System and process for anthraquinone functionalization
AssigneesQuino Energy, Inc., President and Fellows of Harvard College
InventorsEugene Beh, Meisam Bahari, Min Wu, Michael Aziz, Roy Gordon
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Abstract
The invention relates to the synthetic functionalization of an anthraquinone molecule that is substituted with at least one hydroxyl or amino group. In some aspects of the invention a mixture containing said anthraquinone starting material, an aldehyde, a base, an optional solvent, and an optional catalyst is reacted with hydrogen and then with an oxidant. In other aspects of the invention the synthetic functionalization of the anthraquinone molecule takes place electrochemically rather than chemically, through the use of a divided electrolytic cell.
Claims25
A system comprising:
- a divided electrolytic cell, further comprising:
- a first chamber comprising a first electrode, and a first fluid stream, the first fluid stream comprising:
- an anthraquinone derivative of Formula I, Formula II, Formula III, or
- wherein each X independently is OH or NH2;
- the first fluid stream further comprising an aldehyde, a base, and an optional solvent;
- a second chamber comprising a second electrode, and a second fluid stream;
- the first chamber and first electrode separated by an ion-conducting membrane from the second chamber and second electrode;
- wherein the first fluid stream further comprises an (alpha-hydroxy)alkylated anthraquinone derivative and/or an alkylated anthraquinone derivative.
A redox flow battery comprising:
- a divided electrolytic cell, further comprising:
- a first chamber comprising a first electrode and first fluid stream, the first fluid stream comprising an anthraquinone derivative of Formula I, Formula II, Formula III, or Formula IV:
- wherein each X independently is OH or NH2;
- the first fluid stream further comprising an aldehyde, a base, and an optional solvent;
- a second chamber comprising a second electrode and a second fluid stream;
- the first chamber and first electrode separated by an ion-conducting membrane from the second chamber and second electrode;
- wherein the first fluid stream further comprises an (alpha-hydroxy)alkylated anthraquinone derivative and/or an alkylated anthraquinone derivative;
- and
- wherein the divided electrolytic cell the (alpha-hydroxy)alkylated anthraquinone derivative and/or the alkylated anthraquinone derivative as a first flow battery reactant, and the second fluid stream as a second flow battery reactant.
A method for the (alpha-hydroxy)alkylation or alkylation at the 2-position of an anthraquinone derivative, comprising:
- providing a divided electrolytic cell, further comprising:
- a first chamber with a first electrode, configured to accept and have an electrochemical reaction with a first fluid stream comprising said anthraquinone derivative of Formula I, Formula II, Formula III, or Formula IV:
- wherein each X independently is OH or NH2;
- the first fluid stream further comprising an aldehyde, a base, and an optional solvent;
- a second chamber with a second electrode, configured to accept and have an electrochemical reaction with a second fluid stream;
- the first chamber and first electrode separated by an ion-conducting membrane from the second chamber and second electrode;
- flowing the first fluid stream through the first chamber and contacting the first electrode;
- flowing the second fluid stream through the second chamber and contacting the second electrode;
- and
- applying an electrical potential between the first and second electrode, so as to cause an electrochemical reduction reaction in the first fluid stream and an electrochemical oxidation reaction in the second fluid stream;
- wherein the first fluid stream further comprises an (alpha-hydroxy)alkylated anthraquinone derivative and/or an alkylated anthraquinone derivative.
Dependencies are inferred from the claim text.