CN114438525B - Method for synthesizing furoic acid by electrochemical conversion of furfuraldehyde cathode - Google Patents
Method for synthesizing furoic acid by electrochemical conversion of furfuraldehyde cathode Download PDFInfo
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- CN114438525B CN114438525B CN202210078150.9A CN202210078150A CN114438525B CN 114438525 B CN114438525 B CN 114438525B CN 202210078150 A CN202210078150 A CN 202210078150A CN 114438525 B CN114438525 B CN 114438525B
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Abstract
The invention belongs to the technical field of organic electronic synthesis, and discloses a method for synthesizing furoic acid by electrochemical conversion of a furfuraldehyde cathode. The invention uses a diaphragm type electrolytic tank, adopts a gas diffusion cathode, generates hydrogen peroxide in situ through oxygen cathode reduction to oxidize furfural to obtain furoic acid, takes oxygen as a raw material in the process, is environment-friendly, avoids the use of a noble metal homogeneous catalyst and the subsequent separation steps, truly realizes the greenization of the synthesis process, is an environment-friendly new process, and has important significance for the development of the electromechanical synthesis technology.
Description
Technical Field
The invention belongs to the technical field of organic electronic synthesis, and particularly relates to a method for synthesizing furoic acid by electrochemical conversion of a furfuraldehyde cathode.
Technical Field
Furoic Acid (FA), also known as α -furoic acid, is a very important organic synthetic raw material. Furoic acid is an organic acid substance, and can be esterified with alcohol to form furoic acid ester. These esters are useful as solvents, in the preparation of varnishes, as fungicides, insecticides and the like, and as toughening agents for plastics and synthetic resins. The furfuryl amide prepared from furoic acid can be used as food preservative, plastic plasticizer and intermediate of medicine and perfume. Furoic acid can also be used for synthesizing various products such as cation exchange resin, and the like, and also can be used as a raw material for producing mometasone furoate.
Industrially, furoic acid is prepared by the Cannizzaro reaction of furfural (FF) under the condition of strong alkali, furoic acid is obtained after furoic acid acidification, and the reaction process is accompanied with the generation of a large amount of furfuryl alcohol as a byproduct, as shown below.
At present, various technological studies for preparing furoic acid by oxidizing furfural have been reported, M.Douthwaite et al (Catalysis sciencece&Technology,7, 2017, 5284-5293) uses 1% AuPd/Mg (OH) 2 As a heterogeneous catalyst, the selectivity of furoic acid is improved by utilizing the synergistic effect of palladium and gold nanoparticles, but the use of noble metals Au and Pd greatly improves the cost of the reaction. Yang et al (Industrial Crops and Products,153, 2020, 112580) used biocatalysis to carry out the bioconversion of furfural to furoic acid using recombinant escherichia coli, but the biological oxidation activity was pH sensitive, requiring metal ion additives, and the biological reaction process and subsequent treatments were cumbersome. Chinese patent CN111217775a prepares furoic acid by using dicarboximide compounds as oxidation catalysts, but this reaction requires high temperature and high pressure conditions and the use of toxic and harmful organic solvents. Chinese patent CN110845456B developed a microchannel reactor using Al on the inner wall of the capillary 2 O 3 The superfine powder loaded nano copper oxide is used as a catalyst, and continuous production of furoic acid is realized through control of reaction, but the process has higher requirements on the manufacturing process of the reactor, and the titration speed is required to be controlled. These high cost, high energy consumption, high pollution synthetic methods motivated us to develop alternatives to furfural oxidation. The use of green oxidants such as molecular oxygen or hydrogen peroxide is a very promising approach. The hydrogen peroxide is used as an oxidant which is green, safe, low in cost, easy to obtain and has atom economy, and has great attraction to the chemical industry.
Electrochemical catalytic conversion of biomass to high value-added chemicals can be achieved by heterogeneous electron transfer between the electrode and the reactant (direct electrolysis) or using redox catalysts (indirect electrolysis). Hydrogen peroxide, a high potential redox reagent, has many unique properties, it is readily soluble in water and is non-toxic. Since the decomposition products are only water and oxygen, the formation of any hazardous waste is not involved during use, and it has a strong oxidizing power, facilitating the subsequent chemical reactions to take place in the cathodic solution. The method is characterized in that the active hydrogen peroxide is generated by cathode oxygen reduction, furfuraldehyde is further converted into furfuroic acid in situ, furfuraldehyde electrochemical-chemical one-step green preparation of furfuroic acid is realized, the concept of green chemistry is met, the economy is good, and the method has potential commercial value.
