CN115974821B - 2, 5-furandicarboxylic acid amplification production method - Google Patents
2, 5-furandicarboxylic acid amplification production method Download PDFInfo
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Abstract
The invention belongs to the technical field of organic synthesis, and particularly relates to a 2, 5-furandicarboxylic acid amplification production method. The method of the invention comprises the following steps: dissolving bicarbonate in low-melting-point molten salt to obtain a bicarbonate solid catalyst doped with the molten salt; the furoate is dissolved in methanol or ethanol solvent to prepare salt solution; adding bicarbonate solid catalyst into salt solution to obtain a porous honeycomb crystal structure reaction system with high comparison area; or, adding the furanic acid salt, the alkaline catalyst and the low-melting-point molten salt into water, adding an inorganic carrier, and removing the water to obtain a uniformly mixed dry reactant system; and further reacting to obtain the 2, 5-furandicarboxylic acid. According to the invention, the raw materials and the catalyst are pretreated, so that the reaction rate is improved, and the water generated in the reaction is effectively removed, thereby realizing the efficient preparation of the 2, 5-furandicarboxylic acid.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a 2, 5-furandicarboxylic acid amplification production method.
Background
The synthesis of 2, 5-furandicarboxylic acid mainly adopts a method for oxidizing 5-hydroxymethylfurfural, and the problems existing in the method at present comprise: firstly, fructose is needed to be used as a raw material for synthesizing the 5-hydroxymethylfurfural through high conversion, and the future large-scale production can compete with grains; secondly, the 5-hydroxymethyl furfural has unstable structure and extremely good water solubility and is difficult to separate, so that the preparation of the high-purity 5-hydroxymethyl furfural has high difficulty and high cost; in addition, when the 5-hydroxymethylfurfural is oxidized to synthesize the 2, 5-furandicarboxylic acid, a noble metal catalyst with higher price is often needed, the variety of oxidation intermediates is more, the selective preparation has certain difficulty, and the conversion rate is lower. Therefore, the current 5-hydroxymethylfurfural oxidation method for preparing 2, 5-furandicarboxylic acid is not suitable for large-scale industrialized production, and the large-scale application of the 2, 5-furandicarboxylic acid and downstream polyester products thereof is greatly limited.
Another method for synthesizing 2, 5-furandicarboxylic acid adopts the addition reaction of furoic acid (salt) and carbon dioxide, and the furoic acid raw material of the method is from non-grain biomass to non-grain biomassAnd the method has the advantages of mass production, low price and commercial prospect. US20200157071 and WO2013096998 report a process for the preparation of 2, 5-furandicarboxylic acid by disproportionation of furoic acid (salt) with carbon dioxide using a metal catalyst, in which furandicarboxylic acid is obtained and equimolar equivalent furanmonomer is also disproportionated, so that the yield of the main product furandicarboxylic acid is low, and in addition, in the course of the disproportionation reaction, a part of 2, 4-furandicarboxylic acid is formed, and it is difficult to separate from 2, 5-furandicarboxylic acid, the selectivity of the reaction is poor, and pure 2, 5-furandicarboxylic acid is difficult to obtain. WO2016153937 reports a process for the preparation of 2, 5-furandicarboxylic acid by the carboxylation of furan formate with carbon dioxide using cesium carbonate, on the basis of which WO2019214576 and WO2021061545 develop a process for the synthesis of 2, 5-furandicarboxylic acid from furan formate and an alkaline catalyst under carbon dioxide gas conditions in a low melting molten salt system. The essence of the reaction is furoate and alkaline catalyst and CO melted or dissolved in low melting point molten salt 2 But as the reaction proceeds, the continuous formation of solid 2, 5-furandicarboxylic acid salt in the system severely hinders the starting materials and catalyst from CO 2 Thereby inhibiting efficient progress of the reaction and such now being more apparent in the reaction scale-up synthesis process. For this reason, WO2021158890 proposes to use a reaction amplifying device with shearing and crushing effects to crush the solid 2, 5-furandicarboxylic acid salt generated in the system, so as to increase the contact area of the gas and the liquid phases in the reaction system and improve the conversion efficiency of the reaction. However, as the proportion of the solid 2, 5-furandicarboxylic acid salt in the reaction system increases, it is conceivable that it is difficult to continue to increase the conversion of the reaction by merely pulverizing the solid matters generated in the system with the apparatus. Therefore, developing a new process for continuously maintaining the high specific contact efficiency of the gas phase and the liquid phase in the reaction system is important for the high-yield and large-scale production of the 2, 5-furandicarboxylic acid.
