CN108191599B - Four-membered ring fuel molecule and photochemical preparation method thereof - Google Patents

Four-membered ring fuel molecule and photochemical preparation method thereof Download PDF

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CN108191599B
CN108191599B CN201810008691.8A CN201810008691A CN108191599B CN 108191599 B CN108191599 B CN 108191599B CN 201810008691 A CN201810008691 A CN 201810008691A CN 108191599 B CN108191599 B CN 108191599B
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cyclohexenone
cyclopentenone
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diethyl
dimethyl
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CN108191599A (en
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邹吉军
谢君健
潘伦
张香文
王莅
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Tianjin University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column

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Abstract

The invention discloses a fuel molecule with a quaternary ring structure, which has the following structure:
Figure DDA0001539533770000011
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3. The invention also discloses a photochemical preparation method of the fuel molecule with the quaternary ring structure. The fuel molecule with the high-tension quaternary ring structure has excellent performances of high density, high heat value and low freezing point; the preparation method has high yield, does not need solvent and has mild reaction conditions.

Description

Four-membered ring fuel molecule and photochemical preparation method thereof
Technical Field
The invention belongs to the field of liquid fuel propellants, and relates to a high-tension four-membered ring fuel molecule and a photochemical preparation method thereof.
Background
The fuel is the blood of all engines, and the normal operation of the engines is ensured. For aerospace vehicles such as airplanes, missiles, rockets, etc., which have limited volumes, high density fuels with higher density and higher calorific value are required. When the volume of the aircraft is fixed, the greater the density of the fuel, the greater the mass of fuel carried by the aircraft; the higher the calorific value of the fuel, the greater the energy released per unit volume of fuel consumed, the more advantageous it is to improve the performance of the aircraft (including range, speed and payload); or on the premise of keeping the performance ratio of the aircraft unchanged, the volume of the oil tank is reduced, and the small aircraft is developed to improve the penetration capability and the flexibility and the maneuverability of the aircraft to a greater extent.
The high-density fuel refers to artificially synthesized fuel with density more than 0.8g/cm3The liquid hydrocarbon fuel of (2) is a single component or a mixture of a plurality of hydrocarbons. The synthesis of high density hydrocarbon fuels is divided into direct synthesis of high density, low freezing point, high calorific value polycyclic hydrocarbons and addition of energetic additives to the hydrocarbons. A large amount of experimental data show that the density of the hydrocarbon fuel can be improved by the multi-ring structure; the intramolecular ring tension can increase the mass thermal value of the fuel. According to the literature, the dicyclopentane can be obtained with high selectivity by catalyzing condensation and hydrodeoxygenation of cyclopentanone aldol by using MOF-coated phosphotungstic acid in Green Chemistry, 2015, 17 and 4473, and the density of the dicyclopentane is 0.867g/cm3(ii) a Literature Scientific Reports, 2015, 5, 9565 use cyclopentanol as raw material and undergo Guerbet reaction and hydrodeoxygenation to obtain a density of 0.91g/cm3Is a tricyclopentane. Although a large number of fuel molecules of the polycyclic alkane type are reported, there are few reports of fuel molecules having a high-tensile four-membered ring structure. In addition to density and heating value, freeze point and low temperature viscosity are important indicators of fuel. Generally, as the density increases, the freezing point and low temperature viscosity of the hydrocarbon fuel also increases. It is therefore a great challenge to synthesize high density fuels with high density, high heat value and excellent low temperature properties.
Disclosure of Invention
The invention aims to provide a fuel molecule with a high-tension four-membered ring structure, a photochemical preparation process of the fuel molecule is developed, and the synthesized fuel molecule has excellent properties of high density, high heat value and low freezing point.
A first aspect of the invention relates to a four-membered ring fuel molecule having the structure:
Figure BDA0001539533760000021
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3。
Preferably, when n is 1, the density of the fuel molecules is 0.88-0.95 g/cm3The freezing point is not higher than-55 ℃, and the mass heat value is not lower than 42.5 MJ/kg; when n is 2, the density of the fuel molecules is 0.89-0.97 g/cm3The freezing point is not higher than-40 ℃, and the mass heat value is not lower than 42.7 MJ/kg.
