Hydrogenation catalyst and preparation method and application thereof

Abstract

The invention provides a hydrogenation catalyst and a preparation method thereof. The hydrogenation catalyst comprises a noble metal and a carrier for loading the noble metal, wherein the carrier is modified by a polyhydroxy reducing substance. The preparation method of the hydrogenation catalyst comprises the following steps: (1) impregnating a carrier in the polyhydroxy reducing substance, or impregnating the carrier in a solution containing the polyhydroxy reducing substance, and drying to obtain a modified carrier; and (2) dipping the obtained modified carrier in a solution containing a noble metal precursor, carrying out a heating reaction, and drying the product to obtain the hydrogenation catalyst. The invention also provides application of the hydrogenation catalyst in a hydrogenolysis reaction of alpha, alpha-dimethyl benzyl alcohol and a reaction for preparing isopropyl benzene by hydrogenation of alpha-methyl styrene.

Description

Technical Field

[0001] The present invention relates to the field of catalytic technology, and in particular to a hydrogenation catalyst and a preparation method and application thereof. Background Art

[0002] Propylene oxide (PO) is an important organic chemical intermediate, mainly used in the production of polyether polyols, the raw material of polyurethane. At present, the main industrial processes for producing PO are the chlorohydrin method, the co-oxidation method (PO / styrene monomer method, PO / tert-butyl alcohol method, PO / methyl tert-butyl ether method), the cumene hydroperoxide method (CHP method) and the hydrogen peroxide oxidation method (HPPO method).

[0003] Compared with other PO production processes, the CHP PO process has no by-products, is environmentally friendly and requires little investment. It is an environmentally friendly clean production process. The main processes include: cumene oxidation, propylene epoxidation, α,α-dimethylbenzyl alcohol hydrogenolysis (DMBA) and other processes. In theory, this process only consumes propylene, air and hydrogen, and cumene is used as a circulating material. The unit consumption of cumene is a key indicator for evaluating the economy and advancement of the CHP PO process.

[0004] In recent years, the production capacity of newly built PO units at home and abroad is relatively high, ranging from 300,000 tons to 400,000 tons per year. With the expansion of the scale of CHP PO units, DMBA hydrogenolysis technology faces many challenges. Among them, the process of DMBA hydrogenolysis to produce cumene mainly includes two steps, namely, DMBA dehydration to produce α-methylstyrene (AMS) and AMS hydrogenation to obtain the target product cumene. In industry, precious metal Pd is often used as the active metal of the hydrogenolysis catalyst. However, when the AMS hydrogenation activity on the DMBA hydrogenolysis catalyst is insufficient, it will not only cause AMS dimerization to produce heavy components such as cumene, causing an increase in the unit consumption of cumene, but also generate heavy components to cover the active sites of the hydrogenolysis catalyst, resulting in a decrease in catalyst activity.

[0005] Therefore, developing a hydrogenolysis catalyst with high hydrogenation activity can not only reduce the usage of precious metal Pd, but also increase the service life of the catalyst, resulting in higher economic benefits. Summary of the invention

[0006] In order to solve one of the above technical problems existing in the prior art, the present invention provides a hydrogenation catalyst and a preparation method thereof. In the hydrogenation catalyst of the present invention, the active component noble metal has high dispersion, high B acid / L acid ratio, high hydrogenation catalytic activity, and a simple preparation method. The hydrogenation catalyst of the present invention has excellent catalytic performance in double bond hydrogenation, especially in the reaction of preparing isopropylbenzene by hydrogenation of α-methylstyrene.

[0007] A first aspect of the present invention provides a hydrogenation catalyst, comprising a noble metal and a carrier for supporting the noble metal, wherein the carrier is modified with a polyhydroxy reducing substance.

[0008] In some embodiments, the ratio of the amount of B acid (Bronsted acid) to the amount of L acid (Lewis acid) on the carrier is (0.1-0.5):1, for example 0.1:1, 0.2:1, 0.3:1, 0.4:1, 0.5:1 or any value therebetween.

[0009] In some embodiments, in the catalyst, the ratio of the amount of B acid (Bronsted acid) to the amount of L acid (Lewis acid) is (0.1-0.2):1, for example, 0.1:1, 0.12:1, 0.14:1, 0.16:1, 0.18:1, 0.2:1 or any value therebetween.

