen is input into the vaporizer by adopting a compressor in a hydrogen system, the vaporized monoethylamine and hydrogen enter a fixed bed reactor together for reaction, the reacted material is cooled by a heat exchanger and then enters a separator, the material in the separator is rectified and separated one by one to obtain monoethylamine and acetonitrile, and the acetonitrile is purified to obtain the product.
In the preparation process, no water is generated, and the water and the acetonitrile are subjected to azeotropic distillation, so that the defect that water and the acetonitrile are difficult to separate in the process preparation is overcome, the dehydration process is reduced, and the energy consumption is reduced.
The dehydrogenation reaction is utilized to prepare the acetonitrile, no ammonia gas is involved in the preparation process, and compared with the acetonitrile preparation process which adopts ethanol, acetic acid and ammonia as raw materials, the method has fewer byproducts and is convenient for separating and purifying the acetonitrile.
In the above embodiment, it is preferable that the hydrogen is discharged in time after the reaction in the reactor is completed, so that the reaction pressure in the reactor is always maintained at 0.01MPa to 0.05 MPa.
In the above example, preferably, monoethylamine is fed in by means of a metering pump, and the feeding rate for monoethylamine is 50ml/h for every 1000ml of catalyst in the reactor.
In the above embodiment, preferably, in the catalyst, by weight percentage, Cu is 20% to 25%, Zn is 12% to 18%, Pt is 0.2%, and the balance is Al2O3。
Preferably, the Cu-Zn-Pt/Al2O3The preparation method of the catalyst comprises the following steps:
mixing Al (OH)3Preparing sodium metaaluminate solution by using 40% NaOH, neutralizing and precipitating by using nitric acid, aging, filtering, washing, rolling ball forming, drying and roasting to obtain spherical Al with the diameter of 3mm 2O3A carrier;
preparing mixed solution of nitrates of Cu, Zn and Pt according to a certain proportion, and adding Al2O3The carrier is impregnated, dried and then put into a muffle furnace and roasted for 6 hours at 490 ℃ to prepare the catalyst. After the catalyst is loaded into the reactor, pure hydrogen is used for 1000h under the pressure of 0.05MPa, the temperature of 460 ℃ and the space velocity-1Reducing for 24 hours under the condition.
In the above embodiment, preferably, the reactor adopts a closed cycle structure, the reaction is dehydrogenation reaction, the pressure is kept low to facilitate the reaction, and as the reaction proceeds, the pressure of the system will rise continuously, so that hydrogen is not removed in time, the danger of the reaction is increased, and the dehydrogenation reaction is not facilitated, so that the hydrogen needs to be removed and collected as a byproduct.
In the above examples, the monoethylamine obtained by separation is preferably returned as a starting material to continue the cyclic reaction.
The preparation of acetonitrile according to the above-mentioned example is illustrated by the following specific example, wherein in the following examples the experimental data are given after 480h of feed followed by emptying of the separator and 2h of feed followed by discharge of the separator and sampling by Agilent Technologies chromatography.
In the following examples, the conditions and data of each example, unless otherwise specified, are subject to the following conditions: the catalyst comprises the following components, by weight, 20-25% of Cu, 12-18% of Zn, 0.2% of Pt and the balance of Al2O3The reaction pressure used was 0.05 MPa.
Example 1
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn, 0.2% of Pt and the balance of Al2O3The reaction temperature is 380 ℃, the feeding speed is 50ml/h, and the data obtained in the experiment are as follows:
| monoethylamine | Acetonitrile |
| 2.25 | 97.71 |
Example 2
The catalyst comprises the following components in proportion: 20% of Cu, 15% of Zn, 0.2% of Pt and the balance of Al2O3The reaction temperature was 390 ℃, the feed rate was 50ml/h, and the experimental data were:
| monoethylamine | Acetonitrile |
| 2.13 | 97.79 |
Example 3
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn, 0.2% of Pt and the balance of Al2O3The reaction temperature was 410 ℃ and the feed rate was 50ml/h, and the experimental data were:
| monoethylamine | Acetonitrile |
| 2.11 | 97.81 |
Example 4
The catalyst comprises the following components in proportion: 23% of Cu, 16% of Zn, 0.2% of Pt and the balance of Al2O3The reaction temperature was 410 ℃ and the feed rate was 50ml/h, and the experimental data were:
| monoethylamine | Acetonitrile |
| 1.94 | 97.99 |
Example 5
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn, 0.2% of Pt and the balance of Al 2O3The reaction temperature is 420 ℃, the feeding speed is 50ml/h, and the data obtained in the experiment are as follows:
| monoethylamine | Acetonitrile |
| 1.45 | 98.10 |
Example 6
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn, 0.2% of Pt and the balance of Al2O3The reaction temperature is 420 ℃, the feeding speed is 60ml/h, and the data obtained in the experiment are as follows:
| monoethylamine | Acetonitrile |
| 6.15 | 93.68 |
Example 7
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn, 0.2% of Pt and the balance of Al2O3The reaction temperature is 350 ℃, the feeding speed is 50ml/h, and the data obtained by the experiment are as follows:
| monoethylamine | Acetonitrile |
| 12.35 | 87.60 |
Example 8
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn, 0.2% of Pt and the balance of Al2O3The reaction temperature is 450 ℃, the feeding speed is 50ml/h, and the data obtained by the experiment are as follows:
| monoethylamine | Acetonitrile | Other substances |
| 1.21 | 89.32 | 9.44 |
When the reaction temperature is increased to 450 ℃, other substances are generated under the condition that the feeding speed is not changed, which is not beneficial to the preparation of the acetonitrile.
