EP3649278A1 - Procédé électrochimique de production de carbonates de diaryle - Google Patents

Procédé électrochimique de production de carbonates de diaryle

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Publication number
EP3649278A1
EP3649278A1 EP18750100.2A EP18750100A EP3649278A1 EP 3649278 A1 EP3649278 A1 EP 3649278A1 EP 18750100 A EP18750100 A EP 18750100A EP 3649278 A1 EP3649278 A1 EP 3649278A1
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EP
European Patent Office
Prior art keywords
oxide
electrocatalyst
ruthenium
copper
gas diffusion
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP18750100.2A
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German (de)
English (en)
Inventor
Vinh Trieu
Stefanie Eiden
Dana KAUBITZSCH
Jan HEIJL
Niklas Meine
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Intellectual Property GmbH and Co KG
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Covestro Deutschland AG
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Publication date
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Publication of EP3649278A1 publication Critical patent/EP3649278A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/23—Oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/01—Preparation of esters of carbonic or haloformic acids from carbon monoxide and oxygen
    • 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
    • C25B11/02—Electrodes; Manufacture thereof not otherwise provided for characterised by shape or form
    • C25B11/03—Electrodes; Manufacture thereof not otherwise provided for characterised by shape or form perforated or foraminous
    • C25B11/031—Porous electrodes
    • 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
    • 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
    • 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
    • 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
    • C25B11/089—Alloys
    • 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
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/29—Coupling reactions

Definitions

  • the invention relates to an electrochemical process for the preparation of diaryl carbonates.
  • Diaryl carbonates are important precursors in the production of polycarbonates and are therefore of great economic importance.
  • the preparation of aromatic polycarbonates by the melt transesterification method is known and described, for example, in “Schnell", Chemistry and Physics of Polycarbonates, Polymer Reviews, Vol. 9, Interscience Publishers, New York, London, Sydney 1964, in D.C. Prevorsek, B.T. Debona and Y. Kersten, Corporate Research Center, Allied Chemical Corporation, Moristown, New Jersey 07960, "Synthesis of Poly (ester) Carbonate Copolymer” in Journal of Polymer Science, Polymer Chemistry Edition, Vol. 19, 75-90 (1980). , in D. Freitag, U. Grigo, PR
  • diaryl carbonates used in the melt transesterification process for aromatic polycarbonates, e.g. through the interfacial process is described in principle in the literature, see e.g. in Chemistry and Physics of Polycarbonates, Polymer Reviews, H. Schnell, Vol. 9, John Wiley and Sons, Inc. (1964), p. 50/51.
  • the diaryl carbonate is prepared by reacting phenol with a carbonyl dihalide (e.g., phosgene) prepared from carbon monoxide.
  • a carbonyl dihalide e.g., phosgene
  • diaryl carbonates used in the melt transesterification process for aromatic polycarbonates, e.g. through the interfacial process is described in principle in the literature, see e.g. in Chemistry and Physics of Polycarbonates, Polymer Reviews, H. Schnell, Vol. 9, John Wiley and Sons, Inc. (1964), p. 50/51.
  • the diaryl carbonate is prepared by reacting phenol with a carbonyl dihalide (e.g., phosgene) prepared from carbon monoxide.
  • a carbonyl dihalide e.g., phosgene
  • diaryl carbonates can also be based on carbon dioxide. It is advantageous here that in this way conventional fossil raw materials can be replaced, and the greenhouse gas carbon dioxide can be recycled back into the material cycle, which is generally referred to as closing the carbon cycle. Overall, this would reduce the carbon footprint, which would contribute to global climate change goals. Carbon dioxide is a waste product in many chemical Processes available and can therefore be considered as a sustainable raw material. It is also advantageous that carbon dioxide as a non-combustible gas is easy to handle.
  • carbon dioxide is an inert molecule. So it takes an energy input to convert carbon dioxide into a higher quality chemical. In order to produce a product with a low carbon footprint, the generation of the input energy should in turn be associated with as little carbon dioxide emissions as possible. For example, electric power obtained from renewable energy sources is suitable for this purpose.
