CN105936630A - Synthesis method of 2,5-furan dicarboxylic acid - Google Patents
Synthesis method of 2,5-furan dicarboxylic acid Download PDFInfo
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- CN105936630A CN105936630A CN201610475815.4A CN201610475815A CN105936630A CN 105936630 A CN105936630 A CN 105936630A CN 201610475815 A CN201610475815 A CN 201610475815A CN 105936630 A CN105936630 A CN 105936630A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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Abstract
The invention discloses a synthesis method of 2,5-furan dicarboxylic acid. The synthesis method comprises the following steps: step one, making 2,5-dibromofuran and n-butyl lithium carry out reactions at a low temperature to obtain a reaction liquid; step two, maintaining a low temperature of obtained reaction liquid, introducing carbon dioxide to carry out reactions, then adding the reaction liquid into a low temperature acid solution to carry out acidification, extracting the solution for two times, merging the organic phases, washing the merged organic phase by deionized water and saturated sodium chloride for one time, wherein the volumes of the organic phase, deionized water, and saturated sodium chloride are the same; separating the organic phase, drying the organic phase by anhydrous sodium sulfate; carrying out rotary evaporation to remove the solvent, condensing to obtain a grey-white solid, and using a mixed solvent of glacial acetic acid and deionized water to carry out recrystallization to obtain a white solid namely 2,5-furan dicarboxylic acid. Cheap 2,5-dibromofuran is taken as the raw material, and carries out low temperature reactions with n-butyl lithium to obtain a reaction liquid, then the reaction liquid reacts with carbon dioxide, the reaction product is further acidified to obtain the target product 2,5-furan dicarboxylic acid, the yield is high, moreover, the cost is low, the conditions are mild, and the operation is convenient.
Description
Technical field
The present invention relates to the synthetic method of a kind of FDCA, particularly a kind of by 2,5-dibrom furan
The method of synthesis 2,5-furandicarboxylic acid.
Background technology
FDCA (FDCA) is one of USDOE's 12 " platform chemicals ", has wide
Wealthy application prospect.Its structure is similar to p-phthalic acid, be believed to replace p-phthalic acid for
Manufacture the important source material of ester plastic, manufacture the bis-terephthalate's that birdss of the same feather flock together (PET) of a new generation
Biodegradable plastic；Its structure has five rings difunctional feature, with p-phthalic acid six-membered ring structure
Compare, there is molecules align asymmetrical type, therefore can also be used to synthesizing optical/choke specific function high score
Sub-material；2,5 furandicarboxylic acids be also used as other fine chemicals, medicine and pesticide important in
Mesosome.Therefore, the preparation of FDCA be considered as great representational replacement Petroleum Production can
Continued biological conversion process, has the biggest application prospect and potentiality.
Lin Lu etc. (chemical reagent, 33,2011,11-12) report use alkalinity potassium permanganate aqueous solution chlorination
5 hydroxymethyl furfural (5-HMF) prepares FDCA.The method material concentration is low, and unit production capacity is low, simultaneously by
In employing aqueous slkali, cause subsequent products separate must be added to a large amount of acid dissociate separate out FDCA product,
Causing the generation of a large amount of abraum salt solution, environmental pollution is big.
Lin Lu etc. patent CN 101891719A and Xu Jie etc. at patent CN 103626726A and
CN 103724303A reports in aqueous slkali, with oxygen as oxidant, use noble-metal-supported to urge
Agent catalysis oxidation 5-HMF prepares FDCA.The method equally exists material concentration needs low, follow-up
Acidifying separates out the drawback of product.Patent CN104529957A is with 2,5-furan dicarbaldehyde and tert-Butanol peroxide
Aqueous solution also stirs reaction, then naturally cools to room temperature, obtains product；To product from
The heart separates to obtain precipitation, and washing precipitation is also dried, and obtains target product FDCA.Said method
The raw material of middle employing is 5 hydroxymethyl furfural, and its oxidative synthesis FDCA is broadly divided into metering
Oxidizing process, homogeneous catalysis method, heterogeneous catalysis method.Metering oxidizing process uses KMnO4、N2O4、HNO3
Deng as oxidant, 5 hydroxymethyl furfural is carried out oxidative synthesis FDCA.These oxidants
Serious to equipment corrosion, discharge time cause environmental pollution, not there is considerable application advantage.All
The catalyst that phase oxidation uses there is also slaine and separates difficult, the bromine environmental pollution shortcoming such as heavily.Compare it
Under, heterogeneous catalysis method has environmental protection, product is easily isolated, the more high advantage of catalytic efficiency.Use Au,
The heterogeneous catalysts such as Pt, Pd, the aldehyde radical of 5 hydroxymethyl furfural is first converted into carboxyl, forms 5-methylol
-2-furancarboxylic acid；Hydroxyl continues to be oxidized to carboxyl subsequently, it is thus achieved that FDCA.Obtain height to receive
Rate FDCA has difficulty, and reaction easily rests on the 5-methylol-2-furancarboxylic acid stage,
And using 5 hydroxymethyl furfural is that FDCA prepared by raw material, and preparation method is relative complex.
