Biomass-based high-energy-density aviation fuel and method for preparing high-energy-density aviation fuel through McMurry coupling reaction of biomass-based ketones

Abstract

The invention discloses a biomass-based high-energy-density aviation fuel and a method for preparing the biomass-based high-energy-density aviation fuel through a biomass-based ketone McMurry coupling reaction, and the biomass-based high-energy-density aviation fuel has a structural formula as follows: during preparation, a biomass-based ketone platform compound is taken as a raw material and subjected to the McMurry coupling reaction under the action of a catalyst, and the biomass-based high-energy-density aviation fuel is obtained. The biomass-based pinacol or biomass-based polycyclic olefin derivative is prepared as an aviation oil precursor compound, and the reaction yield can reach 92%; then in an H2 atmosphere, a Pd / C (5-10%) catalyst is selected, a hydrodeoxygenation reaction is carried out under the conditions that the pressure is 5-10 MPa, the temperature is 220-260 DEG C and the time is 4-12 h, biomass-based polycycloalkane is obtained through conversion, and the high-energy-density liquid fuel is obtained. The method can meet the requirements of high-energy-density liquid fuel (greater than or equal to 0.85 g / ml), realizes consideration of freezing point, density and heat value, remarkably improves the yield, improves the utilization rate of raw materials, and is convenient for industrial popularization.

Description

Technical Field

[0001] This invention relates to a biomass-based high-energy-density aviation fuel and a method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones, belonging to the field of organic synthesis technology. Background Technology

[0002] High-energy-density (HED) liquid fuels, due to their high energy density per unit volume, can significantly improve aircraft range, payload, and combustion efficiency. Currently, fossil fuels and biomass are considered the two main sources of HED liquid fuels. However, with the depletion of fossil energy and the goals of carbon neutrality and carbon peaking, the development of HED liquid fuels using renewable energy sources to supplement the depletion of fossil energy has attracted widespread attention.

[0003] The natural cyclic framework of biomass-based feedstocks (cellulose, hemicellulose, lignin, and terpenes, etc.) provides a structural basis for constructing high-density fuel molecules. Simultaneously, the relevant functional groups can also serve as programmable reaction sites, enabling the controlled assembly of ring units, which provides favorable conditions for the subsequent synthesis of high-energy-density liquid fuels. However, the density of straight-chain and monocyclic alkanes obtained by direct hydrogenation and deoxygenation of biomass feedstocks is typically low (≤0.79 g / ml), insufficient to meet the requirements of high-energy-density liquid fuels (≥0.85 g / ml). Currently, biomass-based bicyclic alkane liquid fuels reported in related studies generally suffer from high freezing points, making it difficult to achieve a balance between freezing point, density, and calorific value, while also exhibiting low yields, hindering industrial application. Summary of the Invention

[0004] This invention provides a biomass-based high-energy-density aviation fuel and a method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones. It can meet the requirements of high-energy-density liquid fuel (≥0.85g / ml), achieving a balance between freezing point, density and calorific value, while significantly improving yield and raw material utilization, and facilitating industrial promotion.

[0005] To solve the above-mentioned technical problems, the technical solution adopted by the present invention is as follows:

[0006] A biomass-based high-energy-density aviation fuel, with the following structural formula:

[0007] To better balance density and freezing point, the structural formula for biomass-based high-energy-density aviation fuel is as follows:

[0008] A method for preparing high-energy-density aviation fuel from biomass-based ketones via the McMurry coupling reaction includes the following steps:

[0009] (1) Under the catalytic action of a catalyst and at 40-60℃, biomass-based ketones undergo carbonylation coupling reactions in a solvent for 1-4 hours. After post-treatment, biomass-based pinacol (PNC-1, PNC-2) or polycyclic olefin derivatives (XT-3, XT-4, XT-5) are obtained as high-energy-density fuel precursors. The biomass-based ketones are cyclopentanone, cyclohexanone, isophorone, menthone, or norpinone. The catalyst is at least one of TiCl4 / Zn, AlCl3 / Zn, InCl3 / Zn, TiCl3 / Zn, and SnCl4 / Zn.