Disclosure of Invention
The invention aims to construct a method for synthesizing furoic acid by hydrogen peroxide in-situ generation of hydrogen peroxide and conversion of furoic acid, which solves the problems of noble metal catalysis, complex operation, environmental pollution and the like in the traditional synthesis method. Compared with the traditional preparation method, the method has the advantages of good atom economy, greenness and obviously improved product purity and yield.
The invention is realized by the following technical scheme:
the invention creatively provides a method for synthesizing furoic acid by electrochemical conversion of a furfuraldehyde cathode. The hydrogen peroxide generated in situ at the cathode is used as a medium to mediate the oxidation reaction of furfural, the current efficiency reaches 50-95%, and the product yield reaches 50-80%. The reaction process does not use toxic and harmful reagents, and has the advantages of readily available raw materials and simple operation.
The above synthesis method for converting furfuraldehyde cathode electrochemistry into furfuroic acid comprises the following steps:
A. electrode catalytic layer preparation: mixing a carbon material and a binder according to the proportion of (1-7) (3-1), performing ultrasonic dispersion in an ethanol solution, stirring and heating to paste at 60-90 ℃, rolling into sheets, and vacuum drying at 45-60 ℃ for 12-24 hours to obtain an electrode catalytic layer;
B. preparation of a gas diffusion electrode: rolling and compounding the electrode catalytic layer and a current collector treated by a binder, calcining for 0.1-2 h in an inert gas atmosphere at 270-370 ℃, and naturally cooling to obtain a gas diffusion electrode;
C. electrochemical reactor: carrying out electrolysis by using a diaphragm type electrochemical reactor, wherein the diaphragm is a cation exchange membrane;
D. electrolyte solution: electrolyte is 0.01-1 mol/L electrolyte solution, and 0.01-1 mol/L furfural is added into the catholyte;
E. electrolytic conditions: continuously blowing oxygen into the gas diffusion cathode to ensure oxygen saturation in the electrolysis process, wherein the oxygen flow rate is 20-200ml/min, and the constant-voltage electrolysis time is 0.5-5 h; the electrolysis potential is a constant value between-1.0 and 0.2V vs. RHEThe potential and the current change range is 20-200 mA/cm 2 The temperature of the electrolyte is 20-70 ℃.
As a more preferable technical scheme of the invention: in the step A, the carbon material is one of rice hull-based porous carbon, carbon oxide nano tube and Pb/C composite material.
As a more preferable technical scheme of the invention: in the step A, the binder is polytetrafluoroethylene.
As a more preferable technical scheme of the invention: in the step B, the current collector is one of carbon paper, stainless steel mesh, foam nickel and foam titanium.
As a more preferable technical scheme of the invention: in the step B, the binder loading of the current collector subjected to the binder treatment is 30-60 mg.
As a more preferable technical scheme of the invention: in the step B, the pressure of the rolling compounding of the catalytic layer and the current collector is 8-12 MPa;
as a more preferable technical scheme of the invention: in the step C, the diaphragm type electrochemical reactor takes the titanium-based metal oxide coating as an anode and self-made gas diffusion electrode as a cathode.
As a more preferable technical scheme of the invention: in the step D, the electrolyte is a KOH solution with the concentration of 0.1-0.5 mol/L, and 0.01-0.5mol/L of furfural is added into the catholyte.
As a more preferable technical scheme of the invention: and E, in the electrolysis process, electrolysis is carried out for 2 hours under the condition of-0.5 to-0.1V vs. RHE, the current change range is 30-60 mA, and the temperature of electrolyte is 25-60 ℃.
Compared with the prior art, the invention has the beneficial effects that:
compared with the traditional preparation process, the method does not need high temperature and high pressure, only uses clean electrons and in-situ generated clean reagent hydrogen peroxide as an oxidant, avoids the use of a high-cost noble metal catalyst, generates byproducts only including oxygen and water in the reaction process, accords with the principle of green chemistry, reduces the complicated step of separating a subsequent catalyst from a substrate, shows good atomic economy, really realizes clean and efficient production, and has important significance for the development of an electromechanical synthesis technology.
Drawings
FIG. 1 is a schematic diagram of the method of the present invention.
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:
mixing carbon oxide nanotube and PTFE at a mass ratio of 2:1, adding 50mL ethanol, ultrasound for 30min, heating at 80deg.C to ointment, rolling into sheet, vacuum drying at 60deg.C for 24 hr to obtain electrode catalyst layer, and treating with PTFE-treated stainless steel mesh (1×1 cm) 2 ) Rolling and compounding under the pressure of 6MPa, calcining for 0.5h at 270 ℃ in a tubular furnace under the argon atmosphere, and naturally cooling to obtain a gas diffusion cathode; in the H-type reactor, the electrolyte is 0.1mol/L KOH solution, a self-made gas diffusion electrode is taken as a cathode, a titanium-based ruthenium-titanium-tin ternary oxide coating electrode is taken as an anode, and electrolysis is carried out at 40 ℃. 0.015mol/L furfural is added into the catholyte as a reactant, and the mixture is continuously stirred. Continuously bubbling oxygen into the gas diffusion electrode to ensure oxygen saturation, and electrolyzing for 1h under-0.2V vs. RHE, wherein the current change range is 30-45 mA, the furoic acid yield is 62%, and the current efficiency is 93%.
Example 2:
mixing rice hull-based capacitance carbon and PTFE at a mass ratio of 5:1, adding 50mL ethanol, ultrasonic treating for 30min, heating at 80deg.C to ointment, rolling to sheet, vacuum drying at 60deg.C for 24 hr to obtain electrode catalyst layer, and treating with PTFE-treated foam nickel (1×1 cm) 2 ) Rolling and compounding under the pressure of 4MPa, calcining for 0.2h at 300 ℃ in a tube furnace under the argon atmosphere, and naturally cooling to obtain a gas diffusion cathode; in the H-type reactor, the electrolyte is 0.1mol/L KOH solution, a self-made gas diffusion electrode is taken as a cathode, a titanium-based ruthenium-titanium-tin ternary oxide coating electrode is taken as an anode, and electrolysis is carried out at 50 ℃. Furfural of 0.015mol/L is added into the catholyte as a reactant, and stirring is continued. Continuously directing qiThe body diffusion electrode is blown with oxygen to ensure oxygen saturation, electrolysis is carried out for 2 hours under the condition of-0.4V vs. RHE, the current change range is 40-45 mA, the furoic acid yield is 75%, and the current efficiency is 89%.
Example 3:
mixing graphene and PTFE at a mass ratio of 1:4, adding 50mL ethanol, ultrasound for 30min, heating at 80deg.C to ointment, rolling into sheet, vacuum drying at 60deg.C for 24 hr to obtain electrode catalyst layer, and mixing with PTFE-treated carbon paper (1×1 cm) 2 ) Rolling and compounding under the pressure of 3MPa, calcining for 1h at 330 ℃ in a tube furnace under the argon atmosphere, and naturally cooling to obtain a gas diffusion cathode; in the H-type reactor, the electrolyte is Na of 0.2mol/L 2 HPO 4 -NaH 2 PO 4 The buffer solution (ph=8) was electrolyzed at 30 ℃ with a self-made gas diffusion electrode as cathode and a titanium-based ruthenium-titanium-tin ternary oxide coated electrode as anode. 0.02mol/L furfural is added into the catholyte as a reactant, and the mixture is continuously stirred. Continuously bubbling oxygen into the gas diffusion electrode to ensure oxygen saturation, and electrolyzing for 1h under-0.1V vs. RHE, wherein the current change range is 40-50 mA, the furoic acid yield is 63%, and the current efficiency is 80%.
Example 4:
mixing acetylene black and PTFE at a mass ratio of 7:1, adding 50mL ethanol, ultrasonic treating for 30min, heating at 80deg.C to ointment, rolling into sheet, vacuum drying at 60deg.C for 24 hr to obtain electrode catalyst layer, and treating with PTFE-treated titanium foam (1×1 cm) 2 ) Rolling and compounding under the pressure of 6MPa, calcining for 1.5 hours at 350 ℃ in a tube furnace under the argon atmosphere, and naturally cooling to obtain a gas diffusion cathode; in the H-type reactor, the electrolyte is Na of 0.2mol/L 2 CO 3 -NaHCO 3 The buffer solution (ph=10) was electrolyzed at 60 ℃ with the titanium-based ruthenium-titanium-tin ternary oxide coated electrode as the anode. 0.04mol/L furfural is added into the catholyte as a reactant, and the mixture is continuously stirred. Continuously bubbling oxygen into the gas diffusion electrode to ensure oxygen saturation, and electrolyzing for 2.5 hours under the condition of-0.1V vs. RHE, wherein the current change range is 30-45 mA, the furoic acid yield is 59.5%, and the current efficiency is 83%.
Example 5:
mixing active carbon and PTFE at a mass ratio of 1:4, adding 50mL ethanol, ultrasound for 30min, heating to 80deg.C, rolling into sheet, vacuum drying at 60deg.C for 24 hr to obtain electrode catalyst layer, and mixing with PTFE-treated titanium foam (1×1 cm) 2 ) Rolling and compounding under the pressure of 6MPa, calcining for 2 hours at 370 ℃ in a tube furnace under the argon atmosphere, and naturally cooling to obtain a gas diffusion cathode; in the H-type reactor, the electrolyte is 0.1mol/L KOH solution, a self-made gas diffusion electrode is taken as a cathode, a titanium-based ruthenium-titanium-tin ternary oxide coating electrode is taken as an anode, and the electrolysis is carried out at room temperature. 0.05mol/L furfural is added into the catholyte as a reactant, and the mixture is continuously stirred. Continuously bubbling oxygen into the gas diffusion electrode to ensure oxygen saturation, and electrolyzing for 2 hours under the condition of-0.4V vs. RHE, wherein the current change range is 45-60 mA, the furoic acid yield is 70%, and the current efficiency is 85%.
Claims (6)
1. The method for synthesizing furoic acid by electrochemical conversion of furfural cathode is characterized by comprising the following steps:
A. electrode catalytic layer preparation: mixing a carbon material and a binder in a ratio of (1-7) (3-1), performing ultrasonic dispersion in an ethanol solution, stirring and heating to paste at 60-90 ℃, rolling into a sheet, and performing vacuum drying at 45-60 ℃ for 12-24 hours to obtain an electrode catalytic layer; the carbon material is one or more of activated carbon, rice hull-based porous carbon, graphite, acetylene black, carbon nanotubes, carbon oxide nanotubes, graphene, pb/C composite material and rice hull-based capacitance carbon;
B. preparation of a gas diffusion electrode: rolling and compounding the electrode catalytic layer and a current collector treated by a binder, calcining for 0.1-2 h in an inert gas atmosphere at the calcining temperature of 250-370 ℃, and naturally cooling to obtain a gas diffusion electrode;
C. electrochemical reactor: carrying out electrolysis by using a diaphragm type electrochemical reactor, wherein the diaphragm is a cation exchange membrane; the diaphragm type electrochemical reactor takes a gas diffusion electrode as a cathode, a titanium-based metal oxide coating electrode as an anode, and a diaphragm as a cation exchange membrane;
D. electrolyte solution: the electrolyte is electrolyte solution of 0.01-1 mol/L, and furfural of 0.01-1 mol/L is added into the catholyte;
E. electrolytic conditions: continuously blowing oxygen into the gas diffusion electrode to ensure oxygen saturation in the electrolysis process, wherein the oxygen flow rate is 20-200mL/min, and the constant-voltage electrolysis time is 0.5-5 h; the electrolysis potential is a constant potential between-2.0 and 0.2V vs. RHE, and the current change range is 20-200 mA/cm 2 The temperature of the electrolyte is 20-70 ℃.
2. The method for synthesizing furoic acid by electrochemical conversion of furfural cathode according to claim 1, wherein in the step a, the binder is one or more of sodium carboxymethyl cellulose, styrene-butadiene rubber emulsion and polytetrafluoroethylene.
3. The method for synthesizing furoic acid by electrochemical conversion of furfural cathode according to claim 1, wherein in the step B, the current collector is one of carbon paper, stainless steel mesh, foam nickel, foam titanium and foam carbon.
4. The method for synthesizing furoic acid by electrochemical conversion of furfural cathode according to claim 1, wherein in the step B, the load of the catalytic layer of the current collector treated by the binder is 5-60 mg.
5. The method for synthesizing furoic acid by electrochemical conversion of furfural cathode according to claim 1, wherein in the step B, the pressure of rolling and compounding the catalytic layer and the current collector is 2-12 MPa.
6. The method for synthesizing furoic acid by electrochemical conversion of furfural cathode according to claim 1, wherein in the step D, the electrolyte solution is one of sodium hydroxide, potassium hydroxide, phosphate buffer solution and carbonate buffer solution.
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| US9598780B2 (en) * | 2015-01-08 | 2017-03-21 | Wisconsin Alumni Research Foundation | Electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and 2,5-diformylfuran |
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| CN101649465A (en) * | 2009-09-18 | 2010-02-17 | 福建师范大学 | Method for simultaneously preparing furfuryl alcohol and furoic acid on the basis of bipolar membrane technology |
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| CN112778251A (en) * | 2019-11-05 | 2021-05-11 | 中国石油化工股份有限公司 | Preparation method of furoic acid |
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| CN111217775A (en) * | 2020-03-23 | 2020-06-02 | 中国科学技术大学 | Method for preparing furoic acid from furfural |
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