Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C253/00—Preparation of carboxylic acid nitriles
  • C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
  • C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
  • C07C255/03—Mononitriles
• • 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
  • B01J29/00—Catalysts comprising molecular sieves
  • B01J29/82—Phosphates
  • B01J29/84—Aluminophosphates containing other elements, e.g. metals, boron
  • B01J29/85—Silicoaluminophosphates [SAPO compounds]
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
  • C07B61/00—Other general methods

Definitions

• the present invention relates to a method for producing acetonitrile.
• Acetonitrile is used as a solvent for chemical reaction, particularly a solvent used for synthesis and purification of pharmaceutical intermediates, a mobile phase solvent for high performance liquid chromatography, and the like. Recently, acetonitrile is also used as a solvent for DNA synthesis and a solvent for purification, a solvent for organic EL material synthesis, and a solvent for washing electronic components.
• acetonitrile is mainly crude acetonitrile obtained as a by-product in the production of acrylonitrile or methacrylonitrile by catalytic ammoxidation reaction of propylene or isobutene, ammonia and oxygen. , Recovered and purified. Since the crude acetonitrile obtained by the ammoxidation reaction thus obtained contains various impurities, many methods for purifying the crude acetonitrile have been proposed so far.
• Patent Document 1 discloses that crude acetonitrile containing hydrous acetonitrile is mixed with an amount of alkali sufficient to extract water present therein and mixed at 10 to 50 ° C., and then the separated aqueous phase is removed.
• a dehydration and purification method is disclosed.
• Patent Document 2 discloses a method in which crude acetonitrile produced as a by-product by an ammoxidation reaction is alkali-treated at 60 ° C. to decompose hydrogen cyanide and acrylonitrile, and then further alkali is added in a dehydration tower to dehydrate acetonitrile. ing.
• Patent Document 3 in a method for producing acetonitrile by reacting acetic acid and ammonia in the gas phase in the presence of a catalyst, the reaction product gas is brought into contact with a strong acid to recover acetonitrile as an aqueous solution.
• the catalyst used in this method may be a dehydration catalyst having an acid site and / or a base site,
• the catalyst disclosed in the examples is zirconia.
• Patent Document 4 discloses that in a method for producing nitrile from carboxylic acid and ammonia using various zeolite catalysts, the ammonia / carboxylic acid molar ratio is 1/1 to 10/1, and H-ZSM-5 is used as the catalyst.
• NaY a zeolite such as H-mordenite, SAPO-40, silica alumina, etc.
• a reaction temperature of 300 to 500 ° C. and a WHSV of liquid product basis of 0.4 h ⁇ 1 are disclosed.
• JP-A-55-153757 JP 2000-128847 A Japanese Patent No. 5173897 Indian Patent No. 187529
• Patent Document 3 discloses that ammonium carbonate precipitation is a problem of the method, and it is disclosed that ammonium carbonate crystal precipitation can be suppressed by a method in which a reaction product gas is brought into contact with a strong acid. There is no description about the above, and no problems in purifying hydrous crude acetonitrile to high-purity acetonitrile are shown.
• Patent Document 4 discloses a method for producing acetonitrile from acetic acid and ammonia using various zeolite catalysts, and according to this example, the yield is disclosed as 100%.
• the amount of catalyst used is large, which is disadvantageous for industrial implementation, there is no description about trace impurities, and no problems are shown in purifying to high purity acetonitrile.
• Acetonitrile is used as a solvent for chemical reaction, particularly a solvent used for synthesis and purification of pharmaceutical intermediates, a mobile phase solvent for high performance liquid chromatography, and the like. Therefore, even if it is a trace amount, the by-product of an aromatic compound is a big problem in the product quality of acetonitrile.
• Patent Document 3 has proposed a method in which an acetic acid raw material is supplied by being dissolved in an aromatic hydrocarbon as a solvent for acetic acid.
• the present invention has been made in view of the above problems, and a method for producing acetonitrile capable of suppressing the by-product of an aromatic compound when a gas phase reaction between acetic acid and ammonia is performed using a zeolite catalyst.
• the purpose is to provide.
