CN106083779B - A kind of synthetic method of 2,5- furandicarboxylic acids - Google Patents
A kind of synthetic method of 2,5- furandicarboxylic acids Download PDFInfo
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- CN106083779B CN106083779B CN201610463912.1A CN201610463912A CN106083779B CN 106083779 B CN106083779 B CN 106083779B CN 201610463912 A CN201610463912 A CN 201610463912A CN 106083779 B CN106083779 B CN 106083779B
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- C—CHEMISTRY; METALLURGY
- 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
Abstract
The invention discloses a kind of synthetic methods of 2,5 furandicarboxylic acids, include the following steps：Step 1: by 2, organic solvent is added in 5 dimethyl furans and N bromo-succinimides, and bromo-reaction occurs under the action of initiator；Obtain 2,5 dibromo methylfuran of bromination product；Step 2: making 2,5 dibromo methylfuran of bromination product that oxidation reaction occur under the action of oxidant, 2,5 furandicarboxylic acids are obtained.For the present invention with cheap 2,5 dimethyl furans for raw material, first bromo synthesizes 2,5 dibromo methylfurans, and then a step aoxidizes to obtain 2,5 furandicarboxylic acid of target product of high yield, and this programme is of low cost, mild condition, easy to operate.
Description
Technical field
The present invention relates to a kind of synthetic methods of 2,5-furandicarboxylic acid, especially a kind of to be synthesized by 2,5- dimethyl furans
The method of 2,5- furandicarboxylic acids.
Background technology
2,5-furandicarboxylic acid (FDCA) is one of U.S. Department of Energy 12 " platform chemicals ", before having wide application
Scape.Its structure is similar to terephthalic acid (TPA), is believed to the important original that substitution terephthalic acid (TPA) is used for manufacturing ester plastic
Material manufactures the biodegradable plastic of the bis- terephthalate that birdss of the same feather flock together (PET) of a new generation；Its structure has five rings difunctional
Feature, compared with terephthalic acid (TPA) six-membered ring structure, have molecules align asymmetrical type, therefore can also be used to synthesizing optical/
Choke specific function high molecular material；2,5 furandicarboxylic acids are also used as the weight of other fine chemicals, drug and pesticide
Want intermediate.Therefore, the preparation of 2,5-furandicarboxylic acid is considered as the sustainable life of great representative substitution Petroleum Production
Object conversion process has very big application prospect and potentiality.
Lin Lu etc. (chemical reagent, 33,2011,11-12) is reported using alkalinity potassium permanganate aqueous solution chlorination 5- hydroxyl first
Base furfural (5-HMF) prepares FDCA.This method material concentration is low, and unit production capacity is low, simultaneously because aqueous slkali has been used, after causing
Continuous product separation must be added to a large amount of acid and FDCA products be precipitated to dissociate, and cause the generation of a large amount of abraum salt solution, environmental pollution big.
Lin Lu etc. is in patent CN 101891719A and Xu Jie etc. in patent CN 103626726A and CN 103724303A
In report in aqueous slkali, using oxygen as oxidant, use noble-metal-supported catalyst oxidation 5-HMF prepare FDCA.
This method equally exists the drawbacks of material concentration is low, product is precipitated in the acidification of follow-up needs.Patent CN104529957A is with 2,5-
Furans dicarbaldehyde is mixed and stirred for reacting with tert-Butanol peroxide aqueous solution, then cooled to room temperature, obtains reaction product；To anti-
Product is answered to centrifuge to obtain precipitation, washing is precipitated and dried to get target product 2,5-furandicarboxylic acid.It is used in the above method
Raw material be 5 hydroxymethyl furfural, oxidative synthesis 2,5-furandicarboxylic acid be broadly divided into metering oxidizing process, homogeneous catalysis method,
Heterogeneous catalysis method.It measures oxidizing process and uses KMnO4、N2O4、HNO3Deng be used as oxidant, oxidation conjunction is carried out to 5 hydroxymethyl furfural
At 2,5- furandicarboxylic acids.Environmental pollution is caused when these oxidant severe corrosion to equipment, discharge, it is excellent not have considerable application
Gesture.There is also metal salts to detach the shortcomings of difficult, bromine environmental pollution is heavy for the catalyst that homogeneous oxidizing method uses.In contrast, multiphase
The advantages such as catalysis method has environmental protection, product is easily isolated, catalytic efficiency is higher.Use the heterogeneous catalysts such as Au, Pt, Pd, 5- hydroxyls
The aldehyde radical of methyl furfural is first converted into carboxyl, forms 5- methylol -2- furancarboxylic acids；Subsequent hydroxyl continues to be oxidized to carboxyl,
Obtain 2,5- furandicarboxylic acids.Obtaining high yield 2,5-furandicarboxylic acid, there is difficulty, reaction to be easy to rest on 5- methylols-
The 2- furancarboxylic acid stages, and 5 hydroxymethyl furfural is used to prepare 2,5-furandicarboxylic acid for raw material, preparation method is relative complex.