[0010] In some embodiments, the noble metal includes at least one of Pd, Pt, Ru, Rh, Re, and Ir. In some preferred embodiments, the noble metal includes Pd.

[0011] In some embodiments, the loading amount of the precious metal in the catalyst is 0.01wt% to 5wt%, for example, 0.01wt%, 0.05wt%, 0.1wt%, 0.5wt%, 1wt%, 1.5wt%, 2wt%, 2.5wt%, 3wt%, 3.5wt%, 4wt%, 4.5wt%, 5wt% or any value therebetween, preferably 0.1wt% to 5wt%.

[0012] In some embodiments, the dispersion of the noble metal in the catalyst is not less than 15%.

[0013] In some embodiments, the dispersion of the noble metal in the catalyst is not less than 17%.

[0014] In some embodiments, the dispersion of the noble metal in the catalyst is not less than 19%.

[0015] In some embodiments, the dispersion of the noble metal in the catalyst is 15% to 25%, for example, 15%, 18%, 20%, 22%, 25%, etc.

[0016] In some embodiments, the polyhydroxy reducing substance includes, but is not limited to, a polyol having reducing properties.

[0017] In some preferred embodiments, the polyhydroxy reducing substance includes at least one of C2-C8 (eg, C2, C3, C4, C5, C6, C7, C8, preferably C2-C5) polyols having reducing properties.

[0018] In some preferred embodiments, the polyhydroxy reducing substance includes at least one of ethylene glycol, propylene glycol, and glycerol.

[0019] In some embodiments, the polyhydric reducing substance comprises ethylene glycol.

[0020] In some embodiments, the polyhydric reducing substance comprises glycerol.

[0021] In some embodiments, the carrier includes metal oxides and / or activated carbon. The metal oxides of the present invention include but are not limited to: aluminum oxide, silicon oxide, titanium oxide, zirconium oxide, cerium oxide, etc. In some specific embodiments, the metal oxide includes aluminum oxide.

[0022] The second aspect of the present invention provides a method for preparing the hydrogenation catalyst according to the first aspect, comprising the following steps:

[0023] (1) immersing the carrier in the polyhydroxy reducing substance, or immersing the carrier in a solution containing the polyhydroxy reducing substance, and drying to obtain a modified carrier;

[0024] (2) The obtained modified support is immersed in a solution containing a noble metal precursor and heated for reaction, and the product is dried to obtain the hydrogenation catalyst.

[0025] The method of the present application selects a specific polyhydroxy organic small molecule substance, first uniformly loads it on the surface of a carrier by an impregnation method, modifies the carrier, and then immerses the modified carrier in a precious metal precursor solution and heats it. The polyhydroxy organic small molecule substance selected in the present invention has a certain reducing ability at a certain temperature, and can reduce the precious metal precursor loaded on the surface of the carrier into a precious metal in one step. At the same time, it can also reduce the precious metal precursor in the solution into a precious metal and load it on the surface of the carrier, so that the precious metal has a higher dispersion on the surface of the carrier and improves the catalytic activity.

[0026] In some embodiments, in step (1), the mass ratio of the carrier to the polyhydroxy reducing substance is 1:(0.1-1), for example, 1:0.1, 1:0.15, 1:0.2, 1:0.3, 1:0.35, 1:0.4, 1:0.5, 1:0.6, 1:0.8, 1:1 or any value therebetween, preferably 1:(0.15-0.6).

[0027] In some embodiments, in step (1), in the solution of the polyhydroxy reducing substance, the concentration of the polyhydroxy reducing substance is not less than 20 wt %, preferably 25 wt % to 80 wt %, more preferably 30 wt % to 60 wt %.

[0028] In some embodiments, in step (1), the immersion temperature is 15 to 40° C., and the immersion time is 1 to 48 hours, preferably 6 to 24 hours.

[0029] In some embodiments, in step (1), the drying temperature is 60 to 200°C, preferably 70 to 140°C, and more preferably 100 to 120°C.

[0030] In some embodiments, in step (1), the drying time is 4 to 48 hours, preferably 8 to 24 hours.

[0031] In some embodiments, in step (2), the noble metal precursor comprises at least one of the hydrochloride, nitrate, acetate, sulfate or phosphate of the noble metal. In some embodiments, in step (2), the noble metal precursor comprises at least one of the hydrochloride, nitrate, acetate, sulfate or phosphate of palladium.

