JP5916209B2 - Process for producing useful compounds from acetonitrile - Google Patents

Description

  The present invention relates to a method for producing an addition compound of acetonitrile to an aromatic compound.

  The cyano group generates a primary amine by a reduction reaction, and becomes a primary amide and further a carboxylic acid by hydrolysis. However, in order to introduce a cyano group into a compound, a method of reacting a highly toxic cyanate compound is mainly used, which is dangerous. Furthermore, even when an unreacted cyanide compound is discarded, a large amount of energy is required to render it harmless, and therefore it is desired to introduce a cyano group without using a cyanide compound.

  On the other hand, acetonitrile having a cyano group is widely used as an organic solvent for reaction because of its poor reactivity. Acetonitrile is much less toxic than cyanide, and if acetonitrile can be used to introduce a cyano group, the risk is much lower in the production of intermediates such as pharmaceuticals.

  However, due to the poor reactivity of acetonitrile, it seemed impossible to react acetonitrile with other compounds.

  Recently, it has been confirmed that phenylacetonitrile is produced by reacting acetonitrile and benzene using a photocatalyst. For example, Non-Patent Document 1 shows that benzene acetonitrile, succinonitrile, and the like are produced by suspending Pd-supported titanium oxide in a mixed solution of acetonitrile and benzene and irradiating with ultraviolet rays. However, this reaction is carried out for 3 hours under ultraviolet irradiation, and the production efficiency is poor, so it cannot be put to practical use.

The 108th Catalysis Conference Discussion Session A Proceedings 1H23

  Therefore, an object of the present invention is to provide a new process that can easily introduce a cyano group into an aromatic compound by increasing the reactivity of acetonitrile.

  As a result of intensive research to achieve the above object, the present inventor has irradiated acetonitrile while circulating a reaction solution containing acetonitrile and an aromatic compound through a microreactor channel, thereby adding acetonitrile-added fragrance such as phenylacetonitrile. A method for producing a group compound has been found. Further, the present inventors have found that the reaction efficiency is further improved by coexistence of a noble metal catalyst or a catalyst such as copper, cobalt, nickel, iron, etc., and the present invention has been completed.

  As the catalyst, simple metals such as gold, silver, platinum, palladium, ruthenium, rhodium, iridium, copper, cobalt, iron, nickel, oxides, metal complexes, nanoparticles, and mixtures thereof can be used. As the carrier, a general carrier such as titanium oxide, zeolite, silica, alumina or the like can be used.

  According to the method of the present invention, the reactivity of acetonitrile can be increased and a cyano group can be easily introduced into an aromatic compound.

1 is a schematic view of a microreactor reaction device preferably used in the present invention. 1 is a schematic view of a microreactor reaction device preferably used in the present invention.

  The method of the present invention relates to a method for producing an acetonitrile-added aromatic compound such as phenylacetonitrile by activating acetonitrile by irradiation while circulating a reaction solution containing acetonitrile and an aromatic compound in a microreactor channel. Hereinafter, preferred embodiments of the present invention will be described in detail. The following embodiment is merely an example of the present invention, and those skilled in the art can change the design as appropriate.

(Aromatic compounds)
The aromatic compound used in the present invention includes a benzene-based aromatic compound having at least one benzene ring in the molecule and having an unsubstituted site capable of introducing an acetonitrile group into the benzene ring. Here, the benzene aromatic compound is obtained by connecting an aromatic compound having a single benzene ring (hereinafter referred to as a monocyclic aromatic compound) and two or more benzene rings via a polyvalent group. An aromatic compound (hereinafter referred to as a polyvalent aromatic compound), an aromatic compound having two or more benzene rings in a condensed state (hereinafter referred to as a condensed cyclic aromatic compound), and two or more benzene rings Are directly linked aromatic compounds (hereinafter referred to as ring-aggregated aromatic compounds).

  Examples of the monocyclic aromatic compound include benzene, monosubstituted benzene, disubstituted benzene, and polysubstituted benzene. The substituent is not particularly limited, and may be substituted with a substituent containing various functional groups. Substituents include various linear and branched saturated or unsaturated hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, cyclic saturated and unsaturated hydrocarbon groups such as cycloalkyl groups, and hydroxy groups. A substituent having an oxygen-containing functional group such as a carbonyl group, an oxy group, a carboxyl group or an ester group, or a substituent having a nitrogen-containing functional group such as a cyano group or an imide group. Moreover, the substitution which has a heterocyclic functional group may be sufficient. These substituents include methyl, ethyl, propyl, butyl, carboxyl, nitro, amino, cyano, acetyl, alkoxy, hydroxyl, acetoxy, halogen, thioalkoxy, etc. Can be mentioned.

