CN110158115A - A kind of method that electrochemistry prepares phenol - Google Patents
A kind of method that electrochemistry prepares phenol Download PDFInfo
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- CN110158115A CN110158115A CN201910338064.5A CN201910338064A CN110158115A CN 110158115 A CN110158115 A CN 110158115A CN 201910338064 A CN201910338064 A CN 201910338064A CN 110158115 A CN110158115 A CN 110158115A
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- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
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- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/055—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the substrate or carrier material
- C25B11/057—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the substrate or carrier material consisting of a single element or compound
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- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/055—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the substrate or carrier material
- C25B11/057—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the substrate or carrier material consisting of a single element or compound
- C25B11/061—Metal or alloy
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/073—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material
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- C25B11/073—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material
- C25B11/075—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound
- C25B11/081—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound the element being a noble metal
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- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
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Abstract
The present invention relates to a kind of methods that electrochemistry prepares phenol, including step 1): the acetonitrile solution of the benzene of concentration containing certain mass being added in alkaline electrolyte solution, keeps conductivity in 10mS/cm or more；Step 2): using metallic nickel compounds as anode electrode catalyst agent, to load the carbon material of platinum black as cathode electrode material；Step 3): anode voltage is applied by power supply, controls operating voltage and operating current；Step 4): electrolysis generates the Ni=O reactive intermediate of high activity, and a step aoxidizes benzene into phenol；Step 5): regulate and control the state and solubility of production phenol using the pH value of hydrochloric acid regulation water phase electrolyte；Step 6): extraction phenol product is synchronized by upper layer acetonitrile organic phase, and Pyrogentisinic Acid purifies, while organic extractant recycles.The beneficial effects of the present invention are: the present invention prepares phenol using one-pot oxidation benzene, have many advantages, such as that equipment investment is small, low energy consumption, high conversion rate, by-product is few, organic solvent is recyclable.
Description
Technical field
The present invention relates to distributing electrochemistry to prepare phenol field, and in particular to a kind of to prepare phenol using electrochemical method
Method.
Background technique
Phenol is most important organic and one of macromolecule chemical industry raw material, application mainly have phenolic resin, caprolactam,
Bisphenol-A, adipic acid, aniline, alkyl phenol, salicylic acid.Pesticide can be further produced using these chemical products, fragrance, dyestuff, killed
The high-value products such as microbial inoculum, anesthetic, preservative.Phenol is also used as solvent, reagent, widely used in scientific research.
The demand of market Pyrogentisinic Acid also increasingly increases in recent years, in supply falls short of demand state.
The industrial process of phenol mainly has cumene method, toluol-benzene formic acid method and benzene sulfonation method etc..Cumene method
Leading position is occupied in Phenol at Home industrial production, is technique more mature at present.But that there is energy consumptions is high for cumene method,
The problems such as low yield, by-product a large amount of acetone.Toluol-benzene formic acid method process flow is relatively simple, raw material, catalyst and product without
Poison, small investment, and the widely used chemical products such as benzoic acid, benzaldehyde and benzyl alcohol can be produced according to the market demand, but
Because the phenol generated cannot leave reactor, tar easily generated quickly, and then can give the use of the yield and catalyst of phenol
Service life brings certain influence.Since the price of toluene is higher than benzene, the production cost of toluene method is higher than cumene method, at present only
There is a few producer such as Chiba, Japan phenol company to carry out production phenol using this method.Benzene sulfonation method in preparation process because making
With a large amount of sulfuric acid and sodium hydroxide, the problems such as generating " three wastes " there are burn into, it is rarely employed in recent years.
