Catalyst, method for producing catalyst, and method for producing hydrogenated compound

Abstract

The present invention provides: a catalyst that can be suitably used in a hydrogenation reaction; a method for producing a catalyst that can be suitably used in a hydrogenation reaction; and a method for producing a hydrogenated compound, the method being capable of suitably advancing the hydrogenation reaction of an unsaturated compound having a carbon-carbon multiple bond in the molecule and suitably yielding a target hydrogenated compound. The catalyst of the present invention includes: a first element that is a platinum group element; a second element that is a platinum group element different from the first element; a silicon compound having a silicon-oxygen bond; and a substrate that supports the first element, the second element, and the silicon compound. The first element is preferably Pt. The second element is preferably Rh. The silicon compound is preferably poly(methylhydrosiloxane).

Description

Catalyst, method for producing the catalyst, and method for producing a hydrogenated compound

[0001] Some aspects of the present invention relate to catalysts, methods for producing catalysts, and methods for producing hydrogenated compounds.

[0002] Various catalysts are used in the chemical industry. For example, unsaturated compounds having carbon-carbon multiple bonds are reacted with H ２ Raney nickel catalysts are known as catalysts used in hydrogenation reactions that involve reduction.

[0003] However, Raney nickel catalysts have several drawbacks, including their high flammability, making them dangerous to handle, and their lower catalytic activity compared to precious metal catalysts, requiring reactions to be carried out under harsh conditions such as high temperature and pressure. These factors inevitably lead to limitations in scale-up capacity and increased costs. These problems are particularly pronounced when performing hydrogenation reactions that reduce aromatic carbon-carbon double bonds.

[0004] For these reasons, in recent years, several noble metal catalysts have been proposed in academic journals that are easier to handle than Raney nickel catalysts and allow hydrogenation reactions under milder conditions, for both homogeneous and heterogeneous systems.

[0005] For example, [Rh(COD)Cl] ２ It has been reported that when used as a homogeneous catalyst, the nuclear hydrogenation reaction from cresol to methylcyclohexanol proceeds under conditions of 40°C and 5-10 atm (see Non-Patent Document 1).

[0006] However, this catalytic reaction has a low maximum yield of 90%, and the amount of catalyst required is very high at 2 mol%, making it unsuitable for practical application.

[0007] Org. Lett. 2024, 26, 3458-3462

[0008] Objects of some aspects of the present invention include providing a catalyst suitably usable in hydrogenation reactions, providing a method for producing a catalyst suitably usable in hydrogenation reactions, and providing a method for producing a hydrogenated compound that can suitably proceed with the hydrogenation reaction of an unsaturated compound having carbon-carbon multiple bonds in its molecule, thereby suitably obtaining a target hydrogenated compound.

[0009] A catalyst according to some embodiments of the present invention is characterized by comprising a first element which is a platinum group element, a second element which is a platinum group element different from the first element, a silicon compound having a silicon-oxygen bond, and a substrate supporting the first element, the second element, and the silicon compound. In the above catalyst, for example, since the silicon-oxygen bond is a stable bond, leakage of the metal at the catalyst center can be suppressed in a wide range of operating environments for the catalyst.

[0010] In the catalyst described above, it is preferable that the silicon compound further has silicon-hydrogen bonds. This allows, for example, the silicon-hydrogen bonds to act as capture sites for the catalyst centers, contributing to maintaining a highly dispersed state of the catalyst centers.

[0011] In catalysts according to some embodiments of the present invention, the first element is preferably platinum (Pt).

[0012] In catalysts according to some embodiments of the present invention, the second element is preferably rhodium (Rh).

[0013] In catalysts according to some embodiments of the present invention, the silicon compound is preferably a compound having an organic group. The organic group may include, for example, carbon and hydrogen, and may also include heteroatoms such as oxygen, nitrogen, phosphorus, silicon, and sulfur.

[0014] In catalysts according to some embodiments of the present invention, the silicon compound preferably comprises a plurality of silicon units having a hydrocarbon group such as a methyl group and a hydrogen group. Typical examples include poly(methylhydrosiloxane).

[0015] In catalysts according to some embodiments of the present invention, the substrate is preferably a porous material.

[0016] In catalysts according to some embodiments of the present invention, it is preferable that the substrate is composed of a material comprising at least one selected from the group consisting of alumina, silica, hydrotalcite, magnesium lanthanum oxide, zeolite, sulfated zirconia, and activated carbon.

[0017] A method for producing a catalyst according to some embodiments of the present invention is characterized by comprising: a first mixture preparation step of preparing a first substance as a metal salt or metal compound containing a first element which is a platinum group element; a second substance as a metal salt or metal compound containing a second element which is a platinum group element different from the first element; and a substrate; a second mixture preparation step of mixing the first mixture with a composition containing a silicon compound having a silicon-oxygen bond to obtain a second mixture; and a reduction step of reducing at least one of the first substance and the second substance contained in the second mixture using a reducing agent.

[0018] In a method for producing a catalyst according to some embodiments of the present invention, it is preferable that at least one of the first substance and the second substance contains chlorine.

[0019] In a method for producing a catalyst according to some embodiments of the present invention, the first substance is preferably chloroplatinic acid.

[0020] In a method for producing a catalyst according to some embodiments of the present invention, the second substance is preferably rhodium chloride.

[0021] In a method for producing a catalyst according to some embodiments of the present invention, the reducing agent is NaBH ４ It is preferable to use an alkaline aqueous solution containing [the specified substance].

[0022] The method for producing a hydrogenated compound according to an application example of some aspects of the present invention includes a catalyst preparation step of preparing a catalyst according to an application example of some aspects of the present invention, and a hydrogenation step of performing hydrogen addition to an unsaturated compound having a carbon-carbon multiple bond in the molecule in the presence of the catalyst.

[0023] In the method for producing a hydrogenated compound according to an application example of some aspects of the present invention, the unsaturated compound has an aromatic carbon-carbon double bond, and it is preferable that the carbon-carbon double bond is reduced in the hydrogenation step.

[0024] In the method for producing a hydrogenated compound according to an application example of some aspects of the present invention, the unsaturated compound has an aromatic ring, and it is preferable that the aromatic ring is reduced in the hydrogenation step and changed to a saturated alicyclic structure.

[0025] In the method for producing a hydrogenated compound according to an application example of some aspects of the present invention, it is preferable that the aromatic ring has a benzene ring.

[0026] In the method for producing a hydrogenated compound according to an application example of some aspects of the present invention, it is preferable to perform the hydrogenation step in a liquid phase at 10°C or higher and 150°C or lower.