[0032] The present application does not impose any particular limitation on the concentration of the noble metal in the solution containing the noble metal precursor, and those skilled in the art may select the concentration according to actual requirements of the loading amount of the noble metal and the immersion time.

[0033] In some embodiments, in step (2), the temperature of the heating reaction is 60-100°C.

[0034] In some embodiments, in step (2), the heating reaction time is 10 to 80 minutes.

[0035] In some embodiments, the method further comprises: in step (2), washing the reaction product after the heating reaction, preferably using deionized water.

[0036] In some embodiments, in step (2), the drying temperature is 60 to 200°C, preferably 60 to 100°C.

[0037] In some embodiments, in step (2), the drying time is 4 to 48 hours, preferably 4 to 24 hours, and more preferably 4 to 12 hours.

[0038] The third aspect of the present invention provides use of the hydrogenation catalyst described in the first aspect or the hydrogenation catalyst obtained by the preparation method described in the second aspect in a double bond hydrogenation catalytic reaction.

[0039] The hydrogenation catalyst of the present invention can be used to catalyze the hydrogenolysis reaction of DMBA, and can especially be used to catalyze the hydrogenation reaction of α-methylstyrene (AMS) to prepare isopropylbenzene.

[0040] Compared with the prior art, the present invention has the following beneficial technical effects:

[0041] 1. The active component of the hydrogenation catalyst of the present invention has a high degree of dispersion of the noble metal, a high B acid / L acid ratio, and a relatively small amount of the noble metal to achieve a relatively high catalytic activity. The catalyst can be used in the hydrogenolysis process of α,α-dimethylbenzyl alcohol, especially in the hydrogenation process of α-methylstyrene. The catalyst still has excellent hydrogenation activity at a relatively high space velocity, and can also reduce the unit consumption of isopropylbenzene in the CHP process for preparing PO, thereby increasing the service life of the catalyst and reducing the cost. The catalyst has a relatively high industrial application value.

[0042] 2. The method for preparing a hydrogenolysis catalyst of the present invention utilizes a hydroxyl-rich reducing substance to first modify the carrier, and the loading and high dispersion of the precious metal on the carrier surface can be achieved through a two-step impregnation method. The prepared catalyst can be used after drying, without the need for high-temperature calcination and activation, and is simple to operate and highly efficient. DETAILED DESCRIPTION

[0043] In order to make the purpose, technical solution and advantages of the present invention more clearly understood, the present invention is further described in detail below in conjunction with embodiments. The specific embodiments described herein are only used to explain the present invention and are not intended to constitute any limitation to the present invention.

[0044] The endpoints and any values ​​of the scope disclosed in the present invention are not limited to the precise scope or value, and these scopes or values ​​should be understood to include values ​​close to these scopes or values. For numerical ranges, the endpoint values ​​of each scope, the endpoint values ​​of each scope and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be regarded as specifically disclosed in this article. Hereinafter, in principle, each technical solution can be combined with each other to obtain a new technical solution, which should also be regarded as specifically disclosed in this article.

[0045] The term "polyhydroxy reducing substance" as used herein refers to a substance containing two or more hydroxyl groups and having a certain reducing property, including but not limited to polyols (including diols) having reducing properties.

[0046] The raw materials used in the following examples and comparative examples of the present invention, unless otherwise specified, can be directly purchased or prepared according to the preparation methods disclosed in the prior art.

[0047] Example 1

[0048] 20g of alumina carrier was wetted with 12.0g of ethylene glycol for 6h, and then the carrier was placed in an oven at 120°C for 12h, and the dried carrier was immersed in an impregnation solution containing a certain amount of palladium, and stirred at 80°C for 30min, and then the catalyst precursor was washed with deionized water several times, and dried in an oven at 100°C for 6h under a nitrogen atmosphere to obtain the finished hydrogenation catalyst Pd1. The theoretical Pd loading in the catalyst is 0.4wt%, and the actual Pd loading in the catalyst is 0.40wt% as detected by inductively coupled plasma emission chromatography. The Pd metal dispersion in the sample was analyzed by hydrogen-oxygen titration and was 20.4%. The B acid and L acid in the carrier and catalyst after ethylene glycol treatment were analyzed by pyridine infrared, where the ratio of B acid to L acid on the carrier after ethylene glycol treatment is 0.32:1, and the ratio of B acid to L acid in the catalyst is 0.15:1.

[0049] Example 2

[0050] 20g of alumina carrier was wetted with 12.0g of ethylene glycol aqueous solution (containing 6.0g of ethylene glycol) for 8h, and then the carrier was placed in an oven at 100°C for 18h, and the dried carrier was immersed in an impregnation solution containing a certain amount of palladium, and stirred at 90°C for 20min, and then the catalyst precursor was washed several times with deionized water, and dried in a vacuum oven at 60°C for 6h to obtain the finished hydrogenation catalyst Pd2. The theoretical Pd loading in the catalyst is 0.4wt%, and the actual Pd loading in the catalyst is 0.4wt% as detected by inductively coupled plasma emission chromatography. The Pd metal dispersion in the sample was analyzed by hydrogen-oxygen titration and was 19.8%. The B acid and L acid in the carrier and catalyst after ethylene glycol treatment were analyzed by pyridine infrared, wherein the ratio of B acid to L acid on the carrier after ethylene glycol treatment is 0.24:1, and the ratio of B acid to L acid in the catalyst is 0.14:1.

[0051] Example 3

[0052] Use 12.0g of ethylene glycol aqueous solution (containing 3.0g of ethylene glycol) to moisten 20g of alumina carrier for 12h, then place the carrier in an oven at 110°C and dry it for 10h, soak the dried carrier in an impregnation solution containing a certain amount of palladium, and stir it at 70°C for 1h, then wash the catalyst precursor with deionized water several times, and dry it in an oven at 100°C in a nitrogen atmosphere for 6h to obtain the finished hydrogenation catalyst Pd3.

[0053] The finished hydrogenation catalyst Pd3 was reduced at 150°C for 8h for reactivation to obtain an activated catalyst, wherein the theoretical Pd loading in the activated catalyst was 0.4wt%; inductively coupled plasma emission chromatography detection found that the actual Pd loading in the catalyst was 0.4wt%; hydrogen oxygen titration analysis showed that the Pd metal dispersion in the sample was 16.7%; pyridine infrared analysis showed that the B acid and L acid in the carrier and catalyst after ethylene glycol treatment had a ratio of 0.17:1 to the B acid on the carrier after ethylene glycol treatment, and a ratio of 0.12:1 to the L acid in the catalyst.

[0054] Example 4

[0055] 20g of alumina carrier was wetted with 12.0g glycerol aqueous solution (containing 7.0g glycerol) for 8h, then the carrier was placed in an oven at 120°C for 8h, the dried carrier was immersed in an impregnation solution containing a certain amount of palladium, and stirred at 80°C for 20min, then the catalyst precursor was washed several times with deionized water, and dried in a vacuum oven at 60°C for 6h, and the finished hydrogenation catalyst Pd4 was obtained. The theoretical Pd loading in the catalyst is 0.4wt%, and the actual Pd loading in the catalyst is 0.4wt% as detected by inductively coupled plasma emission chromatography. The Pd metal dispersion in the sample was analyzed by hydrogen-oxygen titration and was 19.4%. The B acid and L acid in the carrier and catalyst after glycerol treatment were analyzed by pyridine infrared, wherein the ratio of B acid to L acid on the carrier after glycerol treatment is 0.5:1, and the ratio of B acid to L acid in the catalyst is 0.16:1.

[0056] Example 5

[0057] 20 g of alumina carrier was moistened with 12.0 g of aqueous solution containing 4.0 g of citric acid for 12 h, and then the carrier was placed in an oven and dried at 120°C for 10 h. The dried carrier was immersed in an impregnation solution containing a certain amount of palladium and stirred at 80°C for 40 min. The catalyst precursor was then washed several times with deionized water and dried in a vacuum oven at 60°C for 6 h to obtain the finished hydrogenation catalyst Pd5.

[0058] The finished hydrogenation catalyst Pd5 was reduced at 150°C for 8h for reactivation to obtain an activated catalyst, wherein the theoretical Pd loading in the activated catalyst was 0.4wt%; inductively coupled plasma emission chromatography detection found that the actual Pd loading in the catalyst was 0.39wt%; hydrogen oxygen titration analysis showed that the Pd metal dispersion in the sample was 14.5%; pyridine infrared analysis showed that the B acid and L acid in the carrier and catalyst after citric acid treatment showed that the ratio of B acid to L acid on the carrier after citric acid treatment was 0.2:1, and the ratio of B acid to L acid in the catalyst was 0.08:1.