Summary of the invention
It is an object of the invention to solve at least the above and/or defect, and provide after at least and will say
Bright advantage.
In order to realize according to object of the present invention and further advantage, it is provided that a kind of 2,5-furan diformazan
The synthetic method of acid, comprises the following steps:
Step one, making 2,5-dibrom furan reacts at low temperatures with n-BuLi, obtains reactant liquor；
Step 2, the reactant liquor that obtain is kept low temperature, and be passed through carbon dioxide and react, then will
Reactant liquor addition acid solution at low temperature is acidified, obtains FDCA.
Preferably, in described step one, the process of reaction is: by 2,5-dibrom furan is dissolved in dry second
In ether, obtain 2,5-dibrom furan solution；Under pure nitrogen gas atmosphere protection, anti-at low-temperature reactor
Answering in device addition n-butyllithium solution, stirring is cooled to-50～-70 DEG C, then by 2,5-dibrom furan solution
It is slowly dropped into, dripped off in 1～3 hour, after dripping, continue stirring reaction 0.5～2 at-50～-70 DEG C
Hour, obtain reactant liquor.
Preferably, described 2,5-dibrom furan is 1:2～3 with the mol ratio of n-BuLi；Described normal-butyl
Lithium solution is n-BuLi hexane solution, and its concentration is 2～3mol/L；Described 2,5-dibrom furan is with dry
The weight ratio of dry ether is 1:2～4.
Preferably, described dry ether is replaced by dry tetrahydrofuran.
Preferably, in described step one, the temperature of low-temp reaction is-50～-70 DEG C；In described step 2,
Reactant liquor keeps the temperature of low temperature to be-50～-70 DEG C.
Preferably, in described step 2, acid solution at low temperature is the dilute hydrochloric acid solution of less than 10 DEG C；Described dilute
The concentration of hydrochloric acid is 0.3～0.5mol/L；The consumption of described acid solution at low temperature is the 1～3 of reactant liquor volume
Times.
Preferably, the process of described step 2 is: the temperature of reactant liquor step one obtained is maintained at
-50～70 DEG C, then pass to the carbon dioxide being dried, keep ventilation 1～3 hour, stop ventilation,
Reactant liquor warms naturally to room temperature, the white muddy shape of reactant liquor；Reactant liquor is poured slowly into less than 10 DEG C
Dilute hydrochloric acid in, stir 20～60 minutes, be then extracted twice with ether, organic facies is merged, respectively
Clean one time with deionized water isopyknic with organic facies and saturated sodium-chloride, separate organic facies, with anhydrous
Sodium sulfate is dried more than 4 hours；Then solvent is evaporated off with rotation, is concentrated into pale solid, use ice
Acetic acid/deionized water mixed solvent recrystallization, obtains white solid FDCA.
Preferably, the speed of described stirring is 150～280r/min.
Preferably, the volume ratio of described glacial acetic acid/deionized water is 5～10:1.
Preferably, when described ether extracts, the consumption of ether is 0.3～0.8 that total overall reaction liquid is long-pending
Times.
The present invention at least includes following beneficial effect: with cheap 2, and 5-dibrom furan is raw material, first
With n-BuLi generation low-temp reaction, obtain reactant liquor, then with carbon dioxide reaction, be acidified further
Obtaining the target product FDCA of high yield, this programme is with low cost, mild condition, operation
Easy.
Part is embodied by the further advantage of the present invention, target and feature by description below, and part also will
By the research of the present invention and practice are understood by the person skilled in the art.