[0027] According to the present invention, it is possible to provide a catalyst that can be suitably used for a hydrogenation reaction, a method for producing a catalyst that can be suitably used for a hydrogenation reaction, and a method for producing a hydrogenated compound that can suitably proceed with the hydrogenation reaction of an unsaturated compound having a carbon-carbon multiple bond in the molecule and can suitably obtain the target hydrogenated compound.

[0028] Hereinafter, the catalyst, the method for producing the catalyst, the method for producing the hydrogenated compound, etc. will be described in detail based on embodiments according to some aspects of the present invention (hereinafter "the present embodiment").

[0029] Regarding the measurements and treatments described in the present embodiment, unless otherwise indicated for temperature conditions, it is assumed that they were performed at room temperature (23°C).

[0030] [1] Catalyst The catalyst according to this embodiment (hereinafter referred to as "the catalyst") comprises a first element which is a platinum group element, a second element which is a platinum group element different from the first element, a silicon compound having a silicon-oxygen bond, and a substrate which supports the first element, the second element, and the silicon compound.

[0031] As a result of diligent research, the inventors have found that, with this configuration, it is possible to provide a catalyst that can be suitably used in hydrogenation reactions, although the detailed mechanism remains unclear.

[0032] Conventional catalysts have problems in various hydrogenation reactions, particularly in the reduction of aromatic carbon-carbon double bonds, such as requiring large amounts of catalyst to proceed with the desired reaction (hydrogenation reaction) or making it difficult to obtain the desired compound (hydrogenated compound) in high yield. Furthermore, conventional catalysts have issues with their activity, such as requiring harsh conditions like high pressure or high temperature to obtain hydrogenated compounds.

[0033] In contrast, this catalyst is broadly applicable to the hydrogenation reactions of unsaturated compounds having carbon-carbon multiple bonds. In particular, even in the hydrogenation reactions of aromatic compounds where high catalytic activity is required, the target compound (hydrogenated compound) can be obtained in high yield with a small amount of catalyst used. Moreover, the target catalytic reaction can proceed under mild conditions, including room temperature and atmospheric pressure.

[0034] Furthermore, this catalyst has low flammability and excellent safety. Additionally, the elution of platinum group elements constituting the catalyst center into the reaction solution is effectively prevented, thus extending the catalyst's lifespan. Moreover, even when the catalyst's activity decreases, precious metals can be effectively recovered and reused, making it desirable from the standpoint of efficient resource utilization.

[0035] The platinum group elements include six elements: Ru (ruthenium), Rh (rhodium), Pd (palladium), Os (osmium), Ir (iridium), and Pt (platinum).

[0036] In this catalyst, the first and second elements are different platinum group elements. Therefore, the combination of the first and second elements is any two of these six elements. However, in the following explanation, if the molar ratios of these elements differ in this catalyst, the platinum group element with the higher content will be treated as the "first element," and the platinum group element with the lower content will be treated as the "second element." Furthermore, if the molar ratios of these elements are the same in the catalyst, the platinum group element with the larger atomic number will be treated as the "first element," and the platinum group element with the smaller atomic number will be treated as the "second element."

[0037] Furthermore, as will be described later, this catalyst may contain three or more platinum group elements. In such cases, the two platinum group elements with the highest molar content among those contained in the catalyst shall be treated as the "first element" and the "second element." If the catalyst contains three or more platinum group elements with the same and highest molar content, the platinum group element with the largest atomic number among them shall be treated as the "first element," and the platinum group element with the second largest atomic number shall be treated as the "second element." If the catalyst contains two or more platinum group elements with the second highest molar content, the platinum group element with the largest atomic number among them shall be treated as the "second element."

[0038] [1-1] The catalyst preferably contains a first element with an oxidation state of 0.

[0039] The first element is preferably, for example, rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), or platinum (Pt), and more preferably Pt. This makes it possible to increase the activity of the catalyst.

[0040] The content of the first element in this catalyst is preferably 0.1 mmol / g or more and 4 mmol / g or less, more preferably 0.1 mmol / g or more and 4 mmol / g or less, and even more preferably 0.2 mmol / g or more and 3 mmol / g or less.

[0041] This makes it possible to increase the catalytic activity while suppressing the amount of the first element used.

[0042] In this catalyst, the ratio (molar ratio) of the content of the first element to the amount of Si-H groups in the silicon compound (silicon compound having a silicon-oxygen bond), which will be described in detail later, that is, the value of X1 / XS, where XS [mol] is the amount of Si-H groups in the silicon compound (silicon compound having a silicon-oxygen bond) contained in this catalyst and X1 [mol] is the amount of the first element, is preferably 0.10 or more and 0.90 or less, more preferably 0.15 or more and 0.80 or less, and even more preferably 0.20 or more and 0.70 or less. This makes it possible to make the catalyst more active.

[0043] [1-2] Second Element The catalyst of this embodiment contains a second element with an oxidation state of 0.

[0044] The second element is preferably, for example, ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), or iridium (Ir), and more preferably Rh. This can increase the activity of the catalyst.

[0045] In particular, it is preferable that the first element is Pt and the second element is Rh. This allows for even higher catalytic activity. When the first element is Pt and the second element is Rh, it is thought that Pt mainly plays the role of hydrogen storage, and Rh plays the role of oxidative addition.

[0046] The content of the second element in this catalyst is preferably 0.05 mmol / g or more and 8 mmol / g or less, more preferably 0.1 mmol / g or more and 7 mmol / g or less, and even more preferably 0.2 mmol / g or more and 5 mmol / g or less.

[0047] This makes it possible to increase the catalytic activity while suppressing the amount of the second element used.

[0048] In this catalyst, the ratio (molar ratio) of the content of the second element to the amount of Si-H groups in the silicon compound (silicon compound having a silicon-oxygen bond), which will be described in detail later, that is, the value of X2 / XS, where XS [mol] is the amount of Si-H groups in the silicon compound (silicon compound having a silicon-oxygen bond) contained in this catalyst and X2 [mol] is the amount of the second element, is preferably 0.05 or more and 0.90 or less, more preferably 0.08 or more and 0.80 or less, and even more preferably 0.14 or more and 0.70 or less. This makes it possible to make the catalyst more active.

[0049] In this catalyst, the ratio (molar ratio) of the content of the second element to the content of the first element, that is, the value of X2 / X1 when the content of the first element is X1 [mol] and the content of the second element is X2 [mol], is preferably 0.50 or more and 2.00 or less, more preferably 0.60 or more and 1.00 or less, and even more preferably 0.70 or more and 1.00 or less. This makes it possible to achieve higher catalyst activity.

[0050] [1-3] Silicon Compounds The catalyst of this embodiment contains a silicon compound having a silicon-oxygen bond. Such a silicon compound exhibits functions in this catalyst, for example, by reducing the ignition properties of the catalyst or by preventing the platinum group elements constituting the catalyst from dissolving into the reaction solution.

[0051] In the following sections (within [1-3]) and in the explanations in [2-2] below, silicon compounds having a silicon-oxygen bond will also be simply referred to as "silicon compounds."

[0052] The silicon compound is preferably a compound having silicon-hydrogen bonds. This allows, for example, the silicon-hydrogen bonds to act as capture sites for the catalytic center, contributing to maintaining a highly dispersed state of the catalytic center.

[0053] The silicon compound is preferably a compound having an organic group. The organic group may include, for example, carbon and hydrogen, and may also include heteroatoms such as oxygen, nitrogen, phosphorus, silicon, and sulfur.

[0054] Examples of silicon compounds having an organic group include poly(methylhydrosiloxane) and tetramethylsiloxane ([(CH ３ ) ２ SiH] ２ Examples include compounds having multiple units containing silicon atoms having hydrocarbon groups such as methyl groups and hydrogen groups, and having a structure in which an organic group (hydrocarbon group, etc.) and a hydrogen atom (hydrogen group) are present on the silicon atom, and the silicon atom is bonded to an oxygen atom. Among these, poly(methylhydrosiloxane) is preferred.

[0055] This allows for more stable maintenance of the high dispersion of the metal at the catalyst center of this catalyst, for example. Furthermore, since poly(methylhydrosiloxane) is generally in liquid form, a homogeneous solution can be easily prepared, and it is expected that the polymer will be uniformly adsorbed onto the catalyst surface without variation, which leads to a reduction in variations in catalyst performance.

[0056] Furthermore, the silicon compound contained in this catalyst may be one in which at least a portion of the silicon-hydrogen bonds of the silicon compound used as a raw material in the catalyst manufacturing method described later has been converted to silicon-oxygen bonds. More specifically, when poly(methylhydrosiloxane) is used in the catalyst manufacturing method, the silicon compound contained in the resulting catalyst may be one in which at least a portion of the silicon-hydrogen bonds of the poly(methylhydrosiloxane) has been converted to silicon-oxygen bonds. Even in such cases, the catalyst is treated as containing poly(methylhydrosiloxane).

[0057] Furthermore, for the reasons described below, even if the silicon compound used as a raw material in the catalyst manufacturing method does not have silicon-oxygen bonds, at least a portion of the silicon-hydrogen bonds in the silicon compound are converted into silicon-oxygen bonds during the catalyst manufacturing process, so that the silicon compound contained in this catalyst has silicon-oxygen bonds. For example, in the catalyst manufacturing method, phenylsilane (PhSiH ３Even when using (), at least a part of the silicon-hydrogen bond in phenylsilane is converted to a silicon-oxygen bond, so that the silicon compound contained in this catalyst has a silicon-oxygen bond. Examples of such compounds include, for example, hexatriethyldisiloxane, poly(dimethylsiloxane), and poly(phenylhydrosiloxane) or polyphenylsiloxane. Each of them is, for example, triethylsilane, dihydrodimethylsilane, phenylsilane (PhSiH ３ ), etc. are generated during the synthesis of this catalyst from compounds having an organic group and a hydrogen atom on their silicon atoms. Of course, a part of the plurality of silicon-hydrogen bonds may be converted to silicon-oxygen bonds as described above.

[0058] The content of the silicon compound in this catalyst is preferably 0.5 mmol / g or more and 53 mmol / g or less, more preferably 1 mmol / g or more and 43 mmol / g or less, and even more preferably 2 mmol / g or more and 32 mmol / g or less.

[0059] This can more effectively prevent the platinum group element constituting the catalyst from eluting into the reaction solution, and can make the safety and activity of the catalyst higher.

[0060] [1-4] Substrate The catalyst of this embodiment includes a substrate that supports the aforementioned first element, second element, and a silicon compound having a silicon-oxygen bond. The first element, second element, and silicon compound having a silicon-oxygen bond only need to be supported on the substrate and do not necessarily have to be in direct contact with the substrate. More specifically, for example, at least a part of the first element and the second element adheres to the surface of the silicon compound having a silicon-oxygen bond in a state of contacting the substrate and does not necessarily have to contact the substrate.

[0061] The substrate is preferably a porous body. This can increase the surface area per unit volume of the catalyst and is advantageous for enhancing the activity of the catalyst.

[0062] When the substrate is a porous body, the specific surface area of the porous body constituting the substrate is 1 m ２ / g or more 4000m ２ It is preferable that it is less than or equal to / g, and 2m ２ / g or more 3000m ２ It is more preferable that it be less than or equal to / g, and 3m ２ / g or more 2500m ２ It is even more preferable that the amount is less than or equal to / g.

[0063] This allows for improved catalyst activity while ensuring sufficient stability of the catalyst's shape and mechanical strength.

[0064] The substrate may support the first element, the second element, and the silicon compound having a silicon-oxygen bond at any site, for example, on the outer surface of the substrate or on the inner surface (inside the pores) of the substrate.

[0065] Examples of constituent materials for the substrate include substances containing at least metal atoms and oxygen atoms, such as alumina (α-alumina, γ-alumina), titania, zirconia, silica, hydrotalcite, magnesium lanthanum oxide, zeolite, magnesium oxide, magnesium aluminate, MgLaO, metal salts such as zirconium sulfate and barium sulfate, surface-modified carriers such as sulfated zirconia and sulfated carbon, carbon materials such as activated carbon and carbon fibers, and ceramics such as silicon carbide and silicon nitride. However, it is preferable that the substrate is at least one selected from the group consisting of alumina, silica, hydrotalcite, magnesium lanthanum oxide, zeolite, sulfated zirconia, and activated carbon.

[0066] This allows for more favorable support of the first element, the second element, and silicon compounds having silicon-oxygen bonds.

[0067] The substrate content in this catalyst is preferably 70.0% by mass or more and 99.9% by mass or less, more preferably 73.0% by mass or more and 99.8% by mass or less, and even more preferably 75.0% by mass or more and 99.7% by mass or less.

[0068] This makes it possible to improve the catalyst's activity while ensuring sufficient stability of the catalyst's shape and mechanical strength.

[0069] [1-5] Other Components The catalyst of this embodiment may contain components other than those described above. Hereinafter, in this section ([1-5]), such components will be referred to as "other components".

[0070] Other components include, for example, platinum group elements other than the first and second elements, cobalt (Co), nickel (Ni), manganese (Mn), copper (Cu), rhenium (Re), molybdenum (Mo), tungsten (W), vanadium (V), and niobium (Nb).

[0071] In this embodiment, "average particle size" refers to the average particle size based on volume. For example, it can be determined by adding a sample to methanol, dispersing the dispersion for 3 minutes in an ultrasonic disperser, and measuring the dispersion using a Coulter counter particle size distribution analyzer (TA-II model, manufactured by Coulter Electronics INS) with a 50 μm aperture.

[0072] As described above, the catalyst of this embodiment can be suitably used in hydrogenation reactions. By using this catalyst, suitable results can be obtained even in hydrogenation reactions of aromatic compounds having carbon-carbon double bonds, where it was particularly difficult to obtain the target compound (hydrogenated compound) in high yield with a small amount of conventional catalysts. Furthermore, this catalyst can suitably carry out hydrogenation reactions for various aromatic compounds. Therefore, this catalyst is preferably used in hydrogenation reactions of compounds having aromatic carbon-carbon double bonds.

[0073] Furthermore, this catalyst may also be used in chemical reactions other than hydrogenation reactions.

[0074] [2] Method for manufacturing a catalyst Next, a method for manufacturing a catalyst will be described.

[0075] The method for producing this catalyst comprises a first mixture preparation step of preparing a first substance as a metal salt or metal compound containing a first element which is a platinum group element, a second substance as a metal salt or metal compound containing a second element which is a platinum group element different from the first element, and a substrate; a second mixture preparation step of mixing the first mixture with a composition containing a silicon compound having a silicon-oxygen bond to obtain a second mixture; and a reduction step of reducing the first substance and the second substance contained in the second mixture using a reducing agent.

[0076] This makes it possible to provide a method for producing a catalyst that can be suitably used in hydrogenation reactions.

[0077] In particular, this catalyst can be widely applied to hydrogenation reactions of unsaturated compounds having carbon-carbon multiple bonds, and it can provide a method for producing a catalyst that can obtain the target compound (hydrogenated compound) in high yield with a small amount of material, even in hydrogenation reactions of aromatic compounds where high catalytic activity is required, and it can provide a method for producing a catalyst that can carry out the target catalytic reaction under mild conditions, including room temperature and atmospheric pressure.

[0078] Furthermore, the catalyst produced by the manufacturing method of this embodiment has low flammability and excellent safety. In addition, the elution of platinum group elements constituting the catalyst center into the reaction solution is effectively prevented, thereby extending the lifespan of the catalyst. Moreover, even if the activity of the catalyst decreases, precious metals can be effectively recovered and reused from the catalyst, which is also preferable from the viewpoint of efficient resource utilization.

[0079] Furthermore, this catalyst manufacturing method is advantageous because it does not require the use of highly toxic and dangerous solvents such as methylene chloride. In addition, this embodiment allows for the synthesis of catalysts in high yield, and is particularly advantageous from the viewpoint of efficient resource utilization and cost, as it minimizes losses during the production of catalysts containing expensive and scarce platinum group elements.

[0080] [2-1] Preparation of the first mixture In the preparation of the first mixture, a first substance is prepared, which is a metal salt or metal compound containing a first element that is a platinum group element, a second substance is a metal salt or metal compound containing a second element that is a platinum group element different from the first element, and a substrate.

[0081] [2-1-1] The first substance contained in the first mixture is a metal salt or metal compound containing a first element which is a platinum group element. In this embodiment, the term "metal salt" includes complex salts (salts containing complex ions).

[0082] Examples of the metal salt as the first substance include chlorides, sulfides, hydroxides, oxides, sulfates, bisulfates, oxalates, nitrates, hypochlorites, perchlorates, acetates, and carbonates of the first element, as well as substances containing these compositions. One or more combinations or mixtures selected from these can be used.

[0083] Examples of metal compounds as the first substance include compounds in which at least one molecule of carbon monoxide is coordinated to the first element, compounds containing at least one molecule of a ligand containing a phosphorus atom, compounds containing at least one molecule of a ligand containing a nitrogen atom, and compounds containing at least one molecule of a π-coordinate ligand containing a carbon-carbon double bond, such as a cyclopentadienyl group or cyclooctadienyl. One or more of these can be selected and used in combination.

[0084] As the first substance, a hydrate may be used. As the first substance, a combination of the above-mentioned metal salt and metal compound may be used.

[0085] If the first substance contains chlorine, the target catalyst can be obtained in an even higher yield, and the activity of the resulting catalyst can be made even better.

[0086] When producing a catalyst containing platinum as the first element, the first substance may be chloroplatinic acid (H ２ PtCl ６ , H ２ PtCl ４) and their hydrates can be suitably used.

[0087] This allows for obtaining the desired catalyst in higher yields, and also improves the activity of the resulting catalyst.

[0088] When producing a catalyst containing rhodium as the first element, the first substance may be rhodium chloride (RhCl ３ ) or its hydrate can be suitably used.

[0089] The oxidation number of the first element constituting the first substance is preferably between 2 and 4, and more preferably between 3 and 4.

[0090] This allows for obtaining the desired catalyst in higher yields, and also improves the activity of the resulting catalyst.

[0091] When the first substance is dissolved in the first mixture, the concentration of the first element in the solution is preferably 0.1 mmol / kg or more and 5.0 mmol / kg or less, more preferably 0.3 mmol / kg or more and 4.0 mmol / kg or less, and even more preferably 0.7 mmol / kg or more and 3.0 mmol / kg or less.

[0092] This allows for obtaining the desired catalyst in higher yields, and also improves the activity of the resulting catalyst.

[0093] Furthermore, only the solvent and the components dissolved in this solvent are treated as components of the solution. More specifically, since the substrate is usually not dissolved in the first mixture, the substrate is treated as not constituting a part of the solution.

[0094] [2-1-2] The second substance contained in the first mixture is a metal salt or metal compound containing a second element which is a platinum group element.

[0095] Examples of the metal salt as the second substance include chlorides, sulfides, hydroxides, oxides, sulfates, bisulfates, oxalates, nitrates, hypochlorites, perchlorates, acetates, and carbonates of the second element, as well as substances containing these compositions. One or more combinations or mixtures selected from these can be used.

[0096] Examples of metal compounds as the second substance include compounds in which at least one molecule of carbon monoxide is coordinated to the first element, compounds containing at least one molecule of a ligand containing a phosphorus atom, compounds containing at least one molecule of a ligand containing a nitrogen atom, and compounds containing at least one molecule of a π-coordinate ligand containing a carbon-carbon double bond, such as a cyclopentadienyl group or a cyclooctadienyl group. One or more of these can be selected and used in combination.

[0097] As the second substance, a hydrate may be used. As the second substance, a combination of the above-mentioned metal salt and metal compound may be used.

[0098] If the second substance contains chlorine, the target catalyst can be obtained in an even higher yield, and the activity of the resulting catalyst can be made even better.

[0099] In particular, this effect is more pronounced when both the first and second substances contain chlorine.

[0100] When producing a catalyst containing rhodium as the second element, the second substance may be rhodium chloride (RhCl ３ ) or its hydrate can be suitably used.

[0101] This allows for obtaining the desired catalyst in higher yields, and also improves the activity of the resulting catalyst.

[0102] The oxidation number of the second element constituting the second substance is preferably between 2 and 4, and preferably 3.

[0103] This allows for obtaining the desired catalyst in higher yields, and also improves the activity of the resulting catalyst.

[0104] When the second substance is dissolved in the first mixture, the concentration of the second element in the solution is preferably 0.1 mmol / kg or more and 5.0 mmol / kg or less, more preferably 0.3 mmol / kg or more and 4.0 mmol / kg or less, and even more preferably 0.7 mmol / kg or more and 3.0 mmol / kg or less.

[0105] This allows for obtaining the desired catalyst in higher yields, and also improves the activity of the resulting catalyst.

[0106] In the aforementioned solution, when the content of the first element is X1' [molecular weight / kg] and the content of the second element is X2' [molecular weight / kg], the value of X2' / X1' is preferably 0.50 or more and 1.00 or less, more preferably 0.60 or more and 1.00 or less, and even more preferably 0.70 or more and 1.00 or less.

[0107] This allows for obtaining the desired catalyst in higher yields, and also improves the activity of the resulting catalyst.

[0108] [2-1-3] The first mixture of substrates contains a substrate. Preferably, this substrate satisfies the conditions described in [1-4] above. This provides the effects described above.

[0109] [2-1-4] The first solvent mixture may further contain a solvent. This allows the first and second substances to be dissolved in the first mixture, improving the handling of the first mixture. Furthermore, in the second mixture preparation step described later, the first mixture and the silicon compound having a silicon-oxygen bond can be mixed more favorably. In addition, the reaction in the reduction step can proceed more favorably.

[0110] Examples of solvents include alcoholic solvents such as methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol; ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as dioxane, tetrahydrofuran, and diglyme; amide solvents such as N,N-dimethylformamide and N,N-dimethylacetamide; aromatic solvents such as benzene and toluene; nitrile solvents such as acetonitrile; and halogenated solvents such as methylene chloride, chloroform, and dichloroethane. One or more of these can be selected and used in combination, with ethanol being particularly preferred. Although halogenated solvents may raise concerns about their impact on human health and the environment, this catalyst can be synthesized without using halogenated solvents.

[0111] This allows the desired reaction to proceed more favorably in the reduction process described later. Furthermore, ethanol is a relatively safe solvent, which is advantageous from the standpoint of worker safety and low environmental impact.

[0112] If the first mixture contains a solvent, the solvent content in the first mixture is preferably 70.0% by mass or more and 99.7% by mass or less, more preferably 96.0% by mass or more and 99.5% by mass or less, and even more preferably 97.0% by mass or more and 99.3% by mass or less.

[0113] This allows the desired reaction to proceed more favorably in the reduction step described later.

[0114] [2-1-5] Other Components The first mixture may contain components other than those described above. Hereafter, in this section ([2-1-5]), such components will be referred to as "other components".

[0115] Other components include, for example, metal salts of platinum group elements other than the first and second elements.

[0116] However, the content of other components in the first mixture is preferably 10.0% by mass or less, more preferably 5.0% by mass or less, and even more preferably 3.0% by mass or less.

[0117] In particular, it is preferable that the content of platinum group elements other than the first and second elements in the first mixture is lower than the sum of the content of the first element and the content of the second element.

[0118] [2-1-6] The first mixture may be obtained by mixing its constituent components at the same time, or by mixing them in multiple stages at different times. More specifically, the first mixture may be obtained, for example, by mixing the first substance, the second substance, and the solvent, and then mixing them with the substrate.

[0119] [2-2] Second Mixture Preparation Step In the second mixture preparation step, the first mixture is mixed with a composition containing a silicon compound having a silicon-oxygen bond to obtain the second mixture.

[0120] The silicon compound contained in the composition used in this process preferably satisfies the conditions described in [1-3] above. This will result in the effects described above.

[0121] The composition used in this process may contain at least a silicon compound, may consist solely of a silicon compound, or may further contain a solvent.

[0122] This allows the desired reaction to proceed more favorably in the reduction step described later.

[0123] The silicon compound content in the composition used in this process is preferably 0.05% by mass or more and 3.0% by mass or less, more preferably 0.07% by mass or more and 2.5% by mass or less, and even more preferably 0.10% by mass or more and 2.0% by mass or less.

[0124] This allows the desired reaction to proceed more favorably in the reduction step described later.

[0125] In this step, the first mixture and the composition containing the silicon compound can be mixed to obtain the second mixture, but it is preferable to add the composition containing the silicon compound dropwise into the first mixture and mix.

[0126] This allows the desired reaction to proceed more favorably in the reduction step described later, and the activity of the resulting catalyst can be improved.

[0127] [2-3] Reduction Process In the reduction process, a reducing agent is used to reduce the first and second substances contained in the second mixture. As a result, the first and second elements contained in the second mixture are reduced to an oxidation state of 0 and precipitate on the substrate.

[0128] The reducing agent can be any substance capable of reducing the first and second substances, such as lithium borohydride (LiBH). ４ ), sodium tetrahydroborate (NaBH ４ ), cerium(III) chloride (CeCl ３ ), sodium cyanoborohydride (NaBH ３ CN), Lithium triethylboron hydride (LiBHEt ３ ), lithium aluminum hydride (LiAlH ４ Examples include diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, Schwartz reagent (bis(cyclopentadienyl)zirconium(IV) chloride hydride), lithium, zinc, hydrazine, ethanol, propanol, alcohols such as ethylene glycol, etc. ４ It is preferable that it contains NaBH ４ An alkaline aqueous solution containing is more preferable.

[0129] This allows the desired reaction in this process to proceed more favorably, and the activity of the resulting catalyst can be improved.

[0130] In this process, the first and second substances contained in the second mixture can be reduced using a reducing agent, but it is preferable to add the composition containing the reducing agent dropwise into the second mixture and mix.

[0131] This allows the desired reaction in this process to proceed more favorably, and the activity of the resulting catalyst can be improved.

[0132] [2-4] Other steps The method for producing the catalyst may include steps other than those described above. Examples of such steps include a step of quenching the excess reducing agent contained in the reaction composition obtained in the reduction step, a step of filtering the reaction product to separate the catalyst as a solid, a step of washing the separated solid, and a step of drying the solid in a wet state.

[0133] [3] Method for producing hydrogenated compounds Next, a method for producing hydrogenated compounds will be described.

[0134] The method for producing the hydrogenated compound of this embodiment comprises a catalyst preparation step of preparing the catalyst described above, and a hydrogenation step of performing hydrogenation on an unsaturated compound (starting compound) having carbon-carbon multiple bonds in its molecule in the presence of the catalyst.

[0135] This allows for the hydrogenation reaction of unsaturated compounds having carbon-carbon multiple bonds in the molecule to proceed favorably, and provides a method for producing hydrogenated compounds that can suitably obtain the desired hydrogenated compound.

[0136] In particular, it is possible to obtain the target compound (hydrogenated compound) in high yield with a small amount of material used, not only in hydrogenation reactions of aliphatic carbon-carbon multiple bonded unsaturated compounds, but also in hydrogenation reactions of a wide range of aromatic compounds, and to proceed with the target catalytic reaction under mild conditions, including room temperature and atmospheric pressure.

[0137] [3-1] Catalyst Preparation Process In the catalyst preparation process, a catalyst is prepared. Preferably, the catalyst prepared in this process satisfies the conditions described above.

[0138] [3-2] Hydrogenation Step In the hydrogenation step, hydrogenation is carried out on an unsaturated compound (starting compound) having carbon-carbon multiple bonds in its molecule in the presence of a catalyst.

[0139] As the unsaturated compound (starting compound), any compound having a carbon-carbon multiple bond in its molecule may be used, and may be an aliphatic compound having an aliphatic carbon-carbon multiple bond (aliphatic unsaturated compound), an aromatic compound having an aromatic carbon-carbon multiple bond (aromatic unsaturated compound), or a compound having both an aliphatic carbon-carbon multiple bond and an aromatic carbon-carbon multiple bond.

[0140] Examples of aliphatic unsaturated compounds having aliphatic carbon-carbon multiple bonds include aliphatic hydrocarbons such as alkenes like ethylene, propylene, and butylene, and alkynes like acetylene, propyne, and butyne, as well as compounds in which functional groups such as hydroxyl groups, carboxyl groups, thiol groups, amino groups, nitro groups, aldehyde groups, sulfo groups, halogen groups, glycidyl groups, ether bonds, ester bonds, thioether bonds, and thioester bonds are introduced to the above aliphatic hydrocarbons. More specifically, examples include unsaturated fatty acids such as oleic acid, linoleic acid, abietic acid, and linolenic acid, terpenes such as pinene (terpenes and compounds in which the above functional groups are introduced to terpenes), rosin resins, terpene resins, butadiene rubber, acrylonitrile butadiene rubber, and polymers containing carbon-carbon multiple bonds such as polydiacetylene.

[0141] Examples of aromatic unsaturated compounds having aromatic carbon-carbon multiple bonds (aromatic unsaturated compounds) include aromatic hydrocarbons such as benzene, toluene, xylene, and naphthalene; aromatic heterocyclic compounds such as furan, pyrrole, thiophene, pyridine, oxazole, imidazole, thiazole, pyrazole, isothiazole, quinoline, isoquinoline, pyridazine, pyrimidine, pyrazine, indole, and purine; compounds in which functional groups such as hydroxyl groups, carboxyl groups, thiol groups, amino groups, nitro groups, aldehyde groups, sulfo groups, halogeno groups, glycidyl groups, ether bonds, ester bonds, thioether bonds, and thioester bonds are introduced to the above aromatic hydrocarbons or aromatic heterocyclic compounds; and aromatic polymers such as polystyrene and polyhydroxystyrene. More specifically, examples include aromatic alcohols such as phenol, cresol, and bisphenol.

[0142] Examples of unsaturated compounds having aliphatic carbon-carbon multiple bonds and aromatic carbon-carbon multiple bonds include styrene-butadiene rubber and styrene-isoprene copolymers.

[0143] In particular, the unsaturated compound (starting compound) is preferably a compound having at least an aromatic carbon-carbon double bond in its molecule.

[0144] With conventional catalysts, hydrogenation reactions involving such unsaturated compounds are particularly difficult. Even when the reaction proceeds, it often requires an extremely large amount of catalyst, resulting in problems such as low yields of the desired reaction product (hydrogenated compound). In contrast, the present invention allows for the acquisition of the desired reaction product (hydrogenated compound) in high yield with a small amount of catalyst, even when using such unsaturated compounds. Therefore, the effects of the present invention are more pronounced when using the aforementioned unsaturated compounds.

[0145] Furthermore, it is preferable that the unsaturated compound (raw material compound) has an aromatic ring, and that the aromatic ring is reduced in the hydrogenation step to change into a saturated alicyclic structure. In particular, it is more preferable that the aromatic ring is a compound having a benzene ring. This further enhances the effects described above.

[0146] Furthermore, it is more preferable that the alcohol is an aromatic alcohol (a compound having a phenolic hydroxyl group). This further enhances the effects described above.

[0147] The amount of catalyst used in this process is preferably 0.0001 mol% to 1.5 mol%, more preferably 0.005 mol% to 1.2 mol%, and even more preferably 0.001 mol% to 0.5 mol% relative to the unsaturated compound (raw material compound).

[0148] This allows the desired reaction to proceed more favorably while reducing the amount of catalyst used, and enables the acquisition of the desired hydrogenated compound in a higher yield.

[0149] This process is typically carried out by incorporating a catalyst into a liquid containing an unsaturated compound (raw material compound), and further incorporating hydrogen gas into the atmosphere or supplying hydrogen gas into the liquid by bubbling or the like.

[0150] By carrying out the reaction in the liquid phase, the desired reaction can proceed more favorably, and the desired hydrogenated compound can be obtained in a higher yield.

[0151] The liquid may further contain a solvent for purposes such as dissolving the unsaturated compound (raw material) or diluting the unsaturated compound (raw material).

[0152] As such solvents, compounds that do not have carbon-carbon multiple bonds in their molecules can be suitably used.

[0153] More specifically, examples of solvents include water; alcoholic solvents such as methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol; ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as dioxane, tetrahydrofuran, and diglyme; amide solvents such as N,N-dimethylformamide and N,N-dimethylacetamide; aromatic solvents such as benzene and toluene; nitrile solvents such as acetonitrile; and halogenated solvents such as methylene chloride, chloroform, and dichloroethane. One or more of these can be selected and used in combination. Furthermore, solvents whose pH has been adjusted with acidic or basic substances may also be used.

[0154] Furthermore, if the unsaturated compound (raw material compound) itself is in liquid form under the conditions of this process, it is not necessary to add a solvent.

[0155] The reaction temperature in this process is preferably 10°C to 150°C, more preferably 15°C to 120°C, and even more preferably 20°C to 100°C.

[0156] This allows the desired reaction to proceed more favorably, and the desired hydrogenated compound can be obtained in a higher yield.

