CN111185163A - Preparation method and application of catalyst for preparing β -phenethyl alcohol by hydrogenation of styrene oxide - Google Patents

Preparation method and application of catalyst for preparing β -phenethyl alcohol by hydrogenation of styrene oxide Download PDF

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CN111185163A
CN111185163A CN202010105975.6A CN202010105975A CN111185163A CN 111185163 A CN111185163 A CN 111185163A CN 202010105975 A CN202010105975 A CN 202010105975A CN 111185163 A CN111185163 A CN 111185163A
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styrene oxide
hydrogenation
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连奕新
刘毅
刘茜桐
赖伟坤
余姮
刘义云
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Xiamen University
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0207—Pretreatment of the support
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/34—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation
    • B01J37/349—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of flames, plasmas or lasers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts

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Abstract

The invention discloses a preparation method and application of a catalyst for hydrogenating styrene oxide to generate β -phenethyl alcohol, wherein the catalyst adopts alumina spheres modified and pretreated by magnesium oxide as a carrier, PdO as an active component and the content of PdO is 0.5-1.5 wt%PdCl with addition of appropriate amount of dilute hydrochloric acid2The catalyst provided by the invention can be used for the reaction of preparing β -phenethyl alcohol by hydrogenating styrene oxide, can obviously improve the conversion rate of the styrene oxide and the selectivity of β -phenethyl alcohol, is a high-efficiency catalyst, is suitable for the continuous production of a fixed bed, and has better industrial application prospect.

Description

Preparation method and application of catalyst for preparing β -phenethyl alcohol by hydrogenation of styrene oxide
Technical Field
The invention relates to a catalyst for preparing β -phenethyl alcohol by styrene hydrogenation, in particular to a preparation method and application of a catalyst for preparing β -phenethyl alcohol by styrene oxide hydrogenation.
Background
β -phenethyl alcohol is a colorless viscous liquid with soft rose fragrance, and can be used as perfuming agent for cleaning products such as fragrance product, perfume and soap, etc., and also can be used as food additive for bread and tobacco, etc.
β -phenylethyl alcohol can be extracted from rose petal, and can be prepared by various chemical reactions, the main preparation method is as follows:
(1) Friedel-Crafts alkylation to β -phenylethyl alcohol preparation Schaarsschmidt A in 1925 first proposed Friedel-Crafts alkylation of benzene using ethylene oxide and aluminum chloride, by which phenylethanol was directly synthesized, and early representative international patents are JP174230(1949), US2483323(1949), and USSR433121 (1974). however, catalysts used in the Friedel-Crafts alkylation process are corrosive, which means expensive corrosion-resistant equipment is required for the reaction process, and in addition, the process has problems of severe environmental pollution and difficulty in separating the product from the catalyst.
(2) The method utilizes Diels-Alder reaction and dehydrogenation reaction to prepare β -phenethyl alcohol, has high atom utilization rate, does not need to relate to processes such as oxidation reaction, high-pressure hydrogenation reaction and the like, uses water as a solvent in the process of preparing β -phenethyl alcohol, can realize homogeneous reaction, ensures simple and convenient subsequent separation process, is safe and environment-friendly, and accords with the idea of green chemical production.
(3) Synthesizing phenethyl alcohol by a toluene method: the toluene method firstly carries out side chain chlorination on toluene to generate benzyl chloride, then the generated benzyl chloride and sodium cyanide carry out cyanolysis reaction to convert the benzyl chloride into benzyl cyanide, then the benzyl cyanide is converted into benzyl cyanide, and then the benzyl cyanide is reduced to convert into phenethylamine, and finally the benzyl cyanide is converted into phenethyl alcohol. The toluene method requires cyanide in the reaction process, has high toxicity, multiple reaction steps and complex process, and is not suitable for large-scale industrial mass production.
(4) The synthesis method of β -phenethyl alcohol by hydrogenation of styrene oxide is characterized by simple reaction route, no side reaction such as coupling and the like, high yield, less three wastes in the reaction process and the like, and based on the aspects of environmental compatibility and product separation, the hydrogenation of styrene oxide is the preferred synthesis mode for industrially synthesizing β -phenethyl alcohol at present, and the method has the characteristics of high atom utilization rate and simple and convenient operation.