  Examples of such monocyclic aromatic compounds include benzene, toluene, ethylbenzene, styrene, xylene, propylbenzene, butylbenzene, cumene, cymene, benzoic acid, nitrobenzene, aniline, benzonitrile, acetophenone, anisole, phenol, catechol, and resorcinol. , Hydroquinone, phenyl acetate, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, cresol, chlorotoluene, benzyl chloride, nitrotoluene, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, benzaldehyde, benzenesulfonic acid, and toluenesulfonic acid Etc. Among them, a benzene derivative having an electron donating group such as benzene, alkylbenzene, aromatic hydroxy compound, aniline, anisole, chlorobenzene can be preferably used, and benzene and alkylbenzene are more preferable.

  Note that the monocyclic aromatic compound includes a compound having a hydrocarbon ring or a heterocyclic ring containing a conjugated ring other than benzene condensed or connected to a benzene ring. Examples of such monocyclic aromatic compounds include indene, benzothiophene, benzofuran, benzopyran, and quinosane.

  A polyvalent aromatic compound is a compound in which units containing a benzene ring or a benzene ring are linked via a divalent or higher polyvalent group such as an oxy group, an alkylene group, or an imino group. The polyvalent aromatic compound also includes a polymer compound in which a unit containing a benzene ring is connected as a monomer unit in a linear or branched manner. The polyvalent aromatic compound may have a substituent, and the substituent can have the same various substituents as in the monocyclic aromatic compound. Examples of such polyvalent aromatic compounds include diphenyl ether, dibenzyl ether, dibenzyl ketone, and dibenzyl.

  Examples of the polycyclic aromatic compound include a condensed ring aromatic compound and a ring assembly aromatic compound. Examples of the condensed ring aromatic compound include naphthalene, anthracene, triphenyline, and the like, or compounds having one or more substituents in these benzene rings. The substituent can have various substituents similar to those in the monocyclic aromatic compound. Examples of such fused ring aromatic compounds include naphthalene, naphthol, dihydroxynaphthalene, anthracene, triphenyline, benzophenanthrene, and the like.

  In addition, the ring-aggregated aromatic compound is a compound in which at least two benzene rings in a molecule are connected through a bond without having a shared atom. For example, a ring-assembled aromatic compound in which benzene rings such as biphenyl and terphenyl are linearly connected, a ring-assembled aromatic compound that is branched and connected, and one or more substituents in these benzene rings A compound can be mentioned. The substituent can have various substituents similar to those in the monocyclic aromatic compound. Examples of such ring-aggregated aromatic compounds include biphenyl, terephenyl, and stilbene.

  The aromatic compound of the present invention is sufficient if it has at least one benzene ring or non-benzene aromatic ring having an unsubstituted site into which an acetonitrile group can be introduced, and is not classified into the above categories or two. Compounds that are simultaneously classified into the above categories are also included.

  Benzene, phenol, toluene and naphthalene can be used as typical aromatic compounds in the present invention. In addition, these aromatic compounds may have a substituent and do not need to have a substituent.

(Acetonitrile)
In the present invention, acetonitrile which also serves as a reaction solvent is included. The amount of acetonitrile relative to the aromatic compound is preferably at least 2 times the molar amount, more preferably at least 10 times the molar amount relative to the aromatic compound.

(Reaction catalyst)
In the present invention, a catalyst may be added to the reaction solution and allowed to coexist during irradiation. Further, the reaction may be carried out by immobilizing a catalyst in a radiation transmitting region in the microreactor channel. Catalysts that can be used in the present invention include, but are not limited to, homogeneous catalysts, nanoparticle catalysts, and carrier-immobilized catalysts (hereinafter simply referred to as “supported catalysts”). Details of the catalyst used in the present invention are shown below.

