CN107011107A - A kind of method that use load type metal catalyst prepares alcohol - Google Patents

A kind of method that use load type metal catalyst prepares alcohol Download PDF

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Publication number
CN107011107A
CN107011107A CN201710343574.2A CN201710343574A CN107011107A CN 107011107 A CN107011107 A CN 107011107A CN 201710343574 A CN201710343574 A CN 201710343574A CN 107011107 A CN107011107 A CN 107011107A
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metal
catalyst
zirconium oxide
oxide
modified
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张颖
马严富
王昊
许光月
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University of Science and Technology of China USTC
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University of Science and Technology of China USTC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
    • 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
    • C07C29/14—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 a —CHO group
    • C07C29/141—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 a —CHO group with hydrogen or hydrogen-containing gases
    • 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
    • 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
    • C07C29/147—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 carboxylic acids or derivatives thereof
    • C07C29/149—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 carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C07D307/44—Furfuryl alcohol

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The invention provides a kind of method that use load type metal catalyst prepares alcohol, comprise the following steps：Carbonyl containing compound is under the catalytic action of load type metal catalyst, with H2Reduction reaction is carried out, alcohol compound is obtained；The load type metal catalyst includes：Catalyst carrier, and the metal being carried in catalyst carrier；The metal is the one or more in the 8th race's metal；The catalyst carrier is zirconium oxide, lanthanide metal oxide, the zirconium oxide that lanthanide metal oxide is modified, the zirconium oxide that period 4 transition metal oxide is modified, the zirconium oxide that period 5 transition metal oxide is modified, zirconium oxide or alumina modified zirconium oxide that alkaline earth oxide is modified.The present invention prepares alcohol using above-mentioned special catalyst, with high conversion rate, and selectivity is good, and reaction condition is gentle, the advantages of appliance arrangement is simple, with good prospects for commercial application.