• the acetonitrile thus obtained is a solvent for chemical reaction, particularly a pharmaceutical intermediate synthesis solvent and purification solvent, a high-performance liquid chromatography mobile phase solvent, a DNA synthesis solvent and purification solvent, and an organic EL material. It can be suitably used as a solvent for synthesis or as a cleaning solvent for electronic parts.
• the present inventors have found that the above problems can be solved by using a predetermined zeolite catalyst, and have completed the present invention.
• the present invention is as follows. [1] Having a gas phase reaction step in which acetic acid and ammonia are subjected to a gas phase reaction in the presence of a zeolite catalyst to obtain hydrous crude acetonitrile, A method for producing acetonitrile, wherein the zeolite catalyst has an oxygen 8-membered ring pore structure. [2] The method for producing acetonitrile according to [1], wherein the content of toluene in the hydrous crude acetonitrile is less than 1 ppm by mass with respect to 100% by mass of acetonitrile.
• acetonitrile capable of suppressing the by-production of an aromatic compound when performing a gas phase reaction between acetic acid and ammonia using a zeolite catalyst.
• the method for producing acetonitrile of the present invention is extremely advantageous in industrially performing a gas phase reaction between acetic acid and ammonia using a zeolite catalyst.
• Acetonitrile thus obtained is a solvent for chemical reaction, particularly a pharmaceutical intermediate synthesis solvent, a purification solvent, a mobile phase solvent for high performance liquid chromatography, a DNA synthesis solvent and a purification solvent, and an organic EL material. It can be suitably used as a solvent for synthesis or as a cleaning solvent for electronic parts.
• the present embodiment the embodiment of the present invention (hereinafter referred to as “the present embodiment”) will be described in detail.
• the present invention is not limited to this, and various modifications are possible without departing from the scope of the present invention. It is. Note that the expression “A to B” in a numerical range indicates a numerical range of “A or more and B or less” unless otherwise specified.
• the method for producing acetonitrile according to the present embodiment includes a gas phase reaction step in which acetic acid and ammonia are subjected to a gas phase reaction in the presence of a zeolite catalyst to obtain hydrous crude acetonitrile. It has a structure.
• a zeolite catalyst having a pore structure with an oxygen 8-membered ring pore structure as the catalyst, surprisingly, by-products of aromatic compounds such as toluene in the resulting hydrous crude acetonitrile Can be remarkably suppressed.
• high purity acetonitrile substantially free of aromatic compounds such as toluene can be produced by subjecting the obtained hydrous crude acetonitrile to extraction dehydration and distillation purification by a conventionally known method.
• “Substantially free of aromatic compounds” means that the content of aromatic compounds is less than 1 ppm by mass.
• high-purity acetonitrile having a low absorbance of ultraviolet absorption at a wavelength of 200 to 400 nm can be obtained.
• the ability to suppress the by-product of the aromatic compound is extremely advantageous in practicing the present invention industrially.
• the gas phase reaction step is a step in which acetic acid and ammonia are reacted in a gas phase in the presence of a zeolite catalyst to obtain hydrous crude acetonitrile. Specifically, it can be carried out by bringing gas-phase contact between acetic acid, ammonia and a zeolite catalyst at a predetermined temperature in a reactor filled with a zeolite catalyst, but is not particularly limited.
• Acetic acid and ammonia as raw materials for the gas phase reaction are not particularly limited, and those produced from various chemical synthesis methods can be used.
• Acetic acid and ammonia are not necessarily highly pure, and may be industrial grade.
• acetic acid that is commercially available as a 70 to 90% by mass aqueous solution can be used for the purpose of preventing freezing in winter.
• the zeolite catalyst used in the present embodiment has an oxygen 8-membered ring pore structure.
• the present inventors have found that by-production of aromatic compounds is suppressed when the zeolite catalyst has an oxygen 8-membered ring pore structure.
• zeolite is a general term for crystalline porous aluminosilicates. Zeolite has (SiO 4 ) 4- and (AlO 4 ) 5- having a tetrahedral structure as basic structural units, and these are three-dimensionally connected to form crystals.
