IP Library Granted Patent US 9,035,089
Granted Patent B2
US 9,035,089 · App. 13/230,054 · Granted May 19, 2015

Modified carbon material and process of making and using the same

Inventor: Ping Liu (Irvine, CA)
Assignee: GM Global Technology Operations LLC
C07C309/10C07B2200/11
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Quick Facts
Patent No.
US 9,035,089
App. No.
13/230,054
Granted
May 19, 2015
Kind
B2
Abstract

A method of making modified carbon materials for use in fabricating fuel cell components. The modified carbon may comprise pendant fluorocarbon groups bonded covalently bonded thereto. In one embodiment, a mixture is formed and comprises carbon material suitable for use in a fuel cell component, an organic solvent, a compound having the general formula I—R wherein R is a fluorocarbon, and a reductant.

Claims (37)

1. A method comprising:

providing a carbon material suitable for use in a fuel cell component;

forming a mixture by mixing the carbon material with an organic solvent;

adding a compound with the formula I—R, wherein R comprises a fluorocarbon;

adding a reductant to the mixture; and

agitating the mixture for a time period sufficient to generate radicals of .R which form carbon-carbon covalent bonds with the carbon material to form a modified carbon material.

2. A method as set forth in claim 1 wherein the fluorocarbon renders the modified carbon material more hydrophobic.

3. A method as set forth in claim 1 wherein the fluorocarbon renders the modified carbon material more hydrophilic.

4. A method as set forth in claim 1 wherein adding a compound with the formula I—R comprises adding an amount of the compound I—R such that the ratio of R to carbon material is about 0.25 mmol/g to about 5 mmol/g.

5. A method as set forth in claim 1 wherein agitating the mixture comprises agitating the mixture at a temperature between about 0° C. and about 100° C. for a time period between about 1 day and about 10 days.

6. A method as set forth in claim 1 wherein adding a compound with the formula I—R comprises adding a compound wherein R comprises a perfluorocarbon having the general formula C n F 2n , where n≧1.

7. A method as set forth in claim 1 wherein adding a compound with the formula I—R comprises adding a compound wherein R comprises a perfluorosulfonic acid precursor group comprising a sulfonyl fluoride end group.

8. A method as set forth in claim 7 wherein adding a compound with the formula I—R comprises adding a compound wherein R comprises a perfluorosulfonic acid precursor group having the general formula C n F 2n SO 2 F, wherein 1≦n≦10.

9. A method as set forth in claim 7 wherein adding a compound with the formula I—R comprises adding a compound wherein R comprises a perfluorosulfonic acid precursor molecule having the general formula C n F 2n OC n F 2n SO 2 F, wherein 1≦n≦10.

10. A method as set forth in claim 7 further comprising:

subjecting the modified carbon material to a hydrolysis reaction to convert the sulfonyl fluoride end group to an end group comprising a sulfonate functional group having the general formula SO 3 M, wherein M comprises Li, Na, K, or tetraalkylammonium; and

subjecting the modified carbon material to an acidification reaction to convert the end group comprising a sulfonate functional group to a sulfonic acid end group.

11. A method as set forth in claim 10 wherein subjecting the perfluorosulfonic acid precursor group to a hydrolysis reaction comprises mixing the modified carbon material with water, an organic solvent, and a metal hydroxide.

12. A method as set forth in claim 10 wherein the subjecting the perfluorosulfonic acid precursor group to an acidification reaction comprises mixing the carbon material with an acid.

13. A method as set forth in claim 1 wherein providing the carbon material suitable for use in a fuel cell component comprises providing at least one of graphite, carbon black, vitreous carbon, activated charcoal, carbon aerogel, carbon fiber, or activated carbon.

14. A method as set forth in claim 1 wherein forming a mixture by mixing the carbon material with an organic solvent comprises mixing the carbon material with at least one of dimethylsulfur oxide, dichloromethane, dimethylformide, acetonitrile, propylene carbonate, ethylene carbonate, or diethyl carbonate.

15. A method as set forth in claim 1 wherein adding a reductant to the mixture comprises adding at least one of sodium hydrosulfite (Na 2 S 2 O 4 ) or copper.

16. A method comprising:

forming a mixture by mixing a carbon material suitable for use in a fuel cell component, an organic solvent, a reductant, and a compound having the general formula IC n F 2n in an amount such that the ratio of C n F 2n to carbon material is from about 0.25 mmol/g to about 5 mmol/g;

agitating the mixture to form a modified carbon material.

17. A method as set forth in claim 16 further comprising:

separating the modified carbon material from the mixture; and

fabricating the modified carbon material into a fuel cell component.

18. A method comprising:

forming a first mixture by mixing a carbon material suitable for use in a fuel cell component, an organic solvent, a reductant, and a compound having the general formula I—R in an amount such that the ratio of R to carbon material is from about 0.25 mmol/g to about 5 mmol/g, and wherein R comprises a perfluorosulfonic acid precursor molecule comprising a sulfonyl fluoride end group (SO 2 F);

agitating the mixture to form a modified carbon material;

converting the sulfonyl fluoride end group to an end group comprising a sulfonate functional group;

converting the end group comprising a sulfonate functional group to a sulfonic acid end group.

19. A method as set forth in claim 18 wherein forming a mixture comprises mixing a compound with the formula I—R, wherein R comprises a perfluorosulfonic acid precursor molecule having the general formula C n F 2n SO 2 F or C n F 2n OC n F 2n SO 2 F with 1≦n≦10.

20. A method as set forth in claim 18 further comprising:

separating the modified carbon material from the mixture, and

fabricating the modified carbon material into a fuel cell component.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Nov 7, 2014
From: WILMINGTON TRUST COMPANY
To: GM GLOBAL TECHNOLOGY OPERATIONS LLC
Reel/Frame 034186/0776 →
SECURITY AGREEMENT Recorded Jun 28, 2012
From: GM GLOBAL TECHNOLOGY OPERATIONS LLC
To: WILMINGTON TRUST COMPANY
Reel/Frame 028458/0184 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 12, 2011
From: LIU, PING
To: GM GLOBAL TECHNOLOGY OPERATIONS LLC
Reel/Frame 026887/0040 →
Continuity (1)
Related Publication 20130066105A1 · Mar 14, 2013