CN102850157B - 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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- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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, is particularly prepared the technology of liquid fuel from biomass derivatives by polyfunctional catalyst single stage method.
Background technology
95% is had to be raw material production with oil in the chemical that the current whole world is approximately annual 800000000 tons.As everyone knows, this non-renewable fossil energy is about to exhausted within a predictable time, and the discharge of a large amount of greenhouse gases causes global warming and a series of economy brought thus, politics, environmental problem to 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, due to features such as its cheapness, recyclability, low stain (GHG (Greenhouse Gases) emissions mitigation) and Sustainable developments, has become the emphasis of domestic and international scientist research.Meet the primary demand of contemporary society's production and transport fuel and fine chemicals, and don't affect the growth requirement of descendants, 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 the most cheap and the abundantest biomass source, comprises 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 again through the hydrocarbon polymer (bavin Water Oil Or Gas) of Fischer-Tropsch Reactive Synthesis different chain length, methyl alcohol and other fuel (Energy Fuels, 2005,19:591-596); (2) pyrolysis or liquefaction obtain bio oil, refining of then upgrading (Science, 1944,99:309-311, Energy Fuels, 1991,5:399-405); (3) catalytic hydrolysis obtains monose, obtains intermediate, then can obtain the transport fuel such as gasoline and diesel oil (Science, 2005,308:1446-1450) further by corresponding intermediate through sugar dehydration.
Evaporating method device is simple, technical maturity, but needs to evaporate a large amount of water in gasification, and this can consume high, and efficiency comparison is low; 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).Of greatest concern is at present the catalyzed conversion of biomass, coupled to increase the process (ChemSusChem such as carbochain (as aldol condensation, ketonization reaction, oligomerization etc.), hydrotreated lube base oil, dehydration/hydrogenation comprising acid hydrolysis, dehydration, C-C, 2008,1:417-424), can be the transport fuels such as gasoline, diesel oil, kerosene, ester cellulose conversion 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 are then the Important Platform molecules formed after acid-catalyzed dehydration by hexose and five-carbon sugar respectively, can be derived obtain a series of fuels and chemicals by these plateform molecules catalyzed conversions.2005, the Dumesic research group reported first of Univ Wisconsin-Madison USA prepares the Catalytic processes (Science of long chain alkane (gasoline and diesel oil) from HMF and furfural, 2005,308:1446-1450), comprise aldol condensation, hydrotreated lube base oil, dehydration/hydrogenation three steps, reaction second step carries out at batch still, with Pd/Al
2o
3for catalyzer; 3rd step is with Pt/SiO
2-Al
2o
3for catalyzer carries out in fixed bed.Wherein, the reaction conditions of two steps is harsher, all needs high temperature or high pressure, and wherein reacting second step temperature slightly low is 120 DEG C, and the 3rd step then needs 250-265 DEG C, 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 steps are all carried out in aqueous phase, the serious carbon deposit (being equivalent to the reactant of 20-50%) caused for preventing too high temperature and the inactivation of catalyzer, devise again four complicated phase reactors, introduce n-Hexadecane as extraction agent, add investment and the separation costs of reaction unit; In addition, the long-chain products of " hard-earned " has quite a few catalyzed cracking (C-C bond rupture) under severe conditions, generates the small molecules short chain alkanes (CH that added value is not high
4~ C
5h
12), reduce the selectivity of target product long chain alkane, energy efficiency also reduces thereupon further.
The last two steps in long chain alkane technique (namely by condensation product through hydrotreated lube base oil, dehydration/hydrogenation to long chain alkane) severe reaction conditions is prepared for solving above-mentioned biomass derivatives, the problems such as the low and long chain alkane selectivity of energy efficiency is low, we have extensively studied the reaction mechanism of the last two steps.Find that open loop (fracture of C-O key) this step of tetrahydrofuran (THF) ring is difficult to occur, and once open loop occurs, then dehydration/hydrogenation will be gentle a lot, 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, for assisting the fracture of catalysis carbon-oxygen bond, make the product of aldol condensation on a catalyzer, long chain alkane can be converted into by single step reaction.Based on this thinking, we devise metal (I)-metal (II)-solid acid three center polyfunctional catalyst, metal (I) is mainly used in shortening (dissociating of hydrogen), the effect of dehydration (dehydroxylation) is mainly played in acid, and the object introducing metal (II) is concerted catalysis C―O bond cleavage (particularly the open loop of furan nucleus and tetrahydrofuran (THF) ring), improve the transformation efficiency of reaction and the selectivity to alkane, thus can under relatively mild conditions a step high yield pulp1 obtain corresponding long chain alkane, considerably increase 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 being prepared long chain alkane by polyfunctional catalyst single stage method efficient catalytic biomass derivatives.Comprise the following steps: the condensation product of biomass derivatives furfural (or HMF) and acetone, solvent and metal (I)-metal (II)-solid acid three center polyfunctional catalyst are fed into the stainless steel autoclave with polytetrafluoroethylliner liner, reactant concn 3-50%, reactant is 2-20: 1 with catalyst quality ratio, at 0-60 DEG C, high-speed stirring reaction 10min-4h under 0.5-1.5MPa hydrogen pressure, then continue reaction 4-30h at 110-190 DEG C 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, reaction effect and batch still very nearly the same.
