CN113121477A - Preparation method of 2, 5-tetrahydrofuran dicarboxylic acid - Google Patents
Preparation method of 2, 5-tetrahydrofuran dicarboxylic acid Download PDFInfo
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- CN113121477A CN113121477A CN202110614549.XA CN202110614549A CN113121477A CN 113121477 A CN113121477 A CN 113121477A CN 202110614549 A CN202110614549 A CN 202110614549A CN 113121477 A CN113121477 A CN 113121477A
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- tetrahydrofuran
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- dicarboxylic acid
- dimethanol
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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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
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- Organic Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Abstract
The invention relates to the technical field of organic matter synthesis, and particularly discloses a preparation method of 2, 5-tetrahydrofuran dicarboxylic acid, which comprises the steps of contacting a material containing 2, 5-tetrahydrofuran dimethanol with a catalyst and an oxygen source in a solvent, and reacting for 0.5-10 h at 20-130 ℃ to obtain the 2, 5-tetrahydrofuran dicarboxylic acid. The method has low requirements on raw materials, has wide adaptability to crude products of 2, 5-tetrahydrofuran dimethanol prepared by different production modes, has mild reaction temperature in the preparation process, can achieve high substrate conversion rate and product yield without high temperature and high pressure, does not need a catalyst or a noble metal catalyst in the prior art, and obviously reduces the industrial production cost. The method is simple to operate, and provides technical support and basis for large-scale industrial production of the 2, 5-tetrahydrofuran dicarboxylic acid.
Description
Technical Field
The invention relates to the technical field of organic matter synthesis, in particular to a preparation method of 2, 5-tetrahydrofuran dicarboxylic acid.
Background
Due to the increasing shortage of coal and petrochemical resources and the resulting environmental problems, the development of biomass energy has been receiving more and more attention. In recent years, platform compounds synthesized from biomass saccharide compounds as initial raw materials and various derivatives thereof, such as 5-hydroxymethylfurfural, 2, 5-furandimethanol, 2, 5-furandicarboxaldehyde, 2, 5-furandicarboxylic acid and the like, are expected to be widely applied to the fields of pharmaceutical intermediates, polyesters, lubricating oil, biofuels and the like, and become hot spots for research and development of biomass at present.
2, 5-tetrahydrofuran dicarboxylic acid (THFDCA) is a very promising target for development, and u.s.8501989 reports that 2, 5-tetrahydrofuran dicarboxylic acid can be partially converted to adipic acid in the presence of a hydrogenation catalyst, and that adipic acid can be converted to various useful downstream chemicals, including adipates, caprolactone, 1, 6-hexanediol, polyamides, and the like.
As an interesting attempt, CN111971274A discloses a method for synthesizing 2, 5-tetrahydrofuran dicarboxylic acid by catalyzing 2, 5-tetrahydrofuran dimethanol with a Pt/Bi catalyst. When the concentration of the substrate is 250g/L, after the heating reflux reaction is carried out for 16 hours under the condition of 150 ℃ under normal pressure in the air environment, the conversion rate of the 2, 5-tetrahydrofuran dimethanol is 70 percent, and the yield of the 2, 5-tetrahydrofuran dicarboxylic acid is 50 percent; however, if the reaction is heated for 16 hours after the temperature is reduced to 60 ℃, the generation of 2, 5-tetrahydrofuran dicarboxylic acid is not detected, the product is mainly monobasic acid 5-hydroxymethyl-2-carboxyl-tetrahydrofuran, and the yield of the monobasic acid reaches 89%, which indicates that most of 2, 5-tetrahydrofuran dimethanol is only oxidized into carboxyl by single hydroxymethyl. However, when the substrate concentration was reduced from 250g/L to 133.33g/L, and the reaction mixture was heated up to 150 ℃ for 3 hours at 6.9MPa (1000psi) of air using a high pressure environment, the conversion of tetrahydrofuran dimethanol was greater than 98%, with a yield of THFDCA of 87%.
