Condensed ring sustainable aviation fuel precursor and preparation method thereof, and condensed ring sustainable aviation fuel and preparation method thereof

Abstract

The invention provides a fused ring sustainable aviation fuel precursor and a preparation method thereof, and a fused ring sustainable aviation fuel and a preparation method thereof. The fused ring sustainable aviation fuel precursor can be used for preparing the fused ring sustainable aviation fuel, and the fused ring sustainable aviation fuel can be synthesized through two steps of normal-temperature normal-pressure photocatalytic cycloaddition and hydrodeoxygenation. The preparation method of the fuel is high in yield, mild in reaction condition, simple in reaction process, few in by-products and low in product separation and purification cost. Tests show that the prepared condensed ring sustainable aviation fuel has the characteristics of high density, high calorific value and low freezing point, the density can be up to 0.873 g / mL, the combustion calorific value can be up to 41.7 MJ / kg, and the freezing point can be as low as-75.0 DEG C. The condensed ring sustainable aviation fuel can be used as an additive or substitute of aviation fuel, and can promote high-valued utilization of biomass resources and achieve the targets of carbon peak reaching and carbon neutralization.

Description

Technical Field

[0001] The present invention belongs to the technical field of fuel preparation, and in particular relates to a condensed-ring sustainable aviation fuel precursor and a preparation method thereof, a condensed-ring sustainable aviation fuel and a preparation method thereof. Background Art

[0002] Sustainable aviation fuel refers to clean fuel that is manufactured from clean raw materials, achieves emission reductions, and can be directly applied to traditional aircraft engines. At present, the raw material sources of sustainable aviation fuel include waste oils and fats, urban waste, agricultural and forestry waste, energy crops, and renewable electricity. Compared with fossil-based aviation fuel, sustainable aviation fuel can reduce carbon dioxide emissions by more than 80% over its entire life cycle. Therefore, the development of sustainable aviation fuel is of great significance to promoting the development of my country's aerospace industry and national defense construction, promoting the high-value utilization of biomass resources, and achieving the goals of "carbon peak" and "carbon neutrality".

[0003] Sustainable aviation fuel is generally prepared by hydrodeoxygenating a sustainable aviation fuel precursor. It can be seen that the sustainable aviation fuel precursor has a great influence on the performance of sustainable aviation fuel. However, the density and volume net calorific value of the aviation fuel currently obtained are still relatively low, which cannot meet the application of new high-performance aerospace vehicles. Therefore, the development and preparation of a sustainable aviation fuel precursor to improve the performance of the fuel is still an urgent problem to be solved. Summary of the invention

[0004] In view of this, the purpose of the present invention is to provide a condensed-ring sustainable aviation fuel precursor and a preparation method thereof, a condensed-ring sustainable aviation fuel and a preparation method thereof. The present invention uses the condensed-ring sustainable aviation fuel precursor to prepare a condensed-ring sustainable aviation fuel with high density and high volume net calorific value.

[0005] To achieve this object, the present invention adopts the following technical solutions:

[0006] In a first aspect, the present invention provides a condensed-ring sustainable aviation fuel precursor as shown in Formula I:

[0007]

[0008] Wherein, R1 is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl or hydrogen;

[0009] R2-R5 are independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl;

[0010] or

[0011] R2 forms a ring with R3 and the carbon atom where they are located, R2 forms a ring with R4 and the carbon atom where they are located, and R4 forms a ring with R5 and the carbon atom where they are located.

[0012] Preferably, R1 is selected from substituted or unsubstituted C1-C3 alkyl, substituted or unsubstituted C6-C15 aryl or hydrogen;

[0013] R2-R5 are independently selected from hydrogen, substituted or unsubstituted C1-C3 alkyl;

[0014] or

[0015] R2 forms a ring with R3 and the carbon atom where they are located, R2 forms a ring with R4 and the carbon atom where they are located, and R4 forms a ring with R5 and the carbon atom where they are located.

[0016] Preferably, the condensed-ring sustainable aviation fuel precursor is selected from any one of the following formulas 1 to 16:

[0017]

[0018] In a second aspect, the present invention provides a method for preparing the above-mentioned condensed-ring sustainable aviation fuel precursor, comprising the following steps:

[0019] In the presence of light and a catalyst, the compound represented by formula A and the compound represented by formula B are copolymerized in a solvent to obtain the condensed-ring sustainable aviation fuel precursor;

[0020]

[0021] Preferably, the catalyst is selected from acetic acid.

