CN110079355B - Aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation and synthesis method - Google Patents

Aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation and synthesis method Download PDF

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CN110079355B
CN110079355B CN201910345771.7A CN201910345771A CN110079355B CN 110079355 B CN110079355 B CN 110079355B CN 201910345771 A CN201910345771 A CN 201910345771A CN 110079355 B CN110079355 B CN 110079355B
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isobutyl ketone
methyl isobutyl
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fuel oil
aviation fuel
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CN110079355A (en
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邓天昇
柴琳
侯相林
王英雄
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Shanxi Institute of Coal Chemistry of CAS
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42Catalytic treatment
    • C10G3/44Catalytic treatment characterised by the catalyst used
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42Catalytic treatment
    • C10G3/44Catalytic treatment characterised by the catalyst used
    • C10G3/45Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42Catalytic treatment
    • C10G3/44Catalytic treatment characterised by the catalyst used
    • C10G3/47Catalytic treatment characterised by the catalyst used containing platinum group metals or compounds thereof
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00Technologies relating to oil refining and petrochemical industry
    • Y02P30/20Technologies relating to oil refining and petrochemical industry using bio-feedstock

Abstract

The invention belongs to the technical field of aviation fuel synthesis, and particularly relates to aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation and a synthesis method thereof. Dispersing a metal salt catalyst in methyl isobutyl ketone, placing the methyl isobutyl ketone in a reaction kettle for heating reaction, cooling to room temperature after the reaction is finished, taking out reaction liquid for standing and layering, placing the product in the reaction kettle, introducing hydrogen, adding the metal catalyst into a reaction system, and carrying out hydrogenation reaction under the catalysis of the metal catalyst to obtain the aviation fuel oil with the freezing point within the range of (-40) - (-58) DEG C and the yield of 80-95%. The aviation fuel obtained by the method has the advantages of low freezing point, mild production conditions, less side reactions in the production process, higher purity of the obtained product and good application prospect.

Description

Aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation and synthesis method
Technical Field
The invention belongs to the technical field of aviation fuel oil synthesis, and particularly relates to aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation and a synthesis method thereof.
Background
With the increasing energy crisis, the liquid fuel produced by distillation, cracking and other processes with crude oil as raw material is irreproducible, which is contrary to the concept of sustainable development. The aviation fuel oil is a strategic material of China, and has great significance in developing a sustainable method of low-cost and regenerated substances for reducing the dependence on fossil-based oil, reducing the cost and realizing aviation emission reduction.
The biomass belongs to renewable energy sources, and the preparation of the aviation fuel oil by using the biomass has many advantages, such as wide raw material sources, clean and pollution-free production process, high product purity and the like, and the biomass-based aviation fuel oil is expected to become an ideal power fuel production technology. In the current report, 5-hydroxymethyl furfural, furfural and acetone, methyl furan and butyraldehyde, lignocellulose-based furfural compounds and methyl isobutyl ketone are generally combined as raw materials, and liquid alkanes in the range of C8-C16 are prepared through an aldol condensation reaction catalyzed by alkali or acid, and then through low-temperature hydrogenation and hydrodeoxygenation steps. The furfural and 5-hydroxymethyl furfural have high production cost, so that the application of the furfural derivative as the raw material increases the production cost of the process; the condensation of acetone, butyraldehyde and other small molecules can occur in the condensation process, and the condensation product is not in the scope of aviation fuel oil, so that the product quality is affected; when lignocellulose-based furfural compounds and methyl isobutyl ketone are combined as raw materials, the production process is complex, and the purity of the product is difficult to ensure.
Disclosure of Invention
Aiming at the technical problems, the invention provides aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation and a synthesis method thereof.
In order to realize the technical scheme, the technical scheme adopted by the invention is as follows:
the aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation mainly comprises long-chain alkane of C12 and C18, has a plurality of branched chains, has a freezing point within the range of (-40) - (-58) DEG C, and has a yield of 80-95 percent.