• metallosilicates in which trivalent or tetravalent elements other than aluminum ions are incorporated in the silicate skeleton are also included in the zeolite.
• Zeolite is diverse in structure and composition, so it is classified differently from various viewpoints such as structure code, formation process, mineralogy, pore size, pore dimension, aluminum concentration, other cation concentration and structural elements. (See Zeolite Science and Engineering, Yoshio Ono and Kenaki Yashima / Edition, Kodansha Scientific). Various framework type codes are defined by the International Zeolite Society (IZA).
• the structure of the zeolite catalyst having an oxygen 8-membered ring pore structure is not particularly limited.
• FTC framework type code
• IZA International Zeolite Society
• AFX AFX
• CAS CAS
• CHA DDR
• ERI ESV
• GIS GOO
• ITE ITE
• JBW KFI
• LEV LTA
• MER MON
• MTF PAU
• PHI RHO
• RTE RTH
• a zeolite catalyst which has a CHA structure which has a CHA structure
• aluminosilicate “SSZ-13” composed of silicon and aluminum
• aluminophosphate “ALPO-34” composed of aluminum and phosphorus
• SAPO-34 silicoaluminophosphate
• SAPO-34 silicoaluminophosphate
• the zeolite catalyst may be in the form of powder or granule, and can be formed into a shape that is molded into a suitable shape according to a process such as a gas phase reaction step.
• the method for forming the zeolite catalyst is not particularly limited, and a known method can be used. For example, a method of spray-drying a catalyst precursor, a method of compression-molding a catalyst component, and a method of extrusion-molding a catalyst component can be mentioned. In these molding methods, a binder or a diluent for molding (matrix) may be used.
• the binder and the diluent for molding are not particularly limited, and examples thereof include porous refractory inorganic oxides such as silica, alumina, zirconia, titania, kaolin, diatomaceous earth, and clay. These may be used individually by 1 type, or may use 2 or more types together.
• the reactor used in the gas phase reaction step is not particularly limited, and examples thereof include a fixed bed reactor, a fluidized bed reactor, and a moving bed reactor.
• a reaction system either a batch system or a flow system can be used, but a flow system is preferable in consideration of productivity. Note that the description in the present specification does not preclude changes in reaction conditions that can be easily adjusted by those skilled in the art.
• a granular material inactive to reaction such as quartz sand and a ceramic ball
• this granular material is a particle size comparable as a catalyst from a uniform mixing property with a catalyst.
• the gas phase reaction is an endothermic reaction
• the reaction substrate reaction raw material
• the reaction substrate may be divided and supplied to the reactor for the purpose of dispersing the endotherm accompanying the reaction.
• the molar ratio of ammonia / acetic acid supplied to the reactor is preferably 1.0 or more, more preferably 1.0 to 2.0, and still more preferably 1.1 to 1.
• the range is 5.
• the reaction efficiency tends to be further improved.
• the ammonia / acetic acid molar ratio is 1.5 or less, the energy consumption for separating and removing ammonia from hydrous crude acetonitrile described later tends to be further reduced in the purification step.
• WHSV weight space velocity
• WHSV weight space velocity
• the “catalyst filling weight” means the filling weight of the zeolite catalyst in the reactor in the present embodiment.
• the binder or the molding diluent constituting the molded body It is a reactor filling weight of the whole molded object containing.
• the above-mentioned inert particulate matter is not included in the catalyst filling weight.
• the “raw material weight” here is the total weight of the raw materials flowing to the reactor, and the “raw material” includes acetic acid or an aqueous acetic acid solution and ammonia, which are raw materials in the present embodiment, and a diluent described later Is also included.
• WHSV can be adjusted as appropriate in consideration of productivity, catalyst life, and reaction yield.
• the WHSV in the vapor phase reaction step preferably 0.5 ⁇ 50h -1, more preferably 0.5 ⁇ 20h -1, more preferably from 0.5 ⁇ 10h -1.
• the reactor can be made compact, and byproducts of undesirable by-products such as acetone and toluene can be reduced.
• the raw material can be suppressed and the purification load on high-purity acetonitrile can be further reduced.
