CN105273739B - Preparation method for aviation kerosene - Google Patents
Preparation method for aviation kerosene Download PDFInfo
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Abstract
A preparation method for aviation kerosene is disclosed, and relates to a new route for synthesizing a liquid-state branched paraffin fuel under effect of a cheap catalyst by taking lignocelluloses-based platform compound completely no depending on fossil energy as a raw material. The liquid-state fuel obtained through the route can be used as an aviation kerosene (or diesel oil) substitute or an additive for improving fuel cetane value and cold resistance. The method is divided into two parts, and concretely comprises 1) a lignocelluloses-base furfural compound (comprising furfural, methylfurfural or 5-hydroxymethylfurfural) and a carboxyl-containing compound (comprising 3-pentanone, 5-nonanone and the like) are subjected to an aldol condensation reaction under the effect of a base catalyst for synthesizing an oxygen-containing organic compound with the carbon chain length of 8-16; and 2) the aldol condensation product is subjected to direct oxidative dehydrogenation under the effect of a non-noble metal catalyst for obtaining biomass aviation kerosene branched-chain hydrocarbons which possesses the carbon chain length of 8-16 and possesses relatively high energy density, stability and relatively low freezing point.
Description
Technical field
The present invention relates to a kind of lignocellulose based platform compound with the non-fossil energy is as raw material, synthesize aerial kerosene
Variation route, specifically include two steps：1) lignocellulose base Furnan products are (including furfural, methyl furfural or 5- hydroxyls
Methyl furfural) and carbonyl containing compound (including propione, butyl ketone etc.) by aldol reaction generate carbon chain lengths 8 to
Oxygen-containing organic compound between 16；2) Aldol Condensation Products are carried out with direct hydrogenation by supported non-precious metal catalyst to take off
Oxygen, so as to obtain branched paraffin of the carbon chain lengths between 8 to 16.Compared with the work having been reported, the boat of this work synthesis
Empty kerosene is branched-chain hydrocarbons, with relatively low freezing point, is widely used as biomass aerial kerosene or diesel oil.
Background technology
Aerial kerosene, as the liquid fuel being in great demand in the world at present, is the strategic goods and materials of a country.It
With the properties such as high-flash, low-freezing, high density and heats of combustion value, the hydrocarbon mixture institute usually by carbon number between 8-16
Composition.At present, aerial kerosene is mainly with petroleum refining, yet with the non-renewable and people couple of fossil resource
In the growing interest of environmental problem, finding reproducible organic carbon source replacing oil to prepare aerial kerosene becomes countries in the world
Study hotspot.Compared with fossil energy, the characteristics of biomass fuel has recyclability and carbon dioxide neutral.Biology boat coal
Sulfur dioxide given off in burning etc. is well below mineral fuel oil.Therefore, research and develop biological boat coal solve Current resource and
Constraint of the environment to developing, has its own strategic significance for ensureing Chinese energy safety, obtaining green low-carbon competitive advantage.
The rise of biomass fuel experienced certain evolution.First generation biomass fuel is with corn and soybean etc.
Raw material prepares bio-ethanol and biodiesel by reactions such as fermentation, ester exchanges.This route with edible grain as raw material,
Be not suitable for the national conditions that China has a large population and a few land.Second filial generation biomass fuel passes through three kinds of approach with agriculture and forestry organic waste material as raw material, mainly
Generate fuel：1) gasification of biomass is processed and generates synthesis gas, then alkane is produced in the synthesis of funds support.The process comparative maturity,
However it is necessary that the condition of High Temperature High Pressure, energy consumption is huge；2) biomass high temperature pyrolysis generate bio-oil, then Jing deoxidations escalate into liquid
State fuel.The process is complicated, and obtained bio-oil inferior quality, it is impossible to be directly used as engine fuel, needs further essence
Refining；3) biomass obtain small molecule platform thing (including hydrolysis, fermentation, selective hydrogenation etc.) by chemistry and biological treatment, then
Containing with aerial kerosene chain length (C8-C16) is obtained by C-C coupling reaction by raw material of these small molecule platform chemicals
Oxygen organic compound.Finally, these oxygen-containing organic compounds are carried out with hydrogenation deoxidation reaction liquid alkane is obtained.The process condition
It is relatively gentle, and synthetic route is versatile and flexible.
