CN101992086A - Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof - Google Patents

Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof Download PDF

Info

Publication number
CN101992086A
CN101992086A CN2009100578167A CN200910057816A CN101992086A CN 101992086 A CN101992086 A CN 101992086A CN 2009100578167 A CN2009100578167 A CN 2009100578167A CN 200910057816 A CN200910057816 A CN 200910057816A CN 101992086 A CN101992086 A CN 101992086A
Authority
CN
China
Prior art keywords
alpha
catalyst
oxide
metal
hydrogen phosphide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN2009100578167A
Other languages
Chinese (zh)
Other versions
CN101992086B (en
Inventor
汪哲明
王辉
马静萌
刘仲能
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sinopec Shanghai Research Institute of Petrochemical Technology
Original Assignee
Sinopec Shanghai Research Institute of Petrochemical Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sinopec Shanghai Research Institute of Petrochemical Technology filed Critical Sinopec Shanghai Research Institute of Petrochemical Technology
Priority to CN2009100578167A priority Critical patent/CN101992086B/en
Publication of CN101992086A publication Critical patent/CN101992086A/en
Application granted granted Critical
Publication of CN101992086B publication Critical patent/CN101992086B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Abstract

The invention relates to a catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and a preparation method thereof, mainly solving the problem of poor Pd catalyst stability in the process of producing the alpha, alpha-dimethyl benzyl alcohol in the prior art. In the invention, the adopted technical scheme is as follows: the catalyst comprises the following components in percentage by weight: (a) 0.1-2.0% of mixture selected from metals or oxides of Pd, (b) 85.0-99.7% of at least one of aluminum oxide and silicon oxide, (c) 0.1-5.0% of at least one of metals or oxides of Sn, Pb or In, and (d) 0.1-10.0% of at least one of metals or oxides of Na, K, Cs, Mg, Ca or Ba. The invention provides the preparation method of the catalyst, thereby better solving the problem in the prior art. The invention can be used for industrially producing the alpha, alpha-dimethyl benzyl alcohol by the hydrogenation of cumene hydroperoxide.

Description

Hydrogen phosphide cumene hydrogenation system α, alpha-alpha-dimethyl benzylalcohol Catalysts and its preparation method
Technical field
The present invention relates to a kind of hydrogen phosphide cumene hydrogenation system α, the Catalysts and its preparation method of alpha-alpha-dimethyl benzylalcohol.
Background technology
α, alpha-alpha-dimethyl benzylalcohol are a kind of important fine chemical materials, can be used for the spices of synthesize hydrogen peroxide diisopropylbenzene (DIPB) and different flavor.Usually industrial, α, alpha-alpha-dimethyl benzylalcohol is produced by sulfide reduction hydrogen phosphide cumene, and the α of Sheng Chaning like this, the alpha-alpha-dimethyl benzylalcohol thing that usually can cure pollutes, and follow-up use is had a negative impact.Produce α by the hydrogen phosphide cumene hydrogenation reaction, alpha-alpha-dimethyl benzylalcohol is a kind of production method of clean environment firendly, and the water that generates in the reaction can be removed by simple lock out operation.
The specific surface that Japan Patent JP55167238 has disclosed a kind of Pd metal reaches 100～200m 2The Pd/Al of/g 2O 3The preparation method, be used for preparing benzalcohol by hydrogenation of hydrogen peroxide cumene reaction, the conversion ratio of hydrogen phosphide cumene can reach 95%.Japan Patent JP61130249 provides a kind of Pd/Al 2O 3Be used for hydrogen phosphide cumene hydrogenation system α, the method for alpha-alpha-dimethyl benzylalcohol, this catalyst adopts the low temperature liquid polymerization process reduction in alkaline medium of hydrazine or formalin, not mentioned modification element in the patent.European patent EP 0378165A2 points out Pd/Al 2O 3Catalyst stable undesirable.
In sum, existing P d/Al 2O 3Be used for the preparing benzalcohol by hydrogenation of hydrogen peroxide cumene production process, having the problem of poor stability.Thereby, developing a kind of hydrogen oxide isopropylbenzene hydrogenation system α of excellent in stability, alpha-alpha-dimethyl benzylalcohol Pd is catalyst based to have essential industry and is worth.
Summary of the invention
One of technical problem to be solved by this invention is that existing technology is being produced α with the hydrogen phosphide cumene for the raw material hydrogenation, in the process of alpha-alpha-dimethyl benzylalcohol, exist the Pd catalyst to stablize bad problem, provide a kind of new hydrogen phosphide cumene hydrogenation to produce α, the catalyst of alpha-alpha-dimethyl benzylalcohol.This catalyst is used for the hydrogen phosphide cumene hydrogenation and produces α, has the advantage of good stability in the alpha-alpha-dimethyl benzylalcohol process.Two of technical problem to be solved by this invention is that a kind of and the Preparation of catalysts method of one of dealing with problems and to adapt will be provided.
For one of solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of hydrogen phosphide cumene hydrogenation system α, the catalyst of alpha-alpha-dimethyl benzylalcohol comprises following component by weight percentage: a) 0.1～2.0% metal or the oxide that is selected from Pd; B) 0.1～5.0% be selected from least a in the metal of Sn, Pb or In or the oxide; C) 0.1～10.0% be selected from least a in the metal of Na, K, Cs, Mg, Ca or Ba or the oxide; D) 85.0～99.7% be selected from least a in aluminium oxide or the silica.
The consumption that is selected from Pd metal or oxide in technique scheme preferable range by weight percentage is 0.1～1.0%; B) the component preferred version is selected from the metal of Sn, Pb or In or the oxide at least two kinds, and by weight percentage, its consumption preferable range is 0.1～2.0%; C) the component preferred version is selected from least a in the metal of Na, K, Mg or Ba or the oxide, and by weight percentage, its consumption preferable range is 0.5～8.0%; C) component more preferably scheme be selected from the metal of Na, K, Mg or Ba or the oxide at least two kinds; D) the specific area preferable range of component is 70～210m 2/ g, the pore volume preferable range is 0.20～0.80mL/g, the average pore size preferable range is 12.0～25.0nm.
For solve the problems of the technologies described above two, the technical solution used in the present invention is as follows: a kind of hydrogen phosphide cumene hydrogenation system α, alpha-alpha-dimethyl benzylalcohol Preparation of catalysts method may further comprise the steps: 1) at least a in aluminium oxide or the silica of being selected from aequum obtains carrier after moulding, drying and 600～1200 ℃ of following roastings; 2) will contain the metal that is selected from Pd or the oxide of aequum, be selected from a kind of, the metal that is selected from Na, K, Cs, Mg, Ca or Ba in Sn, Pb or In metal or the oxide or the solution one or many impregnated carrier of at least a load component in the oxide, obtain catalyst after drying, 500～700 ℃ of roastings.
In the technique scheme, the sintering temperature preferable range that is selected from the step 1) after at least a carrier moulding in aluminium oxide or the silica is 750～1100 ℃, and roasting time is 2～8 hours.The maceration extract of Pd component can be a palladium bichloride, palladium nitrate, the aqueous solution of ammonium chloropalladate or palladous chloride acid ammonium.Other metallic salt can derive from the salt of its solubility.All catalyst can obtain going back the catalyst of ortho states after activation under the atmosphere of hydrogen, this catalyst can be directly used in α, the hydrogenolysis process of alpha-alpha-dimethyl benzylalcohol.
At hydrogen phosphide cumene hydrogenation system α, in the alpha-alpha-dimethyl benzylalcohol process, be converted into α in order to make hydrogen phosphide cumene high conversion, highly selective, alpha-alpha-dimethyl benzylalcohol needs to improve enough, highly active hydrogenation sites.The hydrogenation activity of the hydrogenation sites of catalyst can be adjusted by the load capacity of metal and the decentralization of carried metal.Introduce alkali metal or alkaline-earth metal, can carry out modulation to the electronics of hydrogenation Pd metal and the surface acid alkalescence of structure attribute and carrier, strengthen its hydrogenation performance, the required active sites that reduction or elimination carrier surface bring out side reactions such as polymerization, the stability of raising catalyst.Simultaneously, the meso-hole structure of 12.0～25.0nm size that carrier is suitable helps promoting the diffusion of reactant and product, suppresses side reactions such as polymerization, the carrier duct of knowing clearly is stopped up and the level of coverage of surface-active position thereby alleviate, and can effectively improve the stability of catalyst.Using catalyst of the present invention, is raw material with the hydrogen phosphide cumene, is 1.5MPa in reaction pressure, and reaction temperature is 60 ℃, and volume space velocity is 3.0 hours -1The mol ratio of hydrogen and hydrogen phosphide cumene is 10.0: 1, Determination of Cumene Hydroperoxide Concentration is under 5.0% the process conditions by weight percentage, the conversion ratio that reacts the hydrogen phosphide cumene after 240 hours remains unchanged substantially, α, the selectivity of alpha-alpha-dimethyl benzylalcohol 〉=99.0% is than the conversion ratio and the α of catalyst reaction hydrogen phosphide cumene after 240 hours of prior art for preparing, the selectivity of alpha-alpha-dimethyl benzylalcohol is high by 4～7%, has obtained better technical effect.
The present invention is further elaborated below by embodiment.
The specific embodiment
[embodiment 1]
The Al of moulding 2O 3(specific surface is 208m to obtain carrier in 4 hours through 6 hours, 600 ℃ following roastings of 120 ℃ of dryings 2/ g, pore volume are 0.78mL/g, average pore size 12.5nm).To contain Pb, the Na of aequum and the mixing salt solution impregnated carrier of Pd component, making in 4 hours with 550 ℃ of following roastings in 4 hours through 120 ℃ of dryings is 0.1%Pd-0.1%Pb-0.1%Na/Al by weight percentage 2O 3Catalyst a.
[embodiment 2]
The Al of moulding 2O 3(specific surface is 200m to obtain carrier in 4 hours through 6 hours, 750 ℃ following roastings of 120 ℃ of dryings 2/ g, pore volume are 0.69mL/g, average pore size 13.2nm).To contain behind the mixing salt solution impregnated carrier of Pd, the Sn of aequum and In component 120 ℃ of dryings 4 hours, dipping contains the K of aequum and the mixed liquor impregnated carrier of Mg component again, and making in 4 hours with 550 ℃ of following roastings in 4 hours through 120 ℃ of dryings is 0.5%Pd-2.0%Sn-1.0%In-0.5%K-1.5%Mg/SiO by weight percentage 2Catalyst b.
[embodiment 3]
Al after the moulding 2O 3(specific surface is 75m to obtain carrier in 2 hours through 6 hours, 1200 ℃ following roastings of 120 ℃ of dryings 2/ g, pore volume are 0.28mL/g, average pore size 24.6nm).To contain behind the solution impregnating carrier of Mg component of aequum 120 ℃ of dryings 4 hours, dipping contains the Pd of aequum and the mixed liquor of Pb again, and making in 4 hours with 550 ℃ of following roastings in 4 hours through 120 ℃ of dryings is 0.5%Pd-1.0%Pb-10.0%Mg/Al by weight percentage 2O 3Catalyst c.
[embodiment 4]