Example 9
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn and the balance of Al2O3The reaction temperature is 380 ℃, the feeding speed is 50ml/h, and the data obtained in the experiment are as follows:
| monoethylamine | Acetonitrile |
| 20.34 | 79.57 |
Example 10
The catalyst comprises the following components in proportion: 25% of Cu, 18% of Zn, 0.2% of Pt and the balance of Al 2O3The reaction temperature is 380 ℃, the reaction pressure is 0.3MPa, the feeding speed is 50ml/h, and the experimental data are as follows:
| monoethylamine | Acetonitrile |
| 7.56 | 92.33 |
As can be seen from the analysis of the experimental data of examples 1 to 8, the optimum process parameters for the acetonitrile preparation process are: the reaction temperature is 380-420 ℃, and the feeding amount is 25ml/h per 1000ml of catalyst.
As can be seen from the analysis of the test data of examples 1 to 5, the temperature gradually increased and the conversion of monoethylamine gradually increased in the reaction temperature range of 380 to 420 ℃ under the same reaction conditions.
A comparison of the test data from examples 7 and 8 with those from examples 1 to 5 shows that the conversion of monoethylamine is significantly reduced beyond the reaction temperature range of 380 ℃ to 420 ℃. Moreover, after the reaction temperature exceeds 420 ℃, monoethylamine can be decomposed to generate other substances, which is not beneficial to the preparation of acetonitrile.
The feeding time is prolonged for the embodiment 1-embodiment 5 under the same condition, and the obtained experimental data are compared with the experimental data of 480h feeding after the 720h continuous feeding, the conversion rate of monoethylamine and the selectivity of acetonitrile are not changed greatly, further, the catalyst prepared by the process has longer service life and is suitable for industrial production.
According to the comparison of the experimental data of the example 1 and the example 9, the addition of Pt in the catalyst effectively improves the conversion rate of monoethylamine and reduces the reaction temperature.
From a comparison of the experimental data of example 1 and example 10, it can be seen that the conversion of monoethylamine is higher for a reaction pressure of 0.5MPa compared to a reaction pressure of 0.3MPa under otherwise identical reaction conditions.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. A method for preparing acetonitrile is characterized by comprising the following steps:
vaporizing monoethylamine and adding Cu-Zn-Pt/Al2O3Is a catalyst, and is subjected to gas-solid reaction with hydrogen in a reactor, whereinThe reaction pressure in the reactor is kept between 0.01MPa and 0.05MPa, and the reaction temperature is between 380 and 420 ℃;
discharging the hydrogen after the reaction, cooling the residual materials, rectifying and separating the cooled residual materials one by one to obtain monoethylamine and acetonitrile, and purifying the acetonitrile to obtain a preparation product.
2. The method for preparing acetonitrile according to claim 1, wherein the catalyst comprises, by weight, 20% to 25% of Cu, 12% to 18% of Zn, 0.2% of Pt, and the balance Al2O3。
3. The method for preparing acetonitrile according to claim 1, wherein the monoethylamine is fed into a vaporizer to be vaporized, and the hydrogen is fed into the vaporizer by a compressor, so that the vaporized monoethylamine and the hydrogen are fed into the fixed bed reactor together to be reacted.
4. The method for preparing acetonitrile according to claim 1, wherein hydrogen is discharged in time after the completion of the reaction in the reactor so that the reaction pressure in the reactor is maintained at 0.01 to 0.05 MPa.
