Method for producing hydrogenation reactant and mechanochemical reactor

Abstract

To provide a manufacturing method of a hydrogenated product capable of performing a hydrogenation reaction at a high conversion rate and with safety and a mechanochemical reactor.SOLUTION: A method for producing a hydrogenated product comprises: a process in which a hydrogenation reaction of an object to be hydrogenated is performed by a mechanochemical method due to a relative motion between a reaction vessel and a plurality of balls charged in the reaction vessel in a reactor provided with the reaction vessel and the balls, wherein the hydrogenation reaction is performed in the presence of a hydrocarbon, and each ball has a mass of 2 g or more.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a method for producing a hydrogenation reactant and a mechanochemical reactor. [Background technology]

[0002] Conventionally, hydrogenation reactions of organic compounds have been widely used in organic synthetic chemistry, and many useful compounds are produced by this method. There are many known methods for hydrogenation reactions, such as reactions using alkali metals, reactions using metal hydrides or metal hydrogen complexes, reactions using diborane or hydrazine, and reactions using catalytic hydrogenation.

[0003] However, when alkali metals, metal hydrides, metal hydrogen complexes, diborane, hydrazine, etc. are used in the above hydrogenation reactions, the cost and danger of the reaction reagents used are often high. In addition, even in the method using catalytic hydrogenation, it is necessary to use a special metal catalyst, and the versatility is low.

[0004] Mechanochemical reactions are reactions that utilize the fact that when various mechanical energies (compression, shear, impact, grinding, etc.) are applied to raw material components, the substances become active and their physicochemical properties change. In recent years, mechanochemical reactions have been developed as a method for synthesizing compounds that does not use solvents to dissolve the raw material components, and a hydrogenation reaction technology that utilizes mechanochemical reactions has also been proposed (Patent Publication No. 6334173, Org. Lett. 2018, 20, 2892-2896). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 6334173 [Non-patent literature]

[0006] [Non-Patent Document 1] Org. Lett. 2018, 20, 2892-2896 Summary of the Invention [Problem to be solved by the invention]

[0007] However, conventional technologies have problems in that they do not have the reducing power to hydrogenate aromatic nuclei, instead of using safe water as a hydrogen source (Patent Document 1), or they can partially reduce aromatic nuclei but require diethyl ether, which has the lowest flash point among Class 4 hazardous materials (Non-Patent Document).

[0008] An object of the present invention is to provide a method for producing a hydrogenation reactant and a mechanochemical reaction apparatus which can carry out a hydrogenation reaction safely with a high conversion rate. [Means for solving the problem]

[0009] As a result of intensive research, the present inventors have found that the above problems can be solved by adopting the following configuration, and have completed the present invention.

[0010] In one embodiment, the present invention comprises: A method for producing a hydrogenation reactant, comprising the steps of: The method includes a step of carrying out a hydrogenation reaction of a substance to be hydrogenated by a mechanochemical method using relative motion between a reaction vessel and a plurality of balls placed in the reaction vessel in a reaction apparatus, the reaction vessel and the balls being disposed in the reaction vessel, The hydrogenation reaction is carried out in the presence of a hydrocarbon, The present invention relates to a method for producing a hydrogenation reactant, wherein the mass of each of the balls is 2 g or more.

[0011] According to the method for producing a hydrogenation product, the hydrogenation reaction of the material to be hydrogenated can be carried out safely with a high conversion rate. The reason for this is unclear, but is presumed to be as follows. The inventors of the present invention have conducted various studies on the source of hydrogen used in hydrogenation and the mechanochemical reaction apparatus, and have unexpectedly found that high hydrogenation capacity can be achieved even when a hydrocarbon is used as the hydrogen source by using balls of a predetermined mass or more. Furthermore, by using a plurality of balls of a predetermined mass in the mechanochemical reaction, the reaction energy required for the hydrogenation reaction can be efficiently imparted to the reaction system, and as a result, the hydrogenation of the material to be hydrogenated can be carried out with a high conversion rate.

[0012] In one embodiment, the present invention comprises: A mechanochemical reaction apparatus comprising a reaction vessel and a plurality of balls inserted into the reaction vessel, the reaction vessel and the balls moving relative to each other, The present invention relates to a mechanochemical reaction device in which the mass of each of the balls is 2 g or more.