Description

A kind of method that use load type metal catalyst prepares alcohol
Technical field
Alcohol is prepared the present invention relates to technical field of compound preparation, more particularly to a kind of use load type metal catalyst Method.
Background technology
It is common for corresponding alcohol to carbonyls such as aldehyde, ketone, ester and lactone Hydrogenation and again in commercial Application The technology wanted.Alcohol compound chemical property is stable, solvent, organic synthesis raw material is commonly used for, in organic synthesis and pharmacy Industry has a wide range of applications.Therefore it is organic chemistry filed research carbonyls to be optionally reduced into corresponding alcohol Emphasis.For example in furfural hydrogenation reduction prepares the reaction of furfuryl alcohol, raw material furfural is a kind of important source material of organic synthesis, furfuryl alcohol It is the important kind in furfural hydrogenation product.50% furfural is used to produce furfuryl alcohol in the world at present.Furfuryl alcohol mainly for the preparation of Furans resin, hot shooting core box, sand adhesive as the internal combustion engine foundary industry such as automobile, tractor, with improve casting quality and Promote the mechanization and automation of casting process, the solvent and rocket fuel of furans resin, varnish, pigment also acted as in addition, Intermediate acetyl propionic acid for synthesizing nutrient drug fruit furancarboxylic acid calcium etc..
The content of the invention
In view of this, the technical problem to be solved in the present invention is that provide one kind prepares alcohol using load type metal catalyst Method, with higher conversion ratio and yield.
The invention provides a kind of method that use load type metal catalyst prepares alcohol, comprise the following steps：
Carbonyl containing compound is under the catalytic action of load type metal catalyst, with H2Reduction reaction is carried out, alcohols is obtained Compound；
The load type metal catalyst includes：
Catalyst carrier, and the metal being carried in catalyst carrier；
The metal is the one or more in the 8th race's metal；
The catalyst carrier is zirconium oxide, lanthanide metal oxide, the zirconium oxide that lanthanide metal oxide is modified, the 4th The zirconium oxide of row transition metals oxide modifying, the zirconium oxide that period 5 transition metal oxide is modified, alkaline-earth metal oxygen Zirconium oxide or alumina modified zirconium oxide that compound is modified.
It is preferred that, the metal is one or more combinations in the race's metal of period 4 the 8th.
It is preferred that, the catalyst carrier is the zirconium oxide that lanthanide metal oxide is modified.
It is preferred that, the load type metal catalyst is prepared in accordance with the following methods：
A) salting liquid of the ion containing carrier metal is mixed with surfactant, pH value is adjusted using precipitating reagent, makes carrier Catalyst carrier is obtained after precipitation by metallic ion, aging, calcining；
B) catalyst carrier is scattered in organic solvent, mixed with the salting liquid of metal ion, after reaction, solid is done It is dry and calcine, obtain the load type metal catalyst.
It is preferred that, the carbonyl containing compound is aldehyde, ketone, ester or lactone.
It is preferred that, the carbonyl containing compound is containing other unsaturated groups in addition to carbonyl.
It is preferred that, the pressure of the hydrogen is 0.01~5MPa.
It is preferred that, the temperature of the reduction reaction is 0~200 DEG C, and the reaction time is within 24h.
It is preferred that, the reduction reaction is carried out in aqueous phase.
Compared with prior art, the invention provides a kind of method that use load type metal catalyst prepares alcohol, including Following steps：Carbonyl containing compound is under the catalytic action of load type metal catalyst, with H2Reduction reaction is carried out, alcohols is obtained Compound；The load type metal catalyst includes：Catalyst carrier, and the metal being carried in catalyst carrier；The gold Belong to for the one or more in the 8th race's metal；The catalyst carrier is zirconium oxide, lanthanide metal oxide, lanthanide series metal oxygen The zirconium oxide that compound is modified, the zirconium oxide that period 4 transition metal oxide is modified, period 5 transition metal oxide changes Property zirconium oxide, alkaline earth oxide be modified zirconium oxide or alumina modified zirconium oxide.The present invention is using above-mentioned specific Catalyst preparation alcohol, with high conversion rate, selectivity is good, and reaction condition is gentle, the advantages of appliance arrangement is simple, with good Prospects for commercial application.
Embodiment
The invention provides a kind of method that use load type metal catalyst prepares alcohol, comprise the following steps：
Carbonyl containing compound is under the catalytic action of load type metal catalyst, with H2Reduction reaction is carried out, alcohols is obtained Compound；
The load type metal catalyst includes：
Catalyst carrier, and the metal being carried in catalyst carrier；
The metal is the one or more in the 8th race's metal；One kind preferably in the race's metal of period 4 the 8th or One or more in a variety of combinations, i.e. iron, cobalt and nickel, are further preferably cobalt.
The catalyst carrier is zirconium oxide, lanthanide metal oxide, the zirconium oxide that lanthanide metal oxide is modified, the 4th The zirconium oxide of row transition metals oxide modifying, the zirconium oxide that period 5 transition metal oxide is modified, alkaline-earth metal oxygen Zirconium oxide or alumina modified zirconium oxide that compound is modified.The zirconium oxide that preferably lanthanide metal oxide is modified, further preferably The zirconium oxide being modified for lanthanum sesquioxide.
In some specific embodiments of this law, the catalyst is Co/La2O3, Co/ZrO2, Co/ZrO2·La2O3, Co/ZrO2·CeO2, Co/ZrO2·Pr6O11, Co/ZrO2·Nd2O3, Co/ZrO2·Yb2O3, Co/ZrO2·V2O5, Co/ ZrO2·ZnO2, Co/ZrO2·Nb2O5, Co/ZrO2·MoO3, Co/ZrO2MgO, Co/ZrO2·Al2O3, Fe/ZrO2· La2O3, Ni/ZrO2·La2O3, Ru/ZrO2·La2O3, Rh/ZrO2·La2O3, Pd/ZrO2·La2O3, Os/ZrO2·La2O3, Ir/ZrO2·La2O3Or Pt/ZrO2·La2O3。
Currently preferred, the load type metal catalyst is prepared in accordance with the following methods：
A) salting liquid of the ion containing carrier metal is mixed with surfactant, pH value is adjusted using precipitating reagent, makes carrier Catalyst carrier is obtained after precipitation by metallic ion, aging, calcining；
B) catalyst carrier is scattered in organic solvent, mixed with the salting liquid of metal ion, after reaction, solid is done It is dry and calcine, obtain the load type metal catalyst.
Wherein, the present invention is to the salt of the ion containing carrier metal and is not particularly limited, well known to those skilled in the art Water soluble salt.
The surfactant is preferably cetyl ammonium bromide.
The precipitating reagent is preferably sodium hydroxide solution.
The step A) calcining temperature be preferably 550 DEG C.