The method for synthesizing aerial kerosene by approach three has：
1st, hydroxyalkylation/alkylated reaction --- hydrogenation deoxidation reacts
2011, Corma et al. reported methylfuran and butyraldehyde, 5 methyl furfural, 5 hydroxymethyl furfural under acid catalysiss
Between alkylated reaction and its own trimerization reaction be prepared for it is oxygen-containing organic with aerial kerosene or diesel oil chain length range
Compound, thereafter, they are a series of with more subzero aviation coal further through obtaining to these compound hydrogenation deoxidations
Oily branched-chain hydrocarbons (Angew.Chem.Int.Ed.2011,50,1-5).But the method adopts sulphuric acid and toluene sulfonic acide for catalyst
The corrosion to equipment and the pollution to environment can be caused.Then, the seminar reports 5 methyl furfural and 2- methylfurans again
Alkylated reaction, and adopt Pt/C, Pt/C-TiO2As hydrogenation deoxidation catalyst, higher liquid phase alkane yield is obtained.
On this basis, we organize by a series of solid acid catalysts be catalyzed methylfuran and furfural, butyraldehyde, acetone, hydroxypropanone-,
A series of oxygen-containing organic compounds with aerial kerosene or diesel oil chain length range of levulic acid Lipase absobed, then by this
A little compound hydrogenation deoxidations obtain a series of with more subzero aerial kerosene branched-chain hydrocarbons.Because this method is with furfural
Selection hydrogenation products methylfuran be the relatively high (Chinese Patent Application No. of cost of material：201110346501.1；China
Patent 201210169817.2).
2nd, aldol reaction --- hydrogenation deoxidation reacts
2005, Dumesic, Huber et al. [Science, 2005,308,1446-1450] and patent [US7,671,
246] report with Hydroxymethylfurfural or furfural and acetone as raw material, by the aldol reaction and hydrogenation of base catalysiss and add
Hydrogen deoxygenation has produced the liquid alkane of C8 to C15 scopes.Author is with Pt/SiO2-Al2O3For hydrogenation deoxidation catalyst, adopt
The phase flow reactor of fixed bed four, needs to be passed through organic solvent (such as hexadecane) to prevent catalyst from inactivating, technique ratio in course of reaction
It is more complicated.2008, the seminar replaced sial composite oxides to make carrier using the niobium oxide of phosphorylation.It was found that using new
Organic solvent need not be passed through after carrier in reaction system can also obtain good effect, so as to simplify technique
(ChemSusChem,2008,1,417-424).But because the alkane of the process synthesis is linear paraffin, these hydro carbons
Very high (the Pentadecane of freezing point：8.5-10 DEG C, n-tridecane：- 5.5 DEG C, n-dodecane:- 12 DEG C), do not meet aerial kerosene
Require (fusing point is less than -40 DEG C).Need to be processed by further hydroisomerizing and just can serve as aerial kerosene.On this basis, we
Group under condition of no solvent with 2 pentanone, 2-heptanone carries out aldol condensation respectively with furfural as substrate, by it and hydrogenation deoxidation is anti-
Should, obtaining the liquid alkane of C9-C12 scopes, the liquid alkane of the method synthesis is direct-connected alkane, and wherein hydrogenation deoxidation
Reaction adopts loaded noble metal catalyst.
The work of biomass hydrogenation deoxidation Synthin most in the world at present is all catalyzed using noble metal support type
Agent, if noble metal can be replaced using cheap base metal, will substantially reduce the production cost of biological aviation fuel；And, attempt
More lignocellulose based platform compounds are reaction substrate, widen the reaction scheme that boat coal or diesel oil are prepared by biomass,
This would be even more beneficial to the industrialization of biomass aerial kerosene technology.