Accompanying drawing illustrates:
Fig. 1 is the chemical equation of technical solution of the present invention.
Detailed description of the invention:
Below in conjunction with embodiment, the present invention is described in further detail, to make those skilled in the art join
Book word can be implemented according to this as directed.
Should be appreciated that used herein such as " have ", " comprising " and " including " term also
Do not allot other element one or more or the existence of a combination thereof or interpolation.
Embodiment 1:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, making 2,5-dibrom furan reacts at-50 DEG C with n-BuLi, obtains reactant liquor；
Described 2,5-dibrom furan is 1:2 with the mol ratio of n-BuLi；Described n-BuLi thinks that n-BuLi is just
The form of hexane solution adds, and its concentration is 2mol/L；
Step 2, the reactant liquor that obtain is kept-50 DEG C, and be passed through carbon dioxide and react, then will
Reactant liquor addition acid solution at low temperature is acidified, obtains FDCA；Acid solution at low temperature is 10 DEG C
Following dilute hydrochloric acid solution；The concentration of described dilute hydrochloric acid is 0.3mol/L；The consumption of described acid solution at low temperature
For reactant liquor volume 1 times.
Embodiment 2:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, making 2,5-dibrom furan reacts at-70 DEG C with n-BuLi, obtains reactant liquor；
Described 2,5-dibrom furan is 1:3 with the mol ratio of n-BuLi；Described n-BuLi thinks that n-BuLi is just
The form of hexane solution adds, and its concentration is 3mol/L；
Step 2, the reactant liquor that obtain is kept-50 DEG C, and be passed through carbon dioxide and react, then will
Reactant liquor addition acid solution at low temperature is acidified, obtains FDCA；Acid solution at low temperature is 10 DEG C
Following dilute hydrochloric acid solution；The concentration of described dilute hydrochloric acid is 0.5mol/L；The consumption of described acid solution at low temperature
For reactant liquor volume 3 times.
Embodiment 3:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, making 2,5-dibrom furan reacts at-60 DEG C with n-BuLi, obtains reactant liquor；
Described 2,5-dibrom furan is 1:2.5 with the mol ratio of n-BuLi；Described n-BuLi thinks n-BuLi
The form of hexane solution adds, and its concentration is 2.5mol/L；
Step 2, the reactant liquor that obtain is kept-60 DEG C, and be passed through carbon dioxide and react, then will
Reactant liquor addition acid solution at low temperature is acidified, obtains FDCA；Acid solution at low temperature is 10 DEG C
Following dilute hydrochloric acid solution；The concentration of described dilute hydrochloric acid is 0.4mol/L；The consumption of described acid solution at low temperature
For reactant liquor volume 2 times.
Embodiment 4:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, by 2,5-dibrom furan is dissolved in dry ether, obtains 2,5-dibrom furan solution；?
Under pure nitrogen gas atmosphere protection, the reactor of low-temperature reactor adds n-butyllithium solution, stirs cold
But to-50 DEG C, then by 2,5-dibrom furan solution is slowly dropped into, and drips off, after dripping in 1 hour
Continue stirring reaction 0.5 hour at-50 DEG C, obtain reactant liquor；Described 2,5-dibrom furan and normal-butyl
The mol ratio of lithium is 1:2；Described n-butyllithium solution is n-BuLi hexane solution, and its concentration is
2mol/L；Described 2,5-dibrom furan is 1:2 with the weight ratio of dry ether；
Step 2, the temperature of reactant liquor step one obtained are maintained at-50 DEG C, then pass to two be dried
Carbon oxide gas, keeps ventilation 1 hour, stops ventilation, and reactant liquor warms naturally to room temperature, reactant liquor
White muddy shape；Reactant liquor is poured slowly in the dilute hydrochloric acid of less than 10 DEG C, stirs 20 minutes, so
Be extracted twice with ether afterwards, by organic facies merge, respectively with deionized water isopyknic with organic facies and satisfy
Clean one time with sodium chloride, separate organic facies, be dried more than 4 hours with anhydrous sodium sulfate；Then with rotation
Solvent is evaporated off, is concentrated into pale solid, use glacial acetic acid/deionized water mixed solvent recrystallization,
To white solid 2,5-furandicarboxylic acid；The volume ratio of described glacial acetic acid/deionized water is 5:1；Described second
During ether extraction, the consumption of ether is 0.3 times that total overall reaction liquid is long-pending.