<Uniform catalyst>
In the present invention, together with the reaction solution, the reaction may be carried out by irradiating with radiation while a homogeneous catalyst dissolved in a solvent is circulated through the microreactor. As the homogeneous catalyst, metal salts and metal complexes of Periodic Tables Group 5 to 11 can be used. For example, a gold compound, a silver compound, a platinum compound, a palladium compound, a rhodium compound, a ruthenium compound, an iridium compound, a cobalt compound, a copper compound, a nickel compound, an iron compound, and a mixture thereof can be used. Specifically, cobalt acetate, cobalt nitrate, copper acetate, copper nitrate, palladium acetate, palladium nitrate, silver chloride, ruthenium chloride, rhodium chloride metal salt, tetraammine palladium nitrate, hexaammine platinum (II) salt, hexachloroplatinum (IV ) Metal complexes such as acid salts and tetrachlorogold (III) acid salts can be used.

  Here, the concentration of the homogeneous catalyst in the reaction solution is less than 1% by weight, preferably less than 0.1% by weight as a metal or a noble metal based on the weight of the reaction solution.

<Nanoparticle catalyst>
In the present invention, the reaction may be carried out by irradiating with radiation while mixing a precious metal or metal nanoparticles in a solvent together with the reaction solution and circulating it through the microreactor. As the nanoparticles, periodic table types 5 to 11 metals or metal oxides, and mixtures thereof can be used. For example, gold, silver, platinum, palladium, rhodium, ruthenium, iridium, cobalt, copper, nickel, iron, and oxides thereof can be used alone or in combination. The particle size of the nanoparticles is not particularly limited, but those having a particle size of 50 nm or less, specifically 30 nm or less, and more specifically having a particle size of 10 nm or less are preferable because of high activity. The particle size of the nanoparticles can be measured by an electron microscope or a dynamic light scattering method.

  Here, the concentration of the nanoparticles in the reaction solution is less than 1% by weight, preferably less than 0.1% by weight as a metal or noble metal based on the weight of the reaction solution.

  The method for producing the metal nanoparticle catalyst is not particularly limited, but can be produced by a normal reduction method or the like. For example, there are a method of reducing by adding a reducing agent to the aqueous metal salt solution, a method of adding a weak reducing agent such as alcohol to the aqueous metal solution and reducing with reflux. At this time, a dispersant such as polyvinylpyrrolidone may be added to the metal aqueous solution.

  The method for producing metal oxide nanoparticles is not particularly limited, but can be produced by a normal oxidation method or the like. For example, a method of forming a metal oxide by adding an oxidizing agent such as ozone to a metal aqueous solution, a hydroxide by adding an alkaline aqueous solution to a metal salt aqueous solution, drying, and then firing and oxidizing in air There is a method in which a product is formed and further pulverized to a nanoparticle size by a nanoparticle pulverizer such as a bead mill. When oxidizing in solution, a dispersant such as polyvinylpyrrolidone may be added to the aqueous metal salt solution.

<Supported catalyst>
Furthermore, in this invention, you may carry | support the catalyst containing a metal or a metal, and these oxides on a support | carrier. By supporting the carrier, the operability is improved and it can be used for a wider range of applications.

  As the catalyst to be supported, simple metals, oxides, and mixtures of metals of Periodic Tables Group 5 to Group 11 can be used. Preferably, simple metals such as gold, silver, platinum, palladium, ruthenium, rhodium, iridium, cobalt, copper, nickel and iron, oxides, and mixtures thereof can be used.

  Further, the metal or metal oxide catalyst supported on the support may be particles. The particle size of the metal or metal oxide particles is not particularly limited, but those having a particle size of 50 nm or less, specifically 30 nm or less, more specifically 10 nm or less are preferred because of high activity. As the metal or metal oxide particles, the above nanoparticle catalyst may be used. The particle size of the metal particles or metal oxide particles can be measured by an electron microscope or carbon monoxide and hydrogen adsorption method.

The carrier of the supported catalyst according to the present invention is not particularly limited, but it is preferable to use a substance having a large specific surface area. When the specific surface area is large, even if the loading amount of the metal nanoparticles is increased, the distance between the particles is large, so that it is possible to prevent the particles from being bonded to increase the particle diameter. The carrier preferably has a specific surface area of 50 m ² / g or more, and more preferably 100 m ² / g or more. The shape of the carrier is not particularly limited, but may vary depending on the use form described in detail below.