• WHSV is 50 h ⁇ 1 or less, the conversion of acetic acid tends to be further improved, and the selectivity of acetonitrile tends to be further improved.
• a diluent may be used in addition to acetic acid and ammonia.
• the diluent is not particularly limited, and examples thereof include helium, argon, nitrogen, water, paraffinic hydrocarbon gases, and Examples thereof include gases inert to the reaction, such as a mixture thereof. Of these, nitrogen and water are preferred.
• impurities contained in the reaction raw material may be used as they are, or a separately prepared diluent may be mixed with the reaction raw material and used.
• the diluent may be mixed with the reaction raw material before entering the reactor, or may be supplied to the reactor separately from the reaction raw material.
• reaction temperature of the gas phase reaction is preferably 250 ° C. or higher, more preferably 300 ° C. or higher, and further preferably 350 ° C. or higher.
• the reaction temperature of the gas phase reaction is preferably 600 ° C. or lower, more preferably 550 ° C. or lower, and further preferably 520 ° C. or lower.
• reaction temperature is 250 ° C. or higher, the reaction yield tends to be further improved.
• reaction temperature is 600 degrees C or less, it exists in the tendency which can suppress the production
• the gas phase reaction in this embodiment is a dehydration reaction (endothermic reaction)
• a heat source in the reactor in order to control the inside of the reactor to a desired reaction temperature.
• a gas phase reaction is industrially carried out in a fixed bed reactor, it is conceivable to use a multi-tubular shell and tube reactor.
• reaction pressure of the gas phase reaction is advantageously low in terms of the reaction equilibrium of the gas phase reaction of the present embodiment, but the reaction rate increases if the pressure is high. Accordingly, it is a balance between the equilibrium conversion rate and the reaction rate, preferably normal pressure to 0.3 MPaG (gauge pressure, the same shall apply hereinafter), more preferably 0.03 to 0.25 MPaG, and still more preferably 0. .05 to 0.20 MPaG.
• the “hydrated crude acetonitrile” includes 10% by mass to 70% by mass of acetonitrile and 30% by mass to 90% by mass of water, and may contain 0% by mass to 60% by mass of impurities. It is a composition.
• impurities include, but are not limited to, ammonia, acetic acid, acetamide, and acetone.
• the content of toluene in the hydrous crude acetonitrile obtained by the gas phase reaction of the present embodiment is preferably less than 1 ppm by mass, more preferably less than 0.5 ppm by mass with respect to 100% by mass of acetonitrile, More preferably, it is less than 0.2 mass ppm.
• the lower limit of the content of toluene in the hydrous crude acetonitrile is not particularly limited, but is preferably not more than the detection limit, and more preferably 0% by mass with respect to 100% by mass of acetonitrile.
• Toluene is an impurity that is extremely difficult to remove in the purification process described later.
• the toluene content of the product acetonitrile obtained through the purification step is also low.
• the product acetonitrile thus obtained is a product suitable for various solvents.
• the content of toluene in the obtained hydrous crude acetonitrile can be reduced by using a zeolite catalyst having an 8-membered ring pore structure defined in the present embodiment.
• content of toluene in hydrous crude acetonitrile can be measured by the method as described in an Example.
• the method for producing acetonitrile of the present embodiment may include a purification step of purifying water-containing crude acetonitrile to obtain product acetonitrile.
• the step included in the purification step is not particularly limited as long as it is configured to remove water, ammonia and other impurities from the hydrous crude acetonitrile, but for example, a concentration step, a dehydration step, a low boiling point removal step, a high boiling point, and the like. Examples include a minute removal step.
• the concentration step is a step in which ammonia is separated from hydrous crude acetonitrile to obtain crude acetonitrile.
• a separation method of ammonia For example, the method of using a distillation column is mentioned.
• “crude acetonitrile” is acetonitrile obtained by removing ammonia from hydrous crude acetonitrile, and concentrated mainly from 50% by mass to less than 75% by mass of acetonitrile, and from 25% by mass to 50% by mass. It is a mixture that may contain water and other impurities.
• the dehydration step is a step in which water is separated from crude acetonitrile to obtain dehydrated acetonitrile.
• the method for separating water is not particularly limited, and examples thereof include a method of adding alkali to crude acetonitrile and performing extraction dehydration. Although it does not specifically limit as an alkali which can be used, For example, caustic soda is mentioned.
• the amount of alkali used can be appropriately adjusted depending on the water content in the crude acetonitrile, and is preferably 10 to 90% by mass, more preferably 30 to 60% by mass, based on the water content of the crude acetonitrile. %.
• the extraction temperature is preferably 5 to 60 ° C, more preferably 10 to 35 ° C.
• the extraction dehydration method is not particularly limited, but for example, a method using a continuous countercurrent contact tower is preferable.
• the packing for the continuous countercurrent contact tower is not particularly limited, but for example, Raschig ring, Lessing ring, Pole ring, Berle saddle, Interlock saddle, Terralet packing, Dixon ring, McMahon packing are preferable, and regular packing is Although not particularly limited, for example, a mesh-structured packing is preferable.
• Dehydrated acetonitrile is a mixture that may contain 75% by mass or more and 99% by mass or less of acetonitrile, 0% by mass or more and less than 25% by mass of water, and other impurities.
• the low boiling point and high boiling point removal step is a step of removing a low boiling component below the boiling point of acetonitrile and a high boiling point component exceeding the boiling point of acetonitrile from dehydrated acetonitrile to obtain a product acetonitrile described later.
• a low boiling point removal method and a high boiling point removal method For example, the method of using a distillation column is mentioned.
• Hydrous crude acetonitrile is a known method for distillation purification of by-product crude acetonitrile obtained as a by-product in the production of acrylonitrile or methacrylonitrile by the catalytic ammoxidation reaction of propylene or isobutene with ammonia and molecular oxygen. It is also possible to purify in the same manner as above or according to the distillation purification method. Although it does not specifically limit as a prior art used as a reference, For example, patent document 1, patent 3104312 gazette, WO2013 / 146609 pamphlet etc. can be mentioned.
• Process acetonitrile refers to acetonitrile having an acetonitrile content of more than 99% by mass and an impurity content other than acetonitrile of less than 1% by mass.
• the content of acetonitrile contained in the product acetonitrile is preferably 99.5 to 100% by mass, more preferably 99.9 to 100% by mass, and further preferably 99.99 to 100% by mass.
• the content of toluene in the product acetonitrile is preferably less than 1 ppm by mass, more preferably less than 0.5 ppm by mass, and even more preferably less than 0.1 ppm by mass with respect to 100% by mass of acetonitrile.
• the lower limit of the content of toluene contained in the product acetonitrile is not particularly limited, but is preferably not more than the detection limit, and more preferably 0% by mass with respect to 100% by mass of acetonitrile. When the content of toluene in the product acetonitrile is within the above range, higher quality acetonitrile is obtained.
• the absorbance of ultraviolet absorption at a wavelength of 200 nm of the product acetonitrile is preferably 0.3 or less, more preferably 0.25 or less, and further preferably 0.2 or less.
• the lower limit of the absorbance of ultraviolet absorption at a wavelength of 200 nm of the product acetonitrile is not particularly limited, and it is preferably as low as possible, more preferably 0.
• the absorbance of ultraviolet absorption at a wavelength of 200 nm is an indicator of the content of the aromatic compound in the product acetonitrile. From this point of view, when the absorbance of ultraviolet absorption at a wavelength of 200 nm of the product acetonitrile is within the above range, higher quality acetonitrile is obtained.
• Acetonitrile of this embodiment is obtained by the above production method.
• Acetonitrile thus obtained is a solvent for chemical reaction, particularly a pharmaceutical intermediate synthesis solvent, a purification solvent, a mobile phase solvent for high performance liquid chromatography, a DNA synthesis solvent and a purification solvent, and an organic EL material. It can be suitably used as a solvent for synthesis or as a cleaning solvent for electronic parts.
• acetonitrile of this embodiment is synonymous with product acetonitrile.
