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WO2023134779A1 - Catalyseur d'hydrogénation et son procédé de préparation, et procédé de préparation d'isohexanediol et de méthylisobutylcarbinol - Google Patents

Catalyseur d'hydrogénation et son procédé de préparation, et procédé de préparation d'isohexanediol et de méthylisobutylcarbinol Download PDF

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Publication number
WO2023134779A1
WO2023134779A1 PCT/CN2023/072644 CN2023072644W WO2023134779A1 WO 2023134779 A1 WO2023134779 A1 WO 2023134779A1 CN 2023072644 W CN2023072644 W CN 2023072644W WO 2023134779 A1 WO2023134779 A1 WO 2023134779A1
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Prior art keywords
hydrogenation
catalyst
hydrogenation catalyst
alkaline earth
earth metal
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Chinese (zh)
Inventor
向明林
周冬京
汪永军
丰明
邱长玖
罗文星
佘喜春
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Hunan Changlian New Material Technology Co Ltd
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Hunan Changlian New Material Technology Co Ltd
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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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8926—Copper and noble metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8946—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali or alkaline earth metals
    • 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
    • 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
    • C07C29/136—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 of >C=O containing groups, e.g. —COOH
    • C07C29/143—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 of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—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 of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases

Definitions

  • the present invention relates to the technical field of preparation of isohexanediol and methyl isobutyl carbinol, in particular to a hydrogenation catalyst for preparing isohexanediol and methyl isobutyl carbinol, a preparation method thereof, and preparation of isohexanediol and methyl isobutyl carbinol Methods.
  • Isohexanediol (MPD for short) is a colorless, non-toxic liquid with a slightly fresh sweet smell, soluble in water, alcohol, ether and lower aliphatic hydrocarbons. Isohexanediol has the characteristics of environmental protection, low toxicity, and oil-water miscibility, and can be widely used in various fields such as water-based coatings, PU synthesis, fragrance intermediate synthesis, and pesticide stabilizers.
  • the synthesis method of isohexanediol in China is divided into two types according to the different raw material routes: one is prepared from the methanolysis of 2,4,4,6-tetramethyl-1,3-dioxane; the other is One is to use acetone condensate - diacetone alcohol as raw material for hydrogenation reduction synthesis.
  • the latter method is currently the main synthetic production process.
  • MIBC Methyl isobutyl carbinol
  • MIBC is a medium-boiling solvent with excellent performance, mainly used in the fields of mineral flotation, coating, pesticide, medicine, synthetic resin, cellulose and binder.
  • mineral flotation MIBC is used as a foaming and flotation solvent, which can improve the processing capacity of ore and reduce the amount of foaming agent.
  • foaming agents dispersants, detergents, plasticizers, surfactants, lubricants, cosmetics, and pharmaceuticals for the photographic industry.
  • the existing production routes of methyl isobutyl carbinol mainly include: one is to obtain by-products when synthesizing anti-aging agent 6PPD; the other is to synthesize methyl isobutyl ketone (MIBK) through catalytic hydrogenation of acetone/mesopropylidene Jointly obtained.
  • MIBK methyl isobutyl ketone
  • the product obtained by the former method has low purity and a large amount of impurities, which is difficult to separate and purify, and is not suitable for industrial production.
  • the process route of MIBC is obtained by co-producing MIBK through the catalytic hydrogenation of acetone/mesopropylidene acetone. What you get is a mixture of both.
  • the purpose of the present invention is to provide a method for preparing isohexanediol and methyl isobutyl carbinol in order to overcome the problems of poor catalyst selectivity and limited process raw materials in the existing hydrogenation process route for preparing isohexanediol and methyl isobutyl ketone Hydrogenation catalyst and its preparation method and preparation method of isohexanediol and methyl isobutyl carbinol.
  • acetone in the preparation process of acetone derivatives, acetone can obtain a series of important compounds through condensation reaction and separation and refining process, such as products such as diacetone alcohol and mesityl oxide, and through The acetone condensation reaction liquid containing diacetone alcohol, mesityl oxide and other products is directly subjected to hydrogenation reaction without separation and purification to obtain multiple hydrogenation products at the same time, which has a good technical effect.
  • the present invention was thus obtained.
  • the first aspect of the present invention provides a hydrogenation catalyst for the preparation of isohexanediol and methyl isobutyl carbinol, wherein the hydrogenation catalyst includes a modified carrier, and is loaded on the modified carrier Active components and additive components; wherein, the modified carrier includes alkaline earth metal oxides and carrier oxides, the carrier oxide is aluminum oxide and/or silicon oxide, and the active component is selected from ruthenium, At least one of palladium and platinum, the additive component is copper.
  • a second aspect of the present invention provides a method for preparing a hydrogenation catalyst for isohexanediol and methyl isobutyl carbinol, wherein the method comprises:
  • the modified carrier is contacted with a solution containing an active component element compound and an auxiliary component element compound for impregnation, and the obtained product is subjected to second drying or non-drying and second calcination to obtain a pre-catalyst;
  • the active component is selected from at least ruthenium, palladium and platinum
  • the additive component is copper;
  • the pre-catalyst is contacted with a reducing agent to carry out a reduction reaction to obtain the hydrogenation catalyst.
  • the third aspect of the present invention provides a method for preparing isohexanediol and methyl isobutyl carbinol, wherein the method comprises: hydrogenating the acetone condensation reaction liquid with hydrogen in the presence of a hydrogenation catalyst and hydrogenation conditions, Obtain isohexanediol and methyl isobutyl carbinol;
  • the acetone condensation reaction solution contains diacetone alcohol and mesityl oxide;
  • the hydrogenation catalyst is the hydrogenation catalyst provided by the present invention and/or the hydrogenation catalyst prepared by the method provided by the present invention.
  • the present invention can obtain the following beneficial technical effects:
  • the active component and the co-catalyst copper form an alloy structure, and the synergistic effect between the two can greatly increase the catalytic activity, improve the conversion rate of raw materials and the selectivity of target products, and can reduce the reaction temperature;
  • the pore size of the catalyst is moderate and relatively concentrated, and the reactants and product molecules can quickly enter and exit the catalyst pores, which can avoid the strong adsorption or partial polymerization of the high-boiling fraction generated by the acetone condensation reaction on the surface of the catalyst to cause catalyst deactivation; while the existing nickel Catalysts, high boiling point components have a greater impact on the activity of nickel catalysts;
  • the surface properties of the catalyst can be significantly improved, and the active carbon-carbon double bond and carbon-oxygen double bond can be prevented from forming colloids or other by-products on the surface of the catalyst to block the pores or cover the hydrogenation active sites of the catalyst; At the same time, it also weakens the side reactions of dehydration and bond breaking of the hydroxyl group on the surface of the catalyst, thus greatly improving the selectivity of the catalyst.
  • the first aspect of the present invention provides a hydrogenation catalyst for the preparation of isohexanediol and methyl isobutyl carbinol, wherein the hydrogenation catalyst includes a modified carrier, and an active component and a co-catalyst loaded on the modified carrier agent component; wherein, the modified carrier includes alkaline earth metal oxide and carrier oxide, the carrier oxide is alumina and/or silicon oxide, and the active component is selected from at least one of ruthenium, palladium and platinum One, the additive component is copper.
  • the content of the alkaline earth metal oxide in terms of metal is 0.5-3wt%, preferably 0.5wt%, 1wt%, 1.5wt%, 2wt%, 2.5wt% and 3wt%, and any value in the range formed by any two of the above numerical values.
  • the modified carrier is obtained by introducing alkaline earth metals. The content of the introduced alkaline earth metals is moderate within the above range. If the amount is too small, the catalytic effect will be slightly poor. If the amount is too high, the pore volume of the catalyst will be affected, which cannot meet the requirements for macropores. demand.
  • the alkaline earth metal oxide is at least one selected from magnesium oxide, calcium oxide and barium oxide.
  • the content of the active component is 0.1-3 wt%, and the content of the auxiliary component is 0.1-0.5 wt%, so The content of the modified carrier is 96.5-99.8wt%.
  • the content of the active component is 0.1wt%, 0.2wt%, 0.3wt%, 0.4wt%, 0.5wt%, 0.6wt%, 0.7wt%, 0.8wt%, 0.9wt%, 1wt%, 1.1wt% %, 1.2wt%, 1.3wt%, 1.4wt%, 1.5wt%, 1.6wt%, 1.7wt%, 1.8wt%, 1.9wt%, 2wt%, 2.1wt%, 2.2wt%, 2.3wt%, 2.4 wt%, 2.5wt%, 2.6wt%, 2.7wt%, 2.8wt%, 2.9wt% and 3wt%, and any value in the range formed by any two of the above values; the content of the auxiliary component is 0.1 wt%, 0.2wt%, 0.3wt%, 0.4wt% and 0.5wt%, and any value in the range formed by any two of the above values;
  • the specific surface area of the hydrogenation catalyst is 160-220m 2 /g
  • the pore volume is 0.4-0.7cm 3 /g
  • the volume of pores with a pore diameter of 7-12nm accounts for 55-80% of the total pore volume of the hydrogenation catalyst.
  • the present invention provides a catalyst with the above-mentioned technical characteristics, which can provide better activity of the hydrogenation reaction for preparing isohexanediol and methyl isobutyl carbinol, such as high conversion rate of raw materials and high selectivity of target products, and longer catalyst operation Time, good stability.
  • a second aspect of the present invention provides a method for preparing a hydrogenation catalyst for isohexanediol and methyl isobutyl carbinol, wherein the method comprises:
  • the modified carrier is contacted with a solution containing an active component element compound and an auxiliary component element compound for impregnation, and the obtained product is subjected to second drying or non-drying and second calcination to obtain a pre-catalyst;
  • the active component is selected from at least ruthenium, palladium and platinum
  • the additive component is copper;
  • the pre-catalyst is contacted with a reducing agent to carry out a reduction reaction to obtain the hydrogenation catalyst.
  • the temperature of the first drying is 80-120°C
  • the time of the first drying is 4-20h
  • the first calcined The temperature is 600-950° C.
  • the time for the first calcination is 2-10 hours.