[0022] Preferably, the solvent includes any one or more of acetonitrile, methanol, ethanol, water, toluene, ethyl acetate, acetone or dichloromethane.

[0023] Preferably, the molar ratio of the compound represented by formula A to the compound represented by formula B is (1-4):1.

[0024] Preferably, the amount of the catalyst is 0 to 10% of the amount of the compound represented by formula B.

[0025] Preferably, the concentration of the compound represented by formula B is 0.05 to 0.8 mol / L.

[0026] Preferably, the reaction temperature is -20 to 40°C and the reaction time is 1 to 24 hours.

[0027] Preferably, before the reaction is carried out, an inert gas is introduced into the system for 0.5 to 2 h.

[0028] In a third aspect, the present invention provides a condensed-ring sustainable aviation fuel, which is prepared using the condensed-ring sustainable aviation fuel precursor.

[0029] Preferably, the structural formula of the condensed-ring sustainable aviation fuel includes at least one of the formulas (1) to (10):

[0030]

[0031] In the present invention, the condensed-ring sustainable aviation fuel is a mixture of formula (1) to formula (10), rather than a specific fuel obtained from a specific precursor.

[0032] In a fourth aspect, the present invention further provides a method for preparing the above-mentioned condensed-ring sustainable aviation fuel, comprising the following steps:

[0033] In a hydrogen atmosphere, subjecting the condensed-ring sustainable aviation fuel precursor to a hydrodeoxygenation reaction in the presence of a catalyst to obtain the condensed-ring sustainable aviation fuel;

[0034] The catalyst is a combination of an activated carbon-supported noble metal hydrogenation catalyst and a molecular sieve, or a combination of an activated carbon-supported noble metal hydrogenation catalyst and a heteropoly acid.

[0035] Preferably, the activated carbon-supported noble metal hydrogenation catalyst comprises any one or more of Pd / C, Rh / C, Pt / C or Ru / C.

[0036] Preferably, the molecular sieve includes any one or more of HY molecular sieve, LaY molecular sieve, CeY molecular sieve, NaY molecular sieve, ReY molecular sieve, NH4Y molecular sieve, USY molecular sieve, mesoporous Y molecular sieve, ZSM-molecular sieve, ZSM-35 molecular sieve, MCM-22 molecular sieve, MCM-41 molecular sieve, β molecular sieve or SAPO molecular sieve.

[0037] Preferably, the heteropolyacid includes any one or more of trifluoromethanesulfonate, silicotungstic acid, phosphotungstic acid or phosphomolybdic acid.

[0038] Preferably, the pressure of the hydrogen is 0.5-8 MPa.

[0039] Preferably, the hydrodeoxygenation reaction time is 1 to 18 hours and the temperature is 100 to 250°C.

[0040] Compared with the prior art, the present invention has the following beneficial effects:

[0041] The present invention provides a condensed ring sustainable aviation fuel precursor, which has a multi-branched condensed ring structure, and the structure has the advantages of high density, high calorific value, low freezing point, etc. In addition, the preparation method of the condensed ring sustainable aviation fuel precursor is simple, does not require a catalyst, and is easy to achieve industrial or industrial production.

[0042] The present invention uses the condensed ring sustainable aviation fuel precursor to prepare condensed ring sustainable aviation fuel, which can be synthesized in two steps of photocatalytic cycloaddition and hydrodeoxygenation at room temperature and pressure. The preparation method of the fuel involved in the present invention has high yield, mild reaction conditions, simple reaction process, few by-products, and low cost for product separation and purification.

