Composition for hydrogenation reaction, method for producing hydrogenated compounds, and method for producing polymer raw materials

Abstract

The present invention provides a hydrogenation reaction composition that can efficiently produce hydrogenated compounds. [Solution] A hydrogenation reaction composition comprising a heterogeneous catalyst dispersed in a mixed solution of an aqueous alcohol solution containing water and alcohol and a compound represented by general formula (I), wherein the water content in the aqueous alcohol solution is 5% by mass or more, and the content of the compound represented by general formula (I) is 1 to 80 parts by mass per 100 parts by mass of the aqueous alcohol solution. TIFF2026079064000010.tif28169 [In the formula, R 1 and R 2 Each of these independently represents either a hydrogen atom, a chlorine atom, a hydroxyl group, an amino group, a hydroxymethyl group, or an aminomethyl group.

Description

[Technical Field]

[0001] This invention relates to a composition for hydrogenation reactions, a method for producing hydrogenated compounds, and a method for producing polymer raw materials. [Background technology]

[0002] Furan derivatives and compounds having a tetrahydrofuran skeleton have long been widely used as resins and pharmaceutical intermediates. Generally, the desired furan derivative is synthesized by reacting a substituted furan derivative with a hydrogen source and hydrocracking it. Compounds having a tetrahydrofuran skeleton are produced by reacting a compound having a furan skeleton with a hydrogen source and hydrogenating it. Patent Document 1 discloses a method for producing 2,5-bis(aminomethyl)tetrahydrofuran by reacting 2,5-bis(aminomethyl)furan with a hydrogen source using a hydrogenation catalyst. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Patent No. 7243630 [Overview of the project] [Problems that the invention aims to solve]

[0004] Conventional technologies do not produce sufficient hydrogenated compounds by hydrogenation reactions of compounds having a furan skeleton, compounds having a furan skeleton with some or all substituents replaced by hydrogen, or compounds having a tetrahydrofuran skeleton with some or all substituents replaced by hydrogen (hereinafter referred to as hydrogenated compounds). For example, in the method for producing 2,5-bis(aminomethyl)tetrahydrofuran described in Patent Document 1, which involves reacting 2,5-bis(aminomethyl)furan with a hydrogen source using a hydrogenation catalyst, the production rate of 2,5-bis(aminomethyl)tetrahydrofuran is slow. To produce 2,5-bis(aminomethyl)tetrahydrofuran on an industrial scale, large manufacturing facilities and large quantities of expensive hydrogenation catalysts are required, resulting in poor productivity.

[0005] This invention has been made in view of the above circumstances, and aims to provide a hydrogenation reaction composition that can efficiently produce hydrogenated compounds. [Means for solving the problem]

[0006] As a result of diligent research to solve the above problems, the inventors of the present invention have discovered a specific hydrogenation reaction composition that improves the rate of hydrogenation compound formation and increases the productivity of hydrogenation compounds, and have completed the present invention. That is, the present invention has the following configuration. (1) A hydrogenation reaction composition comprising a heterogeneous catalyst dispersed in a mixed solution of an aqueous alcohol solution containing water and alcohol and a compound represented by general formula (I), wherein the water content in the aqueous alcohol solution is 5% by mass or more, and the content of the compound represented by general formula (I) is 1 to 80 parts by mass per 100 parts by mass of the aqueous alcohol solution.

[0007] [ka]

[0008] [In the formula, R 1 and R 2Each of these independently represents either a hydrogen atom, a chlorine atom, a hydroxyl group, an amino group, a hydroxymethyl group, or an aminomethyl group. (2) The hydrogenation reaction composition according to (1) above, wherein the alcohol is one or more alcohols selected from the group consisting of methanol, ethanol, propanol, and butanol. (3) The hydrogenation reaction composition according to (1) above, wherein the alcohol is methanol. (4) The hydrogenation reaction composition according to (1) above, wherein the water content in the alcohol aqueous solution is 5% by mass or more and 25% by mass or less. (5) The hydrogenation reaction composition according to (1) above, wherein the water content in the aqueous alcohol solution is 5% by mass or more and 20% by mass or less. (6) The hydrogenation reaction composition according to (1) above, wherein the heterogeneous catalyst is one or more metal catalysts selected from the group consisting of Cu, Fe, Co, Ni, Ru, Pd, Pt, Rh, Ir, Re, and Ag. (7) The hydrogenation reaction composition according to (1) above, wherein the heterogeneous catalyst is one or more metal catalysts selected from the group consisting of Cu, Co, Ru, Pd, Pt, Rh, and Re. (8) The hydrogenation reaction composition according to (1) above, wherein the heterogeneous catalyst is Rh. (9) The hydrogenation reaction composition according to (1) above, wherein the compound represented by the general formula (I) is a compound selected from the group consisting of furfural (Ia), furfurylamine (Ib), 2,5-bis(hydroxymethyl)furan (Ic), and 2,5-bis(aminomethyl)furan (Id).

