A method for preparing high-density multi-ring aviation fuel from biomass platform compounds

Abstract

The present invention discloses a method for preparing high-density polycyclic aviation fuel from biomass platform compounds. The specific steps are: the first step is self-reduction coupling of cyclic ketone to vicinal diol under acid catalysis; the second step is selective dehydration of vicinal diol to conjugated diene under the action of acid catalyst; the third step is D-A cycloaddition reaction of conjugated diene and p-benzoquinone to generate high-density polycyclic aviation fuel precursor; the fourth step is hydrogenation and deoxygenation of high-density polycyclic fuel precursor under the co-catalysis of Metal / C and solid acid catalyst to obtain high-density polycyclic aviation fuel. The present invention provides a method for preparing high-density polycyclic aviation fuel from biomass platform compounds. From the perspective of the entire preparation process, the raw material source is green, the separation of products is simple, and the operation is convenient.

Description

Technical Field

[0001] The invention relates to the technical field of organic synthesis of compounds, and in particular to a method for preparing high-density multi-ring aviation fuel from biomass platform compounds. Background Art

[0002] With the rapid development of my country's aerospace technology and national defense, meeting the demand for high-density fuel has become an important means to promote the rapid development of my country's aerospace and national defense. High-density fuel refers to hydrocarbon liquid fuel with a density higher than 0.80g / mL. Compared with traditional aviation fuel, it has higher density, calorific value and lower freezing point. Without increasing the volume of the fuel tank, the aircraft has a longer range and higher load, and can better meet the needs of special situations. Therefore, from a long-term perspective, the development of high-density fuel is of great strategic significance for promoting the development of my country's aviation and national defense. In recent years, the development of biomass resources has aroused the interest of scientific researchers, and the preparation of high-density aviation fuel from biomass resources has become a major research hotspot.

[0003] The production of biomass-based platform compound cyclopentanone can be obtained by selective hydrogenation rearrangement of furfural in water (ACS Sustain. Chem. Eng. 2014, 2, 2259; Green Chem. 2015, 17, 4183), the selective hydrogenation of lignin simple model compound phenol can obtain cyclohexanone (ACS Sustain. Chem. Eng. 2016, 4, 3850), and p-benzoquinone can be obtained by oxidation of lignin platform compound hydroquinone (The Journal of Organic Chemistry 2002, 48 (26), 5160-5164). Up to now, the preparation of high-density fuels is mostly parallel multi-ring systems. The looseness between the rings makes the calorific value of the fuel low, which cannot meet the needs of special situations. Summary of the invention

[0004] The purpose of the present invention is to provide a method for preparing high-density multi-ring aviation fuel from biomass platform compounds, which has simple product separation steps and high yield and can produce high-density aviation fuel.

[0005] To achieve the above object, the technical solution adopted by the present invention is as follows: A method for preparing high-density multi-ring aviation fuel from biomass platform compounds, comprising the following steps:

[0006] In the first step, under an inert atmosphere, a cyclic ketone undergoes a self-reduction coupling reaction under the action of an acid catalyst A to generate a vicinal diol product 2 having a bicyclic structure; the cyclic ketone is cyclohexanone or cyclopentanone, that is, in the formula, n=0 or 1;

[0007]

[0008] In the second step, the vicinal diol product 2 is selectively dehydrated in an ionic liquid solvent under the action of an acid catalyst B to generate a bicyclic conjugated diene 3;

[0009]

[0010] In the third step, the bicyclic conjugated diene 3 undergoes a DA cycloaddition reaction with p-benzoquinone 4 under catalyst-free and solvent-free conditions to generate a high-density multicyclic aviation fuel precursor 5;

[0011]

[0012] In the fourth step, the high-density polycyclic aviation fuel precursor 5 is hydrodeoxygenated under the catalysis of a supported catalyst or the co-catalysis of Metal / C and a solid acid catalyst to obtain a high-density polycyclic aviation fuel 6.