[0043] After testing, the prepared concentrated-ring sustainable aviation fuel has the characteristics of high density, high calorific value and low freezing point. The density can be as high as 0.873g / mL, the combustion calorific value can be as high as 41.7MJ / kg, and the freezing point can be as low as -75.0℃. It can be used as an additive or substitute for aviation fuel, promoting the high-value utilization of biomass resources and achieving the "carbon peak" and "carbon neutrality" goals. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] Figure 1 is a gas chromatogram of the fuel precursor (copolymerization product of cyclohexene and angelica lactone) in Example 1;

[0045] Figure 2 is the mass spectrum of the fuel precursor (copolymerization product of cyclohexene and angelica lactone) in Example 1;

[0046] Figure 3 This is the hydrogen nuclear magnetic resonance spectrum of the fuel precursor (copolymerization product of cyclohexene and angelica lactone) in Example 1;

[0047] Figure 4 The carbon NMR spectrum of the fuel precursor (copolymerization product of cyclohexene and angelica lactone) in Example 1;

[0048] Figure 5 for Figure 1 a gas chromatogram of a hydrodeoxygenated fuel product corresponding to a fuel precursor;

[0049] Figure 6 for Figure 1 a proton nuclear magnetic resonance spectrum of a fuel product corresponding to the hydrodeoxygenation of the fuel precursor;

[0050] Figure 7 for Figure 1 a carbon NMR spectrum of a fuel product corresponding to the hydrodeoxygenation of the fuel precursor;

[0051] Figure 8 is the hydrogen nuclear magnetic resonance spectrum of the fuel precursor (copolymerization product of cyclohexene and 2-(5H)-furanone) in Example 3;

[0052] Fig. 9 The carbon NMR spectrum of the fuel precursor (copolymerization product of cyclohexene and 2-(5H)-furanone) in Example 3;

[0053] Fig.10is the mass spectrum of the fuel precursor (copolymerization product of cyclohexene and 2-(5H)-furanone) in Example 3;

[0054] Figures 11 to 20 They are respectively the mass spectra of the structural formulas (1) to (10) of the condensed-ring sustainable aviation fuel and the mass spectra of the standard substances. DETAILED DESCRIPTION

[0055] The technical solution of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0056] In view of the problem that the density and volumetric net calorific value of aviation fuel obtained by the prior art are still low, the present invention provides a condensed-ring sustainable aviation fuel precursor as shown in Formula I:

[0057]

[0058] Wherein, R1 is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl or hydrogen;

[0059] R2-R5 are independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl;

[0060] or

[0061] R2 forms a ring with R3 and the carbon atom where they are located, R2 forms a ring with R4 and the carbon atom where they are located, and R4 forms a ring with R5 and the carbon atom where they are located.

[0062] In some embodiments of the present invention, the structural formula of the fused-ring sustainable aviation fuel precursor is as shown in Formula I, wherein R1 is selected from substituted or unsubstituted C1-C3 alkyl, substituted or unsubstituted C6-C15 aryl or hydrogen;

[0063] R2-R5 are independently selected from hydrogen, substituted or unsubstituted C1-C3 alkyl;

[0064] or

[0065] R2 forms a ring with R3 and the carbon atom where they are located, R2 forms a ring with R4 and the carbon atom where they are located, and R4 forms a ring with R5 and the carbon atom where they are located.

[0066] The number of carbon atoms in the ring is any integer from 5 to 15, and specifically can be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15.

[0067] In some specific embodiments of the present invention, the condensed ring sustainable aviation fuel precursor is selected from the following

[0068] Any one of Formula 1 to Formula 16:

[0069]

[0070] The condensed-ring sustainable aviation fuel precursor provided by the present invention has a multi-branched condensed-ring structure, which has the advantages of high density, high calorific value and low freezing point.

[0071] The present invention also provides a method for preparing the above-mentioned condensed-ring sustainable aviation fuel precursor, comprising the following steps:

[0072] In the presence of light and a catalyst, the compound represented by formula A and the compound represented by formula B are copolymerized in a solvent to obtain the condensed-ring sustainable aviation fuel precursor;

[0073]

[0074] In the present invention, the light is ultraviolet light, and the irradiation condition of the ultraviolet light can be provided by a 185-254nm LED light strip. In some specific embodiments of the present invention, a 185-254nm LED light strip is used to irradiate the compound represented by formula A and the compound represented by formula B, so that a 2+2 reaction occurs in a solvent in the presence of a catalyst.

[0075] In the present invention, the compound represented by formula A is generally selected from biomass-derived olefins such as cyclohexene, pinene, norbornene or limonene, preferably cyclohexene; the compound represented by formula B is generally selected from α, β-unsaturated lactone compounds, preferably β-angelica lactone or 2-(5H)-furanone. In some embodiments of the present invention, the molar ratio of the compound represented by formula A to the compound represented by formula B is 1: (1 to 4), for example, it can be 1: 1, 1: 2, 1: 3 or 1: 4. Thus, the ratio of the compound represented by formula A to the compound represented by formula B is appropriate, and a condensed-ring sustainable aviation fuel precursor can be efficiently obtained.

[0076] In the present invention, the copolymerization reaction yield is high, and almost no by-products are generated in the reaction. Wherein, the catalyst is preferably selected from acetic acid, which can be prepared in large quantities through a biomass route, and has the advantages of strong environmental friendliness, low price, and easy separation. In the present invention, the amount of the catalyst is 0 to 10% of the amount of the compound represented by formula B, preferably 5%.

[0077] In the present invention, the solvent includes any one or more of acetonitrile, methanol, ethanol, water, toluene, ethyl acetate, acetone or dichloromethane. Thus, the source is wide, the price is low, and it is not easy to react with the reactants, and no new by-products are introduced. The present invention has no particular restrictions on the amount of the solvent. Generally, the concentration of the compound shown in the control formula B is 0.05 to 0.8 mol / L, preferably 0.1 to 0.5 mol / L.

[0078] It should be noted that in the present invention, before the copolymerization reaction is carried out, an inert gas is generally introduced into the mixture formed by the catalyst, the compound represented by formula A, the compound represented by formula B and the solvent for 0.5 to 2 hours, preferably 1 to 1.5 hours, in order to effectively remove oxygen in the reaction system and reduce the occurrence of side reactions. The present invention has no particular limitation on the inert gas, and it can be an atmosphere well known to those skilled in the art, such as nitrogen.

[0079] In the present invention, the copolymerization reaction temperature is -20 to 40°C, for example, -20°C, -10°C, 0°C, 10°C, 20°C, 30°C or 40°C, etc.; the reaction time is 1 to 24 hours, for example, 1 hour, 2 hours, 4 hours, 6 hours, 8 hours, 10 hours, 12 hours, 14 hours, 16 hours, 18 hours, 20 hours, 22 hours or 24 hours, etc. Thus, the reaction process is simple and the reaction conditions are mild.

[0080] As described above, in some embodiments of the present invention, the α,β-unsaturated lactone compound includes β-angelica lactone and / or 2-(5H)-furanone, and the biomass-derived olefin is preferably cyclohexene.

[0081] In some specific embodiments of the present invention, the molecular formula of cyclohexene is The molecular formula of β-angelica lactone is The above copolymerization reaction is a [2+2] cycloaddition reaction between two reactant molecules, and the specific reaction formula is:

[0082]

[0083] Thus, the condensed-ring sustainable aviation fuel molecular precursor can be obtained in high yield through a one-step cycloaddition.

[0084] In other specific embodiments of the present invention, the molecular formula of cyclohexene is The molecular formula of 2-(5H)-furanone is The above copolymerization reaction is a [2+2] cycloaddition reaction between two reactant molecules, and the specific reaction formula is:

[0085] Therefore, the condensed-ring sustainable aviation fuel molecular precursor can be obtained in high yield through a one-step cycloaddition.

[0086] In summary, the preparation method of the condensed-ring sustainable aviation fuel precursor is simple, does not require a catalyst, and is easy to achieve industrial or industrial production.

[0087] The present invention also provides a condensed-ring sustainable aviation fuel, which is prepared by using the condensed-ring sustainable aviation fuel precursor.

[0088] In some specific embodiments of the present invention, the structural formula of the condensed-ring sustainable aviation fuel includes at least one of formulas (1) to (10):

[0089]

[0090] In the present invention, the mass spectra of the condensed-ring sustainable aviation fuels represented by the above formulas (1) to (10) are compared with the mass spectra of the standard substances as shown in the following table: Figures 11-12 shown.

[0091] The present invention also provides a method for preparing the above-mentioned condensed-ring sustainable aviation fuel, comprising the following steps:

[0092] In a hydrogen atmosphere, the condensed-ring sustainable aviation fuel precursor is subjected to a hydrodeoxygenation reaction in the presence of a catalyst to obtain the condensed-ring sustainable aviation fuel.

[0093] In the present invention, the hydrodeoxygenation reaction is to reduce the ester group in the condensed-ring sustainable aviation fuel precursor. At the same time, since the ester group is adjacent to the high-strain four-membered ring, the molecule will undergo skeleton rearrangement to a certain extent during the hydrodeoxygenation process to generate a sustainable aviation fuel with a variety of condensed-ring structures.