A synthetic method for synthesizing aviation fuel oil by methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing a metal salt catalyst in methyl isobutyl ketone, placing the methyl isobutyl ketone in a reaction kettle, heating for aldol condensation reaction, cooling to room temperature after the reaction is finished, taking out reaction liquid, standing for layering, taking out supernatant, placing the supernatant in the reaction kettle, introducing hydrogen, adding the metal catalyst into a reaction system, and carrying out hydrogenation reaction under the catalysis of the metal catalyst to obtain a product, namely the aviation fuel oil.
The methyl isobutyl ketone contains 6 carbon atoms and relatively more branched chains, products obtained after the condensation of the methyl isobutyl ketone and the methyl isobutyl ketone for the first time and the second time are in the aviation fuel oil category, other side reactions do not exist, and the products can be directly subjected to hydrodeoxygenation under mild conditions to obtain the aviation fuel oil liquid chain hydrocarbon with the branched chains and the low freezing point.
Furthermore, the preferable cation of the metal salt catalyst is Na+、Mg2+、Al3+、Cu2+、Cu+、Fe3+、Zn2+、Ca2+One or a mixture of more than two of halide, sulfate, nitrate and acetate in any proportion. The metal salt compounds are found to be relatively weak in alkalinity in the methyl isobutyl ketone, and can catalyze the aldol condensation reaction of the methyl isobutyl ketone.
Still further, the metal catalyst selected is preferably a noble metal catalyst comprising: one or more of platinum, palladium, ruthenium, nickel and copper, or one or more of supported catalysts of the noble metal catalysts which take activated carbon, alumina, silica and zirconia as carriers, wherein the content of metal active components in the supported catalysts is 0.1-10%. Experiments show that the noble metals or the supported noble metals have better effect in hydrogenation reaction. The preparation method of the supported metal catalyst is an isometric impregnation method: preparing 1-20% of metal precursor solution, adding corresponding equal-volume impregnation according to the metering ratio, wherein the content of metal in the catalyst accounts for 0.1-10%, standing for 6h, drying at 70-140 ℃ for 12-20 h, introducing hydrogen at 200-600 ℃ for 2-6 h, cooling to room temperature, and introducing high-purity nitrogen for passivation for 4-8 h.
Furthermore, the mass ratio of the metal salt catalyst to the methyl isobutyl ketone is 1: 1-200. Experiments show that when the metal salt catalyst is added in an excessive amount, on one hand, waste is caused, and on the other hand, the excessive metal salt substance influences the purity of the product and reduces the quality of aviation fuel oil; when the amount of the methyl isobutyl ketone is excessive, the generated product contains the unreacted methyl isobutyl ketone, and the methyl isobutyl ketone does not belong to the category of aviation fuel oil, so that the purity and the quality of the product are influenced.
Further, the temperature of the aldol condensation reaction is 180-300 ℃. Experiments show that when the reaction temperature is lower than 180 ℃, the condensation reaction can not completely occur, and the generation of products is influenced; when the temperature is higher than 300 ℃, side reactions are increased, which is not beneficial to the generation of aviation fuel oil.
Furthermore, the time of the aldol condensation reaction is 2 to 20 hours. Experiments show that when the reaction time is less than 2 hours, the methyl isobutyl ketone can not be completely reacted; when the reaction time exceeds 20h, the methyl isobutyl ketone has reacted completely, and the prolonged time has no obvious influence on the reaction, thereby causing resource waste.
Furthermore, the addition amount of the metal catalyst is 0.01 to 0.1 time of the mass of the supernatant liquid. When the addition amount of the metal catalyst is excessive, on one hand, waste is caused, and on the other hand, the excessive metal substances influence the purity of the product and reduce the quality of aviation fuel oil; when the supernatant is excessive, the produced product contains unreacted supernatant, and the supernatant does not belong to the category of aviation fuel oil, so that the purity and the quality of the product are influenced.