Embodiment 5:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, by 2,5-dibrom furan is dissolved in dry ether, obtains 2,5-dibrom furan solution；?
Under pure nitrogen gas atmosphere protection, the reactor of low-temperature reactor adds n-butyllithium solution, stirs cold
But to-70 DEG C, then by 2,5-dibrom furan solution is slowly dropped into, and drips off, after dripping in 3 hours
Continue stirring reaction 2 hours at-70 DEG C, obtain reactant liquor；Described 2,5-dibrom furan and n-BuLi
Mol ratio be 1:3；Described n-butyllithium solution is n-BuLi hexane solution, and its concentration is 2mol/L；
Described 2,5-dibrom furan is 1:4 with the weight ratio of dry ether；
Step 2, the temperature of reactant liquor step one obtained are maintained at-70 DEG C, then pass to two be dried
Carbon oxide gas, keeps ventilation 3 hours, stops ventilation, and reactant liquor warms naturally to room temperature, reactant liquor
White muddy shape；Reactant liquor is poured slowly in the dilute hydrochloric acid of less than 10 DEG C, stirs 60 minutes, so
Be extracted twice with ether afterwards, by organic facies merge, respectively with deionized water isopyknic with organic facies and satisfy
Clean one time with sodium chloride, separate organic facies, be dried more than 4 hours with anhydrous sodium sulfate；Then with rotation
Solvent is evaporated off, is concentrated into pale solid, use glacial acetic acid/deionized water mixed solvent recrystallization,
To white solid 2,5-furandicarboxylic acid；The volume ratio of described glacial acetic acid/deionized water is 10:1；Described use
During ether extraction, the consumption of ether is 0.8 times that total overall reaction liquid is long-pending.
Embodiment 6:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, by 2,5-dibrom furan is dissolved in dry ether, obtains 2,5-dibrom furan solution；?
Under pure nitrogen gas atmosphere protection, the reactor of low-temperature reactor adds n-butyllithium solution, stirs cold
But to-60 DEG C, then by 2,5-dibrom furan solution is slowly dropped into, and drips off, after dripping in 2 hours
Continue stirring reaction 1 hour at-60 DEG C, obtain reactant liquor；Described 2,5-dibrom furan and n-BuLi
Mol ratio be 1:2.5；Described n-butyllithium solution is n-BuLi hexane solution, and its concentration is
2.5mol/L；Described 2,5-dibrom furan is 1:3 with the weight ratio of dry ether；
Step 2, the temperature of reactant liquor step one obtained are maintained at-60 DEG C, then pass to two be dried
Carbon oxide gas, keeps ventilation 2 hours, stops ventilation, and reactant liquor warms naturally to room temperature, reactant liquor
White muddy shape；Reactant liquor is poured slowly in the dilute hydrochloric acid of less than 10 DEG C, stirs 30 minutes, so
Be extracted twice with ether afterwards, by organic facies merge, respectively with deionized water isopyknic with organic facies and satisfy
Clean one time with sodium chloride, separate organic facies, be dried more than 4 hours with anhydrous sodium sulfate；Then with rotation
Solvent is evaporated off, is concentrated into pale solid, use glacial acetic acid/deionized water mixed solvent recrystallization,
To white solid 2,5-furandicarboxylic acid；The volume ratio of described glacial acetic acid/deionized water is 8:1；Described second
During ether extraction, the consumption of ether is 0.5 times that total overall reaction liquid is long-pending.
Embodiment 7:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, by 2,5-dibrom furan 100g is dissolved in 300mL dry ether, obtains 2,5-dibromo
Tetrahydrofuran solution；Under pure nitrogen gas atmosphere protection, add in the 1000mL reactor of low-temperature reactor
390mL n-butyllithium solution, stirring is cooled to-60 DEG C, and then by 2,5-dibrom furan solution is slowly dropped into,
Dripped off in 2 hours, continue stirring reaction 1 hour at-60 DEG C after dripping, obtain reactant liquor；Institute
Stating n-butyllithium solution is n-BuLi hexane solution, and its concentration is 2.5mol/L；
Step 2, the temperature of reactant liquor step one obtained are maintained at-60 DEG C, then pass to two be dried
Carbon oxide gas, keeps blistering reaction 2 hours, stops ventilation, and reactant liquor warms naturally to room temperature, instead
Answer the white muddy shape of liquid；Reactant liquor is poured slowly in the dilute hydrochloric acid of less than 10 DEG C, stirs 30 minutes,
Then it is extracted twice with 1000mL ether, organic facies is merged, goes with isopyknic with organic facies respectively
Ionized water and saturated sodium-chloride clean one time, separate organic facies, are dried more than 4 hours with anhydrous sodium sulfate；
Then solvent is evaporated off with rotation, is concentrated into pale solid, use glacial acetic acid/deionized water mixed solvent weight
Crystallization, obtains white solid FDCA 37.1g, productivity about 53.7%；Described dilute hydrochloric acid is for taking
50mL mass fraction be 38% hydrochloric acid add in 1500mL deionized water formulated.