[0094] In some embodiments of the present invention, the hydrodeoxygenation reaction of the condensed ring sustainable aviation fuel precursor comprises: in a hydrogen atmosphere, the condensed ring sustainable aviation fuel precursor undergoes a hydrodeoxygenation reaction through the combined action of a combination of an activated carbon-supported noble metal hydrogenation catalyst and a molecular sieve or a combination of an activated carbon-supported noble metal hydrogenation catalyst and a heteropoly acid. The hydrogen pressure is 0.5 to 8 MPa, such as 0.5 MPa, 1 MPa, 1.5 MPa, 3 MPa, 5 MPa or 8 MPa, etc.; the hydrodeoxygenation reaction time is 1 to 18 hours, such as 1 hour, 2 hours, 4 hours, 8 hours, 12 hours or 18 hours, etc.; the temperature is 100 to 250°C, such as 100°C, 110°C, 130°C, 180°C or 250°C, etc.

[0095] The above point values ​​are only for enumeration. Other point values ​​within the numerical range are applicable. To avoid complexity, they are not listed here one by one.

[0096] In some specific embodiments of the present invention, in a hydrogen atmosphere, in a solvent of cyclohexane and / or n-hexane, the activated carbon-supported noble metal hydrogenation catalyst and a molecular sieve or a heteropoly acid act together to cause the condensed-ring sustainable aviation fuel precursor to undergo a hydrodeoxygenation reaction. Thus, the activated carbon-supported noble metal hydrogenation catalyst and the molecular sieve or heteropoly acid cooperate with each other to effectively improve the yield of the condensed-ring sustainable aviation fuel.

[0097] In the present invention, the activated carbon-supported noble metal hydrogenation catalyst includes any one or more of Pd / C, Rh / C, Pt / C or Ru / C.

[0098] In the present invention, the molecular sieve includes any one or more of HY molecular sieve, LaY molecular sieve, CeY molecular sieve, NaY molecular sieve, ReY molecular sieve, NH4Y molecular sieve, USY molecular sieve, mesoporous Y molecular sieve, ZSM-5 molecular sieve, ZSM-35 molecular sieve, MCM-22 molecular sieve, MCM-41 molecular sieve, β molecular sieve or SAPO molecular sieve.

[0099] In the present invention, the heteropoly acid includes any one or more of trifluoromethanesulfonate, silicotungstic acid, phosphotungstic acid or phosphomolybdic acid.

[0100] The condensed-ring sustainable aviation fuel of the present invention can be synthesized in two steps through photocatalytic cycloaddition and hydrodeoxygenation at room temperature and pressure. The preparation method of the present invention has high yield, mild reaction conditions, simple reaction process, few by-products, low cost for product separation and purification, and is suitable for large-scale application.

[0101] In order to further illustrate the present invention, the following examples are provided for detailed description. The experimental raw materials used in the following examples of the present invention are all common commercially available products.

[0102] Example 1

[0103] The method for preparing condensed-ring sustainable aviation fuel comprises the following steps:

[0104] Step 1: Preparation of condensed-ring sustainable aviation fuel precursors

[0105] In a 50mL single-mouth quartz glass reaction tube, add 180μL (2mmol) β-angelica lactone and 300μL (3mmol) cyclohexene, then add 10mL chromatographically pure anhydrous acetonitrile, and then add 5mol% acetic acid catalyst (5.7μL), and nitrogen is bubbled for 1h under stirring conditions. Then, connect the condenser and seal it. Turn on the condensed water so that the temperature of the copolymerization reaction is 20°C. Irradiate the reactor with a 185-254nm LED lamp for 8h to obtain a reaction solution. Use gas chromatography-mass spectrometry to analyze the reaction solution, identify the product and calculate the yield of the reaction product. The product yield is 90%. Collect the reaction solution of the parallel multi-tubes into a 500mL rotary evaporator, and use a rotary evaporator to evaporate the solvent to obtain a concentrated solution containing a condensed-ring sustainable aviation fuel precursor. Use gas chromatography to analyze the concentrated solution, and the results are as follows: Figure 1 The concentrated solution was analyzed by mass spectrometry, and the results were as follows Figure 2 The concentrated solution was analyzed by nuclear magnetic resonance spectrometer, and the results were as follows Figure 3 and 4 shown.