Furthermore, the pressure in the reaction kettle is 0.1-2MPa by introducing hydrogen. Experiments show that when the hydrogen pressure is lower than 0.1MPa, the condensation product can not be completely hydrogenated, so that aviation fuel oil can not be generated finally; when the pressure exceeds 2MPa, the condensation product is completely hydrogenated, which causes resource waste.
Further, the reaction temperature of the hydrogenation reaction is 100-300 ℃. Experiments show that when the reaction temperature is lower than 100 ℃, the hydrogenation reaction can not completely occur, and the generation of aviation fuel oil is influenced; when the temperature is higher than 300 ℃, resource waste is caused.
Furthermore, the reaction time of the hydrogenation reaction is 2-20 h. Experiments show that when the reaction time is less than 2 hours, the hydrogenation reaction can not completely occur; when the reaction time exceeds 20h, the hydrogenation reaction is complete, and the extension time has no obvious influence on the reaction, thereby causing resource waste.
The invention takes methyl isobutyl ketone as raw material, under the catalytic action of metal salt catalyst, aldol condensation reaction is carried out, and the condensation reaction product is directly hydrogenated to remove oxygen to obtain the aviation fuel oil with branched chain and low freezing point. The structure of the product is verified through liquid nuclear magnetism characterization, and the freezing point of the aviation fuel oil generated by the method is measured to be within the range of (-40) - (-58) DEG C, so that the freezing point requirement of the aviation fuel oil is met. The calculated yield of the method is between 80 and 95 percent, the production condition is mild, the side reaction in the production process is less, and the purity of the obtained product is higher.
Drawings
FIG. 1 is a liquid for aviation fuel oil synthesized by aldol condensation of methyl isobutyl ketone according to the invention1An H-NMR spectrum;
FIG. 2 liquid of aviation fuel oil synthesized by aldol condensation of methyl isobutyl ketone according to the invention13C-NMR spectrum.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the main components of the aviation fuel oil are multi-branched chains, the freezing point is-48 ℃, and the yield is 86%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of ferric chloride in 5ml (4g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 180 ℃ for aldol condensation reaction for 12 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; putting 3g of the methyl isobutyl ketone condensation product into a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 1MPa, adding 0.03g of platinum into the reaction system, heating to 100 ℃, and carrying out hydrogenation reaction for 20 hours to obtain the product, namely the aviation fuel oil.
Example 2
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the number of branched chains is large, the freezing point is-40 ℃, and the yield is 92%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of sodium chloride in 50ml (40g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 230 ℃ for aldol condensation reaction for 6 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; and (2) putting 30g of the methyl isobutyl ketone condensation product into a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 1.5MPa, adding 3g of nickel into the reaction system, heating to 200 ℃ and carrying out hydrogenation reaction for 10 hours to obtain the product, namely the aviation fuel oil.
Example 3
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the main components of the aviation fuel oil are multi-branched chains, the freezing point is-58 ℃, and the yield is 95%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of copper sulfate in 100ml (80g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 300 ℃ for aldol condensation reaction for 2 hours, cooling the mixture to room temperature after the reaction is finished, taking out the reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; putting 60g of methyl isobutyl ketone condensation product into a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 2MPa, adding 3g of supported catalyst palladium/active carbon (the palladium content is 0.1%) into a reaction system, heating to 300 ℃, and carrying out hydrogenation reaction for 2 hours to obtain the product, namely the aviation fuel oil.
Example 4
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the main components of the aviation fuel oil are multi-branched chains, the freezing point is-43 ℃, and the yield is 80%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 4g of magnesium sulfate in 5ml (4g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 250 ℃ for aldol condensation reaction for 20 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing and layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; 3g of methyl isobutyl ketone condensation product is placed in a reaction kettle, hydrogen is introduced to ensure that the hydrogen pressure in the reaction kettle is 0.1MPa, 0.09g of load type catalyst copper/active carbon (the copper content is 10 wt.%) is added into a reaction system, and the reaction system is heated to 150 ℃ for hydrogenation reaction for 7 hours to obtain the aviation fuel oil.