[0010] (2) Place biomass-based pinacol or polycyclic olefin derivatives in a high-pressure reactor and carry out a hydrogenation and deoxygenation reaction under the catalysis of Pd / C with a Pd loading of 5-10% to convert them into biomass-based polycyclic alkanes.

[0011] The structure of the biomass-based pinacol or polycyclic olefin derivative is shown below:

[0012]

[0013] The biomass-based pinacol or polycyclic olefin derivatives are named PNC-1, PNC-2 and XT-3, XT-4, XT-5, respectively.

[0014] The structure of the biomass-based polycyclic alkane is shown below:

[0015]

[0016] The biomass-based polycyclic alkane derivatives are named WT-1, WT-2, WT-3, WT-4, and WT-5, respectively.

[0017] The above preparation is simple. After the first step of self-coupling, hydrogen can be added directly for deoxygenation, without the need for dehydration, DA cycloaddition and other steps.

[0018] Unless otherwise specified, all percentages in this application are percentages by mass.

[0019] The reaction equation for step (1) above is:

[0020]

[0021] The reaction equation for step (2) above is:

[0022]

[0023] In step (1), the biomass-based ketone is preferably isophorone; the reaction time is more preferably 4 hours.

[0024] In step (1) above, the preparation method of the catalyst TiCl4 / Zn, AlCl3 / Zn, InCl3 / Zn, TiCl3 / Zn or SnCl4 / Zn is as follows: Under N2 atmosphere, zinc powder and anhydrous tetrahydrofuran are stirred at 0°C, and TiCl4, AlCl3, InCl3, TiCl3 or SnCl4 are added. The reaction is carried out at 0°C for 20-30 minutes, and then the temperature is raised to 60-70°C and the reaction is continued for 2-4 hours. The reaction system is cooled to 0°C, pyridine is added, and the mixture is stirred for 5-10 minutes to obtain the target catalyst. The amount of pyridine used is n(pyridine):n(TiCl4) = 1:2. The molar ratio of TiCl4, AlCl3, InCl3, TiCl3 or SnCl4 to zinc powder is (3-6):1, more preferably 5:1. The ratio of zinc powder to anhydrous tetrahydrofuran is (0.13-1.6) g:40 mL.

[0025] To further improve the product yield, in step (1), the catalyst is preferably TiCl4 / Zn, and the molar ratio of TiCl4 to Zn is (3-6):1, more preferably 5:1.

[0026] In step (1) above, the material ratio of the catalyst is n(biomass base ketone):n(zinc powder in the catalyst) = 1:2~10, and the reaction solvent is tetrahydrofuran, toluene or diethyl ether, more preferably tetrahydrofuran.

[0027] In order to improve the purity of the product, the post-processing method after the reaction in step (1) above is as follows: the reaction temperature is lowered to room temperature, the reaction is quenched with a 10% potassium carbonate aqueous solution, extracted with dichloromethane, washed with saturated brine and water in sequence, dried with anhydrous sodium sulfate, and crystallized at low temperature to obtain biomass-based pinacol or polycyclic olefin derivatives.

[0028] In step (2) above, the mass ratio of biomass-based pinacol or polycyclic olefin derivative to Pd / C is 1:(0.01-0.1), the reaction temperature is 200-220℃, the reaction pressure is 2-5MPa, and the reaction time is 4-6h.

[0029] In step (2) above, cyclohexane is used as the reaction solvent, and the ratio of solvent to biomass-based pinacol or polycyclic olefin derivative is (0.8-1.2) mL: 1 g.

[0030] After the reaction in step (2) above is completed, the following post-processing is performed: the reaction solution is filtered through a sand core funnel and then concentrated under reduced pressure.

[0031] Any techniques not mentioned in this invention are based on existing technologies.

[0032] Compared with the prior art, the present invention has the following advantages:

[0033] 1. This invention can completely achieve the high-yield preparation of high-energy-density aviation fuel from biomass platform compounds such as cyclopentanone, cyclohexanone, menthone, menthone and norpinone in two steps. The density of each of them is greater than 0.85 g / mL, which is a high-performance aviation kerosene alkane compound.

[0034] 2. The entire route uses biomass-based platform compounds as raw materials, making it a novel and green route that does not produce harmful substances and is simple and easy to operate.

