CN104226354A - Catalyst for preparing isopropanol by hydrogenating acetone as well as preparation method and application thereof - Google Patents
Catalyst for preparing isopropanol by hydrogenating acetone as well as preparation method and application thereof Download PDFInfo
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- CN104226354A CN104226354A CN201410431463.3A CN201410431463A CN104226354A CN 104226354 A CN104226354 A CN 104226354A CN 201410431463 A CN201410431463 A CN 201410431463A CN 104226354 A CN104226354 A CN 104226354A
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Abstract
The invention relates to a catalyst for preparing isopropanol by hydrogenating acetone. The catalyst comprises the following ingredients by weight percent: 10 to 30 percent of metal oxide, 0.5 to 2 percent of metal carbonate, and 68 to 89.5 percent of carrier. The catalyst has advantages of simple production method, low price, high activity and selectivity and simplicity in operation.
Description
Technical field
The present invention relates to a kind of catalyst for acetone hydrogenation preparing isopropanol and preparation method and application.
Background technology
Industrial isopropyl alcohol can be obtained by fermentation and propylene hydration two kinds of methods, consider that the technique that the economy of process mainly adopts at present is propylene hydration method, namely propylene and sulfuric acid reaction first obtain sulfuric acid isopropyl ester, the latter forms isopropyl alcohol or propylene and water through hydrolysis and heats in the presence of a catalyst, pressurizes and carry out hydration reaction generation isopropyl alcohol, but the conversion per pass of this process propylene is lower, and there is certain pollution to environment.In recent years, along with the field such as coating, ink increases fast to isopropyl alcohol demand, the raw materials for production propylene of this technique the is occurred situation of obvious undersupply.
Acetone mainly obtains (with phenol coproduction) by isopropylbenzene peroxidating method, due to the increase of phenol demand, produce a large amount of acetone and cause acetone market saturation, its price is significantly less than isopropyl alcohol, therefore be isopropyl alcohol by hydrogenation by acetone conversion be a route very with feasibility economically, acetone hydrogenation process product is simple, no coupling product in course of reaction in theory, and therefore this process environments is friendly and have very high Atom economy.
According to bibliographical information, transition-metal catalyst catalyst has excellent catalytic activity for this reaction, noble metal as palladium, platinum, rhodium, ruthenium and base metal as nickel, cobalt etc. are all successively in the news for this reaction, compared to noble metal catalyst, non-noble metal-based catalysts has the advantage such as low price, reaction condition gentleness, has huge commercial Application potentiality.In the flat 3-141235 of Japanese Laid-Open Patent, when adopting Raney's nickel to be hydrogenation catalyst, the conversion ratio of acetone and the selective of isopropyl alcohol all reach more than 99%, but Raney's nickel is comparatively complicated when Catalyst packing, be unfavorable for applying for its heavy industrialization, produce the novel non-noble metal catalyst therefore developed for this reaction and be of great significance.
Summary of the invention
The object of the present invention is to provide a kind of method for making is simple, cheap, activity and selectivity is high and the simple to operate catalyst for acetone hydrogenation preparing isopropanol and preparation method and application.
Compared to bulk phase catalyst, loaded catalyst has some obvious advantages.Such as metal simple-substance component is carried on as after on the carrier such as aluminium oxide, silica, on the one hand because these carriers have larger specific area, can dispersed metal nano particle preferably, improve metal nanoparticle stability at reaction conditions, suppress the sintering deactivation of catalyst, these carriers have abundant pore passage structure on the other hand, are conducive to the mass transfer in course of reaction and heat transfer, can effectively improve the selective of target product, suppress the generation of side reaction.Secondly, the type catalyst preparation process is simple, and low price, greatly reduces the content of metal in catalyst, and be easy to processing and filling use, catalyst, under comparatively gentle reaction condition, just can obtain higher reactivity simultaneously.
Metal nanoparticle and metal carbides nano particle are carried on the carrier of high surface area by the present invention, and this catalyst just has very excellent acetone hydrogenation preparing isopropanol performance under very gentle reaction condition.
The weight ratio of catalyst of the present invention consists of:
Activity component metal oxide content is 10-30%, and metal carbides content is 0.5%-2%, and vector contg is 68-89.5%.
Metal oxide as above is NiO, Co
3o
4or Fe
2o
3deng transition metal oxide.
Metal carbides described above are tungsten carbide or molybdenum carbide one or both mixture wherein.