Compared with the traditional process, the heterogeneous catalysis synthesis process is a cleaner choice. Heterogeneous catalytic reactions have been studied extensively to simplify the separation of the catalyst from the reactants and to facilitate continuous operation. The invention adopts a fixed bed reactor to carry out heterogeneous catalytic reaction.
Patent US3579593 describes a method for preparing β -phenylethyl alcohol by using skeletal nickel and palladium as catalysts, however, the method has the problems of high content of by-products (ethylbenzene and phenylacetaldehyde) and low yield of β -phenylethyl alcohol, patent US2822403 discloses a method for preparing β -phenylethyl alcohol by using skeletal nickel and skeletal nickel-cobalt as catalysts and water as solvents and hydrogenating under alkaline conditions, but the process needs a large amount of water, and an emulsifier needs to be added for adjusting the compatibility of water and styrene oxide, which brings great difficulty for later product separation.
In summary, the existing process technologies have certain defects in different degrees, such as low product yield, difficult product separation, high energy consumption and cost, and the like, so that the development of a high-efficiency and high-selectivity catalyst and the realization of the continuous production process of β -phenylethyl alcohol by styrene oxide hydrogenation have important significance.
Disclosure of Invention
The invention aims to provide a preparation method and application of a catalyst for preparing β -phenethyl alcohol by hydrogenating styrene oxide, and the solution scheme of the invention is as follows:
a preparation method of a catalyst for preparing β -phenethyl alcohol by hydrogenation of styrene oxide is characterized in that the catalyst adopts alumina spheres modified and pretreated by magnesium oxide as a carrier, metal PdO is an active component, the content of PdO is 0.5-1.5 wt.%, the content of magnesium oxide is 1-10%, and the balance is alumina, and the preparation method specifically comprises the following steps:
(1) dipping industrial alumina balls in magnesium nitrate solution in advance, and roasting at the constant temperature of 600 ℃ in the air atmosphere to prepare an alumina ball carrier which is subjected to surface modification and heat treatment stabilization of magnesium oxide;
(2) carrying out low-temperature plasma surface modification on the alumina ball carrier prepared in the step (1) in an air atmosphere;
(3) adding the alumina ball carrier subjected to the low-temperature plasma surface modification in the step (2) into PdCl containing diluted hydrochloric acid2Soaking in the solution, filtering, drying the obtained solid, and roasting at a constant temperature of 500 ℃ in an air atmosphere to obtain the catalyst.
Preferably, the impregnation time in step (1) is 8 hours, and the constant temperature calcination is 4 hours.
Preferably, the conditions for performing the low-temperature plasma surface modification in the step (2) under the air atmosphere are that the air flow is 20-100ml/min, the adjusting power is 5-20W, and the treatment time is 10-30 min.
Preferably, the concentration of the dilute hydrochloric acid in the step (3) is 5-10%, and the PdCl is PdCl2The concentration of the solution is 1.5-5mol/L, the dipping time is 8h, the drying temperature is 110 ℃, the drying time is 4h, and the constant-temperature roasting time is 4 h.
The application of catalyst for preparing β -phenylethyl alcohol by hydrogenation of styrene oxide includes such steps as filling the catalyst in fixed-bed reactor, and ordinary-pressure reaction at H2After the reduction activation, continuously introducing hydrogen and slowly increasing pressure, simultaneously cooling the catalyst bed layer to a temperature zone required by the reaction, preheating styrene oxide by a liquid pump body, introducing the preheated styrene oxide into a reactor, carrying out the reaction of preparing β -phenethyl alcohol by hydrogenating the styrene oxide, cooling the reaction product, and collecting the liquid phase product by a cold trap for analysis.
Preferably, the reaction condition for preparing β -phenethyl alcohol by hydrogenating the styrene oxide is that the liquid hourly space velocity of the styrene oxide introduced is 0.5-1.0h-1The space velocity of hydrogen is 500-1500h-1The reaction temperature is 50-300 ℃, and the reaction pressure is 0.5-2.0 MPa.