[0059] Comparative Example 1

[0060] 20 g of the alumina carrier was soaked in an impregnation solution containing a certain amount of palladium and stirred at 80° C. for 30 min. The catalyst precursor was then washed several times with deionized water and dried in an oven at 100° C. for 6 h under a nitrogen atmosphere to obtain the finished hydrogenation catalyst Pd1-D.

[0061] The finished hydrogenation catalyst Pd1-D was reduced at 150°C for 8h for reactivation to obtain an activated catalyst, wherein the theoretical Pd loading in the activated catalyst was 0.4wt%; inductively coupled plasma emission chromatography detection found that the actual Pd loading in the catalyst was 0.4wt%; hydrogen oxygen titration analysis showed that the Pd metal dispersion in the sample was 14.4%; pyridine infrared analysis showed that the B acid and L acid in the carrier and the catalyst had a ratio of 0.06:1 to the B acid and 0.075:1 in the catalyst.

[0062] Comparative Example 2

[0063] 20 g of alumina carrier was moistened with 12.0 g of ethanol for 6 h, and then the carrier was placed in an oven at 120° C. to dry for 12 h. The dried carrier was immersed in an impregnation solution containing a certain amount of palladium and stirred at 80° C. for 30 min. The catalyst precursor was then washed several times with deionized water and dried in an oven at 100° C. for 6 h under a nitrogen atmosphere to obtain the finished hydrogenation catalyst Pd2-D.

[0064] The finished hydrogenation catalyst Pd2-D was reduced at 150°C for 8h for reactivation to obtain an activated catalyst, wherein the theoretical Pd loading in the activated catalyst was 0.4wt%; inductively coupled plasma emission chromatography detection found that the actual Pd loading in the catalyst was 0.39wt%; hydrogen oxygen titration analysis showed that the Pd metal dispersion in the sample was 14.2%; pyridine infrared analysis showed that the B acid and L acid in the carrier and catalyst after ethylene glycol treatment showed that the ratio of B acid to L acid on the carrier after ethanol treatment was 0.07:1, and the ratio of B acid to L acid in the catalyst was 0.079:1.

[0065] Comparative Example 3

[0066] 20 g of alumina carrier was impregnated in an impregnation solution containing a certain amount of palladium and 12.0 g of ethylene glycol, and stirred at 80° C. for 30 min. The catalyst precursor was then washed several times with deionized water and dried in an oven at 100° C. for 6 h under a nitrogen atmosphere to obtain the finished hydrogenation catalyst Pd3-D.

[0067] The finished hydrogenation catalyst Pd3-D was reduced at 150°C for 8h for reactivation to obtain an activated catalyst, wherein the theoretical Pd loading in the activated catalyst was 0.4wt%. Inductively coupled plasma emission chromatography detection found that the actual Pd loading in the catalyst was only 0.096wt%, indicating that the precious metal Pd was not effectively loaded on the carrier, resulting in a waste of precious metal. The Pd metal dispersion in the sample was analyzed by hydrogen-oxygen titration and was found to be 21.0%. Pyridine infrared analysis of B acid and L acid in the catalyst showed that the ratio of B acid to L acid in the catalyst was 0.064:1.

[0068] Catalyst Evaluation-Implementation Method 1

[0069] The catalysts prepared in Examples 1-5 and Comparative Examples 1-2 were used to carry out an experiment of hydrogenolysis of DMBA to produce cumene. 20 mL of the catalyst was weighed and loaded into a fixed bed reactor, and then a benzyl alcohol hydrogenolysis experiment was carried out, wherein the catalysts in Examples 3, 5, Comparative Examples 1 and 2 were activated catalysts after reduction at 150° C. for 8 h.

[0070] The benzyl alcohol raw material contains 56.0wt% α,α-dimethylbenzyl alcohol, 1.2wt% acetophenone and 41.7wt% isopropylbenzene, the reaction pressure is 2.0MPa, the inlet temperature is 150℃, the H2 / benzyl alcohol molar ratio is 5.0, and the liquid space velocity is 4h -1 .

[0071] The DMBA content in the product, the molar increment of cumene in the product, the molar increment of cumene in the product, the DMBA conversion rate and the cumene selectivity are shown in Table 1, where the calculation method of "DMBA conversion rate" and "cumene selectivity" is as follows:

[0072] DMBA conversion rate = (DMBA content in raw materials - DMBA content in products) / DMBA content in raw materials;

[0073] Cumene selectivity = cumene molar increase in product / (cumene molar increase in product + 2*cumene molar increase in product + AMS molar increase in product).