If above-mentioned carrier is SiO
2, molecular sieve, SBA-15, alundum (Al2O3), zirconium dioxide or diatomite etc.
The preparation method of catalyst of the present invention is:
(1) carrier is warming up to 500-800 DEG C of roasting 6-8 h with 1-3 DEG C/min, is then down to room temperature and obtains pretreated carrier;
(2) soluble metal carbide precursor salt is configured to the aqueous solution of 0.1-2mol/L, by catalyst composition by configuration after solution impregnation on pretreated carrier, dip time is 6-12, then evaporate to dryness in the water-bath of 70-100 DEG C, the sample that obtains is placed in the 100-120 DEG C of dry 8-24h of baking oven, obtains the carrier of carried metal carbide predecessor;
(3) will the carrier of carried metal carbide predecessor be obtained at lower carbon number hydrocarbons, or press CO and H
2volume ratio is that 1-5:10 forms carbonization in the carbonization medium of gaseous mixture, and be warming up to 600-800 DEG C with 0.5-2 DEG C/min, carbonization 3-9h, the air speed of carbonization gas is 3000-8000h
-1, the pressure of carbonization gas is 0.1-0.5MPa, is 0.5-2.5%O in volume ratio after being down to room temperature
2in/Ar gaseous mixture after passivation 6-10, obtain the carrier of load carbide;
(4) the active component precursor salt of solubility is configured to the aqueous solution of 0.1-2mol/L by the composition of catalyst, to be configured to the aqueous solution is added drop-wise on the carrier that obtains in step (3), after 100-120 DEG C of dry 10-24h, under the inert atmospheres such as He or Ar, 400-600 DEG C of roasting 4-6 h is warming up to 0.5-2 DEG C/min, metal nitrate obtains metal oxide through decomposition, and sample is obtained catalyst after being cooled to room temperature.
The metal carbides precursor salt of solubility as above is ammonium molybdate, ammonium metatungstate, sodium tungstate etc.The active component predecessor of solubility is nickel nitrate, citric acid nickel, cobalt nitrate, cobalt acetate, ferric nitrate, ferric acetate etc.
Lower carbon number hydrocarbons described above is methane, ethane, propane, butane or ethene, propylene, butylene one or more mixtures wherein.
The application of catalyst of the present invention is as follows:
Catalyst of the present invention can be used in fixed-bed tube reactor, and reaction procatalyst is in advance at H
2350-500 DEG C of reduction 3-6h, H in atmosphere
2air speed be 2500-6000 h
-1, heating rate is 0.5-2 DEG C/min, and the pressure of reduction is 0.1-2MPa.
Concrete reaction condition is: reaction temperature 130-350 DEG C, and reaction pressure is 1.5-3.5MPa, and the liquid air speed of acetone is 0.5-5 h
-1, acetone and H
2mol ratio be 1-20:100.
Under reaction condition of the present invention, the conversion ratio of acetone is greater than 90%, and the selective of isopropyl alcohol is greater than 90%.
The present invention compared with prior art has the following advantages:
The preparation method of catalyst is simple, and cost lower and the filling be easy in practical operation and use, reaction condition is gentle, and conversion per pass is high, and catalyst stability is better.
Detailed description of the invention
Embodiment 1
Take 15.8g diatomite and be placed in Muffle furnace, 600 DEG C of roasting 6h, heating rate is 1 DEG C/min, obtains pretreated carrier.
Take 2.59g ammonium tungstate water-soluble, be configured to the solution of 0.1mol/L, then add the carrier after Vehicle element, in 80 DEG C of slow evaporates to dryness of water-bath after dipping 10h, sample be placed in the baking oven dried overnight of 100 DEG C, then above-mentioned carrier is placed in ethene atmosphere, the air speed of ethene is 6000h
-1, pressure is 0.1MPa, is down to room temperature in 2.5%O after being warming up to 600 DEG C of carbonization 6h with 1 DEG C/min
2passivation 8h in/Ar gaseous mixture, is down to after room temperature in 2%O
2the carrier of carried metal carbide is obtained after passivation 8h in/Ar gaseous mixture, taking 15.59g nitric hydrate nickel adds in deionized water, be mixed with the aqueous solution of 2mol/l, in the catalyst carrier obtained before then joining, after 100 DEG C of dry 10h by gained sample in He in 500 DEG C of roasting 5h, heating rate is 2 DEG C/min, and sample is obtained catalyst after being cooled to room temperature.The catalyst NiO mass fraction obtained is the mass fraction of 20%, WC is 1%, and diatomite support mass fraction is 79%.