Disclosure of Invention
The invention aims to provide a high-yield amplified production process of 2, 5-furandicarboxylic acid.
The technical scheme of the invention is a 2, 5-furandicarboxylic acid amplification production method, which comprises the following steps:
step s1, raw material pretreatment: using one of the following operations a or b;
a. adding furan formate, an alkaline catalyst and low-melting-point molten salt into water, uniformly mixing, adding an inorganic carrier, spray-drying to remove water, obtaining a uniformly mixed dry reactant system, drying under reduced pressure, and crushing; the furanic acid salt is potassium furanic acid salt, sodium furanic acid salt, copper furanic acid salt, calcium furanic acid salt or magnesium furanic acid salt; the alkaline catalyst is carbonate, bicarbonate, phosphate or hydroxide alkali containing alkali metal or alkaline earth metal; the low-melting-point molten salt is potassium formate, sodium formate, potassium acetate/sodium acetate mixed molten salt, potassium isobutyrate or cesium acetate; the molar weight of the alkaline catalyst is 0.5-1.3 times of that of the furanic formate, the mass of the low-melting molten salt is 0.2-0.4 times of the sum of the furanic formate and the alkaline catalyst, and the dosage of the inorganic carrier is 0.3-2 times of the total mass of the furanic formate, the alkaline catalyst and the low-melting molten salt;
b. bicarbonate under vacuum or CO 2 Under the atmosphere, heating and dissolving in low-melting-point molten salt, and cooling to room temperature to obtain a bicarbonate solid catalyst doped with the molten salt; the furoate is dissolved in methanol or ethanol solvent to prepare salt solution; adding bicarbonate solid catalyst into salt solution in a reactor, and heating to 150-280 ℃ to obtain a porous honeycomb crystal structure reaction system with a high comparison area; the furoate is potassium furoate, cesium furoate, sodium furoate and calcium furoate; the bicarbonate is cesium bicarbonate, potassium bicarbonate, sodium bicarbonate, rubidium bicarbonate, calcium bicarbonate or magnesium bicarbonate; the molar ratio of bicarbonate to furoate is 1:1-4; the consumption of the low-melting-point molten salt is calculated according to 0.2 to 3 times of the total mass of the furoate and the bicarbonate;
step s2, reaction: CO continuous at a flow rate of 0.4-2 MPa, 200-5000 mL/min 2 Under the air flow, the temperature of the reaction system is raised to 220-320 ℃ for reaction for 1-6 hours; cooling to room temperature, adding deionized water for dissolution, adding active carbon for decolorization, filtering to obtain aqueous solution, adding hydrochloric acid for acidification,filtering the solid to obtain an off-white solid, washing with ethanol, and drying to obtain the 2, 5-furandicarboxylic acid.
Wherein in step s1, the particle size of the reactant system after crushing is controlled to be less than 1 micron; the water content of the reactant system after drying under reduced pressure was <20ppm.
Further, in the operation a of the step s1, the molar amount of the basic catalyst is 1.1 to 1.2 times that of the furanic formate; the mass of the low-melting molten salt is 0.3 times of the sum of the masses of the furanic formate and the alkaline catalyst.
In particular, in the b operation of the step s1, the molar ratio of bicarbonate to furoate is 1:1.2-1.4; the consumption of the low-melting-point molten salt is calculated according to 0.25-0.5 times of the total mass of the furoate and the bicarbonate.
Specifically, in the operation b of the step s1, the temperature is raised to 200-220 ℃ to obtain a porous honeycomb crystal structure reaction system with a high comparison area.
Further, in step s2, the reactor for the reaction is a high temperature and high pressure ebullated bed, a spray drying apparatus or a turn drying apparatus.
In particular, in step s2, CO 2 The pressure of the air flow is 0.8-1 MPa, and CO 2 The gas flow is reacted for 2 hours at the temperature of 293-305 ℃ at 1500 mL/min.
In the step s2, the activated carbon is decolorized 3 times.
The invention also provides the 2, 5-furandicarboxylic acid prepared by the method.
The invention has the beneficial effects that: aiming at the problems that the contact area of the carbon dioxide, furoate and carbonate alkaline catalyst in a reaction system is blocked along with the gradual generation of solid 2, 5-furandicarboxylic acid salt in the process of preparing 2, 5-furandicarboxylic acid by the reaction of furoic acid (salt) and carbon dioxide in a molten system, the reaction rate is slow and the side reaction is increased. The invention ensures the CO in the reaction process by doping the raw materials and the catalyst and designing a core-shell structure 2 The continuous high contact area is provided between the catalyst and the dissolved reactant, so that the reaction rate is improved, and water generated in the reaction is effectively discharged from the system, thereby realizing the efficient preparation of the 2, 5-furandicarboxylic acid. The invention is thatThe method comprises the steps of rapidly dissolving bicarbonate of alkali metal or alkaline earth metal in molten salt with low melting point under heating condition, cooling to room temperature to obtain a solid bicarbonate catalyst doped with molten salt, taking the solid bicarbonate catalyst as a core, and further coating the core-structure bicarbonate catalyst with raw material furoate as a shell structure to prepare a reaction system with a core-shell structure. When the reaction temperature reaches or exceeds the decomposition degree of bicarbonate, the bicarbonate is gradually decomposed into carbonate by maintaining the temperature, and meanwhile water generated by thermal decomposition overflows from the surface of the nuclear structure, so that the whole solid nuclear shell system is converted into a porous honeycomb crystal structure reaction system with a high comparison area. Under the boiling bed, when carbon dioxide is continuously introduced, the contact area between carbon dioxide gas and reaction raw materials and between carbonate catalysts can be greatly increased, the reaction efficiency is improved, and in addition, because bicarbonate decomposition and 2, 5-furandicarboxylic acid salt generation form balance, the whole reaction system can continuously keep a hollow core-shell structure, and the reaction system can ensure the reaction with CO 2 The gases remain in sufficient contact to increase the conversion of the furoate. The invention can ensure that the furoate can still prepare the 2, 5-furandicarboxylic acid with high efficiency and high conversion even in the large-scale amplifying process.
Description of the embodiments
The preparation process is as follows, see table 1.
(1) Pretreatment of raw materials
The method comprises the steps of adding furanic acid salt (potassium furanic acid salt, sodium furanic acid salt, copper furanic acid salt, calcium furanic acid salt, magnesium furanic acid salt), alkaline catalyst of alkali metal or alkaline earth metal (comprising carbonate, bicarbonate, phosphate and hydroxide alkali of alkali metal or alkaline earth metal) with the molar quantity of 1.1-1.3 times of furanic acid salt and molten salt with low melting point (comprising potassium formate, sodium formate, potassium acetate, mixed molten salt of potassium acetate/sodium acetate, potassium isobutyrate, cesium acetate and the like) with the mass sum of 0.2-0.4 times of furanic acid salt and alkaline catalyst into water for mixing, adding a certain amount of inorganic carriers (comprising all commercial inorganic carriers with the mass of 0.3-2 times of the mass of the total material) such as silicon oxide, diatomite, activated carbon, white carbon black, glass beads, titanium dioxide and the like, removing aqueous solution by spray drying, obtaining a dry reactant system with the inorganic matter load, and carrying out reduced pressure drying to obtain solid material, wherein the particle size of the fine powder is controlled to be less than 1 micrometer, and the water content of the system is less than 20ppm.
