CN102850157A - Novel technique for preparing long-chain alkane efficiently through multifunctional catalyst in one-step method - Google Patents
Novel technique for preparing long-chain alkane efficiently through multifunctional catalyst in one-step method Download PDFInfo
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Abstract
The invention relates to a novel technique for preparing long-chain alkane efficiently through a multifunctional catalyst in a one-step method. The novel technique can be used for producing the long-chain alkane in one step with high selectively under a relative mild condition, and solve the problems of strict reaction condition, low energy efficiency and low alkane selectivity in a process of preparing the long-chain alkane by biomass derivatives. According to the technique, condensation products (C8, C9, C13 and C15) of a biomass derivative, namely furfural or HMF (Hydroxy Methyl Furfural), and acetone are taken as the raw materials, and by designing the three-center multifunctional catalyst of metal (I)-metal (II)-acid, the original two steps of independent reactions which require strict reaction conditions and need different catalysts to join in are combined into an one-step reaction which requires tender reaction conditions, so that the selectivity on corresponding alkane (octane, nonane, tridecane and pentadecane) is improved greatly, the highest yield can be 97%, and meanwhile, a step of separating the product from the catalyst is omitted, therefore, the energy efficiency of the while process is improved by a great step.
Description
Technical field
The present invention belongs to chemical technology, catalytic chemistry, organic chemistry filed, particularly by the technology of polyfunctional catalyst single stage method from the biomass derivatives prepare liquid fuel.
Background technology
The whole world approximately has 95% take oil as raw material production in 800,000,000 tons the chemical every year at present.As everyone knows, this non-renewable fossil energy is about to exhausted within a predictable time, and the discharging of a large amount of greenhouse gases causes global warming and a series of economy, politics, the environmental problem brought thus become increasingly conspicuous, the reproducible new forms of energy of developing green become the task of top priority (Chemical Review, 2006,106:4044-4098).In recent years, biomass resource is because the characteristics such as its cheapness, recyclability, low contaminative (GHG (Greenhouse Gases) emissions mitigation) and Sustainable development have become the emphasis that domestic and international scientist studies.Satisfy the primary demand of contemporary society's production and transport fuel and fine chemicals, and don't affect descendants's growth requirement, the development biorefining solves the key point of this challenge beyond doubt.Enter 21 century, academia, business circles and government department are efficiently and economically utilizing biomass resource as major objective.
Lignocellulose is cheap and the abundantest biomass sources, comprise Mierocrystalline cellulose, hemicellulose and xylogen (Bioresource Technology, 2002,83:37-46).At present, ligno-cellulosic materials can change into liquid fuel from following three main approach: (1) gasification obtains synthetic gas and synthesizes hydrocarbon polymer (diesel oil or gasoline), methyl alcohol and other fuel (Energy Fuels of different chain length through the Fischer-Tropsch reaction again, 2005,19:591-596); (2) pyrolysis or liquefaction obtain bio oil, and the refining of then upgrading (Science, 1944,99:309-311, Energy Fuels, 1991,5:399-405); (3) catalytic hydrolysis obtains monose, obtains intermediate through sugar dehydration, again by corresponding intermediate can further obtain the transport fuels such as gasoline and diesel oil (Science, 2005,308:1446-1450).
The evaporating method device is simple, technical maturity, but in gasification, need to evaporate a large amount of water, this can consume high, and efficiency ratio is lower; And the advantage of pyrolysis or liquefaction process is that process apparatus is simple, cost is lower, but energy consumption is still very high, product does not almost have selectivity, comprise tar, alcohol, aldehyde, ester, coke and aromatic compound etc., and separation difficulty, also can produce a large amount of coke (Chinese patent CN101153219B).At present of greatest concern is the catalyzed conversion of biomass, comprising acid hydrolysis, dehydration, C-C coupled to increase the process (ChemSusChem such as carbochain (such as aldol condensation, ketonization reaction, oligomerization etc.), hydrogenation are saturated, dehydration/hydrogenation, 2008,1:417-424), can be cellulose conversion the transport fuels such as gasoline, diesel oil, kerosene, ester by catalyzed conversion.
