CN108299357A - A kind of preparation method of disubstituted furan compound - Google Patents
A kind of preparation method of disubstituted furan compound Download PDFInfo
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- CN108299357A CN108299357A CN201710021947.4A CN201710021947A CN108299357A CN 108299357 A CN108299357 A CN 108299357A CN 201710021947 A CN201710021947 A CN 201710021947A CN 108299357 A CN108299357 A CN 108299357A
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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
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- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of preparation method of formula (I) compound, the method includes the steps：In a solvent, it will contact and react with catalyst and oxidant, this method is simple and efficient, by-product is few, high income with the compound of formula (II) structure；Wherein, the structure of formula (I) and formula (II) compound difference is as follows：
Description
Technical field
The invention belongs to high-performance polymer monomers to prepare the technical field with chemical industry, medicine intermediate, and in particular, to
A kind of preparation method of disubstituted furan compound.
Background technology
2,5-furandicarboxylic acid because containing rigidity furan nucleus and contraposition diformyl structure, can be directly used for polyester,
The preparation of the high performance polymer such as epoxy resin, polyamide, polyurethane.The polymer prepared using furans diacid is in intensity, mould
Amount, creep resistant etc. have excellent mechanical property, while having higher glass transition temperature and heat distortion temperature.This
Outside, 2,5-furandicarboxylic acid or its carboxylate itself can also be used as industrial chemicals and medicine intermediate uses.2,5- furans at present
It mutters dioctyl phthalate or the main synthetic method of its carboxylate is with expensive 5 hydroxymethyl furfural (HMF) for raw material.This method
Low with gross production rate, raw material HMF prepares difficulty, of high cost, is difficult to realize the shortcomings that heavy industrialization is applied.Even if HMF systems
Standby process modification, yield improve, but the starting material for preparing HMF is fructose and glucose, is main raw-food material, if being used for
Large-scale industrial production certainly will break agri-food supply chains balance.
In conclusion there is an urgent need to a kind of at low cost, yield is high, is suitable for industrial synthesis 2,5-furandicarboxylic acid
Method.
Invention content
The present invention provides a kind of preparation method of formula (I) compound, the method includes the steps：In a solvent, will have
The compound for having formula (II) structure, contacts with catalyst and oxidant and reacts, wherein the structure of formula (I) compound is：
The structure of formula (II) compound is：
In formula, R1It is selected from the group：Acetyl group, methyl, methylol, formyl, carboxaldehyde radicals ,-COOAr, wherein Ar=C1-
The alkyl of C10；
R1 ' is selected from the group：Formyl, methyl formate base ,-COOAr, the wherein alkyl of Ar=C1-C10.
In another preferred example, R1And R1' can be same or different.
In another preferred example, the catalyst is selected from the group：Metal salt containing Co, Mn or Zr, NaBr, KBr,
LiBr, RuBr, CsBr, or combinations thereof；It is preferably chosen from the following group：Co carboxylates, Mn carboxylates, Zr carboxylates, NaBr, KBr,
LiBr, RuBr, CsBr, or combinations thereof.
In another preferred example, the metal salt containing cobalt is selected from the group：Cobalt acetate, cobaltous formate, Cobaltous propionate or its group
It closes.
In another preferred example, the metal salt containing manganese is selected from the group：Manganese acetate, formic acid manganese, Manganese dipropionate or its group
It closes.
In another preferred example, the catalyst is selected from the group：Cobalt acetate, manganese acetate, zirconium acetate, or combinations thereof.
In another preferred example, the catalysis is selected from the group：NaBr, KBr, LiBr, RuBr, CsBr, or combinations thereof.
In another preferred example, the catalyst is selected from the group：Cobalt acetate, manganese acetate, sodium bromide, or combinations thereof.
In another preferred example, the catalyst includes being selected from the group (a), (b) and the catalyst of optional (c)：(a)
Metal salt containing cobalt；(b) NaBr, KBr, LiBr, RuBr, CsBr, or combinations thereof；(c) metal salt containing manganese.
In another preferred example, in the catalyst, the component (a), (b) and the molar ratio of (c) is 1:0.5-
10:0.5-20。
In another preferred example, the oxidant is selected from the group：Oxygen, oxygen-containing gas (such as air), or combinations thereof.