Filling in fixed-bed tube reactor by above-mentioned obtained catalyst 2ml, is 6000 h in air speed
-1, pressure is the H of 0.2 MPa
2in atmosphere, be warming up to 400 DEG C with 1 DEG C/min, reduction 6h, then cools the temperature to reaction temperature.The reaction condition of acetone hydrogenation petrohol is: reaction temperature is 160 DEG C, and reaction pressure is 2.5 MPa, and liquid air speed is 0.5 h
-1, H
2: acetone=50 (mol ratio), under the reaction conditions, the conversion ratio of acetone is 96%, and the selective of isopropyl alcohol is 91%, and accessory substance is methyl iso-butyl ketone (MIBK) and DAA.
Embodiment 2
Take 16.6g carrier S BA-15 and be placed in Muffle furnace, 500 DEG C of processed 7h, heating rate is 2 DEG C/min, obtains pretreated carrier.
Take 0.736g ammonium molybdate to be dissolved in the aqueous solution that deionized water is configured to 0.15mol/l and to add pretreated carrier, leave standstill 6h, be placed on dry 18h in 120 DEG C of baking ovens in 80 DEG C of drying with water baths.The sample obtained is at CO:H
2in 700 DEG C of carbonization 8h, CO+H in the carburizing atmosphere of=1:1
2the air speed of gaseous mixture is 6000h
-1, pressure is 0.2MPa, is down to after room temperature passes into 1%O until temperature
2/ Ar gaseous mixture passivation 8h, obtains the carrier after load carbide.Take 11.7g nickel nitrate and be dissolved in deionized water, the aqueous solution being configured to certain volume is then added drop-wise on above-mentioned carrier, and dry 24h in 120 DEG C, the sample after oven dry is warming up to 500 DEG C of roasting 5h with 1 DEG C/min in an ar atmosphere, and heating rate is 2 DEG C/min.The flow velocity of Ar is 800ml/min, and pressure is 0.1MPa.The catalyst weight obtained consists of: molybdenum carbide percentage composition is the percentage composition of 2%, NiO is 15%, SiO
2percentage composition be 83%.
Filling in fixed-bed tube reactor by above-mentioned obtained catalyst 2ml, is 8000 h in air speed
-1, pressure is the H of 0.2 MPa
2in atmosphere, be warming up to 500 DEG C with 1 DEG C/min, reduction 4h, is then down to reaction temperature.The reaction condition of acetone hydrogenation petrohol is: reaction temperature is 275 DEG C, and reaction pressure is 3MPa, and liquid air speed is 0.5 h
-1, acetone: H
2=1:100 (mol ratio), under the reaction conditions, the conversion ratio of acetone is 98%, and the selective of isopropyl alcohol is 93%.
Embodiment 3
Take 16.6g alundum (Al2O3) and be placed in Muffle furnace, 500 DEG C of dehydration 7h, heating rate is 2.5 DEG C/min, obtains pretreated carrier.
Take 0.184g ammonium molybdate to be dissolved in the aqueous solution that deionized water is configured to 0.3mol/L and to add pretreated carrier, leave standstill in 80 DEG C of drying with water baths after 12h, the sample after oven dry is placed in 120 DEG C of dry 20h of baking oven.The sample obtained is in 700 DEG C of carbonization 9h in ethene atmosphere, and ethene air speed is 6000h
-1, pressure is 0.5MPa, is down to after room temperature passes into 1%O until temperature
2/ Ar gaseous mixture passivation 8h, obtains the carrier after load carbide.Take 11.55g nickel nitrate and be dissolved in deionized water, the aqueous solution being configured to certain volume then impregnated on above-mentioned carrier, and then 120 DEG C of oven dry are spent the night, and the sample after oven dry is warming up to 500 DEG C of roasting 5h with 1 DEG C/min in an ar atmosphere, and heating rate is 1 DEG C/min.The catalyst weight obtained consists of: molybdenum carbide percentage composition is the percentage composition of 0.5%, NiO is 15%, and the percentage composition of alundum (Al2O3) is 84.5%.