[0074] Table 1

[0075]

[0076]

[0077] Catalyst Evaluation-Implementation Method 2

[0078] The AMS hydrogenation experiment was carried out using the catalysts prepared in Examples 1 to 5 and Comparative Examples 1 to 3. The catalysts in Example 3, Example 5, Comparative Example 1 and Comparative Example 2 were activated by reduction at 150° C. for 8 h.

[0079] In an intermittent reactor, 0.3 g of catalyst and 10 g of cumene solution containing 15 wt% AMS were weighed and reacted at 45°C and 0.3 MPa for 15 min. The AMS content in the product and the AMS conversion results are shown in Table 2, where the calculation method of "AMS conversion rate" is as follows:

[0080] AMS conversion rate = (AMS content in raw material - AMS content in product) / AMS content in raw material.

[0081] Table 2

[0082]

[0083] The technical solution of the present invention is not limited to the above-mentioned specific embodiments. All technical variations made according to the technical solution of the present invention fall within the protection scope of the present invention.

Claims

1. A hydrogenation catalyst comprising a noble metal and a carrier for carrying the noble metal, wherein the carrier is modified by a polyhydroxy reducing substance.

2. The hydrogenation catalyst according to claim 1, characterized in that The ratio of the amount of B acid to the amount of L acid on the carrier is (0.1-0.5):1; and / or, The ratio of the amount of B acid to the amount of L acid in the catalyst is (0.1-0.2):

1.

3. The hydrogenation catalyst according to claim 1 or 2, characterized in that The noble metal includes at least one of Pd, Pt, Ru, Rh, Re and Ir, preferably Pd; and / or, The loading amount of the noble metal in the catalyst is 0.01wt% to 5wt%; and / or, The dispersion degree of the noble metal in the catalyst is not less than 15%.

4. The hydrogenation catalyst according to any one of claims 1 to 3, characterized in that The polyhydroxy reducing substance includes a polyol; Preferably, the polyhydroxy reducing substance comprises C2-C5 polyol; Preferably, the polyhydroxy reducing substance includes at least one of ethylene glycol, propylene glycol and glycerol.

5. The hydrogenation catalyst according to any one of claims 1 to 4, characterized in that The carrier includes metal oxide and / or activated carbon. Preferably, the metal oxide includes at least one of aluminum oxide, silicon oxide, titanium oxide, zirconium oxide and cerium oxide.

6. A method for preparing the hydrogenation catalyst according to any one of claims 1 to 5, comprising the following steps: (1) immersing the support in the polyhydroxy reducing substance, or immersing the support in a solution containing the polyhydroxy reducing substance, and drying to obtain a modified support; (2) The obtained modified support is immersed in a solution containing a noble metal precursor and heated for reaction, and the product is dried to obtain the hydrogenation catalyst.

7. The method according to claim 6, characterized in that In step (1), The mass ratio of the carrier to the polyhydroxy reducing substance is 1:(0.1-1), preferably 1:(0.15-0.6); and / or, In the solution of the polyhydroxy reducing substance, the concentration of the polyhydroxy reducing substance is not less than 20wt%, preferably 25wt% to 80wt%, and more preferably 30wt% to 60wt%.

8. The method according to claim 6 or 7, characterized in that: In step (1), The immersion temperature is 15 to 40° C., and the immersion time is 1 to 48 hours; and / or, The drying temperature is 60 to 200° C., preferably 70 to 140° C., and the drying time is 4 to 48 hours.

9. The method according to any one of claims 6 to 8, characterized in that: In step (2), The noble metal precursor includes at least one of a hydrochloride, a nitrate, an acetate, a sulfate or a phosphate of a noble metal; and / or, The temperature of the heating reaction is 60-100° C., and the time of the heating reaction is 10-80 min; and / or, The drying temperature is 60 to 200° C., preferably 60 to 100° C., and the drying time is 4 to 48 hours.

10. Use of the hydrogenation catalyst according to any one of claims 1 to 5 or the hydrogenation catalyst prepared by the method according to any one of claims 6 to 9 in a double bond hydrogenation catalytic reaction; Preferably, the double bond hydrogenation catalytic reaction includes the hydrogenolysis reaction of α,α-dimethylbenzyl alcohol and the hydrogenation reaction of α-methylstyrene to prepare isopropylbenzene.

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