[0013]

[0014] Preferably, in the first step, the acid catalyst A is selected from one or two of the following catalysts: HgCl2, TiCl4, and the reducing metal is selected from one or more of the following: Fe, Mg, Al, Zn, Ce.

[0015] Preferably, in the second step, the acidic catalyst B is selected from one or more of the following catalysts: AlCl3, FeCl3, Sc(OTf)3, Nafion, MMT, MMT-KSF, MMT K-10, T-62MP, Amberlyst-36, Amberlyst-15, Fe(OTf)3, Al(OTf)3, ZnCl2, Zn(OTf)2, HPW, HPMo, FeCl2, CuCl, CeCl3, La(OTf)3, Ca(NTf2)2, B(C6F5)3, Nb2O5, ZrPO, ZrO2, TSA, H2SO4, TFA, MSA; wherein the ratio of the mass of the acid catalyst B to the mass of the vicinal diol product is between 0.01 and 1.

[0016] Preferably, in the second step, the ionic liquid is one or more of the following: 1,3-dimethylimidazolium dimethyl phosphate ([Mmim][Me2PO4]), 1-ethyl-3-methylimidazolium fluoride ([Emim][F]), 1-ethyl-3-methylimidazolium chloride ([Emim][Cl]), 1-ethyl-3-methylimidazolium bromide ([Emim][Br]), 1-ethyl-3-methylimidazolium hydrogen sulfate ([Emim][HSO4]), 1-ethyl-3-methylimidazolium acetate ([Emim][OAc]), 1-ethyl-3-methylimidazolium tetrafluoroborate ([Emi m][BF4]), 1-ethyl-3-methylimidazolium thiocyanate ([Emim][SCN]), 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Emim][NTf2]), 1-ethyl-3-methylimidazolium dimethyl phosphate ([Emim][(MeO)2PO2]), 1-ethyl-3-methylimidazolium dicyanamide [Emim][DCA], 1-ethyl-3-methylimidazolium ethyl sulfate ([Emim][EtOSO3]), 1-ethyl-3-methylimidazolium toluenesulfonyl ester ([Emim][Tos]), 1-ethyl-3-methylimidazolium diethyl phosphonate ([Emim][(MeO)2PO2]), 1-ethyl-3-methylimidazolium dicyanamide ([Emim][DCA]), 1-ethyl-3-methylimidazolium ethyl sulfate ([Emim][EtOSO3]), 1-ethyl-3-methylimidazolium toluenesulfonyl ester ([Emim][Tos]), 1-ethyl-3-methylimidazolium diethyl phosphonate acid salt [Emim][(EtO)2PO2], 1-butyl-3-methylimidazolium dicyanamide ([Bmim][DCA]), 1-butyl-3-methylimidazolium chloride ([Bmim][Cl]), 1-butyl-3-methylimidazolium methanesulfonate ([Bmim][MeSO4]), 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim][BF4]), 1-butyl-3-methylimidazolium hexafluorophosphate ([Bmim][PF6]), 1-hexyl-3-methylimidazolium hydrogen sulfate ([Hmim][HSO4]); N-butylpyridinium nitrate ([BPy][NO3]) , N-butylpyridinium bis(trifluoromethanesulfonyl)imide ([BPy][TFSI]), N-butylpyridinium bis(trifluoromethanesulfonyl)imide salt ([BPy][NTf2]), N-hexylpyridinium nitrate ([HPy][NO3]), N-octylpyridinium nitrate ([OPy][NO3]), N-ethylpyridinium tetrafluoroborate ([EPy][BF4]), N-ethylpyridinium hexafluorophosphate ([EPy][PF6]), N-butylpyridinium bis(trifluoromethanesulfonyl)imide salt ([PPy][NTf2]), 1-butyl-3-methylpyridinium thiocyanate ([BMPy][SCN]);triethylammonium chloride ([Et3NH][Cl]), 1-butyl-1-methylpyrrole thiocyanate ([BMPyrr][SCN]), 1-butyl-1-methylpyrrole trifluoroacetate ([BMPyrr][TFA]), 1-butyl-1-methylpyrrole dicyanamide ([BMPyrr][DCA]), 1-methyl-1-ethylpyrrole dicyanamide ([EMPyrr][DCA]), 1-hexyl-1-methylpyrrole thiocyanate ([HMPyrr][SCN]), 1-octyl-1-methylpyrrole thiocyanate [OMPyrr][SCN]; choline chloride / succinic acid (ChCl / succinic acid), choline chloride / glycerol (ChCl / glycerol), choline chloride / citric acid (ChCl / citric acid), choline chloride / lactic acid (ChCl / lactic acid), choline chloride / adipic acid (ChCl / adipic acid), choline chloride / malonic acid (ChCl / malonic acid) acid), choline chloride / urea (ChCl / urea), choline chloride / ethylene glycol (ChCl / EG), choline chloride / p-toluenesulfonic acid (ChCl / pTSA), ChCl / 2ZnCl2, ChCl / 2FeCl3, ChCl / 2SnCl;

[0017] Wherein, the amount of the ionic liquid is between 0.5 and 5 times the mass of the vicinal diol.

[0018] Preferably, in the first step, the selected solvent is diethyl ether or tetrahydrofuran, the reaction temperature is 40-70° C., the reaction time is 12-18 h, and the substrate concentration range is 0.1-1 mol / L.

[0019] Preferably, in the second step, the reaction temperature is 100-140° C. and the reaction time is 2-8 h.

[0020] Preferably, in the third step, the reaction temperature is 40-80° C., the reaction time is 0.5-2 h, and the molar ratio of the bicyclic conjugated diene 3 to the p-benzoquinone 4 is 1:1 to 2:1.

[0021] Preferably, in the fourth step, the carrier in the supported catalyst is one or more of Amberlyst-15, Amberlyst-36, Nafion membrane, HY, H-ZSM-5, H-Beta, H-MOR, H-SAPO-34, the active metal is one or more of Ni, Cu, Fe, Au, Pd, Pt, Ru, Rh, Ir, and the metal mass loading is 3-8%; or in the hydrodeoxygenation catalyst, Metal / C is The catalyst is one or more of Pt / C, Pd / C, Ru / C, Ir / C, Rh / C, Co / C, Ni / C and Fe / C; the solid acid catalyst is one or more of Amberlyst-15, Amberlyst-36, Nafion membrane, HY, H-ZSM-5, H-Beta, H-MOR and H-SAPO-34; wherein the ratio of the amount of the catalyst to the mass of the polycyclic aviation fuel precursor 5 is between 0.01 and 0.3.

[0022] Preferably, in the fourth step, the solvent used is selected from one or more of cyclohexane, propylene carbonate, methanol, propanol, isopropanol, acetonitrile, tridecane, toluene, tetrahydrofuran, N,N-dimethylformamide, and n-hexane, and the substrate concentration range is 0.01-1 mol / L.

[0023] Preferably, in the fourth step, the hydrodeoxygenation reaction is carried out in a tank reactor; the temperature is 160-200°C, the reaction time is 12-15h, and the hydrogen pressure is 3-5MPa.

[0024] Compared with the prior art, the present invention has the following beneficial effects:

[0025] 1. The present invention can completely realize the preparation of high-density multi-cyclic aviation fuel with high yield from biomass platform compounds cyclic ketone and p-benzoquinone through a four-step method. The density of the high-density multi-cyclic aviation fuel is greater than 0.90 g / mL, and the high-performance aviation kerosene alkane compound is obtained.

[0026] 2. The entire route uses biomass as raw material. It is a new green route that does not produce harmful substances. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 Cyclopentanone is used as the raw material to generate vicinal diol products by reductive coupling. 1 H-NMR spectrum;

[0028] Figure 2 Cyclopentanone is used as the raw material to generate vicinal diol products by reductive coupling. 13 C-NMR spectrum;

[0029] Figure 3 The selective dehydration of vicinal diols into dienes as raw materials in Example 11 H-NMR spectrum;

[0030] Figure 4 The selective dehydration of vicinal diols into dienes as raw materials in Example 1 13 C-NMR spectrum;

[0031] Figure 5 Example 16 is the reaction of diene and p-benzoquinone DA to generate precursor 5a 1 H-NMR spectrum;

[0032] Figure 6 Example 16 is the reaction of diene and p-benzoquinone DA to generate precursor 5a 13 C-NMR spectrum. DETAILED DESCRIPTION

[0033] The present invention is further described in detail below with reference to the accompanying drawings and specific embodiments.

[0034] Unless otherwise specified, the raw materials and reagents used in the following examples are all commercially available products, and the purity is analytical grade or higher.

[0035] The preparation process of the vicinal diol product used in the following examples is as follows:

[0036] Under N2 atmosphere, TiCl4 (11mL, 0.1mol) was added to a suspension of zinc powder (26g, 0.4mol) and tetrahydrofuran (250mL). After stirring for 15min, cyclopentanone (8.412g, 0.1mol) was added. The reaction mixture was then refluxed and reacted at 60°C for 15h under N2 atmosphere. After the reaction was completed, saturated sodium bicarbonate was used for quenching, the suspension was filtered and extracted with ethyl acetate for 4-5 times, and then dried, concentrated and recrystallized to obtain the vicinal diol product.

[0037] The obtained vicinal diol product 1 H-NMR spectrum Figure 1 As shown, 13 C-NMR spectrum Figure 2 shown. 1 H NMR(400MHz,Chloroform-d)δ2.24(s,2H),1.89-1.49(m,16H). 13 C NMR (101MHz, Chloroform-d) δ87.26, 36.45, 24.92.

[0038] Examples 1-6

[0039] Selective dehydration of bicyclic five-membered vicinal diols under acidic conditions to generate compound 3a (effect of catalyst)

[0040] In a 35 mL reaction tube, 0.5 g of vicinal diol 2a, 8 wt% of catalyst, and 2.5 g of [Hmim]Cl ionic liquid were added in sequence and reacted at 110° C. for 6 h.

[0041]

[0042] Table 1. Effects of different catalysts on the dehydration reaction of vicinal diols

[0043]

[0044]

[0045] From the results in Table 1, it can be seen that Nafion, T-62MP and H2SO4 obtain better 3a selectivity, HPW and HPMo catalysts have poor catalytic performance, and Amberlyst-15 is the most active catalyst with a 3a yield of 85.2%.

[0046] Example 1 Synthesis of Diene 1 H-NMR spectrum Figure 3 As shown, 13 C-NMR spectrum Figure 4 shown. 1 HNMR(400MHz,Chloroform-d)δ6.13-5.14(m,2H),2.53-2.45(m,4H),2.42(ddq,J=5.6,3.7,1.8Hz,4H),1.99-1.85(m,4H). 13 C NMR (101MHz, Chloroform-d) δ140.39,126.64,33.03,32.87,23.42.

[0047] Example 7-12

[0048] Since the catalyst cannot be recycled in practical applications, the recycling of ionic liquid Amberlyst-15 / [Hmim]Cl was studied under solvent-free conditions at 110°C for 6 hours. After the first reaction, the product is insoluble in the highly polar ionic liquid and will automatically separate into two phases, the upper layer is the product, and the lower layer is the ionic liquid and the catalyst. The separated product was dehydrated at 80°C in vacuum for 4 hours, and the vicinal diol was added to carry out the next cycle experiment. It can be seen from the results in Table 2 that after Amberlyst-15 / [Hmim]Cl was recycled five times, the yield of the bicyclic five-membered conjugated diene did not change significantly, which shows that the system can be reused.