Filling in fixed-bed tube reactor by above-mentioned obtained catalyst 2ml, is 5000 h in air speed
-1, pressure is the H of 2 MPa
2in atmosphere, be warming up to 500 DEG C with 1 DEG C/min, reduction 4h, is then down to reaction temperature.The reaction condition of acetone hydrogenation petrohol is: reaction temperature is 200 DEG C, and reaction pressure is 3MPa, and liquid air speed is 1.5 h
-1, acetone: H
2=1:50 (mol ratio), under the reaction conditions, the conversion ratio of acetone is 95%, and the selective of isopropyl alcohol is 92%.
Embodiment 4
Take 16.6g alundum (Al2O3) and be placed in Muffle furnace, 600 DEG C of dehydration 5h, heating rate is 3 DEG C/min, obtains pretreated carrier.
Take 0.736g acid ammonium to be dissolved in the aqueous solution that deionized water is configured to 0.25mol/l and to add pretreated carrier, leave standstill in 90 DEG C of stirring in water bath evaporates to dryness after 11h, gained sample is dry 16h in 100 DEG C of baking ovens.Then by obtained sample at methane: in 700 DEG C of carbonization 9h in the atmosphere of propylene=1:1, mist air speed is 6000h
-1, gas pressure is 0.5MPa, is down to after room temperature passes into 2.5%O until temperature
2/ Ar gaseous mixture passivation 7h, obtains the carrier after load carbide.Take 11.7g nickel nitrate and be dissolved in deionized water, be configured to the aqueous impregnation of certain volume on above-mentioned carrier, then dry 16h in 120 DEG C, the sample after oven dry is warming up to 500 DEG C of roasting 5h with 1 DEG C/min in an ar atmosphere, and heating rate is 1.5 DEG C/min.The catalyst weight obtained consists of: molybdenum carbide percentage composition is the percentage composition of 2%, NiO is 15%, and the percentage composition of alundum (Al2O3) is 83%.
Filling in fixed-bed tube reactor by above-mentioned obtained catalyst 2ml, is 5000 h in air speed
-1, pressure is the H of 3MPa
2in atmosphere, be warming up to 500 DEG C with 1 DEG C/min, reduction 4h, then cools the temperature to reaction temperature.The reaction condition of acetone hydrogenation petrohol is: reaction temperature is 300 DEG C, and reaction pressure is 3MPa, and liquid air speed is 1.5 h
-1, acetone: H
2=13:100, under the reaction conditions, the conversion ratio of acetone is 95%, and the selective of isopropyl alcohol is 92%.
Embodiment 5
Take 13.6g zirconium dioxide and be placed in Muffle furnace, 550 DEG C of roasting 7h, heating rate is 3 DEG C/min, obtains pretreated carrier.
Take after 0.552 ammonium molybdate and 1.29g ammonium tungstate be dissolved in the aqueous solution of deionized water configuration 0.2mo/l respectively, join in pretreated carrier and leave standstill 10h, be then placed on dry 15h in 100 DEG C of baking ovens in 90 DEG C of water bath methods.The sample obtained is in 800 DEG C of carbonization 9h in propylene atmosphere, and propylene air speed is 6000h
-1, pressure is 0.3MPa, is down to after room temperature passes into 2%O until temperature
2/ Ar gaseous mixture passivation 8h, obtains the carrier after load carbide.Take 23.40g nickel nitrate and be dissolved in deionized water, the aqueous solution being configured to certain volume then impregnated on above-mentioned carrier, and then 100 DEG C of oven dry are spent the night, and the sample after oven dry is warming up to 500 DEG C of roasting 5h with 1 DEG C/min in an ar atmosphere.The catalyst weight obtained consists of: molybdenum carbide percentage composition is 1.5%, and the percentage composition of tungsten carbide is the percentage composition of 0.5%, NiO is 30%, and the percentage composition of zirconium dioxide is 68%.
Filling in fixed-bed tube reactor by above-mentioned obtained catalyst 2ml, is 4000 h in air speed
-1, pressure is the H of 3..5MPa
2in atmosphere, be warming up to 500 DEG C with 1 DEG C/min, reduction 6h, then cools the temperature to reaction temperature.The reaction condition of acetone hydrogenation petrohol is: reaction temperature is 275 DEG C, and reaction pressure is 2.5MPa, and liquid air speed is 1.0 h
-1, acetone: H
2=1:100 (mol ratio), under the reaction conditions, the conversion ratio of acetone is 95%, and the selective of isopropyl alcohol is 95%.
Embodiment 6
Take 15.6g carrier ZSM-5 and be placed in Muffle furnace, 500 DEG C of roasting 5.5h, heating rate is 1 DEG C/min, obtains pretreated carrier.