In another preferred example, the solvent is selected from the group：The carboxylic acid of C1-C6, the acid anhydrides of C2-C12, water, or combinations thereof.
In another preferred example, the solvent is selected from the group：Formic acid, acetic acid, propionic acid, acetic anhydride, or combinations thereof.
In another preferred example, the solvent is acetic acid.
In another preferred example, the ratio between the catalyst and the compound mole of formula (II) structure are 0.1-10%.
In another preferred example, the ratio between the solvent and the compound mole of formula (II) structure are 1-20:1.
In another preferred example, the reaction temperature of the method is 150-250 DEG C.
In another preferred example, the reaction temperature of the method is 180-220 DEG C.
In another preferred example, the compound of formula (I) structure is selected from the group：2,5- diacetyls furans, 2- acetyl
Base -5- methylfurans, 2- acetyl group -5- hydroxymethylfurans, 2- acetyl group -5- furancarboxylic acids, 2- acetyl group -5- furfurals, 2- acetyl group -
5- methylfuroates, or combinations thereof.
In another preferred example, the compound of formula (I) structure is selected from the group：2,5- diacetyls furans, 2- acetyl
Base -5- methylfurans, or combinations thereof.
In another preferred example, the compound of the formula (II) structure is prepared by the following method：
Acylation reaction occurs with raw material selected from the group below and acetylation reagent, the change of described formula (II) structure is prepared
Close object：5- acetyl furans, 5- methylfurans, 5- hydroxymethylfurans, 5- furancarboxylic acids, 5- furfurals, 5- methylfuroates, or combinations thereof.
In another preferred example, the acetylation reagent is selected from the group：Acetic anhydride, chloroacetic chloride, or combinations thereof.
It should be understood that within the scope of the present invention, above-mentioned each technical characteristic of the invention and have in below (eg embodiment)
It can be combined with each other between each technical characteristic of body description, to form a new or preferred technical solution.As space is limited, exist
This no longer tires out one by one states.
Description of the drawings
Fig. 1 is 1 gained 2,5- furandicarboxylic acids of embodiment1H-NMR collection of illustrative plates.
Specific implementation mode
The present inventor after extensive and in-depth study, by largely screening, it has unexpectedly been found that with 2- acetyl furans
Conjunction object is raw material, and the method that the 2,5-furandicarboxylic acid of high-purity is prepared by oxidation reaction, this method is simple and efficient, by-product
Less, high income.Based on above-mentioned discovery, inventor completes the present invention.
Term
Term " alkyl of C1-C10 " refers to the straight chain containing 1-10 carbon atom or containing the alkyl of branch, such as methyl, third
Base, isopropyl etc..
Term " carboxylic acid of C1-C6 " refers to the carboxylic acid containing 1-10 carbon atom, such as formic acid, acetic acid.
Term " acid anhydrides of C2-C12 " refers to the acid anhydrides containing 2-12 carbon atom, such as acetic anhydride, butyric anhydride.
The preparation method of 2,5- furandicarboxylic acids
The present invention provides a kind of preparation method of formula (I) compound, the method includes the steps：In a solvent, will have
The compound for having formula (II) structure, contacts with catalyst and oxidant and reacts, wherein the structure of formula (I) compound is：
The structure of formula (II) compound is：
In formula, R1For substituent group selected from the group below：Acetyl group, methyl, methylol, formyl, carboxaldehyde radicals ,-COOAr,
The alkyl of middle Ar=C1-C10；
R1 ' is substituent group selected from the group below：Formyl, methyl formate base ,-COOAr, the wherein alkyl of Ar=C1-C10；
In another preferred example, R1And R1' can be identical or can also be different.
Used catalyst can be any one or more of catalyst as described below in the reaction.Preferably contain
The metal salt of Co, Mn or Zr or catalyst selected from the group below：NaBr, KBr, LiBr, RuBr, CsBr, or combinations thereof.Wherein,
The metal salt containing Co, Mn or Zr is preferably：Co carboxylates, Mn carboxylates, Zr carboxylates.The metal salt containing cobalt
It is preferably chosen from the following group：Cobalt acetate, cobaltous formate, Cobaltous propionate, or combinations thereof.The metal salt containing manganese is preferably chosen from the following group：
Manganese acetate, formic acid manganese, Manganese dipropionate, or combinations thereof.The metal salt containing zirconium is preferably zirconium acetate.
In preferred implement, the catalyst is selected from the group：Cobalt acetate, manganese acetate, zirconium acetate, or combinations thereof.More
Preferably, the catalyst is selected from the group：Cobalt acetate, manganese acetate, sodium bromide, or combinations thereof.
In another preferred example, the catalyst be include being selected from the group (a), (b) and the catalyst of optional (c)：
(a) metal salt containing cobalt；(b) NaBr, KBr, LiBr, RuBr, CsBr, or combinations thereof；(c) metal salt containing manganese.Wherein, described
Component (a), (b) and the molar ratio of (c) be preferably 1:0.5-10:0.5-20.
The oxidant being passed through in reaction is not particularly limited, and can be oxygen or oxygen containing gas (such as air), and
In the oxygen-containing gas, other compositions are not involved in reaction.
The solvent used in reaction can be solvent selected from the group below：The carboxylic acid of C1-C6, the acid anhydrides of C2-C12, water or its
Combination solvent.Preferably, the solvent is formic acid, acetic acid, propionic acid, acetic anhydride, or combinations thereof.Preferred solvent is acetic acid.
In preferred embodiment, the ratio between the catalyst and the compound mole of formula (II) structure are 0.1-10%.
The ratio between the solvent and the compound mole of formula (II) structure are 1-20:1.
In preferred embodiment, the method, which needs to heat, to be carried out, and preferred reaction temperature is 150-250 DEG C, more excellent
Choosing is 180-220 DEG C.
In preferred embodiment, the compound of formula (I) structure is compound selected from the group below：2,5- diacetyls
Furans, 2- acetyl group -5- methylfurans, 2- acetyl group -5- hydroxymethylfurans, 2- acetyl group -5- furancarboxylic acids, 2- acetyl group -5- chaffs
Aldehyde, 2- acetyl group -5- methylfuroates, or combinations thereof.It is highly preferred that the compound of formula (I) structure is 2,5- diacetyls
Furans, 2- acetyl group -5- methylfurans, or combinations thereof.
In preferred embodiment, the compound of the formula (II) structure is by with raw material selected from the group below and acetyl
Change reagent and acylation reaction occurs, the compound of described formula (II) structure is prepared.The raw material is：5- acetyl group furans
It mutters, 5- methylfurans, 5- hydroxymethylfurans, 5- furancarboxylic acids, 5- furfurals, 5- methylfuroates, or combinations thereof.Preferably, the second
Acylating reagent is：Acetic anhydride, chloroacetic chloride, or combinations thereof.
Using
Using the method for the invention, can high yield synthesis 2,5-furandicarboxylic acid.In addition, using of the present invention
The 2,5-furandicarboxylic acid of high-purity prepared by method can be used as high-performance polyester, epoxy resin, polyamide, polyurethane etc.
The raw material and industrial chemicals and medicine intermediate raw material of polymer.
Main advantages of the present invention include：
The preparation method of a kind of 2,5-furandicarboxylic acid of the present invention, with 2- acetyl group -5- furancarboxylic acids or its carboxylate
The 2,5-furandicarboxylic acid that high-purity is prepared for raw material, to get through by furan starting material compound synthesis high-performance engineering material
Technology path.Since furan starting material can drive biology base Polymer Material Industry gradually to break away from pair using biology base as source
The dependence of petroleum resources promotes the sustainable development of entire Polymer Material Industry.
The method of the invention is simple and efficient, flow is short, by-product is few, and product total recovery is up to 70%-99%, purity
Height is suitble to large-scale industrial production, can meet as polymer such as high-performance polyester, epoxy resin, polyamide, polyurethane
Raw material and requirement as industrial chemicals and medicine intermediate raw material.
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In the following examples, the experimental methods for specific conditions are not specified, usually according to conventional strip
Part, or according to the normal condition proposed by manufacturer.Unless otherwise stated, otherwise percentage and number are calculated by weight.
Universal method
In the following embodiments, nuclear magnetic resonance spectroscopy 1H-NMR uses the 400AVANCE of Brooker company (Bruker)
III type spectroscope (Spectrometer) measures, 400MHz, dimethyl sulfoxide DMSO.Product analysis uses agilent company
(Agilent) 7890B-5977A type liquid chromatograph-mass spectrometers detection.
Embodiment 1
In 500ml reactors, addition 3.08g 2- acetyl group -5- furancarboxylic acids, 15.6ml acetic acid, 2mmol cobalt acetates,
5mmol manganese acetates and 10mmol sodium bromides, are passed through oxygen, and 180 DEG C of reaction 6h filter the solid of precipitation and drying, obtain 2,5-
Furandicarboxylic acid, yield 88%.Through1H-NMR (400MHz, DMSO) tests obtain, CH on furan nucleus, 2H, δ (7.28)；Carboxyl
OH, 2H, δ (13.60), as shown in Figure 1, liquid chromatography mass spectrometric combined instrument (LC-MS) measures molecular weight 156.1.
Embodiment 2
In 500ml reactors, 3.08g 2- acetyl group -5- furancarboxylic acids, 7.8ml acetic acid, 4mmol cobalt acetates, 8mmol is added
Manganese acetate and 20mmol sodium bromides, are passed through air, and 200 DEG C of reaction 10h filter the solid of precipitation and drying, obtain 2,5- furans
Dioctyl phthalate, yield 85%.It is obtained through 1H-NMR (400MHz, DMSO) tests, CH on furan nucleus, 2H, δ (7.28)；Carboxyl OH,
2H, δ (13.60), liquid chromatography mass spectrometric combined instrument (LC-MS) measure molecular weight 156.1, and HPLC measures 2,5 furandicarboxylic acid purity and is
99.1%.
Embodiment 3
In 500ml reactors, 3.08g2- acetyl group -5- furancarboxylic acids, 3.9ml acetic acid, 8mmol cobalt acetates, 8mmol is added
Manganese acetate and 10mmol sodium bromides, are passed through oxygen, and 220 DEG C of reaction 8h filter the solid of precipitation and drying, obtain 2,5- furans two
Formic acid, yield 72%.It is obtained through 1H-NMR (400MHz, DMSO) tests, CH on furan nucleus, 2H, δ (7.28)；Carboxyl OH, 2H, δ
(13.60), liquid chromatography mass spectrometric combined instrument (LC-MS) measures molecular weight 156.1, and HPLC measures 2,5 furandicarboxylic acid purity and is
89.4%.
Embodiment 4
In 500ml reactors, addition 3.08g2- acetyl group -5- furancarboxylic acids, 31.2ml acetic acid, 8mmol cobalt acetates,
16mmol manganese acetates and 30mmol sodium bromides, are passed through oxygen, and 240 DEG C of reaction 6h filter the solid of precipitation and drying, obtain 2,5-
Furandicarboxylic acid, yield 98%.It is obtained through 1H-NMR (400MHz, DMSO) tests, CH on furan nucleus, 2H, δ (7.28)；Carboxyl
OH, 2H, δ (13.60), liquid chromatography mass spectrometric combined instrument (LC-MS) measure molecular weight 156.1, and HPLC measures 2,5 furandicarboxylic acid purity
It is 99.8%.
Embodiment 5
In 500ml reactors, 3.08g2- acetyl group -5- furancarboxylic acids, 31.2ml acetic acid, 1mmol cobalt acetates, 2mmol is added
Manganese acetate and 5mmol sodium bromides, are passed through air, and 260 DEG C of reaction 4h filter the solid of precipitation and drying, obtain 2,5- furans two
Formic acid, yield 84%.It is obtained through 1H-NMR (400MHz, DMSO) tests, CH on furan nucleus, 2H, δ (7.28)；Carboxyl OH, 2H, δ
(13.60), liquid chromatography mass spectrometric combined instrument (LC-MS) measures molecular weight 156.1, and HPLC measures 2,5 furandicarboxylic acid purity and is
99.3%.
Embodiment 6
In 500ml reactors, 3.08g2- acetyl group -5- furancarboxylic acids, 31.2ml acetic acid, 5mmol cobalt acetates, 6mmol is added
Manganese acetate and 10mmol sodium bromides, are passed through oxygen, and 150 DEG C of reaction 14h filter the solid of precipitation and drying, obtain 2,5- furans
Dioctyl phthalate, yield 78%.It is obtained through 1H-NMR (400MHz, DMSO) tests, CH on furan nucleus, 2H, δ (7.28)；Carboxyl OH,
2H, δ (13.60), liquid chromatography mass spectrometric combined instrument (LC-MS) measure molecular weight 156.1, and HPLC measures 2,5 furandicarboxylic acid purity and is
99.0%.
All references mentioned in the present invention is incorporated herein by reference, independent just as each document
It is incorporated as with reference to such.In addition, it should also be understood that, after reading the above teachings of the present invention, those skilled in the art can
To be made various changes or modifications to the present invention, such equivalent forms equally fall within model defined by the application the appended claims
It encloses.
Claims (10)
1. a kind of preparation method of formula (I) compound, which is characterized in that the method includes the steps：
In a solvent, it will contact and react with catalyst and oxidant with the compound of formula (II) structure,
Wherein, the structure of formula (I) compound is：
The structure of formula (II) compound is：
In formula, R1It is selected from the group：Acetyl group, methyl, methylol, formyl, carboxaldehyde radicals ,-COOAr, the wherein alkane of Ar=C1-C10
Base；
R1 ' is selected from the group：Formyl, methyl formate base ,-COOAr, the wherein alkyl of Ar=C1-C10.
2. the method as described in claim 1, which is characterized in that the catalyst is selected from the group：Metal containing Co, Mn or Zr
Salt, NaBr, KBr, LiBr, RuBr, CsBr, or combinations thereof；It is preferably chosen from the following group：Co carboxylates, Mn carboxylates, Zr carboxylic acids
Salt, NaBr, KBr, LiBr, RuBr, CsBr, or combinations thereof.
3. the method as described in claim 1, which is characterized in that the catalyst includes being selected from the group (a), catalysis (b)
Agent, and the optional catalyst for being selected from the group (c)：(a) metal salt containing cobalt；(b) NaBr, KBr, LiBr, RuBr, CsBr, or
A combination thereof；(c) metal salt containing manganese.
4. the method as described in claim 1, which is characterized in that the oxidant is selected from the group：Oxygen contains oxygen gas mixture
(such as air), or combinations thereof.
5. the method as described in claim 1, which is characterized in that the solvent is selected from the group：The carboxylic acid of C1-C6, C2-C12
Acid anhydrides, water, or combinations thereof.
6. the method as described in claim 1, which is characterized in that the compound mole of the catalyst and formula (II) structure it
Than for 0.1-10%.
7. the method as described in claim 1, which is characterized in that the ratio between the compound mole of the solvent and formula (II) structure
For 1-20:1.
8. the method as described in claim 1, which is characterized in that the reaction temperature of the method be 150-270 DEG C (preferably
150-250 DEG C).
9. the method as described in claim 1, which is characterized in that the compound of formula (I) structure is selected from the group：2,5- diethyls
Acyl group furans, 2- acetyl group -5- methylfurans, 2- acetyl group -5- hydroxymethylfurans, 2- acetyl group -5- furancarboxylic acids, 2- acetyl group -
5- furfurals, 2- acetyl group -5- methylfuroates, or combinations thereof.
10. the method as described in claim 1, which is characterized in that the compound of described formula (II) structure is by the following method
It prepares：
Acylation reaction occurs with raw material selected from the group below and acetylation reagent, the chemical combination of described formula (II) structure is prepared
Object：5- acetyl furans, 5- methylfurans, 5- hydroxymethylfurans, 5- furancarboxylic acids, 5- furfurals, 5- methylfuroates, or combinations thereof.
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| CN114621168A (en) * | 2022-03-14 | 2022-06-14 | 黄石市利福达医药化工有限公司 | Preparation method of furan-2, 5-dicarboxylic acid |
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