EP4227442A1 - Synthèse électrochimique appariée d'éthers diméthyliques d'oxyméthylène - Google Patents

Synthèse électrochimique appariée d'éthers diméthyliques d'oxyméthylène Download PDF

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Publication number
EP4227442A1
EP4227442A1 EP22156518.7A EP22156518A EP4227442A1 EP 4227442 A1 EP4227442 A1 EP 4227442A1 EP 22156518 A EP22156518 A EP 22156518A EP 4227442 A1 EP4227442 A1 EP 4227442A1
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EP
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Prior art keywords
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dimethyl ether
water
compartment
organic solvent
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EP22156518.7A
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German (de)
English (en)
Inventor
Francesc SASTRE CALABUIG
Robin Jeremy White
Earl Lawrence Vincent Goetheer
Roman LATSUZBAIA
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Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO
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Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO
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Priority to EP22156518.7A priority Critical patent/EP4227442A1/fr
Priority to PCT/NL2023/050069 priority patent/WO2023153933A1/fr
Publication of EP4227442A1 publication Critical patent/EP4227442A1/fr
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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
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/07—Oxygen containing compounds
    • 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
    • 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
    • C25B15/00—Operating or servicing cells
    • C25B15/08—Supplying or removing reactants or electrolytes; Regeneration of electrolytes
    • C25B15/081—Supplying products to non-electrochemical reactors that are combined with the electrochemical cell, e.g. Sabatier reactor
    • 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
    • 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
    • C25B3/25—Reduction
    • 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
    • C25B3/25—Reduction
    • C25B3/26—Reduction of carbon dioxide

Definitions

  • the invention relates to the field of electrochemistry.
  • the invention relates to electrochemical synthesis. More in particular, the invention relates to an electrochemical route to oxymethylene dimethyl ethers.
  • Oxymethylene dimethyl ethers are represented by the general formula CH 3 (OCH 2 ) n OCH 3 , wherein "n” is an integer.
  • the integer “n” can be 1 or more, such as 2 or more.
  • the "n” in the general formula can be an integer of 2-10.
  • Methanol can be produced by reacting hydrogen with carbon dioxide.
  • Formaldehyde is typically produced via oxidative dehydrogenation of methanol.
  • US-A-2014/0 367 274 describes an electrochemical method for formaldehyde synthesis via methanol oxidation at a cathode. Two separate product streams are produced since the products at the anode and cathode are incompatible. The method is not designed to form OME.
  • OME non-electrochemically such as the aqueous acid-catalysed condensation reaction of methanol with formaldehyde (or trioxane).
  • Kröcher et al. (Appl. Catal. B-Environ. 2017, 217, 407-420 ) describes the acid-catalysed synthesis of OME, reaction mechanism and catalyst types. Such acid-catalysed synthesis is considered costly and less efficient due to process step numbers, water management and complex reactants.
  • Mitsos et al. (Ind. Eng. Chem. Res. 2019, 58(12), 4881-4889 ) describes the production of CH 3 O(CH 2 O) 1 CH 3 from hydrogen and carbon dioxide via excess methanol and aqueous formaldehyde, in a fixed-bed reactor.
  • Another objective of the invention is to address this need in the art. Another objective of the invention is to provide a convenient electrochemical route to OME that requires few steps. It is another objective of the invention to provide a cost-efficient route to OME.
  • the invention is directed to a method of producing oxymethylene dimethyl ether (OME), comprising preparing OME via paired electrosynthesis.
  • OME oxymethylene dimethyl ether
  • the invention takes a new and innovative approach to improve the energy and ecological efficiency.
  • the approach includes paired electrochemical reduction and oxidation reactions.
  • paired electrosynthesis is meant to indicate that both anodic and cathodic reactions form at least one intermediate compound (reactant) to the formation of OME, such as formaldehyde, and/or form (a) desired product(s), such as OME and/or formaldehyde.
  • the intermediate compound(s) (reactant(s)) and/or product(s) formed by both the anodic and cathodic reactions can be the same or different.
  • the anodic and cathodic reactions may form the same intermediate compound (reactant) and/or product.
  • the paired electrosynthesis comprises the formation of formaldehyde by anodic and cathodic reactions.