The content of the invention
It is an object of the invention to provide one from platform chemicals derived from lignocellulose, low-freezing is prepared
The variation route of aerial kerosene.
The present invention is achieved through the following technical solutions：
The first step is by the aldol condensation between base catalysiss lignocellulose base Furnan products and carbonyl containing compound
Oxygen-containing organic compound of the carbon chain lengths between 8～16 is produced in reaction；
Lignocellulose base Furnan products are：One or more in furfural, methyl furfural or 5 hydroxymethyl furfural；
Lignocellulose base carbonyl containing compound is：One kind or mixture in propione, butyl ketone；Base catalyst solid base, including
Alkaline-earth oxide (MgO, CaO), alkaline earth and rare earth mixed oxide (CaO-CeO2、MgO-La2O3), magnesium aluminum-hydrotalcite, CeO2、
MgO-ZrO2、KF/Al2O3Deng；
The step adopts batch tank reactor.Lignocellulose base Furnan products and carbonyl containing compound mol ratio
For 5:1 to 1:5, preferably 1:2, unreacted raw material is retortable to be removed and recycles；Reaction temperature is excellent between 0-200 DEG C
Elect 150～190 DEG C as；Response time is 1-24h, preferably 8～12h；Reaction can be carried out under condition of no solvent.
Second step obtains carbon chain lengths using supported non-precious metal catalyst to the deoxidation of Aldol Condensation Products direct hydrogenation
Between 8～16 with high-energy-density, high stability, subzero branched paraffin.These branched-chain hydrocarbons can be used as biology
Matter aerial kerosene or diesel oil；
Using supported non-precious metal catalyst to Aldol Condensation Products direct hydrogenation deoxidation.Carried metal using Cr, Fe,
One or more in Co, Ni, Cu；Catalyst carrier selects aluminium oxide, silicon oxide, sial complex carrier, molecular sieve, acid
One or more mixture in property metal-oxide；
Load type metal catalyst is prepared using the method for incipient impregnation：By the metal front liquid solution of 2-10%, press
Than being added to the medium volume impregnation of corresponding carrier, the content of metal accounts for 0.5-10% in catalyst for metering, does after 4h is stood
Dry 8-24h, then 200-600 DEG C in Muffle furnace at roasting 4-6h, finally the hydrogen reducing 3-5h at 200-600 DEG C.
Aldol Condensation Products directly feed through vacuum distillation purification process.Reaction passes through under the conditions of liquid solvent-free
Fixed bed reactors carry out direct hydrogenation deoxygenation；
The condition of fixed bed reactors is：Temperature between 200-400 DEG C, reaction pressure between 0.1-10.0MPa, reaction
Thing/catalyst quality air speed is in 0.1-10.0h-1, H2It is 20-1500 with the mol ratio of substrate.
By above step, the aerial kerosene branched paraffin high income of acquirement is up to 90%.Realize and spread out with lignocellulose
The biological cheap easy novel synthetic that low-freezing aerial kerosene is prepared for raw material.
Description of the drawings
Fig. 1 furfurals are schemed with propione Aldol Condensation Products H-NMR；
Fig. 2 furfurals are schemed with propione Aldol Condensation Products C-NMR；
The hydrogenation deoxidation product GC spectrograms of Fig. 3 Aldol Condensation Products A；
The MS spectrograms of Fig. 3 (a) hydrogenation deoxidation product 4- methyl-octane and standard spectrogram are contrasted；
The MS spectrograms of Fig. 3 (b) hydrogenation deoxidation product 4- methyl-nonane and standard spectrogram are contrasted.
Specific embodiment
Embodiment 1-10
1. the preparation of catalyst：
1) preparation of solid base catalyst：Alkaline-earth oxide (MgO, CaO) is the commercial catalysts product of direct purchase.
CeO2By corresponding nitrate in N2Calcine 8h under atmosphere to obtain.Alkaline earth and rare earth mixed oxide (CaO-CeO2、MgO-La2O3)
By coprecipitation by 20wt%NH3.H2O be added drop-wise to by certain mol proportion mix two kinds of nitrate solutions in, pH regulator to 9,
1h is persistently stirred, 80 DEG C are dried overnight, 650 DEG C of calcining 8h.Magnesium aluminum-hydrotalcite be by mol ratio be 3:1 Mg (NO3)2·6H2O
With Al (NO3)3·9H2O mixed solutions are added dropwise to NaOH and NaCO with 3mL/min3Mixed solution in ([CO3]/[Al]+[Mg]
=0.53, [OH]/[Al]+[Mg]=2.33), Deca process is carried out under 70 DEG C of water-bath strong agitation.Continue after completion of dropwise addition
Aging 16h is stirred, then filtration washing, be dried overnight in 80 DEG C, 450 DEG C of calcining 8h obtain final product magnesium aluminum-hydrotalcite.KF/Al2O3Adopt
Excessive infusion process is used, by γ-Al2O3In being added to a certain amount of KF solution, after 70 DEG C of stirring in water bath 1h, revolving eliminating water, in
120 DEG C are dried 4h, obtain the KF/ γ-Al of theoretical loading 35%2O3Catalyst.MgO-ZrO225%NaOH solution is added drop-wise to
Mg (the NO of certain mol proportion mixing3)2·6H2O and ZrO (NO3)2In solution, until pH=10, aged at room temperature 72h, cross diafiltration
Wash, 80 DEG C are dried overnight, 600 DEG C of calcining 8h.All solids base catalyst is using being front intended in N2Pretreatment 2h in atmosphere.
2) preparation of hydrogenation deoxidation catalyst：Chromic nitrate, ferric nitrate, cobalt nitrate, nickel nitrate, copper nitrate or mixed solution,
By metering volume impregnation more medium than addition catalyst carrier, 4h is then stood, be dried overnight at 60 DEG C, 500 DEG C of roasting 4h are being urged
Agent need to use hydrogen reductase 12 h at 500 DEG C using front, synthesize the catalyst that metal quality percent is 5%.Institute in the present invention
Silicon oxide is the commercial silica for being ground to 200 mesh.Obtained catalyst is shown in Table 1.
The metal-solids acid catalyst of table 1
a:The Theoretical Mass percentage ratio of nickel and copper (or ferrum) is 2.5% in catalyst.
Embodiment 11-21
2. aldol reaction：18g furfurals, 33g3- pentanones (or mol ratio 1 are added in the reactor of 100mL:2 wood
Matter cellulose base Furnan products and carbonyl containing compound), 3g catalyst (catalyst ratio 6wt%), at 170 DEG C stir
8h.Detailed reaction the results are shown in Table 2.
The aldol reaction of table 2 and its result
The aldol condensation target product structural formula of table 3
As can be seen from Table 2, in different solid base catalysts：MgO、CaO、CeO2、MgO-La2O3、CaO-CeO2, water
Talcum, KF/Al2O3、MgO-ZrO2Under catalytic action, the Aldol Condensation Products for having certain yield are generated.Wherein with CaO, KF/
Al2O3Activity is best.Because CaO has the characteristics of preparing simple, cheap and easy to get, we select the catalyst to be furtherd investigate.
Embodiment 22-26
1) impact of the differential responses substrate ratios to furfural and propione aldol reaction product yield
Impact of the differential responses substrate ratios of table 4. to A yields
As can be seen from Table 4, when the mol ratio of furfural and propione is 1:Product A yield highests when 2.
Embodiment 27-31
2) impact of the differential responses temperature to furfural and propione aldol reaction product yield
Impact of the differential responses temperature proportional of table 5. to A yields
As can be seen from Table 5, the product A yield highests when reaction temperature is 170 DEG C.
Embodiment 32-35
3) impact of the differential responses time to furfural-propione reaction yield
Impact of the differential responses time of table 6. to aldol reaction product A yields
As can be seen from Table 6, when the response time is 8h, product A yields basically reach stable.
Embodiment 36-45
3. hydrogenation deoxidation reaction：In fixed bed reactors, 1.8g catalyst is fitted in reaction tube, in keeping reactor
Pressure is 6.0MPa, 350 DEG C of temperature, hydrogen flow rate 120mL/min, by through the aldol condensation product of vacuum distillation purification process
A efficient liquid-phase chromatographic pumps are pumped in reactor with 0.04mL/min.Reaction result is shown in Table 7.
Impact of the catalyst of table 7. to hydrogenation deoxidation reactivity
| Embodiment | Catalyst | C1-C10 alkane yields | C8 to C10 alkane yields |
| Embodiment 36 | Cr/SiO2 | 12% | 10% |
| Embodiment 37 | Fe/SiO2 | 15% | 15% |
| Embodiment 38 | Co/SiO2 | 87% | 65% |
| Embodiment 39 | Ni/SiO2 | 96% | 75% |
| Embodiment 40 | Cu/SiO2 | 70% | 51% |
| Embodiment 41 | Ni-Cu/SiO2 | 94% | 85% |
| Embodiment 42 | Ni-Fe/SiO2 | 89% | 75% |
| Embodiment 43 | Ni-Cu/Al2O3 | 95% | 70% |
| Embodiment 44 | Ni-Cu/SiO2-Al2O3 | 93% | 75% |
| Embodiment 45 | Ni-Cu/C | 88% | 79% |
As can be seen from Table 7, when raw material is without adding under conditions of any solvent, in addition to Cr, Fe loaded catalyst,
Other catalyst substantially carry out complete hydrogenation deoxidation, and Ni, Cu and its Alloy type catalyst obtain ideal yield coefficient
, branched paraffin in the range of aerial kerosene.
Embodiment 46-56
1) in fixed bed reactors, the quality of different Hydrogen Vapor Pressure, reaction temperature, reaction raw materials and catalyst is empty
Speed, hydrogen flowing quantity are shown in Table 8 to the impact that hydrogenation deoxidation reacts.Raw material is the aldol condensation product A, catalyst n i- of purification process
Cu/SiO2。
The temperature of table 8., the impact of pressure, mass space velocity, hydrogen flowing quantity to hydrogenation deoxidation reactivity
As can be seen from Table 8, when temperature is more than 350 DEG C, mass space velocity is less than 1h-1, reaction pressure is more than 6MPa, hydrogen stream
When amount is more than 120mL/min, comparatively ideal alkane yield can be obtained.
Claims (7)
1. a kind of preparation method of aerial kerosene, it is characterised in that：
1) under base catalysiss, lignocellulose base Furnan products and carbonyl containing compound produce carbon by aldol reaction
Oxygen-containing organic compound of the chain length between 8 to 16；
2) using supported non-precious metal catalyst to Aldol Condensation Products direct hydrogenation deoxidation, so as to obtain carbon chain lengths 8
Aerial kerosene branched paraffin between 16；
The lignocellulose base Furnan products are：One or two in furfural, 5 methyl furfural, 5 hydroxymethyl furfural
Mixture above；
The carbonyl containing compound is：One or more mixture in propione, butyl ketone.
2. according to the preparation method described in claim 1, it is characterised in that：
In step 1) in, the catalyst under the base catalysiss is solid base, including alkaline-earth oxide, alkaline earth and rare earth mixed oxidization
Thing, magnesium aluminum-hydrotalcite, CeO2、MgO-ZrO2、KF/Al2O3In one or more mixture, wherein, alkaline-earth oxide
For MgO, CaO, alkaline earth and rare earth mixed oxide are CaO-CeO2、MgO-La2O3；
Lignocellulose base Furnan products are 5 with the mol ratio of carbonyl containing compound:1 to 1:5.