[0009] [ka]

[0010] (10) The hydrogenation reaction composition according to (1) above, wherein the compound represented by the general formula (I) is 2,5-bis(aminomethyl)furan. (11) A method for producing a hydrogenated compound, comprising a step of reacting hydrogen with the composition for hydrogenation reaction according to any one of (1) to (10) above. (12) A method for producing a polymer raw material, comprising obtaining a polymer raw material from the hydrogenated compound obtained by the method for producing a hydrogenated compound according to (11) above as a raw material. (13) The method for producing a polymer raw material according to (12) above, wherein the polymer raw material is hexamethylenediamine or terephthalic acid.

Advantages of the Invention

[0011] According to the present invention, a composition for hydrogenation reaction that gives a high production rate of a hydrogenated compound can be provided.

Embodiments for Carrying Out the Invention

[0012] Hereinafter, preferred embodiments of the present invention will be described in detail. It should be understood that the present invention is not limited only to the embodiments described below, but also includes various modifications implemented within the scope not changing the gist of the present invention.

[0013] [Composition for Hydrogenation Reaction] The composition for hydrogenation reaction of the present invention is a composition for hydrogenation reaction in which a heterogeneous catalyst is dispersed in a mixed solution of an aqueous alcohol solution containing water and alcohol and a compound represented by the general formula (I), the content of water in the aqueous alcohol solution is 5% by mass or more, and the content of the compound represented by the general formula (I) with respect to 100 parts by mass of the aqueous alcohol solution is 1 to 80 parts by mass.

[0014]

Chemical Formula

[0015] In the formula, R 1 and R 2 each independently represent any one of a hydrogen atom, a chlorine atom, a hydroxyl group, an amino group, a hydroxymethyl group, or an aminomethyl group.

[0016] Regarding the aqueous alcohol solution, the compound represented by the general formula (I), and the heterogeneous catalyst used in the composition for the hydrogenation reaction of the present invention, in terms of excellent reaction efficiency, it is preferably a high-purity product or an isolated product, but it is not necessarily required to be a high-purity product or an isolated product.

[0017] As a method for producing the composition for the hydrogenation reaction of the present invention, it may be produced by mixing and dispersing the above-mentioned aqueous alcohol solution, the compound represented by the general formula (I), and the heterogeneous catalyst, or it may be produced indirectly by some chemical reaction.

[0018] The method for analyzing the components in the composition for the hydrogenation reaction is not particularly limited. For example, Karl Fischer titration can be used for measuring the water content. Also, for measuring the content of the alcohol and the compound represented by the general formula (I), 1 1H NMR or GC can be used. Also, the content of the heterogeneous catalyst can be measured by filtering off the heterogeneous catalyst from the composition for the hydrogenation reaction, drying it, and then performing mass spectrometry.

[0019] In the above general formula (I), R 1 and R 2 are, as described above, each independently represent any one of a hydrogen atom, a chlorine atom, a hydroxyl group, an amino group, a hydroxymethyl group, or an aminomethyl group.

[0020] The above R 1 and R 2Regarding this, in terms of excellent hydrogenation reaction efficiency, it is preferable that each is independently a hydrogen atom, a hydroxymethyl group, or an aminomethyl group, more preferably independently a hydroxymethyl group or an aminomethyl group, and even more preferably an aminomethyl group. Specifically, the compound represented by general formula (I) is preferably a compound selected from the group consisting of furfural (Ia), furfurylamine (Ib), 2,5-bis(hydroxymethyl)furan (Ic), and 2,5-bis(aminomethyl)(Id)furan, more preferably a compound selected from the group consisting of 2,5-bis(hydroxymethyl)furan (Ic) and 2,5-bis(aminomethyl)furan (Id), and even more preferably 2,5-bis(aminomethyl)furan (Id).

[0021] [ka]

[0022] The content of the compound represented by the above general formula (I) per 100 parts by mass of the aqueous alcohol solution is 1 to 80 parts by mass. The content is preferably 5 to 75 parts by mass, and more preferably 5 to 70 parts by mass, in terms of excellent hydrogenation reaction efficiency.