At present, Mierocrystalline cellulose and hemicellulose can obtain corresponding monose (hexose and five-carbon sugar comprise glucose, fructose and wood sugar etc.) efficiently through acid (mineral acid, solid acid) hydrolysis.5 hydroxymethyl furfural (HMF) and furfural then are the Important Platform molecules that is formed after acid-catalyzed dehydration by hexose and five-carbon sugar respectively, can be derived by these plateform molecules catalyzed conversions to obtain a series of fuels and chemicals.2005, the Dumesic research group reported first of Univ Wisconsin-Madison USA prepare the Catalytic processes (Science of long chain alkane (gasoline and diesel oil) from HMF and furfural, 2005,308:1446-1450), comprise that aldol condensation, hydrogenation are saturated, three steps of dehydration/hydrogenation, the reaction second step carries out at batch still, with Pd/Al
2O
3Be catalyzer; The 3rd step is with Pt/SiO
2-Al
2O
3For catalyzer carries out in fixed bed.The reaction conditions in two steps is relatively harsher wherein, all needs high temperature or high pressure, and wherein reacting the second step temperature slightly low is 120 ℃, and the 3rd step then needed 250-265 ℃, and reaction pressure is respectively: 5.5MPa and 5.6-6MPa.Harsh reaction conditions must cause the reduction of energy efficiency, runs in the opposite direction with energy-saving and emission-reduction; And rear two the step all carry out at aqueous phase, for preventing serious carbon deposit (reactant that is equivalent to 20-50%) that too high temperature causes and the inactivation of catalyzer, design again four complicated phase reactors, introduced n-Hexadecane as extraction agent, increased investment and the separation costs of reaction unit; In addition, the long-chain product of " hard-earned " has quite a few by catalytic pyrolysis (C-C bond rupture) under exacting terms, has generated the not high small molecules short chain alkanes (CH of added value
4～C
5H
12), having reduced the selectivity of target product long chain alkane, energy efficiency also further reduces thereupon.
Prepare the last two steps in the long chain alkane technique (namely saturated through hydrogenation by condensation product, dehydration/hydrogenation to long chain alkane) severe reaction conditions for solving above-mentioned biomass derivatives, energy efficiency is hanged down and the problems such as the long chain alkane selectivity is low, and we have furtherd investigate the reaction mechanism of the last two steps.Open loop (fracture of C-O key) this step of finding the tetrahydrofuran (THF) ring is difficult to occur, in case and open loop occurs, then dehydration/hydrogenation will be much gentle, even at room temperature get final product shortening.For reducing the condition of furan nucleus or the open loop of tetrahydrofuran (THF) ring, we imagine a kind of metal with redox active of introducing, the product of aldol condensation is used for assisting the fracture of catalysis carbon-oxygen bond, so that can be converted into long chain alkane by single step reaction on a catalyzer.Based on this thinking, we have designed metal (I)-metal (II)-solid acid three center polyfunctional catalysts, metal (I) is mainly used in shortening (dissociating of hydrogen), the effect of dehydration (dehydroxylation) is mainly played in acid, and the purpose of introducing metal (II) is concerted catalysis C―O bond cleavage (the particularly open loop of furan nucleus and tetrahydrofuran (THF) ring), improve the transformation efficiency of reaction and to the selectivity of alkane, thereby can be at the corresponding long chain alkane that obtains of relatively gentle next step high yield of condition, greatly increased the energy efficiency of this process, cost of investment can reduce greatly simultaneously.
Summary of the invention
The object of the present invention is to provide a kind of new technology that is prepared long chain alkane by polyfunctional catalyst single stage method efficient catalytic biomass derivatives.May further comprise the steps: with the condensation product of biomass derivatives furfural (or HMF) with acetone, solvent and metal (I)-metal (II)-solid acid three center polyfunctional catalysts are fed into the stainless steel autoclave with polytetrafluoroethylliner liner, reactant concn 3-50%, reactant is 2-20 with the catalyst quality ratio: 1, at 0-60 ℃, 0.5-1.5MPa high-speed stirring reaction 10min-4h under the hydrogen pressure, then continue reaction 4-30h at 110-190 ℃ and obtain corresponding long chain alkane, the transformation efficiency of reaction is all greater than 99.9%, and the highest yield can reach 97%.The present invention also can directly carry out in fixed bed, and reaction effect and batch still are very nearly the same.