  • Comparative Examples 4 and 8 show that dimethyl carbonate, but not diphenyl carbonate, can be obtained with the same palladium electrode. Also, Comparative Example 7 shows that with a heterogeneous palladium electrode, the formation of diphenyl carbonate can not be detected.
  • the same group has further reduced the size of the palladium-based electrocatalyst in subsequent work by using only homogeneous palladium complexes, described in
  • the oxidative carbonylation of phenol is also known as a chemical variant without electricity, as described, for example, in Journal of Molecular Catalysis A: Chemical, 1999, 139, 109-119. Also for this non-electrochemical variant of the oxidative carbonylation of phenol, the choice of catalyst appears to be limited to palladium-based materials. No example of reaction of the oxidative carbonylation of phenol which could be successfully carried out without a palladium-based catalyst has been found in the prior art.
  • WO 2011/024327 A1 describes the preparation of diaryl carbonates via homogeneous catalysis with palladium.
  • This application focuses on making the reaction as efficient as possible and describes exclusively the use of a dissipation or reoxidation electrode, which converts the catalytically inactive Pd ° back into the catalytically active homogeneously dissolved Pd 2+ .
  • the actual catalyst is here, as already described above, the homogeneous Pd 2+ .
  • JP H673582 describes heterogeneous electrocatalysis on a palladium electrode, but only dialkyl carbonates are prepared. As Comparative Example 7 shows, using such an electrode, the formation of a diaryl carbonate could not be detected.
  • WO2014 / 046796 A2 describes inter alia the preparation of (phosgene) COCh. as the starting material for carbonyls with electrochemical conversion of CO 2 to CO and a hydrogen halide or halogen salt to a halogen. This is not an in-situ production of CO from CO 2 in the preparation of diaryl or arylalkyl, since initially phosgene is formed, which is then converted to the carbonates.
  • the present invention has for its object to provide an electrochemical process for the preparation of diaryl carbonates, in which electricity can be used directly as an energy source, and carbon dioxide as a precursor, with fewer reaction steps than in the prior art are required. Furthermore, a heterogeneous electrocatalyst, which is not limited to platinum or palladium-based material, and also should be used
  • Particle sizes> 2 nm may have to improve the long-term stability of such a material. Furthermore, the process for the preparation of diaryl carbonates with a gas diffusion electrode should be carried out, which is the prerequisite of the higher current density for a technical application. The object is achieved with a method for the electrochemical production of
  • Diaryl carbonates which is characterized in that a compound of formula (1)
  • R-OH where the radical R is an aryl radical, preferably tert-butylphenyl, cumylphenyl, naphthyl or phenyl, particularly preferably a phenyl radical, is anodically reacted with CO at a gas diffusion electrode, wherein the gas diffusion electrode at least one comprising planar, electrically conductive carrier and a gas diffusion layer applied to the carrier, wherein the gas diffusion layer contains a mixture of an electrocatalyst and a hydrophobic polymer,
  • electrocatalyst is present in the form of powder selected from the series gold, copper, silver, ruthenium, iridium, copper oxide, ruthenium oxide and iridium oxide, preferably gold, ruthenium, copper, copper oxide and ruthenium oxide
  • the electrocatalyst being in the form of metal particles or metal oxide particles selected from the group consisting of gold, copper, silver, ruthenium, iridium, copper oxide, ruthenium oxide and iridium oxide, preferably gold, ruthenium, copper, copper oxide and ruthenium oxide supported on a carbon support selected from activated carbon, Carbon black, graphite, graphene or carbon nanotubes, in particular carbon black.
  • the particular advantage of the method according to the invention is that it allows the electrochemical preparation of diaryl carbonates with little effort and a small number of reaction steps.
  • the inventively provided gas diffusion electrode is an electrode in which the three states of matter - solid, liquid and gaseous - are in contact and the solid, electron-conducting catalyst catalyzes an electrochemical reaction between the liquid and the gaseous phase.
  • the electrocatalyst is preferably heterogeneous and preferably free of palladium.
  • According to the invention can be based on palladium-based in the gas diffusion electrode
  • the electrocatalyst may be in the form of powder selected from the group consisting of gold, copper, silver, ruthenium, iridium, copper oxide, ruthenium oxide and iridium oxide, preferably gold, ruthenium, copper, copper oxide and ruthenium oxide.
  • electrocatalysts can be used which are present in the form of metal particles or metal oxide particles selected from the series gold, copper, silver, ruthenium, iridium, copper oxide, ruthenium oxide and iridium oxide, preferably gold, ruthenium, copper, copper oxide and ruthenium oxide.
  • the metal particles or metal oxide particles according to the invention are supported on a carbon support selected from activated carbon, carbon black, graphite, graphene or carbon nanotubes, in particular carbon black.
  • the heterogeneous electrocatalyst used in turn allows easy reuse in a wide range of particle sizes, since complex separation processes of catalytically active metal complexes can be omitted.
  • By eliminating the size limitation of the electrocatalyst to the range ⁇ 2 nm results in a greater freedom in the design of the electrodes. Also can be increased by a larger particle size of the electrocatalyst its long-term stability.
  • the process according to the invention uses compounds of the formula (1).
  • Preferred starting compounds of the formula (1) are those selected from the series:
  • the CO is produced cathodically in an upstream reaction electrochemically from CO 2, in particular at a gas diffusion electrode:
  • Carbon cycle is called. Carbon dioxide is available as a waste product in many chemical processes and can thus be used as a sustainable raw material. It is also advantageous that carbon dioxide as a non-combustible gas is easy to handle.
  • the method according to the advantageous embodiment described above is thus characterized by particular sustainability. This is preferably an in-situ generation of the carbon dioxide.
  • the CO thus obtained is preferably reacted directly in the process according to the invention for the electrochemical preparation of diaryl carbonates in the anodic reaction at the gas diffusion electrode.
  • the reaction for the cathodic formation of carbon monoxide can basically be carried out in an analogous manner as described by way of example in Bull, Chem. Soc. Jpn, 1987, 60, 2517-2522. be described described.
  • the anodic electrochemical reaction at a current density in the range of 0.1 to 5000 mA / cm 2 , preferably 0.1 to 500 mA / cm 2 , more preferably 0.1 to 100 mA / cm 2 and most preferably 0.2 to 50 mA / cm 2 .
  • the solvent phenol as the alcohol of formula (1), or a mixture of the alcohol of formula (1) with other solvents, in particular a solvent selected from acetonitrile, propylene carbonate, dimethylformamide, dimethyl sulfoxide, 1, 2nd -Dimethoxyethane, dichloromethane and N-methyl-2-pyrrolidone, more preferably acetonitrile.
  • lithium chloride, lithium bromide, lithium perchlorate, lithium bis (trifluoromethylsulfonyl) imide, sodium phenolate, lithium phenolate, tetrabutylammonium chloride, preferably lithium chloride and lithium perchlorate, or imidazolium, aammonium, phosphonium or pyridinium can be used as electrochemical conductive salts.
  • based ionic liquids preferably 1-ethyl-3-methylimidazolium tetrafluoroborate can be used. Most preferably, the ionic liquids comprise cations as imidazolium, ammonium, phosphonium or pyridinium.
  • the anodically carried out electrochemical reaction at a temperature in the range of 10 to 250 ° C, in particular in the range of 20 to 100 ° C and particularly preferably in the range of room temperature is performed.
  • the reaction can be carried out at atmospheric pressure or elevated pressure, in particular at up to 1 bar overpressure.
  • elevated pressure can be achieved at the electrode higher local concentrations and thus better productivity.
  • the gas diffusion layer of the gas diffusion electrode contains a mixture of electrocatalyst, hydrophobic polymer and other carbon materials, wherein the hydrophobic polymer is a fluorine-substituted polymer, preferably polytetrafluoroethylene (PTFE).
  • PTFE polytetrafluoroethylene
  • the proportion of electrocatalyst in the form of powder is 80 to 97 wt .-%, preferably 90 to 95 wt .-%, based on the total weight of electrocatalyst and hydrophobic polymer, or that
  • the metal or metal oxide powder has an average particle diameter in the range of 1 to 100 ⁇ m, preferably in the range of 2 to 90 ⁇ m, or in that the mean particle diameter of the metal material supported on carbon materials. or metal oxide particles 2 nm to 100 ⁇ , preferably 2 nm to 1 ⁇ .
  • electrocatalyst and hydrophobic polymer are applied and compressed in powder form on the carrier and form the gas diffusion layer.
  • the gas diffusion electrode based on a metal or metal oxide powder as electrocatalyst a total loading of catalytically active component in a range of 5 mg / cm 2 to 300 mg / cm 2 , preferably from 10 mg / cm 2 to 250 mg / cm 2 , or that the gas diffusion electrode based on carbon supported metal or metal oxide particles has a total loading of catalytically active component in a range of
  • 0.5 mg / cm 2 to 20 mg / cm 2 preferably from 1 mg / cm 2 to 5 mg / cm 2 .
  • the electrically conductive carrier as mesh, woven, knitted, knitted, non-woven, expanded metal or foam, preferably as a fabric, particularly preferably as a network, be formed and nickel, gold, silver or a combination of nickel with gold or silver included.
  • the gas diffusion electrode can be produced by applying the catalyst / powder mixture directly to a carrier.
  • the powder mixture is produced in a particularly preferred embodiment by mixing the catalyst powder and the binder and optionally other components.
  • the mixing is preferably done in a mixing device which mixes rapidly rotating mixing elements, e.g. Have flywheel.
  • the mixing elements rotate preferably at a speed of 10 to 30 m / s or at a speed of 4000 to 8000 U / min.
  • the powder mixture is preferably sieved.
  • the sieving is preferably carried out with a sieve device, which with networks o-the like. equipped, whose mesh size 0.04 to 2 mm.
  • the temperature during the mixing process is preferably 35 to 80 ° C.
  • a coolant e.g. liquid nitrogen or other inert heat-absorbing substances.
  • Another way of controlling the temperature may be that the mixing is interrupted to allow the powder mixture to cool or by selecting suitable mixing units or changing the fill in the mixer.
  • the application of the powder mixture to the electrically conductive carrier takes place, for example, by scattering.
  • the spreading of the powder mixture onto the carrier can e.g. done by a sieve.
  • a frame-shaped template is placed on the carrier, wherein the template is preferably selected so that it just covers the carrier.
  • the template can also be chosen smaller than the surface of the carrier. In this case remains after sprinkling the powder mixture and the pressing with the carrier an uncoated edge of the carrier free of electrochemically active coating.
  • the thickness of the template can be selected according to the amount of powder mixture to be applied to the carrier.
  • the template is filled with the powder mixture. Excess powder can be removed by means of a scraper. Then the template is removed.
  • the powder mixture is pressed in a particularly preferred embodiment with the carrier.
  • the pressing can be done in particular by means of rollers.
  • a pair of rollers is used.
  • the pressing can be done by a ram.
  • the forces during pressing are in particular 0.01 to 7 kN / cm.
  • Another aspect relates to the use of the diaryl carbonates obtained from the process according to the invention for the production of polycarbonate, preferably by the melt transesterification process.
  • the transesterification reaction can be described by way of example according to the following equation:
  • GC Gas chromatographic
  • Diphenyl carbonate For the analysis of DMC, the following parameters were used: starting temperature of 40 ° C and held for 1.5 min, heating rate: 50 ° C / min, 200 ° C final temperature would not be maintained.
  • the amount of substance obtained was determined by an external standard. For a known amount of substance of the diphenyl carbonate or dimethyl carbonate of the electrolyte solution was added. The area of the obtained standard electrolytic solution signal was related to the area of the obtained signal of the sample. From this, the amount of substance of the methylphenyl carbonate formed was determined. The yield was determined on the basis of the Farady equation and the amount of substance obtained via the external standard.
  • the gas diffusion electrode was produced by the dry process, wherein 93% by weight gold powder SPF 1775 from Ferro, 7% by weight PTFE from DYNEON TF2053 were mixed in an IKA mill AI 1 basic. Subsequently, the powder mixture was pressed with a roller press at a force of 0.5 kN / cm on a nickel carrier network. For an electrode of size 24 cm 2 , 7.7 g of the powder mixture were needed.
  • the electrolysis was carried out at a carbon monoxide flow rate of 0.5 L / h for 1 h (current density in each case 0.2 mA / cm 2 ). During this time, the electrolyte was pumped in a circle at a rate of 2 mL / min.
  • KB600JD 30.80 g of KB600JD was stirred in 5 mol / L HCl (600 mL) for 1 h at room temperature followed by filtration and washing with FLO (1.5 L). Now KB6OOJD was suspended in 65% HNO3 and refluxed for 2 h at 85 ° C. After that, KB6 OOJD was branded with a filter
  • the gas diffusion electrode was produced by the dry process, wherein 60 wt .-% Pd-KBeooro and 40 wt .-% PTFE from DYNEON TF2053 were mixed in an IKA mill Al l basic. Subsequently, the powder mixture was pressed with a roller press at a force of 0.5 kN / cm on a nickel carrier network. For a 120.8 cm 2 electrode, 4.9 g of the powder mixture was needed.
  • the experiment was carried out in a commercially available Electrocell Model Micro Flow Cell volume (0.001 m 2 ) from Electrocell in a 2-electrode run.
  • the gas diffusion electrode prepared according to Comparative Example 3 was anodically switched, and as the counterelectrode, an iridium-MMO electrode (iridium mixed metal oxide electrode, commercially available from Eelctrocell) was used.
  • the electrolysis was carried out at 2.5 V for 31 min (current density each 0.5 mA / cm 2 ) during which time 30 mL of electrolyte and CO were passed through the cell.
  • 2.66 g of L1CIO4 (0.1 mol / L) were dissolved in MeOH (250 mL).
  • the experiment was carried out in a commercially available Electrocell Model Micro Flow Cell volume (0.001 m 2 ) from Electrocell in a 2-electrode run.
  • the gas diffusion electrode prepared according to Example 1 was anodically switched, and as the counterelectrode an iridium-MMO electrode (iridium mixed metal oxide electrode, commercially available from Electrocell) was used.
  • the electrolysis was carried out at 1.5 V for 31 min (current density each 0.5 mA / cm 2 ) during which time 30 mL of electrolyte and CO were passed through the cell.
  • 2.66 g of L1CIO4 (0.1 mol / L) were dissolved in MeOH (250 mL).
  • the gas diffusion electrode was produced by the dry process, wherein 93 wt .-% palladium powder M8039 from Ferro, 7 wt .-% PTFE from DYNEON TF2053 were mixed in an IKA mill Al l basic. Subsequently, the powder mixture was pressed with a roller press at a force of 0.29 kN / cm on a nickel carrier network. For a 32 cm 2 electrode, 4.3 g of the powder mixture was needed. Comparative Example 7
  • the experiment was carried out in a commercially available Electrocell Model Micro Flow Cell volume (0.001 m 2 ) from Electrocell in a 2-electrode run.
  • the gas diffusion electrode prepared according to Comparative Example 6 was anodically switched, and as the counterelectrode, an iridium-MMO electrode (iridium mixed metal oxide electrode, commercially available from Electrocell) was used.
  • the electrolysis was carried out at a current density of 0.2 mA / cm 2 for one hour.
  • the flow rate of CO was 0.5 L / h and the electrolyte (30 mL) was circulated at a flow rate of 2 mL min 1 .
  • the experiment was performed on the devices, GC7890A with a column (HP-5: Stationary phase: 5% - phenylmetylpolysiloxane, length: 30 mx 320 ⁇ m x 0.25 ⁇ m, carrier gas: helium) and a headspace (HS) sample application system 7697 , executed by Angilent Technologies.
  • 3 mL samples were placed in 20 mL vials in the HS-Sampler and these were heated in the oven for 15 min at 80 ° C, brought to a pressure of 15 psi.
  • 1 mL of the gas phase was applied via a transfer line (200 ° C) to the column with a split of 10: 1.
  • the FID Fluorescence Detector
  • the FID was operated at 300 ° C and a hydrogen flow rate of 40 mL / min
  • the experiment was carried out in a commercially available Electrocell Model Micro Flow Cell volume (0.001 m 2 ) from Electrocell in a 2-electrode run.
  • the gas diffusion electrode prepared according to Comparative Example 3 was anodically switched, and as the counter electrode, an iridium mixed metal oxide (MMO) electrode, commercially available from Electrocell, was used.
  • MMO iridium mixed metal oxide
  • the electrolysis was carried out at a current density of 0.2 mA / cm 2 for one hour.
  • the flow rate of CO was 0.5 L / h and the electrolyte (30 mL) was circulated at a flow rate of 2 mL min 1 .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé électrochimique de production électrochimique de carbonates de diaryle, caractérisé en ce qu'un composé de la formule (1) : R-OH, dans laquelle le reste R désigne un reste aryle, de préférence un reste tert-butylphényle, cumyle phényle, naphtyle ou phényle, de manière davantage préférée un reste phényle, est mis en réaction anodique avec du CO au niveau d'une électrode de diffusion de gaz, l'électrode de diffusion de gaz présentant au moins un support plat électroconducteur et une couche de diffusion de gaz appliquée sur le support ; - la couche de diffusion de gaz contient un mélange composé d'un électrocatalyseur et d'un polymère hydrophobe, - l'électrocatalyseur se présente sous la forme d'une poudre sélectionnée dans la série comprenant l'or, le cuivre, l'argent, le ruthénium, l'iridium, l'oxyde de cuivre, l'oxyde de ruthénium et l'oxyde d'iridium, de préférence l'or, le ruthénium, le cuivre, l'oxyde de cuivre et l'oxyde de ruthénium ou, - l'électrocatalyseur se présente sous la forme de particules métalliques ou de particules d'oxyde métallique sélectionnées dans la série comprenant l'or, le cuivre, l'argent, le ruthénium, l'iridium, l'oxyde le cuivre, l'oxyde de ruthénium et l'oxyde d'iridium, de préférence l'or, le ruthénium, le cuivre, l'oxyde et cuivre ou l'oxyde de ruthénium, portées sur un support en carbone sélectionné parmi le carbone actif, le noir de carbone, le graphite, le graphène ou les nanotubes de carbone, en particulier le carbone actif.
EP18750100.2A 2017-07-03 2018-06-29 Procédé électrochimique de production de carbonates de diaryle Withdrawn EP3649278A1 (fr)

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Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4131521A (en) * 1977-11-07 1978-12-26 Allied Chemical Corporation Electrochemical synthesis of organic carbonates
JPH043582A (ja) 1990-04-19 1992-01-08 Mitsubishi Electric Corp イメージ・スキャナ装置
JPH0673582A (ja) * 1992-08-27 1994-03-15 Daicel Chem Ind Ltd 炭酸ジエステルの製造方法および製造装置
US6695963B2 (en) 2001-07-05 2004-02-24 Asahi Kasei Kabushiki Kaisha Organic electrolysis reactor for performing an electrolytic oxidation reaction and method for producing a chemical compound by using the same
DE10148599A1 (de) 2001-10-02 2003-04-10 Bayer Ag Verfahren zur Herstellung von Gasdiffusionselektroden aus trockenen Pulvermischungen mittels Walzen
DE102007058701A1 (de) * 2007-12-06 2009-06-10 Bayer Materialscience Ag Verfahren zur Herstellung von Diarylcarbonat
JPWO2011024327A1 (ja) 2009-08-31 2013-01-24 三菱化学株式会社 炭酸ジエステルの製造方法
JP2012153909A (ja) * 2009-08-31 2012-08-16 Tokyo Institute Of Technology 炭酸ジエステルの製造方法
CN101787544B (zh) * 2010-01-18 2011-11-23 中南大学 二氧化碳/甲醇电化学合成碳酸二甲酯用复合电极材料及其制备和应用
CN102586799A (zh) * 2011-01-04 2012-07-18 索尼公司 电解制备碳酸酯的方法
US8821709B2 (en) * 2012-07-26 2014-09-02 Liquid Light, Inc. System and method for oxidizing organic compounds while reducing carbon dioxide
CN104641021B (zh) 2012-09-19 2019-02-12 阿凡田知识中心有限公司 利用醇共氧化的二氧化碳电化学还原
WO2015148796A1 (fr) * 2014-03-27 2015-10-01 Joel Rosenthal Système et procédé de conversion électrochimique de dioxyde de carbone en monoxyde de carbone

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