Condensation product described in above-mentioned steps can be single condensation product C of furfural and acetone
8(4-(2-furyl)-3-butene-2-one), two condensation product C
13(two (the 2-furyl)-Isosorbide-5-Nitrae-pentadiene-3-ketone of 1,5-) or its mixture also can be single condensation product C of HMF and acetone
9(4-(5-methylol-2-furyl)-3-butene-2-one), 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, one or several in Cu, metal (II) can be the front transition element Ti with redox active (i.e. catalyzed carbon oxygen bond rupture), V, Cr, Mn, Co, Zr, Nb, Mo, Ta, W, one or more in Re, acid site can be that the compound containing 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 that produces or B acid site.The maximum feature of this Catalytic processes is exactly by design metal (I)-metal (II)-solid acid three center polyfunctional catalyst, 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, decrease the separating step of product and catalyzer; And adopt organic solvent to avoid the generation of carbon deposit, improve the life-span of catalyzer; In addition, gentle reaction conditions substantially increases the selectivity of long chain alkane, the transformation efficiency of reaction is all greater than 99.9%, yield reaches as high as 97%, thus make the whole energy efficiency preparing long chain alkane from biomass derivatives catalysis improve a very large step, really achieve low power consuming, high production, carry out energy conversion under relatively mild conditions.
Accompanying drawing explanation
Accompanying drawing is the reaction schematic diagram efficiently being prepared long chain alkane by polyfunctional catalyst single stage method.R
1for-H or-CH
2oH, R
2for-H or-CH
3.
specific embodiments
Batch still reacts:
By furfural or HMF and condensation of acetone product C 8, C9, C13, one or more mixtures 0.2-6g in C15 and solvent (methyl alcohol, ethanol, ether, tetrahydrofuran (THF), ethyl acetate, alkane, methylene dichloride, one or more mixing in ethylene dichloride) 6g drops into the intermittent high-pressure reactor of 50ml polytetrafluoroethylliner liner, namely controlling substrate mass concentration is 3-50%, add described polyfunctional catalyst 0.02-1.0g again, the mass ratio controlling substrate and catalyzer is 2-20, at 0-60 DEG C, under 0.5-1.5MPa hydrogen pressure, high-speed stirring, reaction 10min-4h, then be warming up to 110-190 DEG C and continue reaction 4-30h, obtain corresponding long chain alkane (octane, nonane, tridecane and pentadecane).
Fixed bed reaction:
First three center polyfunctional catalyst compressing tablets are ground into 40-60 order particle, then 0.4-2g catalyzer being loaded internal diameter is 6 millimeters, the stainless steel tubular reactor of long 55 millimeters, and rest part 40-60 order quartz sand is filled to reduce dead volume.Reaction tubes is put into Reaktionsofen fix and boost to 0.5-3.0MPa (hydrogen partial pressure is 0.2-1.0MPa), to ensure that whole reaction is carried out in the liquid state with the hydrogen nitrogen mixed gas of 5-100% after whole device of hunting leak.Control temperature of reaction is 110-190 DEG C, and gas flow rate is 2-100ml/min, C8, C9, C13, C15 strength of solution is 3%-50%, and solution liquid phase pump injects, and air speed is 0.5-10h
-1, reaction solution through condensation, flows into reservoir after gas-liquid separation after bed, takes out liquid in groove at set intervals and analyzes.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 thereto.
Embodiment 1
0.4g C8 (4-(2-furyl)-3-butene-2-one) and 6g solvents tetrahydrofurane are dropped into the intermittent high-pressure reactor with 50ml polytetrafluoroethylliner liner, then adds 0.1g Pd/Nb
2o
5polyfunctional catalyst, at 15 DEG C, under 1.0MPa hydrogen pressure, high-speed stirring, reaction 10min, is then warming up to 170 DEG C and continues reaction 16h, C
8transformation efficiency is 100%, and octane yield is 97%.
Embodiment 2
By 1.0g C
9(4-(5-methylol-2-furyl)-3-butene-2-one) and 6g solvent methanol drop into the intermittent high-pressure reactor with 50ml polytetrafluoroethylliner liner, then add 0.4g Ru/WO
3catalyzer, at 40 DEG C, under 1.5MPa hydrogen pressure, high-speed stirring, reaction 3h, is then warming up to 150 DEG C and continues reaction 24h, C
9transformation efficiency is 100%, and nonane yield is 51%, and all the other more also remain the intermediate product that an oxygen exists.