The second aspect of the invention relates to a preparation method of the four-membered ring fuel molecule, and the first technical scheme is that the preparation method comprises the following steps: in the presence of photosensitizer, substituted cyclic olefin ketone undergoes cycloaddition reaction to obtain fuel parent molecule, then the fuel parent molecule is hydrodeoxygenated to obtain the described four-membered ring fuel molecule,
Figure BDA0001539533760000022
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3。
The second technical solution of the second aspect of the present invention is that the method includes the following steps: in the presence of photosensitizer, substituted cycloolefine ketone and substituted cycloolefine produce cycloaddition reaction to obtain fuel parent molecule, then make the fuel parent molecule undergo the process of hydrodeoxygenation to obtain the described four-membered ring fuel molecule,
Figure BDA0001539533760000023
Figure BDA0001539533760000031
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3。
The third technical solution of the second aspect of the present invention is that the method includes the following steps: in the presence of photosensitizer, substituted cycloolefine can produce ring addition reaction to obtain the described four-membered ring fuel molecule,
Figure BDA0001539533760000032
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3。
Preferably, the photosensitizer is one or more of cyclopentanone, cyclohexanone, acetone, benzophenone, acetophenone, michael ketone, tetraethylmichael ketone and N-methylpyrrolidone, and the adding amount of the photosensitizer is 1 wt% -10 wt% of the reactants.
Preferably, the substituted cycloalkenone is cyclopentenone, 3-methyl-2-cyclopentenone, 4-methyl-2-cyclopentenone, 5-methyl-2-cyclopentenone, 4,4 '-dimethyl-2-cyclopentenone, 3, 4-dimethyl-2-cyclopentenone, 3, 5-dimethyl-2-cyclopentenone, 4, 5-dimethyl-2-cyclopentenone, 3,4, 4' -trimethyl-2-cyclopentenone, 3,4, 5-trimethyl-2-cyclopentenone, 3-ethyl-2-cyclopentenone, 4-ethyl-2-cyclopentenone, 5-methyl-2-cyclopentenone, 4-methyl-2-cyclopentenone, 3,4, 5-methyl-2-cyclopentenone, or mixtures thereof, 4,4 '-diethyl-2-cyclopentenone, 3, 4-diethyl-2-cyclopentenone, 3, 5-diethyl-2-cyclopentenone, 4, 5-diethyl-2-cyclopentenone, 3,4, 4' -triethyl-2-cyclopentenone, 3,4, 5-triethyl-2-cyclopentenone, cyclohexenone, 2-methyl-2-cyclohexenone, 3-methyl-2-cyclohexenone, 4-methyl-2-cyclohexenone, 5-methyl-2-cyclohexenone, 6-methyl-2-cyclohexenone, 2, 3-dimethyl-2-cyclohexenone, 2, 4-diethyl-2-cyclohexenone, 3, 5-diethyl-2-cyclopentenone, 3, 5-triethyl-2-cyclopentenone, 2-methyl-2-cyclohexenone, 2-dimethyl-2-cyclohexenone, 2-methyl-, 2, 5-dimethyl-2-cyclohexenone, 2, 6-dimethyl-2-cyclohexenone, 3, 4-dimethyl-2-cyclohexenone, 3, 5-dimethyl-2-cyclohexenone, 3, 6-dimethyl-2-cyclohexenone, 4, 5-dimethyl-2-cyclohexenone, 4, 6-dimethyl-2-cyclohexenone, 5, 6-dimethyl-2-cyclohexenone, 2-ethyl-2-cyclohexenone, 3-ethyl-2-cyclohexenone, 4-ethyl-2-cyclohexenone, 5-ethyl-2-cyclohexenone, 6-ethyl-2-cyclohexenone, 4-ethyl-2-cyclohexenone, 5-ethyl-2-cyclohexenone, 2-ethyl-2-cyclohexenone, and mixtures thereof, 2, 3-diethyl-2-cyclohexenone, 2, 4-diethyl-2-cyclohexenone, 2, 5-diethyl-2-cyclohexenone, 2, 6-diethyl-2-cyclohexenone, 3, 4-diethyl-2-cyclohexenone, 3, 5-diethyl-2-cyclohexenone, 3, 6-diethyl-2-cyclohexenone, 4, 5-diethyl-2-cyclohexenone, 4, 6-diethyl-2-cyclohexenone, 5, 6-diethyl-2-cyclohexenone, 2,3, 4-trimethyl-2-cyclohexenone, 2,3, 5-trimethyl-2-cyclohexenone, 2, one or more of 3, 6-trimethyl-2-cyclohexenone, 3,4, 5-trimethyl-2-cyclohexenone, 3,4, 6-trimethyl-2-cyclohexenone, and 4,5, 6-trimethyl-2-cyclohexenone.