  • the paired electrosynthesis can comprise the formation of one product from two or more starting materials, or the formation of two or more products, including OME, from one or more starting materials.
  • anodic and cathodic reactions are combined into one overall reaction and are preferably allowed to occur simultaneously.
  • the paired electrosynthesis can be performed in a single compartment or in multiple separate compartments, such as in two separate compartments.
  • the paired electrosynthesis is performed in multiple separate compartments, such as in two separate compartments.
  • the invention is directed to a method of producing oxymethylene dimethyl ether reactants (OME reactants), comprising electrochemically preparing said reactants, comprising formaldehyde and optionally methanol, by paired electrosynthesis.
  • OME reactants oxymethylene dimethyl ether reactants
  • the reactants are suitable for forming OME.
  • the method may be a one-step or two-step method of producing OME.
  • the method may comprise a step of forming formaldehyde in an anodic reaction mixture and/or in a cathodic reaction mixture, preferably at least in the cathodic reaction mixture; and a step of forming OME in the anodic reaction mixture and/or in the cathodic reaction mixture.
  • the method may comprise a step of forming formaldehyde, preferably with OME, in a cathodic reaction mixture, and preferably formaldehyde, optionally with OME, in an anodic reaction mixture.
  • the method may comprise a step of forming formaldehyde, in an electrochemical cell, both at an anode and at a cathode; and a step of collecting the formaldehyde and reacting it with an alcohol, preferably comprising methanol, to form OME.
  • an alcohol preferably comprising methanol
  • OME organic compound
  • the method can be carried out in one or more electrochemical reactors.
  • any type of reactor may be usable.
  • the reactor may be operated in batch condition, in semi-continuous condition or in continuous condition. Batch processing has a lower risk of failure and is characterised by long reaction times, yet lower production rates are typically a result. Continuous processing may be more efficient and lucrative, as product(s) can be obtained in significantly larger amounts and require lower operating costs.
  • the method is carried out under continuous operating conditions.
  • the electrochemical reactor can comprise a single compartment wherein the reduction and oxidation reactions may happen.
  • the reactor can comprise two or more compartments, including a cathodic compartment with a cathode at which, for example, the carbon monoxide and/or carbon dioxide can be reduced. Whereas the paired electrosynthesis may be performed in an electrochemical reactor, the preparing of the reaction product comprising OME may be performed within the same electrochemical reactor or outside the electrochemical reactor.
  • Carbon monoxide and/or carbon dioxide may be electrochemically reduced.
  • the carbon monoxide and/or carbon dioxide do not have to be of a specific origin or purity, although it can be beneficial from a process perspective.
  • Either reactant may be part of a stream that comprises, for example, nitrogen and/or hydrogen.
  • the carbon monoxide and/or carbon dioxide can originate from a (pre)combustion process in, for example, the steel industry; a natural gas stream; a biogas stream; synthesis gas; water, and/or air.
  • the reduction can be carried out at atmospheric pressure, for example, approximately 1 bar. It is preferred to carry out the reduction at an elevated pressure.
  • the reduction may be carried out at an absolute pressure of 10 bar or more, such as 30 bar or more; 50 bar or more; 70 bar or more, and, for example, 200 bar or less, such as 170 bar or less; 150 bar or less, or 130 bar or less.
  • the reduction is carried out at an absolute pressure of 30 bar or more and/or 150 bar or less, such as 30-150 bar or 50-130 bar.
  • the reduction can be carried out at ambient temperature (e.g., room temperature).
  • the reduction can be carried out at 0 °C or higher, such as 10 °C or higher, 20 °C or higher, or 30 °C or higher.
  • the reduction is carried out at 0-70 °C, such as 10-60 °C. More preferably, the reduction is carried out at 20-50 °C.
  • the reduction can be carried out in a single compartment or a cathodic compartment of, for example, an electrochemical reactor, such as described in this disclosure.
  • the reduction can result in, for example, carbon monoxide, methanol and/or formaldehyde.
  • the single compartment or cathodic compartment comprises a cathode.
  • the cathode may comprise one or more selected from the group consisting of metals, doped carbon materials and carbon-based materials.
  • Suitable metals include platinum, palladium, rhodium, osmium, gold, silver, titanium, copper, iridium, ruthenium, lead, nickel, cobalt, zinc, cadmium, tin, iron, gallium, thallium, tungsten, indium, antimony, and bismuth, oxides and/or alloys thereof, mixed metal oxides, dimensionally stable electrode (DSA ® ), stainless steel, brass, and the like.
  • Suitable carbon-based materials include graphite, carbon felt, glassy carbon, and the like.
  • the cathode comprises boron-doped diamond (BDD).
  • the cathode can comprise a plate electrode; a foam electrode; a mesh electrode (3-D electrode); a gas diffusion electrode, or a combination thereof.
  • the electrochemical reduction can be carried out in a catholyte.
  • the catholyte may refer to a single solvent or to a mixture of solvents.
  • the catholyte can comprise a (first) non-aqueous solvent.
  • the solvent may be polar or apolar (dielectric constant of 10 or less).
  • the solvent can be an organic solvent.
  • the organic solvent is preferably a polar organic solvent or a protic organic solvent, such as a polar protic organic solvent.
  • the catholyte can comprise one or more alcohols.
  • the one or more alcohols can be selected from C 1 -C 8 alcohols.
  • the alcohol is selected from the group consisting of methanol; ethanol; n-propanol; iso -propanol; n-butanol; iso -butanol; tert-butanol; n-pentanol, and tert -pentyl alcohol.
  • the non-aqueous solvent comprises methanol.
  • the catholyte can comprise 20 % water or less, based on the total weight of the catholyte.
  • the catholyte can comprise 15 wt.% or less of water, such as 12 wt.% or less; 10 wt.% or less, or 8 wt.% or less.
  • the catholyte comprises 6 wt.% or less of water, such as 5 wt.% or less, 4 wt.% or less, or 3 wt.% or less. More preferably, the catholyte comprises 2 wt.% or less of water.
  • the catholyte is essentially free of water ( i.e ., 1 wt.% or less of water, such as 0.5 wt.% or less).
  • the electrochemical reactor comprising a cathodic compartment can further comprise an anodic compartment with an anode at which an alcohol can be oxidised.
  • the alcohol can be selected from C 1 -C 8 alcohols.
  • the alcohol is selected from the group consisting of methanol; ethanol; n-propanol; iso -propanol; n-butanol; iso -butanol; tert-butanol; n-pentanol, and tert -pentyl alcohol.
  • the alcohol is methanol.
  • the methanol can be formed by a reaction of hydrogen and carbon dioxide. However, the methanol does not have to be of a specific origin or purity.
  • the oxidation can be carried out at atmospheric pressure, for example, approximately 1 bar, or at an elevated pressure.
  • the oxidation may be carried out at an absolute pressure of 10 bar or more, such as 30 bar or more; 50 bar or more; 70 bar or more, and, for example, 200 bar or less, such as 170 bar or less; 150 bar or less, or 130 bar or less.
  • the oxidation is carried out at an absolute pressure of 30 bar or more and/or 150 bar or less, such as 30-150 bar or 50-130 bar.
  • the oxidation can be carried out at ambient temperature (room temperature).
  • the oxidation can be carried out at a temperature of 0 °C or higher, such as 10 °C or higher, 20 °C or higher, or 30 °C or higher.
  • the oxidation is carried out at a temperature of 0-70 °C, such as 10-60 °C. More preferably, the oxidation is carried out at 20-50 °C.
  • the oxidation can be carried out in an anodic compartment of, for example, an electrochemical reactor.
  • the oxidation can result in, for example, formaldehyde, carbon dioxide, and/or formic acid.
  • the anodic compartment comprises an anode.
  • the anode may comprise one or more metals.
  • the anode comprises platinum.
  • the oxidation can be carried out in an anolyte.
  • the anolyte may refer to a single solvent or to a mixture of solvents.
  • the anolyte can comprise a (second) non-aqueous solvent.
  • the solvent may be polar or apolar.
  • the non-aqueous solvent can comprise an organic solvent.
  • the organic solvent is preferably a polar organic solvent or a protic organic solvent, such as a polar protic organic solvent.
  • the non-aqueous solvent can comprise one or more alcohols.
  • the one or more alcohols can be selected from C 1 -C 8 alcohols.
  • the alcohol is selected from the group consisting of methanol; ethanol; n-propanol; iso -propanol; n-butanol; iso -butanol; tert-butanol; n-pentanol, and tert -pentyl alcohol.
  • the non-aqueous solvent comprises methanol.
  • An advantage of using methanol is that it can act as both a solvent as well as a reactant.
  • the anolyte can comprise 20 % water or less, based on the total weight of the anolyte.
  • the anolyte can comprise 15 wt.% or less of water, such as 12 wt.% or less; 10 wt.% or less, or 8 wt.% or less.
  • the catholyte comprises 6 wt.% or less of water, such as 5 wt.% or less; 4 wt.% or less, or 3 wt.% or less. More preferably, the anolyte comprises 2 wt.% or less of water.
  • the anolyte is essentially free of water (i.e ., 1 wt.% or less of water, such as 0.5 wt.% or less).
  • both the reduction and oxidation can be carried out in an electrolyte.
  • the electrolyte may refer to a single solvent or to a mixture of solvents.
  • the electrolyte can comprise a non-aqueous solvent.
  • the solvent may be polar or apolar (dielectric constant of 10 or less).
  • the solvent can be an organic solvent.
  • the organic solvent is preferably a polar organic solvent or a protic organic solvent, such as a polar protic organic solvent.
  • the electrolyte can comprise one or more alcohols.
  • the one or more alcohols can be selected from C 1 -C 8 alcohols.
  • the alcohol is selected from the group consisting of methanol; ethanol; n-propanol; iso-propanol; n-butanol; iso-butanol; tert-butanol; n-pentanol, and tert -pentyl alcohol.
  • the non-aqueous solvent comprises methanol.
  • the electrolyte can comprise 20 % water or less, based on the total weight of the electrolyte.
  • the electrolyte can comprise 15 wt.% or less of water, such as 12 wt.% or less; 10 wt.% or less, or 8 wt.% or less.
  • the electrolyte comprises 6 wt.% or less of water, such as 5 wt.% or less, 4 wt.% or less, or 3 wt.% or less. More preferably, the electrolyte comprises 2 wt.% or less of water. Even more preferably, the electrolyte is essentially free of water ( i.e ., 1 wt.% or less of water, such as 0.5 wt.% or less).
  • the reduction and oxidation in the single compartment can be carried out at atmospheric pressure, for example, approximately 1 bar, or at an elevated pressure.
  • both reactions may be carried out at an absolute pressure of 10 bar or more, such as 30 bar or more; 50 bar or more; 70 bar or more, and, for example, 200 bar or less, such as 170 bar or less; 150 bar or less, or 130 bar or less.
  • the reactions are carried out at an absolute pressure of 30 bar or more and/or 150 bar or less, such as 30-150 bar or 50-130 bar.
  • Both reactions can be carried out at ambient temperature (room temperature). In particular, both reactions can be carried out at a temperature of 0 °C or higher, such as 10 °C or higher, 20 °C or higher, or 30 °C or higher. Preferably, both reactions are carried out at a temperature of 0-70 °C, such as 10-60 °C. More preferably, both reactions are carried out at 20-50 °C.
  • the paired electrosynthesis may comprise electrochemically reducing carbon monoxide and/or carbon dioxide and electrochemically oxidising an alcohol as described in this disclosure, wherein the electrochemical reduction forms formaldehyde.
  • the electrochemical oxidation of methanol can form formaldehyde.
  • the paired electrosynthesis comprises electrochemically reducing carbon monoxide and/or carbon dioxide and electrochemically oxidising methanol, wherein both the electrochemical reduction of carbon monoxide and/or carbon dioxide, and the electrochemical oxidation of methanol form formaldehyde.
  • carbon monoxide and/or carbon dioxide is electrochemically reduced in a compartment comprising a cathode, wherein said cathode comprises one or more of the groups consisting of metals, carbon-doped materials, and carbon-based materials; and/or alcohol is electrochemically oxidised in a compartment comprising an anode, said anode comprising one or more metals.
  • the method is preferably performed in an electrochemical reactor.
  • the cathode comprises boron-doped diamond (BDD).
  • BDD boron-doped diamond
  • the anode preferably comprises platinum.
  • the method of the invention is performed in an electrochemical reactor as described in this disclosure, and the method comprises feeding a non-aqueous mixture comprising carbon monoxide and/or carbon dioxide, and methanol to a compartment comprising a cathode (a cathodic compartment), wherein the cathode comprises boron-doped diamond (BDD).
  • a non-aqueous mixture comprising an alcohol, such as methanol is fed to a compartment comprising an anode (an anodic compartment), wherein the anode comprises platinum.
  • This preferred method also comprises combining the mixtures of said compartments into one reaction mixture, which is suitable for forming OME.
  • the reaction mixture comprises formaldehyde, such as from the electrochemical reduction of carbon monoxide and/or carbon dioxide, and preferably formaldehyde from the electrochemical oxidation of methanol.
  • the reaction mixture may comprise OME, as explained herein.
  • the component(s) of the reaction mixture which may include methanol, may be reacted to form OME.
  • Methanol and/or formaldehyde may be added to the reaction mixture to react with the component(s) of the reaction mixture.
  • the formation of OME may be performed in the electrochemical reactor where the paired electrosynthesis is performed, or outside the electrochemical reactor.
  • the heat produced with the paired electrosynthesis is preferably used in the OME formation reaction.
  • OME obtainable by the method of the invention.
  • the method further comprises isolating OME, for example, from the reaction mixture.
  • OME comprises one or more compounds represented by general formula CH 3 O(CH 2 O) n CH 3 , wherein "n" is 1 or more.
  • OME comprises 75 % or more of CH 3 O(CH 2 O) 1 CH 3 , based on the total weight of OME.
  • this comprises 80 wt.% or more of CH 3 O(CH 2 O) 1 CH 3 , such as 85 wt.% or more, or 90 wt.% or more and, for example, less than 100 wt.%, such as 99 wt.% or less, or 95 wt.% or less.
  • OME comprises 80-99 wt.% of CH 3 O(CH 2 O) 1 CH 3 , such as 85-95 wt.%.
  • OME obtainable by the method of the invention may comprise a small and/or number of impurities, such as methanol, water, formic acid, formaldehyde, and the like.
  • OME can comprise 10 % or less of impurities by total weight of the oxymethylene dimethyl ether.
  • OME can comprise 7 wt.% or less of impurities, such as 5 wt.% or less, or 3 wt.% or less.
  • OME comprises 2 wt.% or less of impurities, such as 1 wt.% or less, or 0.5 wt.% or less.
  • OME can be used for the synthesis of longer chain or polymeric oxymethylene dimethyl ether.
  • the method of the invention may further comprise the formed OME with formaldehyde, thereby forming longer chain or polymeric OME.
  • the formaldehyde can be as obtained by the method of the invention.
  • the longer chain or polymeric oxymethylene dimethyl ether may comprise one or more compounds represented by general formula CH 3 O(CH 2 O) n CH 3 , wherein "n" is an integer of 3 or more. Preferably, "n” is an integer of 3-10. More preferably, "n” is 3, 4 or 5.
  • OME wherein "n” in the general formula is an integer of 3, 4 or 5, can be used as a synthetic fuel or fuel additive.
  • longer chain or polymeric oxymethylene dimethyl ether obtainable by the method of producing oxymethylene dimethyl ether of the invention that further comprises reacting OME with formaldehyde to form a longer chain or polymeric oxymethylene dimethyl ether.
  • the longer chain oxymethylene dimethyl ether may comprise 75 % or more of compounds of CH 3 O(CH 2 O) n CH 3 , wherein "n" is 2 or more, based on the total weight of the oxymethylene dimethyl ether.
  • the oxymethylene dimethyl ether comprises 80 wt.% or more of compounds of CH 3 O(CH 2 O) n CH 3 , wherein "n" is 2 or more, such as 85 wt.% or more, or 90 wt.% or more and, for example, less than 100 wt.%, such as 99 wt.% or less, or 95 wt.% or less. More preferably, the oxymethylene dimethyl ether comprises 80-99 wt.% of compounds of CH 3 O(CH 2 O) n CH 3 , wherein "n” is 2 or more, such as 85-95 wt.%.