Preferably, the temperature-programmed activation reduction condition is that under the normal pressure condition, the space velocity of hydrogen is 1500-3000h-1The temperature programming rate is less than 5 ℃/h, the reduction end temperature is 300 ℃, and the constant temperature time is 2h until the reduction activation of the catalyst is finished.
The principle of the invention is as follows:
(1) the reaction process of hydrogenating styrene oxide to β -phenethyl alcohol usually has competition reaction of hydrogenation to generate β -phenethyl alcohol and isomerization to generate phenylacetaldehyde, the acidity of the catalyst is too strong to facilitate the isomerization reaction, the strong acid sites on the surface of the catalyst can be weakened through the surface modification of magnesium oxide, so that the hydrogenation is facilitated to generate β -phenethyl alcohol, and the structural stability of aluminum oxide can be improved through high-temperature heat treatment.
(2) Proper low-temperature plasma carries out surface modification on the alumina ball carrier, can improve the pore channel and the specific surface area of the alumina ball, and can reduce the contact angle of the surface of the carrier and improve the wettability and the hydrophilicity, thereby being beneficial to the dispersion of active components on the surface of the pore channel of the alumina ball and preventing the occurrence of agglomeration.
Compared with the existing catalyst for preparing β -phenethyl alcohol by hydrogenating styrene oxide and the synthesis method of β -phenethyl alcohol, the invention has the following advantages:
(1) the method for preparing β -phenethyl alcohol by hydrogenation of styrene oxide has the advantages of simple preparation process, good catalytic performance, mild reaction conditions, suitability for industrial continuous production and the like.
(2) The method for preparing β -phenethyl alcohol by hydrogenation of styrene oxide provided by the invention has the advantages of excellent catalyst activity and product selectivity, high product yield, mild reaction conditions, low cost, good industrial application prospect and the like.
Detailed Description
The present invention will be described in further detail with reference to examples. It is also to be understood that the following examples are intended to illustrate the present invention and are not to be construed as limiting the scope of the invention, and that the particular materials, reaction times and temperatures, process parameters, etc. listed in the examples are exemplary only and are intended to be exemplary of suitable ranges, and that insubstantial modifications and adaptations of the invention by those skilled in the art in light of the foregoing description are intended to be within the scope of the invention. The examples, where specific techniques or conditions are not indicated, are performed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or instruments used are not indicated by manufacturers, and are all conventional products which can be purchased in the market.
Example 1
The preparation steps of the catalyst are as follows:
(1) dissolving 18.36 g of magnesium nitrate in 60ml of deionized water, stirring to obtain a clear solution, then putting 95g of industrial alumina spheres into the prepared magnesium nitrate solution, soaking for 8 hours, filtering, and roasting the obtained solid at the constant temperature of 600 ℃ for 4 hours in an air atmosphere to obtain the alumina sphere carrier with the surface modified by magnesium oxide and the stable heat treatment, wherein the content of magnesium oxide in the prepared alumina carrier is 5%.
(2) And (2) carrying out low-temperature plasma surface modification on the alumina ball carrier prepared in the step (1) in an air atmosphere, wherein the treatment conditions comprise that the air flow is 20ml/min, the adjusting power is 10W, and the treatment time is 10 min.
(3) 100g of alumina ball carrier after surface modification by low-temperature plasma is soaked in 0.75g of PdCl2Dissolving in 60ml of mixed solution consisting of dilute hydrochloric acid solution with the mass concentration of 5%, soaking for 8 hours, filtering, drying the obtained solid at 110 ℃ for 4 hours, and finally roasting at the constant temperature of 500 ℃ for 4 hours in air atmosphere to obtain the catalyst, which is recorded as Pd-Al2O3(ii) a Wherein the content of PdO in the catalyst is 0.5 wt.%.