The described condensation product of above-mentioned steps can be single condensation product C of furfural and acetone
8(4-(2-furyl)-3-butene-2-ketone), two condensation product C
13(two (the 2-furyl)-Isosorbide-5-Nitrae-pentadienes of 1,5--3-ketone) or its mixture also can be single condensation product C of HMF and acetone
9(4-(5-methylol-2-furyl)-3-butene-2-ketone), two condensation product C
15(two (5-methylol-2-furyl)-Isosorbide-5-Nitrae-pentadiene-3-ketone of 1,5-) or its mixture; Solvent can be methyl alcohol, ethanol, butanols, ether, tetrahydrofuran (THF), ethyl acetate, alkane, methylene dichloride, the mixture of ethylene dichloride or its arbitrary proportion.Catalyzer is that metal (I) is carried on the compound of metal (II) by equi-volume impregnating or coprecipitation method.Metal (I) can be the precious metals pt with hydrogenation activity, Pd, Ru, Rh, Ir or non-noble metal Ni, Co, among the Cu one or several, metal (II) can be the front transition element Ti with redox active (being the catalyzed carbon oxygen bond rupture), V, Cr, Mn, Co, Zr, Nb, Mo, Ta, W, among the Re one or more, acid site can be that the compound that contains metal (II) (comprises oxide compound, oxyhydroxide, halogenide, vitriol, phosphoric acid salt, metal acid, metal acid-salt, the metal heteropolyacid, metal heteropolyacid salt etc.) the L acid site or the B acid site that produce.The maximum characteristics of this Catalytic processes are exactly by design metal (I)-metal (II)-solid acid three center polyfunctional catalysts, make the independent reaction that two steps of severe reaction conditions originally need different catalysts to participate in, be merged into the single step reaction of reaction conditions gentleness, reduced the separating step of product and catalyzer; And adopt organic solvent to avoid the generation of carbon deposit, the life-span of having improved catalyzer; In addition, gentle reaction conditions has improved the selectivity of long chain alkane greatly, the transformation efficiency of reaction is all greater than 99.9%, yield reaches as high as 97%, thereby make the whole energy efficiency for preparing long chain alkane from biomass derivatives catalysis promote a very large step, really realize low power consuming, high production, under relatively gentle condition, carried out energy conversion.
Description of drawings
Accompanying drawing is the reaction schematic diagram that is efficiently prepared long chain alkane by the polyfunctional catalyst single stage method.R
1For-H or-CH
2OH, R
2For-H or-CH
3
Specific embodiments
The batch still reaction:
With furfural or HMF and condensation of acetone product C 8, C9, C13, one or more mixture 0.2-6g and solvent (methyl alcohol among the C15, ethanol, ether, tetrahydrofuran (THF), ethyl acetate, alkane, methylene dichloride, one or more mixing in the ethylene dichloride) 6g drops into the intermittent high-pressure reactor with the 50ml polytetrafluoroethylliner liner, namely controlling the substrate mass concentration is 3-50%, add again described polyfunctional catalyst 0.02-1.0g, the mass ratio of control substrate and catalyzer is 2-20, at 0-60 ℃, 0.5-1.5MPa under the hydrogen pressure, high-speed stirring, reaction 10min-4h, then be warming up to 110-190 ℃ and continue reaction 4-30h, obtain corresponding long chain alkane (octane, nonane, tridecane and pentadecane).