Preferably, the substituted cycloalkene is cyclopentene, methylcyclopentene, 3-methylcyclopentene, 4-methylcyclopentene, 1, 2-dimethylcyclopentene, 1, 3-dimethylcyclopentene, 1, 4-dimethylcyclopentene, ethylcyclopentene, 3-ethylcyclopentene, 4-ethylcyclopentene, 1, 2-diethylcyclopentene, 1, 3-diethylcyclopentene, 1, 4-diethylcyclopentene, cyclohexene, methylcyclohexene, 3-methylcyclohexene, 4-methylcyclohexene, 1, 2-dimethylcyclohexene, 1, 3-dimethylcyclohexene, 1, 4-dimethylcyclohexene, ethylcyclohexene, 3-ethylcyclohexene, 4-ethylcyclohexene, 1, 2-diethylcyclohexene, 1, 3-diethylcyclohexene, One or more of 1, 4-diethylcyclohexene.
Preferably, the cycloaddition reaction conditions are as follows: under the irradiation of a high-pressure mercury lamp, the reaction is carried out for 1 to 24 hours at the temperature of between 40 ℃ below zero and 50 ℃.
Preferably, the reaction conditions of the fuel parent molecule hydrodeoxygenation are that the reaction temperature is 100-200 ℃, the hydrogen pressure is 3-8 MPa, and the reaction time is 10-48H in the presence of a catalyst, wherein the catalyst is a supported catalyst with nickel, platinum or palladium supported on HZSM-5, H β or HY, or a mixture of physically mixed Pd/C and molecular sieves.
A third aspect of the invention relates to the use of said fuel molecule of quaternary ring structure for high density aerospace fuel.
The invention has the beneficial effects that: (1) the fuel molecule with the high-tension quaternary ring structure has excellent performances of high density, high heat value and low freezing point, so that the volume heat value of the fuel molecule is higher than that of common liquid hydrocarbon fuel, and for an aerospace vehicle with a certain oil tank volume, the fuel molecule can effectively improve the oil carrying quality and meet the application requirements of long range, high navigational speed and large load. (2) The fuel molecule with the high-tension quaternary ring structure can be prepared by photochemical cycloaddition and hydrodeoxygenation at normal temperature and normal pressure, the preparation method is high in yield, does not need a solvent, is mild in reaction conditions, has good universality for various substituted cycloalkenone and substituted cycloalkene, and has high industrial application value.
Drawings
None.
Detailed Description
The present invention is further illustrated by the following examples in the table, which are intended to be illustrative only and not limiting.
Table 1 shows examples of the molecular synthesis reaction of fuel precursors.
TABLE 1 Fuel parent molecular Synthesis reaction
Figure BDA0001539533760000051
Figure BDA0001539533760000061
The specific reaction steps are as examples 13 and 17 in Table 1. the specific steps are that 10g of cyclopentenone and 10g of cyclohexene (or 10g of cyclohexenone and 10g of cyclohexene), 1% of acetone by mass fraction are added into a single-port jacketed glass reactor of 25m L, nitrogen is bubbled for 0.5h under stirring, then the sealed reaction vessel is sealed, condensed water is opened, a high-pressure mercury lamp is irradiated for 5h, the reaction solution is analyzed by gas chromatography-mass spectrometry, the product is determined and the reaction yield is calculated.
Table 2 is an example of a molecular hydrodeoxygenation reaction of a fuel precursor.
TABLE 2 Fuel parent molecule hydrodeoxygenation reaction
Figure BDA0001539533760000071
Fuel parent molecule hydrodeoxygenation step Using example 29 in Table 2, the fuel parent molecule obtained in example 13, 2g Pd/C and 5g H β catalyst were charged into a 100m L autoclave, sealed, and charged with N2Replacing for 3 times, and charging 6MPa of H2And the temperature is increased to 160 ℃ by stirring, and the reaction is carried out for 24 hours. And (3) analyzing the reaction liquid by adopting gas chromatography-mass spectrometry, and qualitatively determining a product and calculating the reaction yield. The fuel parent molecules were completely converted and the yield of target molecules (fuel molecules) was 90%.