Take the aqueous solution that 5.18g ammonium tungstate is configured to 0.5mol/l, then add pretreated carrier, after leaving standstill 6h, be placed on dry 24h in 110 DEG C of baking ovens in 90 DEG C of water bath methods.The sample obtained is in 700 DEG C of carbonization 9h in ethane atmosphere, and ethane air speed is 6500h
-1, pressure is 0.2MPa, is down to after room temperature passes into 1%O until temperature
2/ Ar gaseous mixture passivation 8h, obtains the carrier after load carbide.Take 15.59g nickel nitrate and be dissolved in deionized water, the aqueous solution being configured to certain volume then impregnated on above-mentioned carrier, and then dry 18h for 120 DEG C, the sample after oven dry is warming up to 500 DEG C of roasting 5h with 1 DEG C/min in He atmosphere, and pressure is 0.2MPa.The catalyst obtained consists of: the percentage composition of the percentage composition of tungsten carbide to be the percentage composition of 2%, NiO be 20%, ZSM-5 is 88%.
Filling in fixed-bed tube reactor by above-mentioned obtained catalyst 2ml, is 5500 h in air speed
-1, pressure is the H of 3MPa
2in atmosphere, be warming up to 500 DEG C with 1 DEG C/min, reduction 5h, then cools the temperature to reaction temperature.The reaction condition of acetone hydrogenation petrohol is: reaction temperature is 300 DEG C, and reaction pressure is 3.0MPa, and liquid air speed is 1.2 h
-1, acetone: H
2=1:50 (mol ratio), under the reaction conditions, the conversion ratio of acetone is 90%, and the selective of isopropyl alcohol is 95%.
Embodiment 7
Take 15g SBA-15 and be placed in Muffle furnace, be warming up to 700 DEG C with 2.5 DEG C/min, after roasting 7.5h, obtain pretreated carrier.
Take the aqueous solution that 4.98g ammonium tungstate is configured to 0.3mol/L, then join in pretreated SBA-15, mixture to leave standstill after 5h evaporate to dryness in 90 DEG C of water-baths, and the sample after evaporate to dryness dries 10h in 120 DEG C of baking ovens.The sample obtained is in 700 DEG C of carbonization 9h in propane atmosphere, and propane air speed is 6000h
-1, pressure is 0.2MPa, is down to after room temperature passes into 1%O until temperature
2/ Ar gaseous mixture passivation 8h, obtains the carrier after load carbide.
Taking 4.85g nitric hydrate cobalt adds in deionized water, and in the catalyst carrier obtained before the aqueous solution being configured to 3mol/l then impregnated in, gained sample is in 500 DEG C of roasting 5h in He, and heating rate is 1 DEG C/min.The mass percent of the catalyst obtained is: Co
3o
4be the content of 20%, WC be 1%, SBA-15 content be 79%.
Filling in fixed-bed tube reactor by above-mentioned obtained catalyst 2ml, is 4500 h in air speed
-1, pressure is the H of 2MPa
2in atmosphere, be warming up to 400 DEG C with 1 DEG C/min, reduction 6h, then cools the temperature to reaction temperature.The reaction condition of acetone hydrogenation petrohol is: reaction temperature is 260 DEG C, and reaction pressure is 2.5 MPa, and liquid air speed is 0.5 h
-1, acetone: H
2:=1:50 (mol ratio), under the reaction conditions, the conversion ratio of acetone is 97%, and the selective of isopropyl alcohol is 97%, and accessory substance is methyl iso-butyl ketone (MIBK) and the DAA of trace.
Claims (10)
1., for a catalyst for acetone hydrogenation preparing isopropanol, it is characterized in that the weight ratio of catalyst consists of:
Activity component metal oxide content is 10-30%, and metal carbides content is 0.5%-2%, and vector contg is 68-89.5%.
2. a kind of catalyst for acetone hydrogenation preparing isopropanol as claimed in claim 1, is characterized in that described metal oxide is NiO, Co
3o
4or Fe
2o
3.
3. a kind of catalyst for acetone hydrogenation preparing isopropanol as claimed in claim 1, is characterized in that described metal carbides are the one or both mixture in tungsten carbide or molybdenum carbide.
4. a kind of catalyst for acetone hydrogenation preparing isopropanol as claimed in claim 1, is characterized in that described carrier is SiO
2, molecular sieve, SBA-15, alundum (Al2O3), zirconium dioxide or diatomite.