[0157] [3-3] Other steps The method for producing the hydrogenated compound may further include other steps in addition to the steps described above.

[0158] Examples of such processes include replacing the atmosphere in the hydrogenation process with a non-oxidizing atmosphere, and purifying the reaction products obtained in the hydrogenation process.

[0159] [3-4] Regarding the hydrogenated compound (reaction product): The hydrogenated compound obtained by the method for producing the hydrogenated compound of this embodiment may have a structure in which at least a portion of the carbon-carbon multiple bonds that the unsaturated compound (raw material compound) had is reduced by hydrogenation, but it is preferable that it has a chemical structure in which all of the carbon-carbon multiple bonds that the unsaturated compound (raw material compound) had are reduced.

[0160] Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto.

[0161] The present invention will be described in detail below based on specific examples, but the present invention is not limited thereto. In the following examples, processes and measurements where the temperature conditions are not specified were performed at room temperature (23°C).

[0162] [4] Catalyst Manufacturing The catalyst was manufactured as follows.

[0163] (Example A1) First, a 50 mL vial was prepared, and a stirring bar and rhodium chloride trihydrate (25.6 mg, 0.097 mmol), hexahydrate chlorplatinic acid (H) were added to this vial. ２ PtCl ６ 6H ２ O (50.3 mg, 0.097 mmol) and ethanol (5.0 g) were added and the mixture was stirred at room temperature.

[0164] Next, alumina (specific surface area 5 m²) is added to this vial as the substrate. ２ (5.0g) was added and stirred.

[0165] Subsequently, liquid poly(methylhydrosiloxane) (PMHS, 17.5 mg, 0.29 mmol) dissolved in ethanol (4.0 g) was added dropwise to this vial to obtain a suspension.

[0166] To the resulting suspension, add Vensil (NaBH) diluted with ethanol (3.6 g). ４ - An alkaline aqueous solution (Rohm & Haas, 102.3 mg, 0.325 mmol) was slowly added dropwise, and the mixture was then stirred overnight at room temperature.

[0167] Next, 5 mL of water was added to the vial and stirred, yielding a gray suspension. This gray suspension was filtered using quantitative filter paper (5C), and the gray residue was then washed with water. UV measurement of the filtrate confirmed that it did not contain any unreduced precious metals.

[0168] Next, the washed gray residue was vacuum-dried overnight to obtain the catalyst as a dry gray solid.

[0169] The catalyst thus obtained contained Pt as the first element, Rh as the second element, PMHS as a silicon compound having a silicon-oxygen bond, and alumina as a substrate supporting the first element, the second element, and the silicon compound.

[0170] (Example A2) Hydrotalcite (specific surface area 50 m²) was used as the substrate. ２ A catalyst was obtained in the same manner as in Example A1, except that (1 / g, 5.0g) was used.

[0171] (Example A3) The amount of rhodium chloride trihydrate used was 25.6 mg (0.097 mmol), and hexahydrate chlorplatinic acid (H) was added. ２ PtCl ６ 6H ２ A catalyst was obtained in the same manner as in Example A1, except that the amount of O) used was 100.7 mg (0.194 mmol).

[0172] [5] Preparation of hydrogenated compounds (Example B1) A 50 mL flask was prepared, and a stirring bar, the catalyst prepared in Example A1 (300 mg), toluene (0.44 g, 4.7 mmol) as an unsaturated compound having a carbon-carbon multiple bond in its molecule, and cyclohexane (2 mL) as a solvent were added to the flask.

[0173] Subsequently, a diaphragm pump is used to change the atmosphere inside the flask to hydrogen (H ２ The reaction mixture was purged with gas and stirred at room temperature for 12 hours to carry out the hydrogenation reaction. This produced methylcyclohexane, the target hydrogenated compound.

[0174] (Examples B2 and B3) Hydrogenated compounds were produced in the same manner as in Example B1, except that the catalyst produced in Example A2 (300 mg) and the catalyst produced in Example A3 (300 mg) were used instead of the catalyst produced in Example A1.

[0175] (Example B4) A 50 mL flask was prepared, and a stirring bar, the catalyst prepared in Example A1 (500 mg), phenol (457 mg, 4.86 mmol) as an unsaturated compound having carbon-carbon multiple bonds in its molecule, and pure water (2 mL) as a solvent were added to the flask. Then, the atmosphere inside the flask was changed to hydrogen (H) using a diaphragm pump. ２ The reaction mixture was purged with gas and stirred at 50°C for 12 hours to carry out the hydrogenation reaction. This produced cyclohexanol, the target hydrogenated compound.

[0176] (Examples B5 and B6) Hydrogenated compounds were produced in the same manner as in Example B4, except that the catalyst produced in Example A2 (50 mg) and the catalyst produced in Example A3 (500 mg) were used instead of the catalyst produced in Example A1, respectively.

[0177] (Example B7) A 50 mL flask was prepared, and a stirring bar, the catalyst prepared in Example A1 (500 mg), bisphenol A (100 mg, 0.44 mmol) as an unsaturated compound having carbon-carbon multiple bonds in its molecule, and a 1% by mass aqueous solution of HCl (2 mL) as a solvent were added to this flask.

[0178] Subsequently, a diaphragm pump is used to change the atmosphere inside the flask to hydrogen (H ２ The reaction mixture was purged with gas and stirred at 95°C for 24 hours to carry out the hydrogenation reaction. This produced 2,2'-bis(4-hydroxycyclohexyl)propane (hydrogenated bisphenol A), the target hydrogenated compound.

[0179] (Examples B8 and B9) Hydrogenated compounds were produced in the same manner as in Example B7, except that the catalyst produced in Example A2 (50 mg) and the catalyst produced in Example A3 (500 mg) were used instead of the catalyst produced in Example A1, respectively.

[0180] (Example B10) A 50 mL flask was prepared, and a stirring bar, the catalyst prepared in Example A1 (500 mg), bisphenol A diglycidyl ether (150 mg, 0.44 mmol) as an unsaturated compound (aromatic epoxy compound) having a carbon-carbon multiple bond in its molecule, and tetrahydrofuran (2 mL) as a solvent were added to this flask.

[0181] Subsequently, a diaphragm pump is used to change the atmosphere inside the flask to hydrogen (H ２ The reaction mixture was purged with gas and stirred at 50°C for 24 hours to carry out the hydrogenation reaction. This produced the target hydrogenated compound, Hydrogenated bisphenol A diglycidyl ether.

[0182] (Example B11) A hydrogenated compound was produced in the same manner as in Example B10, except that the catalyst produced in Example A1 was replaced with the catalyst (50 mg) produced in Example A2.