From the above, it is known that substituted cycloalkenones and substituted cycloalkenes can give fuel molecules having a high-tensile four-membered ring structure in high yield by photochemical cycloaddition and solvent-free hydrodeoxygenation. Fuel molecules prepared by hydrodeoxygenation of the fuel parent molecule synthesized in example 17 from example 28 were measured to have a density of 0.90g/cm3The freezing point is-55 ℃, and the mass heat value is 42.5 MJ/kg; example 7 Fuel molecules synthesized by hydrodeoxygenation of Fuel parent molecules from example 38, having a density of 0.89g/cm3The freezing point is-40 ℃, and the mass heat value is 42.7 MJ/kg. Comparing the two fuels, the density and low-temperature properties of the fuel molecules with methyl substitution on the ring are reduced to a certain extent, and the finding has a certain guiding significance for the design and synthesis of the fuel molecules in the future.
Figure BDA0001539533760000081

Claims (8)

1. A method of making a four-membered ring fuel molecule, said four-membered ring fuel molecule having the structure:
Figure FDA0002469996540000011
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3(ii) a When n is 1, the density of the fuel molecules is 0.88-0.95 g/cm3The freezing point is not higher than-55 ℃, and the mass heat value is not lower than 42.5 MJ/kg; when n is 2, the density of the fuel molecules is 0.89-0.97 g/cm3The freezing point is not higher than-40 ℃, and the mass heat value is not lower than 42.7 MJ/kg; the preparation method of the four-membered ring fuel molecule is characterized by comprising the following steps: in the presence of photosensitizer, substituted cyclic olefin ketone undergoes cycloaddition reaction to obtain fuel parent molecule, then the fuel parent molecule is hydrodeoxygenated to obtain the described four-membered ring fuel molecule,
Figure FDA0002469996540000012
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3。
2. A method of making a four-membered ring fuel molecule, said four-membered ring fuel molecule having the structure:
Figure FDA0002469996540000013
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3(ii) a When n is 1, the density of the fuel molecules is 0.88-0.95 g/cm3The freezing point is not higher than-55 ℃, and the mass heat value is not lower than 42.5 MJ/kg; when n is 2, the density of the fuel molecules is 0.89-0.97 g/cm3Freezing pointThe mass heat value is not lower than 42.7MJ/kg at the temperature of not higher than-40 ℃; the method for preparing the four-membered ring fuel molecule is characterized by comprising the following steps: in the presence of photosensitizer, substituted cycloolefine ketone and substituted cycloolefine produce cycloaddition reaction to obtain fuel parent molecule, then make the fuel parent molecule undergo the process of hydrodeoxygenation to obtain the described four-membered ring fuel molecule,
Figure FDA0002469996540000021
wherein n is 1 or 2, R1、R2、R3、R4、R5、R6Each independently is H or-CH3or-CH2CH3。
3. The preparation method according to claim 1 or 2, wherein the photosensitizer is one or more of cyclopentanone, cyclohexanone, acetone, benzophenone, acetophenone, michelson, tetraethylmichelson, and N-methylpyrrolidone, and the photosensitizer is added in an amount of 1-10 wt% of the reactants.