  As the support of the supported catalyst of the present invention, silica, alumina, silica alumina, silica titania, zeolite, titanium oxide, iron oxide, copper oxide, mesoporous silica, mesoporous titania, tungsten oxide, niobium oxide, carbon nitride, porous silica, Inorganic compounds such as porous titania, zirconia, ceria, activated carbon, carbon black, carbon nanotube, and carbon nanofiber can be used. Furthermore, compounds obtained by adding other elements to the main component constituting these carriers can also be used.

  The amount of metal particles or metal oxide particles supported on the carrier is not particularly limited. For example, the amount of gold particles supported on titanium oxide is 0.01 to 10.0% by weight based on titanium oxide. It is preferable that it is 0.1 to 2.0 weight%. Further, the amount of platinum supported on the zeolite is preferably 0.01 to 10.0% by weight, more preferably 0.1 to 2.0% by weight based on the zeolite.

  The metal particle-supported catalyst used in the present invention is not particularly limited, but can be produced by a usual method. For example, a method of impregnating a metal ion on a support and then suspending in a solution containing a reducing agent such as sodium borohydride to reduce, or a method of impregnating a metal ion on a support and then drying the hydrogen ion Among them, there is a method of reducing treatment. Alternatively, separately produced metal nanoparticles or metal oxide nanoparticles can be supported on a carrier and used as a metal particle supported catalyst or a metal oxide supported catalyst.

(Other ingredients)
In addition, in the method of this invention, another component can be included in the range which does not interfere with the objective of this invention. For example, it can also be included in a range not involving the generation or increase of by-products such as inorganic acids and inorganic alkalis. Moreover, in order to improve the dispersibility of the catalyst particles in the reaction solution, a dispersant may be added.

(Acetonitrile addition aromatic compound)
The acetonitrile-added aromatic compound obtained by the method of the present invention is a compound in which at least one acetonitrile group is bonded directly to carbon forming the benzene ring of the aromatic compound. According to the method of the present invention, the aromatic compound is a compound in which at least one of the carbon-hydrogen bonds in the carbon forming the benzene ring is converted to a carbon-acetonitrile bond. For example, phenylacetonitrile is produced from benzene, and methylbenzeneacetonitrile is produced from toluene.

(Reaction process using microreactor channel)
Next, the process of the present invention will be described. In the present invention, acetonitrile is activated by radiation irradiation while a mixture of acetonitrile and an aromatic compound is used as a reaction solution in a microreactor flow path to produce an acetonitrile-added aromatic compound such as phenylacetonitrile.

  In the present invention, “radiation” refers to a particle beam or electromagnetic wave having high ionizing energy. Specifically, gamma rays and electron beams are preferred because of their high permeability and high reactivity with compounds. When using a low energy electron beam (less than 200 keV), since the transmission power of the electron beam is very weak, it is preferable to react in a microreactor channel having a depth of less than 100 μm.

  In one embodiment of the present invention, the catalyst may be added to the reaction solution, or the catalyst may be immobilized in a radiation transmission region in the microreactor channel.

  When a catalyst is added to the reaction solution and allowed to flow through the microreactor flow path, a metal salt or a metal complex can be dissolved in the reaction solution and used as the catalyst. Further, a metal particle nanoparticle, a metal oxide particle nanoparticle catalyst, or a catalyst in which a metal particle or metal oxide particle catalyst is supported on a carrier having a particle size of 20 μm or less may be added to the reaction solution. The catalyst after the reaction can be separated from the reaction solution by distillation, filtration, centrifugation or the like and reused.

  In addition, a metal particle nanoparticle, a metal oxide particle nanoparticle catalyst, or a catalyst in which a metal particle or metal oxide particle is supported on a carrier may be fixed to the wall surface of the microreactor channel and the reaction solution may be circulated. . The carrier in this case is preferably in the form of particles having a particle size of 10 μm or less, but is not particularly limited. The immobilization of the catalyst in the microreactor channel is not particularly limited, but can be immobilized using an inorganic binder. As the inorganic binder, ceramic sols such as alumina sol and silica sol are preferable. The ceramic sol and the catalyst can be mixed and applied to the surface of the flow path, and then heated at a temperature of 200 ° C. or higher for immobilization. As the heat treatment temperature, it is necessary to select a temperature at which the inorganic binder is fixed. Depending on the catalyst, the noble metal particles may be further reduced in a reducing atmosphere after being immobilized on the microreactor channel with an inorganic binder.