Fixed bed reaction:
At first with three center polyfunctional catalyst compressing tablets and be ground into 40-60 order particle, the internal diameter of then the 0.4-2g catalyzer being packed into is 6 millimeters, long 55 millimeters stainless steel tubular type reactor, and rest part fills to reduce dead volume with 40-60 order quartz sand.Reaction tubes is put into the fixing and whole device of hunting leak of Reaktionsofen boost to 0.5-3.0MPa (hydrogen partial pressure is 0.2-1.0MPa) with the hydrogen nitrogen mixed gas of 5-100% afterwards, carry out under liquid state to guarantee whole reaction.The control temperature of reaction is 110-190 ℃, and gas flow rate is 2-100ml/min, and C8, C9, C13, C15 strength of solution are 3%-50%, and solution injects with liquid phase pump, and air speed is 0.5-10h
-1, reaction solution by condensation, flows into reservoir through bed after the gas-liquid separation, take out at set intervals liquid and analysis in the groove.Below in conjunction with the furthermore bright technical scheme of the present invention of embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1
0.4g C8 (4-(2-furyl)-3-butene-2-ketone) and 6g solvents tetrahydrofurane are dropped into intermittent high-pressure reactor with the 50ml polytetrafluoroethylliner liner, add again 0.1g Pd/Nb
2O
5Polyfunctional catalyst, at 15 ℃, under the 1.0MPa hydrogen pressure, high-speed stirring, then reaction 10min is warming up to 170 ℃ and continues reaction 16h, C
8Transformation efficiency is 100%, and the octane yield is 97%.
Embodiment 2
With 1.0g C
9(4-(5-methylol-2-furyl)-3-butene-2-ketone) and 6g solvent methanol drop into the intermittent high-pressure reactor with the 50ml polytetrafluoroethylliner liner, add 0.4g Ru/WO again
3Catalyzer, at 40 ℃, under the 1.5MPa hydrogen pressure, high-speed stirring, then reaction 3h is warming up to 150 ℃ and continues reaction 24h, C
9Transformation efficiency is 100%, and the nonane yield is 51%, and all the other mainly are some also intermediate products of surplus oxygen existence.
Embodiment 3
With 0.5g C
13(two (the 2-furyl)-Isosorbide-5-Nitrae-pentadienes of 1,5--3-ketone) and 6g methylene chloride drop into the intermittent high-pressure reactor with the 50ml polytetrafluoroethylliner liner, add polyfunctional catalyst Pt/ZrOSO again
40.2g, at 25 ℃, under the 0.8MPa hydrogen pressure, high-speed stirring, then reaction 1h is warming up to 190 ℃ and continues reaction 4h, C
13Transformation efficiency is 100%, and the tridecane yield is 82%, has on a small quantity to produce other alkane because of carbon carbon scission of link.
Embodiment 4
With 0.8g C
15(two (5-methylol-2-furyl)-Isosorbide-5-Nitrae-pentadiene-3-ketone of 1,5-) and 6g solvent hexanaphthene drop into the intermittent high-pressure reactor with the 50ml polytetrafluoroethylliner liner, add 0.1g Pt/H again
3PW
12O
40, at 50 ℃, under the 1.5MPa hydrogen pressure, high-speed stirring, then reaction 4h is warming up to 160 ℃ and continues reaction 20h, C
15Transformation efficiency is 100%, and the pentadecane yield is 90%.
Embodiment 5
With 10g C
8Be dissolved in the 190g ethyl acetate and be made into 5% solution, at RuNi/VOPO
4Under the polyfunctional catalyst effect, react in fixed-bed reactor, the hydrogen nitrogen mixed gas with 20% is as reaction gas, and at 2.5MPa, 180 ℃, air speed is 3.6h
-1, gas flow rate is under the 20ml/min condition, C
8Can 100% transform the selectivity 92% of octane.
Embodiment 6
With 16g C
15Be dissolved in 184g ethanol and be made into 8% solution, at Pd/NbOPO
4Under the polyfunctional catalyst effect, react in fixed-bed reactor, the hydrogen nitrogen mixed gas with 10% is as reaction gas, and at 2.0MPa, 170 ℃, air speed is 1.2h
-1, gas flow rate is under the 40ml/min condition, C
15Can 100% transform the selectivity 65% of pentadecane.
Claims (3)
1. new technology that is efficiently prepared long chain alkane by the polyfunctional catalyst single stage method, it is characterized in that may further comprise the steps: with the condensation product of biomass derivatives furfural (or HMF) with acetone, solvent and metal (I)-metal (II)-solid acid three center polyfunctional catalysts are fed into the stainless steel autoclave with polytetrafluoroethylliner liner, reactant concn is 3-50%, reactant is 2-20 with the catalyst quality ratio: 1, at 0-60 ℃, 0.5-1.5MPa then high-speed stirring reaction 10min-4h under the hydrogen pressure continues reaction 4-30h at 110-190 ℃ and obtains corresponding long chain alkane.
