Di (propyl-2-alkenyl) furan-2, 5-dicarboxylate and preparation method thereof

By using an inorganic metal catalyst under an inert atmosphere, the preparation cost and reaction time of di(propyl-2-alkenyl)furan-2,5-dicarboxylic acid ester are successfully reduced, and the high-quality in the prior art is solved The cost and environmental pollution issues have achieved an efficient and environmentally friendly production process.

CN119161314AActive Publication Date: 2024-12-20SHAANXI UNIV OF SCI & TECH
View PDF 3 Cites 0 Cited by

Patent Information

Application Number
CN202411301483.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-09-18
Publication Date
2024-12-20
Estimated Expiration
2044-09-18

AI Technical Summary

Technical Problem

The existing synthetic bis(propyl-2-enyl)furan-2,5-dicarboxylic acid ester process has high preparation cost, long reaction time, and the use of toxic and harmful reagents has led to environmental pollution.

Method used

Hydroxide, 2,5-furandicarboxylic acid and solvent were mixed under an inert atmosphere, and allyl compounds were slowly added after adding the catalyst. After stirring, cooling, filtering, washing, recrystallization and vacuum drying, the nitro (C) was obtained. 2-alkenyl)furan-2,5-dicarboxylic acid ester is used to reduce the reaction conditions.

Benefits of technology

It significantly reduces the preparation cost and reaction time, reduces energy consumption and equipment costs, improves product purity and production efficiency, and inorganic metal catalysts are environmentally friendly.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN119161314A_ABST
    Figure CN119161314A_ABST
Patent Text Reader

Abstract

The invention discloses di (propyl-2-alkenyl) furan-2, 5-dicarboxylate and a preparation method thereof, and relates to the technical field of biomass-based organic synthesis methods. According to the method, 2, 5-furandicarboxylic acid is taken as a base material, allyl is grafted on the 2, 5-furandicarboxylic acid through esterification reaction under the action of an inorganic metal catalyst, and the bis (propyl-2-alkenyl) furan-2, 5-dicarboxylate is obtained. Compared with a traditional synthesis method, required reaction conditions are mild, a high-temperature and high-pressure environment is not needed, the energy consumption is reduced, and the operation risk and the equipment cost are also reduced. The mild reaction conditions are more beneficial to keeping the activity and selectivity of the catalyst, and the reaction efficiency is improved. The obtained product is high in purity and can be directly used for subsequent application or further chemical conversion without complicated post-treatment steps, so that the overall production efficiency is improved. The invention provides a new thought for realizing high value-added utilization of biomass materials such as 2, 5-furandicarboxylic acid and the like.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] The invention belongs to the technical field of biomass-based organic synthesis methods, and specifically relates to di(propyl-2-enyl)furan-2,5-dicarboxylate and a preparation method thereof. Background Art

[0002] In order to protect the natural environment and promote sustainable economic development, it is increasingly important to develop renewable resources to replace traditional fossil energy. Biomass resources are a special renewable resource. They are produced by green plants through photosynthesis to convert solar energy into chemical energy and store it in biomass. Biomass resources are widely distributed, have large output, and are renewable. They are considered to be carbon-neutral resources. The carbon dioxide produced in the process of consuming biomass resources will be fixed to biomass again by photosynthesis of plants, achieving zero carbon dioxide emissions and reducing air pollution. Therefore, it is necessary to find natural, renewable, degradable and pollution-free biomass materials in nature to replace traditional fossil energy materials. The twelve high-value bio-based platform compounds produced from sugars through biological or chemical conversion include: 1,4-dicarboxylic acid, 2,5-furandicarboxylic acid, 3-hydroxypropionic acid, aspartic acid, glucaric acid, glutamic acid, itaconic acid, levulinic acid, 3-hydroxybutyrolactone, glycerol, sorbitol and xylitol. Among them, 2,5-furandicarboxylic acid is a high-value-added biological and chemical substance, and it is also the only aromatic bio-based platform compound. In recent years, as a substitute for petrochemical derivative terephthalic acid, it has been used to synthesize high-value polymers and has great market potential.

[0003] Di(propyl-2-enyl)furan-2,5-dicarboxylate, as a biomass-based compound, can be used to synthesize polyester. As a polyester monomer, the structure of di(propyl-2-enyl)furan-2,5-dicarboxylate can improve the mechanical properties, melting point, and creep resistance of the polymer due to the presence of furandicarboxylic acid with an aromatic ring. The polyester synthesized from di(propyl-2-enyl)furan-2,5-dicarboxylate has a unique chemical structure and excellent mechanical properties, and is non-toxic and harmless, which is very consistent with the development requirements of "green chemistry". In the existing process for synthesizing di(propyl-2-enyl)furan-2,5-dicarboxylate, such as patent CN113185694 A, the reaction time is long, the reaction temperature requirement is high, and a large amount of organic reagents are required in the preparation process, the preparation cost is high, and it is not environmentally friendly.

[0004] In view of the problems of high preparation cost, long reaction time and environmental pollution caused by toxic and harmful reagents in the existing process for synthesizing di(propyl-2-enyl)furan-2,5-dicarboxylate, it is urgent to find a new preparation method for di(propyl-2-enyl)furan-2,5-dicarboxylate to reduce the requirements for reaction conditions, simplify the preparation process and reduce the preparation cost. Summary of the invention

[0005] In order to overcome the shortcomings of the above-mentioned prior art, the purpose of the present invention is to provide a di(propyl-2-enyl)furan-2,5-dicarboxylate and a preparation method thereof, so as to solve the problems of high preparation cost, long reaction time and environmental pollution caused by toxic and harmful reagents in the traditional method.

[0006] In order to achieve the above object, the present invention adopts the following technical solutions: The invention discloses a method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate, comprising: First, the hydroxide, 2,5-furandicarboxylic acid and solvent are mixed under an inert atmosphere, stirred and reacted once, and then the temperature is lowered. Then, a catalyst is added and stirred evenly. Subsequently, an allyl compound is slowly added. After a second stirring reaction, the mixture is cooled to room temperature and filtered to obtain a white solid suspended on the upper layer of the reaction solution. Finally, the mixture is washed, rotary evaporated, recrystallized, filtered and vacuum dried to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate.

[0007] Preferably, the mass ratio of hydroxide, 2,5-furandicarboxylic acid, solvent, catalyst and allyl compound is (5-10):(10-20):(50-100):(0.4-0.8):(10-30).

[0008] Further preferably, the mass ratio of the solvent to the hydroxide is 20:(1-2); the mass ratio of 2,5-furandicarboxylic acid to the hydroxide is 2:(1-1.5); the mass ratio of the catalyst to 2,5-furandicarboxylic acid is 1:(12.5-25); and the mass ratio of the allyl compound to 2,5-furandicarboxylic acid is (1.2-2.4):1.

[0009] Preferably, the inert atmosphere is N2; the temperature of a stirring reaction is 60-80°C, and the time of a stirring reaction is 3-6 hours; after cooling to 40-70°C, a catalyst is added.

[0010] Preferably, the conditions for the secondary stirring reaction are: stirring the reaction for 3 to 6 hours under condensation reflux conditions.

[0011] Preferably, the hydroxide is sodium hydroxide or potassium hydroxide; the solvent is at least one of water, methanol, ethanol and N,N-dimethylformamide; and the catalyst is at least one of ferric chloride, ferric chloride, aluminum chloride, cupric chloride, cuprous chloride, potassium chloride and cuprous bromide.

[0012] Preferably, the allyl compound is at least one of allyl chloride and allyl bromide.

[0013] Preferably, the time for slowly adding the allyl compound is controlled within 30 to 60 minutes.

[0014] Preferably, the organic solvent for recrystallization is at least one of methanol, ethanol, n-hexane, cyclohexane, toluene, chloroform and tetrahydrofuran.

[0015] The present invention also discloses a di(propyl-2-enyl)furan-2,5-dicarboxylate, which is prepared by the above-mentioned preparation method and has the structural formula: .

[0016] Compared with the prior art, the present invention has the following beneficial effects: The invention discloses a method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate. The method uses 2,5-furandicarboxylic acid as a basic material, and grafts allyl groups onto 2,5-furandicarboxylic acid under the action of an inorganic metal catalyst through an esterification reaction to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate. The reaction conditions are relatively low, high temperature and high pressure are not required, the preparation process is simple and convenient, no side reactions are generated, the product purity is high, and the preparation cost can be greatly reduced. Compared with traditional organic synthesis reactions, the reaction conditions required by the invention are relatively mild, and a high temperature and high pressure environment is not required, which not only reduces energy consumption, but also reduces operating risks and equipment costs. Mild reaction conditions are also more conducive to maintaining the activity and selectivity of the catalyst and improving the reaction efficiency. The inorganic metal catalyst is used, while promoting the esterification reaction, it exhibits good stability and recyclability, reduces the use cost of the catalyst and the burden of waste treatment, and at the same time, the inorganic metal catalyst is generally less toxic and environmentally friendly. The reaction process is simple and precisely controlled, with almost no by-products generated. The obtained di(propyl-2-enyl)furan-2,5-dicarboxylate product has high purity and can be directly used for subsequent applications or further chemical transformation without complicated post-processing steps, thereby improving the overall production efficiency. While ensuring product quality, the costs of raw materials, energy consumption, equipment investment, and waste treatment are significantly reduced, making the production of di(propyl-2-enyl)furan-2,5-dicarboxylate more economical and feasible. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 The present invention discloses a flow chart for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE); Figure 2 FT-IR spectrum of di(propyl-2-enyl)furan-2,5-dicarboxylate disclosed in Example 1 of the present invention; Figure 3 Di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) disclosed in Example 1 of the present invention 1H NMR spectrum. DETAILED DESCRIPTION

[0018] In order to enable those skilled in the art to better understand the scheme of the present invention, the technical scheme in the embodiments of the present invention will be clearly and completely described below in conjunction with the drawings in 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 should fall within the scope of protection of the present invention.

[0019] It should be noted that the terms "first", "second", etc. in the specification and claims of the present invention and the above-mentioned drawings are used to distinguish similar objects, and are not necessarily used to describe a specific order or sequence. It should be understood that the data used in this way can be interchanged where appropriate, so that the embodiments of the present invention described herein can be implemented in an order other than those illustrated or described herein. In addition, the terms "including" and "having" and any variations thereof are intended to cover non-exclusive inclusions, for example, a process, method, system, product or device that includes a series of steps or units is not necessarily limited to those steps or units that are clearly listed, but may include other steps or units that are not clearly listed or inherent to these processes, methods, products or devices.

[0020] The present invention is further described in detail below in conjunction with the accompanying drawings: The invention discloses a method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE), and relates to the technical field of biomass-based organic synthesis methods. The method uses 2,5-furandicarboxylic acid as a basic material, and grafts allyl groups onto 2,5-furandicarboxylic acid under the action of an inorganic metal catalyst through an esterification reaction to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE). The invention provides a new idea for realizing high value-added utilization of biomass materials such as 2,5-furandicarboxylic acid (FDCA).

[0021] The present invention discloses a di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE). The di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) has the following structural formula: .

[0022] The present invention also discloses a method for preparing the above-mentioned di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE), which specifically comprises the following steps: Step 1: Under the protection of N2, take 5-10 parts of sodium hydroxide or potassium hydroxide, 10-20 parts of 2,5-furandicarboxylic acid, and then add 50-100 parts of solvent, slowly heat to 60-80°C and stir to dissolve, and react at 60-80°C for 3-6 hours.

[0023] Step 2: After the reaction temperature of step 1 is cooled to 40-70°C, add 0.4-0.8 parts of catalyst and stir evenly. Take 10-30 parts of allyl compound, slowly dropwise add and stir under condensation reflux conditions. After the dropwise addition is completed, react for 3-6 hours.