  An example of a microreactor reaction apparatus preferably used in the present invention is shown in FIG. In FIG. 1, the microreactor reaction apparatus includes pump units 1 a and 1 b, a microreactor channel unit 2, a radiation irradiation unit 3, a Peltier temperature control unit 4, a channel cover 5, and a channel cover holder 6. A reaction solution containing acetonitrile and an aromatic compound is introduced into the microreactor channel section 2 from the pump sections 1a and 1b. At this time, the inlet of the microreactor channel may be Y-shaped, and acetonitrile and the aromatic compound may be introduced from separate channels. Further, the reaction solution may be introduced into the microreactor channel section 2 from one pump section (not shown).

  The flow path cover 5 is preferably a metal thin film having a thickness of 10 μm or less so that a low energy electron beam can be transmitted. Titanium, beryllium, aluminum, stainless steel or the like can be used as the metal type, but is not particularly limited. If the radiation resistance is strong, a resin such as Kapton may be used. However, in the case of a resin, it is necessary to regularly check for radiation damage.

  The Peltier-type temperature control unit 4 is used to suppress the temperature of the microreactor channel unit 2 from rising due to radiation irradiation or to control to a specific reaction temperature. The radiation irradiated from the radiation irradiation unit 3 may be linear or may be diffused radially. In addition, by installing the Peltier temperature control unit 4 and the microreactor flow path unit 2 on the X and Y stages and moving the X and Y stages, the entire microreactor flow path unit 2 can be irradiated with radiation. Good.

  The reason why the yield and selectivity are improved when such a process of the present invention is used is not clear, but the present inventors infer as follows.

  In the microreactor, acetonitrile is activated by irradiation with radiation to generate acetonitrile radicals. Next, the acetonitrile radical reacts with the aromatic compound to produce an acetonitrile-added aromatic compound. As a result, when the aromatic compound is benzene, phenylacetonitrile is produced.

  EXAMPLES Hereinafter, although this invention is demonstrated more concretely based on an Example and a comparative example, this invention is not limited to a following example.

(Synthesis of phenylacetonitrile)
Examples 1-4, Comparative Example 1
To a 100 ml volumetric flask, 0.5 mg of benzene and 50 mg of metal salt powder or metal complex powder were added as catalysts, and when the solubility of the metal salt was low, 1 ml of diluted hydrochloric acid (1 + 10) was additionally added. Acetonitrile was added to the volumetric flask to a total volume of 100 ml. Using this as a reaction solution, the reaction was carried out in an electron beam assisted microreactor.

  As the electron beam irradiation apparatus, EB-ENGENE (registered trademark) manufactured by Hamamatsu Photonics was used, and the flow path of the microreactor was set at a distance of 20 mm from the irradiation window. The channel had a width of 500 μm, a depth of 100 μm, and a length of 79 mm. The microreactor channel was covered with a 3 μm thick titanium foil. The temperature of the microreactor channel was controlled to 20 ° C. with a Peltier device. An electron beam was irradiated while the reaction solution was allowed to flow through the microreactor flow path at 0.05 ml / min. Table 1 shows the type of each catalyst, the amount of dilute hydrochloric acid added, and the electron beam irradiation conditions.

Examples 5-9
To a 100 ml volumetric flask, 0.5 ml of benzene and 1 ml of an aqueous metal salt solution or an aqueous metal complex solution were added as a catalyst, and acetonitrile was added to a total of 100 ml. Using this as a reaction solution, the reaction was carried out in an electron beam assisted microreactor.

  As the electron beam irradiation apparatus, EB-ENGENE (registered trademark) manufactured by Hamamatsu Photonics was used, and the flow path of the microreactor was set at a distance of 20 mm from the irradiation window. The flow path had a width of 500 μm, a depth of 100 μm, and a length of 79 mm. The microreactor channel was covered with a 3 μm thick titanium foil. The temperature of the microreactor channel was controlled to 20 ° C. with a Peltier device. An electron beam was irradiated while the reaction solution was allowed to flow through the microreactor flow path at 0.05 ml / min. Table 2 shows the type of each catalyst, the amount of dilute hydrochloric acid added, and the electron beam irradiation conditions.