[0023] The content of the heterogeneous catalyst is not particularly limited, but in terms of excellent hydrogenation reaction efficiency, the content of the heterogeneous catalyst in 100% by mass of the hydrogenation reaction composition is preferably 0.1 to 50% by mass, more preferably 0.1 to 40% by mass, and even more preferably 0.1 to 3% by mass.

[0024] The aforementioned alcohol is not particularly limited, but it is preferably one or more alcohols selected from the group consisting of methanol, ethanol, propanol, and butanol, and more preferably methanol, due to its excellent hydrogenation reaction efficiency and ease of purification.

[0025] The water content in the aforementioned aqueous alcohol solution is 5% by mass or more, and is not particularly limited, but is preferably 5% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less, even more preferably 5% by mass or more and 25% by mass or less, and particularly preferably 5% by mass or more and 20% by mass or less, in terms of excellent hydrogenation reaction efficiency.

[0026] The heterogeneous catalyst is not particularly limited, but is preferably a metal catalyst, a metal oxide catalyst, an organic complex catalyst, an organometallic structure catalyst, a biocatalyst, an enzyme catalyst, or a mixture thereof, and is more preferably a metal catalyst.

[0027] The above heterogeneous catalyst is not particularly limited, but is preferably one or more metal catalysts selected from the group consisting of Cu, Fe, Co, Ni, Ru, Pd, Pt, Rh, Ir, Re, and Ag, more preferably one or more metal catalysts selected from the group consisting of Cu, Co, Ni, Ru, Pd, Pt, Rh, and Re, and even more preferably Rh.

[0028] Regarding the above-mentioned metal catalyst, it is possible to use the metal itself, or to use a composite material of metal and metal oxide obtained by partially reducing a metal oxide, a mixture with other carriers, or a catalyst supported on other carriers.

[0029] The above-mentioned carriers are not particularly limited, but examples include activated carbon, silica, alumina, alumina silicate, and metal oxides.

[0030] Of the above metals, those with an average particle size (D50) in the range of 0.1 nm to 5000 nm are preferred in terms of excellent catalytic activity, those with an average particle size in the range of 0.1 nm to 3000 nm are more preferred, and those with an average particle size in the range of 0.1 nm to 2000 nm are even more preferred.

[0031] The average particle size (D50) mentioned above can be quantified after observing its shape using a general scanning transmission electron microscope.

[0032] The catalysts in which the above-mentioned metals are supported on other carriers are not particularly limited, but can be prepared, for example, by impregnation or precipitation methods.

[0033] The impregnation method described above is not particularly limited, but a common method is to disperse a carrier in an aqueous solution containing a metal salt, then evaporate the water to support the metal salt on the carrier, and then calcine and reduce it.

[0034] The precipitation method described above is not particularly limited, but a common method is to convert a base into an aqueous solution of a metal salt in which a support is dispersed, and then filter, dry, calcine, and reduce the precipitate obtained.

[0035] The reduction described above is not limited to any particular method, but a common method is the reduction of a metal precursor by contacting it with hydrogen.

[0036] The shape of the heterogeneous catalyst is not particularly limited, but it may be a powdered heterogeneous catalyst or a heterogeneous catalyst formed by adding a binder or the like.

[0037] The heterogeneous catalysts formed by adding the above-mentioned binders, etc., are not particularly limited, but examples include metal catalysts molded into spherical, cylindrical, ring-shaped, or honeycomb shapes.

[0038] The dispersion state of the heterogeneous catalyst in the hydrogenation reaction composition is not particularly limited, but examples include a state in which it is dispersed in a form that is not fixed in the liquid phase, or a state in which the heterogeneous catalyst is packed into the reaction vessel and the gaps are filled with the liquid phase.

[0039] [Method for producing hydrogenated compounds] The method for producing the hydrogenated compound of the present invention comprises the step of reacting hydrogen with the hydrogenation reaction composition of the present invention.