[0106] Step 2: Preparation of condensed-ring sustainable aviation fuel using condensed-ring sustainable aviation fuel precursor

[0107] Take 3g of the concentrate in a 500mL hydrogenation kettle, add 100mL of cyclohexane and mix well, add 20wt% Pd / C and 25wt% silicotungstic acid (or other feasible heteropolyacid or molecular sieve catalyst) of the concentrate, mix and seal the hydrogenation kettle, replace it with 3Mpa nitrogen three times, then replace it with 3Mpa hydrogen three times, finally inject 6Mpa hydrogen into the hydrogenation kettle, seal it, start stirring, set the temperature program to heat up to 220℃ at 5℃ / min, and then keep the temperature for 1 hour. 5h, during the hydrogenation period, the pressure gauge is often observed, when the pressure in the hydrogenation kettle drops suddenly, hydrogen is used to replenish the pressure to 6Mpa, samples are taken from the sampling port every 2h and the progress of the hydrogenation reaction is measured by chromatography, when the raw material conversion rate exceeds 90% and the pressure in the hydrogenation kettle no longer changes significantly, the heating is stopped, the hydrogenation kettle is allowed to cool naturally, and the hydrogenation kettle is depressurized after it cools to room temperature, the reaction liquid is taken out, Pd / C and molecular sieves and / or heteropolyacid catalysts are removed by centrifugation, and the solvent is then removed by rotary evaporation, and purified by distillation to obtain a condensed-ring sustainable aviation fuel product.

[0108] It has been calculated that the yield of the hydrodeoxygenation reaction of silicotungstic acid as a heteropolyacid catalyst is 85% (yield = fuel product mass / (amount of fuel precursor substance×theoretical fuel product molecular weight), the theoretical fuel product is a hydrocarbon with the same number of carbon atoms as the fuel precursor and 2 less unsaturations than the fuel precursor).

[0109] The product is analyzed using gas chromatography-mass spectrometry, infrared spectrometer and nuclear magnetic resonance spectrometer to determine the product structure and purity. The gas chromatogram of the fuel product is shown in the figure below. Figure 5As shown, the H NMR spectrum is as Figure 6 As shown, the carbon NMR spectrum is as follows Figure 7 shown.

[0110] Example 2

[0111] Compared with Example 1, the difference is that acetic acid is not added in the copolymerization reaction in step 1, and the other steps and parameters are consistent with those in Example 1.

[0112] In this embodiment, the yield of the condensed-ring sustainable aviation fuel precursor is 78%, and the yield of the condensed-ring sustainable aviation fuel product is 85%.

[0113] Example 3

[0114] Compared with Example 1, the difference is that in step 1, β-angelica lactone is replaced by 2-(5H)-furanone in an equal amount, and the other steps and parameters are consistent with Example 1.

[0115] In this embodiment, the yield of the condensed-ring sustainable aviation fuel precursor is 80%. The yield of the condensed-ring sustainable aviation fuel product is 80%.

[0116] In this embodiment, the nuclear magnetic resonance hydrogen spectrum of the fuel precursor (copolymerization product of cyclohexene and 2-(5H)-furanone) is as follows: Figure 8 As shown, the carbon NMR spectrum of the fuel precursor (copolymerization product of cyclohexene and 2-(5H)-furanone) is as follows Fig. 9 As shown, the mass spectrum of the fuel precursor (copolymerization product of cyclohexene and 2-(5H)-furanone) is as follows Fig.10 shown.

[0117] Performance Testing

[0118] The test method is as follows:

[0119] Density test: GB / T 40401-2021 Skeleton density measurement gas volume displacement method,

[0120] Freezing point test: Weigh 4.04 mg of sample into a crucible, cover the crucible and transfer it to the DSC test instrument, set the program -90~20℃, 5℃ / min heating rate, and collect data in nitrogen atmosphere.

[0121] Calorific value test: refer to GB / T384.

[0122] The test results are shown in Table 1 below:

[0123] Table 1

[0124]

[0125]

[0126] It can be seen from the data in Table 1 that the concentrated-ring sustainable aviation fuel prepared by the present invention has the characteristics of high density, high calorific value and low freezing point. It can be used as an additive or substitute for aviation fuel to promote the high-value utilization of biomass resources and achieve the goals of "carbon peak" and "carbon neutrality".