The salt of the metal ion is preferably nitrate.
The step B) in organic solvent be preferably acetone.
The step B) calcining is preferably specially：First in 200 DEG C~450 DEG C calcinings, again in the temperature higher than 450 DEG C after cooling Degree is lower to be calcined.
In some embodiments of the invention, the preparation method is specially：
Surfactant is dissolved in distilled water, the salting liquid of the ion containing supported metal is added, then precipitating reagent tune is added dropwise The pH of section system makes carrier metal ion precipitation, and aging, solid is filtered and washed, and dries, calcining, you can obtain catalyst load Body.The catalyst carrier is scattered in organic solvent, then metal salt compound is dissolved in the organic solvent, it is added to In above-mentioned carrier solution, at least 4h is stirred under constant temperature.Dried overnight after solvent is removed, by dried solid 200 DEG C~450 DEG C calcining, calcined again at a temperature of higher than 450 DEG C after cooling, you can obtain the load type metal catalyst.
The above-mentioned catalyst that the present invention is provided, using preceding need in atmosphere of hydrogen reduce.
The present invention is using carbonyl containing compound as raw material, and the carbonyl containing compound can contain carbonyl for aldehyde, ketone, ester or lactone etc. Based compound, in above-mentioned reaction, carbonyl is reduced to hydroxyl, and then prepares corresponding alcohol.The carbonyl containing compound knot Other unsaturated groups, such as alkenyl, alkynyl can also be contained in structure.
In above-mentioned reaction system, the pressure of hydrogen is preferably 0.01~5MPa, more preferably 0.1~4MPa, is further preferably 1 ~3MPa, particularly preferably 2MPa.
The temperature of the reaction is preferably 0~200 DEG C, more preferably 10~160 DEG C, is further preferably 20~120 DEG C, especially Preferably 40~80 DEG C.
The time of the reaction is preferably within 24h, within more preferably 16h, further preferably for 10h within.
It is preferred that, the reaction is carried out in aqueous phase.
Above-mentioned reaction uses solid catalysis system, under cryogenic, can efficiently make the carbonyls in liquid phase Selective hydrogenation generates alcohol.With spies such as preparation process is simple, high activity, high selectivity, reaction condition are gentle, stability is good Point, after reaction terminates, reaction solution is i.e. separable by filtering with catalyst, and catalyst is reusable, and catalytic activity and choosing Selecting property is not all reduced.
Test result indicates that, the above-mentioned method for preparing alcohol compound that the present invention is provided, conversion ratio is up to 100%, alcohol The selectivity of class compound is up to 100%.
In order to further illustrate the present invention, the preparation method of the alcohol provided with reference to embodiment the present invention is carried out in detail Description.
Method therefor is conventional method unless otherwise specified in following embodiments, and agents useful for same is commercially obtained .
The different polymolecularity load type metal catalysts of embodiment 1 react 8h aqueous catalysis chaffs in 60 DEG C, 2MPa hydrogen Aldehyde Hydrogenation is for furfuryl alcohol
0.5mmol furfurals are added in 25mL reactor, the metal that 50mg is supported on different metal oxides carrier is urged Agent, adds 10mL deionized waters, is passed through 2MPa hydrogen, is heated to after 60 DEG C, under stirring condition, 8 hours of reaction, cooling, Deflate, with ethanol transfer and dilute reaction solution, separate catalyst and reaction solution after centrifugation, use gas chromatographic analysis.
GC conditions are as follows：GC1690 gas-chromatographies, fid detector, capillary chromatographic column (HP-5.30m × 0.250mm × 0.25 μm), temperature programming is taken, starting column temperature is 40 DEG C, and 250 DEG C of guarantors are risen to 10 DEG C/min heating rate Hold 3 minutes.Carrier gas is 99.99% high pure nitrogen, and flow velocity is 1mL/min.
Catalyst and gas chromatographic analysis result are as shown in table 1：
The catalyst of 1 embodiment of table 1 and reaction result collect
Catalyst Conversion ratio (%) Furaldehyde yield (%)
Co/La2O3 95 95
Co/ZrO2 90 89
Co/ZrO2·La2O3 100 100
Co/ZrO2·CeO2 100 100
Co/ZrO2·Pr6O11 100 100
Co/ZrO2·Nd2O3 100 100
Co/ZrO2·Yb2O3 100 100
Co/ZrO2·V2O5 100 100
Co/ZrO2·ZnO2 97 96
Co/ZrO2·Nb2O5 98 98
Co/ZrO2·MoO3 98 97
Co/ZrO2·MgO 100 95
Co/ZrO2·Al2O3 100 100
Fe/ZrO2·La2O3 95 93
Ni/ZrO2·La2O3 100 100
Ru/ZrO2·La2O3 100 100
Rh/ZrO2·La2O3 100 100
Pd/ZrO2·La2O3 100 100
Os/ZrO2·La2O3 100 100
Ir/ZrO2·La2O3 100 100
Pt/ZrO2·La2O3 100 100
Embodiment 2
The different reactants of 0.5mmol, 50mg Co/ZrO are added in 25mL reactor2·La2O3For catalyst, plus Enter 10mL deionized waters, be passed through 2MPa hydrogen, be heated to after 60 DEG C, under stirring condition, 8 hours of reaction, cooling, deflation, use Ethanol transfer and dilute reaction solution, separate catalyst and reaction solution, use gas chromatographic analysis after centrifugation.
GC conditions are as follows：GC1690 gas-chromatographies, fid detector, capillary chromatographic column (HP-5.30m × 0.250mm × 0.25 μm), temperature programming is taken, starting column temperature is 40 DEG C, and 250 DEG C of guarantors are risen to 10 DEG C/min heating rate Hold 3 minutes.Carrier gas is 99.99% high pure nitrogen, and flow velocity is 1mL/min.
Reaction raw materials and gas chromatographic analysis result are as shown in table 2：
The reaction raw materials of 2 embodiment of table 2 and reaction result collect
Embodiment 3
The different reactants of 0.5mmol, 50mg Co/ZrO are added in 25mL reactor2·La2O3For catalyst, plus Enter 10mL deionized waters, be heated under required temperature, stirring condition, react after some hours, cool down, deflate, shifted with ethanol And dilute reaction solution, separate catalyst and reaction solution after centrifugation, use gas chromatographic analysis.
GC conditions are as follows：GC1690 gas-chromatographies, fid detector, capillary chromatographic column (HP-5.30m × 0.250mm × 0.25 μm), temperature programming is taken, starting column temperature is 40 DEG C, and 250 DEG C of guarantors are risen to 10 DEG C/min heating rate Hold 3 minutes.Carrier gas is 99.99% high pure nitrogen, and flow velocity is 1mL/min.
Reaction condition and gas chromatographic analysis result are as shown in table 3：
The reaction condition of 3 embodiment of table 3 and reaction result collect
From above-described embodiment, the method for preparing alcohol compound that the present invention is provided, with higher conversion ratio and Yield.
The explanation of above example is only intended to the method and its core concept for helping to understand the present invention.It should be pointed out that pair , under the premise without departing from the principles of the invention, can also be to present invention progress for those skilled in the art Some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (9)