2. the present technique invention also can directly be carried out in fixed bed, it is characterized in that: at 110-190 ℃, 0.5-3.0MPa under the condition, be that the raw material of 3-50% is by being equipped with the bed of metal (I)-metal (II)-sour three center polyfunctional catalysts with concentration, reaction gas can be pure hydrogen, also can be hydrogen nitrogen mixed gas, reaction gas density of hydrogen 5-100%, reaction gas flow velocity 2-100ml/min, air speed 0.5-10h
-1
3. claim 1 and the 2 described technology that prepared long chain alkane by polyfunctional catalyst single stage method efficient catalytic is characterized in that described solvent is methyl alcohol, ethanol, butanols, ether, tetrahydrofuran (THF), ethyl acetate, alkane, methylene dichloride, the mixture of ethylene dichloride or its arbitrary proportion.Catalyzer is that metal (I) is carried on the compound of metal (II) by equi-volume impregnating or coprecipitation method, metal in the catalyzer (I) can be the precious metals pt with hydrogenation activity, Pd, Ru, Rh, Ir or non-noble metal Ni, Co, among the Cu one or several, metal (II) can be the front transition element Ti with redox active, V, Cr, Mn, Co, Zr, Nb, Mo, Ta, W, among the Re one or more, the acid site can be that the compound that contains metal (II) (comprises oxide compound, oxyhydroxide, halogenide, vitriol, phosphoric acid salt, metal acid, metal acid-salt, metal heteropolyacid, metal heteropolyacid salt etc.) the L acid site or the B acid site that produce.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103977796A (en) * | 2014-05-18 | 2014-08-13 | 华东理工大学 | Catalyst used in preparation of long-chain alkane through catalytic hydrodeoxygenation of biomass |
| WO2016031988A1 (en) * | 2014-08-29 | 2016-03-03 | 積水化学工業株式会社 | Furan resin, method for producing same, thermosetting furan resin composition, cured product, and furan resin composite |
| CN105567283A (en) * | 2016-03-04 | 2016-05-11 | 浙江大学 | Method for preparing long-chain alkane through hydrolysis and in-situ hydrogenation and decarboxylation of micro-algal oil |
| CN108409560A (en) * | 2018-04-11 | 2018-08-17 | 合肥利夫生物科技有限公司 | A kind of preparation method of 1,13- tridecane diols ester and its 1,13- tridecane diols |
| WO2019218418A1 (en) * | 2018-05-17 | 2019-11-21 | 北京化工大学 | Preparation method for synthesizing photosensitive compound through claisen-schmidt reaction |
| CN111470927A (en) * | 2020-04-15 | 2020-07-31 | 华东师范大学 | Method for preparing high-melting-point wax from furfural |
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| CN115007168A (en) * | 2022-06-21 | 2022-09-06 | 常州工学院 | Preparation method of catalyst for converting short-chain fatty acid into hydrocarbon cleaning agent |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060076127A1 (en) * | 2001-07-11 | 2006-04-13 | Bowe Michael J | Catalytic Reactor |
| WO2008109877A1 (en) * | 2007-03-08 | 2008-09-12 | Virent Energy Systems, Inc. | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| CN101418225A (en) * | 2007-10-23 | 2009-04-29 | 北京化工大学 | Method for preparing biodiesel by using supported solid acid combining cosolvent |
| CN102068986A (en) * | 2011-01-06 | 2011-05-25 | 华东理工大学 | Catalyst used in ring-opening hydrogenation reaction of furan derivative |
| CN102295511A (en) * | 2011-07-01 | 2011-12-28 | 华东理工大学 | Novel catalysis technology for preparing long chain alkane from biomass derivative furfural or HMF |
| WO2012064701A1 (en) * | 2010-11-08 | 2012-05-18 | Wisconsin Alumni Research Foundation | A method for producing liquid hydrocarbon fuels directly from lignocellulosic biomass |
