Electrochemical oxidation of organic molecules

Patent metadata

Field	Value
Publication number	US-12180601-B2
Application number	US-201917277063-A
Country	US
Kind code	B2
Filing date	Sep 24, 2019
Priority date	Sep 24, 2018
Publication date	Dec 31, 2024
Grant date	Dec 31, 2024

Abstract

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

First claim

What is claimed is:

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.

2. 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.

3. 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.

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

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

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

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

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

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

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

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

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

13. 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.

14. 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.

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

16. 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.

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

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

Assignees

• Massachusetts Inst Technology

Inventors

• Manthiram Karthish
• Jin Kyoungsuk
• Maalouf Joseph
• Williams Kindle
• Chung Minju

Classifications

• C25B11/091

  consisting of at least one catalytic element and at least one catalytic compound; consisting of two or more catalytic elements or catalytic compounds · CPC title

• C25B9/17

  Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof · CPC title

• C25B11/077

  the compound being a non-noble metal oxide · CPC title

• C25B11/065

  Carbon · CPC title

• C25B3/05

  Heterocyclic compounds · CPC title