Embodiment 3
By 0.5g C
13(two (the 2-furyl)-Isosorbide-5-Nitrae-pentadiene-3-ketone of 1,5-) and 6g methylene chloride drop into the intermittent high-pressure reactor with 50ml polytetrafluoroethylliner liner, then add polyfunctional catalyst Pt/ZrOSO
40.2g, at 25 DEG C, under 0.8MPa hydrogen pressure, high-speed stirring, reaction 1h, is then warming up to 190 DEG C and continues reaction 4h, C
13transformation efficiency is 100%, and tridecane yield is 82%, has and produces other alkane because of carbon carbon scission of link on a small quantity.
Embodiment 4
By 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 50ml polytetrafluoroethylliner liner, then add 0.1g Pt/H
3pW
12o
40, at 50 DEG C, under 1.5MPa hydrogen pressure, high-speed stirring, reaction 4h, is then warming up to 160 DEG C and continues reaction 20h, C
15transformation efficiency is 100%, and pentadecane yield is 90%.
Embodiment 5
By 10g C
8be dissolved in the solution that 190g ethyl acetate is made into 5%, at RuNi/VOPO
4under polyfunctional catalyst effect, react in fixed-bed reactor, the hydrogen nitrogen mixed gas using 20% is as reaction gas, and at 2.5MPa, 180 DEG C, air speed is 3.6h
-1, gas flow rate is under 20ml/min condition, C
8can 100% transform, the selectivity 92% of octane.
Embodiment 6
By 16g C
15be dissolved in the solution that 184g ethanol is made into 8%, at Pd/NbOPO
4under polyfunctional catalyst effect, react in fixed-bed reactor, the hydrogen nitrogen mixed gas using 10% is as reaction gas, and at 2.0MPa, 170 DEG C, air speed is 1.2h
-1, gas flow rate is under 40ml/min condition, C
15can 100% transform, the selectivity 65% of pentadecane.
Claims (4)
1. efficiently prepared a method for long chain alkane by polyfunctional catalyst single stage method, it is characterized in that comprising the following steps:
The condensation product of biomass derivatives furfural or HMF and acetone, solvent and metal (I)-metal (II)-solid acid three center polyfunctional catalyst are fed into the stainless steel autoclave with polytetrafluoroethylliner liner, reactant concn is 3-50%, reactant is 2-20: 1 with catalyst quality ratio, at 0-60 DEG C, high-speed stirring reaction 10min-4h under 0.5-1.5MPa hydrogen pressure, then continues reaction 4-30h at 110-190 DEG C and obtains corresponding long chain alkane;
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 by equi-volume impregnating or coprecipitation method on the compound of metal (II), in catalyzer metal (I) be have in the precious metals pt of hydrogenation activity, Pd, Ru, Rh, Ir or non-noble metal Ni, Co, Cu one or several, metal (II) has one or more in the front transition element Ti of redox active, V, Cr, Mn, Co, Zr, Nb, Mo, Ta, W, Re, and acid site is the L acid site that produces of the compound containing metal (II) or B acid site.
2. the method being prepared long chain alkane by polyfunctional catalyst single stage method efficient catalytic according to claim 1, it is characterized in that, the described compound containing metal (II) comprises oxide compound, oxyhydroxide, halogenide, vitriol, phosphoric acid salt, metal acid, metal acid-salt, metal heteropolyacid, metal heteropolyacid salt.
3. efficiently prepared the method for long chain alkane by polyfunctional catalyst single stage method for one kind, it is characterized in that: describedly directly to carry out in fixed bed, at 110-190 DEG C, under 0.5-3.0MPa 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 by concentration, described raw material is condensation product, solvent by biomass derivatives furfural or HMF and acetone, reaction gas is pure hydrogen or hydrogen nitrogen mixed gas, reaction gas density of hydrogen 5-100%, reaction gas flow velocity 2-100ml/min, air speed 0.5-10h
-1;
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 by equi-volume impregnating or coprecipitation method on the compound of metal (II), in catalyzer metal (I) be have in the precious metals pt of hydrogenation activity, Pd, Ru, Rh, Ir or non-noble metal Ni, Co, Cu one or several, metal (II) has one or more in the front transition element Ti of redox active, V, Cr, Mn, Co, Zr, Nb, Mo, Ta, W, Re, and acid site is the L acid site that produces of the compound containing metal (II) or B acid site.
4. a kind of method efficiently being prepared long chain alkane by polyfunctional catalyst single stage method according to claim 3, it is characterized in that: the described compound containing metal (II) comprises oxide compound, oxyhydroxide, halogenide, vitriol, phosphoric acid salt, metal acid, metal acid-salt, metal heteropolyacid, metal heteropolyacid salt.
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| CN103977796B (en) * | 2014-05-18 | 2017-02-15 | 华东理工大学 | Catalyst used in preparation of long-chain alkane through catalytic hydrodeoxygenation of biomass |
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| CN108558794A (en) * | 2018-05-17 | 2018-09-21 | 北京化工大学 | A kind of preparation method for reacting synthesis light-sensitive compound according to Claisen-Schmidt |
| 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 |
| 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 |
| 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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