A kind of furan structure-containing diene compound and preparation method thereof

Abstract

The present invention discloses a furan structure-containing diene compound and a preparation method thereof, and belongs to the technical field of polymer material synthesis. The furan structure-containing diene compound has a structure shown in formula (I). 2 Selected from C3~C 50 One or more of a straight chain or branched olefin group, a 3-8-membered cycloolefin group, an aromatic group or a heteroaromatic group containing an olefin substituent. The furan structure-containing diene compound of the present invention is a potential monomer of a furan-based polymer material, which is of great significance for solving the limitations of the types of monomers of furan-based polymer materials. The furan structure-containing diene compound of the present invention can be prepared by olefin metathesis polymerization to obtain a furan-based polyester compound, which provides a new idea for the synthesis of furan-based polyester compounds and enriches the structural types of furan-based polyester compounds.

Description

Technical Field

[0001] The invention relates to the technical field of polymer material synthesis, and in particular to a furan structure-containing diene compound and a preparation method thereof. Background Art

[0002] Polymers have been widely used in industry, medicine, daily life and other fields due to their excellent performance and low cost. However, due to their extremely stable chemical and biological properties, they also bring about increasing environmental pollution problems. Compared with traditional petroleum-based raw materials, biomass resources are green and renewable, and are a very meaningful alternative resource for development. Among them, biomass-based polymers, as a polymer material with great biodegradability potential, are expected to achieve sustainable development of polymer materials.

[0003] At present, furan biomass-based polymers can be used in almost all aspects of human production and life, such as clothing, building materials, electronics, automobiles, and daily necessities. Among them, furan-based polyester compounds have very broad application prospects due to their excellent mechanical, heat-resistant, and barrier properties. However, furan-based polyester compounds are usually obtained by polymerization of furan-2,5-dicarboxylic acid and various diols, resulting in a single structure type of furan-based polyester compounds, which limits the application of furan-based polyester compounds. Therefore, it is very important to study and develop a new monomer of furan-based polymer materials for the synthesis of furan-based polyester compounds. Summary of the invention

[0004] In view of this, the technical problem to be solved by the present invention is to provide a furan structure-containing diene compound and a preparation method thereof. The furan structure-containing diene compound of the present invention can be used as a monomer of a furan-based polymer material to generate a furan-based polyester compound through olefin metathesis polymerization, thereby enriching the structural types of the furan-based polyester compound.

[0005] In order to achieve the above purpose, the technical solution adopted by the present invention is as follows:

[0006] The present invention provides a furan-containing diene compound having a structure shown in formula (I):

[0007]

[0008] Preferably, the R 2 Selected from C3~C 50 One or more of a straight chain or branched olefin group, a 3- to 8-membered cycloolefin group, an aryl group or a heteroaryl group containing an olefin substituent.

[0009] C3~C 50 The straight chain or branched olefin group is more preferably C4 to C 18 A straight chain or branched olefin group, more preferably C4 to C11 Straight chain or branched olefin group. In the specific embodiment of the present invention, it can be 2-butenyl, 3-butenyl, 9-decenyl, 10-undecenyl.

[0010] The 3- to 8-membered cycloolefin group is preferably a 5- to 6-membered cycloolefin group, and specifically may be a 2-cyclopentenyl group, a 3-cyclopentenyl group, a 2-cyclohexenyl group, or a 3-cyclohexenyl group.

[0011] In the aryl or heteroaryl containing olefin substituents, the aryl is preferably phenyl. The heteroaryl is preferably one or more of pyridyl, furyl, thienyl, pyrrolyl, pyranyl, pyrimidinyl. In a specific embodiment of the present invention, the aryl containing olefin substituents is selected from methoxy and allyl meta-substituted phenyl.

[0012] The double bond in the above olefin group may be located at a terminal position or in the middle of the chain.

[0013] Preferably, the substituent of the aryl or heteroaryl group containing an olefin substituent further includes one or more of an alkoxy group, an alkyl group, and a halogen group.

[0014] The alkoxy group preferably has 1 to 10 carbon atoms.

[0015] The alkyl group preferably has 1 to 10 carbon atoms.

[0016] Preferably, the olefin substituent is selected from C3-C8 straight-chain or branched olefin groups; more preferably, it is allyl or butyl; further preferably, it is allyl.

[0017] In some specific embodiments of the present invention, the R 2 Selected from the following residues after losing the hydroxyl group:

[0018]

[0019] The present invention also provides a method for preparing a furan-containing diene compound, comprising the following steps: reacting a furan-containing biomass-based compound shown in Formula 1 with an olefin-containing alcohol compound shown in Formula 2 under the action of a catalyst to obtain a furan-containing diene compound shown in Formula (I);

[0020] Formula 1:

[0021] Formula 2:

[0022] Formula (I):

[0023] Preferably, the R 1 One or more selected from -OH, -Cl, -OR.

[0024] Preferably, the R is selected from C1-C5 straight chain or branched alkyl groups.

[0025] Preferably, the R 2 Selected from C3~C 50 One or more of a straight chain or branched olefin group, a 3- to 8-membered cycloolefin group, an aryl group or a heteroaryl group containing an olefin substituent.

[0026] The above R 2 The more preferred and further preferred ranges are the same as above and will not be repeated here.

[0027] Preferably, the formula 2 includes but is not limited to the following structure:

[0028]

[0029] Preferably, in the present invention, the molar ratio of the furan biomass-based compound to the olefin-containing alcohol compound is 1:(2-4); more preferably 1:(2.5-3); further preferably 1:2.5 or 1:3.

[0030] Preferably, the catalyst is selected from one or more of pyridine, 4-dimethylaminopyridine, sodium hydroxide, triethylamine and cerium oxide.

[0031] Preferably, the molar ratio of the catalyst 4-dimethylaminopyridine to the furan-based biomass compound is (5-10):100; more preferably (5-8):100; further preferably 5:100.

[0032] Preferably, the molar ratio of the catalyst pyridine, sodium hydroxide or triethylamine and the furan biomass-based compound is (4-5):1.

[0033] Preferably, the molar ratio of the catalyst cerium oxide to the furanic biomass-based compound is (2-10):100; more preferably (2-5):100; further preferably 3:100.

[0034] Preferably, the solvent of the reaction is selected from one or more of dichloromethane, N,N-dimethylformamide, chloroform and toluene.

[0035] Or when R in Formula 1 1 Selected from -OR, that is, when the furanic biomass-based compound is an ester compound, the olefin-containing alcohol compound in the system is used as both a reactant and a reaction solvent. At this time, the amount of the olefin-containing alcohol compound will be appropriately increased, preferably 20 to 50 times the equivalent of the furanic biomass-based compound.

[0036] Preferably, the reaction temperature is 0 to 160° C. In the present invention, when the reaction raw material is furan-2,5-dicarboxylic acid or furan-2,5-dicarboxylic acid chloride, the reaction temperature is room temperature; if the reaction raw material is furan-2,5-dicarboxylic acid dimethyl ester, the reaction is carried out under reflux at 160° C.

[0037] Preferably, the reaction time is 15 to 48 hours.

[0038] Preferably, the reaction is carried out under a protective gas atmosphere;

[0039] Preferably, the protective gas includes nitrogen or an inert gas.

[0040] The method for preparing the furan structure-containing diene compound of the present invention specifically comprises the following steps:

[0041]

[0042] (I) The raw material is furan-2,5-dicarboxylic acid:

[0043] 1) mixing furan-2,5-dicarboxylic acid, an olefin-containing alcohol compound, and a solvent, and stirring the mixture in an ice bath to obtain a mixed system;

[0044] 2) Add DMAP and EDC to the above mixed system in sequence and react at room temperature for 20 to 30 hours. After the reaction is completed, add dilute hydrochloric acid to the reaction bottle and stir for 0.5 to 1 hour. Then extract with dichloromethane and water, dry the organic phase and remove the solvent by vacuum distillation to obtain a crude product, which is then separated by column to obtain a pure product.

[0045] Among them, the molar ratio of furan-2,5-dicarboxylic acid to the olefin-containing alcohol compound is 1:2.5, the molar ratio of DMAP to furan-2,5-dicarboxylic acid is 5:100, and the molar ratio of EDC to furan-2,5-dicarboxylic acid is 2.4:1. The addition of EDC promotes the forward progress of the esterification reaction.

[0046] (ii) The raw material is furan-2,5-dicarbonyl chloride:

[0047] 1) mixing an olefin-containing alcohol compound, a solvent, and pyridine, and stirring the mixture in an ice bath to obtain a mixed system;

[0048] 2) Add furan-2,5-dicarbonyl chloride and DMAP to the above mixed system in sequence and react at room temperature for 20 to 30 hours. After the reaction is completed, add dilute hydrochloric acid to the reaction bottle and stir for 0.5 to 1 hour. Then extract with dichloromethane and water, dry the organic phase and remove the solvent by vacuum distillation to obtain a crude product, which is then separated by column to obtain a pure product.

[0049] The molar ratio of furan-2,5-dicarbonyl chloride to the olefin-containing alcohol compound is 1:3, the molar ratio of pyridine to furan-2,5-dicarbonyl chloride is 4:1, and the molar ratio of DMAP to furan-2,5-dicarbonyl chloride is 5:100. Pyridine is used as an acid binding agent to absorb the reaction by-product hydrogen chloride, promote the esterification reaction to proceed in the forward direction, and improve the product yield.

[0050] (III) The raw material is dimethyl furan-2,5-dicarboxylate:

[0051] Cerium oxide was added to the reaction flask and stirred, and then the olefin-containing alcohol compound and furan-2,5-dimethyl ester were added in sequence, and the reaction flask was placed at 160°C for reflux reaction for 15 to 48 hours. After the reaction was completed, dichloromethane and water were used for extraction, and the organic phase was dried and then distilled under reduced pressure to remove the solvent to obtain a crude product, which was then separated by column to obtain a pure product.

[0052] In the above-mentioned transesterification reaction, the olefin-containing alcohol compound serves as both a reactant and a solvent; the molar ratio of furan-2,5-dimethyl ester to the olefin-containing alcohol compound is 1:(20-50), and the molar ratio of cerium oxide to furan-2,5-dimethyl ester is 3:100.

[0053] The furan structure-containing diene compound of the present invention can also be used to prepare furan-based polyester compounds, which provides a new idea for the synthesis method of furan-based polyester compounds and enriches the monomer types of furan-based polymer materials.

[0054] Compared with the prior art, the furan structure-containing diene compound of the present invention has a structure shown in formula (I). 2 Selected from C3~C 50 One or more of a straight chain or branched olefin group, a 3-8 membered cycloolefin group, an aryl group or a heteroaryl group containing an olefin substituent. The furan structure-containing diene compound of the present invention is a potential monomer for furan-based polymer materials, which is of great significance for solving the limitations of the types of furan-based polymer material monomers. The furan structure-containing diene compound of the present invention can be prepared into a furan-based polyester compound by olefin metathesis polymerization, which provides a new idea for the synthesis of furan-based polyester compounds and enriches the structural types of furan-based polyester compounds. In addition, the furan structure-containing diene compound also has potential application value in the fields of flavors and fragrances, material modification, etc. BRIEF DESCRIPTION OF THE DRAWINGS

[0055] Figure 1 Furan-2,5-dicarboxylic acid di(3-butylene) ester 1 H NMR spectra;

[0056] Figure 2 Furan-2,5-dicarboxylic acid di(3-butylene) ester 13C NMR spectra;

[0057] Figure 3 Furan-2,5-dicarboxylic acid di(10-undecene) ester 1 H NMR spectra;

[0058] Figure 4 Furan-2,5-dicarboxylic acid di(10-undecene) ester 13 C NMR spectra;

[0059] Figure 5 Di(3-cyclopentyl)furan-2,5-dicarboxylate 1 H NMR spectra;

[0060] Figure 6 Furan-2,5-dicarboxylic acid di-eugenol ester 1 H NMR spectra;

[0061] Figure 7 Furan-2,5-dicarboxylic acid di-eugenol ester 13 C NMR spectra;

[0062] Figure 8 Furan-2,5-dicarboxylic acid di(9-decenyl) ester 1 H NMR spectra;

[0063] Fig. 9 Furan-2,5-dicarboxylic acid di(9-decenyl) ester 13 C NMR spectra;

[0064] Fig.10 Furan-2,5-dicarboxylic acid di(crotyl alcohol) ester 1 H NMR spectra;

[0065] Fig.11 Furan-2,5-dicarboxylic acid di(crotyl alcohol) ester 13 C NMR spectra;

[0066] Fig.12 is a furanyl polyester compound (b) 1 H NMR spectra;

[0067] Fig.13 is a furanyl polyester compound (b) 13 C NMR spectrum. DETAILED DESCRIPTION

[0068] In order to further illustrate the present invention, the furan structure-containing diene compound and the preparation method thereof provided by the present invention are described in detail below in conjunction with examples.

[0069] The substrate materials, solvents, etc. involved in the following examples are all commercial products (analytical grade reagents) and are not further purified.

[0070] 1 H NMR (400 MHz), 13 C NMR (101 MHz), CDCl3 was used as deuterated solvent and TMS was used as internal standard.

[0071] Multiplicities are defined as follows: s (singlet); d (doublet); t (triplet); q (quartet) and m (multiplet). Coupling constant J (hertz).

[0072] Example 1

[0073] Synthesis of Di(3-Butyl)-2,5-Furan Dicarboxylate

[0074]

[0075] Add a magnetic stirrer to the reaction flask and pump Ar gas three times. Place the reaction flask in an ice bath and add solvent dichloromethane, 3-butene-1-ol (7.75 mL, 3.0 eq), and pyridine (9.65 mL, 4.0 eq). Then add furan-2,5-dicarbonyl chloride (5.76 g, 30 mmol, 1.0 eq) and DMAP (0.2 g, 1.5 mmol, 0.05 eq) to the reaction flask in sequence, then move the reaction flask to room temperature and react for 20 to 30 hours.

[0076] After the reaction is completed, dilute hydrochloric acid is added to the reaction flask and stirred for 0.5 to 1 hour. The mixture is extracted three times with dichloromethane and water, and the organic phase is dried over anhydrous sodium sulfate and the solvent is removed by vacuum distillation. The obtained crude product is separated by column to obtain a pure product with a yield of 90% and a purity of 99%.

[0077] NMR characterization: 1 H NMR (400MHz, Chloroform-d) δ7.17 (s, 2H), 5.82 (ddt, J=17.0, 10.2, 6.8Hz, 2H), 5.14 (dq, J=17. 2, 1.6Hz, 2H), 5.09 (dq, J=10.2, 1.2Hz, 2H), 4.37 (t, J=6.8Hz, 4H), 2.50 (qt, J=6.8, 1.3Hz, 4H);

[0078] 13 C NMR (101MHz, Chloroform-d) δ 157.86, 146.70, 133.35, 118.25, 117.59, 64.38, 32.91.

[0079] Example 2

[0080] Synthesis of Di(10-Undecene) Furan-2,5-dicarboxylate

[0081]

[0082] Add a magnetic stirrer to the reaction flask and pump Ar gas three times. Place the reaction flask in an ice bath, add solvent dichloromethane, 10-undecene-1-ol (36.4 mL, 3.0 eq), and pyridine (19.0 mL, 4.0 eq). Then add furan-2,5-dicarbonyl chloride (11.4 g, 60 mmol, 1.0 eq) and DMAP (0.4 g, 3.0 mmol, 0.05 eq) to the reaction flask in sequence, and then move the reaction flask to room temperature and react for 20 to 30 hours.

[0083] After the reaction is completed, dilute hydrochloric acid is added to the reaction flask and stirred for 0.5 to 1 hour. The mixture is extracted three times with dichloromethane and water, and the organic phase is dried over anhydrous sodium sulfate, and the solvent is removed by vacuum distillation. The obtained crude product is separated by column to obtain a pure product with a yield of 92% and a purity of 99%.

[0084] NMR characterization: 1 H NMR (400MHz, Chloroform-d) δ7.18 (s, 2H), 5.80 (ddt, J=16.9, 10.1, 6.7Hz, 2H), 5.02-4.95 (m, 4H), 4.92 ( d, J=10.2Hz, 4H), 4.32 (t, J=6.8Hz, 4H), 2.03 (q, J=7.1Hz, 4H), 1.75 (p, J=6.9Hz, 3H), 1.46-1.21 (m, 28H);

[0085] 13 C NMR (101MHz, Chloroform-d) δ 158.19, 146.95, 139.19, 118.20, 114.14, 65.71, 33.81, 29.44, 29.39, 29.21, 29.10, 28.91, 28.60, 25.84.

[0086] Example 3

[0087] Synthesis of Di(3-cyclopentenyl)furan-2,5-dicarboxylate

[0088]

[0089] Add a magnetic stirrer to the reaction flask and pump Ar gas three times. Place the reaction flask in an ice bath and add solvent dichloromethane, 3-cyclopentene-1-ol (7.12 mL, 3.0 eq), and pyridine (9.65 mL, 4.0 eq). Then add furan-2,5-dicarbonyl chloride (5.76 g, 30 mmol, 1.0 eq) and DMAP (0.2 g, 1.5 mmol, 0.05 eq) to the reaction flask in sequence, and then move the reaction flask to room temperature and react for 20 to 30 hours.

[0090] After the reaction is completed, dilute hydrochloric acid is added to the reaction flask and stirred for 0.5 to 1 hour. The mixture is extracted three times with dichloromethane and water, and the organic phase is dried over anhydrous sodium sulfate, and the solvent is removed by vacuum distillation. The obtained crude product is separated by column to obtain a pure product with a yield of 77% and a purity of 99%.

[0091] NMR characterization: 1 H NMR (400MHz, Chloroform-d) δ7.16 (s, 2H), 5.75 (s, 4H), 5.60 (tt, J=7.0, 2.6Hz, 2H), 2.84 (dd, J=16.7, 7.0Hz, 4H), 2.55 (dd, J=16.6, 2.3Hz, 4H).

[0092] Example 4

[0093] Synthesis of Di(eugenol)furan-2,5-dicarboxylate

[0094]

[0095] Add furan-2,5-dicarboxylic acid (4.68 g, 30 mmol, 1.0 eq) and a magnetic stirrer into the reaction flask, and pump and fill with Ar gas three times. Place the reaction flask in an ice bath, add solvent dichloromethane and eugenol (11.5 mL, 2.5 eq). Then add DMAP (0.2 g, 1.5 mmol, 0.05 eq) and EDC (13.8 g, 2.4 eq) into the reaction flask in sequence, and then move the reaction flask to room temperature and react for 20 to 30 hours.

[0096] After the reaction is completed, dilute hydrochloric acid is added to the reaction flask and stirred for 0.5 to 1 hour. The mixture is extracted three times with dichloromethane and water, and the organic phase is dried over anhydrous sodium sulfate, and the solvent is removed by vacuum distillation. The obtained crude product is separated by a column to obtain a pure product with a yield of 70% and a purity of 99%.

[0097] NMR characterization: 1H NMR (400MHz, Chloroform-d) δ7.46 (s, 2H), 7.07 (d, J=8.0Hz, 2H), 6.88-6.71 (m, 4H), 5.9 8 (ddt, J=16.9, 10.1, 6.7Hz, 2H), 5.18-5.05 (m, 4H), 3.82 (s, 6H), 3.40 (d, J=6.7Hz, 4H);

[0098] 13 C NMR (101MHz, Chloroform-d) δ 155.82, 150.75, 146.54, 139.53, 137.06, 136.87, 122.32, 120.67, 119.75, 116.22, 112.76, 55.78, 40.05.

[0099] Example 5

[0100] Di(9-decenyl)furan-2,5-dicarboxylate

[0101]

[0102] Add a magnetic stirrer to the reaction flask and pump Ar gas three times. Place the reaction flask in an ice bath and add solvent dichloromethane, 9-decene-1-ol (3.0 eq), and pyridine (19.0 mL, 4.0 eq). Then add furan-2,5-dicarbonyl chloride (11.4 g, 60 mmol, 1.0 eq) and DMAP (0.4 g, 3.0 mmol, 0.05 eq) to the reaction flask in sequence, then move the reaction flask to room temperature and react for 20 to 30 hours.

[0103] After the reaction is completed, dilute hydrochloric acid is added to the reaction flask and stirred for 0.5 to 1 hour. The mixture is extracted with dichloromethane and water three times, the organic phase is dried over anhydrous sodium sulfate, and the solvent is removed by vacuum distillation to obtain a crude product, which is separated by a column to obtain a pure product with a yield of 91% and a purity of 99%.

[0104] NMR characterization: 1 H NMR (400MHz, Chloroform-d) δ7.17 (s, 2H), 5.78 (ddt, J=16.9, 10.2, 6.7Hz, 2H), 4.97 (dd, J=17.1, 2.0Hz, 2H) , 4.93-4.88 (m, 2H), 4.30 (t, J=6.8Hz, 4H), 2.02 (q, J=7.0Hz, 4H), 1.73 (p, J=6.8Hz, 4H), 1.46-1.18 (m, 20H);

[0105] 13C NMR (101MHz, Chloroform-d) δ 158.05, 146.82, 138.99, 118.09, 114.07, 65.56, 33.67, 29.21, 29.05, 28.91, 28.76, 28.47, 25.71.

[0106] Example 6

[0107] Furan-2,5-dicarboxylic acid di(crotyl alcohol) ester

[0108]

[0109] Add a magnetic stirrer to the reaction flask and pump Ar gas three times. Place the reaction flask in an ice bath and add solvents such as dichloromethane, crotyl alcohol (3.0 eq), and pyridine (19.0 mL, 4.0 eq). Then add furan-2,5-dicarbonyl chloride (11.4 g, 60 mmol, 1.0 eq) and DMAP (0.4 g, 3.0 mmol, 0.05 eq) to the reaction flask in sequence, and then move the reaction flask to room temperature and react for 20 to 30 hours.

[0110] After the reaction is completed, dilute hydrochloric acid is added to the reaction flask and stirred for 0.5 to 1 hour. The mixture is extracted with dichloromethane and water three times, the organic phase is dried over anhydrous sodium sulfate, and the solvent is removed by vacuum distillation to obtain a crude product, which is separated by a column to obtain a pure product with a yield of 85% and a purity of 99%.

[0111] NMR characterization: 1 H NMR (400MHz, Chloroform-d) δ7.19 (s, 2H), 5.93-5.82 (m, 2H), 5.71-5.63 (m, 2H), 4.75 (dt, J=6.6, 1.0Hz, 4H), 1.74 (dq, J=6.5, 1.0Hz, 6H);

[0112] 13 C NMR (101MHz, Chloroform-d) δ157.81, 146.77, 132.51, 124.32, 118.30, 66.11, 17.74.