Reaction evaluation of catalyst:
1.5g of styrene oxide hydrogenation catalyst Pd-Al2O3Packed in a fixed bed reactor in H2Carrying out temperature programming reduction activation in the atmosphere; the activation procedure is that under the condition of normal pressure, the space velocity of hydrogen is 2000h-1The programmed heating rate is less than 5 ℃/h, the reduction end point temperature is 300 ℃, the constant temperature time is 2h, hydrogen is continuously introduced and the pressure is slowly increased after the reduction activation is finished, the temperature of a catalyst bed layer is reduced to a temperature zone required by the reaction, styrene oxide is preheated by a liquid pump body and then is injected into a reactor, the styrene oxide hydrogenation is carried out to prepare β -phenethyl alcohol, and the specific reaction condition is that the hourly space velocity of the styrene oxide liquid is 0.6h-1Space velocity of hydrogen gas is 1000h-1The reaction temperature is 50 ℃, and the reaction pressure is 1.0 MPa; after the reaction was stabilized, the liquid phase product was collected by a cold trap and analyzed, and the evaluation results are shown in table 1.
Example 2
The catalyst was prepared in the same manner as in example 1 except that the reaction temperature was 100 ℃ in a fixed bed reactor, the reaction conditions were the same as in example 1, and the evaluation results are shown in Table 1.
Example 3
The catalyst was prepared in the same manner as in example 1 except that the reaction temperature was 150 ℃ in a fixed bed reactor, the reaction conditions were the same as in example 1, and the evaluation results are shown in Table 1.
Example 4
The catalyst was prepared in the same manner as in example 1 except that the reaction temperature was 200 ℃ in a fixed bed reactor, the reaction conditions were the same as in example 1, and the evaluation results are shown in Table 1.
Example 5
The catalyst was prepared in the same manner as in example 1 except that the reaction temperature was 250 ℃ in a fixed bed reactor, the reaction conditions were the same as in example 1, and the evaluation results are shown in Table 1.
Example 6
The catalyst was prepared in a similar manner to example 1 except that the amount of magnesium nitrate used in step (1) of example 1 was adjusted to 36.72 g; PdCl in step (3)2The dosage of the hydrochloric acid is adjusted to be 2.25g, the mass concentration of the dilute hydrochloric acid is 10 percent, and the dosage is 100 ml; the catalyst of this example was prepared under otherwise unchanged conditions, wherein the PdO content was 1.5 wt.%. The catalyst evaluation conditions were the same as in example 3, and the evaluation results are shown in Table 1.
Example 7
The preparation method of the catalyst is similar to that of the example 1, except that the treatment conditions for modifying the surface of the low-temperature plasma in the step (2) of the example 1 are that the air flow is 100ml/min, the adjusting power is 5W, the treatment time is 30min, and the catalyst of the example can be prepared under the other conditions, wherein the content of PdO is 0.5 wt.%. The catalyst evaluation conditions were the same as in example 3, and the evaluation results are shown in Table 1.
Example 8
The preparation method of the catalyst is the same as that of example 1, except that in a fixed bed reactor, the reaction temperature is 300 ℃, the reaction pressure is 0.5MPa, the hourly space velocity of the liquid introduced by the styrene oxide is 0.5h < -1 >, the space velocity of hydrogen is 500h < -1 >, and the evaluation results are shown in Table 1.
Example 9
The preparation method of the catalyst is the same as that of example 1, except that in a fixed bed reactor, the reaction temperature is 150 ℃, the reaction pressure is 2.0MPa, the hourly space velocity of the liquid introduced by styrene oxide is 1.0h < -1 >, the space velocity of hydrogen is 1500h < -1 >, and the evaluation results are shown in Table 1.
Comparative example 1
The preparation steps of the catalyst are as follows:
(1) dissolving 18.36 g of magnesium nitrate in 60ml of deionized water, stirring to obtain a clear solution, putting 95g of industrial alumina spheres into the prepared magnesium nitrate solution, soaking for 8 hours, and roasting at 600 ℃ for 4 hours at constant temperature in an air atmosphere to obtain the alumina sphere carrier with the surface modified by magnesium oxide and stabilized by heat treatment, wherein the content of magnesium oxide in the prepared alumina carrier is 5%.