[0024] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Take a large amount of water for washing, rotary evaporation, and removal of impurities to obtain a white solid. The white solid is recrystallized in an organic solvent, filtered, and packaged after vacuum drying, and sealed for storage to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE).

[0025] Preferably, in step 1, the solvent is at least one of water, methanol, ethanol and N,N-dimethylformamide, wherein the mass ratio of the solvent to the hydroxide is 20: (1-2).

[0026] The mass ratio of 2,5-furandicarboxylic acid to hydroxide is 2:(1~1.5).

[0027] In step 2, the catalyst is at least one of ferric chloride, ferric chloride, aluminum chloride, cupric chloride, cuprous chloride, potassium chloride and cuprous bromide.

[0028] The mass ratio of the catalyst to 2,5-furandicarboxylic acid is 1:(12.5~25).

[0029] The allyl compound is at least one of allyl chloride and allyl bromide.

[0030] The mass ratio of the allyl compound to 2,5-furandicarboxylic acid is (1.2~2.4):1.

[0031] The time for slowly adding the allyl compound should be controlled within 30 to 60 minutes.

[0032] In step three, in the recrystallization purification step, the organic solvent is at least one of methanol, ethanol, n-hexane, cyclohexane, toluene, chloroform and tetrahydrofuran. Example 1 A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) comprises the following steps: Step 1: Under the protection of N2, take 6 parts of sodium hydroxide and 10 parts of 2,5-furandicarboxylic acid, add 60 parts of water, slowly heat to 80°C and stir to dissolve, and react at 80°C for 3 hours.

[0033] Step 2: After the reaction temperature of step 1 is cooled to 55°C, add 0.4 parts of copper dichloride catalyst and stir evenly. Take 18 parts of propylene bromide and slowly add dropwise for 30 minutes under condensation reflux conditions and stir. After the addition is complete, react for 4 hours.

[0034] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Wash three times with a large amount of water, rotary evaporate, remove impurities, and obtain a white solid. The white solid is recrystallized in n-hexane solvent, filtered, packaged after vacuum drying, and sealed to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) with a yield of 94%.

[0035] See also Figure 1 The present invention discloses a preparation flow chart of di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE). As can be seen from the figure, the preparation process is divided into two steps. The first step is the reaction of 2,5-furandicarboxylic acid with sodium hydroxide to generate sodium alkoxide and water. The second step is the reaction of sodium alkoxide with an allyl compound, and the allyl group is grafted thereon to generate di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE). No other by-products are generated in the entire reaction process, the reaction conditions are relatively mild, high temperature and high pressure are not required, and the process is simple and convenient. Figure 2 This is the FT-IR spectrum of di(propyl-2-enyl)furan-2,5-dicarboxylate disclosed in Example 1 of the present invention. It can be seen from the FT-IR spectrum that compared with FDCA, FDCE has a -1 The corresponding olefinic hydrogen (=CH) stretching vibration absorption peak at 1028 cm -1 and 1288 cm -1 The corresponding ester group (CO) absorption peaks at the bottom of the graphite column indicate the formation of di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE).

[0036] Figure 3 Di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) disclosed in Example 1 of the present invention 1H NMR spectrum; as can be seen from the figure, the chemical shifts δ of 7.34 ppm(1), 5.99 ppm(2), 5.43 ppm(3), 5.32 ppm(4), and 4.84 ppm(5) belong to the hydrogen atomic nuclear magnetic peaks in various locations in FDCE, confirming the successful synthesis of di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE), and the integrated area shows that the purity of the product is very high, about 97%.

[0037] Example 2 A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) comprises the following steps: Step 1: Under the protection of N2, take 10 parts of potassium hydroxide and 15 parts of 2,5-furandicarboxylic acid, add 100 parts of water, slowly heat to 80°C and stir to dissolve, and react at 80°C for 4 hours.

[0038] Step 2: After the reaction temperature of step 1 is cooled to 45°C, add 0.5 parts of catalyst ferric chloride and stir evenly. Take 18 parts of propylene chloride, slowly dropwise add for 30 minutes and stir under condensation reflux conditions. After the dropwise addition is completed, react for 4 hours.