1. a kind of method that use load type metal catalyst prepares alcohol, it is characterised in that comprise the following steps：
Carbonyl containing compound is under the catalytic action of load type metal catalyst, with H2Reduction reaction is carried out, alcohols chemical combination is obtained Thing；
The load type metal catalyst includes：
Catalyst carrier, and the metal being carried in catalyst carrier；
The metal is the one or more in the 8th race's metal；
The catalyst carrier is zirconium oxide, lanthanide metal oxide, the zirconium oxide that lanthanide metal oxide is modified, period 4 The zirconium oxide that transition metal oxide is modified, the zirconium oxide that period 5 transition metal oxide is modified, alkaline earth oxide Modified zirconium oxide or alumina modified zirconium oxide.
2. preparation method according to claim 1, it is characterised in that the metal is in the race's metal of period 4 the 8th One or more combinations.
3. preparation method according to claim 1, it is characterised in that the catalyst carrier changes for lanthanide metal oxide The zirconium oxide of property.
4. preparation method according to claim 1, it is characterised in that the load type metal catalyst is in accordance with the following methods Prepare：
A) salting liquid of the ion containing carrier metal is mixed with surfactant, pH value is adjusted using precipitating reagent, makes carrier metal Catalyst carrier is obtained after ion precipitation, aging, calcining；
B) catalyst carrier is scattered in organic solvent, mixed with the salting liquid of metal ion, after reaction, solid drying, And calcine, obtain the load type metal catalyst.
5. preparation method according to claim 1, it is characterised in that the carbonyl containing compound is aldehyde, ketone, ester or interior Ester.
6. preparation method according to claim 1, it is characterised in that the carbonyl containing compound contains its in addition to carbonyl His unsaturated group.
7. preparation method according to claim 1, it is characterised in that the pressure of the hydrogen is 0.01~5MPa.
8. preparation method according to claim 1, it is characterised in that the temperature of the reduction reaction is 0~200 DEG C, instead It is within 24h between seasonable.
9. preparation method according to claim 1, it is characterised in that the reduction reaction is carried out in aqueous phase.
CN201710343574.2A 2017-05-16 2017-05-16 A kind of method that use load type metal catalyst prepares alcohol Pending CN107011107A (en)

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
CN111848553A (en) * 2020-07-29 2020-10-30 湘潭大学 Method for catalytically synthesizing gamma-valerolactone by cobalt-based hydrogenation catalyst
CN112237937A (en) * 2019-07-18 2021-01-19 中国石油化工股份有限公司 Nitrogen-doped zirconia carrier and preparation method and application thereof
CN113292520A (en) * 2021-06-03 2021-08-24 厦门大学 Synthetic method and application of magnetic catalyst for preparing furfuryl alcohol by catalytic hydrogenation of furfural
CN113941347A (en) * 2021-09-23 2022-01-18 中国科学技术大学 Application of high-efficiency and high-stability nano catalyst with film coating layer
CN113941346A (en) * 2021-09-23 2022-01-18 中国科学技术大学 Supported nano catalyst with film coating layer and preparation method thereof
CN114345358A (en) * 2021-12-14 2022-04-15 湘潭大学 Bifunctional catalyst for catalyzing condensation-hydrodeoxygenation of cyclopentanone to prepare high-density aviation fuel

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