(2) Reaction
Adding the mixture into 100L boiling bed system with fluidization function under dry carbon dioxide atmosphere, and regulating CO of the system 2 The air flow is 200-5000 mL/min, so that the material powder is fully dispersed and reacted in the boiling reactor, the temperature of the reaction system is constantly set at 275-320 ℃, the reaction pressure is set at 0.4-2 MPa, the gas outlet of the boiling reactor is connected with a high-efficiency condensing device, and the CO is ensured 2 The air flow can discharge the byproduct water generated by the reaction out of the system, CO 2 And (3) recycling through a dryer and a fan, wherein the reaction time is 1-5 h.
(3) Purification
Dissolving the solid material obtained after the reaction in water, filtering, leaching the solid carrier, recycling, adding active carbon into the filtrate for decoloring, filtering to remove the active carbon, obtaining a clear and transparent aqueous solution, adding hydrochloric acid for acidification, carrying out suction filtration on the separated 2, 5-furandicarboxylic acid to obtain a pure white solid, washing with industrial ethanol to obtain a high-purity 2, 5-furandicarboxylic acid monomer, wherein the purity is 98% -99.9%, and the separation yield is 95% -100%.
Table 1 examples 1 to 6 raw materials and parameter control
Comparative example 1 (comparison under no load):
in a 100L ebullated bed reactor, potassium 2-furancarboxylate (15.6 kg), potassium carbonate (16.5 kg) and 96.2 kg of anhydrous potassium formate were added, and the powder was uniformly mixed (particle size of powder particles 0.6 to 1 μm). CO of regulatory system 2 The air flow is 1500 mL/min, so that the material powder is fully dispersed and reacted in a boiling reactor, the temperature of a reaction system is constantly set at 290 ℃, and the reaction pressure is set at 0.The gas outlet of the boiling reactor is connected with a high-efficiency condensing device at 9 MPa, so that CO is ensured 2 The air flow can discharge the byproduct water generated by the reaction out of the system, CO 2 And (5) recycling through a dryer and a fan, and reacting for 6 hours. Dissolving the solid material obtained after the reaction in water, adding active carbon for decoloring, filtering to remove the active carbon, obtaining a clear and transparent aqueous solution, adding hydrochloric acid for acidification, carrying out suction filtration on the separated 2, 5-furandicarboxylic acid to obtain a pure white solid, and washing with industrial ethanol to obtain a high-purity 2, 5-furandicarboxylic acid monomer with the purity of 98% and the separation yield of 57%. And (3) injection: a large amount of side reactants are produced in the reaction; the main byproducts are furan byproducts generated by the disproportionation of furan formate, including furan and furan derivatives, the HPLC detection of tail gas is carried out, the existence of furan is found, and acetate is found to be generated by nuclear magnetism detection.
Pilot experiment: in a 1L reactor, potassium 2-furancarboxylate (156 g), potassium carbonate (165 g) and anhydrous potassium formate (96.2 g) were added, and the air and water vapor in the system were purged with a dry carbon dioxide gas stream. The reaction system was gradually warmed to 285 ℃, reacted under a stirring condition under a carbon dioxide gas flow of 8bar for 6 hours, and a solid system was obtained, cooled, dissolved in water, decolorized with activated carbon (500 kg each time, 3 times of decolorization), and filtered to obtain a transparent aqueous solution. Adding hydrochloric acid for acidification, and carrying out suction filtration on the solid to obtain an off-white solid, washing the off-white solid with industrial ethanol to obtain the 2, 5-furandicarboxylic acid monomer with the purity of 97.8%, and separating the 2, 5-furandicarboxylic acid monomer with the yield of 65%.
Amplification experiment: in a 100L reactor, potassium 2-furancarboxylate (15.6 kg), potassium carbonate (16.5 kg) and anhydrous potassium formate (96.2 kg) were added, and the air and water vapor in the system were purged with a dry carbon dioxide gas stream. The reaction system was gradually warmed to 285 ℃, reacted under a stirring condition under a carbon dioxide gas flow of 8bar for 6 hours, and a solid system was obtained, cooled, dissolved in water, decolorized with activated carbon (500 kg each time, 3 times of decolorization), and filtered to obtain a transparent aqueous solution. Adding hydrochloric acid for acidification, and carrying out suction filtration on the solid to obtain an off-white solid, washing the off-white solid with industrial ethanol to obtain the 2, 5-furandicarboxylic acid monomer with 96% purity, and separating the 2, 5-furandicarboxylic acid monomer with 40% yield.
Comparative example 3 (cesium furancarboxylate and cesium carbonate reaction systems, see WO2021158890A1 patent):
in a 1000L high-temperature and high-pressure reactor equipped with a wall-mounted scraper anchor stirrer, cesium 2-furancarboxylate (156 kg) and potassium carbonate (115 kg) are added to uniformly mix powder, and air and water vapor in the system are purged by dry carbon dioxide gas flow. The reaction system is gradually heated to 252 ℃, and reacts for 1 hour under the stirring condition under the flow of 0.8 MPa of carbon dioxide, the obtained solid system is cooled, dissolved by adding water, decolorized by adding active carbon (500 kg each time and 3 times of decolorization), and filtered, thus obtaining transparent aqueous solution. Adding hydrochloric acid for acidification, and carrying out suction filtration on the solid to obtain an off-white solid, washing the off-white solid with industrial ethanol to obtain the 2, 5-furandicarboxylic acid monomer with the purity of 98.5%, and separating the 2, 5-furandicarboxylic acid monomer with the yield of 69%.
The specific operation is as follows (table 2):
the furoate (the dosage is 100mol, and comprises alkali metal furoate such as potassium furoate, cesium furoate, sodium furoate, calcium furoate and the like and alkaline earth metal furoate) is dissolved in methanol or ethanol solvent to prepare salt solution for standby. In a 100L high-temperature high-pressure ebullated bed reactor, bicarbonate of alkali metal or alkaline earth metal (comprising cesium bicarbonate, potassium bicarbonate, sodium bicarbonate, rubidium bicarbonate, calcium bicarbonate, magnesium bicarbonate, etc., the dosage is 1-4 times mole of furoate) is put in vacuum or CO 2 Under the atmosphere, the catalyst is heated and rapidly dissolved in molten salt with low melting point (the usage amount of the molten salt is 0.2-3 times of the total mass of furoate and bicarbonate), and then the reaction mixture is cooled to room temperature to obtain the bicarbonate solid catalyst doped with the molten salt. And then adding the solid catalyst prepared above into an alcohol solution of furoate, heating to quickly evaporate the alcohol solvent, and obtaining a reaction system of the furoate coated bicarbonate catalyst. Then heating the reaction system to reach or exceed the decomposition degree of bicarbonate (the heating temperature exceeds the decomposition temperature of corresponding bicarbonate and is 150-280 ℃), and maintaining the temperature to gradually decompose the bicarbonate into carbonate, wherein water generated by thermal decomposition in the process is expressed from the nuclear structure tableThe surface overflows, so that the whole solid core-shell system is converted into a porous honeycomb crystal structure reaction system with a high comparison area.
CO continuous at 0.4-1.2 MPa 2 And under the air flow, the temperature of the reaction system is increased to 220-305 ℃ to react for 1-5 hours. Cooling the reaction system to room temperature, adding deionized water for dissolution, adding active carbon for decolorization (1 kg for 3 times each time), adding hydrochloric acid into the water solution obtained by filtration for acidification, carrying out suction filtration on the solid to obtain an off-white solid, washing with industrial ethanol, and drying to obtain the 2, 5-furandicarboxylic acid monomer with the purity of 99.9%, wherein the reaction yield is 95-100%.