[0049] Table 2. Changes in the yield of compound 3a with the number of cycles

[0050]

[0051] Examples 13-16

[0052] DA Cycloaddition Reaction of Bicyclic Five-Membered Conjugated Dienes and p-Benzoquinone (Effect of Molar Ratio)

[0053] In a 35 mL sealed tube, p-benzoquinone 4 and bicyclic five-membered conjugated diene 3a were added in sequence, and the reaction was stirred at 60°C without solvent until the reaction system agglomerated.

[0054]

[0055] Table 3. Effect of substrate molar ratio on DA cycloaddition reaction

[0056]

[0057] It can be seen from the results in Table 3 that in the DA cycloaddition reaction under solvent-free conditions, the yield of product 5a also increases with the increase of the substrate molar ratio. At a molar ratio of 2:1, the yield of product 5a is as high as 88.3%.

[0058] The hydrogen spectrum of the precursor 5a prepared in Example 16 is as follows Figure 5 As shown, 13 C-NMR spectrum Figure 6 shown. 1 H NMR (400MHz, Chloroform-d) δ6.58 (s, 2H), 3.38 (d, J = 5.4Hz, 2H), 2.65-2.42 (m, 2H), 2.18 (s, 4H), 1.86 (t, J = 3.6Hz, 2H), 1.77-1.50 (m, 6H). 13 C NMR (101MHz, Chloroform-d) δ200.66,140.94,133.17,50.14,41.41,29.42,28.22,24.10.

[0059] Examples 17-24

[0060] Experiment on Hydrodeoxygenation of High-Density Multi-Ring Aviation Fuel (Effects of Temperature and Catalyst on Reaction)

[0061] In a 50mL reactor, polycyclic fuel precursor 5a (0.242g, 1mmol) and cyclohexane (2mL) were added, and then 48.4mg of catalyst was added. The reaction was carried out at a certain temperature and hydrogen pressure (3.0MPa) for 15h to obtain high-density polycyclic aviation fuel 6a.

[0062]

[0063] Table 4. Effects of temperature and catalyst on hydrodeoxygenation reaction

[0064]

[0065] From the results in Table 4, it can be seen that although the hydrogenation capabilities of different metal catalysts are different, they are all effective in the hydrodeoxygenation reaction of the polycyclic aviation fuel precursor 5a when used in combination with the acidic solid catalyst HY. Among them, the activity of metals Pt, Pd and Rh is the best. Pd / C and HY are selected as catalysts for hydrodeoxygenation for cost considerations. Temperature has a great influence on the hydrodehydrogenation reaction. At 160°C, the yield of the hydrodeoxygenation product 6a is only 69%. When the temperature is increased to 180°C, the yield of the target product can reach 85%. When the temperature is increased to 200°C, the reaction reaches the maximum yield. Continuing to increase the temperature to 220°C does not increase the yield of the reaction, so 200°C is selected as the optimal reaction temperature.

[0066] From the above examples, it can be seen that the high-density fuel prepared from the biomass platform compounds cyclopentanone and p-benzoquinone based on the above four-step method has a density of 0.966 g / mL, a calorific value of 43.3 MJ / L, and a freezing point of -70°C; it has physical properties comparable to those of commercial petroleum-based fuels JP-10, RJ-4, and RJ-5 fuels (see Table 5), and is a relatively good aviation fuel. The entire route uses biomass as raw material, which is a new green and environmentally friendly route that does not produce harmful substances.

[0067] Table 5. Structure and properties of typical petroleum-derived HED fuels.

[0068]

[0069]

[0070] The embodiments given in the present invention are all prepared using cyclohexanone as the starting material. Since cyclohexanone and cyclopentanone are homologues with similar chemical properties, it is foreseeable that high-density multi-ring aviation fuel can be prepared using cyclopentanone as the starting material.

[0071] The above description is only a specific implementation mode of the present invention, but the protection scope of the present invention is not limited thereto. Any modifications, equivalent substitutions and improvements made by any technician familiar with the technical field within the technical scope disclosed by the present invention and within the spirit and principle of the present invention should be covered by the protection scope of the present invention.

Claims

1. A method for preparing high-density multi-ring aviation fuel from biomass platform compounds, characterized in that: The following steps are involved: In the first step, under an inert atmosphere, a cyclic ketone undergoes a self-reduction coupling reaction under the action of an acid catalyst A to generate a vicinal diol product 2 having a bicyclic structure; the cyclic ketone is cyclohexanone or cyclopentanone, that is, in the formula, n=0 or 1; In the second step, the vicinal diol product 2 is selectively dehydrated in an ionic liquid solvent under the action of an acid catalyst B to generate a bicyclic conjugated diene 3; In the third step, the bicyclic conjugated diene 3 undergoes a DA cycloaddition reaction with p-benzoquinone 4 under catalyst-free and solvent-free conditions to generate a high-density multicyclic aviation fuel precursor 5; In the fourth step, the high-density polycyclic aviation fuel precursor 5 is hydrodeoxygenated under the catalysis of a supported catalyst or under the co-catalysis of Metal / C and a solid acid catalyst to obtain a high-density polycyclic aviation fuel 6.

2. The method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the first step, the acid catalyst A is selected from one or two of the following catalysts: HgCl2, TiCl4, and the reducing metal is selected from one or more of the following: Fe, Mg, Al, Zn, Ce.

3. The method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the second step, the acid catalyst B is selected from one or more of the following catalysts: AlCl3, FeCl3, Sc(OTf)3, Nafion, MMT, MMT-KSF, MMT K-10, T-62MP, Amberlyst-36, Amberlyst-15, Fe(OTf)3, Al(OTf)3, ZnCl2, Zn(OTf)2, HPW, HPMo, FeCl2, CuCl, CeCl3, La(OTf)3, Ca(NTf2)2, B(C6F5)3, Nb2O5, ZrPO, ZrO2, TSA, H2SO4, TFA, MSA; wherein the ratio of the mass of the acid catalyst B to the mass of the vicinal diol is between 0.01 and 1.

4. The method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the second step, the ionic liquid is one or more of the following: 1,3-dimethylimidazolium dimethyl phosphate ([Mmim][Me2PO4]), 1-ethyl-3-methylimidazolium fluoride ([Emim][F]), 1-ethyl-3-methylimidazolium chloride ([Emim][Cl]), 1-ethyl-3-methylimidazolium bromide ([Emim][Br]), 1-ethyl-3-methylimidazolium hydrogen sulfate ([Emim][HSO4]), 1-ethyl-3 -Methylimidazolium acetate ([Emim][OAc]), 1-ethyl-3-methylimidazolium tetrafluoroborate ([Emim][BF4]), 1-ethyl-3-methylimidazolium thiocyanate ([Emim][SCN]), 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Emim][NTf2]), 1-ethyl-3-methylimidazolium dimethyl phosphate ([Emim][(MeO)2PO2]), 1-ethyl-3-methylimidazolium dicyanamide [Emim][DCA], 1-ethyl-3-methylimidazolium ethyl sulfate ([Emim][EtOSO3]), 1-ethyl-3-methylimidazolium toluenesulfonate ([Emim][Tos]), 1-ethyl-3-methylimidazolium diethyl phosphate [Emim][(EtO)2PO2], 1-butyl-3-methylimidazolium dicyanamide ([Bmim][DCA]), 1-butyl-3-methylimidazolium chloride ([Bmim][DCA]), mim][Cl]), 1-butyl-3-methylimidazolium methanesulfonate ([Bmim][MeSO4]), 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim][BF4]), 1-butyl-3-methylimidazolium hexafluorophosphate ([Bmim][PF6]), 1-hexyl-3-methylimidazolium hydrogen sulfate ([Hmim][HSO4]); N-butylpyridinium nitrate ([BPy][NO3]), N-butyl Pyridine bis(trifluoromethanesulfonyl)imide ([BPy][TFSI]), N-butylpyridine bis(trifluoromethanesulfonyl)imide ([BPy][NTf2]), N-hexylpyridinium nitrate ([HPy][NO3]), N-octylpyridinium nitrate ([OPy][NO3]), N-ethylpyridinium tetrafluoroborate ([EPy][BF4]), N-ethylpyridinium hexafluorophosphate ([EPy][PF6]), N-butylpyridinium bis(trifluoromethanesulfonyl)imide ([BPy][NTf2]), N-hexylpyridinium nitrate ([HPy][NO3]), N-octylpyridinium nitrate ([OPy][NO3]), N-ethylpyridinium tetrafluoroborate ([EPy][BF4]), N-ethylpyridinium hexafluorophosphate ([EPy][PF6]), 1-butyl-1-methylpyrrole thiocyanate ([BMPy][SCN]); 1-butyl-1-methylpyrrole trifluoroacetate ([BMPyrr][TFA]); 1-butyl-1-methylpyrrole dicyanamide ([BMPyrr][DCA]), 1-methyl-1-ethylpyrrole dicyanamide ([EMPyrr][DCA]), 1-hexyl-1-methylpyrrole thiocyanate ([HMPyrr][SCN]), 1-octyl-1-methylpyrrole thiocyanate [OMPyrr][SCN]; choline chloride / succinic acid (ChCl / succinic acid), choline chloride / glycerol (ChCl / glycerol), choline chloride / citric acid (ChCl / citric acid), choline chloride / lactic acid (ChCl / lactic acid), choline chloride / adipic acid (ChCl / adipic acid), choline chloride / malonic acid (ChCl / malonic acid) acid), choline chloride / urea (ChCl / urea), choline chloride / ethylene glycol (ChCl / EG), choline chloride / p-toluenesulfonic acid (ChCl / pTSA), ChCl / 2ZnCl2, ChCl / 2FeCl3, ChCl / 2SnCl2; wherein the amount of the ionic liquid is between 0.5 and 5 times the mass of the vicinal diol product.