5. The process for the preparation of acetonitrile according to claim 1 or 3, wherein the monoethylamine is fed by means of a metering pump, and the feeding rate of the monoethylamine is 50ml/h for every 1000ml of catalyst contained in the reactor.
6. The method for the preparation of acetonitrile according to claim 2, wherein the Cu-Zn-Pt/Al is2O3The preparation method of the catalyst comprises the following steps:
mixing Al (OH)3Preparing sodium metaaluminate solution by using 40% NaOH, neutralizing and precipitating by using nitric acid, aging, filtering, washing, rolling ball forming, drying and roasting to obtain spherical Al with the diameter of 3mm 2O3A carrier;
preparing mixed solution of nitrates of Cu, Zn and Pt according to a certain proportion, and adding Al2O3The carrier is impregnated, dried and then put into a muffle furnace and roasted for 6 hours at 490 ℃ to prepare the catalyst.
7. The method for producing acetonitrile according to claim 1, wherein the reactor employs a closed cycle structure and is configured to collect hydrogen gas discharged.
8. The method for preparing acetonitrile according to claim 1, wherein the separated monoethylamine is returned to continue the cyclic reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110927263.7A CN113620836B (en) | 2021-08-13 | 2021-08-13 | Preparation method of acetonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110927263.7A CN113620836B (en) | 2021-08-13 | 2021-08-13 | Preparation method of acetonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113620836A true CN113620836A (en) | 2021-11-09 |
| CN113620836B CN113620836B (en) | 2022-08-05 |
Family
ID=78385040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110927263.7A Active CN113620836B (en) | 2021-08-13 | 2021-08-13 | Preparation method of acetonitrile |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113620836B (en) |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB590768A (en) * | 1942-02-19 | 1947-07-28 | Alais & Froges & Camarque Cie | Method of preparation of acetonitrile |
| GB870462A (en) * | 1958-03-06 | 1961-06-14 | State Of Japan | Improvements in or relating to the production of acetonitrile |
| US4179462A (en) * | 1975-06-30 | 1979-12-18 | Monsanto Company | Process for preparing acetonitrile |
| CN101497043A (en) * | 2008-02-01 | 2009-08-05 | 北京石油化工学院 | Catalyst for preparing liquefied petroleum gas and preparation method thereof |
| CN101648888A (en) * | 2009-09-21 | 2010-02-17 | 浙江新化化工股份有限公司 | Method for preparing acetonitrile |
| CN101774944A (en) * | 2010-02-09 | 2010-07-14 | 南京工业大学 | Acetonitrile production process |
| US20100210878A1 (en) * | 2009-02-17 | 2010-08-19 | Asemblon, Inc. | Release and Recovery from Aliphatic Primary Amines or Di-Amines |
| JP2010209010A (en) * | 2009-03-11 | 2010-09-24 | Koei Chem Co Ltd | Method for producing acetonitrile |
| CN102039195A (en) * | 2009-10-16 | 2011-05-04 | 中国石油化工股份有限公司 | Preparation method of alumina carrier |
| CN104671264A (en) * | 2015-03-23 | 2015-06-03 | 天津凯美科技有限公司 | Preparation method of mesoporous alumina |
| WO2016068068A1 (en) * | 2014-10-31 | 2016-05-06 | 旭化成ケミカルズ株式会社 | Method for producing acetonitrile |
| WO2016068062A1 (en) * | 2014-10-31 | 2016-05-06 | 旭化成ケミカルズ株式会社 | Method for producing acetonitrile |
| CN107814751A (en) * | 2016-09-13 | 2018-03-20 | 淮海工学院 | A kind of method that catalysis oxidation amine prepares nitrile |
| CN110294689A (en) * | 2019-06-24 | 2019-10-01 | 大连理工大学 | A kind of method that the metal complex catalyzed primary amine dehydrogenation of ruthenium prepares nitrile compounds |
| CN111635334A (en) * | 2020-07-13 | 2020-09-08 | 四川大学 | Method for generating nitrile by catalyzing primary amine acceptor-free dehydrogenation through Ru complex |
-
2021
- 2021-08-13 CN CN202110927263.7A patent/CN113620836B/en active Active
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB590768A (en) * | 1942-02-19 | 1947-07-28 | Alais & Froges & Camarque Cie | Method of preparation of acetonitrile |
| GB870462A (en) * | 1958-03-06 | 1961-06-14 | State Of Japan | Improvements in or relating to the production of acetonitrile |