Example 5
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the main components of the aviation fuel oil are multi-branched chains, the freezing point is-52 ℃, and the yield is 89%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of zinc nitrate in 25ml (20g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 200 ℃ for aldol condensation reaction for 15 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; putting 15g of the methyl isobutyl ketone condensation product into a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 0.5MPa, adding 1.2g of supported catalyst ruthenium/alumina (ruthenium content is 5 wt.%) into the reaction system, heating to 250 ℃ for hydrogenation reaction for 12 hours, and obtaining the product, namely the aviation fuel oil.
Example 6
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the number of branched chains is large, the freezing point is-56 ℃, and the yield is 82%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of cuprous nitrate in 75ml (60g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 270 ℃ for aldol condensation reaction for 8 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; putting 45g of methyl isobutyl ketone condensation product into a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 0.2MPa, adding 4.05g of supported catalyst platinum/silicon dioxide (the platinum content is 2 wt.%) into a reaction system, heating to 280 ℃ for hydrogenation reaction for 15 hours, and obtaining the product, namely the aviation fuel oil.
Example 7
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the number of branched chains is large, the freezing point is-41 ℃, and the yield is 88%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of sodium acetate in 35ml (28g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 190 ℃ for aldol condensation reaction for 10 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; placing 21g of the methyl isobutyl ketone condensation product in a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 1.7MPa, adding 0.84g of load type catalyst copper/zirconia (the copper content is 1 wt.%) into the reaction system, heating to 120 ℃ to perform hydrogenation reaction for 18h, and obtaining the product, namely the aviation fuel oil.
Example 8
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the main components of the aviation fuel oil are multi-branched chains, the freezing point is-50 ℃, and the yield is 83%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of calcium acetate in 90ml (72g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 280 ℃ for aldol condensation reaction for 17 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; putting 54g of the methyl isobutyl ketone condensation product into a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 1.9MPa, adding 3.78g of supported catalyst palladium/zirconia (the palladium content is 8 wt.%) into the reaction system, heating to 220 ℃ for hydrogenation reaction for 19 hours, and obtaining the product, namely the aviation fuel oil.
Example 9
The aviation fuel oil synthesized by the methyl isobutyl ketone aldol condensation in the embodiment mainly comprises long-chain alkanes of C12 and C18, the main components of the aviation fuel oil are multi-branched chains, the freezing point is-57 ℃, and the yield is 91%.
The method for synthesizing the aviation fuel oil by the methyl isobutyl ketone aldol condensation comprises the following steps:
dispersing 0.4g of metal salt catalyst mixed with copper nitrate and sodium chloride in a mass ratio of 1:1 in 45ml (36g) of methyl isobutyl ketone, placing the mixture in a reaction kettle, heating the mixture to 260 ℃ for aldol condensation reaction for 18 hours, cooling the mixture to room temperature after the reaction is finished, taking out reaction liquid, standing the reaction liquid for layering, and taking out supernatant to obtain a methyl isobutyl ketone condensation product; putting 33.8g of methyl isobutyl ketone condensation product into a reaction kettle, introducing hydrogen to ensure that the hydrogen pressure in the reaction kettle is 1.2MPa, adding 0.7g of metal catalyst with the mass ratio of platinum to palladium being 1:1 into the reaction system, heating to 170 ℃, and carrying out hydrogenation reaction for 6 hours to obtain the product, namely the aviation fuel oil.
The metal salt catalyst in the above embodiment may also be replaced by one or a mixture of two or more of calcium chloride, aluminum chloride, cuprous chloride, zinc chloride, sodium sulfate, zinc sulfate, calcium sulfate, cuprous sulfate, sodium nitrate, magnesium nitrate, calcium nitrate, magnesium acetate, cuprous copper, etc. in any proportion; the metal catalyst in the above embodiment may be replaced by palladium and nickel, nickel and ruthenium, and copper and nickel mixed or supported catalysts in any ratio, palladium/activated carbon (palladium content 3 wt.%), ruthenium/activated carbon (ruthenium content 4 wt.%), platinum/silica (platinum content 0.1 wt.%), and platinum/zirconia (platinum content 10 wt.%).