  • the alkaline earth metal compound is selected from at least one of alkaline earth metal inorganic salts, alkaline earth metal organic salts and alkaline earth metal hydroxides, preferably alkaline earth metal nitrates, alkaline earth metal At least one of acetate and alkaline earth metal hydroxide, more preferably at least one of nitrate, acetate and hydroxide of at least one of Mg, Ca and Ba.
  • the amount of the alkaline earth metal compound is such that the content of the alkaline earth metal in the modified support is 0.5-3 wt%. It may be preferably 0.5wt%, 1wt%, 1.5wt%, 2wt%, 2.5wt% and 3wt%, and any value in the range formed by any two of the above numerical values.
  • the carrier may be selected from alumina and/or silicon oxide, and the carrier precursor may be selected from at least one of pseudo-boehmite, alumina powder or silica gel.
  • Both the carrier and the carrier precursor are selected from materials with few small pores and large pores, which may refer to materials with a pore volume greater than 1.0 cm 3 /g, such as large-pore pseudo-boehmite in the field.
  • the small pores refer to substances with a pore volume of less than 0.9 cm 3 /g.
  • the forming may be extruded, pelletized or tableted, so that the strength of the carrier meets the requirements for industrial use.
  • the temperature of the second drying is 80-120°C
  • the time of the second drying is 4-20h
  • the second calcined The temperature is 350-500° C.
  • the time for the second calcination is 4-10 hours.
  • the amount of the active component element compound and the auxiliary component element compound is such that, in the hydrogenation catalyst, based on the total amount of the hydrogenation catalyst, the The content of the active component is 0.1-3wt%, and the content of the auxiliary component is 0.1-0.5wt%.
  • the active component element compound is selected from at least one of nitrate, chloride and acetate of the active component, preferably selected from ruthenium chloride , platinum chloride, palladium acetate at least one.
  • the element compound of the auxiliary component is selected from at least one of sulfate, chloride, nitrate and acetate of the auxiliary component, preferably At least one selected from copper nitrate, copper sulfate and copper chloride or a hydrate thereof.
  • the reducing agent is at least one selected from hydrazine hydrate, sodium borohydride and formaldehyde. It is sufficient to reduce the active component element compound and the auxiliary component element compound into corresponding metal elements.
  • the elemental compound of the active component and the elemental compound of the auxiliary component are calculated as the active component and the auxiliary component respectively, and the reducing agent and the active component and the The molar ratio of the sum of the auxiliary components is 3-6:1.
  • the reduction conditions include: the reduction temperature is 30-80°C, preferably 40-60°C, the reduction time is 2-10h, preferably 4-6h; and non-oxidizing sex atmosphere.
  • the reduction reaction in the step (3) of the present invention also includes drying the obtained product, and the drying can be carried out at a temperature of 60-150°C, preferably at a temperature of 80-120°C.
  • the duration of the drying can be selected according to the drying temperature, whichever can remove or substantially remove the solvent therein. Generally, the duration of the drying may be 8-24 hours, preferably 12-20 hours.
  • the drying is carried out in a non-oxidizing atmosphere, such as a nitrogen atmosphere and/or a zero-group element atmosphere (such as argon).
  • the third aspect of the present invention provides a method for preparing isohexanediol and methyl isobutyl carbinol, wherein the method comprises: hydrogenating the acetone condensation reaction liquid with hydrogen in the presence of a hydrogenation catalyst and hydrogenation conditions, Obtain isohexanediol and methyl isobutyl carbinol;
  • the acetone condensation reaction solution contains diacetone alcohol and mesityl oxide;
  • the hydrogenation catalyst is the hydrogenation catalyst provided by the present invention and/or the hydrogenation catalyst prepared by the method provided by the present invention.
  • the acetone condensation reaction liquid contains acetone, isophorone and impurities.
  • the impurities may be some low molecular weight polymers of acetone.
  • the content of diacetone alcohol is 10-90wt%
  • the content of mesityl oxide is 5-90wt%
  • acetone, isopropylidene is within 5wt%.
  • the ketone condensation reaction solution is a product formed by the condensation reaction of acetone under the condition of a basic catalyst, wherein the temperature of the condensation reaction is 0-80°C, which can be obtained The acetone condensation reaction liquid of above-mentioned composition.
  • the hydrogenation conditions include: The hydrogenation temperature is 50-120°C, the hydrogenation pressure is 1-7MPa, the volume ratio of hydrogen to the acetone condensation reaction liquid is 30-100:1, and the liquid hourly space velocity of the acetone condensation reaction liquid is 0.2-4h - 1 ;
  • the hydrogenation temperature is 60-110°C
  • the hydrogenation pressure is 3-5MPa
  • the volume ratio of hydrogen to the acetone condensation reaction liquid is 40-70:1
  • the liquid hourly space velocity of the acetone condensation reaction liquid is 0.3- 1.8h -1 .
  • the hydrogenation reaction can be carried out in a tubular fixed-bed reactor.
  • the acetone condensation reaction solution is contacted with hydrogen in the reactor, and the acetone condensation reaction solution is contacted with hydrogen.
  • the method can be that the acetone condensation reaction liquid and hydrogen pass through the reactor from top to bottom, and can also pass through the reactor from bottom to top.
  • each metal content parameter in the catalyst is measured by an atomic emission spectrometer; the acetone raw material is a commercial product.