| US4179462A (en) * | 1975-06-30 | 1979-12-18 | Monsanto Company | Process for preparing acetonitrile |
| CN101497043A (en) * | 2008-02-01 | 2009-08-05 | 北京石油化工学院 | Catalyst for preparing liquefied petroleum gas and preparation method thereof |
| US20100210878A1 (en) * | 2009-02-17 | 2010-08-19 | Asemblon, Inc. | Release and Recovery from Aliphatic Primary Amines or Di-Amines |
| JP2010209010A (en) * | 2009-03-11 | 2010-09-24 | Koei Chem Co Ltd | Method for producing acetonitrile |
| CN101648888A (en) * | 2009-09-21 | 2010-02-17 | 浙江新化化工股份有限公司 | Method for preparing acetonitrile |
| CN102039195A (en) * | 2009-10-16 | 2011-05-04 | 中国石油化工股份有限公司 | Preparation method of alumina carrier |
| CN101774944A (en) * | 2010-02-09 | 2010-07-14 | 南京工业大学 | Acetonitrile production process |
| WO2016068068A1 (en) * | 2014-10-31 | 2016-05-06 | 旭化成ケミカルズ株式会社 | Method for producing acetonitrile |
| WO2016068062A1 (en) * | 2014-10-31 | 2016-05-06 | 旭化成ケミカルズ株式会社 | Method for producing acetonitrile |
| CN104671264A (en) * | 2015-03-23 | 2015-06-03 | 天津凯美科技有限公司 | Preparation method of mesoporous alumina |
| CN107814751A (en) * | 2016-09-13 | 2018-03-20 | 淮海工学院 | A kind of method that catalysis oxidation amine prepares nitrile |
| CN110294689A (en) * | 2019-06-24 | 2019-10-01 | 大连理工大学 | A kind of method that the metal complex catalyzed primary amine dehydrogenation of ruthenium prepares nitrile compounds |
| CN111635334A (en) * | 2020-07-13 | 2020-09-08 | 四川大学 | Method for generating nitrile by catalyzing primary amine acceptor-free dehydrogenation through Ru complex |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113620836B (en) | 2022-08-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111004148A (en) | Method for preparing 6-aminocapronitrile by gas phase method | |
| JP6485456B2 (en) | Method for producing γ, δ-unsaturated alcohol | |
| US9914693B2 (en) | Process for preparing EDA using SO2-free hydrocyanic acid | |
| EP2937326A1 (en) | 1, 3, 3, 3-tetrafluoropropene preparation process | |
| US8710269B2 (en) | DMAPN having a low DGN content and a process for preparing DMAPA having a low DGN content | |
| EP4192810A1 (en) | Production of dinitriles | |
| CN105237434A (en) | Method for producing cyclohexanone oxime | |
| TW200812957A (en) | Process for preparing alpha-hydroxycarboxylic esters | |
| CN113620836B (en) | Preparation method of acetonitrile | |
| US2519803A (en) | Preparation of ethylene diamines | |
| JP2011507830A (en) | Method for producing N-methylpyrrolidone | |
| CN109761819B (en) | Continuous preparation method of N, N-dimethylpropylamine | |
| CN101648888B (en) | Method for preparing acetonitrile | |
| CN109438216B (en) | Preparation method of high-purity isooctanoic acid | |
| CN109956888B (en) | Method for preparing adiponitrile by catalytic ammoxidation and cracking of cyclohexanol | |
| CN113072461B (en) | Preparation method of butanone oxime | |
| US7393981B2 (en) | Method of preparation of methyl-benzyl-ketone | |
| CN1660758A (en) | Process for the selective (AMM) oxidation of lower molecular weight alkanes and alkenes | |
| TW201211000A (en) | Method for producing n-propyl acetate and method for producing allyl acetate | |
| CN111036268A (en) | Alumina composite material, preparation method and application thereof, and synthetic method of n-valeronitrile | |
| US4365090A (en) | Process for production of acrylamide | |
| CN114349661B (en) | Method for preparing alkanedinitrile by liquid phase ammoxidation | |
| NL2030511B1 (en) | Integrated process for the conversion of glycerol to acrylonitrile | |
| CA3172662C (en) | Method for preparing phthalonitrile-based compound | |
| CN109988082B (en) | Method for preparing acrylonitrile by continuous oxidative dehydrogenation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method for acetonitrile Effective date of registration: 20230627 Granted publication date: 20220805 Pledgee: Binzhou Zhanhua sub branch of Postal Savings Bank of China Ltd. Pledgor: Shandong Damin Chemical Co.,Ltd. Registration number: Y2023980046142 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |