CN102040482B - Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene - Google Patents
Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene Download PDFInfo
- Publication number
- CN102040482B CN102040482B CN2009102016376A CN200910201637A CN102040482B CN 102040482 B CN102040482 B CN 102040482B CN 2009102016376 A CN2009102016376 A CN 2009102016376A CN 200910201637 A CN200910201637 A CN 200910201637A CN 102040482 B CN102040482 B CN 102040482B
- Authority
- CN
- China
- Prior art keywords
- alpha
- hours
- hydrogen
- phosphide cumene
- 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.)
- Active
Links
Abstract
The invention relates to a method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene, which is mainly used for solving the problem in the existing technology for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating the hydrogen dioxide isopropyl benzene that the Pd catalyst is poor in stability. The technical scheme adopted by the invention is as follows: causing the hydrogen dioxide isopropyl benzene utilized as a raw material to be in contact with catalyst for react under the conditions that the reaction temperature is 40-120 DEG C, the reaction pressure is 0.1-4.0MPa, the volume air speed is 0.2-15.0 h<-1>, and the molar ratio of hydrogen to the hydrogen dioxide isopropyl benzene is (1.5-20.0):1, thus generating the alpha, alpha-dimethyl benzyl alcohol, wherein the adopted catalyst comprises the following components in percentage by weight: a) 0.1-2.0% of mixture of Pd metal or oxide; b) 85.0-99.7% of aluminum oxide or silicon oxide; c) 0.1-5.0% of at least one of metal or oxide of Sn, Pb or In; and d) 0.1-10.0% of at least one of metal or oxide of Na, K, Cs, Mg, Ca or Ba, thus the problem in the prior art is solved, and the method provided by the invention can be used for industrial production of the alpha, alpha-dimethyl benzyl alcohol by hydrogenating the hydrogen dioxide isopropyl benzene.
Description
Technical field
The present invention relates to a kind of hydrogen phosphide cumene hydrogenation α processed, the method for 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 the used different flavor of makeup.Usually, industrial, α, alpha-alpha-dimethyl benzylalcohol produce by the method for sulfide reduction hydrogen phosphide cumene.In order to ensure that hydrogen phosphide cumene fully is reduced, the consumption of sodium sulphite often will surpass theoretical consumption, and the α of Sheng Chaning like this, the alpha-alpha-dimethyl benzylalcohol product thing that usually can cure pollutes, thereby 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 Japanese Patent JP55167238 has disclosed a kind of Pd metal reaches 100～200m
2The Pd/Al of/g
2O
3The preparation method, be used for the preparing benzalcohol by hydrogenation of hydrogen peroxide cumene reaction, the transformation efficiency of hydrogen phosphide cumene can reach 95%.Japanese Patent JP61130249 provides a kind of Pd/Al
2O
3Be used for hydrogen phosphide cumene hydrogenation α processed, the method for alpha-alpha-dimethyl benzylalcohol, this catalyzer adopts the low temperature liquid polymerization process reduction in alkaline medium of hydrazine or formaldehyde solution, not mentioned modification element in the patent.European patent EP 0378165A2 points out Pd/Al
2O
3Catalyzer 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 isopropyl prepared from benzene and hydrogen α of excellent in stability, alpha-alpha-dimethyl benzylalcohol Pd is catalyst based to have essential industry and is worth.
Summary of the invention
Technical problem to be solved by this invention is that existing technology is produced α at the hydrogen phosphide cumene hydrogenation, in the process of alpha-alpha-dimethyl benzylalcohol, the problem of the stable difference of Pd catalyzer, provide a kind of new hydrogen phosphide cumene hydrogenation to produce α, the method of alpha-alpha-dimethyl benzylalcohol, this method have the good advantage of catalyst stability.
For 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 α processed, the method of alpha-alpha-dimethyl benzylalcohol, be raw material with hydrogen phosphide cumene and hydrogen, it is 40～120 ℃ in temperature of reaction, reaction pressure is 0.1～4.0MPa, and the raw material volume space velocity is 0.2～15.0 hour
-1The mol ratio of hydrogen and hydrogen phosphide cumene is 1.5～20.0: 1, the weight concentration of hydrogen phosphide cumene is under 0.5～15.0% the condition, raw material and catalyzer contact reacts are produced α, alpha-alpha-dimethyl benzylalcohol, wherein catalyst system therefor comprises following component by weight percentage: a) 0.1～2.0% metal or the oxide compound 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 compound; C) 0.1～10.0% be selected from least a in the metal of Na, K, Cs, Mg, Ca or Ba or the oxide compound; D) 85.0～99.7% be selected from least a in aluminum oxide or the silicon oxide.
In the technique scheme, the temperature of reaction preferable range is 45～100 ℃, and the reaction pressure preferable range is 0.1～3.0MPa, and raw material volume space velocity preferable range is 0.2～10.0 hour
-1, the mol ratio preferable range of hydrogen and hydrogen phosphide cumene is 2.0～10.0: 1, the weight concentration preferable range of hydrogen phosphide cumene is 1.0～10.0%; The consumption that is selected from the metal of Pd or oxide compound 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 compound 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 compound, and consumption preferable range by weight percentage is 0.5～8.0%; C) component more preferably scheme be selected from the metal of Na, K, Mg or Ba or the oxide compound at least two kinds; Being selected from d) the specific surface area preferable range of component is 70～210m
2/ g, the pore volume preferable range is 0.20～0.80mL/g, the mean pore size preferable range is 12.0～25.0nm.
The Preparation of catalysts method that the present invention relates to is as follows: with the moulding d of aequum) the component drying, after 600～1200 ℃ of following roastings, obtain carrier; The metal that is selected from Pd or the oxide compound that will contain 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 compound or the solution one or many impregnated carrier of at least a load component in the oxide compound, obtain catalyzer through 120 ℃ of dryings, 450～700 ℃ of roastings after 4～8 hours.The maturing temperature preferable range that is selected from after at least a carrier moulding in aluminum oxide or the silicon oxide is 750～1100 ℃, and roasting time is 2～8 hours.The steeping fluid of Pd component can be Palladous chloride, Palladous nitrate, the aqueous solution of ammonium palladic chloride or palladous chloride acid ammonium.Other metallic salt can derive from the salt of its solubility.All catalyzer can obtain going back the catalyzer of ortho states after activation under the atmosphere of hydrogen, this catalyzer can be directly used in α, the hydrogenolysis process of alpha-alpha-dimethyl benzylalcohol.
At hydrogen phosphide cumene hydrogenation α processed, 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 catalyzer can be adjusted by the charge capacity of metal and the dispersity of loaded metal.Introduce basic 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 catalyzer.Simultaneously, 12.0～25.0nm meso-hole structure that carrier is suitable is conducive to promote the diffusion of reactant and product, suppresses side reactions such as polymerization, and the carrier duct of knowing clearly is stopped up and the level of coverage of surfactivity position thereby alleviate, and can effectively improve the stability of catalyzer.Being raw material with the hydrogen phosphide cumene among the present invention, is 0.1～15.0 hour at 40～120 ℃ of temperature of reaction, reaction pressure 0.1～4.0MPa, raw material volume space velocity
-1, the mol ratio of hydrogen and hydrogen phosphide cumene is 1.5～20.0, and the transformation efficiency of hydrogen phosphide cumene is greater than 99.5%, and selectivity is greater than 99.5%.Use catalyzer of the present invention, at hydrogen pressure 1.5MPa, 60 ℃ of temperature of reaction, volume space velocity 3.0 hours
-1The mol ratio of hydrogen and hydrogen phosphide cumene is 10.0, Determination of Cumene Hydroperoxide Concentration is counted with weight percent under 5.0% the processing condition, react hydrogen phosphide cumene after 240 hours selectivity remain unchanged substantially, α, the selectivity of alpha-alpha-dimethyl benzylalcohol 〉=99.0% is than transformation efficiency 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.
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, mean 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
3Catalyzer 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, mean 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 solution 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
2Catalyzer 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, mean 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 solution 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
3Catalyzer 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, mean pore size 18.4nm).After dipping being contained the mixing salt solution carrier of Pd, the Cs of aequum and Sn component, made each component concentration 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
3Catalyzer 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, mean 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
3Catalyzer 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, mean 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 component concentration 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
2Catalyzer f.
[embodiment 7]
The method that provides according to embodiment 4 prepares catalyzer g, and each component concentration 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 catalyzer h, and each component concentration 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 catalyzer i, and each component concentration 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 catalyzer j, and each component concentration 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 catalyzer k, and each component concentration 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 catalyzer l, and each component concentration 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
3Catalyzer.
[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 mixing solutions 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
3Catalyzer.
Before the reaction, all catalyzer 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 temperature of reaction, the mol ratio of hydrogen and hydrogen phosphide cumene 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
The CHP-hydrogen phosphide cumene; Appreciation condition: hydrogen pressure 1.5MPa, 60 ℃ of temperature of reaction, hydrogen/hydrogen phosphide cumene mol ratio is 10.0, Determination of Cumene Hydroperoxide Concentration is 5.0% with weight percent, volume space velocity 3.0 hours
-1
Select catalyzer e among the embodiment 5 for use, just change different examination conditions, its reaction result is listed in table 2
Hydrogen phosphide cumene hydrogenation catalyst evaluation result under the table 2 differential responses condition
| Temperature ℃ | Pressure MPa | H2/ benzylalcohol mol ratio | CHP concentration/% | Air speed hour -1 | CHP transformation efficiency/% | Benzylalcohol selectivity/% |
| 40 | 1.0 | 1.5 | 1.0 | 15.0 | 99.8 | 99.9 |
| 120 | 0.1 | 5.0 | 3.0 | 9.0 | 100.0 | 99.6 |
| 60 | 2.0 | 10.0 | 10.0 | 0.4 | 99.9 | 99.7 |
| 80 | 4.0 | 20.0 | 15.0 | 0.2 | 100.0 | 99.7 |
| 100 | 2.0 | 10.0 | 5.0 | 5.0 | 100.0 | 99.6 |
The CHP-hydrogen phosphide cumene;
From table 1,2 as can be seen, this technology is applied to hydrogen phosphide cumene hydrogenation α processed, and alpha-alpha-dimethyl benzylalcohol process has obtained good reaction result, is 0.2～15.0 hour at 40～120 ℃ of temperature of reaction, reaction pressure 0.1～4.0Mpa, raw material volume space velocity
-1, the mol ratio of hydrogen and hydrogen phosphide cumene is that the transformation efficiency of hydrogen phosphide cumene is greater than 99.5%, α under 1.5～20.0 the processing condition, alpha-alpha-dimethyl benzylalcohol selectivity is greater than 99.5%.Use catalyzer of the present invention, at hydrogen pressure 1.5MPa, 60 ℃ of temperature of reaction, volume space velocity 3.0 hours
-1The mol ratio of hydrogen and hydrogen phosphide cumene is 10.0, Determination of Cumene Hydroperoxide Concentration is counted with weight percent under 5.0% the processing condition, react hydrogen phosphide cumene after 240 hours selectivity remain unchanged substantially, α, the selectivity of alpha-alpha-dimethyl benzylalcohol 〉=99.0% is than transformation efficiency 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.
Claims (1)
1. hydrogen phosphide cumene hydrogenation α processed, the method for alpha-alpha-dimethyl benzylalcohol is raw material with hydrogen phosphide cumene and hydrogen, is 80 ℃ in temperature of reaction, and reaction pressure is 4.0MPa, and the raw material volume space velocity is 0.2 hour
-1The mol ratio of hydrogen and hydrogen phosphide cumene is 20.0: 1, and the weight concentration of hydrogen phosphide cumene is under 15.0% the condition, and the raw material reaction that contacts with catalyzer generates α, alpha-alpha-dimethyl benzylalcohol, wherein used catalyzer comprises following component by weight percentage:
A) 0.5% Pd;
B) 2.0% Pb;
C) 1.0% K;
D) aluminum oxide of surplus;
The Preparation of catalysts method is: the SiO of moulding
2-Al
2O
3, SiO wherein
2Content be 26.0% by weight percentage, obtained carrier in 4 hours through 6 hours, 1050 ℃ following roastings of 120 ℃ of dryings, specific surface is 90 meters
2/ gram, pore volume are 0.37 milliliter/gram, mean pore size 22.0 nanometers; After will containing the mixing salt solution impregnated carrier of Pd, the K of aequum and Pb component, made catalyzer through 120 ℃ of dryings 4 hours in 4 hours with 550 ℃ of following roastings.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102016376A CN102040482B (en) | 2009-10-13 | 2009-10-13 | Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102016376A CN102040482B (en) | 2009-10-13 | 2009-10-13 | Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102040482A CN102040482A (en) | 2011-05-04 |
| CN102040482B true CN102040482B (en) | 2013-07-17 |
Family
ID=43907064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009102016376A Active CN102040482B (en) | 2009-10-13 | 2009-10-13 | Method for preparing alpha, alpha-dimethyl benzyl alcohol by hydrogenating hydrogen dioxide isopropyl benzene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102040482B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103562168B (en) * | 2011-07-15 | 2016-08-17 | Lg化学株式会社 | The preparation method of isopropylbenzene alcohol and the preparation method of phenol, acetone and AMS |
| CN102911015B (en) * | 2011-08-04 | 2015-04-29 | 中国石油化工股份有限公司 | Di-(2-hydroxyl isopropyl) benzene production method |
| CN104549247B (en) * | 2013-10-15 | 2017-07-11 | 中国石油化工股份有限公司 | Hydrocarbon material selective hydrogenation catalyst and preparation method thereof |
| CN107376906B (en) * | 2017-07-24 | 2020-06-02 | 北京恩泽福莱科技有限公司 | Tert-butyl hydroperoxide hydrogenation catalyst, and preparation method and application thereof |
| CN112439401B (en) * | 2019-08-30 | 2022-08-02 | 万华化学集团股份有限公司 | Hydrogenolysis catalyst, preparation method and application thereof in preparation of isopropylbenzene by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| CN112570041B (en) * | 2019-09-27 | 2022-10-11 | 中国石油化工股份有限公司 | Pretreatment method of cumene catalyst, preparation method of cumene and application thereof |
| CN112570040B (en) * | 2019-09-30 | 2022-08-12 | 中国石油化工股份有限公司 | Activation method of cumene catalyst, obtained cumene catalyst and application thereof |
| JP7284692B2 (en) * | 2019-11-26 | 2023-05-31 | 住友化学株式会社 | Method for producing aromatic alcohol |
| CN113070060B (en) * | 2020-01-03 | 2022-08-05 | 万华化学集团股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis of alpha-dimethyl benzyl alcohol and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0378165A2 (en) * | 1989-01-13 | 1990-07-18 | Mitsubishi Petrochemical Co., Ltd. | Method for producing aromatic alcohol |
| CN101992086A (en) * | 2009-08-31 | 2011-03-30 | 中国石油化工股份有限公司上海石油化工研究院 | Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61130249A (en) * | 1984-11-30 | 1986-06-18 | Sumitomo Chem Co Ltd | Production of aromatic alcohol |
-
2009
- 2009-10-13 CN CN2009102016376A patent/CN102040482B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0378165A2 (en) * | 1989-01-13 | 1990-07-18 | Mitsubishi Petrochemical Co., Ltd. | Method for producing aromatic alcohol |
| CN101992086A (en) * | 2009-08-31 | 2011-03-30 | 中国石油化工股份有限公司上海石油化工研究院 | Catalyst for producing alpha, alpha-dimethyl benzyl alcohol by hydrogenation of cumene hydroperoxide and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| JP昭61-130249A 1986.06.18 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102040482A (en) | 2011-05-04 |
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 | |
| CN101362080B (en) | Active carbon loading ruthenium ammonia synthesis catalyst and preparation method thereof | |
| CN104971759A (en) | Preparation method of supported palladium-carbon catalyst | |
| CN1107704C (en) | Selective hydrogenation catalyst for pyrolysis gasoline | |
| CN101237931A (en) | Supported gold catalyst | |
| CN113101945A (en) | Platinum catalyst with core-shell structure as carrier and preparation method thereof | |
| CN101491758A (en) | Catalyst for H2 selective oxidation in styrene production | |
| CN109718787B (en) | Cerium/yttrium stabilized zirconia support and catalyst | |
| CN109529912B (en) | Composite nano-structure copper catalyst for preparing furfuryl alcohol by furfural hydrogenation and preparation method thereof | |
| CN110028382A (en) | A method of preparing sorbierite | |
| CN102040457B (en) | Method for preparing ethylbenzene and styrene by side chain alkylation reaction of phenylmethane and methanol | |
| CN101817731A (en) | Method for preparing polymethoxy dimethyl ether by converting methanol | |
| US10668460B2 (en) | Composite catalyst, method for manufacturing composite catalyst and application thereof | |
| CN103769186B (en) | Anthraquinone hydrogenation catalyst and preparation method thereof | |
| CN106669665A (en) | Integral catalyst for hydrogen peroxide production process through anthraquinone process and preparation method of integral catalyst | |
| CN110773232B (en) | Catalyst for preparing glycol by hydrating alkylene oxide, preparation method and application | |
| CN109851473B (en) | Method for preparing 1,3-propylene glycol by hydrogenolysis of glycerol solution | |
| CN110508277A (en) | A kind of high dispersive palladium nanoparticle catalyst and its preparation method and application | |
| CN104230643A (en) | Preparation method of isopropyl benzene | |
| CN105461500A (en) | Synthetic method for 2-butene through isomerization of 1-butene by catalyzing at room temperature | |
| CN113426475A (en) | Alpha, beta-unsaturated aldehyde ketone hydrogenation catalyst and preparation method thereof | |
| CN106475106A (en) | A kind of preparation method of synthesis gas preparing natural gas by methanation catalyst | |
| US20200070132A1 (en) | PdIn Alloy Catalyst, Method for Manufacturing PdIn Alloy Catalyst and Application Thereof | |
| CN112973676A (en) | Preparation method of supported porous nano platinum catalyst |
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 |