[0040] The above-mentioned hydrogenated compounds are not particularly limited, but include compounds having a tetrohydrofuran skeleton, compounds having a furan skeleton with some or all of its substituents replaced by hydrogen, or compounds having a tetrahydrofuran skeleton with some or all of its substituents replaced by hydrogen. The hydrogenated compound is preferably tetrahydrofurfuryl alcohol (IIa), tetrahydrofururylamine (IIb), furfuryl alcohol (IIc), furfurylamine (IId), 2,5-dimethylfuran (IIe), 2,5-bis(hydroxymethyl)tetrahydrofuran (IIf), or 2,5-bis(aminomethyl)tetrahydrofuran (IIg), more preferably 2,5-dimethylfuran (IIe), 2,5-bis(hydroxymethyl)tetrahydrofuran (IIf), or 2,5-bis(aminomethyl)tetrahydrofuran (IIg), even more preferably 2,5-bis(hydroxymethyl)tetrahydrofuran (IIf) or 2,5-bis(aminomethyl)tetrahydrofuran (IIg), and particularly preferably 2,5-bis(aminomethyl)tetrahydrofuran (IIg).

[0041] [ka]

[0042] The form of the hydrogen reaction process is not particularly limited, but examples include batch reactions, semi-continuous reactions, or continuous reactions.

[0043] In the step of reacting with hydrogen, the method of reacting with hydrogen to the hydrogenation reaction composition is not particularly limited, but examples include bubbling contact, atmospheric pressure contact, pressurized contact, etc., and these may be carried out in combination.

[0044] The pressure (gauge pressure) for the pressurized contact described above should be adjusted so that a hydrogenated compound is obtained, but for example, a range of 0.01 to 10 MPa is preferred, and a range of 0.01 to 7 MPa is more preferred.

[0045] In the step of reacting with hydrogen, the temperature at which the hydrogen is reacted should be adjusted so as to yield a hydrogenated compound, but for example, a range of 20°C to 200°C is preferred, and a range of 30°C to 100°C is more preferred.

[0046] In the step of reacting with hydrogen, the time for reacting with hydrogen can be adjusted so as to obtain a hydrogenated compound, but for example, a range of 0.1 to 24 hours is preferred, a range of 0.1 to 12 hours is more preferred, and a range of 0.1 to 6 hours is even more preferred.

[0047] The hydrogenated compound produced by the present invention can be isolated and purified from the hydrogenation reaction composition after treatment with hydrogen by distillation purification.

[0048] When isolating and purifying the catalyst, it is preferable to remove heterogeneous catalysts beforehand to prevent deterioration of purification efficiency. There are no particular limitations on the method for removing heterogeneous catalysts beforehand, but examples include removing heterogeneous catalysts beforehand by operations such as membrane filtration or centrifugation of the hydrogenation reaction composition after reaction with hydrogen.

[0049] When purifying hydrogenated compounds by distillation, the distillation conditions are not particularly limited, but are usually carried out at a temperature of 20°C to 250°C and a pressure of 5 mmHg to 760 mmHg. The unreacted compound represented by general formula (I) and the aqueous alcohol solution recovered at this time may be used again as raw materials for the hydrogenation reaction composition.

[0050] [Method for manufacturing polymer raw materials] The present invention provides a method for producing polymer raw materials, using a hydrogenated compound obtained by the present invention's method for producing hydrogenated compounds as a raw material. Specifically, a polymer raw material can be produced by using a hydrogenated compound obtained by the present invention's method for producing hydrogenated compounds as a raw material and performing an appropriate reaction. Specific examples include a method for producing pentanediol by reducing tetrahydrofurfuryl alcohol obtained by the present invention's method as a raw material; a method for producing hexanediol by reducing 2,5-bis(hydroxymethyl)tetrahydrofuran; a method for producing hexamethylenediamine by reducing 2,5-bis(aminomethyl)tetrahydrofuran; and a method for producing terephthalic acid by oxidizing paraxylene obtained by reacting 2,5-dimethylfuran with ethylene as a raw material. In particular, the methods for producing hexanediol by reducing 2,5-bis(hydroxymethyl)tetrahydrofuran, the methods for producing hexamethylenediamine by reducing 2,5-bis(aminomethyl)tetrahydrofuran, and the methods for producing terephthalic acid by oxidizing paraxylene obtained by reacting 2,5-dimethylfuran with ethylene are preferred, the methods for producing hexamethylenediamine by reducing 2,5-bis(aminomethyl)tetrahydrofuran, the methods for producing terephthalic acid by oxidizing paraxylene obtained by reacting 2,5-dimethylfuran with ethylene are more preferred, and the method for producing hexamethylenediamine by reducing 2,5-bis(aminomethyl)tetrahydrofuran is even more preferred. That is, the polymer raw material is preferably hexanediol, hexamethylenediamine, or terephthalic acid, and more preferably hexamethylenediamine or terephthalic acid.

