US 11,851,778 B2
Electrochemical reductive carboxylation of unsaturated organic substrates in ionically conductive mediums
Mikhail Redko, East Lansing, MI (US); Christopher M. Saffron, Okemos, MI (US); and James E. Jackson, Haslett, MI (US)
Assigned to BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY, East Lansing, MI (US)
Appl. No. 16/634,192
Filed by BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY, East Lansing, MI (US)
PCT Filed Jul. 27, 2018, PCT No. PCT/US2018/044014
§ 371(c)(1), (2) Date Jan. 27, 2020,
PCT Pub. No. WO2019/023532, PCT Pub. Date Jan. 31, 2019.
Claims priority of provisional application 62/538,256, filed on Jul. 28, 2017.
Prior Publication US 2020/0181782 A1, Jun. 11, 2020
Int. Cl. C25B 3/05 (2021.01); C25B 3/07 (2021.01); C25B 3/25 (2021.01); C25B 3/26 (2021.01); C07C 51/15 (2006.01)
CPC C25B 3/25 (2021.01) [C07C 51/15 (2013.01)] 19 Claims
OG exemplary drawing
 
1. A method for electrochemical reductive carboxylation of an unsaturated organic substrate, the method comprising:
(a) providing a reactant medium comprising a water-immiscible, ionically conductive, aprotic organic liquid comprising an ionic liquid comprising one or more ionic liquid cations and one or more ionic liquid counter anions, an unsaturated organic substrate reactant, and a carbon dioxide reactant, wherein the reactant medium is free from cation electrolytes other than the one or more ionic liquid cations;
(b) providing a product medium comprising water;
(c) electrochemically reducing the unsaturated organic substrate reactant in the reactant medium with (i) a cathode in the reactant medium and (ii) an anode in the product medium, thereby forming a dicarboxylic organic product comprising a reaction product between (i) at least one of the unsaturated organic substrate reactant and a radical-anion of the unsaturated organic substrate reactant, and (ii) at least one of carboanions formed from the carbon dioxide reactant, CO2− anion-radicals formed from the carbon dioxide reactant, and the carbon dioxide reactant in the reactant medium; and
(d) recovering the dicarboxylic organic product in the product medium after transport of the dicarboxylic organic product formed in the reactant medium to the product medium.