The Al of moulding 2O 3(specific surface is 160m to obtain carrier in 5 hours through 6 hours, 900 ℃ following roastings of 120 ℃ of dryings 2/ g, pore volume are 0.58mL/g, average pore size 18.4nm).After dipping being contained the mixing salt solution carrier of Pd, the Cs of aequum and Sn component, made each constituent content in 4 hours in 4 hours, 550 ℃ following roastings of 120 ℃ of dryings and be 1.0%Pd-4.0%Cs-5.0%Sn/Al by weight percentage 2O 3Catalyst d.
[embodiment 5]
The SiO of moulding 2-Al 2O 3(SiO wherein 2Content be 26.0% by weight percentage) (specific surface is 90m to obtain carrier in 4 hours through 6 hours, 1050 ℃ following roastings of 120 ℃ of dryings 2/ g, pore volume are 0.37mL/g, average pore size 22.0nm).After will containing the mixing salt solution impregnated carrier of Pd, the K of aequum and Pb component, made each component in 4 hours with 550 ℃ of following roastings in 4 hours through 120 ℃ of dryings and be 0.5%Pd-1.0%K-2.0%Pb/Al by weight percentage 2O 3Catalyst e.
[embodiment 6]
The SiO of moulding 2(specific surface is 197.0m to obtain carrier in 8 hours through 6 hours, 750 ℃ following roastings of 120 ℃ of dryings 2/ g, pore volume are 0.72mL/g, average pore size 14.5nm).The Pd component solution impregnated carrier that will contain aequum is after 4 hours dryings of 120 ℃ of dryings, flood the mixing salt solution that contains In, Ce, Mg and Ba component of aequum again, made each constituent content in 4 hours with 550 ℃ of following roastings in 4 hours through 120 ℃ of dryings and be 2.0%Pd-3.0%In-1.0%Ce-5.0%Mg-1.0%Ba/SiO by weight percentage 2Catalyst f.
[embodiment 7]
The method that provides according to embodiment 4 prepares catalyst g, and each constituent content is 1.0%Pd-2.0%Sn-2.0%Na-6.0%Mg/Al by weight percentage 2O 3
[embodiment 8]
The method that provides according to embodiment 4 prepares catalyst h, and each constituent content is 0.5%Pd-1.0%Sn-1.5%Na-0.5%Ca-6.0%Ba/Al by weight percentage 2O 3
[embodiment 9]
The method that provides according to embodiment 4 prepares catalyst i, and each constituent content is 0.5%Pd-1.0%In-1.0%Pb-1.0%Na-2.0%K/Al by weight percentage 2O 3
[embodiment 10]
The method that provides according to embodiment 4 prepares catalyst j, and each constituent content is 0.5%Pd-1.0%Sn-5.0%Mg-2.5%Ba/Al by weight percentage 2O 3
[embodiment 11]
The method that provides according to embodiment 4 prepares catalyst k, and each constituent content is 0.5%Pd-0.5%Sn-1.5%Pb-5.0%Mg-2.5%Ba-0.4%K-0.1%Na/Al by weight percentage 2O 3
[embodiment 12]
The method that provides according to embodiment 4 prepares catalyst l, and each constituent content is 0.5%Pd-1.0%Pb-1.0%In-3.0%Mg-4.0%Ba-1.0%K/Al by weight percentage 2O 3
[comparative example 1]
The Al of moulding 2O 3Obtained carrier in 4 hours through 6 hours, 750 ℃ following roastings of 120 ℃ of dryings.After will containing the solution impregnating carrier of Pd component of aequum, made in 4 hours with 500 ℃ of following roastings through 120 ℃ of dryings 4 hours and to be 0.5%Pd/Al by weight percentage 2O 3Catalyst.
[comparative example 2]
The Al of moulding 2O 3Obtain carrier through 6 hours, 750 ℃ roastings in following 4 hours of 120 ℃ of dryings after 4 hours.After will containing the mixed solution impregnated carrier of the Pd of aequum and Sn component, through 120 ℃ of dryings 4 hours with 550 ℃ down in roasting to make in 4 hours be 0.5%Pd-2.0%Sn/Al by weight percentage 2O 3Catalyst.
Before the reaction, all catalyst under hydrogen atmosphere, 400 ℃ of reduction are used for the hydrogen phosphide cumene hydrogenation reaction after 4 hours, appreciation condition is: hydrogen pressure 1.5MPa, 60 ℃ of reaction temperatures, hydrogen/hydrogen phosphide cumene mol ratio is 10, Determination of Cumene Hydroperoxide Concentration is 5.0% by weight percentage, volume space velocity 3.0 hours -1
Table 1 hydrogen phosphide cumene hydrogenation catalyst evaluation result
Figure B2009100578167D0000061
The CHP-hydrogen phosphide cumene; Appreciation condition: hydrogen pressure 1.5MPa, 60 ℃ of reaction temperatures, hydrogen/hydrogen phosphide cumene mol ratio is 10, Determination of Cumene Hydroperoxide Concentration is 5.0% by weight percentage, volume space velocity 3.0 hours -1
As can be seen from Table 1, using catalyst of the present invention, is raw material with the hydrogen phosphide cumene, at hydrogen pressure 1.5MPa, and 60 ℃ of reaction temperatures, volume space velocity 3.0 hours -1The mol ratio of hydrogen and hydrogen phosphide cumene is 10.0, under the process conditions of Determination of Cumene Hydroperoxide Concentration 5.0%, react that the selectivity of hydrogen phosphide cumene remains unchanged substantially after 240 hours, α, the selectivity of alpha-alpha-dimethyl benzylalcohol 〉=99.0% has improved 4.0～7.0% than the selectivity and the conversion ratio of catalyst reaction after 240 hours of prior art for preparing, has obtained better technical effect.

Claims (8)

1. hydrogen phosphide cumene hydrogenation system α, the catalyst of alpha-alpha-dimethyl benzylalcohol comprises following component by weight percentage:
A) 0.1～2.0% metal or the oxide that is selected from Pd;
B) 0.1～5.0% be selected from least a in the metal of Sn, Pb or In or the oxide;
C) 0.1～10.0% be selected from least a in the metal of Na, K, Cs, Mg, Ca or Ba or the oxide;
D) 85.0～99.7% be selected from least a in aluminium oxide or the silica.
2. according to the described hydrogen phosphide cumene of claim 1 hydrogenation system α, the catalyst of alpha-alpha-dimethyl benzylalcohol is characterized in that by weight percentage, and the metal of Pd or the consumption of oxide are 0.1～1.0%.
3. according to the described hydrogen phosphide cumene of claim 1 hydrogenation system α, the catalyst of alpha-alpha-dimethyl benzylalcohol is characterized in that b) component is selected from least two kinds in the metal of Sn, Pb or In or the oxide, and its consumption is 0.1～2.0% by weight percentage.
4. according to the described hydrogen phosphide cumene of claim 1 hydrogenation system α, the catalyst of alpha-alpha-dimethyl benzylalcohol, it is characterized in that c) component wherein is selected from least a in the metal of Na, K, Mg or Ba or the oxide, and its consumption is 0.5～8.0% by weight percentage.
5. according to the described hydrogen phosphide cumene of claim 4 hydrogenation system α, the catalyst of alpha-alpha-dimethyl benzylalcohol is characterized in that c) component is selected from least two kinds in the metal of Na, K, Mg or Ba or the oxide.
6. according to the described hydrogen phosphide cumene of claim 1 hydrogenation system α, the catalyst of alpha-alpha-dimethyl benzylalcohol is characterized in that d) specific surface of component is 70～210m 2/ g, pore volume are 0.20～0.80mL/g, and average pore size is 12.0～25.0nm.
7. the described hydrogen phosphide cumene of claim 1 hydrogenation system α, alpha-alpha-dimethyl benzylalcohol Preparation of catalysts method may further comprise the steps:
1) at least a in aluminium oxide or the silica of being selected from aequum obtains carrier after moulding, drying and 600～1200 ℃ of following roastings;
2) will contain the metal that is selected from Pd or the oxide of aequum, be selected from a kind of, the metal that is selected from Na, K, Cs, Mg, Ca or Ba in Sn, Pb or In metal or the oxide or the solution one or many impregnated carrier of at least a load component in the oxide, obtain catalyst after drying, 500～700 ℃ of roastings.
8. hydrogen phosphide cumene hydrogenation system α according to claim 7, alpha-alpha-dimethyl benzylalcohol Preparation of catalysts method is characterized in that the sintering temperature in the step 1) is 750～1100 ℃, roasting time is 2～8 hours.
CN2009100578167A 2009-08-31 2009-08-31 Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof Active CN101992086B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2009100578167A CN101992086B (en) 2009-08-31 2009-08-31 Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN2009100578167A CN101992086B (en) 2009-08-31 2009-08-31 Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof

Publications (2)

Publication Number Publication Date
CN101992086A true CN101992086A (en) 2011-03-30
CN101992086B CN101992086B (en) 2013-01-09

Family

ID=43783130

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2009100578167A Active CN101992086B (en) 2009-08-31 2009-08-31 Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof

Country Status (1)

Country Link
CN (1) CN101992086B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102040482A (en) * 2009-10-13 2011-05-04 中国石油化工股份有限公司 Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene
CN103539602A (en) * 2012-07-12 2014-01-29 中国石油化工股份有限公司 Method of preparing tetramethyl ethylene by isobutene disproportionation
CN112569931A (en) * 2019-09-27 2021-03-30 中国石油化工股份有限公司 Hydrogenation catalyst, preparation method and application thereof
CN112619634A (en) * 2019-10-08 2021-04-09 中国石油化工股份有限公司 Modified alumina and preparation method and application thereof
CN114433076A (en) * 2020-10-16 2022-05-06 中国石油化工股份有限公司 Supported hydrogenolysis catalyst and preparation method and application thereof
CN114746386A (en) * 2019-11-26 2022-07-12 住友化学株式会社 Method for producing aromatic alcohols