  • the conditions of the hydrogenation reaction include: in the acetone condensation reaction liquid, the content of diacetone alcohol is 90wt%, the content of mesityl oxide is 5wt%, the content of acetone is 3wt%, the content of isophorone is 1.3wt%, and the balance is impurities;
  • the temperature was 85°C
  • the hydrogenation pressure was 5MPa
  • the volume ratio of hydrogen to acetone condensation reaction solution was 30:1
  • the liquid hourly space velocity of the acetone condensation reaction solution was 2h -1 .
  • the reaction results are shown in Table 1.
  • the conditions of the hydrogenation reaction include: in the acetone condensation reaction liquid, the content of diacetone alcohol is 50wt%, the content of mesityl oxide is 46wt%, the content of acetone is 2wt%, the content of isophorone is 1wt%, and the balance is impurities; the hydrogenation temperature is 50 °C, the hydrogenation pressure is 7MPa, the volume ratio of hydrogen to the acetone condensation reaction solution is 100:1, and the liquid hourly space velocity of the acetone condensation reaction solution is 0.5h -1 .
  • the reaction results are shown in Table 1.
  • the conditions of the hydrogenation reaction include: in the acetone condensation reaction liquid, the diacetone alcohol content is 85wt%, the mesityl oxide content is 12wt%, the acetone content is 2wt%, the isophorone content is 0.5wt%, and the balance is impurities; the hydrogenation temperature is 120°C, hydrogenation pressure 1MPa, volume ratio of hydrogen to acetone condensation reaction liquid 50:1, liquid hourly space velocity of acetone condensation reaction liquid 4h -1 , reaction results are shown in Table 1.
  • the conditions of the hydrogenation reaction include: in the acetone condensation reaction liquid, the diacetone alcohol content is 10wt%, the mesityl oxide content is 87wt%, the acetone content is 2wt%, the isophorone content is 0.2wt%, and the balance is impurities; the hydrogenation temperature is 90°C, hydrogenation pressure 3MPa, volume ratio of hydrogen to acetone condensation reaction liquid 45:1, liquid hourly space velocity of acetone condensation reaction liquid 1.5h -1 , reaction results are shown in Table 1.
  • the conditions of the hydrogenation reaction include: the content of diacetone alcohol in the acetone condensation reaction liquid is 90wt%, the content of mesityl oxide is 5wt%, the content of acetone is 3wt%, the content of isophorone is 0.7wt%, and the balance is impurities;
  • the hydrogenation temperature was 115°C
  • the hydrogenation pressure was 5MPa
  • the volume ratio of hydrogen to acetone condensation reaction solution was 70:1
  • the liquid hourly space velocity of the acetone condensation reaction solution was 1.0h -1 .
  • the reaction results are shown in Table 1.
  • the preparation process of the hydrogenation catalyst is the same as that of Example 1, except that the support is not modified by alkaline earth metal Mg.
  • the hydrogenation reaction conditions are the same.
  • the preparation process of the hydrogenation catalyst was the same as in Example 1, except that no Cu additive was added to the catalyst.
  • the hydrogenation reaction conditions are the same.
  • the preparation process of the hydrogenation catalyst is the same as in Example 1, except that the large-pore pseudo-boehmite is replaced by small-pore alumina powder (pore volume less than 0.9 cm 3 /g).
  • the hydrogenation reaction conditions are the same.
  • the catalyst is Ni/Al 2 O 3 , wherein the Ni content is 30wt%.
  • the hydrogenation reaction conditions are the same.
  • the preparation process of the hydrogenation catalyst is the same as that of Comparative Example 2, except that the hydrogenation temperature in the hydrogenation reaction conditions is different, and the hydrogenation temperature is 105°C.
  • Catalyst D of Example 4 was used to investigate the activity and stability of the catalyst.
  • the hydrogenation raw materials were: in the acetone condensation reaction liquid, the content of diacetone alcohol was 86%, the content of mesityl oxide was 10%, the content of acetone was 2%, and the content of isophorone was 0.9% %, the balance is impurities; the conditions of the hydrogenation reaction are: the hydrogenation temperature is 80-90 ° C hydrogenation, the pressure of the acetone condensation reaction liquid is 5MPa, hydrogen and The volume ratio of the acetone condensation reaction solution is 40-60:1, and the liquid hourly space velocity of the acetone condensation reaction solution is 0.8h -1 .
  • the reaction results are shown in Table 2. It can be seen from the running results that the catalyst has good activity, selectivity and high stability.
  • Example 1 and Comparative Example 2 show that the addition of co-catalyst can obviously improve the catalyst activity, acetone conversion rate 100%, isohexanediol and methyl iso The selectivity of butyl alcohol is all higher;
  • the contrast of embodiment 1 and comparative example 1 shows, the addition of alkaline earth metal, the selectivity of isohexanediol rises to 99.9% by 93.3%, the selectivity of methyl isobutyl alcohol by 94.6% % rises to 100%, can obviously improve the selectivity of catalysis;
  • Embodiment 1 and comparative example 3 contrast show, when the catalyzer control pore structure provided by the present invention is in the limited scope, reactant and product molecule can enter and exit catalyst pore rapidly, Thereby the catalytic activity is improved;
  • the comparison of Example 1 and Comparative Example 4 shows that the activity of the nickel catalyst is significantly lower than that of the catalyst of Example 1; the
  • Embodiment 1 comparative example 2 are compared with comparative example 5, as can be seen as adding without co-catalyst, comparative example 5 needs to increase reaction temperature and just can obtain the raw material conversion rate close to embodiment 1, it can be seen that catalyst of the present invention can reduce Hydrogenation reaction temperature to obtain good catalytic activity.