3. according to the preparation method described in claim 1 or 2, it is characterised in that：
In step 1) in, using batch tank reactor；At 0-200 DEG C, the response time is 1-24h to reaction temperature；Reaction can be
Liquid has under solvent or condition of no solvent to be carried out；Unreacted raw material can be removed and followed by distillation or rectification from reaction system
Ring is used.
4. according to the preparation method described in claim 1, it is characterised in that：
In step 2) in, using supported non-precious metal catalyst to Aldol Condensation Products direct hydrogenation deoxidation, carried metal is adopted
With one or more in Cr, Fe, Co, Ni, Cu；Catalyst carrier from aluminium oxide, silicon oxide, sial complex carrier,
One or more mixture in molecular sieve, acidic metal oxide；
Carried metal is 2-10% in catalyst quality load capacity.
5. according to the preparation method described in claim 1 or 4, it is characterised in that：
Load type metal catalyst is prepared using the method for incipient impregnation：By metal front liquid solution, it is added to by metering ratio
The corresponding medium volume impregnation of carrier, is dried 8-24h after 4h is stood, then 200-600 DEG C in Muffle furnace at roasting 4-6h, most
The hydrogen reducing 3-5h at 200-600 DEG C afterwards.
6. according to the preparation method described in claim 1 or 4, it is characterised in that：
In step 2) in, Aldol Condensation Products are carried out with direct hydrogenation deoxidation catalytic reaction, reactant using fixed bed reactors
Without solvent in system；
The condition of fixed bed reactors is：Temperature between 200-400 DEG C, reaction pressure between 0.1-10.0MPa, aldol condensation
Product/catalyst quality air speed is in 0.1-10.0h-1, H2It is 20-1500 with the mol ratio of Aldol Condensation Products.
7. according to the preparation method described in claim 1 or 2, it is characterised in that：
In step 1) in, the base catalyst consumption is the 6% of reaction raw materials gross mass.
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| EP3301142B1 (en) * | 2016-09-29 | 2020-11-18 | Neste Oyj | Upgrading 5-nonanone |
| CN106381165B (en) * | 2016-10-31 | 2018-08-14 | 新奥生态环境治理有限公司 | A kind of combustible organic plus hydrogen method for upgrading |
| CN107488457B (en) * | 2017-09-14 | 2019-07-16 | 陕西理工大学 | A kind of biomass liquid fuel and the preparation method and application thereof |
| CN109718850B (en) * | 2017-10-31 | 2022-02-11 | 中国科学院大连化学物理研究所 | Method for preparing aviation kerosene precursor |
| CN108559572A (en) * | 2018-06-19 | 2018-09-21 | 盐城市顺天铸造有限公司 | A kind of solid fuel and preparation method thereof based on agricultural crop straw |
| CN110079355B (en) * | 2019-04-26 | 2020-08-04 | 中国科学院山西煤炭化学研究所 | Aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation and synthesis method |
| CN110302789A (en) * | 2019-06-27 | 2019-10-08 | 中国科学院广州能源研究所 | A kind of Na-NiAl (O) catalyst and its application in the biological aviation fuel presoma of preparation |
| CN113444540B (en) * | 2020-03-25 | 2022-10-21 | 中国石油化工股份有限公司 | Biological aviation kerosene component oil and preparation method thereof |
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| US7671246B2 (en) * | 2006-03-06 | 2010-03-02 | Wisconsin Alumni Research Foundation | Method to make alkanes and saturated polyhydroxy compounds from carbonyl compounds |
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| CN103805224A (en) * | 2012-11-06 | 2014-05-21 | 中国科学院大连化学物理研究所 | Preparation method for aviation kerosene |
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| US7671246B2 (en) * | 2006-03-06 | 2010-03-02 | Wisconsin Alumni Research Foundation | Method to make alkanes and saturated polyhydroxy compounds from carbonyl compounds |
| US7880049B2 (en) * | 2006-06-06 | 2011-02-01 | Wisconsin Alumni Research Foundation | Production of liquid alkanes in the jet fuel range (C8-C15) from biomass-derived carbohydrates |
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