[0013] The mechanochemical reaction apparatus is equipped with a plurality of balls of a predetermined mass, and therefore can safely carry out the hydrogenation reaction of the material to be hydrogenated by the mechanochemical method with a high conversion rate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] <<Method for Producing Hydrogenation Reactant>> The method for producing a hydrogenation product according to the present embodiment includes a step of performing a hydrogenation reaction of a material to be hydrogenated by a mechanochemical method using relative motion between a reaction vessel and a plurality of balls placed in the reaction vessel in a reaction apparatus (hereinafter, also referred to as a "hydrogenation reaction step"). The reaction apparatus and the hydrogenation reaction conditions will be described below in order.

[0015] (Reaction Apparatus) The hydrogenation reaction by the mechanochemical method is a reaction that is carried out by increasing the activity of the material to be hydrogenated by mechanical energy such as impact and friction. A mechanochemical reaction apparatus that can be used in the hydrogenation reaction process includes a reaction vessel and a plurality of balls placed in the reaction vessel. In the reaction vessel, mechanical energy is imparted to the components in the reaction vessel by the relative motion between the reaction vessel and the balls, and the material to be hydrogenated can be hydrogenated. The reaction vessel performs a reciprocating motion, a rotational motion, a combination of these motions, or any other arbitrary motion, and the balls in the reaction vessel perform a corresponding motion, thereby generating a relative motion between the two.

[0016] Examples of reaction apparatuses that generate the relative motion include reciprocating mixer mills, planetary ball mills, rotary ball mills, etc. Among these, it is preferable to use a reciprocating mixer mill in which a reaction vessel and a ball perform a reciprocating relative motion, or a planetary ball mill in which a reaction vessel and a ball perform a rotary relative motion, from the viewpoints of stirring efficiency and applied energy.

[0017] As described above, the reaction apparatus includes a reaction vessel body and a plurality of balls. The reaction apparatus may further include an atmosphere control section, a heating device, and a cooling device. The procedure for carrying out the hydrogenation reaction step is to first put the starting material to be hydrogenated, a hydrocarbon as a hydrogen generating source, and a plurality of balls as a stirring medium into the reaction vessel. Next, the reaction vessel is set in a device that generates a predetermined motion in the reaction vessel, and then the reaction vessel is moved in the atmosphere control section as necessary. In a reciprocating mixer mill, the reaction vessel moves back and forth, and in a planetary ball mill, the reaction vessel rotates and revolves around its axis in a motion similar to that of a planet, causing relative motion between the reaction vessel and the balls, and impacts are applied to the contents of the reaction vessel. When the reaction apparatus includes an atmosphere control section, the reaction can proceed in an inert atmosphere, for example, and therefore it is also applicable to components that would be altered in air.

[0018] The number of balls is not particularly limited as long as it is more than one, and may be 2, 3, 4, 5 or more. It can be appropriately set depending on the reaction efficiency and reaction scale.

[0019] The mass of each ball in the reaction apparatus is 2 g or more. The mass of each ball can be set according to the mechanical energy required for the hydrogenation reaction and the scale of the reaction system. The lower limit of the mass may be 3 g, 4 g, 5 g, 10 g, 12 g, or 14 g. The upper limit of the mass may be 1000 g, 800 g, 500 g, 100 g, 50 g, or 40 g. The upper limit may be a value exceeding these. The multiple balls may have the same mass or different masses. From the viewpoint of reaction homogeneity, it is preferable that the multiple balls have substantially the same mass. Substantially the same means that the difference between the average mass of the multiple balls and the mass of the target ball is within ±5% of the average mass in terms of mass ratio.

[0020] It is preferable that the reaction vessel and the balls, in part or in whole, each independently contain at least one material selected from the group consisting of stainless steel, agate, alumina, tungsten carbide, chromium steel, zirconia, silicon nitride, brass, and Teflon (registered trademark). Among these materials, stainless steel and tungsten carbide are preferable. It is preferable that the reaction vessel and the balls, in part or in whole, are formed of the above material. It is preferable that at least the outermost layer of the reaction vessel and the balls are formed of the same material.

[0021] The diameter of the ball is not particularly limited as long as the above-mentioned mass per ball can be obtained, and can be appropriately set within the range of 0.1 mm to 100 mm depending on the material of the ball and the size of the reaction vessel.

[0022] The capacity of the reaction vessel is not particularly limited, but can be appropriately set within the range of 1 mL or more and 50,000 mL or less.