[0039] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Wash three times with a large amount of water, rotary evaporate, remove impurities, and obtain a white solid. Recrystallize the white solid in n-hexane solvent, filter, package it after vacuum drying, and seal it to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) with a yield of 90%.

[0040] Example 3 A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) comprises the following steps: Step 1: Under the protection of N2, take 10 parts of sodium hydroxide, 16 parts of 2,5-furandicarboxylic acid, and then add 80 parts of ethanol, slowly heat to 65°C and stir to dissolve, and react at 65°C for 5 hours.

[0041] Step 2: After the reaction temperature of step 1 is cooled to 55°C, add 0.6 parts of aluminum chloride catalyst and stir evenly. Take 25 parts of propylene bromide and slowly add dropwise for 40 minutes under condensation reflux conditions and stir. After the addition is complete, react for 5 hours.

[0042] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Wash three times with a large amount of water, rotary evaporate, remove impurities, and obtain a white solid. Recrystallize the white solid in an ethanol solvent, filter, package it after vacuum drying, and seal it for storage to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) with a yield of 92%.

[0043] Example 4 A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) comprises the following steps: Step 1: Under the protection of N2, take 5 parts of sodium hydroxide, 10 parts of 2,5-furandicarboxylic acid, and then add 50 parts of methanol, slowly heat to 60°C and stir to dissolve, and react at 60°C for 5 hours.

[0044] Step 2: After the reaction temperature of step 1 is cooled to 45°C, add 0.5 parts of catalyst ferric chloride and stir evenly. Take 20 parts of bromopropylene and slowly dropwise add for 30 minutes under condensation reflux conditions and stir. After the dropwise addition is completed, react for 6 hours.

[0045] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Wash three times with a large amount of water, rotary evaporate, remove impurities, and obtain a white solid. Recrystallize the white solid in cyclohexane solvent, filter, package it after vacuum drying, and seal it to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) with a yield of 90%.

[0046] Example 5 A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) comprises the following steps: Step 1: Under the protection of N2, take 7 parts of sodium hydroxide, 17 parts of 2,5-furandicarboxylic acid, and then add 85 parts of N,N-dimethylformamide, slowly heat to 70°C and stir to dissolve, and react at 70°C for 4 hours.

[0047] Step 2: After the reaction temperature of step 1 is cooled to 40°C, add 0.7 parts of cuprous chloride catalyst and stir evenly. Take 28 parts of propylene bromide and slowly add dropwise for 40 minutes under condensation reflux conditions and stir. After the addition is complete, react for 3 hours.

[0048] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Wash three times with a large amount of water, rotary evaporate, remove impurities, and obtain a white solid. Recrystallize the white solid in toluene solvent, filter, package it after vacuum drying, and seal it to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) with a yield of 90%.

[0049] Example 6 A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) comprises the following steps: Step 1: Under the protection of N2, take 9 parts of sodium hydroxide, 12 parts of 2,5-furandicarboxylic acid, and then add 90 parts of methanol, slowly heat to 75°C and stir to dissolve, and react at 75°C for 5 hours.

[0050] Step 2: After the reaction temperature of step 1 is cooled to 60°C, add 0.5 parts of catalyst potassium chloride and stir evenly. Take 28 parts of bromopropylene and slowly dropwise add for 50 minutes under condensation reflux conditions and stir. After the dropwise addition is completed, react for 5 hours.

[0051] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Wash three times with a large amount of water, rotary evaporate, remove impurities, and obtain a white solid. The white solid is recrystallized in a chloroform solvent, filtered, packaged after vacuum drying, and sealed to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) with a yield of 92%.

[0052] Example 7 A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) comprises the following steps: Step 1: Under the protection of N2, take 8 parts of sodium hydroxide, 20 parts of 2,5-furandicarboxylic acid, and then add 100 parts of methanol, slowly heat to 80°C and stir to dissolve, and react at 80°C for 6 hours.

[0053] Step 2: After the reaction temperature of step 1 is cooled to 70°C, add 0.8 parts of the catalyst cuprous bromide and stir evenly. Take 30 parts of propylene bromide and slowly add dropwise for 60 minutes under condensation reflux conditions and stir. After the addition is complete, react for 6 hours.

[0054] Step 3: After the reaction is completed, cool to room temperature and filter to obtain a white solid suspended in the upper layer of the reaction solution. Wash three times with a large amount of water, rotary evaporate, remove impurities, and obtain a white solid. The white solid is recrystallized in tetrahydrofuran solvent, filtered, packaged after vacuum drying, and sealed to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate (FDCE) with a yield of 92%.

[0055] The above contents are only for explaining the technical idea of ​​the present invention and cannot be used to limit the protection scope of the present invention. Any changes made on the basis of the technical solution in accordance with the technical idea proposed by the present invention shall fall within the protection scope of the claims of the present invention.

Claims

1. A method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate, It is characterized in that include: First, the hydroxide, 2,5-furandicarboxylic acid and solvent are mixed under an inert atmosphere, stirred and reacted once, and then the temperature is lowered. Then, a catalyst is added and stirred evenly. Subsequently, an allyl compound is slowly added. After stirring and reacting twice, the mixture is cooled to room temperature and filtered to obtain a white solid suspended on the upper layer of the reaction solution. Finally, the mixture is washed, rotary evaporated, recrystallized, filtered and vacuum dried to obtain di(propyl-2-enyl)furan-2,5-dicarboxylate.

2. The method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate according to claim 1, It is characterized in that The mass ratio of the hydroxide, 2,5-furandicarboxylic acid, solvent, catalyst and allyl compound is (5-10): (10-20): (50-100): (0.4-0.8): (10-30).

3. The method for preparing di(propyl-2-alkenyl)furan-2,5-dicarboxylate according to claim 2, It is characterized in that The mass ratio of the solvent to the hydroxide is 20:(1-2); the mass ratio of the 2,5-furandicarboxylic acid to the hydroxide is 2:(1-1.5); the mass ratio of the catalyst to the 2,5-furandicarboxylic acid is 1:(12.5-25); the mass ratio of the allyl compound to the 2,5-furandicarboxylic acid is (1.2-2.4):

1.

4. The method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate according to claim 1, It is characterized in that The inert atmosphere is N 2 The temperature of the stirring reaction is 60-80°C, and the time of the stirring reaction is 3-6h; after cooling to 40-70°C, the catalyst is added.

5. The method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate according to claim 1, It is characterized in that The conditions of the secondary stirring reaction are: stirring the reaction for 3 to 6 hours under condensation reflux conditions.

6. The method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate according to claim 1, It is characterized in that The hydroxide is sodium hydroxide or potassium hydroxide; the solvent is at least one of water, methanol, ethanol and N,N-dimethylformamide; the catalyst is at least one of ferric chloride, ferric chloride, aluminum chloride, cupric chloride, cuprous chloride, potassium chloride and cuprous bromide.

7. The method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate according to claim 1, It is characterized in that The allyl compound is at least one of allyl chloride and allyl bromide.

8. The method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate according to claim 1, It is characterized in that The time for slowly adding the allyl compound is controlled to be 30 to 60 minutes.

9. The method for preparing di(propyl-2-enyl)furan-2,5-dicarboxylate according to claim 1, It is characterized in that The organic solvent for recrystallization is at least one of methanol, ethanol, n-hexane, cyclohexane, toluene, chloroform and tetrahydrofuran.

10. A di(propyl-2-enyl)furan-2,5-dicarboxylate, It is characterized in that It is prepared by the preparation method according to any one of claims 1 to 9, and has the structural formula: 。

Citation Information

Patent Citations

  • Flame-retardant vegetable oil-based waterborne polyurethane coating and preparation method thereof

    CN112280459A

  • Sulfur-containing furandicarboxylic acid polyester and preparation method thereof

    CN113185694A

  • Furan diglycidyl ethers and esters and their use for producing epoxy resins

    CN117529479A