Therefore, if a method for synthesizing 2, 5-tetrahydrofuran dicarboxylic acid under mild conditions by using a cheap non-noble metal catalyst can be developed, the method has very good application prospect and significance.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide a preparation method of 2, 5-tetrahydrofuran dicarboxylic acid, which is used for preparing the 2, 5-tetrahydrofuran dicarboxylic acid by using raw materials of 2, 5-tetrahydrofuran dimethanol or 2, 5-tetrahydrofuran dimethanol reaction liquid after rough processing, and has the advantages of mild reaction temperature, short reaction time and low energy consumption; the catalyst is metal oxide with non-noble metal as main component, and has the features of low cost, simple reaction system and suitability for industrial production.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
in a first aspect, the invention provides a preparation method of 2, 5-tetrahydrofuran dicarboxylic acid, comprising the steps of contacting a material containing 2, 5-tetrahydrofuran dimethanol with a catalyst and an oxygen source in a solvent, and reacting at 20-130 ℃ for 0.5-10 h to obtain the 2, 5-tetrahydrofuran dicarboxylic acid;
the catalyst is a metal oxide or a metal oxide and a halogen element, the metal oxide is selected from transition metals or rare earth lanthanide series metals or alkali metals, and specifically comprises at least one metal oxidation state or a plurality of metal oxidation state compounds or a plurality of metal oxidation state mixtures of Fe, Mn, Cu, Co, Zn, Ni, V, Zr, Nb, La, Ce and K; the halogen element is selected from at least one of Br and Cl;
the oxygen source is selected from one or more of air, oxygen, sodium hypochlorite and hydrogen peroxide;
the solvent includes at least one of water and N, N-dimethylformamide.
Preferably, the catalyst is prepared from single metal oxide or multi-metal components by simple compounding or a sol-gel method or a hydrothermal method.
Further preferably, the mass ratio of the material containing 2, 5-tetrahydrofuran dimethanol to the catalyst used in the preparation method of the invention is 1: 0.05 to 10.
More preferably, the catalyst is a nanoscale particle.
Further, the oxygen source is sodium hypochlorite or hydrogen peroxide, and the molar ratio of the material containing 2, 5-tetrahydrofuran dimethanol to the oxygen source is 1: 1-10; when the oxygen source is air or oxygen, the reaction pressure is 0.1-6 MPa.
Further preferably, the reaction temperature of the preparation method is preferably 40-90 ℃, and is milder than the synthesis temperature of the existing 2, 5-tetrahydrofuran dicarboxylic acid.
In the preparation method, a material with a content of 90-100 wt.% of 2, 5-tetrahydrofuran dimethanol is preferably used.
It should be noted that the raw material in the preparation method of the present invention is not limited to high-purity 2, 5-tetrahydrofuran dimethanol, and for better application to a material containing 2, 5-tetrahydrofuran dimethanol in industrial production, the material may be a reaction liquid for producing 2, 5-tetrahydrofuran dimethanol, and the composition may further contain a small amount of one or more of impurities such as 5-hydroxymethylfurfural, 2, 5-furan dimethanol, 5-methyl-tetrahydrofuran, 5-methyl-2-formyl-tetrahydrofuran, 5-methyl-2-hydroxymethyl-tetrahydrofuran, and the like.
Preferably, the mass ratio of the material containing the 2, 5-tetrahydrofuran dimethanol to the solvent is 1: 5 to 100.
Further, the preparation method specifically comprises the following steps:
(1) mixing a material containing 2, 5-tetrahydrofuran dimethanol with a solvent to obtain a solution C;
(2) and adding a catalyst and an oxygen source into the solution C, stirring, contacting and reacting to obtain the 2, 5-tetrahydrofuran dicarboxylic acid.
The raw materials or reagents involved in the invention are all common commercial products, and the operations involved are all routine operations in the field unless otherwise specified.
The above-described preferred conditions may be combined with each other to obtain a specific embodiment, in accordance with common knowledge in the art.
The invention has the beneficial effects that:
the invention provides a synthetic method of 2, 5-tetrahydrofuran dicarboxylic acid with low energy consumption and suitable for industrial production. The method has low requirements on raw materials, has wide adaptability to crude products of 2, 5-tetrahydrofuran dimethanol prepared by different production modes, has mild reaction temperature in the preparation process, can achieve high substrate conversion rate and product yield without high temperature and high pressure, does not need a catalyst or a noble metal catalyst in the prior art, and obviously reduces the industrial production cost. The method is simple to operate, and provides technical support and basis for large-scale industrial production of the 2, 5-tetrahydrofuran dicarboxylic acid.
Detailed Description
In order that the above objects, features and advantages of the present invention may be more clearly understood, a solution of the present invention will be further described below. It should be noted that the embodiments of the present invention and features of the embodiments may be combined with each other without conflict.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those described herein; it is to be understood that the embodiments described in this specification are only some embodiments of the invention, and not all embodiments.
Preferred embodiments of the present invention will be described in detail with reference to the following examples. It is to be understood that the following examples are given for illustrative purposes only and are not intended to limit the scope of the present invention. Various modifications and alterations of this invention will become apparent to those skilled in the art without departing from the spirit and scope of this invention.
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
In the embodiment of the invention, an 8860 high performance gas chromatograph of Agilent company and a 1260 high performance liquid chromatograph of Agilent company are respectively adopted for detecting 2, 5-tetrahydrofuran dimethanol (THFDM) and 2, 5-tetrahydrofuran dicarboxylic acid (THFDCA).
The conversion of 2, 5-Tetrahydrofurandiol (THFDM) and the yield of 2, 5-tetrahydrofurandioic acid (THFDCA) are calculated as follows:
EXAMPLE 1 Mono-Metal oxide catalyst
Weighing 23g of basic copper carbonate precursor, grinding, taking 60-80 mesh powder, roasting in a muffle furnace at 300 ℃ for 2h, cooling, and taking out for later use to obtain the copper oxide catalyst.
Weighing 1g of crude 2, 5-tetrahydrofuran dimethanol, 30ml of N, N-dimethylformamide and 2g of copper oxide catalyst, sealing the reaction kettle, opening and stirring for 20min, respectively replacing for 3 times by using 1MPa nitrogen and oxygen, and finally keeping the reaction pressure of the oxygen constant at 2MPa and reacting for 5h at 80 ℃. After the reaction was completed, the filtrate was filtered and analyzed, and it was found that the conversion of 2, 5-tetrahydrofuran dimethanol was 94% and the yield of 2, 5-tetrahydrofuran dicarboxylic acid was 80%.
EXAMPLE 2 Multi-Metal Oxidation State hybrid catalyst
The catalyst is prepared by simple compounding:
adding 4.7g of cobalt bromide, 5.5g of manganese bromide, 5g of 48 wt.% aqueous hydrobromic acid solution and 30ml of water into a 50ml beaker, and uniformly mixing and oscillating to obtain Co2+/Mn2+/Br-Mixed catalyst solution of multi-metal oxidation state.
Weighing 0.4g of NaOH, dissolving in 30mL of deionized water, adding 0.4g of 2, 5-tetrahydrofuran dimethanol, and simply compounding with Co2+/Mn2+/Br-1g of the mixed catalyst solution in the oxidation state of the polymetallic, sealing the reaction kettle, opening the reaction kettle and stirring for 20min, simultaneously introducing air, keeping the reaction pressure constant at 2MPa, and reacting for 4h at 90 ℃. After the reaction was completed, the filtrate was filtered and analyzed, and it was found that the conversion of 2, 5-tetrahydrofuran dimethanol was 97% and the yield of 2, 5-tetrahydrofuran dicarboxylic acid was 87%.
Example 3 Multi-Metal composite oxide catalyst
Preparing a catalyst by a sol-gel method:
34.7376g of cerium nitrate and 8.5864g of zirconium nitrate are weighed into an aqueous solution, 19.212g of citric acid is added, the pH is adjusted, after 5 hours of reaction, rotary steaming, drying, grinding and roasting at 600 ℃ for 2 hours are carried out, and the cerium oxide-zirconium oxide composite catalyst is prepared.
Weighing 1.2g of NaOH and dissolving in 100mL of deionized water, sequentially adding 1.3g of 90 wt.% of crude 2, 5-tetrahydrofuran dimethanol, 1.1g of cerium oxide-zirconium oxide composite catalyst and 9g of 30% hydrogen peroxide solution, and reacting the reaction mixture at 20 ℃ for 1 h. After the reaction, the filtrate was filtered and analyzed, and it was found that the conversion of 2, 5-tetrahydrofuran dimethanol was 90% and the yield of 2, 5-tetrahydrofuran dicarboxylic acid was 72%.
EXAMPLE 4 Multi-Metal oxide catalyst
Preparation of the catalyst by a hydrothermal method:
weighing 5g of potassium permanganate, 6g of manganous sulfate and 8g of cobalt nitrate in a hydrothermal reaction kettle, preparing a mixed solution of 5ml of concentrated sulfuric acid and 70ml of water, slowly dripping the mixed solution into the hydrothermal reaction kettle, placing the hydrothermal reaction kettle at 130 ℃ for reaction for 24 hours, taking out the hydrothermal reaction kettle, washing, carrying out suction filtration and drying to obtain the K/Mn/Co/O catalyst.
Weighing 1.2g of NaOH and dissolving in 100mL of deionized water, adding 1.3g of 2, 5-tetrahydrofuran dimethanol, 2.1g of K/Mn/Co/O catalyst and 40g of 7.5% sodium hypochlorite solution in sequence, and reacting the reaction mixture at 40 ℃ for 2 h. After the reaction, the filtrate was filtered and analyzed, and it was found that the conversion of 2, 5-tetrahydrofuran dimethanol was 99% and the yield of 2, 5-tetrahydrofuran dicarboxylic acid was 91%.
The foregoing are merely exemplary embodiments of the present invention, which enable those skilled in the art to understand or practice the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. The preparation method of 2, 5-tetrahydrofuran dicarboxylic acid is characterized in that a material containing 2, 5-tetrahydrofuran dimethanol is contacted with a catalyst and an oxygen source in a solvent and reacts at the temperature of 20-130 ℃ for 0.5-10 h to obtain the 2, 5-tetrahydrofuran dicarboxylic acid;
the catalyst is a metal oxide or a metal oxide and a halogen element, the metal oxide is selected from transition metals or rare earth lanthanide series metals or alkali metals, and specifically comprises at least one metal oxidation state or a plurality of metal oxidation state compounds or a plurality of metal oxidation state mixtures of Fe, Mn, Cu, Co, Zn, Ni, V, Zr, Nb, La, Ce and K; the halogen element is selected from at least one of Br and Cl;
the oxygen source is selected from one or more of air, oxygen, sodium hypochlorite and hydrogen peroxide;
the solvent includes at least one of water and N, N-dimethylformamide.
2. The preparation method according to claim 1, wherein the catalyst is prepared from a single metal oxide or a multi-metal component by simple compounding or by a sol-gel method or a hydrothermal method.
3. The preparation method according to claim 1, wherein the mass ratio of the material containing 2, 5-tetrahydrofuran dimethanol to the catalyst is 1: 0.05 to 10.
4. The method of claim 3, wherein the catalyst is a nano-sized particle.
5. The preparation method of claim 1, wherein the oxygen source is sodium hypochlorite or hydrogen peroxide, and the molar ratio of the material containing 2, 5-tetrahydrofuran dimethanol to the oxygen source is 1: 1 to 10.
6. The preparation method according to claim 1, wherein the oxygen source is air or oxygen, and the reaction pressure is 0.1-6 MPa.
7. The method of claim 1, wherein the reaction temperature is preferably 40 ℃ to 90 ℃.
8. The preparation method according to any one of claims 1 to 7, wherein the mass content of 2, 5-tetrahydrofuran dimethanol in the material containing 2, 5-tetrahydrofuran dimethanol is 90 to 100 wt.%.
9. The preparation method according to any one of claims 1 to 7, wherein the mass ratio of the material containing 2, 5-tetrahydrofuran dimethanol to the solvent is 1: 5 to 100.
10. The method of manufacturing according to claim 9, comprising the steps of:
(1) mixing a material containing 2, 5-tetrahydrofuran dimethanol with a solvent to obtain a solution C;
(2) and adding a catalyst and an oxygen source into the solution C, stirring, contacting and reacting to obtain the 2, 5-tetrahydrofuran dicarboxylic acid.
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