Comparative example 4
Cesium furoate (100 mol) and 75mol cesium carbonate are added into a 100L high temperature and high pressure reactor with a shearing effect stirring paddle, and the mixture is continuously added into CO 2 The temperature of the reaction system was raised to 250℃under a stream of air, and the reaction was carried out for 1 hour. Cooling the reaction system to room temperature, adding deionized water for dissolution, adding active carbon for decolorization (1 kg for 3 times each time), adding hydrochloric acid into the water solution obtained by filtration for acidification, carrying out suction filtration on the solid to obtain an off-white solid, washing with industrial ethanol, and drying to obtain a 2, 5-furandicarboxylic acid monomer with the purity of 98%, wherein the reaction yield is 80%.
Potassium furoate (100 mol), potassium carbonate (75 mol), potassium formate (7.6 Kg, 0.3 times of total mass of potassium furoate and potassium carbonate) were added to a 100L high temperature and high pressure reactor with a shearing effect stirring paddle, and the mixture was stirred under continuous CO 2 The temperature of the reaction system was raised to 250℃under a stream of air, and the reaction was carried out for 1 hour. Cooling the reaction system to room temperature, adding deionized water for dissolution, adding active carbon for decolorization (1 kg for 3 times each time), adding hydrochloric acid into the water solution obtained by filtration for acidification, carrying out suction filtration on the solid to obtain an off-white solid, washing with industrial ethanol, and drying to obtain a 2, 5-furandicarboxylic acid monomer with the purity of 97.5%, wherein the reaction yield is 75%.
Table 2 preparation and effect of examples 7 to 11, comparative examples 4 and 5
Claims (5)
1. The 2, 5-furandicarboxylic acid amplification production method is characterized by comprising the following steps:
step s1, raw material pretreatment: bicarbonate under vacuum or CO 2 Under the atmosphere, heating and dissolving in low-melting-point molten salt, and cooling to room temperature to obtain a bicarbonate solid catalyst doped with the molten salt; the furoate is dissolved in methanol or ethanol solvent to prepare salt solution; adding bicarbonate solid catalyst into salt solution in a reactor, and heating to 150-280 ℃ to obtain a reaction system with a porous honeycomb crystal structure; the low-melting-point molten salt is potassium formate or sodium formate; the furoate is potassium furoate, cesium furoate, sodium furoate and calcium furoate; the bicarbonate is cesium bicarbonate, potassium bicarbonate, sodium bicarbonate, rubidium bicarbonate, calcium bicarbonate or magnesium bicarbonate; the molar ratio of bicarbonate to furoate is 1:1.2-1.4; the consumption of the low-melting-point molten salt is calculated according to 0.25-0.5 times of the total mass of furoate and bicarbonate;
step s2, reaction: CO continuous at a flow rate of 0.4-2 MPa, 200-5000 mL/min 2 Under the air flow, the temperature of the reaction system is raised to 220-320 ℃ for reaction for 1-6 hours; cooling to room temperature, adding deionized water for dissolution, adding active carbon for decolorization, adding hydrochloric acid into the water solution obtained by filtration for acidification, carrying out suction filtration on the solid to obtain an off-white solid, washing with ethanol, and drying to obtain 2, 5-furandicarboxylic acid.
2. The method of claim 1, wherein in step s1, the temperature is raised to 200-220 ℃ to obtain a reaction system with a porous honeycomb crystal structure.
3. The process of claim 1, wherein in step s2, the reactor for the reaction is a high temperature high pressure ebullated bed.
4. The method according to claim 1, wherein in step s2, CO 2 The pressure of the air flow is 0.8-1 MPa, and CO 2 The gas flow is reacted for 2 hours at the temperature of 293-305 ℃ at 1500 mL/min.
5. The method of claim 1, wherein in step s2, activated carbon is decolorized 3 times.
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