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2024072B3 (en) * 1988-02-11 1992-02-16 Fina Research PROCEDURE TO PREPARE CATALYSTS CONTAINING A METAL FROM THE PLATINUM GROUP, AND ITS USES
JP2819171B2 (en) * 1989-01-13 1998-10-30 三菱化学株式会社 Method for producing aromatic alcohol

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102040482A (en) * 2009-10-13 2011-05-04 中国石油化工股份有限公司 Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene
CN102040482B (en) * 2009-10-13 2013-07-17 中国石油化工股份有限公司 Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene
CN103539602A (en) * 2012-07-12 2014-01-29 中国石油化工股份有限公司 Method of preparing tetramethyl ethylene by isobutene disproportionation
CN103539602B (en) * 2012-07-12 2015-06-10 中国石油化工股份有限公司 Method of preparing tetramethyl ethylene by isobutene disproportionation
CN112569931A (en) * 2019-09-27 2021-03-30 中国石油化工股份有限公司 Hydrogenation catalyst, preparation method and application thereof
CN112569931B (en) * 2019-09-27 2023-01-24 中国石油化工股份有限公司 Hydrogenation catalyst, preparation method and application thereof
CN112619634A (en) * 2019-10-08 2021-04-09 中国石油化工股份有限公司 Modified alumina and preparation method and application thereof
CN112619634B (en) * 2019-10-08 2023-01-24 中国石油化工股份有限公司 Modified alumina and preparation method and application thereof
CN114746386A (en) * 2019-11-26 2022-07-12 住友化学株式会社 Method for producing aromatic alcohols
CN114433076A (en) * 2020-10-16 2022-05-06 中国石油化工股份有限公司 Supported hydrogenolysis catalyst and preparation method and application thereof
CN114433076B (en) * 2020-10-16 2024-02-02 中国石油化工股份有限公司 Supported hydrogenolysis catalyst and preparation method and application thereof

Also Published As

Publication number Publication date
CN101992086B (en) 2013-01-09

Similar Documents

Publication Publication Date Title
CN102040482B (en) Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene
CN101992086B (en) Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof
CN111085199A (en) Catalyst for preparing propylene by propane dehydrogenation and preparation method and application thereof
CN101827653B (en) Catalyst, method for producing the same, and method for producing chlorine using the catalyst
CN101362080B (en) Active carbon loading ruthenium ammonia synthesis catalyst and preparation method thereof
CN104941634B (en) A kind of preparing furan through decarbonylation of furfural palladium carbon catalyst and preparation method thereof
CN105727955B (en) A kind of preparation method of catalyst for hydrogen production from methane vapor reforming
CN105597744A (en) Supported bimetal catalyst, preparation method and applications thereof
CN101817731B (en) Method for preparing polymethoxy dimethyl ether by converting methanol
CN102441400B (en) Preparation method of catalyst in process of producing light olefins by high-activity load type iron-based synthesis gas
CN112934230A (en) Low-Pt long paraffin dehydrogenation catalyst, and preparation method and application thereof
CN105727978B (en) A kind of method for preparing catalyst for making ethylene from ethane oxidative dehydrogenation
CN113244921A (en) Catalyst for preparing formate by catalytic hydrogenation of bicarbonate or carbonate, preparation method and application thereof, and preparation method of formate
CN102389827B (en) Loaded metal hydrogenation catalyst, its preparation method and application in ethylene glycol preparation
Wei et al. Hydrogenation of pentenal over supported Pt nanoparticles: Influence of Lewis-acid sites in the conversion pathway
CN105727954B (en) A kind of preparation method of synthesis gas preparing natural gas catalyst
CN104230643A (en) Preparation method of isopropyl benzene
CN110508277A (en) A kind of high dispersive palladium nanoparticle catalyst and its preparation method and application
CN105642290A (en) Preparation method of catalyst for reforming of methane and carbon dioxide to prepare syngas
CN104230636A (en) Preparation method of ethylbenzene from hydrogenation of low content acetophenone
CN105642289A (en) Preparation method of catalyst for complete methanation of syngas
CN110981728B (en) Preparation method of methyl methacrylate
US10596552B2 (en) Catalyst for preparing cumene and use thereof
CN106475106A (en) A kind of preparation method of synthesis gas preparing natural gas by methanation catalyst
CN102553615B (en) Oxalate hydrogenation copper-gold dual-metal catalyst and preparation method thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant