High solubility thioether quinones

Patent metadata

Field	Value
Publication number	US-11021441-B2
Application number	US-202016822189-A
Country	US
Kind code	B2
Filing date	Mar 18, 2020
Priority date	Feb 28, 2017
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.

First claim

The invention claimed is:

1. A method of installing one or more thioether sulfonate moieties onto one or more unsubstituted carbon atoms of a hydroquinone or 1,4-benzoquinone ring, the method comprising the steps of:
(a) contacting a first 1,4-benzoquinone having a first unsubstituted carbon atom on the benzoquinone ring with a first mercaptoalkylsulfonate, whereby a first hydroquinone adduct having the corresponding first thioether sulfonate moiety installed onto the first unsubstituted carbon atom is formed; and
(b) oxidizing the first hydroquinone adduct by applying an electric current to it, whereby a second 1,4 benzoquinone having the first thioether sulfonate moiety installed onto the first unsubstituted carbon atom is formed.

2. The method of claim 1 , further comprising the step of oxidizing a hydroquinone having one or more unsubstituted carbon atoms on the hydroquinone ring to form the first 1,4-benzoquinone.

3. The method of claim 1 , wherein the second 1,4 benzoquinone has a second unsubstituted carbon atoms on the benzoquinone ring, and wherein the method further comprises the steps of:
(c) contacting the second 1,4-benzoquinone with a second mercaptoalkylsulfonate, whereby a second hydroquinone adduct having the corresponding second thioether sulfonate moiety installed onto the second unsubstituted carbon atom is formed; and
(d) oxidizing the second hydroquinone adduct by applying an electric current to it, whereby a third 1,4 benzoquinone having the second thioether sulfonate moiety installed onto the second unsubstituted carbon atom is formed.

4. The method of claim 3 , wherein the third 1,4 benzoquinone has a third unsubstituted carbon atoms on the benzoquinone ring, and wherein the method further comprises the steps of:
(e) contacting the third 1,4-benzoquinone with a third mercaptoalkylsulfonate, whereby a third hydroquinone adduct having the corresponding third thioether sulfonate moiety installed onto the third unsubstituted carbon atom is formed; and
(0 oxidizing the third hydroquinone adduct by applying an electric current to it, whereby a fourth 1,4 benzoquinone having the third thioether sulfonate moiety installed onto the third unsubstituted carbon atom is formed.

5. The method of claim 4 , wherein the fourth 1,4 benzoquinone has a fourth unsubstituted carbon atoms on the benzoquinone ring, and wherein the method further comprises the step of:
(g) contacting the fourth 1,4-benzoquinone with a fourth mercaptoalkylsulfonate, whereby a fourth hydroquinone adduct having the corresponding fourth thioether sulfonate moiety installed onto the fourth unsubstituted carbon atom is formed.

6. The method of claim 1 , wherein the first 1,4-benzoquinone is a 1,4-benzoquinone having four unsubstituted carbon atoms on the benzoquinone ring.

7. The method of claim 1 , wherein the first 1,4-benzoquinone is a 1,4-benzoquinone having three unsubstituted carbon atoms and a carbon atom substituted with an electron withdrawing group on the benzoquinone ring.

8. The method of claim 1 , wherein the electric current is applied to the first, second, or third hydroquinone adduct or combinations thereof through an electrolysis anode.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Stahl Shannon S
• Gerken James B

Classifications

• C07C323/66 Primary

  containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton · CPC title

• C07D285/14

  condensed with carbocyclic rings or ring systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• H01M8/188

  by recharging of redox couples containing fluids; Redox flow type batteries · CPC title

• C07D209/48

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title