Analysis example 1
Qualitative and quantitative analysis of phenylacetonitrile was performed by gas chromatography (apparatus: Shimadzu GC-2001, column: ZB-5, 0.25 mm × 30 m) by adding naphthalene as an internal standard to each reaction solution after completion of the reaction. It was. However, the conversion ratio of benzene to phenylacetonitrile was calculated by the following formula from the concentration of phenylacetonitrile in the reaction solution and the initial benzene concentration. Table 3 shows the results of qualitative and quantitative analysis.

  Conversion to phenylacetonitrile (%) = (phenylacetonitrile concentration (mol / L)) / (initial benzene concentration (mol / L)) × 100

  As shown in Table 3, it was confirmed that acetonitrile was added to the aromatic compound by irradiation with an electron beam in the microreactor.

DESCRIPTION OF SYMBOLS 1a Pump part 1b Pump part 2 Microreactor flow path part 3 Radiation irradiation part 4 Peltier temperature control part 5 Flow path cover 6 Flow path cover presser

Claims (10)

(1) providing a reaction solution containing (a) acetonitrile and (b) an aromatic compound;
(2) introducing the reaction solution into a microreactor;
(3) irradiating the reaction solution in the microreactor with gamma rays or electron rays to add acetonitrile to the aromatic compound;
A method for producing an acetonitrile-added aromatic compound, comprising: (1) providing a reaction solution comprising (a) acetonitrile, (b) an aromatic compound, and (c) a metal catalyst;
(2) introducing the reaction solution into a microreactor;
(3) irradiating the reaction solution in the microreactor with gamma rays or electron rays to add acetonitrile to the aromatic compound;
A method for producing an acetonitrile-added aromatic compound, comprising:   The method according to claim 1, wherein a metal catalyst or a noble metal catalyst is immobilized in the microreactor.   4. The catalyst according to claim 3, wherein the catalyst is selected from the group consisting of metal particles or metal oxide particles, a catalyst having metal particles or metal oxide particles supported on a support, and a mixture thereof. the method of.   The catalyst is selected from the group consisting of metal salts, metal complexes, metal particles or metal oxide particles, or a catalyst having metal particles or metal oxide particles supported on a support, and a mixture thereof. The method according to claim 2.   6. The catalyst according to claim 2, wherein the catalyst is selected from the group consisting of a metal simple substance, an oxide, a metal salt, or a metal complex of a metal belonging to the fifth to eleventh classes, or a mixture thereof. The method according to any one of the above.   The metal belonging to the fifth to eleventh classes is composed of platinum, palladium, ruthenium, rhodium, iridium, rhenium, gold, silver, copper, nickel, cobalt, iron, chromium, manganese, niobium, molybdenum, tungsten. The method according to claim 6, wherein the metal is at least one selected metal.   The metal particles or metal oxide particles are silica, alumina, silica alumina, silica titania, zeolite, titanium oxide, iron oxide, copper oxide, mesoporous silica, mesoporous titania, tungsten oxide, niobium oxide, carbon nitride, porous silica, 8. It is supported on at least one carrier selected from the group consisting of porous titania, zirconia, ceria, activated carbon, carbon black, carbon nanotubes, and carbon nanofibers. The method described in 1.   The catalyst is tetraamminepalladium (II) salt, tetrachloropalladium (II) acid salt, hexachloropalladium (IV) acid salt, palladium nitrate (II), palladium acetate (II), tetraammineplatinum (II) salt, tetrachloroplatinum (II) acid salt, hexachloroplatinum (IV) acid salt, rhodium chloride, rhodium acetate, hexaamminerhodium (III) salt, ruthenium chloride, hexachlororuthenium (IV) acid salt, ruthenium acetate, ruthenium nitrate, tetrachlorogold ( III) acid salt, hexachloroiridium (IV) acid salt, hexachloroiridium (III) acid salt, silver nitrate, cobalt acetate, cobalt nitrate, cobalt chloride, copper acetate, copper nitrate, copper chloride, nickel acetate, nickel nitrate, nickel chloride, Must be iron acetate, iron nitrate, and iron chloride The method according to any one of claims 4 to 8, characterized.   The method according to any one of claims 1 to 9, wherein the aromatic compound is benzene and the product is phenylacetonitrile.

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