CN114481170B - Method for synthesizing furoic acid by furfural in linear paired electrochemical manner - Google Patents

Method for synthesizing furoic acid by furfural in linear paired electrochemical manner Download PDF

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CN114481170B
CN114481170B CN202210077731.0A CN202210077731A CN114481170B CN 114481170 B CN114481170 B CN 114481170B CN 202210077731 A CN202210077731 A CN 202210077731A CN 114481170 B CN114481170 B CN 114481170B
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furfural
cathode
carbon
furoic acid
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CN114481170A (en
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林海波
李欣欣
丛林川
林楠
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Jilin University
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    • C25B3/00—Electrolytic production of organic compounds
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Abstract

The invention belongs to the field of electrochemical conversion of biomass derivatives, and discloses a method for synthesizing furoic acid by furfural in a linear paired electrochemical manner. The invention utilizes a flow type diaphragm electrochemical reactor, in an aqueous electrolyte, furfural is anode oxidized into furoic acid through an oxidation-reduction medium, and hydrogen peroxide is generated in situ through an oxygen reduction reaction at a cathode to convert furfural into furoic acid. The invention realizes the electrode process of multiple mediation on the anode and cathode by using one raw material furfural, and simultaneously obtains the same product furoic acid, has good compatibility of two-electrode reaction, can reach 200% of theoretical current efficiency, and greatly improves the electronic efficiency. This linear paired electrosynthesis method is of great significance to the field of electromechanical synthesis. The anode medium can be recycled in the electrosynthesis process, and the cathode oxidation medium hydrogen peroxide is nontoxic and harmless, so that the biomass green conversion in the true sense can be realized, and the method is a green electrochemical synthesis route with commercial prospect.

Description

Method for synthesizing furoic acid by furfural in linear paired electrochemical manner
Technical Field
The invention belongs to the technical field of biomass derivative synthesis, and particularly relates to a method for synthesizing furoic acid by furfural in a linear paired electrochemical manner.
Background
Furoic Acid (FA), also known as α -furoic acid, is a very important organic synthetic raw material. Furoic acid esters can be used as solvents or preparing varnishes, and can also be used as bactericides, pesticides and the like; the furfuryl amide prepared from furoic acid can be used as intermediate of medicine and spice, food preservative and plastic plasticizer; the furoic acid can be used for synthesizing various products such as cation exchange resin, etc. At present, the process for producing furoic acid is mainly a Cannizzaro reaction route of furfural (FF) and sodium hydroxide, and has the defects of a large amount of furfuryl alcohol generated as a byproduct and poor atomic economy.
Electrochemical catalytic biomass conversion is an important method for synthesizing high value-added chemicals. To date, some methods for the electrooxidation synthesis of furoic acid from furfural have been reported in the literature. It has been demonstrated that noble metal catalysts (e.g., pt, ag, au, etc.) can electrochemically oxidize furfural to furoic acid, with Gong et al (Journal of Catalysis,373, 2019, 322-335) indicating that electro-oxidation of furfural preferentially yields furoic acid at a potential of 0.9V vs RHE on the Pt electrode>80% selectivity), however, the use of noble metals is costly, limiting the progress of the reaction. Liu et al (Green Chemistry,23, 2021, 4034-4043) used non-noble metal NiCoMnLDHs nanoplatelets as electrocatalysts, resulting in Ni (OH) due to strong metal-oxygen interactions 2 The formation of/Ni (O) OH, the electrode stability is poor, a high conversion of furfural to furoic acid is maintained only within 2.5h, greatly limiting their application.
The paired electrosynthesis methods have been attracting attention because they use both anodic oxidation and cathodic reduction to produce products with high added value, theoretically up to 200% electrolytic efficiency. Therefore, in an electrochemical reactor, the two valuable half reactions are paired, so that the utilization rate of current can be greatly improved, and the energy consumption can be reduced. In addition, paired electrosynthesis methods may be economically viable by reducing the cost of operation by reducing the use of reactors or the necessary processing steps.
To date, research into paired electrosynthesis has focused more on divergent paired electrosynthesis in which two products are synthesized from one reactant at the cathode and anode, respectively. Part et al (Electrochimica Acta,49, 2004, 397-403) performed paired electrolysis in furfural alkaline electrolyte through nickel anode and copper cathode, respectively obtaining furoic acid and furfuryl alcohol at the cathode and anode, but the electrode had serious corrosion problem in electrolyte, excessive metal ions in electrolyte and difficult separation. Zhang et al (Applied Catalysis B: environmental,244, 2019, 899-908) in Ni 2 P/CFC as anode and Cu 3 P/CFC is used as cathode, H-type electrochemical reactor is used to obtain furfuryl alcohol and furoic acid in the electrolyte of cathode and anode, but the anode is electrically reactedThe bit and cathode potentials are high and severe water splitting side reactions occur in the electrolyte, resulting in reduced conversion and faraday efficiency. Chinese patent CN101649465 proposes a bipolar membrane technology, in which furfuryl alcohol and furoic acid are prepared simultaneously at the cathode and anode containing electrolytes with different pH, but the use of lead anode inevitably makes the solution have heavy metal ion residues, which makes the subsequent treatment difficult.
In recent years, with the continuous progress of the organic electronic synthesis technology, the efficient green paired electronic synthesis technology plays an increasingly important role. The linear paired electrosynthesis starts from the same reactant, and the electrocatalytic reaction path is changed by completely different electrosynthesis modes, so that the same product is obtained at the cathode and anode. This approach is no longer a mechanical pairing of simple redox reactions, but rather a new type of electrosynthesis system is built. The invention creatively provides a linear paired electrosynthesis method, furoic acid is synthesized from furfural through a cathode-anode multi-dielectric electrode process, and the specific invention content is as follows: using a diaphragm type electrochemical reactor to carry out electrolysis, and respectively taking electrode materials with catalytic functions as a cathode and an anode; the anode liquid contains supporting electrolyte, redox medium, water and furfuraldehyde, the cathode liquid contains supporting electrolyte, water and furfuraldehyde, oxygen is continuously introduced into the cathode chamber in the electrolysis process, and furfuraldehyde in the electrolyte is converted into furfuroic acid in both the cathode chamber and the anode chamber.
Disclosure of Invention
The invention aims to construct a method for synthesizing furoic acid by furfural through linear paired electrochemistry, which enables furfural to generate the same product furoic acid at the cathode and anode of a diaphragm electrolytic cell and solves the problems of low current efficiency and high energy consumption of the traditional furoic acid electrosynthesis method. The method uses the catalytic electrode in the water-based electrolyte through the multi-mediated electrode process, can realize the electrochemical conversion of the cathode and the anode at a lower potential at the same time, avoids the use of the noble metal electrode, and greatly reduces the production cost. The linear paired electrosynthesis method breaks the limitation of the traditional paired electrosynthesis, realizes the full utilization of electric energy, has advantages in the aspects of atom economy and availability, and accords with the concept of green chemistry.
The invention is realized by the following technical scheme:
using a diaphragm type electrochemical reactor to carry out electrolysis, and respectively taking electrode materials with catalytic functions as a cathode and an anode; the anode liquid contains supporting electrolyte, redox medium, water and furfuraldehyde, the cathode liquid contains supporting electrolyte, water and furfuraldehyde, oxygen is continuously introduced into the cathode chamber in the electrolysis process, and furfuraldehyde in the electrolyte is converted into furfuroic acid in both the cathode chamber and the anode chamber.
The redox mediator in the anolyte is potassium iodide, potassium bromide, potassium chloride, ferrocene, mn 3+ /Mn 2+ 、Ce 4+ /Ce 3+ One of TEMPO and 4-acetamido-TEMPO, the concentration of the redox mediator is 0.01-0.5 mol/L.
As a more preferable technical scheme of the invention: a flow type plate-frame diaphragm electrolytic cell with a gas diffusion flow passage is used, and the diaphragm is a cation exchange membrane.
As a more preferable technical scheme of the invention: the cathode is a gas diffusion electrode.
As a more preferable technical scheme of the invention: the gas diffusion electrode is prepared by compounding a carbon-based catalytic layer and a current collector.
As a more preferable technical scheme of the invention: the carbon-based catalytic layer is one or more of carbon oxide nanotubes, acetylene black, oxidized activated carbon and rice hull-based capacitance carbon; the current collector is one of foam nickel, foam titanium, foam carbon, foam copper, stainless steel mesh and carbon paper.
As a more preferable technical scheme of the invention: the anode is one of a graphite electrode, a glassy carbon electrode and a titanium-based metal oxide coating electrode.
As a more preferable technical scheme of the invention: the supporting electrolyte of the cathode and the anode is one of sodium hydroxide, potassium hydroxide, phosphate buffer solution and carbonate buffer solution, and the concentration of the supporting electrolyte is 0.1-1 mol/L;
as a more preferable technical scheme of the invention: the concentration of furfural in the cathode electrolyte and the anode electrolyte is 0.01-0.5 mol/L.
As a more preferable technical scheme of the invention: the anode and the cathode support potassium hydroxide with electrolyte of 0.1-0.5 mol/L, furfural of 0.02-0.05 mol/L and potassium iodide with redox mediator of 0.02-0.04 mol/L.
As a more preferable technical scheme of the invention: electrolysis is carried out by adopting a constant current mode, and the current density is 10-100mA/cm 2 The cell voltage variation range is 2-5V, the electrolysis temperature is 20-70 ℃, and the end point of the electrolysis reaction is determined according to 100-150% of the theoretical electric quantity of the reaction. More preferably, the current density is 20 to 80mA/cm 2 The electrolysis temperature is 40-50 ℃, and the end point of the electrolysis reaction is determined according to 130-150% of the theoretical electric quantity of the reaction.
As a more preferable technical scheme of the invention: the carbon-based catalytic layer is prepared by adding carbon nano tubes, acetylene black, active carbon or rice hull-based capacitance carbon into nitric acid with the concentration of 12-15 mol/L, refluxing at 60-80 ℃ for 24-48 h, filtering, washing to be neutral, and vacuum drying at 60-80 ℃ for 12-24 h.
Compared with the prior art, the invention has the beneficial effects that:
the method adopts a linear paired electrosynthesis method, and furoic acid is synchronously prepared in the anode and cathode chambers through multiple redox media in the anode and cathode processes, so that compared with the traditional paired electrosynthesis process, the method avoids the use of noble metal catalysts, reduces the cost, and more importantly, solves the problems of low current efficiency and high energy consumption of the traditional furoic acid electrosynthesis method. By using a green sustainable paired electrosynthesis method, single efficient conversion from furfural to furoic acid is realized in the cathode and anode of the same reactor, wherein the electron efficiency of the anode is 75-90%, the electron efficiency of the cathode is 55-95%, and the total electron efficiency is 130-185%; compared with monopolar electrosynthesis and other paired electrosynthesis methods, the total electronic efficiency and the total yield are greatly improved, and the method has good commercialization prospect.
Drawings
FIG. 1 is a schematic diagram of the method of the present invention, wherein Med represents a mediator, the superscript R represents a reduced state, and R represents an oxidized state.
Detailed Description
The invention is further illustrated by means of the following examples, without limiting the scope of the invention to the examples described.
Example 1:
preparation of cathode carbon-based catalytic layer
Adding 2g of carbon nano tube, acetylene black, active carbon and rice hull-based capacitance carbon into 15mol/L nitric acid respectively, stirring to form uniform suspension, oxidizing for 24 hours in a reflux device at 60 ℃, then carrying out suction filtration on the obtained suspension respectively, washing with water to be neutral, and finally carrying out vacuum drying at 60 ℃ for 12 hours to obtain carbon oxide nano tube, acetylene black oxide, active carbon oxide and rice hull-based capacitance carbon powder respectively. And respectively rolling the carbon nano tube into sheets, and then compounding the sheets with a current collector to prepare the carbon oxide nano tube gas diffusion electrode, the acetylene black gas diffusion electrode, the oxidized active carbon gas diffusion electrode and the oxidized rice hull-based capacitance carbon gas diffusion electrode.
Example 2:
the invention adopts a flowing plate-frame electrochemical reactor with a Nafion117 proton exchange membrane as a diaphragm, supports KOH with electrolyte of 0.1mol/L, furfuraldehyde with anolyte (40 mL) of 0.04mol/L and potassium iodide with anolyte (40 mL) of 0.04mol/L, and furfuraldehyde with catholyte (40 mL) of 0.04 mol/L. With graphite plates (2X 2 cm) 2 ) As anode, oxidized rice husk based capacitance carbon gas diffusion electrode (2X 2 cm) 2 ) Is a cathode. At 25 ℃, 30mA/cm in constant current electrolysis mode 2 And (3) electrolysis is carried out for 1h, oxygen is continuously introduced into the cathode solution during the electrolysis, the cell voltage is controlled to be 2-3V, the total yield of furoic acid is 85%, and the electronic efficiency is 150%.
Example 3:
the invention adopts a flowing plate-frame electrochemical reactor with a Nafion117 proton exchange membrane as a diaphragm, supports NaOH with electrolyte of 0.1mol/L, anode liquid (30 mL) of furfural with 0.02mol/L and potassium iodide with 0.04mol/L, and cathode liquid (50 mL) of furfural with 0.02 mol/L. With graphite plates (3X 3 cm) 2 ) As anode, a diffusion electrode (3X 3 cm) 2 ) Is a cathode. At 40 ℃,50 mA/cm in constant current electrolysis mode 2 And electrolysis is carried out for 2 hours, oxygen is continuously introduced into the cathode solution during the electrolysis, the cell voltage is controlled to be 3-4V, the total yield of furoic acid is 72%, and the electronic efficiency is 123%.
Example 4:
the invention adopts a flowing plate-frame electrochemical reactor with Nafion117 proton exchange membrane as a diaphragm, and supports Na with electrolyte of 0.2mol/L 2 HPO 4 -NaH 2 PO 4 Buffer solution (pH=8), anolyte (50 mL) of 0.04mol/L furfural and 0.02mol/L potassium iodide, catholyte (30 mL) of 0.15mol/L furfural. With glassy carbon electrodes (1X 1 cm) 2 ) Is used as anode, and oxidized carbon nano tube gas diffusion electrode (1X 1cm 2 ) Is a cathode. At 50 ℃, 40mA/cm in constant current electrolysis mode 2 And electrolysis is carried out for 0.5h, oxygen is continuously introduced into the cathode solution during the electrolysis, the cell voltage is controlled to be 2.5-3.5V, the total yield of furoic acid is 58%, and the electronic efficiency is 175%.
Example 5:
the invention adopts a flowing plate-frame electrochemical reactor with Nafion117 proton exchange membrane as a diaphragm, and supports Na with electrolyte of 0.2mol/L 2 CO 3 -NaHCO 3 Buffer solution (ph=10), anolyte (30 mL) of 0.1mol/L furfural and TEMPO of 0.2mol/L, catholyte (30 mL) of 0.1mol/L furfural, and high-purity oxygen gas was introduced into the catholyte for 30min before electrolysis to saturate oxygen. With graphite plates (3X 3 cm) 2 ) Is used as anode, and is used as oxidation active carbon gas diffusion electrode (3X 3cm 2 ) Is a cathode. At 25 ℃, in a constant current electrolysis mode, at 60mA/cm 2 And electrolysis is carried out for 2.5 hours, oxygen is continuously introduced into the cathode solution during the electrolysis, the cell voltage is controlled to be 4.3-4.8V, the total yield of furoic acid is 69%, and the electronic efficiency is 165%.
Example 6:
the invention adopts a flowing plate-frame electrochemical reactor with a Nafion117 proton exchange membrane as a diaphragm, supports KOH with electrolyte of 0.1mol/L, adopts anolyte (60 mL) of 0.01mol/L furfural and TEMPO with electrolyte of 0.02mol/L, and adopts catholyte (30 mL) of 0.04mol/L furfural. With graphite plates (3X 3 cm) 2 ) Is used as anode, and oxidized carbon nano tube gas diffusion electrode (3X 3cm 2 ) Is a cathode.At 25 ℃, in constant current electrolysis mode at 45mA/cm 2 And electrolysis is carried out for 1h, oxygen is continuously introduced into the cathode solution during the electrolysis, the cell voltage is controlled to be 3.3-3.9V, the total yield of furoic acid is 74%, and the electronic efficiency is 152%.
Example 7:
the invention adopts a flowing plate-frame electrochemical reactor with a Nafion117 proton exchange membrane as a diaphragm, supports KOH with electrolyte of 0.1mol/L, anode liquid (60 mL) is furfural with 0.04mol/L and potassium bromide with 0.1mol/L, and cathode liquid (30 mL) is furfural with 0.04 mol/L. With graphite plates (3X 3 cm) 2 ) Is used as anode, and oxidized carbon nano tube gas diffusion electrode (3X 3cm 2 ) Is a cathode. At 25 ℃, 100mA/cm in constant current electrolysis mode 2 And electrolysis is carried out for 1h, oxygen is continuously introduced into the cathode solution during the electrolysis, the cell voltage is controlled to be 4.6-5.3V, the total yield of furoic acid is 60%, and the electronic efficiency is 130%.

Claims (6)

1. A method for synthesizing furoic acid by furfural in linear paired electrochemistry is characterized in that the method comprises the following steps: using a diaphragm electrochemical reactor to electrolyze, and respectively taking electrode materials with catalytic functions as a cathode and an anode; the anode liquid contains supporting electrolyte, redox medium, water and furfuraldehyde, the cathode liquid contains supporting electrolyte, water and furfuraldehyde, oxygen is continuously introduced into the cathode chamber in the electrolysis process, and furfuraldehyde in the electrolyte is converted into furfuroic acid in both the cathode chamber and the anode chamber;
the cathode is a gas diffusion electrode, the gas diffusion electrode is prepared by adopting a mode of compounding a carbon-based catalytic layer and a current collector, the carbon-based catalytic layer is one or more of carbon oxide nanotubes, acetylene black, oxidized activated carbon and rice hull-based capacitance carbon, and the current collector is one of foam nickel, foam titanium, foam carbon, foam copper, stainless steel mesh and carbon paper; the anode is one of a graphite electrode, a glassy carbon electrode and a titanium-based metal oxide coating electrode;
the redox mediator in the anolyte is potassium iodide, potassium bromide, potassium chloride, ferrocene, mn 3+ /Mn 2+ 、Ce 4+ /Ce 3+ TEMPO, 4-ethylOne of the amido-TEMPO has a redox mediator concentration of 0.01-0.5 mol/L.
2. The method for linear paired electrochemical synthesis of furoic acid from furfural according to claim 1, wherein the diaphragm-type electrochemical reactor is a flow-type plate-frame diaphragm cell with gas diffusion channels, and the diaphragm is a cation exchange membrane.
3. The method for electrochemical synthesis of furoic acid from furfural in linear paired according to claim 1, wherein: the supporting electrolyte of the cathode electrolyte is one of sodium hydroxide, potassium hydroxide, phosphate buffer solution and carbonate buffer solution, and the concentration of the supporting electrolyte is 0.1-1 mol/L.
4. The method for electrochemical synthesis of furoic acid from furfural in linear paired according to claim 1, wherein: the concentration of furfural in the cathode electrolyte and the anode electrolyte is 0.01-0.5 mol/L.
5. The method for synthesizing furoic acid by linear paired electrochemical synthesis of furfurol according to claim 1, wherein electrolysis is carried out by adopting a constant current mode, and the current density is 10-100mA/cm 2 The cell voltage is 2-5V, the electrolysis temperature is 20-70 ℃, and the end point of the electrolysis reaction is determined according to 100-150% of the theoretical electric quantity of the reaction.
6. The method for synthesizing furoic acid by furfural in linear paired electrochemical manner according to claim 1, wherein the carbon-based catalytic layer is prepared by adding carbon nanotubes, acetylene black, activated carbon or rice hull-based capacitance carbon into 10-15 mol/L nitric acid, refluxing at 50-80 ℃ for 24-48 h, filtering, washing to neutrality, and vacuum drying at 40-80 ℃ for 12-24 h.
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CN109837555A (en) * 2019-04-11 2019-06-04 浙江工业大学 A kind of method that nickel vanadium phosphide catalyst electrocatalytic oxidation produces 2,5- furandicarboxylic acid
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