  • the longer chain oxymethylene dimethyl ether may comprise a small and/or number of impurities, such as oxymethylene dimethyl ether (e.g., wherein "n” in the general formula is 1), methanol, water, formic acid, formaldehyde, and the like.
  • the longer chain oxymethylene dimethyl ether can comprise 10 % or less of impurities by total weight of the longer chain oxymethylene dimethyl ether.
  • the longer chain oxymethylene dimethyl ether can comprise 7 wt.% or less of impurities, such as 5 wt.% or less, or 3 wt.% or less.
  • the longer chain oxymethylene dimethyl ether comprises 2 wt.% or less of impurities, such as 1 wt.% or less, or 0.5 wt.% or less.
  • OME produced with the method of the invention can be represented by general formula CH 3 O(CH 2 O) n CH 3 , wherein "n” is an integer of 2 or more.
  • “n” can be 5 or more or 10 or more and, for example, 20 or less or 15 or less, such as 2-20.
  • "n” is an integer selected from 2-10. More preferably, "n” is 3, 4 or 5.
  • OME of CH 3 O(CH 2 O) n CH 3 , where "n" is 3, 4 or 5 are considered particularly suitable as synthetic fuels and fuel additives. Hence, there is also provided the use of such OME as synthetic fuel or fuel additive.
  • the invention is directed to a method of producing a polyoxymethylene dimethyl ether.
  • the method comprises preparing oxymethylene dimethyl ether according to the method of the invention.
  • the method further comprises reacting the oxymethylene dimethyl ether with formaldehyde to form the polyoxymethylene dimethyl ether.
  • the formaldehyde may originate from any source, but particularly from the methods of the invention, such as the reduction and/or oxidation reactions.
  • the polyoxymethylene dimethyl ether is a longer chain or polymeric oxymethylene dimethyl ether, such as described in this disclosure.
  • the polyoxymethylene dimethyl ether comprises one or more compounds represented by general formula CH 3 O(CH 2 O) n CH 3 , wherein "n" is an integer of 3 or more.
  • the method comprises preparing oxymethylene dimethyl ether according to the method of the invention.
  • the method further comprises reacting the oxymethylene dimethyl ether with one or more aldehydes to form a functionalised oxymethylene dimethyl ether.
  • the one or more aldehydes may be selected from the group consisting of acyclic aldehydes and arylaldehydes.
  • the one or more aldehydes are selected from C 1 -C 8 acyclic aldehydes, such as acetaldehyde, propanal and butanal; benzaldehyde; and derivatives thereof.
  • paired electrolysis to electrosynthesis of OME.
  • the use of paired electrolysis is new and innovative, and results in an energy efficient and convenient preparing of OME, which can be used for further formation of longer chain or polymeric OME, or functionalised OME.
  • the paired electrolysis comprises the electrochemical oxidation of methanol paired with the electrochemical reduction of carbon monoxide and/or carbon dioxide.

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EP22156518.7A 2022-02-14 2022-02-14 Synthèse électrochimique appariée d'éthers diméthyliques d'oxyméthylène Pending EP4227442A1 (fr)

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EP22156518.7A EP4227442A1 (fr) 2022-02-14 2022-02-14 Synthèse électrochimique appariée d'éthers diméthyliques d'oxyméthylène
PCT/NL2023/050069 WO2023153933A1 (fr) 2022-02-14 2023-02-14 Synthèse électrochimique appariée d'éthers diméthyliques d'oxyméthylène

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Citations (4)

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WO2009145624A1 (fr) * 2008-05-30 2009-12-03 Inoviakem B.V. Utilisation de dioxyde de carbone actif dans l’oxydation de composés ayant un groupe hydroxy
US20140367274A1 (en) 2012-07-26 2014-12-18 Liquid Light, Inc. Electrochemical Reduction of CO2 with Co-Oxidation of an Alcohol
US20180134642A1 (en) * 2016-11-17 2018-05-17 OME Technologies GmbH Process for preparing polyoxymethylene dimethyl ethers from formaldehyde and methanol in aqueous solutions
WO2021150117A1 (fr) 2020-01-24 2021-07-29 Nederlandse Organisatie Voor Toegepast- Natuurwetenschappelijk Onderzoek Tno Production électrochimique de formaldéhyde

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