Derivatization of carbon

Patent metadata

Field	Value
Publication number	US-9637440-B2
Application number	US-201214365945-A
Country	US
Kind code	B2
Filing date	Dec 21, 2012
Priority date	Dec 21, 2011
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

Derivatization of an elemental carbon surface is accomplished by exposing the carbon surface to an aprotic solvent containing a hydrazone molecule of formula (I) or the corresponding salt of formula (II) wherein R 1 is an organic group, and R 2 is an organic group or hydrogen and decomposing the hydrazone in the presence of elemental carbon to create a carbene moiety of formula (III): which attaches to the carbon surface. The attached groups may be redox active so that the derivatized carbon may be used in an electrochemical sensor.

First claim

The invention claimed is:

1. A process for derivatization of a surface of elemental carbon in solid form comprising exposing the carbon surface to an aprotic solvent containing a hydrazone molecule of the general formula

or the corresponding salt of formula

wherein R 1 is an organic group, R 2 is an organic group or hydrogen and M + is a cation and decomposing the hydrazone in the presence of elemental carbon to attach a moiety

to the elemental carbon while the group X is converted to an X − anion.

2. A process according to claim 1 wherein X is a group of the formula —SO 2 —Y.

3. A process according to claim 2 wherein Y is an aryl sulphonyl group.

4. A process according to claim 2 wherein Y is an aromatic group bearing one or more alkyl substituents.

5. A process according to claim 1 wherein at least one of the R 1 and R 2 groups comprises an aromatic group such that the carbon atom of the >C=N—N> hydrazone group can form delocalised bonds with the aromatic ring.

6. A process according to claim 5 wherein at least one of the R 1 and R 2 groups comprises an aromatic group which is one of phenyl, napthyl or anthracenyl or comprises an aromatic ring connected to a vinyl group.

7. A process according to claim 1 wherein at least one of the R 1 and R 2 groups comprises an aromatic ring or system bearing at least one substituent which is a functional group able to undergo electrochemical redox reaction.

8. A process according to claim 7 wherein at least one of the R 1 and R 2 groups comprises an aromatic quinone or is an aromatic group bearing a nitro substituent.

9. A process according to claim 1 wherein at least one of the R 1 and R 2 groups comprises a ferrocenyl group.

10. A process according to claim 1 wherein the elemental carbon is graphite, glassy carbon, carbon fibres, carbon black, carbon paste, boron doped diamond, carbon epoxy, carbon nanotubes or graphene.

11. A process according to claim 1 wherein the elemental carbon is in particulate form and the process further comprises immobilizing the derivatized elemental carbon on an electrode.

12. A process according to claim 1 wherein the elemental carbon is an electrode.

13. A process according to claim 1 wherein decomposing the hydrozone is carried out by heating the aprotic solvent containing the hydrozone, while the solvent is in contact with the elemental carbon.

14. A process according to claim 1 wherein at least one of the R 1 and R 2 groups comprises a redox-active group able to undergo electrochemical redox reaction and the process further comprises utilizing the elemental carbon modified by the attachment of the moiety

thereto as at least part of an electrode, and connecting the electrode to means to apply voltage to the electrode and measure current flow through the electrode, thereby incorporating the modified elemental carbon into measuring apparatus.

15. A process according to claim 1 wherein at least one of the R 1 and R 2 groups comprises a redox active group able to undergo electrochemical redox reaction.

Assignees

• Schlumberger Technology Corp

Inventors

• Crawford Lynne
• Lawrence Nathan
• Jones Timothy

Classifications

• C01B32/194 Primary

  After-treatment · CPC title

• H01M4/583

  Carbonaceous material, e.g. graphite-intercalation compounds or CFx · CPC title

• H01G11/32 Primary

  Carbon-based · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• H01M4/96

  Carbon-based electrodes · CPC title