[0023] Specific examples of reaction apparatuses include a reciprocating mixer mill, such as Mixer Mill MM400 (manufactured by Retsch, Germany), and planetary ball mills, such as Planetary Ball Mill Quartet P-7 (manufactured by Fritsch, Germany), Planetary Ball Mill Premium Line-7 (manufactured by Fritsch, Germany), Planetary Ball Mill PM-100 (manufactured by Retsch, Germany), and Planetary Ball Mill Hi-G (manufactured by Kurimoto, Japan).

[0024] (Hydride)

[0025] The material to be hydrogenated is not particularly limited as long as it is an organic compound that can be hydrogenated, and examples of such materials include organic compounds having unsaturated bonds such as double bonds and triple bonds, highly oxidized substituents such as aldehyde groups, ketone groups, nitro groups and azide groups, halogens, etc. in their skeletons. By carrying out a hydrogenation reaction of these materials to be hydrogenated, it is possible to convert unsaturated bonds (double bonds or triple bonds) in the skeleton of the material to be hydrogenated into saturated bonds, convert highly oxidized substituents (aldehyde groups, ketone groups, nitro groups) into substituents with low oxidation degrees (hydroxyalkyl groups, hydroxy groups, amino groups), and remove halogens from halides to produce dehalogenated products.

[0026] Specifically, compounds having the following basic skeletons can be hydrogenated to produce the corresponding reduced products (hydrogenation reactants). Among these compounds, methyl groups are listed as representative of alkyl groups (functionalized fatty chains), and benzene or phenyl are listed as representative of aryl groups [functionalized aromatic rings (including benzene, furan, pyrrole, thiophene, etc.)].

[0027] <Triple bond-containing compounds> Terminal alkynes: methylacetylene, ethynylbenzene 2-substituted alkynes: diphenylacetylene, dimethylacetylene, methylphenylacetylene

[0028] <Double bond-containing compounds> 1-Substituted alkenes: phenylethylene, methylethylene 2-Substituted alkenes: (E)-1,2-diphenylethylene, (Z)-1,2-diphenylethylene, (E)-1,2-dimethylethylene, (Z)-1,2-dimethylethylene, 1,1-diphenylethylene, 1,1-dimethylethylene, 1-methyl-1-phenylethylene, (E)-1-methyl-2-phenylethylene, (Z)-1-methyl-2-phenylethylene 3-substituted alkenes: 1,1,2-triphenylethylene, 1,1,2-trimethylethylene, 1,1-diphenyl-2-methylethylene, 1-phenyl-1,2-dimethylethylene 4-substituted alkenes: 1,1,2,2-tetraphenylethylene, 1,1,2,2-tetramethylethylene, 1,1,2-triphenyl-2-methylethylene, 1,1-diphenyl-2,2-dimethylethylene, 1-phenyl-1,2,2-trimethylethylene, (E)-1,2-diphenyl-1,2-dimethylethylene, (Z)-1,2-diphenyl-1,2-dimethylethylene Aromatic ring: benzene, toluene, biphenyl, pyridine, furan, pyrrole, thiophene, naphthalene, quinoline, anthracene, imidazole, indole, benzofuran, oxazole

[0029] <Carbonyl group-containing compounds*> Aldehydes: methyl aldehyde, phenyl aldehyde Ketone bodies: dimethyl ketone, diphenyl ketone, methyl phenyl ketone Imines: N-methyl-methylimine, N-phenyl-methylimine, N-methyl-dimethylimine, N-methyl-diphenylimine, N-methyl-methylphenylimine, N-phenyl-dimethylimine, N-phenyl-diphenylimine, N-phenyl-methylphenylimine, Oximes: N-hydroxy-methylimine, N-hydroxy-dimethylimine, N-hydroxy-diphenylimine, N-hydroxy-methylphenylimine *: Includes those in which the oxygen atom of the carbonyl group has been replaced with other atoms or groups.

[0030] <Nitro group-containing compounds> Nitro form: nitromethane, nitrobenzene, N,N-bis(4-nitrophenethyl)adipamide

[0031] <Nitrile group-containing compounds> Nitriles: acetonitrile, benzonitrile

[0032] <Azide group-containing compounds> Azides: azidomethane, azidobenzene

[0033] <Halogen-containing compounds> Fluorine: methyl fluoride, fluorobenzene Chloroform: methyl chloride, chlorobenzene Bromo compounds: methyl bromide, bromobenzene Iodine forms: methyl iodide, iodobenzene

[0034] <Benzyl ether group-containing compound> Benzyl ether: phenylmethyloxymethane, phenylmethyloxybenzene

[0035] (Hydrogenation Reactant) Hydrogenation reactions are roughly divided into those in which a functional group as a substituent is hydrogenated (hydrogen substitution) and those in which a skeleton (nucleus) is hydrogenated. Preferred specific examples of the product to be hydrogenated and its reduced product, the hydrogenation reactant, are shown in Table 1. [Table 1]

[0036] (Hydrocarbons) The hydrogen reaction step is carried out in the presence of a hydrocarbon as a hydrogen generating source. By using mechanical energy by the mechanochemical method and, if necessary, by allowing a metal having catalytic action to coexist, hydrogen can be efficiently extracted from the hydrocarbon and used for the hydrogenation reaction. The hydrocarbon is not particularly limited, and any type of hydrocarbon, such as saturated and unsaturated hydrocarbons, aliphatic hydrocarbons, and aromatic hydrocarbons, can be used. From the viewpoint of efficiency of the hydrogenation reaction of the material to be hydrogenated, the hydrocarbon is preferably a saturated hydrocarbon. As the saturated hydrocarbon, either a chain-like saturated hydrocarbon or a cyclic saturated hydrocarbon can be suitably used, and a chain-like or cyclic saturated hydrocarbon having 6 to 12 carbon atoms is more preferable. Examples of the chain-like saturated hydrocarbon having 6 to 12 carbon atoms include hexane, heptane, octane, nonane, and decane. Examples of the cyclic saturated hydrocarbon having 6 to 12 carbon atoms include cyclohexane, cycloheptane, cyclooctane, cyclononane, and cyclodecane. The hydrocarbon may be used alone or in combination of two or more kinds.

[0037] The lower limit of the blending ratio of the hydrocarbon to 1 equivalent of the material to be hydrogenated is preferably 4 equivalents, more preferably 6 equivalents, even more preferably 8 equivalents, and particularly preferably 10 equivalents. The upper limit of the blending ratio is preferably 30 equivalents, more preferably 26 equivalents, even more preferably 22 equivalents, and particularly preferably 20 equivalents. By setting the blending ratio of the hydrocarbon within the above range, the hydrogenation reaction of the material to be hydrogenated can be efficiently carried out.

[0038] (metal) In the hydrogenation reaction step, it is preferable to carry out the hydrogenation reaction in the presence of at least chromium and nickel, since the hydrogenation reaction can proceed more efficiently by using these metals as catalysts.

[0039] When the hydrogenation reaction is carried out in the presence of chromium and nickel, the lower limit of the mixing ratio of chromium and nickel relative to 1 equivalent of the material to be hydrogenated is preferably 10 equivalents, more preferably 15 equivalents, even more preferably 20 equivalents, and particularly preferably 25 equivalents. The upper limit of the mixing ratio is preferably 100 equivalents, more preferably 80 equivalents, even more preferably 60 equivalents, and particularly preferably 50 equivalents.

[0040] It is preferable that the amount A of chromium present and the amount B of nickel present satisfy A≧B on a molar basis. The amounts of these metals present satisfying the above relationship allows the hydrogenation reaction to proceed more efficiently. It is preferable to set the blending ratios of chromium and nickel so as to satisfy the relationship of the amounts present from the ranges of the blending ratios of chromium and nickel described above. It is preferable that the amount A of chromium present and the amount B of nickel present satisfy A≧1.2B on a molar basis, more preferably A≧1.5B, even more preferably A≧1.8B, and particularly preferably A≧2.0B.

[0041] The hydrogenation reaction may be carried out in the presence of at least one metal selected from the group consisting of palladium and platinum together with or instead of chromium and nickel. Palladium and platinum can be mixed depending on the type of the material to be hydrogenated and the reaction energy required for hydrogenation. When the hydrogenation reaction is carried out in the presence of at least one metal selected from the group consisting of palladium and platinum, the lower limit of the mixing ratio of the metal to 1 equivalent of the material to be hydrogenated is preferably 0.001 equivalent, more preferably 0.01 equivalent, even more preferably 0.02 equivalent, and particularly preferably 0.04 equivalent. The upper limit of the mixing ratio is preferably 1 equivalent, more preferably 0.5 equivalent, even more preferably 0.1 equivalent, and particularly preferably 0.08 equivalent, each independently.

[0042] The above metals as catalysts may be introduced into the reaction vessel used in the mechanochemical reaction in the form of powder, wire, foil, etc., or may be included in the material constituting the stirring medium such as the reaction vessel or ball used in the mechanochemical reaction, or may be added as plating on the surface of the stirring medium, or may be added in a combination of these forms. From the viewpoint of efficiency of the hydrogenation reaction, it is preferable to introduce the above metals into the reaction vessel as powder. The average particle size of the metal powder is not particularly limited and can be set in the range of 10 μm to 500 μm.

[0043] The reaction time of the hydrogenation reaction may be appropriately set so as to obtain a desired conversion rate. When a functional group as a substituent of the product to be hydrogenated is hydrogenated (hydrogen substitution), the lower limit of the reaction time is preferably 0.5 hours, more preferably 1 hour, and more preferably 2 hours. The upper limit of the reaction time is preferably 10 hours, more preferably 8 hours, and more preferably 5 hours. When the skeleton (core) of the product to be hydrogenated is hydrogenated, the lower limit of the reaction time is preferably 1 hour, more preferably 2 hours, and more preferably 4 hours. The upper limit of the reaction time is preferably 30 hours, more preferably 20 hours, and more preferably 15 hours.

[0044] The motion speed of the reaction vessel that generates the predetermined relative motion can be appropriately set depending on the impact (reaction energy) required for the hydrogenation reaction. When the reaction vessel and the ball perform a reciprocating relative motion, the motion speed is preferably 10 Hz to 60 Hz, more preferably 20 Hz to 50 Hz. When the reaction vessel and the ball perform a rotational relative motion (including planetary type), the revolution speed is preferably 100 rpm to 2000 rpm, more preferably 200 rpm to 1500 rpm.

[0045] In the hydrogenation reaction step, heating or pressurization from outside the reaction system may be appropriately performed, but it is preferable to perform the hydrogenation reaction without either or both of heating and pressurization from outside the reaction system, and it is more preferable to perform the hydrogenation reaction without both heating and pressurization. Since the production method utilizes a hydrogenation reaction by a mechanochemical method, a high conversion rate can be achieved even without heating or pressurization from outside the reaction system. Note that the heating and pressurization here are operations (treatments) that are intentionally applied from outside the reaction system, and do not include heat generated by impact or friction in the reaction system (inside the reaction vessel), reaction heat, and pressure increases due to the generation of gases, etc.

[0046] The conversion rate of the hydrogenation reaction can be preferably 95% or more, more preferably 96% or more, even more preferably 98% or more, and particularly preferably 99% or more, both in the case of hydrogenating (substituting with hydrogen) a functional group as a substituent of the product to be hydrogenated and in the case of hydrogenating the skeleton (nucleus) of the product to be hydrogenated.

[0047] Mechanochemical Reactor The mechanochemical reaction device comprises a reaction vessel and a plurality of balls placed in the reaction vessel, the reaction vessel and the balls moving relative to each other, and each ball has a mass of 2 g or more.

[0048] The mechanochemical reactor is equipped with a plurality of balls of a predetermined mass, and therefore can perform the hydrogenation reaction of the material to be hydrogenated by the mechanochemical method with a high conversion rate and in safety. As such a mechanochemical reactor, a reactor in the hydrogenation reaction step of the above-mentioned method for producing a hydrogenated product can be suitably adopted. EXAMPLES

[0049] The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In the following examples, even if not specifically described, the structures of the products and the like are analyzed by GC / MS and 1 Confirmed by 1 H NMR.

[0050] In the examples, the following reaction apparatus (reaction vessel and bowl), hydrocarbon and comparative compound as hydrogen generation source, material to be hydrogenated, and metal as catalyst were used. The material to be hydrogenated was subjected to hydrogenation reaction to generate the following hydrogenation reaction products.

[0051] <Reaction Apparatus> The reciprocating mixer mill was a mixer mill MM400 (manufactured by Retsch, Germany), and the reactor vibration frequency was 30 Hz. Reaction vessel: Tungsten carbide (WC) cylindrical vessel (10 mL x 1) SUS cylindrical container (content capacity 5mL x 1) Balls: Tungsten carbide, 1.02g x 27, 2.81g x 10, 5.97g x 2, 14.14g x 2 Made of SUS, weight per piece: 0.52g x 24 pieces

[0052] <Hydrocarbons> Hexane Cyclohexane Heptane Octane Deccan

[0053] <Comparative Compound> water Diethyl Ether

[0054] <Substances to be hydrided and hydrogenation reactants> (Hydrogenation of the skeleton (core)) Toluene was hydrogenated to produce methylcyclohexane as follows: [ka]

[0055] (Hydrogenation of functional groups as substituents) Nitrobenzene was hydrogenated to produce aminobenzene as follows: [ka]

[0056] The hydrogenation reaction of N,N-bis(4-nitrophenethyl)adipamide was carried out as follows to produce N,N-bis(4-aminophenethyl)adipamide. [ka]

[0057] <Metal> Chromium powder (average particle size 45 μm) Nickel powder (average particle size 150 μm) 5% palladium carbon powder (average particle size 200μm)

[0058] [Example 1] A tungsten carbide reaction vessel (capacity 10 mL) was charged with 1 equivalent of toluene (2 mmol), 16 equivalents of hexane, 50 equivalents of chromium powder, and 25 equivalents of nickel powder per equivalent of toluene, and two tungsten carbide balls (mass 14.14 g) were also charged, followed by sealing. The reaction vessel was fixed to the vibration part of a mixer mill MM400, and the reaction vessel was vibrated back and forth at 30 Hz for 12 hours to carry out the hydrogenation reaction of toluene. During this time, no heat or pressure was applied from outside the reaction system. The conversion rate of toluene to methylcyclohexane was over 99%.

[0059] [Examples 2 to 12 and Comparative Examples 1 to 4] The hydrogenation reaction of the materials to be hydrogenated was carried out in the same manner as in Example 1, except that the reaction vessel, ball, materials to be hydrogenated, hydrocarbons, metals, and reaction time were changed as shown in Table 1. The conversion rates of each material to be hydrogenated are also shown in Table 1.

[0060] [Table 2]

[0061] As is clear from Table 2, the hydrogenated reaction product could be produced in the examples with a higher conversion rate than in the comparative examples. [Industrial Applicability]

[0062] According to the method for producing a hydrogenation reaction product of the present invention, the hydrogenation reaction can be carried out safely with a high conversion rate. According to the mechanochemical reaction device of the present invention, the hydrogenation reaction of the material to be hydrogenated by the mechanochemical method can be carried out safely with a high conversion rate.

Claims

1. A method for producing a hydrogenation reactant, comprising the steps of: The method includes a step of carrying out a hydrogenation reaction of a substance to be hydrogenated by a mechanochemical method using relative motion between a reaction vessel and a plurality of balls placed in the reaction vessel in a reaction apparatus, the reaction vessel and the balls being disposed in the reaction vessel, The hydrogenation reaction is carried out in the presence of a hydrocarbon, The method for producing a hydrogenation reactant, wherein the mass of each of the balls is 2 g or more.

2. The method for producing a hydrogenation product according to claim 1, wherein the hydrocarbon is a saturated hydrocarbon.

3. 3. The method for producing a hydrogenation reaction product according to claim 1, wherein the hydrocarbon is a linear or cyclic saturated hydrocarbon having 6 to 12 carbon atoms.

4. The method for producing a hydrogenation reaction product according to any one of claims 1 to 3, wherein the hydrogenation reaction is carried out in the presence of at least chromium and nickel.

5. The method for producing a hydrogenation reaction product according to claim 4, wherein the amount A of chromium present and the amount B of nickel present satisfy A ≥ B on a molar basis.

6. The method for producing a hydrogenation product according to any one of claims 1 to 5, wherein the hydrogenation reaction is carried out in the presence of at least one metal selected from the group consisting of palladium and platinum.

7. The method for producing a hydrogenation reactant according to any one of claims 1 to 6, wherein a part or all of the reaction vessel and the balls each independently contain at least one selected from the group consisting of stainless steel, agate, alumina, tungsten carbide, chromium steel, zirconia, silicon nitride, brass, and Teflon.

8. The method for producing a hydrogenation product according to any one of claims 1 to 7, wherein the hydrogenation reaction is carried out without applying heat or pressure from outside the reaction system, or both.

9. A mechanochemical reaction apparatus used in the method for producing a hydrogenation reactant according to any one of claims 1 to 8, A reaction vessel and a plurality of balls are inserted into the reaction vessel, and the reaction vessel and the balls move relative to each other; A mechanochemical reaction device in which the mass of each of the balls is 2 g or more.

10. 10. The mechanochemical reaction apparatus of claim 9, wherein the reaction vessel and some or all of the balls each independently comprise at least one selected from the group consisting of stainless steel, agate, alumina, tungsten carbide, chromium steel, zirconia, silicon nitride, brass, and Teflon.

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