The chemical shift of carbonyl carbon is between 170-210ppm, the chemical shift of unsaturated carbon of carbon-carbon double bond is between 100-150ppm, and then according to the peak-appearing reference range of different carbon atoms and hydrogen atoms such as methyl, methylene, etc., and according to the peak-appearing positions of H spectrum and C spectrum shown in figures 1 and 2, the structures of C12 and C18 compounds synthesized by methyl isobutyl ketone aldol condensation are respectively as follows:
Figure GDA0002059700890000091
although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (9)

1. A method for synthesizing aviation fuel oil by methyl isobutyl ketone aldol condensation, the aviation fuel oil synthesized by methyl isobutyl ketone aldol condensation mainly comprises C12, C18 long-chain alkane, the branch chain is many, the freezing point is in the range of (-40) - (-58) DEG C, and the method is characterized in that: the method comprises the following steps:
dispersing a metal salt catalyst in methyl isobutyl ketone, placing the methyl isobutyl ketone in a reaction kettle, heating for aldol condensation reaction, cooling to room temperature after the reaction is finished, taking out reaction liquid, standing for layering, taking out supernatant, placing the supernatant in the reaction kettle, introducing hydrogen, adding the metal catalyst into a reaction system, and carrying out hydrogenation reaction under the catalysis of the metal catalyst to obtain a product, namely the aviation fuel oil;
the preferable cation of the metal salt catalyst is Na+、Mg2+、Al3+、Cu2+、Cu+、Fe3+、Zn2+、Ca2+One or a mixture of more than two of halide, sulfate, nitrate and acetate in any proportion.
2. The method for synthesizing aviation fuel oil by the aldol condensation of methyl isobutyl ketone according to claim 1, which is characterized in that: the metal catalyst selected is preferably a noble metal catalyst comprising: one or more of platinum, palladium and ruthenium.
3. The method for synthesizing aviation fuel oil by the aldol condensation of methyl isobutyl ketone according to claim 1, which is characterized in that: the selected metal catalyst is a supported catalyst, and the carrier of the supported catalyst is one or a mixture of more than two of active carbon, alumina, silica and zirconia; the metal active component of the supported catalyst is one or more than two of platinum, palladium and ruthenium; the content of the metal active component in the supported catalyst is 0.1-10%.
4. A method for synthesizing aviation fuel oil by aldol condensation of methyl isobutyl ketone according to claim 1, 2 or 3, characterized in that: the mass ratio of the metal salt catalyst to the methyl isobutyl ketone is 1: 1-200.
5. The method for synthesizing aviation fuel oil by aldol condensation of methyl isobutyl ketone according to claim 4, wherein: the temperature of the aldol condensation reaction is 180-300 ℃.
6. The method for synthesizing aviation fuel oil by aldol condensation of methyl isobutyl ketone according to claim 5, wherein: the time of the aldol condensation reaction is 2-20 h.
7. The method for synthesizing aviation fuel oil by aldol condensation of methyl isobutyl ketone according to claim 6, wherein: the addition amount of the metal catalyst is 0.01-0.1 time of the mass of the supernatant liquid.
8. The method for synthesizing aviation fuel oil by aldol condensation of methyl isobutyl ketone according to claim 7, wherein: and introducing hydrogen to ensure that the pressure in the reaction kettle is 0.1-2 MPa.
9. The method for synthesizing aviation fuel oil by aldol condensation of methyl isobutyl ketone according to claim 8, wherein: the reaction temperature of the hydrogenation reaction is 100-300 ℃, and the reaction time is 2-20 h.
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