Heterocycle catalyzed electrochemical process

• US 9,970,117 B2
• Filed: 09/17/2014
• Issued: 05/15/2018
• Est. Priority Date: 03/19/2010
• Status: Active Grant

• Current Assignee: Avantium Knowledge Centre B.V. (Avantium NV), Princeton University
• Original Assignee: Avantium Knowledge Centre B.V. (Avantium NV), Princeton University
• Inventors: Cole, Emily Barton, Bocarsly, Andrew B.
• Primary Examiner(s): Wong, Edna
• Application Number:
  US14/488,848
• Publication Number:
  US 20150047987A1
• Time in Patent Office: 1,336 Days
• Field of Search: 205446, 205450, 205440
• CPC Class Codes: C25B 1/55 Photoelectrolysis
• CPC Class Codes: C25B 3/25 Reduction
• CPC Class Codes: C25B 3/295 hydrodimerisation
• CPC Class Codes: Y02E 60/36 Hydrogen production from non-carbon containing sources, e.g. by water electrolysis

Abstract

A method for heterocycle catalyzed electrochemical reduction of a carbonyl compound is disclosed. The method generally includes steps (A) to (C). Step (A) may introduce the carbonyl compound into a solution of an electrolyte and a heterocycle catalyst in a divided electrochemical cell. The divided electrochemical cell may include an anode in a first cell compartment and a cathode in a second cell compartment. The cathode generally reduces the carbonyl compound to at least one aldehyde compound. Step (B) may vary which of the aldehyde compounds is produced by adjusting one or more of (i) a cathode material, (ii) the electrolyte, (iii) the heterocycle catalyst, (iv) a pH level and (v) an electrical potential. Step (C) may separate the aldehyde compounds from the solution.

Claims

1. A method for heterocycle catalyzed hydrodimerization of carbonyl-containing molecules, comprising the steps of:

(A) introducing said carbonyl-containing molecules into a solution of an electrolyte and a heterocycle catalyst in a divided electrochemical cell, wherein (i) said divided electrochemical cell comprises an anode in a first cell compartment and a cathode in a second cell compartment, (ii) said cathode hydrodimerizing said carbonyl-containing molecules into at least one organic product;

(B) varying which of said organic products is produced by adjusting one or more of (i) a cathode material, (ii) said electrolyte, (iii) said heterocycle catalyst, (iv) a pH level and (v) an electrical potential; and

(C) separating said organic products from said solution, wherein said heterocycle catalyst is one or more of amino-thiazole, aromatic heterocyclic amines with an aromatic 5-member heterocyclic ring, aromatic heterocyclic amines with 6-member heterocyclic ring, azoles, benzimidazole, bipyridines, furan, imidazoles, imidazole related species with at least one five-member ring, indoles, pyridines, pyridine related species with at least one six-member ring, pyrrole, thiophene and thiazoles.

2. The method according to claim 1, wherein said electrolyte is at least one of Na₂ SO₄, KCl, NaNO₃, NaCl, NaF, NaClO₄, KClO₄, K₂SiO₃, CaCl₂, a H cation, a Li cation, a Na cation, a K cation, a Rb cation, a Cs cation, a Ca cation, an ammonium cation, an alkylammonium cation, a F anion, a Cl anion, a Br anion, an I anion, an At anion, an alkyl amine, berates, carbonates, nitrites, nitrates, phosphates, polyphosphates, perchlorates, silicates, sulfates, and a tetraalkyl ammonium salt.

3. The method according to claim 1, wherein said organic products comprise one or more of butanone, butanol, octanone and octanol.

4. The method according to claim 1, wherein said carbonyl-containing molecules comprise one or more of acetaldehyde, butyric acid and lactic acid.