(2) 0.75g of PdCl are weighed out beforehand2Dissolving in 60ml diluted hydrochloric acid solution, soaking 100g of alumina ball carrier stabilized by magnesium oxide surface modification and heat treatment in PdCl added with proper quantity of diluted hydrochloric acid2Soaking in the solution for 8h, drying at 110 ℃ for 4h, and finally roasting at 500 ℃ for 4h in an air atmosphere to obtain the catalyst. Wherein PdCl2The concentration of dilute hydrochloric acid in the solution is 5 percent; the PdO content in the catalyst was made to be 0.5 wt.%.
The catalyst was evaluated in the same manner as in example 3, and the evaluation results are shown in Table 1.
Comparative example 2
The preparation steps of the catalyst are as follows:
(1) 95g of industrial alumina balls are roasted for 4 hours at the constant temperature of 600 ℃ in the air atmosphere to prepare the alumina ball carrier which is stable through heat treatment.
(2) 0.75g of PdCl are weighed out beforehand2Dissolving in 60ml of dilute hydrochloric acid solution, 100g of alumina ball carrier stabilized by heat treatment is immersed in PdCl added with appropriate amount of dilute hydrochloric acid2Soaking in the solution for 8h, drying at 110 ℃ for 4h, and finally roasting at 500 ℃ for 4h in an air atmosphere to obtain the catalyst. Wherein PdCl2The concentration of dilute hydrochloric acid in the solution is 5 percent; the PdO content in the catalyst was made to be 0.5 wt.%.
The catalyst was evaluated in the same manner as in example 3, and the evaluation results are shown in Table 1.
Comparative example 3
The preparation steps of the catalyst are as follows:
(1) 95g of industrial alumina balls are roasted for 4 hours at the constant temperature of 600 ℃ in the air atmosphere to prepare the alumina ball carrier which is stable through heat treatment.
(2) Carrying out low-temperature plasma surface modification on the alumina ball carrier with stable heat treatment in an air atmosphere; wherein the treatment conditions comprise air flow of 20ml/min, power regulation of 10W, and treatment time of 10 min.
(3) 0.75g of PdCl are weighed out beforehand2Dissolving in 60ml of dilute hydrochloric acid solution, 100g of alumina ball carrier stabilized by heat treatment is immersed in PdCl added with appropriate amount of dilute hydrochloric acid2Soaking in the solution for 8h, drying at 110 ℃ for 4h, and finally roasting at 500 ℃ for 4h in an air atmosphere to obtain the catalyst. Wherein PdCl2The concentration of dilute hydrochloric acid in the solution is 5 percent; the PdO content in the catalyst was made to be 0.5 wt.%.
The catalyst was evaluated in the same manner as in example 3, and the evaluation results are shown in Table 1.
Comparative example 4
The preparation steps of the catalyst are as follows:
(1) taking industrial-grade silica sol and pseudo-thin alumina as raw materials, weighing the raw materials according to the Si/Al element molar ratio of 1:2, mixing and grinding the raw materials and the pseudo-thin alumina in a metered manner, kneading the raw materials into strips, drying the strips at 110 ℃, raising the temperature to 600 ℃ in an air atmosphere, and roasting the strips at constant temperature for 4 hours to prepare SiO2-Al2O3A composite oxide support.
(2) 0.75g of PdCl are weighed out beforehand2Dissolving in 60ml of dilute hydrochloric acid solution, 100g of heat-treated SiO2-Al2O3The composite oxide carrier is soaked in PdCl with proper amount of dilute hydrochloric acid2Soaking in the solution for 8h, drying at 110 ℃ for 4h, and finally roasting at 500 ℃ for 4h in a nitrogen atmosphere to obtain the catalyst. Wherein PdCl2The concentration of dilute hydrochloric acid in the solution is 5 percent; the PdO content in the catalyst was made to be 0.5 wt.%.
The catalyst was evaluated in the same manner as in example 3, and the evaluation results are shown in Table 1.
Comparative example 5
The preparation steps of the catalyst are as follows:
(1) the industrial granular activated carbon is used as a carrier, washed by 10% dilute nitric acid, dried at 110 ℃, programmed to 600 ℃ in nitrogen atmosphere and roasted at constant temperature for 4 hours to prepare the activated carbon carrier.