4. The process according to claim 1 or 2, wherein the substituted cycloalkenone is 2-cyclopentenone, 3-methyl-2-cyclopentenone, 4-methyl-2-cyclopentenone, 5-methyl-2-cyclopentenone, 4,4 '-dimethyl-2-cyclopentenone, 3, 4-dimethyl-2-cyclopentenone, 3, 5-dimethyl-2-cyclopentenone, 4, 5-dimethyl-2-cyclopentenone, 3,4, 4' -trimethyl-2-cyclopentenone, 3,4, 5-trimethyl-2-cyclopentenone, 3-ethyl-2-cyclopentenone, 4-methyl-2-cyclopentenone, 5-ethyl-2-cyclopentenone, 4,4 ' -diethyl-2-cyclopentenone, 3, 4-diethyl-2-cyclopentenone, 3, 5-diethyl-2-cyclopentenone, 4, 5-diethyl-2-cyclopentenone, 3,4,4 ' -triethyl-2-cyclopentenone, 3,4, 5-triethyl-2-cyclopentenone, 2-cyclohexenone, 2-methyl-2-cyclohexenone, 3-methyl-2-cyclohexenone, 4-methyl-2-cyclohexenone, 5-methyl-2-cyclohexenone, 6-methyl-2-cyclohexenone, 2, 3-dimethyl-2-cyclohexenone, 2, 3-diethyl-2-cyclohexenone, 3,4 ' -triethyl-2-cyclopentenone, 2-methyl-2-cyclohexenone, 2-methyl-cyclohexenone, 2, 4-dimethyl-2-cyclohexenone, 2, 5-dimethyl-2-cyclohexenone, 2, 6-dimethyl-2-cyclohexenone, 3, 4-dimethyl-2-cyclohexenone, 3, 5-dimethyl-2-cyclohexenone, 3, 6-dimethyl-2-cyclohexenone, 4, 5-dimethyl-2-cyclohexenone, 4, 6-dimethyl-2-cyclohexenone, 5, 6-dimethyl-2-cyclohexenone, 2-ethyl-2-cyclohexenone, 3-ethyl-2-cyclohexenone, 4-ethyl-2-cyclohexenone, 5-ethyl-2-cyclohexenone, 2-methyl-2-cyclohexenone, 2-ethyl-2-cyclohexenone, 2-methyl-ethyl-2-cyclohexenone, 2, 6-ethyl-2-cyclohexenone, 2, 3-diethyl-2-cyclohexenone, 2, 4-diethyl-2-cyclohexenone, 2, 5-diethyl-2-cyclohexenone, 2, 6-diethyl-2-cyclohexenone, 3, 4-diethyl-2-cyclohexenone, 3, 5-diethyl-2-cyclohexenone, 3, 6-diethyl-2-cyclohexenone, 4, 5-diethyl-2-cyclohexenone, 4, 6-diethyl-2-cyclohexenone, 5, 6-diethyl-2-cyclohexenone, 2,3, 4-trimethyl-2-cyclohexenone, 2,3, 5-trimethyl-2-cyclohexenone, a salt thereof, and a pharmaceutically acceptable carrier, 2,3, 6-trimethyl-2-cyclohexenone, 3,4, 5-trimethyl-2-cyclohexenone, 3,4, 6-trimethyl-2-cyclohexenone, and 4,5, 6-trimethyl-2-cyclohexenone.
5. The process according to claim 1 or 2, wherein the substituted cycloalkene is cyclopentene, 1-methylcyclopentene, 3-methylcyclopentene, 4-methylcyclopentene, 1, 2-dimethylcyclopentene, 1, 3-dimethylcyclopentene, 1, 4-dimethylcyclopentene, 1-ethylcyclopentene, 3-ethylcyclopentene, 4-ethylcyclopentene, 1, 2-diethylcyclopentene, 1, 3-diethylcyclopentene, 1, 4-diethylcyclopentene, cyclohexene, 1-methylcyclohexene, 3-methylcyclohexene, 4-methylcyclohexene, 1, 2-dimethylcyclohexene, 1, 3-dimethylcyclohexene, 1, 4-dimethylcyclohexene, 1-ethylcyclohexene, or a mixture thereof, One or more of 3-ethyl cyclohexene, 4-ethyl cyclohexene, 1, 2-diethyl cyclohexene, 1, 3-diethyl cyclohexene and 1, 4-diethyl cyclohexene.
6. The process according to claim 1 or 2, wherein the cycloaddition reaction is carried out under the following conditions: under the irradiation of a high-pressure mercury lamp, the reaction is carried out for 1 to 24 hours at the temperature of between 40 ℃ below zero and 50 ℃.
7. The preparation method of the fuel precursor of the fuel of the claim 1 or 2, wherein the reaction conditions of the molecular hydrodeoxygenation of the fuel precursor are that the reaction temperature is 100-200 ℃, the hydrogen pressure is 3-8 MPa, and the reaction time is 10-48H in the presence of a catalyst, wherein the catalyst is a supported catalyst of nickel, platinum or palladium supported on HZSM-5, H β or HY, or a mixture of Pd/C and molecular sieve after physical mixing.
8. Use of the fuel molecule of quaternary ring structure of claim 1 for aerospace fuel.
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