[0035] 3. Through method improvements, the precursor yield can reach over 92%, significantly improving the utilization rate of raw materials and facilitating industrial production.

[0036] 4. The high-energy-density aviation fuel of this invention also achieves a balance between freezing point, density, and calorific value. Attached Figure Description

[0037] Figure 1 .1H NMR spectrum of PNC-1 synthesized in Example 1;

[0038] Figure 2 13C NMR spectrum of PNC-1 synthesized in Example 1;

[0039] Figure 3 .1H NMR spectrum of PNC-2 synthesized in Example 18;

[0040] Figure 4 13C NMR spectrum of PNC-2 synthesized in Example 18;

[0041] Figure 5 1H NMR spectrum of XT-3 synthesized in Example 19;

[0042] Figure 6 13C NMR spectrum of XT-3 synthesized in Example 19;

[0043] Figure 7 1H NMR spectrum of XT-4 synthesized in Example 20;

[0044] Figure 8 Example 20: 13C NMR spectrum of synthesized XT-4;

[0045] Figure 9 1H NMR spectrum of XT-5 synthesized in Example 21;

[0046] Figure 10 Example 21: 13C NMR spectrum of synthesized XT-5;

[0047] Figure 11 GC-MS spectrum of WT-1 synthesized in Example 22;

[0048] Figure 12 GC-MS spectrum of WT-2 synthesized in Example 23;

[0049] Figure 13 GC-MS spectrum of WT-3 synthesized in Example 24;

[0050] Figure 14 GC-MS spectrum of WT-4 synthesized in Example 25;

[0051] Figure 15 GC-MS spectrum of WT-5 synthesized in Example 26; Detailed Implementation

[0052] To better understand the present invention, the following embodiments further illustrate the content of the present invention, but the content of the present invention is not limited to the following embodiments.

[0053] Unless otherwise specified, all examples were conducted at room temperature (15–25°C); unless otherwise specified, all examples were conducted at a stirring speed of 200 r / min.

[0054] Example 1

[0055] Preparation of PNC-1:

[0056] (1) In a reaction system at 0℃, 1.6 g of zinc powder (24 mmol) and 40 mL of anhydrous tetrahydrofuran were added to a 250 mL three-necked flask under nitrogen protection. Then, 1.3 mL of titanium tetrachloride (12 mmol) solution was slowly added dropwise (45 drops / min) while stirring continuously for 30 minutes. After stirring, the reaction temperature was adjusted to 60–70℃ and the reaction was continued for 2 hours. Finally, the system was cooled to 0℃, and 0.5 mL of pyridine (6 mmol) was added while stirring continuously for 10 minutes to obtain a tetrahydrofuran solution containing TiCl4 / Zn.

[0057] (2) The temperature was adjusted to room temperature. 2.4 mmol of cyclopentanone was dissolved in 15 ml of tetrahydrofuran solution. Then, it was slowly added dropwise to the tetrahydrofuran solution containing TiCl4 / Zn obtained in step (1) through a constant pressure dropping funnel. The reaction temperature was adjusted to 40 °C and the reaction was allowed to proceed for 4 h. After the reaction was complete, the system was cooled to room temperature and the reaction was quenched with 100 ml of potassium carbonate aqueous solution (10%). The mixture was then extracted with dichloromethane (3 × 20 mL, 3 times, 20 mL of dichloromethane each time). The organic phases were combined, washed 3 times (50 ml × 3) with saturated brine, and then washed 3 times (50 ml × 3) with pure water. The mixture was dried over anhydrous sodium sulfate and crystallized at low temperature to obtain cyclopentanone-based pinacol PNC-1.

[0058] like Figure 1 As shown, 1 H NMR (400MHz, DMSO-d6) δ3.87(s,1H,11-OH,12-OH),1.81–1.66(m,4H,8-CH2,9-CH2,2-CH2,1-CH2),1.51–1.35(m,4H,3-CH2,5-CH2,7-CH2,10-CH2).

[0059] like Figure 2 As shown, 13 C NMR (101MHz, DMSO) δ = 85.27 (C-2, C-6), 35.66 (C-3, C-5, C-7, C-10), 25.71 (C-1, C-2, C-9, C-8).