(2) 0.75g of PdCl are weighed out beforehand2Dissolving in 60ml diluted hydrochloric acid solution, soaking 100g of heat-treated activated carbon carrier in PdCl added with proper amount of diluted hydrochloric acid2Soaking in the solution for 8h, drying at 110 ℃ for 4h, and finally roasting at 500 ℃ for 4h in a nitrogen atmosphere to obtain the catalyst. Wherein PdCl2The concentration of dilute hydrochloric acid in the solution is 5 percent; the PdO content in the catalyst was made to be 0.5 wt.%.
The catalyst was evaluated in the same manner as in example 3, and the evaluation results are shown in Table 1.
Table 1 evaluation results of catalytic performance of catalysts prepared in examples and comparative examples
Figure BDA0002387821590000081

Claims (7)

1. A preparation method of a catalyst for preparing β -phenethyl alcohol by hydrogenation of styrene oxide is characterized in that the catalyst adopts alumina spheres modified and pretreated by magnesium oxide as a carrier, metal PdO is an active component, the content of PdO is 0.5-1.5 wt.%, the content of magnesium oxide is 1-10%, and the balance is alumina, and the preparation method specifically comprises the following steps:
(1) dipping industrial alumina balls in magnesium nitrate solution in advance, and roasting at the constant temperature of 600 ℃ in the air atmosphere to prepare an alumina ball carrier which is subjected to surface modification and heat treatment stabilization of magnesium oxide;
(2) carrying out low-temperature plasma surface modification on the alumina ball carrier prepared in the step (1) in an air atmosphere;
(3) adding the alumina ball carrier subjected to the low-temperature plasma surface modification in the step (2) into PdCl containing diluted hydrochloric acid2Soaking in the solution, filtering, drying the obtained solid, and roasting at a constant temperature of 500 ℃ in an air atmosphere to obtain the catalyst.
2. The method for preparing the catalyst used in the hydrogenation of styrene oxide to β -phenylethyl alcohol according to claim 1, wherein the impregnation time in step (1) is 8 hours, and the constant temperature calcination is 4 hours.
3. The method for preparing β -phenylethyl alcohol by hydrogenation of styrene oxide according to claim 1, wherein the low temperature plasma surface modification in step (2) is carried out under the conditions of air flow rate of 20-100ml/min, regulation power of 5-20W and treatment time of 10-30 min.
4. The method for preparing the catalyst used in the hydrogenation of styrene oxide to β -phenylethyl alcohol according to claim 1, wherein the concentration of the dilute hydrochloric acid in the step (3) is 5-10%, and the PdCl is PdCl2The concentration of the solution is 1.5-5mol/L, the dipping time is 8h, the drying temperature is 110 ℃, the drying time is 4h, and the constant-temperature roasting time is 4 h.
5. The application of catalyst for preparing β -phenethyl alcohol by hydrogenation of styrene oxide is characterized by comprising the following specific steps of filling styrene oxide hydrogenation catalyst in a fixed bed reactor at normal pressure and H2After the reduction activation, continuously introducing hydrogen and slowly increasing pressure, simultaneously cooling the catalyst bed layer to a temperature zone required by the reaction, preheating styrene oxide by a liquid pump body, introducing the preheated styrene oxide into a reactor, carrying out the reaction of preparing β -phenethyl alcohol by hydrogenating the styrene oxide, cooling the reaction product, and collecting the liquid phase product by a cold trap for analysis.
6. The application of the catalyst for hydrogenation of styrene oxide to β -phenylethyl alcohol according to claim 5, wherein the reaction conditions for hydrogenation of styrene oxide to β -phenylethyl alcohol are that the liquid hourly space velocity of the introduced styrene oxide is 0.5-1.0h-1The space velocity of hydrogen is 500-1500h-1The reaction temperature is 50-300 ℃, and the reaction pressure is 0.5-2.0 MPa.
7. According toThe use of the catalyst in the hydrogenation of styrene oxide to β -phenylethyl alcohol as claimed in claim 5, wherein the temperature-programmed reduction activation condition is that under normal pressure, the space velocity of hydrogen is 1500--1The temperature programming rate is less than 5 ℃/h, the reduction end temperature is 300 ℃, and the constant temperature time is 2h until the reduction activation of the catalyst is finished.
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