Invention content
It is excellent it is an object of the invention to solve at least the above and/or defect, and provide at least to will be described later
Point.
In order to realize these purposes and other advantages according to the present invention, a kind of synthesis of 2,5-furandicarboxylic acid is provided
Method includes the following steps：
Step 1: by 2, organic solvent is added in 5- dimethyl furans and N- bromo-succinimides, and in the work of initiator
With lower generation bromo-reaction；Obtain bromination product 2,5- dibromo methylfurans；
Step 2: making bromination product 2 under the action of oxidant, oxidation reaction occurs for 5- dibromo methylfurans, obtains 2,
5- furandicarboxylic acids.
Preferably, the weight ratio of 2, the 5- dimethyl furans and organic solvent is 1~3:3~8；The 2,5- diformazans
The weight ratio of base furans and initiator is 1:0.01~0.05；The 2,5- dimethyl furans rub with N- bromo-succinimides
You are than being 1~3:2~5.
Preferably, the process of the bromo-reaction is：By 2,5- dimethyl furans, organic solvent, initiator, N- bromos
Succimide is added in the reactor with reflux, and heating is stirred to react 3~10h at reflux, drops naturally
Temperature；Reaction solution is depressurized and is filtered, filter cake is cleaned with carbon tetrachloride, and washing lotion merges with filtrate, and then concentrated by rotary evaporation removes solvent, obtains
Brown oil liquid, vacuum distillation purification, obtains 2,5- dibromo methylfurans.
Preferably, the process of the oxidation reaction is：Oxidant is added in the reactor with reflux condensing tube,
2,5- dibromo methylfurans are added under stirring, cool down after being stirred to react 5~10h at 80~100 DEG C, during cooling
Reaction solution becomes white opacity, and has gas overflowing；By after cooling white opacity reaction solution depressurize filter, filter cake spend from
Sub- water cleaning, obtains white powder, dry in vacuum drying oven, obtains 2,5-furandicarboxylic acid.
Preferably, the speed of the stirring is 150~280r/min.
Preferably, the oxidant is the concentrated nitric acid that mass fraction is 50~65%.
Preferably, the position of the gas overflowing be arranged tail gas absorption pipe, and by tail gas absorption pipe be passed through lye into
Promoting the circulation of qi body absorbs.
Preferably, the initiator is azodiisobutyronitrile or benzoyl peroxide.
Preferably, the organic solvent is one kind in carbon tetrachloride, chloroform, dichloro-benzenes, nitrobenzene, diazomethane.
Preferably, the weight ratio of 2, the 5- dibromos methylfuran and oxidant is 1:6~10.
The present invention includes at least following advantageous effect：With cheap 2,5- dimethyl furans for raw material, first bromo closes
At 2,5- dibromo methylfurans, then a step aoxidizes to obtain the target product 2,5-furandicarboxylic acid of high yield, this programme cost
Cheap, mild condition is easy to operate.
Part is illustrated to embody by further advantage, target and the feature of the present invention by following, and part will also be by this
The research and practice of invention and be understood by the person skilled in the art.
Description of the drawings：
Fig. 1 is the chemical equation of technical solution of the present invention.
Specific implementation mode：
With reference to embodiment, the present invention is described in further detail, to enable those skilled in the art with reference to specification
Word can be implemented according to this.
It should be appreciated that such as " having ", "comprising" and " comprising " term used herein do not allot one or more
The presence or addition of a other elements or combinations thereof.
Embodiment 1：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: by 2, organic solvent is added in 5- dimethyl furans and N- bromo-succinimides (NBS), and in initiator
Under the action of bromo-reaction occurs；Obtain bromination product 2,5- dibromo methylfurans；The 2,5- dimethyl furans with it is organic molten
The weight ratio of agent is 1:3；The weight ratio of the 2,5- dimethyl furans and initiator is 1:0.01；The 2,5- dimethyl furans
Molar ratio with N- bromo-succinimides is 1:2；
Step 2: making bromination product 2 under the action of oxidant, oxidation reaction occurs for 5- dibromo methylfurans, obtains 2,
5- furandicarboxylic acids；The weight ratio of the 2,5- dibromos methylfuran and oxidant is 1:6.
Embodiment 2：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: by 2, organic solvent is added in 5- dimethyl furans and N- bromo-succinimides, and in the work of initiator
With lower generation bromo-reaction；Obtain bromination product 2,5- dibromo methylfurans；The 2,5- dimethyl furans and organic solvent
Weight ratio is 1:8；The weight ratio of the 2,5- dimethyl furans and initiator is 1:0.05；The 2,5- dimethyl furans and N-
The molar ratio of bromo-succinimide is 1:3；
Step 2: making bromination product 2 under the action of oxidant, oxidation reaction occurs for 5- dibromo methylfurans, obtains 2,
5- furandicarboxylic acids；The weight ratio of the 2,5- dibromos methylfuran and oxidant is 1:10.
Embodiment 3：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: by 2, organic solvent is added in 5- dimethyl furans and N- bromo-succinimides, and in the work of initiator
With lower generation bromo-reaction；Obtain bromination product 2,5- dibromo methylfurans；The 2,5- dimethyl furans and organic solvent
Weight ratio is 1:5；The weight ratio of the 2,5- dimethyl furans and initiator is 1:0.03；The 2,5- dimethyl furans and N-
The molar ratio of bromo-succinimide is 1:2.5；
Step 2: making bromination product 2 under the action of oxidant, oxidation reaction occurs for 5- dibromo methylfurans, obtains 2,
5- furandicarboxylic acids；The weight ratio of the 2,5- dibromos methylfuran and oxidant is 1:8.
Embodiment 4：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: band is added in 2,5- dimethyl furans, carbon tetrachloride, azodiisobutyronitrile, N- bromo-succinimides
Have in the reactor of reflux, is at this time yellowish muddy shape, heats by medium of paraffin oil, be stirred to react at reflux
3h, at this time reaction solution become deep yellow turbid shape, Temperature fall；Reaction solution is depressurized and is filtered, filter cake cleans two with carbon tetrachloride
Secondary, washing lotion merges with filtrate, is yellow clear liquid, and then concentrated by rotary evaporation removes solvent, obtains brown oil liquid, vacuum distillation carries
It is pure, 2,5- dibromo methylfurans are obtained, are solidified at low temperature, are in faint yellow solid-state；The 2,5- dimethyl furans and four chlorinations
The weight ratio of carbon is 1:3；The weight ratio of the 2,5- dimethyl furans and azodiisobutyronitrile is 1:0.01；The 2,5- diformazans
The molar ratio of base furans and N- bromo-succinimides is 1:2；
Step 2: the concentrated nitric acid that mass fraction is 65% is added in the reactor with reflux condensing tube, in stirring shape
2,5- dibromo methylfurans are added under state, reaction solution is in yellowish clarification shape, is cooled down after being stirred to react 5h at 80 DEG C, in the mistake of cooling
Reaction solution becomes white opacity in journey, has a large amount of white powders to be precipitated, and entire reaction process has gas overflowing；After cooling down
The decompression of white opacity reaction solution filter, filter cake clean three times with deionized water, obtains white powder, dry in vacuum drying oven
It is dry, obtain 2,5-furandicarboxylic acid；The weight ratio of the 2,5- dibromos methylfuran and concentrated nitric acid is 1:6.
Embodiment 5：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: band is added in 2,5- dimethyl furans, carbon tetrachloride, azodiisobutyronitrile, N- bromo-succinimides
Have in the reactor of reflux, is at this time yellowish muddy shape, heats by medium of paraffin oil, be stirred to react at reflux
3h, at this time reaction solution become deep yellow turbid shape, Temperature fall；Reaction solution is depressurized and is filtered, filter cake cleans two with carbon tetrachloride
Secondary, washing lotion merges with filtrate, is yellow clear liquid, and then concentrated by rotary evaporation removes solvent, obtains brown oil liquid, vacuum distillation carries
It is pure, 2,5- dibromo methylfurans are obtained, are solidified at low temperature, are in faint yellow solid-state；The 2,5- dimethyl furans and four chlorinations
The weight ratio of carbon is 1:8；The weight ratio of the 2,5- dimethyl furans and azodiisobutyronitrile is 1:0.05；The 2,5- diformazans
The molar ratio of base furans and N- bromo-succinimides is 1:3；
Step 2: the concentrated nitric acid that mass fraction is 65% is added in the reactor with reflux condensing tube, in stirring shape
2,5- dibromo methylfurans are added under state, reaction solution is in yellowish clarification shape, is cooled down after being stirred to react 5h at 80 DEG C, in the mistake of cooling
Reaction solution becomes white opacity in journey, has a large amount of white powders to be precipitated, and entire reaction process has gas overflowing；After cooling down
The decompression of white opacity reaction solution filter, filter cake clean three times with deionized water, obtains white powder, dry in vacuum drying oven
It is dry, obtain 2,5-furandicarboxylic acid；The weight ratio of the 2,5- dibromos methylfuran and concentrated nitric acid is 1:10.
Embodiment 6：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: band is added in 2,5- dimethyl furans, carbon tetrachloride, azodiisobutyronitrile, N- bromo-succinimides
Have in the reactor of reflux, is at this time yellowish muddy shape, heats by medium of paraffin oil, be stirred to react at reflux
3h, at this time reaction solution become deep yellow turbid shape, Temperature fall；Reaction solution is depressurized and is filtered, filter cake cleans two with carbon tetrachloride
Secondary, washing lotion merges with filtrate, is yellow clear liquid, and then concentrated by rotary evaporation removes solvent, obtains brown oil liquid, vacuum distillation carries
It is pure, 2,5- dibromo methylfurans are obtained, are solidified at low temperature, are in faint yellow solid-state；The 2,5- dimethyl furans and four chlorinations
The weight ratio of carbon is 1:5；The weight ratio of the 2,5- dimethyl furans and azodiisobutyronitrile is 1:0.03；The 2,5- diformazans
The molar ratio of base furans and N- bromo-succinimides is 2:5；
Step 2: the concentrated nitric acid that mass fraction is 65% is added in the reactor with reflux condensing tube, in stirring shape
2,5- dibromo methylfurans are added under state, reaction solution is in yellowish clarification shape, is cooled down after being stirred to react 5h at 80 DEG C, in the mistake of cooling
Reaction solution becomes white opacity in journey, has a large amount of white powders to be precipitated, and entire reaction process has gas overflowing；After cooling down
The decompression of white opacity reaction solution filter, filter cake clean three times with deionized water, obtains white powder, dry in vacuum drying oven
It is dry, obtain 2,5-furandicarboxylic acid；The weight ratio of the 2,5- dibromos methylfuran and concentrated nitric acid is 1:8.
Embodiment 7：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: by 2,5- dimethyl furans 100g, carbon tetrachloride 500g, azodiisobutyronitrile 3.4g, N- bromo fourth two
Acid imide 389g is added in three mouthfuls of reactors of the 1000mL with reflux, and mechanical agitation is installed on three mouthfuls of reactors, this
When for yellowish muddy shape, be medium heating using paraffin oil, 6h be stirred to react with 200r/min at reflux, at this time reaction solution
Become deep yellow turbid shape, Temperature fall；Reaction solution is depressurized and is filtered, filter cake is cleaned twice with carbon tetrachloride, washing lotion and filtrate
Merge, be yellow clear liquid, then concentrated by rotary evaporation removes solvent, obtains brown oil liquid, and vacuum distillation purification obtains 2,5- dibromos
Methylfuran 171.7g, yield about 65% solidify under sterling low temperature, are in faint yellow solid-state；
Step 2: the concentrated nitric acid that 1376g mass fractions are 65% is added three mouthfuls of the 2000mL with reflux condensing tube
In reactor, mechanical agitation is installed on three mouthfuls of reactors, 2,5- dibromo methylfuran 171.7g are added under stirring, is reacted
Liquid is in yellowish clarification shape, is cooled down after being stirred to react 8h at 90 DEG C with 200r/min, and reaction solution becomes white during cooling
Muddiness has a large amount of white powders to be precipitated, and entire reaction process has gas overflowing；White opacity reaction solution after cooling is subtracted
Pressure filters, and filter cake is cleaned three times with deionized water, obtains white powder, dry in vacuum drying oven, obtains 2,5- furans diformazans
Sour 80.4g, yield about 76.2%.
Embodiment 8：
A kind of synthetic method of 2,5-furandicarboxylic acid, includes the following steps：
Step 1: by 2,5- dimethyl furans 200g, carbon tetrachloride 800g, azodiisobutyronitrile 4g, N- bromo succinyl
Imines 778g is added in three mouthfuls of reactors with reflux, installs mechanical agitation on three mouthfuls of reactors, is yellowish muddy at this time
Turbid shape heats by medium of paraffin oil, is stirred to react 8h at reflux with 250r/min, reaction solution becomes buff at this time
Muddy shape, Temperature fall；Reaction solution is depressurized and is filtered, filter cake is cleaned twice with carbon tetrachloride, and washing lotion merges with filtrate, is yellow
Clear liquid, then concentrated by rotary evaporation removing solvent, obtains brown oil liquid, and vacuum distillation purification obtains 2,5- dibromo methylfurans
359g, yield about 68% solidify under sterling low temperature, are in faint yellow solid-state；
Step 2: the concentrated nitric acid that 2872g mass fractions are 65% is added in three mouthfuls of reactors with reflux condensing tube,
Mechanical agitation is installed on three mouthfuls of reactors, 2,5- dibromo methylfuran 359g are added under stirring, reaction solution is in yellowish clear
Clear shape cools down after being stirred to react 8h at 90 DEG C with 200r/min, and reaction solution becomes white opacity during cooling, has a large amount of
White powder is precipitated, and entire reaction process has gas overflowing；White opacity reaction solution after cooling is depressurized and is filtered, filter cake
It is cleaned three times with deionized water, obtains white powder, it is dry in vacuum drying oven, obtain 2,5-furandicarboxylic acid 172g, yield
About 78%.
Although the embodiments of the present invention have been disclosed as above, but its is not only in the description and the implementation listed
With it can be fully applied to various fields suitable for the present invention, for those skilled in the art, can be easily
Realize other modification, therefore without departing from the general concept defined in the claims and the equivalent scope, the present invention is simultaneously unlimited
In specific details and example shown and described herein.
Claims (8)
1. a kind of synthetic method of 2,5-furandicarboxylic acid, which is characterized in that include the following steps：
Step 1: by 2, organic solvent is added in 5- dimethyl furans and N- bromo-succinimides, and under the action of initiator
Bromo-reaction occurs；Obtain bromination product 2,5- dibromo methylfurans；
Step 2: making bromination product 2 under the action of oxidant, oxidation reaction occurs for 5- dibromo methylfurans, obtains 2,5- furans
It mutters dioctyl phthalate；The oxidant is the concentrated nitric acid that mass fraction is 50~65%；The 2,5- dibromos methylfuran and oxidant
Weight ratio be 1:6~10.
2. the synthetic method of 2,5-furandicarboxylic acid as described in claim 1, which is characterized in that 2, the 5- dimethyl furans
Weight ratio with organic solvent is 1~3:3~8；The weight ratio of the 2,5- dimethyl furans and initiator is 1:0.01~
0.05；The molar ratio of the 2,5- dimethyl furans and N- bromo-succinimides is 1~3:2~5.
3. the synthetic method of 2,5-furandicarboxylic acid as described in claim 1, which is characterized in that the process of the bromo-reaction
For：The reactor with reflux is added in 2,5- dimethyl furans, organic solvent, initiator, N- bromo-succinimides
In, heating is stirred to react 3~10h, Temperature fall at reflux；Reaction solution is depressurized and is filtered, filter cake carbon tetrachloride is clear
It washes, washing lotion merges with filtrate, and then concentrated by rotary evaporation removes solvent, obtains brown oil liquid, and vacuum distillation purification obtains 2,5- bis-
Bromomethyl furans.
4. the synthetic method of 2,5-furandicarboxylic acid as described in claim 1, which is characterized in that the process of the oxidation reaction
For：Oxidant is added in the reactor with reflux condensing tube, 2,5- dibromo methylfurans are added under stirring, 80
~100 DEG C be stirred to react 5~10h after cool down, reaction solution becomes white opacity during cooling, and has gas overflowing；
White opacity reaction solution after cooling is depressurized and is filtered, filter cake is cleaned with deionized water, white powder is obtained, in vacuum drying oven
It is dry, obtain 2,5-furandicarboxylic acid.
5. the synthetic method of 2,5-furandicarboxylic acid as described in claim 3 or 4, which is characterized in that described to be stirred to react
Speed is 150~280r/min.
6. the synthetic method of 2,5-furandicarboxylic acid as claimed in claim 4, which is characterized in that in the position of the gas overflowing
Tail gas absorption pipe is installed, and tail gas absorption pipe is passed through lye and carries out gas absorption.
7. the synthetic method of 2,5-furandicarboxylic acid as described in claim 1, which is characterized in that the initiator is azo two
Isobutyronitrile or benzoyl peroxide.
8. the synthetic method of 2,5-furandicarboxylic acid as described in claim 1, which is characterized in that the organic solvent is tetrachloro
Change one kind in carbon, chloroform, dichloro-benzenes, nitrobenzene, diazomethane.
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| Effective Palladium-Catalyzed Hydroxycarbonylation of Aryl Halides with Substoichiometric Carbon Monoxide;Signe Korsager 等;《J. Am. Chem. Soc.》;20130211;第35卷;2891-2894 * |
| Lithiation Reaction of 2,5-Dibromothiophene 13C NMR Spectra of 3-Substituted Derivatives;Chiem van Pham 等;《J. Org. Chem.》;19841231;第49卷;5250-5253 * |
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