Electrochemical method has the advantages that many significant.It is possible, firstly, to avoid using toxic or dangerous oxidant and reduction
Agent.Since electronics is clean reaction reagent, in reaction system, in addition to raw material and product, other reagents is typically free of, are reduced
Material consumption；And product is easily separated, with high purity, and environmental pollution is small.Second, during electrochemistry formated, electronics transfer and
Chemically reacting the two processes can carry out simultaneously, can effectively and continuously change electrode reaction speed by coordination electrode current potential
Degree, reduction side reaction, so that the yield of target product and selectivity are higher.Third, reaction can carry out under room temperature, normal pressure,
It generally is heated and pressurizeed equipment without special, has saved the energy, and reduce equipment investment.
Summary of the invention
The purpose of the present invention is to overcome the above shortcomings and to provide a kind of methods that electrochemistry prepares phenol.
The method that electrochemistry prepares phenol, includes the following steps:
The acetonitrile solution of the benzene of concentration containing certain mass is added in alkaline electrolyte solution by S1, and conductivity is kept to exist
10mS/cm or more；
S2, using metallic nickel compounds as anode electrode catalyst agent, to load the carbon material of platinum black as cathode electrode material
Material；
S3 applies anode voltage by power supply, controls operating voltage and operating current；
S4, electrolysis generate the Ni=O reactive intermediate of high activity, and a step aoxidizes benzene into phenol；
S5 regulates and controls the state and solubility of production phenol using the pH value of hydrochloric acid regulation water phase electrolyte,
S6 synchronizes extraction phenol product by upper layer acetonitrile organic phase, and Pyrogentisinic Acid purifies, while organic extractant returns
It receives.
As preferred: in the step S1, the concentration of benzene is 10%-30% in solution containing benzene acetonitrile.
As preferred: in the step S1, the alkaline electrolyte be sodium hydroxide, potassium hydroxide or cesium hydroxide, it is dense
Degree range is 0.1~1.0M.
As preferred: in the step S2, the working electrode is nickel foam.
As preferred: in the step S2, the working electrode is to load special nickel complex, and chemical formula is (Ni [N
(CH2(N C5H4))2CH2(NC6H3O2)H2O]Cl。
As preferred: in the step S3, the power supply is DC supply.
As preferred: in the step S3, voltage is 2~5V, and working current density is 1~8A/m2。
As preferred: in the step S5, using the pH value of hydrochloric acid regulation water phase electrolyte to pH=7.
As preferred: in the step S6, the phenol purifying method is circulating-heating or recrystallization.
As preferred: in the step S6, the organic extractant way of recycling is condensation.
The beneficial effects of the present invention are: the present invention prepares phenol using one-pot oxidation benzene, there is concise in technology, equipment to throw
Provide the advantages that small, low energy consumption, easy to operate, and high conversion rate, by-product are few, organic solvent is recyclable.
Detailed description of the invention
Fig. 1 is system flow chart；
Fig. 2 is the molecular structure for loading special nickel complex.
Description of symbols: anode conducting plate 1, anode material 2, heating plate 3, anodolyte 4, catholyte 5, yin
Pole conductive plate 6, organic extraction room 7, amberplex 8, cathode material 9, DC power supply 10, temperature controller 11, thermocouple 12, distillation
Separation chamber 13, product pond 14, Liquid guiding pump 15.
Specific embodiment
The present invention is described further below with reference to embodiment.The explanation of following embodiments is merely used to help understand this
Invention.It should be pointed out that for those skilled in the art, without departing from the principle of the present invention, also
Can be with several improvements and modifications are made to the present invention, these improvement and modification also fall into the protection scope of the claims in the present invention
It is interior.
Fig. 1 is system flow chart；
The system mainly by electrolytic cell part (anode conducting plate 1, anode material 2, heating plate 3, anodolyte 4,
Catholyte 5, cathode conductive plate 6, organic extraction room 7, amberplex 8, cathode material 9, DC power supply 10, temperature controller
11, thermocouple 12) and product separating-purifying part composition (distillation separation chamber 13, product pond 14, Liquid guiding pump 15).Electrolytic cell is main
By anode conducting plate 1, cathode conductive plate 6, anode material 2, cathode material 9, anodolyte 4, catholyte 5, You Jicui
Room 7 is taken, amberplex 8 and heating plate 3 are constituted.The specific working principle is as follows.Positive voltage is passed through anode by DC power supply 10
Conductive plate 1, cathode conductive plate 6 are added on anode material 2, generate Ni=O reactive intermediate, so that oxidation substrates benzene, generates and produce
Object phenol is extracted in the organic extraction room 7 on electrolytic cell anode upper layer, and is transferred out of electrolytic cell.Power supply is applied on cathode material 9
Add negative voltage, water is restored and generates byproduct hydrogen gas.Amberplex 8 between two electrodes can transmit the ion in solution,
Constitute complete electrical circuit.The optimum temperature of electrode reaction is between 80-90 DEG C, therefore in solar panel outer layer covers electric boiling plate
3, pass through the optimum temperature of temperature controller 11 and the control reaction of thermocouple 12.After the phenol of generation is transferred to distillery 13, pass through
Separation of Organic is distilled, pure phenol 14 is finally obtained.The organic solution distilled out can be transmitted back to electrolysis by Liquid guiding pump 15
Pond recycling.
Embodiment 1
Working electrode material is nickel foam, loads the carbon material of platinum black as cathode electrode material.By the benzene of 10% concentration
Acetonitrile solution 500mL, be added in the sodium hydroxide electrolyte of pH=13.Operating voltage is set as 3.0V, adjusts work electricity
Stream is 1A/m2.Working electrode area and electrolyte solution volume ratio are set as 1cm-2/1cm-3(100cm-2/100mL).Through electrification
After learning processing 10 hours, concentration of the phenol in water phase reaches 20g/L.In 10 hours electrolytic processes, average current effect
Rate is 40%, and the power consumption using this method production phenol is about 0.5kwh/kg.The selectivity of phenol is up to 90%, remaining by-product
Object is mainly hydroquinone and benzoquinone.
Embodiment 2
Working electrode material is nickel foam, loads the carbon material of platinum black as cathode electrode material.Select 20% concentration
The acetonitrile solution of benzene, is added in the sodium hydroxide electrolyte of pH=13.Operating voltage is set as 3.0V, adjusting operating current is
1.5A/m2.Working electrode area and electrolyte solution volume ratio are set as 1cm-2/1cm-3(100cm-2/100mL).Through electrochemistry
After processing 8 hours, concentration of the phenol in water phase reaches 20g/L.In 8 hours electrolytic processes, average current efficiency is
50%, the power consumption using this method production phenol is about 0.4kwh/kg.The selectivity of phenol reaches 90%, and Main By product is
Hydroquinone and benzoquinone.
Embodiment 3
Working electrode material is to load special nickel complex (Ni [N (CH as shown in Figure 22(N C5H4))2CH2(NC6H3O2)
H2O] Cl titanium alloy material, load the carbon material of platinum black as cathode electrode material.Select the acetonitrile of the benzene of 20% concentration molten
Liquid is added in the sodium hydroxide electrolyte of pH=13.Operating voltage is set as 3.0V, adjusting operating current is 1.0A/m2.Work
Make electrode area and electrolyte solution volume ratio is set as 1cm-2/1cm-3.After electrochemical treatments 12 hours, phenol is in water
Concentration in phase reaches 20g/L or more.In 12 hours electrolytic processes, average current efficiency 50% is raw using this method
The power consumption for producing phenol is about 0.75kwh/kg.The selectivity of phenol reaches 70%, and Main By product is hydroquinone, resorcinol
And benzoquinone.
The above one step Oxybenzene of electrochemical catalysis prepares the new method of phenol, had both improved the transformation efficiency of benzene, and had also realized
Emission reduction energy conservation, the target of Green Chemistry.
Claims (10)
1. a kind of method that electrochemistry prepares phenol, which comprises the steps of:
The acetonitrile solution of the benzene of concentration containing certain mass is added in alkaline electrolyte solution by S1, and conductivity is kept to exist
10mS/cm or more；
S2, using metallic nickel compounds as anode electrode catalyst agent, to load the carbon material of platinum black as cathode electrode material；
S3 applies anode voltage by power supply, controls operating voltage and operating current；
S4, electrolysis generate the Ni=O reactive intermediate of high activity, and a step aoxidizes benzene into phenol；
S5 regulates and controls the state and solubility of production phenol using the pH value of hydrochloric acid regulation water phase electrolyte；
S6 synchronizes extraction phenol product by upper layer acetonitrile organic phase, and Pyrogentisinic Acid purifies, while organic extractant recycles.
2. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S1, second containing benzene
The concentration of benzene is 10%-30% in nitrile solution.
3. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S1, the alkali
Property electrolyte be sodium hydroxide, potassium hydroxide or cesium hydroxide, concentration range be 0.1~1.0M.
4. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S2, the work
Making electrode is nickel foam.
5. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S2, the work
Make electrode to load special nickel complex, chemical formula is (Ni [N (CH2(N C5H4))2CH2(NC6H3O2)H2O]Cl。
6. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S3, the electricity
Source is DC supply.
7. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S3, voltage 2
~5V, working current density are 1~8A/m2。
8. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S5, utilize salt
The pH value of acid regulation water phase electrolyte is to pH=7.
9. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that in the step S6, the benzene
Phenol purification process is circulating-heating or recrystallization.
10. the method that electrochemistry according to claim 1 prepares phenol, which is characterized in that described to have in the step S6
Machine extractant way of recycling is condensation.
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| CN201910338064.5A CN110158115B (en) | 2019-04-25 | 2019-04-25 | Method for electrochemically preparing phenol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113529111A (en) * | 2021-06-30 | 2021-10-22 | 东华理工大学 | Process and device for preparing phenol by benzene through electrocatalysis |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3730872A (en) * | 1970-05-27 | 1973-05-01 | Rhone Poulenc Sa | Electric cells |
| US20020014417A1 (en) * | 2000-05-30 | 2002-02-07 | Adolf Kuehnle | Electrochemical cell for the oxidation of organic compounds, and electrocatalytic oxidation process |
| CN105951121A (en) * | 2016-05-27 | 2016-09-21 | 安庆师范大学 | Method for preparing phenol by ionic liquid assisted electric catalytic oxidation |
-
2019
- 2019-04-25 CN CN201910338064.5A patent/CN110158115B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3730872A (en) * | 1970-05-27 | 1973-05-01 | Rhone Poulenc Sa | Electric cells |
| US20020014417A1 (en) * | 2000-05-30 | 2002-02-07 | Adolf Kuehnle | Electrochemical cell for the oxidation of organic compounds, and electrocatalytic oxidation process |
| CN105951121A (en) * | 2016-05-27 | 2016-09-21 | 安庆师范大学 | Method for preparing phenol by ionic liquid assisted electric catalytic oxidation |
Non-Patent Citations (3)
| Title |
|---|
| BOLESLAW FLESZAR等: "AN ATTEMPT TO DEFINE BENZENE AND PHENOL ELECTROCHEMICAL OXIDATION MECHANISM", 《ELECTROCHIMICA ACTA》 * |
| KAZUO SASAKI等: "ELECTROLYTIC PRODUCTION OF PHENOLS FROM BENZENE USING Cu(I)/Cu(II) COUPLE", 《CHEMISTRY LETTERS》 * |
| YONG-JUN LIU等: "One-Step Hydroxylation of Benzene to Phenol Induced by Glow Discharge Plasma in an Aqueous Solution", 《PLASMA CHEM PLASMA PROCESS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113529111A (en) * | 2021-06-30 | 2021-10-22 | 东华理工大学 | Process and device for preparing phenol by benzene through electrocatalysis |
| CN113529111B (en) * | 2021-06-30 | 2023-10-27 | 东华理工大学 | Process and device for preparing phenol by using benzene through electric catalysis |
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