5. the preparation method of a kind of catalyst for acetone hydrogenation preparing isopropanol as described in any one of claim 1-4, is characterized in that comprising the steps:
(1) carrier is warming up to 500-800 DEG C of roasting 6-8 h with 1-3 DEG C/min, is then down to room temperature and obtains pretreated carrier;
(2) soluble metal carbide precursor salt is configured to the aqueous solution of 0.1-2mol/L, by catalyst composition by configuration after solution impregnation on pretreated carrier, dip time is 6-12, then evaporate to dryness in the water-bath of 70-100 DEG C, the sample that obtains is placed in 100-120 DEG C of dry 8-24h, obtains the carrier of carried metal carbide predecessor;
(3) will the carrier of carried metal carbide predecessor be obtained at lower carbon number hydrocarbons, or press CO and H
2volume ratio is that 1-5:10 forms carbonization in the carbonization medium of gaseous mixture, and be warming up to 600-800 DEG C with 0.5-2 DEG C/min, carbonization 3-9h, the air speed of carbonization gas is 3000-8000h
-1, the pressure of carbonization gas is 0.1-0.5MPa, after being down to room temperature, is 0.5-2.5%O in volume ratio
2in/Ar gaseous mixture after passivation 6-10, obtain the carrier of load carbide;
(4) by the active component precursor salt of solubility, the aqueous solution of 0.1-2mol/L is configured to by the composition of catalyst, to be configured to the aqueous solution is added drop-wise on the carrier that obtains in step (3), after 100-120 DEG C of dry 10-24h, under an inert atmosphere, be warming up to 400-600 DEG C of roasting 4-6 h with 0.5-2 DEG C/min, sample is catalyst after being cooled to room temperature.
6. the preparation method of a kind of catalyst for acetone hydrogenation preparing isopropanol as claimed in claim 5, is characterized in that the metal carbides precursor salt of described solubility is ammonium molybdate, ammonium metatungstate or sodium tungstate.
7. the preparation method of a kind of catalyst for acetone hydrogenation preparing isopropanol as claimed in claim 5, is characterized in that the active component predecessor of described solubility is nickel nitrate, citric acid nickel, cobalt nitrate, cobalt acetate, ferric nitrate or ferric acetate.
8. the preparation method of a kind of catalyst for acetone hydrogenation preparing isopropanol as claimed in claim 5, is characterized in that described lower carbon number hydrocarbons is one or more mixtures in methane, ethane, propane, butane or ethene, propylene, butylene.
9. the preparation method of a kind of catalyst for acetone hydrogenation preparing isopropanol as claimed in claim 5, is characterized in that described inert atmosphere is He, Ar or nitrogen.
10. the application of a kind of catalyst for acetone hydrogenation preparing isopropanol as described in any one of claim 1-4, is characterized in that comprising the steps:
Catalyst is used in fixed-bed tube reactor, and reaction procatalyst is in advance at H
2350-500 DEG C of reduction 3-6h, H in atmosphere
2air speed be 2500-6000 h
-1, heating rate is 0.5-2 DEG C/min, and the pressure of reduction is 0.1-2MPa;
Concrete reaction condition is: reaction temperature 130-350 DEG C, and reaction pressure is 1.5-3.5MPa, the liquid air speed of acetone
For 0.5-5 h
-1, acetone and H
2mol ratio be 1-20:100.
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| CN107011107A (en) * | 2017-05-16 | 2017-08-04 | 中国科学技术大学 | A kind of method that use load type metal catalyst prepares alcohol |
| CN107824208A (en) * | 2017-11-06 | 2018-03-23 | 太原理工大学 | A kind of preparation method containing nickel methenyl catalyst |
| CN107952473A (en) * | 2016-10-14 | 2018-04-24 | 中国石油化工股份有限公司 | Preparing isopropyl alcohol by acetone hydrogenation catalyst |
| CN107952468A (en) * | 2016-10-14 | 2018-04-24 | 中国石油化工股份有限公司 | Preparing isopropyl alcohol by acetone hydrogenation catalyst and method |
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| CN111215077A (en) * | 2020-02-19 | 2020-06-02 | 山东京博石油化工有限公司 | Catalyst for synthesizing isopropanol and preparation method and application thereof |
| CN111389436A (en) * | 2020-03-18 | 2020-07-10 | 中国科学院广州能源研究所 | Preparation method of efficient and stable molybdenum carbide catalyst for dimethyl ether steam reforming hydrogen production |
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