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Abstract

L'invention concerne un catalyseur d'hydrogénation destiné à la préparation d'isohexanediol et de méthylisobutylcarbinol, et son procédé de préparation. De plus, l'invention concerne également un procédé de préparation d'isohexanediol et de méthylisobutylcarbinol. Le catalyseur d'hydrogénation comprend un support modifié, et un composant actif et un composant auxiliaire chargé sur le support modifié ; le support modifié comprend un oxyde de métal alcalino-terreux et un oxyde de support ; l'oxyde de support est de l'oxyde d'aluminium et/ou de l'oxyde de silicium ; le composant actif est au moins un élément choisi parmi le ruthénium, le palladium et le platine ; et le composant auxiliaire est du cuivre. Le catalyseur d'hydrogénation présente une activité élevée, un taux de conversion de matière première élevé, une bonne sélectivité et une bonne stabilité.
PCT/CN2023/072644 2022-01-17 2023-01-17 Catalyseur d'hydrogénation et son procédé de préparation, et procédé de préparation d'isohexanediol et de méthylisobutylcarbinol Ceased WO2023134779A1 (fr)

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CN119114153A (zh) * 2024-09-05 2024-12-13 厦门嘉氢科技有限公司 一种成型Ru催化剂的制备方法及连续化加氢应用
CN119633811A (zh) * 2023-09-15 2025-03-18 中国石油化工股份有限公司 丁腈橡胶加氢催化剂及其制备方法和应用

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CN114369006B (zh) * 2022-01-17 2024-04-12 湖南长炼新材料科技股份公司 一种制备异己二醇和甲基异丁基甲醇的方法

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