[0051] In the method for producing polymer raw materials of the present invention, the number of reactions from the hydrogenated compound to obtain the polymer raw material is preferably 3 or less, and more preferably 2 or less, from the viewpoint of productivity.

[0052] The hydrogenated compound used as a raw material in the method for producing the polymer raw material of the present invention may be used as a reaction mixture without isolating and purifying the hydrogenation reaction composition obtained by the method for producing the hydrogenated compound of the present invention after reaction with hydrogen, or the hydrogenated compound may be used after isolation and purification. [Examples]

[0053] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0054] [GC measurement] GC measurements were performed using a Shimadzu GC-2010 plus (detector: flame ionization detector). The column used was an Agilent Technologies DB-5. Analysis conditions GC system: GC2010 plus (manufactured by Shimadzu Corporation) Column: DB-5, length 30m, inner diameter 0.32mm (manufactured by Agilent Technologies, Inc.) Carrier gas: Helium, constant linear velocity (20.0 cm / sec) Evaporation chamber temperature: 330℃ Detector temperature: 330℃ Column oven temperature: 50℃ → (10℃ / min) → 325℃ for 2.5 minutes (total 30 minutes).

[0055] [Preparation of compositions for hydrogenation reactions and production of hydrogenated compounds] In the following examples and comparative examples, an aqueous alcohol solution was prepared by mixing pure water and alcohol manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.

[0056] [Example 1] 0.5 g (5 mmol) of 2,5-bis(aminomethyl)furan (Angene) (Ia) was mixed with 4.0 g (approximately 5 mL) of an aqueous methanol solution containing 8% by mass of water. 30 mg of Rh / C catalyst (Tokyo Chemical Industries, Ltd.) was then dispersed in the mixture to obtain a hydrogenation reaction composition. This hydrogenation reaction composition was placed in a 30 mL autoclave, the lid was closed, and the container was pressurized to 0.99 MPa with hydrogen (Taiyo Nippon Sanso Corporation), then released to atmospheric pressure. This process was repeated three times, after which the container was pressurized to 0.99 MPa and sealed. While maintaining the seal, the container was heated and stirred at 90°C for 1.5 hours. The autoclave was then cooled to room temperature. After filtering the Rh / C catalyst from the resulting autoclave contents, the filtrate was analyzed by GC. The results are shown in Table 1-1.

[0057] [Comparative Example 1] The procedure was carried out under the same conditions as in Example 1, except that the methanol aqueous solution was changed to 4.0 g (approximately 5 mL) of methanol. The results are shown in Table 1-1.

[0058] [Comparative Example 2] The procedure was carried out under the same conditions as in Example 1, except that the methanol aqueous solution was replaced with 5.0 g (approximately 5 mL) of water.

[0059] The results are shown in Table 1-1.

[0060] [Example 2] The procedure was carried out under the same conditions as in Example 1, except that 4.0 g (approximately 5 mL) of methanol aqueous solution containing 8% by mass of water was replaced with 4.1 g (approximately 5 mL) of methanol aqueous solution containing 15% by mass of water.

[0061] The results are shown in Table 1-1.

[0062] [Example 3] The procedure was carried out under the same conditions as in Example 1, except that 4.0 g (approximately 5 mL) of methanol aqueous solution containing 8% by mass of water was replaced with 4.2 g (approximately 5 mL) of methanol aqueous solution containing 30% by mass of water.

[0063] The results are shown in Table 1-2.

[0064] [Example 4] The procedure was carried out under the same conditions as in Example 1, except that 4.0 g (approximately 5 mL) of methanol aqueous solution containing 8% by mass of water was replaced with 4.5 g (approximately 5 mL) of methanol aqueous solution containing 56% by mass of water.

[0065] The results are shown in Table 1-2.

[0066] [Example 5] The procedure was carried out under the same conditions as in Example 1, except that 4.0 g (approximately 5 mL) of methanol aqueous solution containing 8% by mass of water was replaced with 4.6 g (approximately 5 mL) of methanol aqueous solution containing 68% by mass of water.

[0067] The results are shown in Table 1-2.

[0068] [Example 6] The procedure was carried out under the same conditions as in Example 1, except that 4.0 g (approximately 5 mL) of methanol aqueous solution containing 8% by mass of water was replaced with 4.7 g (approximately 5 mL) of methanol aqueous solution containing 79% by mass of water.

[0069] The results are shown in Table 1-2.

[0070] [Table 1-1]

[0071] [Table 1-2]

[0072] As shown in Tables 1-1 and 1-2 above, the rate of hydrogenation compound production using the hydrogenation reaction compositions used in Examples 1-6 was higher than the rate of hydrogenation compound production in Comparative Examples 1-2. From these results, it was understood that hydrogenation compounds can be efficiently produced using the hydrogenation reaction compositions of Examples 1-6 and the method of producing hydrogenation compounds by reacting the hydrogenation reaction compositions of Examples 1-6 with hydrogen.

[0073] In particular, as can be seen from the results of Comparative Examples 1 and 2, the rate of hydrogenation compound formation was higher in methanol solvent than in aqueous solvent. On the other hand, as can be seen from the results of Examples 1 to 6, the relationship between the water content in an aqueous methanol solution and the hydrogenation compound formation rate is volcanic, and the optimal water content in the aqueous methanol solution was 15% by mass. When the water content was increased beyond 15% by mass, the hydrogenation compound formation rate decreased, but it was still higher than in Comparative Example 1, which used a pure aqueous solvent.

[0074] The mechanism by which the hydrogenation reaction composition of the present invention increases the rate of hydrogenation compound formation is, although this is merely a hypothesis, that changing from a pure alcohol to an aqueous alcohol solution suppresses the adsorption of the compound represented by general formula (I) onto the heterogeneous catalyst, making it easier for hydrogen to be activated on the surface of the heterogeneous catalyst and improving the rate of hydrogenation compound formation. On the other hand, in a pure aqueous solvent, water is strongly adsorbed onto the surface of the heterogeneous catalyst, making it difficult for hydrogen to be activated and thus decreasing the rate of hydrogenation compound formation. [Industrial applicability]

[0075] When using the hydrogenation reaction composition of the present invention, hydrogenated compounds can be produced at a higher rate compared to conventional techniques. Therefore, compared to conventional techniques, the scale of the equipment and the amount of expensive precious metal catalysts can be reduced, and hydrogenated compounds can be produced at a lower cost.

Claims

1. A hydrogenation reaction composition comprising a heterogeneous catalyst dispersed in a mixed solution of an aqueous alcohol solution containing water and alcohol and a compound represented by general formula (I), wherein the water content in the aqueous alcohol solution is 5% by mass or more, and the content of the compound represented by general formula (I) is 1 to 80 parts by mass per 100 parts by mass of the aqueous alcohol solution. 【Chemistry 1】 [In the formula, R １ and R ２ Each of these independently represents either a hydrogen atom, a chlorine atom, a hydroxyl group, an amino group, a hydroxymethyl group, or an aminomethyl group.

2. The hydrogenation reaction composition according to claim 1, wherein the alcohol is one or more alcohols selected from the group consisting of methanol, ethanol, propanol, and butanol.

3. The hydrogenation reaction composition according to claim 1, wherein the alcohol is methanol.

4. The hydrogenation reaction composition according to claim 1, wherein the water content in the alcohol aqueous solution is 5% by mass or more and 25% by mass or less.

5. The hydrogenation reaction composition according to claim 1, wherein the water content in the alcohol aqueous solution is 5% by mass or more and 20% by mass or less.

6. The hydrogenation reaction composition according to claim 1, wherein the heterogeneous catalyst is one or more metal catalysts selected from the group consisting of Cu, Fe, Co, Ni, Ru, Pd, Pt, Rh, Ir, Re, and Ag.

7. The hydrogenation reaction composition according to claim 1, wherein the heterogeneous catalyst is one or more metal catalysts selected from the group consisting of Cu, Co, Ru, Pd, Pt, Rh, and Re.

8. The hydrogenation reaction composition according to claim 1, wherein the heterogeneous catalyst is Rh.

9. The hydrogenation reaction composition according to claim 1, wherein the compound represented by the general formula (I) is a compound selected from the group consisting of furfural (Ia), furfurylamine (Ib), 2,5-bis(hydroxymethyl)furan (Ic), and 2,5-bis(aminomethyl)furan (Id). 【Chemistry 2】

10. The hydrogenation reaction composition according to claim 1, wherein the compound represented by the general formula (I) is 2,5-bis(aminomethyl)furan.

11. A method for producing a hydrogenated compound, comprising the step of reacting hydrogen with any of the hydrogenation reaction compositions described in claims 1 to 10.

12. A method for producing a polymer raw material, comprising obtaining a hydrogenated compound obtained by the method for producing a hydrogenated compound described in claim 11, using the hydrogenated compound as a raw material.

13. The method for producing a polymer raw material according to claim 12, wherein the polymer raw material is hexamethylenediamine or terephthalic acid.

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