[0113] Application Example 1

[0114] Synthesis of Furan-based Polyester Compounds

[0115] After adding 1g of furan-containing diene monomer (a), 2mg of Grubbs I catalyst and magnetic stirrer into the reaction tube, the reaction tube is sealed and evacuated. Heat and stir at 50°C, and react for 2 to 18 hours until the reaction liquid changes from a molten state to a solid; then raise the temperature to 80°C, heat and stir, and react for 2 to 24 hours until no bubbles emerge in the system; then raise the temperature to 120°C, heat and stir, and react for 2 to 48 hours until basically no bubbles are generated; the stirring rate is controlled at 50 to 850 r / min during the entire reaction process. The obtained reaction liquid is cooled to room temperature, methanol is added for washing, and then methanol is used for suction filtration and washing, and the solvent is removed to obtain a slightly yellow solid, i.e., a furan-based polyester compound (b) containing an olefin structure, with a yield of 74%.

[0116]

[0117] 1 H NMR (400MHz, Chloroform-d) δ7.19 (s, 2H), 5.33-5.39 (m, 2H), 4.32 (t, J=6.8Hz, 4H), 2.08-1.91 (m, 4H), 1.75 (p, J=6.8Hz, 4H), 1.45-1.18 (m, 24H).

[0118] 13 C NMR (101MHz, Chloroform-d) δ158.2, 146.9, 130.3, 118.2, 65.7, 32.6, 29.7, 29.5, 29.4, 29.3, 29.2, 28.6, 27.2, 25.9.

[0119] In summary, the present invention reacts furan-2,5-dicarboxylic acid (or acid chloride, ester) with an olefin-containing alcohol compound to obtain a furan structure-containing diene compound, which can be used as a furan-based polymer material monomer to prepare a furan-based polyester compound through olefin metathesis polymerization. This not only enriches the structural types of furan-based polyester compounds, but also provides a new idea for the synthesis of furan-based polymers.

[0120] The above embodiments are only used to help understand the method and core idea of ​​the present invention. It should be noted that, for those skilled in the art, several improvements and modifications can be made to the present invention without departing from the principles of the present invention, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims

1. A furan-based polyester compound, which is prepared by olefin metathesis polymerization using a furan-containing diene compound represented by formula (I) as a polymerization monomer; The R 2 Selected from C3~C 50 Straight chain or branched olefin group.

2. The furan-based polyester compound according to claim 1, characterized in that The method for preparing the furan-containing diene compound comprises the following steps: reacting the furan-containing biomass-based compound shown in Formula 1 with the olefin-containing alcohol compound shown in Formula 2 under the action of a catalyst to obtain the furan-containing diene compound shown in Formula (I); The R 1 One or more selected from -OH, -Cl, -OR; The R is selected from C1-C5 straight chain or branched alkyl; The R 2 Selected from C3~C 50 Straight chain or branched olefin group.

3. The furan-based polyester compound according to claim 2, characterized in that The molar ratio of the furan biomass-based compound to the olefin-containing alcohol compound is 1:(2-4).

4. The furan-based polyester compound according to claim 2, characterized in that The catalyst is selected from one or more of pyridine, 4-dimethylaminopyridine, sodium hydroxide, triethylamine and cerium oxide.

5. The furan-based polyester compound according to claim 4, characterized in that The molar ratio of the catalyst 4-dimethylaminopyridine to the furan biomass-based compound is (5-10):100; The molar ratio of the catalyst pyridine, sodium hydroxide or triethylamine and the furan biomass-based compound is (4-5):1; The molar ratio of the catalyst cerium oxide to the furan biomass-based compound is (2-10):

100.

6. The furan-based polyester compound according to claim 2, characterized in that: The solvent of the reaction is selected from one or more of dichloromethane, N,N-dimethylformamide, chloroform, and toluene; Or when R in Formula 1 1 When selected from -OR, the olefin-containing alcohol compound in the system serves as both a reactant and a reaction solvent; The molar ratio of the olefin-containing alcohol compound to the furan biomass-based compound is (20-50):

1.

7. The furan-based polyester compound according to claim 2, characterized in that: The reaction temperature is 0 to 160°C; The reaction time is 15 to 48 hours.

8. The furan-based polyester compound according to claim 2, characterized in that: The reaction is carried out under a protective gas atmosphere; The protective gas includes nitrogen or an inert gas.

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