Embodiment 8:
The synthetic method of a kind of FDCA, comprises the following steps:
Step one, by 2,5-dibrom furan 200g is dissolved in 600mL dry ether, obtains 2,5-dibromo
Tetrahydrofuran solution；Under pure nitrogen gas atmosphere protection, in the reactor of low-temperature reactor, just adding 900mL
Butyl lithium solution, stirring is cooled to-70 DEG C, and then by 2,5-dibrom furan solution is slowly dropped into, little 3
Time interior drip off, continue stirring reaction 1.5 hours at-70 DEG C after dripping, obtain reactant liquor；Described just
Butyl lithium solution is n-BuLi hexane solution, and its concentration is 2.5mol/L；
Step 2, the temperature of reactant liquor step one obtained are maintained at-70 DEG C, then pass to two be dried
Carbon oxide gas, keeps blistering reaction 2 hours, stops ventilation, and reactant liquor warms naturally to room temperature, instead
Answer the white muddy shape of liquid；Reactant liquor is poured slowly in the dilute hydrochloric acid of 5 DEG C, stirs 30 minutes, then
It is extracted twice with 1500mL ether, organic facies is merged, respectively with deionization isopyknic with organic facies
Water and saturated sodium-chloride clean one time, separate organic facies, are dried more than 4 hours with anhydrous sodium sulfate；So
Solvent is evaporated off with rotation afterwards, is concentrated into pale solid, use glacial acetic acid/deionized water mixed solvent heavily to tie
Crystalline substance, obtains white solid FDCA 85g, productivity about 62%；Described dilute hydrochloric acid is for taking 80mL
Mass fraction be 38% hydrochloric acid add in 1800mL deionized water formulated.
Although embodiment of the present invention are disclosed as above, but it is not restricted to description and embodiment party
Listed utilization in formula, it can be applied to various applicable the field of the invention completely, for being familiar with ability
For the personnel in territory, be easily achieved other amendment, therefore without departing substantially from claim and etc. homotype
Enclosing under limited general concept, the present invention is not limited to specific details and shown here as the reality with description
Example.
Claims (10)
1. the synthetic method of a FDCA, it is characterised in that comprise the following steps:
Step one, making 2,5-dibrom furan reacts at low temperatures with n-BuLi, obtains reactant liquor；
Step 2, the reactant liquor that obtain is kept low temperature, and be passed through carbon dioxide and react, then will
Reactant liquor addition acid solution at low temperature is acidified, obtains FDCA.
2. the synthetic method of FDCA as claimed in claim 1, it is characterised in that described
In step one, the process of reaction is: by 2,5-dibrom furan is dissolved in dry ether, obtains 2,5-dibromo furan
Mutter solution；Under pure nitrogen gas atmosphere protection, the reactor of low-temperature reactor adds n-BuLi molten
Liquid, stirring is cooled to-50～-70 DEG C, and then by 2,5-dibrom furan solution was slowly dropped into, at 1～3 hour
Inside drip off, continue stirring reaction 0.5～2 hour at-50～-70 DEG C after dripping, obtain reactant liquor.
3. the synthetic method of FDCA as claimed in claim 2, it is characterised in that described
2,5-dibrom furan is 1:2～3 with the mol ratio of n-BuLi；Described n-butyllithium solution be n-BuLi just
Hexane solution, its concentration is 2～3mol/L；Described 2,5-dibrom furan with the weight ratio of dry ether is
1:2～4.
4. the synthetic method of FDCA as claimed in claim 2 or claim 3, it is characterised in that
Described dry ether is replaced by dry tetrahydrofuran.
5. the synthetic method of FDCA as claimed in claim 1, it is characterised in that described
In step one, the temperature of low-temp reaction is-50～-70 DEG C；In described step 2, reactant liquor keeps low temperature
Temperature is-50～-70 DEG C.
6. the synthetic method of FDCA as claimed in claim 1, it is characterised in that described
In step 2, acid solution at low temperature is the dilute hydrochloric acid solution of less than 10 DEG C；The concentration of described dilute hydrochloric acid be 0.3～
0.5mol/L；The consumption of described acid solution at low temperature is 1～3 times of reactant liquor volume.
7. the synthetic method of FDCA as claimed in claim 1, it is characterised in that described
The process of step 2 is: the temperature of reactant liquor step one obtained is maintained at-50～70 DEG C, then passes to
The carbon dioxide being dried, keeps ventilation 1～3 hour, stops ventilation, and reactant liquor warms naturally to room
Temperature, the white muddy shape of reactant liquor；Reactant liquor is poured slowly in the dilute hydrochloric acid of less than 10 DEG C, stirring
20～60 minutes, be then extracted twice with ether, by organic facies merge, respectively with organic facies equal-volume
Deionized water and saturated sodium-chloride clean one time, separate organic facies, be dried 4 hours with anhydrous sodium sulfate
Above；Then solvent is evaporated off with rotation, is concentrated into pale solid, use glacial acetic acid/deionized water mixing
Solvent recrystallization, obtains white solid FDCA.
8. the synthetic method of the FDCA as described in claim 2 or 7, it is characterised in that
The speed of described stirring is 150～280r/min.
9. the synthetic method of FDCA as claimed in claim 7, it is characterised in that described
The volume ratio of glacial acetic acid/deionized water is 5～10:1.
10. the synthetic method of FDCA as claimed in claim 7, it is characterised in that institute
Stating the consumption of ether when extracting with ether is long-pending 0.3～0.8 times of total overall reaction liquid.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977476A (en) * | 2017-04-05 | 2017-07-25 | 华中科技大学 | A kind of method for preparing 2,5 furandicarboxylic acids |
| CN109734689A (en) * | 2019-02-18 | 2019-05-10 | 河南中医药大学 | A method of furandicarboxylic acid is prepared using cuprous halide salt |
| US10344010B2 (en) | 2017-10-30 | 2019-07-09 | Industrial Technology Research Institute | Method for purifying crude of 2,5-furandicarboxylic acid by crystallization |
| CN114787140A (en) * | 2019-12-20 | 2022-07-22 | 福兰尼克斯科技公司 | Heat treatment of organic acids and purified 2, 5-furandicarboxylic acid |
| CN114929679A (en) * | 2019-12-20 | 2022-08-19 | 福兰尼克斯科技公司 | Heat treatment of water and purified 2, 5-furandicarboxylic acid |
-
2016
- 2016-06-23 CN CN201610475815.4A patent/CN105936630A/en active Pending
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| HIGUCHI, HIROYUKI ET AL: "Synthesis and properties of α,ω-disubstituted oligo(3-hexylthiophene)s and oligothienoquinonoids in head-to-head orientation", 《BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN》 * |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977476A (en) * | 2017-04-05 | 2017-07-25 | 华中科技大学 | A kind of method for preparing 2,5 furandicarboxylic acids |
| CN106977476B (en) * | 2017-04-05 | 2019-03-08 | 华中科技大学 | A method of preparing 2,5- furandicarboxylic acid |
| US10344010B2 (en) | 2017-10-30 | 2019-07-09 | Industrial Technology Research Institute | Method for purifying crude of 2,5-furandicarboxylic acid by crystallization |
| CN109734689A (en) * | 2019-02-18 | 2019-05-10 | 河南中医药大学 | A method of furandicarboxylic acid is prepared using cuprous halide salt |
| CN114787140A (en) * | 2019-12-20 | 2022-07-22 | 福兰尼克斯科技公司 | Heat treatment of organic acids and purified 2, 5-furandicarboxylic acid |
| CN114929679A (en) * | 2019-12-20 | 2022-08-19 | 福兰尼克斯科技公司 | Heat treatment of water and purified 2, 5-furandicarboxylic acid |
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Application publication date: 20160914 |