| US20120151826A1 (en) * | 2010-12-20 | 2012-06-21 | Shell Oil Company | Process to produce biofuels from biomass |
-
2012
- 2012-07-30 CN CN201210265948.0A patent/CN102850157B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060076127A1 (en) * | 2001-07-11 | 2006-04-13 | Bowe Michael J | Catalytic Reactor |
| WO2008109877A1 (en) * | 2007-03-08 | 2008-09-12 | Virent Energy Systems, Inc. | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| AU2008222628A1 (en) * | 2007-03-08 | 2008-09-12 | Virent, Inc. | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| CN101418225A (en) * | 2007-10-23 | 2009-04-29 | 北京化工大学 | Method for preparing biodiesel by using supported solid acid combining cosolvent |
| WO2012064701A1 (en) * | 2010-11-08 | 2012-05-18 | Wisconsin Alumni Research Foundation | A method for producing liquid hydrocarbon fuels directly from lignocellulosic biomass |
| US20120151826A1 (en) * | 2010-12-20 | 2012-06-21 | Shell Oil Company | Process to produce biofuels from biomass |
| CN102068986A (en) * | 2011-01-06 | 2011-05-25 | 华东理工大学 | Catalyst used in ring-opening hydrogenation reaction of furan derivative |
| CN102295511A (en) * | 2011-07-01 | 2011-12-28 | 华东理工大学 | Novel catalysis technology for preparing long chain alkane from biomass derivative furfural or HMF |
Cited By (14)
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|---|---|---|---|---|
| CN103977796A (en) * | 2014-05-18 | 2014-08-13 | 华东理工大学 | Catalyst used in preparation of long-chain alkane through catalytic hydrodeoxygenation of biomass |
| WO2016031988A1 (en) * | 2014-08-29 | 2016-03-03 | 積水化学工業株式会社 | Furan resin, method for producing same, thermosetting furan resin composition, cured product, and furan resin composite |
| US10221275B2 (en) | 2014-08-29 | 2019-03-05 | Sekisui Chemical Co., Ltd. | Furan resin, method for producing same, thermosetting furan resin composition, cured product, and furan resin composite |
| CN105567283A (en) * | 2016-03-04 | 2016-05-11 | 浙江大学 | Method for preparing long-chain alkane through hydrolysis and in-situ hydrogenation and decarboxylation of micro-algal oil |
| CN105567283B (en) * | 2016-03-04 | 2018-03-16 | 浙江大学 | A kind of microalgae oil is through hydrolyzing the method for preparing long chain alkane with hydrogenation decarboxylation in situ |
| CN108409560A (en) * | 2018-04-11 | 2018-08-17 | 合肥利夫生物科技有限公司 | A kind of preparation method of 1,13- tridecane diols ester and its 1,13- tridecane diols |
| WO2019218418A1 (en) * | 2018-05-17 | 2019-11-21 | 北京化工大学 | Preparation method for synthesizing photosensitive compound through claisen-schmidt reaction |
| CN111470927A (en) * | 2020-04-15 | 2020-07-31 | 华东师范大学 | Method for preparing high-melting-point wax from furfural |
| CN111470927B (en) * | 2020-04-15 | 2022-12-30 | 华东师范大学 | Method for preparing high-melting-point wax from furfural |
| CN113617343A (en) * | 2021-08-31 | 2021-11-09 | 福州大学 | Biomass oil deoxidation catalyst and preparation method and application thereof |
| CN114682263A (en) * | 2022-04-21 | 2022-07-01 | 中国科学院广州能源研究所 | Preparation method of sustainable aviation fuel oil hydrogenation catalyst |
| CN114682263B (en) * | 2022-04-21 | 2023-03-07 | 中国科学院广州能源研究所 | Preparation method of sustainable aviation fuel oil hydrogenation catalyst |
| CN115007168A (en) * | 2022-06-21 | 2022-09-06 | 常州工学院 | Preparation method of catalyst for converting short-chain fatty acid into hydrocarbon cleaning agent |
| CN115007168B (en) * | 2022-06-21 | 2024-03-01 | 常州工学院 | Preparation method of catalyst for converting short-chain fatty acid into hydrocarbon cleaning agent |
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