[0127] The above description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to the embodiments shown herein, but rather to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A condensed-ring sustainable aviation fuel precursor as shown in Formula I: in, R1 is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl or hydrogen; R2-R5 are independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl; or R2 forms a ring with R3 and the carbon atom where they are located, R2 forms a ring with R4 and the carbon atom where they are located, and R4 forms a ring with R5 and the carbon atom where they are located.

2. The condensed-ring sustainable aviation fuel precursor according to claim 1, characterized in that: The R1 is selected from substituted or unsubstituted C1-C3 alkyl, substituted or unsubstituted C6-C15 aryl or hydrogen; R2-R5 are independently selected from hydrogen, substituted or unsubstituted C1-C3 alkyl; or R2 forms a ring with R3 and the carbon atom where they are located, R2 forms a ring with R4 and the carbon atom where they are located, and R4 forms a ring with R5 and the carbon atom where they are located.

3. The condensed-ring sustainable aviation fuel precursor according to claim 1 or 2, characterized in that: The condensed-ring sustainable aviation fuel precursor is selected from any one of the following formulas 1 to 16:

4. A method for preparing a condensed-ring sustainable aviation fuel precursor according to any one of claims 1 to 3, characterized in that: The following steps are involved: In the presence of light and a catalyst, the compound represented by formula A and the compound represented by formula B are copolymerized in a solvent to obtain the condensed-ring sustainable aviation fuel precursor; 5. The preparation method according to claim 4, characterized in that: The catalyst is selected from acetic acid; the solvent includes any one or more of acetonitrile, methanol, ethanol, water, toluene, ethyl acetate, acetone or dichloromethane; The molar ratio of the compound represented by formula A to the compound represented by formula B is (1-4):1; The amount of the catalyst is 0 to 10% of the amount of the compound represented by formula B; The concentration of the compound represented by formula B is 0.05-0.8 mol / L.

6. The preparation method according to claim 4 or 5, characterized in that: The reaction temperature is -20 to 40°C and the reaction time is 1 to 24 hours; Before the reaction is carried out, an inert gas is introduced into the system for 0.5 to 2 h.

7. A condensed-ring sustainable aviation fuel, characterized in that: The condensed-ring sustainable aviation fuel is prepared using the condensed-ring sustainable aviation fuel precursor according to any one of claims 1 to 3 or the condensed-ring sustainable aviation fuel precursor prepared by the preparation method according to any one of claims 4 to 6.

8. The condensed-ring sustainable aviation fuel according to claim 7, characterized in that: The structural formula of the condensed-ring sustainable aviation fuel includes at least one of the formulas (1) to (10):

9. A method for preparing a condensed-ring sustainable aviation fuel as claimed in claim 7 or 8, characterized in that: The following steps are involved: In a hydrogen atmosphere, subjecting the condensed-ring sustainable aviation fuel precursor according to any one of claims 1 to 3 or the condensed-ring sustainable aviation fuel precursor prepared by the preparation method according to any one of claims 4 to 6 to a hydrodeoxygenation reaction in the presence of a catalyst to obtain the condensed-ring sustainable aviation fuel; The catalyst is a combination of an activated carbon-supported noble metal hydrogenation catalyst and a molecular sieve, or a combination of an activated carbon-supported noble metal hydrogenation catalyst and a heteropoly acid.

10. The preparation method according to claim 9, characterized in that: The activated carbon-supported noble metal hydrogenation catalyst includes any one or more of Pd / C, Rh / C, Pt / C or Ru / C; The molecular sieve includes any one or more of HY molecular sieve, LaY molecular sieve, CeY molecular sieve, NaY molecular sieve, ReY molecular sieve, NH4Y molecular sieve, USY molecular sieve, mesoporous Y molecular sieve, ZSM-5 molecular sieve, ZSM-35 molecular sieve, MCM-22 molecular sieve, MCM-41 molecular sieve, β molecular sieve or SAPO molecular sieve; The heteropoly acid includes any one or more of trifluoromethanesulfonate, silicotungstic acid, phosphotungstic acid or phosphomolybdic acid; The pressure of the hydrogen is 0.5-8 MPa; The hydrodeoxygenation reaction time is 1 to 18 hours, and the temperature is 100 to 250°C.

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