[0183] (Example B12) A hydrogenated compound was produced in the same manner as in Example B10, except that the catalyst produced in Example A1 was replaced with the catalyst (500 mg) produced in Example A3, and the reaction time was set to 72 hours.

[0184] (Example B13) A 50 mL flask was prepared, and a stirring bar, the catalyst prepared in Example A1 (500 mg), abietic acid (74 mg, 0.32 mmol) as an unsaturated compound (unsaturated aliphatic compound) having multiple carbon-carbon bonds in its molecule, and tetrahydrofuran (2 mL) as a solvent were added to this flask.

[0185] Subsequently, a diaphragm pump is used to change the atmosphere inside the flask to hydrogen (H ２ The reaction mixture was purged with gas and stirred at 50°C for 24 hours to carry out the hydrogenation reaction. This produced Hydrogenated abietic acid, the target hydrogenated compound.

[0186] (Examples B14 and B15) Hydrogenated compounds were produced in the same manner as in Example B13, except that the catalyst produced in Example A2 (5 mg) and the catalyst produced in Example A3 (500 mg) were used instead of the catalyst produced in Example A1, respectively.

[0187] [6] Evaluation The following evaluations were performed on the above-mentioned examples B1 to B15.

[0188] [6-1] Conversion rate (yield) to the target hydrogenated compound Immediately after the hydrogenation reaction for the predetermined time as described above, the reaction solution is sampled. １ Measurement using H-NMR (solvent: CDCl ３ The conversion rate (yield) from the unsaturated compound used as the raw material to the target hydrogenated compound was calculated using this method.

[0189] These results, along with the catalyst composition and other conditions for Examples B1 to B15, are summarized in Table 1. In Table 1, poly(methylhydrosiloxane) is indicated as "PMHS", hydrotalcite as "MgAlO", 2,2'-bis(4-hydroxycyclohexyl)propane as "HBPA", 2-(4-hydroxycyclohexyl)-2'-(4-hydroxyphenyl)propane as "S-HBPA", bisphenol A diglycidyl ether as "BPA-DE", Hydrogenated bisphenol A diglycidyl ether as "HBPA-DE", Sem-Hydrogenated bisphenol A diglycidyl ether as "S-HBPA-DE", abietic acid as "AA", and Hydrogenated abietic acid as "HAA".

[0190]

[0191] As is clear from Table 1, excellent results were obtained in each example. Furthermore, it was confirmed that the catalyst according to the present invention can suitably carry out hydrogenation reactions with various reaction substrates.

[0192] Furthermore, when a catalyst was produced in the same manner as in the above example, except that the constituent materials of the substrate were changed to silica, hydrotalcite, magnesium lanthanum oxide, zeolite, sulfated zirconia, and activated carbon, and a hydrogenated compound was produced using this catalyst in the same manner as in the above example, excellent results were obtained, similar to those described above.

[0193] Furthermore, the catalyst was manufactured in the same manner as in the above example, except that the content X1 of the first element in the catalyst was varied within the range of 0.1 mmol / g to 4 mmol / g, and the content of the second element in the catalyst was varied within the range of 0.05 mmol / g to 8 mmol / g, thereby varying the value of X2 / X1 within the range of 0.50 to 1.00. When a hydrogenated compound was manufactured using this catalyst in the same manner as in the above example, excellent results were obtained, similar to those described above.

[0194] According to the present invention, it is possible to provide a catalyst that can be suitably used in hydrogenation reactions, a method for producing a catalyst that can be suitably used in hydrogenation reactions, and a method for producing a hydrogenated compound that can suitably proceed with the hydrogenation reaction of an unsaturated compound having carbon-carbon multiple bonds in its molecule, thereby suitably obtaining the desired hydrogenated compound. Therefore, the present invention has industrial applicability.

Claims

1. A catalyst characterized by comprising a first element which is a platinum group element, a second element which is a platinum group element different from the first element, a silicon compound having a silicon-oxygen bond, and a substrate supporting the first element, the second element, and the silicon compound.

2. The catalyst according to claim 1, wherein the silicon compound has a silicon-hydrogen bond.

3. The catalyst according to claim 1 or 2, wherein the first element is Pt.

4. The catalyst according to claim 1 or 2, wherein the second element is Rh.

5. The catalyst according to claim 1 or 2, wherein the silicon compound is a compound having an organic group.

6. The catalyst according to claim 1 or 2, wherein the silicon compound has a plurality of units comprising silicon atoms having a hydrocarbon group and a hydrogen group.

7. The catalyst according to claim 4, wherein the silicon compound is poly(methylhydrosiloxane).

8. The catalyst according to claim 1 or 2, wherein the substrate is a porous body.

9. The catalyst according to claim 8, wherein the substrate is composed of a material comprising at least one selected from the group consisting of alumina, silica, hydrotalcite, magnesium lanthanum oxide, zeolite, sulfated zirconia, and activated carbon.

10. A method for producing a catalyst, comprising: a first mixture preparation step of preparing a first substance as a metal salt or metal compound containing a first element which is a platinum group element; a second substance as a metal salt or metal compound containing a second element which is a platinum group element different from the first element; and a substrate; a second mixture preparation step of mixing the first mixture with a composition containing a silicon compound having a silicon-oxygen bond to obtain a second mixture; and a reduction step of reducing at least one of the first substance and the second substance contained in the second mixture using a reducing agent.

11. The method for producing a catalyst according to claim 10, wherein at least one of the first substance and the second substance contains chlorine.

12. The method for producing a catalyst according to claim 11, wherein the first substance is chloroplatinic acid.

13. The method for producing a catalyst according to claim 10 or 11, wherein the second substance is rhodium chloride.

14. As the reducing agent, NaBH ４ A method for producing a catalyst according to claim 10 or 11, using an alkaline aqueous solution containing the above.

15. A method for producing a hydrogenated compound, comprising: a catalyst preparation step of preparing the catalyst described in claim 1 or 2; and a hydrogenation step of performing hydrogenation on an unsaturated compound having a carbon-carbon multiple bond in its molecule in the presence of the catalyst.

16. The method for producing a hydrogenated compound according to claim 15, wherein the unsaturated compound has an aromatic carbon-carbon double bond, and the carbon-carbon double bond is reduced in the hydrogenation step.

17. The method for producing a hydrogenated compound according to claim 15, wherein the unsaturated compound has an aromatic ring, and the aromatic ring is reduced in the hydrogenation step to change into a saturated alicyclic structure.

18. The method for producing a hydrogenated compound according to claim 17, wherein the aromatic ring has a benzene ring.

19. The method for producing a hydrogenated compound according to claim 15, wherein the hydrogenation step is carried out in a liquid phase at a temperature of 10°C or higher and 150°C or lower.

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