[0060] Example 2

[0061] In Example 1, the amount of zinc powder used in step (1) was replaced with 12 mmol, and the rest was the same as in Example 1.

[0062] Example 3

[0063] In Example 1, the amount of zinc powder used in step (1) was replaced with 6 mmol, and the rest was the same as in Example 1.

[0064] Example 4

[0065] In Example 1, the amount of zinc powder used in step (1) was replaced with 4 mmol, and the rest was the same as in Example 1.

[0066] Example 5

[0067] In Example 1, the amount of zinc powder used in step (1) was replaced with 3 mmol, and the rest was the same as in Example 1.

[0068] Example 6

[0069] In Example 1, the amount of zinc powder used in step (1) was replaced with 2.4 mmol, and the rest was the same as in Example 1.

[0070] Example 7

[0071] In Example 1, the amount of zinc powder used in step (1) was replaced with 2 mmol, and the rest was the same as in Example 1.

[0072] Example 8

[0073] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, the reaction time in step (2) was replaced with 1 h, and the rest were the same as in Example 1.

[0074] Example 9

[0075] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, the reaction time in step (2) was replaced with 2 h, and the rest were the same as in Example 1.

[0076] Example 10

[0077] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, the reaction time in step (2) was replaced with 3 h, and the rest were the same as in Example 1.

[0078] Example 11

[0079] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, the reaction time in step (2) was replaced with 5 h, and the rest were the same as in Example 1.

[0080] Example 12

[0081] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, and the tetrahydrofuran in step (2) was replaced with toluene. All other steps were the same as in Example 1.

[0082] Example 13

[0083] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, and the tetrahydrofuran in step (2) was replaced with diethyl ether. All other steps were the same as in Example 1.

[0084] Example 14

[0085] In Example 1, in step (1), the amount of zinc powder was replaced with 2.4 mmol, and titanium tetrachloride was replaced with an equimolar amount of AlCl3 (the time taken to add AlCl3 was basically the same as the time taken to add titanium tetrachloride in Example 1), thus obtaining the AlCl3 / Zn catalyst; in step (2), when the reaction time was 4 h, the yield was <5%, so the reaction time was extended to 14 h, and the rest were the same as in Example 1.

[0086] Example 15

[0087] In Example 1, in step (1), the amount of zinc powder was replaced with 2.4 mmol, and titanium tetrachloride was replaced with an equimolar amount of InCl3 (the time taken to add InCl3 was basically the same as the time taken to add titanium tetrachloride in Example 1), thus obtaining the InCl3 / Zn catalyst; in step (2), when the reaction time was 4 h, the yield was <5%, so the reaction time was extended to 14 h, and the rest were the same as in Example 1.

[0088] Example 16

[0089] In Example 1, in step (1), the amount of zinc powder was replaced with 2.4 mmol, and titanium tetrachloride was replaced with an equimolar amount of TiCl3 (the time taken to add TiCl3 was basically the same as the time taken to add titanium tetrachloride in Example 1), to obtain the TiCl3 / Zn catalyst; in step (2), when the reaction time was 4 h, the yield was <35%, so the reaction time was extended to 6 h, and the rest were the same as in Example 1.

[0090] Example 17

[0091] In Example 1, in step (1), the amount of zinc powder was replaced with 2.4 mmol, and titanium tetrachloride was replaced with an equimolar amount of SnCl4 (the time taken to add SnCl4 was basically the same as the time taken to add titanium tetrachloride in Example 1), to obtain the SnCl4 / Zn catalyst; in step (2), when the reaction time was 4 h, the yield was <35%, so the reaction time was extended to 6 h, and the rest were the same as in Example 1.

[0092] Table 1. Effects of catalyst dosage, time, and different catalyst types on biomass-based ketone carbonylation coupling reaction

[0093]

[0094] As shown in Table 1, the catalyst formed by TiCl4 / Zn exhibits good catalytic performance in the self-McMurry coupling reaction of biomass-based ketones. When n(TiCl4):n(Zn) = 5, the yield can reach 92%, which significantly improves the utilization rate of raw materials.

[0095] Example 18

[0096] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, and the amount of cyclopentanone in step (2) was replaced with an equimolar amount of cyclohexanone. All other steps were the same as in Example 1. The biomass-based pinacol derivative PNC-2 was obtained with a yield of 90%. 1 HNMR and 13 C NMR (see) Figure 3-4 .

[0097] Example 19

[0098] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, and the amount of cyclopentanone in step (2) was replaced with an equimolar amount of isophorone. All other steps were performed according to Example 1. Biomass-based polycyclic olefin derivative XT-3 was obtained with a yield of 95%. 1 H NMR and 13 C NMR (see) Figure 5-6 .

[0099] Example 20

[0100] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, and the amount of cyclopentanone in step (2) was replaced with an equimolar amount of menthone. All other steps were the same as in Example 1, and the biomass-based polycyclic olefin derivative XT-4 was obtained with a yield of 89%. 1 HNMR and 13 C NMR (see) Figure 7-8 .

[0101] Example 21

[0102] In Example 1, the amount of zinc powder in step (1) was replaced with 2.4 mmol, and the amount of cyclopentanone in step (2) was replaced with an equimolar amount of (-)-norpinone. All other steps were the same as in Example 1, and the biomass-based polycyclic olefin derivative XT-5 was obtained with a yield of 83%. 1 H NMR and 13 C NMR (see) Figure 9-10 .

[0103] Example 22

[0104] 50 g of cyclopentanone-based pinacol (PNC-1) was added to a 500 mL high-pressure reactor and dissolved in 50 mL of cyclohexane. Then, 2.5 g of Pd / C (5%) catalyst was added, and the reaction was carried out at 220 °C and 5 MPa for 6 h. After the reaction was complete, the Pd / C catalyst was removed by filtration, and the solvent was removed by rotary evaporation to obtain cyclopentanone-based polycyclic alkanes (WT-1) in 98% yield. GC-MS spectra are shown below. Figure 11 .

[0105] Example 23

[0106] The difference from Example 22 is that cyclohexanone-based pinacol PNC-1 was replaced with biomass-based pinacol derivative PNC-2, while all other steps were the same as in Example 22, yielding biomass-based polycyclic alkane derivative WT-2 with a yield of 99%. GC-MS spectra are shown below. Figure 12 .

[0107] Example 24

[0108] The difference from Example 22 is that cyclopentanone-pinacol PNC-1 was replaced with biomass-based polycyclic olefin derivative XT-3, while all other steps were the same as in Example 22, yielding biomass-based polycyclic alkane derivative WT-3 with a yield of 98%. GC-MS spectra are shown below. Figure 13 .

[0109] Example 25

[0110] The difference from Example 22 is that cyclopentanone-based pinacol PNC-1 was replaced with biomass-based polycyclic olefin derivative XT-4, while all other steps were the same as in Example 22, yielding biomass-based polycyclic alkane derivative WT-4 with a yield of 99%. GC-MS spectra are shown below. Figure 14 .

[0111] Example 26

[0112] The difference from Example 22 is that cyclopentanone-based pinacol PNC-1 was replaced with biomass-based polycyclic olefin derivative XT-5, while all other steps were the same as in Example 22, yielding biomass-based polycyclic alkane derivative WT-5 in 99% yield. GC-MS spectra are shown below. Figure 15 .

[0113] The density, freezing point, and volumetric calorific value of the biomass-based polycyclic alkane derivatives of Examples 22-26 were tested according to the method shown in GB 6537-2018. The key properties of the high-density biomass fuels obtained in Examples 25-28, including density, calorific value, and freezing point, are described. See Table 2 for details.

[0114] Table 2. Fuel performance of biomass-based polycyclic alkanes WT-1, WT-2, WT-3, WT-4 and WT-5.

[0115]

[0116] Table 2 shows that the densities of the biomass-based polycyclic alkanes (WT-1, WT-2, WT-3, WT-4, and WT-5) prepared by the two-step method are all above 0.85 g / ml. Among them, WT-5 has the best density, at 0.911 g / ml. WT-3 exhibits a significantly better freezing point, at -77.2℃. In terms of calorific value, WT-1, WT-2, WT-3, WT-4, and WT-5 also show outstanding performance, with volumetric calorific values ​​all at or above 35 MJ / L. Among them, WT-3 has the highest calorific value, at 39.22 MJ / L. In conclusion, WT-3 can be considered a high-performance aviation fuel.

[0117] The above description is merely a specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any modifications, equivalent substitutions, and improvements made by those skilled in the art within the scope of the technology disclosed in the present invention, and within the spirit and principles of the present invention, should be covered within the scope of protection of the present invention.

Claims

1. A biomass-based high-energy-density aviation fuel, characterized in that: Its structural formula is:

2. The biomass-based high-energy-density aviation fuel according to claim 1, characterized in that: Its structural formula is:

3. A method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones, characterized in that, Includes the following steps: (1) Under the catalytic action of a catalyst and at 40-60℃, biomass-based ketones undergo carbonylation coupling reactions in a solvent for 1-4 hours. After post-treatment, biomass-based pinacol or polycyclic olefin derivatives are obtained. The biomass-based ketones are cyclopentanone, cyclohexanone, isophorone, menthone, or norpinone. The catalyst is at least one of TiCl4 / Zn, AlCl3 / Zn, InCl3 / Zn, TiCl3 / Zn, and SnCl4 / Zn. (2) Place biomass-based pinacol or polycyclic olefin derivatives in a high-pressure reactor and carry out a hydrogenation and deoxygenation reaction under the catalysis of Pd / C with a Pd loading of 5-10% to convert them into biomass-based polycyclic alkanes. The structure of the biomass-based pinacol or polycyclic olefin derivative is shown below: The structure of the biomass-based polycyclic alkane is shown below:

4. The method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones according to claim 3, characterized in that, In step (1), the preparation method of catalyst TiCl4 / Zn, AlCl3 / Zn, InCl3 / Zn, TiCl3 / Zn or SnCl4 / Zn is as follows: Under N2 atmosphere, zinc powder and anhydrous tetrahydrofuran are stirred at 0℃, and TiCl4, AlCl3, InCl3, TiCl3 or SnCl4 are added. The reaction is carried out at 0℃ for 20 to 30 minutes. Then, the temperature is raised to 60 to 70℃ and the reaction is continued for 2 to 4 hours. The reaction system is cooled to 0℃, pyridine is added, and the mixture is stirred for 5 to 10 minutes to obtain the target catalyst. The amount of pyridine used is n(pyridine):n(TiCl4) = 1:2; the molar ratio of TiCl4, AlCl3, InCl3, TiCl3 or SnCl4 to zinc powder is (3 to 6):1; and the ratio of zinc powder to anhydrous tetrahydrofuran is (0.13 to 1.6) g:40 mL.

5. The method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones according to claim 3 or 4, characterized in that, In step (1), the catalyst is TiCl4 / Zn, and the molar ratio of TiCl4 to Zn is (3-6):

1.

6. The method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones according to claim 5, characterized in that, The molar ratio of TiCl4 to Zn is 5:

1.

7. The method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones according to claim 3 or 4, characterized in that, In step (1), the material ratio of the catalyst is n(biomass base ketone):n(zinc powder in the catalyst) = 1:2~10, and the reaction solvent is tetrahydrofuran, toluene or diethyl ether.

8. The method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones according to claim 3 or 4, characterized in that, In step (1), the post-processing method after the reaction is completed is as follows: the reaction temperature is lowered to room temperature, the reaction is quenched with a 10% potassium carbonate aqueous solution, extracted with dichloromethane, washed successively with saturated brine and water, dried with anhydrous sodium sulfate, and crystallized at low temperature to obtain biomass-based pinacol or polycyclic olefin derivatives.

9. The method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones according to claim 3 or 4, characterized in that, In step (2), the mass ratio of biomass-based pinacol or polycyclic olefin derivative to Pd / C is 1:(0.01-0.1), the reaction temperature is 200-220℃, the reaction pressure is 2-5MPa, and the reaction time is 4-6h.

10. The method for preparing high-energy-density aviation fuel from the McMurry coupling reaction of biomass-based ketones according to any one of claims 3-5, characterized in that, In step (2), cyclohexane is used as the reaction solvent, and the ratio of solvent to biomass-based pinacol or polycyclic olefin derivative is (0.8-1.2) mL: 1 g.

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