• Example 1 SAPO-34 powder (manufactured by JGC Universal Co., Olite Sample Kid, SiO 2 3 wt%, Al 2 O 3 43 wt%, P 2 O 5 53 wt%) was compression molded and then crushed to a size of 8-20 mesh The catalyst was classified. 3.12 g of the obtained catalyst was charged into a quartz glass reactor having an inner diameter of 20 mm ⁇ , and heated at an external electric furnace temperature of 490 ° C. while supplying nitrogen at 60 Ncc / min at normal pressure.
• Procedure 1 Concentration process A normal pressure continuous distillation of hydrous crude acetonitrile was performed using a glass Oldshaw distillation column having 20 plates under a reflux ratio of 20 to remove ammonia gas from the top of the column. Subsequently, the obtained ammonia gas-removed solution was redistilled in the same distillation column to obtain crude acetonitrile from the top of the column. The composition of the obtained crude acetonitrile was 64% by mass of acetonitrile, 35% by mass of water, and 1% by mass of other impurities.
• Procedure 2 Dehydration step The crude acetonitrile obtained in the concentration step was brought into countercurrent contact with a 48% aqueous sodium hydroxide solution using a Dixon packing packed column to obtain dehydrated acetonitrile.
• the composition of dehydrated acetonitrile was 98 mass% acetonitrile and 2 mass% water.
• Procedure 3 Low-boiling, high-boiling separation column Using a glass Oldshaw distillation column having 50 stages, by carrying out atmospheric pressure continuous distillation of dehydrated acetonitrile twice under the condition of a reflux ratio of 15, Removal of high-boiling substances and purification were performed to obtain a product acetonitrile.
• the composition of the product acetonitrile was 99.99 mass% acetonitrile and 0.01 mass% water.
• the toluene content in this product acetonitrile was below the gas chromatography detection limit (less than 0.1 ppm by mass with respect to 100% by mass of acetonitrile).
• SSZ-13 was synthesized as follows according to the synthesis method published by the International Zeolite Society (IZA). 1 molar sodium hydroxide (made by Wako Pure Chemicals, special grade) 32.0 g, N, N, N-trimethyladamantanammonium hydroxide (25 mass% solution) 13.5 g, aluminum hydroxide (Wako Pure Chemicals) 0.4 g and 4.80 g of fumed silica (manufactured by Nippon Aerosil Co., Ltd., AEROSIL OX50) were charged into a 200 mL autoclave, and hydrothermal synthesis was performed at 160 ° C. for 5 days.
• IZA International Zeolite Society
• the obtained zeolite slurry was filtered, washed with 1 L of ion exchange water and 200 mL of acetone (manufactured by Wako Pure Chemical Industries) and methanol (manufactured by Wako Pure Chemical Industries), then dried overnight at 120 ° C., and further a muffle furnace And calcined at 600 ° C. for 1 hour in an air atmosphere.
• SiO 2 / Al 2 O 3 (molar ratio) of the obtained zeolite was 21 derived from the Si and Al contents obtained by XRF measurement. Further, it was confirmed by XRD measurement that the obtained zeolite was SSZ-13.
• Example 2 A reaction was carried out in the same manner as in Example 1 except that the obtained SSZ-13 was used to obtain hydrous crude acetonitrile.
• Table 2 shows the composition analysis results and the detailed analysis results of the trace components.
• Example 1 A reaction was carried out in the same manner as in Example 1 except that H-MFI40 / alumina binder molded body catalyst manufactured by JGC Universal Co. was used as a catalyst to obtain hydrous crude acetonitrile.
• Table 3 shows the composition analysis results and the detailed analysis results of the trace components.
• acetonitrile obtained by concentrating, dehydrating and purifying the hydrated crude acetonitrile obtained in the present embodiment also contains no toluene.
• the present invention is an industrial process for producing high-purity acetonitrile from acetic acid and ammonia, which is used for the synthesis and purification of chemical solvents, especially pharmaceutical intermediates, or for the mobile phase solvent of high performance liquid chromatography.
• by-product formation of an aromatic compound in the obtained hydrous crude acetonitrile can be suppressed, which is useful as an industrial production method.

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