# US 12,180,601 B2 · Electrochemical oxidation of organic molecules

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- Number: US 12,180,601 B2
- Document ID: US12180601B2
- Status: Granted
- Kind: B2
- Application number: 17/277,063
- Filed: 2019-09-24
- Published: 2021-12-02
- Granted: 2024-12-31
- Earliest claimed: 2018-09-24
- Assignees: Massachusetts Institute of Technology
- Applicants: Massachusetts Institute of Technology
- Inventors: Karthish Manthiram; Kyoungsuk Jin; Joseph Maalouf; Kindle Williams; Minju Chung
- Web page: https://patentgrep.com/patent/US12180601B2

## CPC

- C25B 3/23: Oxidation (halogenation C25B3/27)
- H01M 8/18: Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
- C25B 1/04: by electrolysis of water
- C25B 3/05: Heterocyclic compounds
- C25B 3/07: Oxygen containing compounds
- C25B 3/25: Reduction
- C25B 9/17: Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof
- C25B 9/19: with diaphragms
- C25B 11/052: Electrodes comprising one or more electrocatalytic coatings on a substrate
- C25B 11/065: Carbon
- C25B 11/077: the compound being a non-noble metal oxide
- C25B 11/091: consisting of at least one catalytic element and at least one catalytic compound; consisting of two or more catalytic elements or catalytic compounds
- H01M 4/9016: {Oxides, hydroxides or oxygenated metallic salts}
- H01M 4/96: Carbon-based electrodes
- Y02E 60/36: Hydrogen production from non-carbon containing sources, e.g. by water electrolysis
- Y02E 60/50: Fuel cells
- C25B: ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR (anodic or cathodic protection C23F13/00; single-crystal growth C30B)
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A system and method for oxidizing organic molecules as an oxygen-atom source using an electrochemical process is described.

## Claims

### Claim 1

A method of generating an oxidized substrate comprising:
contacting an anode including an oxygen atom transfer epoxidation catalyst composition with a substrate, the oxygen atom transfer epoxidation catalyst composition including single atoms of one element of Re, Ir, Pt, Au, Ru, Rh, or Pd supported on a nanostructured material containing an oxide or metal nanoparticle including Ti, Cr, Mn, Co, Ni, Cu, or Zn;
contacting the anode with a direct oxygen atom source;
applying a voltage to the anode and a cathode to produce an oxidized substrate;
wherein the cathode includes a hydrogen generation catalyst; and generating an epoxide and hydrogen gas.

### Claim 2 (depends on 1)

The method of claim 1, wherein the oxygen atom transfer epoxidation catalyst composition includes a metal oxide, metal hydroxide, metal phosphate, metal borate, metal sulfide, metal phosphide, or metal nitride, or combinations thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein the oxygen atom transfer epoxidation catalyst composition includes a manganese oxide, a titanium oxide, a copper oxide, a zinc oxide, a cobalt oxide, a cobalt phosphide, an iron oxide, a nickel oxide, an iridium oxide, a platinum oxide, or a chromium oxide.

### Claim 4 (depends on 1)

The method of claim 1, wherein the oxidized substrate is produced at a Faradaic yield of at least 20%.

### Claim 5 (depends on 1)

The method of claim 1, wherein the oxygen atom source is water without the need to generate a soluble oxidant from the water.

### Claim 6 (depends on 1)

The method of claim 1, wherein hydrogen gas is produced at the cathode.

### Claim 7 (depends on 6)

The method of claim 6, wherein hydrogen gas is produced at a Faradaic yield of at least 70%.

### Claim 8 (depends on 1)

The method of claim 1, wherein the cathode includes an oxygen reduction catalyst.

### Claim 9 (depends on 1)

The method of claim 1, wherein oxygen is introduced at the cathode and water is produced.

### Claim 10 (depends on 1)

The method of claim 1, wherein a hydrogenation reaction of an organic substrate is conducted at the cathode.

### Claim 11 (depends on 1)

The method of claim 1, wherein the substrate is an olefin that is oxidized to form the epoxide.

### Claim 12 (depends on 1)

The method of claim 1, wherein the substrate contains a C—H bond oxidized to form a product containing a carbon-oxygen bond.

### Claim 13 (depends on 1)

The method of claim 1, wherein the substrate is supplied to the anode at a concentration of 5 mM, 10 mM, 15 mM, 20 mM, 25 mM, 30 mM, 35 mM, 40 mM, 50 mM, 60 mM, 70 mM, 80 mM, 90 mM, 100 mM, 200 mM, 250 mM, 300 mM, 350 mM, 400 mM, 450 mM, 500 mM, 1 M, 2 M, 4 M, 6 M, 8 M, or 10 M.

### Claim 14 (depends on 1)

The method of claim 1, wherein the oxygen atom source is supplied at a concentration of 0.1 M, 0.25 M, 0.5 M, 1 M, 2 M, 4 M, 6 M, 8 M, 10 M, 12 M, 14 M, 16 M, 18 M or 20 M.

### Claim 15 (depends on 1)

The method of claim 1, wherein the voltage is between about 0.2V and 9.0V.

### Claim 16 (depends on 1)

The method of claim 1, wherein the voltage is 0.5V, 0.6V, 0.7V, 0.8V, 0.9V, 1.0V, 1.1V, 1.2V, 1.3V, 1.4V, 1.6V, 1.7V, 1.8V or 1.9V.

### Claim 17 (depends on 1)

The method of claim 1, wherein the cathode includes a noble metal, nickel-molybdenum-zinc alloys, cobalt phosphide, or nickel phosphide.

### Claim 18 (depends on 1)

The method of claim 1, wherein the method is carried out substantially at room temperature.