5. The method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the first step, the selected solvent is ether or tetrahydrofuran, the reaction temperature is 40-70° C., the reaction time is 12-18 h, and the substrate concentration range is 0.1-1 mol / L.

6. The method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the second step, the reaction temperature is 100-140°C and the reaction time is 2-8h.

7. The method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the third step, the reaction temperature is 40-80°C and the reaction time is 0.5-2h; the molar ratio of the bicyclic conjugated diene 3 to the p-benzoquinone 4 is 1:1 to 2:

1.

8. A method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the fourth step, the carrier in the supported catalyst is one or more of Amberlyst-15, Amberlyst-36, Nafion membrane, HY, H-ZSM-5, H-Beta, H-MOR, and H-SAPO-34, the active metal is one or more of Ni, Cu, Fe, Au, Pd, Pt, Ru, Rh, and Ir, and the metal mass loading is 3-8%; or in the hydrodeoxygenation catalyst, Metal / C is one or more of Pt / C, Pd / C, Ru / C, Ir / C, Rh / C, Co / C, Ni / C, and Fe / C, and the solid acid catalyst is one or more of Amberlyst-15, Amberlyst-36, Nafion membrane, HY, H-ZSM-5, H-Beta, H-MOR, and H-SAPO-34; wherein the ratio of the amount of the catalyst to the mass of the multi-ring aviation fuel precursor 5 is between 0.01 and 0.

3.

9. A method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the fourth step, the solvent used is selected from one or more of cyclohexane, propylene carbonate, methanol, propanol, isopropanol, acetonitrile, tridecane, toluene, tetrahydrofuran, N,N-dimethylformamide, and n-hexane, and the substrate concentration range is 0.01-1 mol / L.

10. A method for preparing high-density multi-ring aviation fuel from biomass platform compounds according to claim 1, characterized in that: In the fourth step, the hydrodeoxygenation reaction is carried out in a tank reactor at a temperature of 160-200° C., a reaction time of 12-15 h, and a hydrogen pressure of 3-5 MPa.

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