Hydro cyano and cyano fullerene derivatives

Inactive Publication Date: 2006-08-31
RGT UNIV OF CALIFORNIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0018] An additional object of the present invention is to relate a derivatized carbon cluster mixing agent utilized in producing a PCM by which the mixing agent facilitates blending of a host polymer and a carbon cluster modified with both hydrogen and cyano moieties

Problems solved by technology

This water can be problematic, as discussed below, in operation of a PEFC.
Lack of suitable membrane availability has been hindering the commercialization of PEFC.
Water management is one of the most difficult issues in operating a PEFC.
A breakdown in water balance between production and loss of water at the cathode side often results in water flood, while the anode interface with the membrane may suffer from water depletion due to water transportation toward the cathode side.
Both the flood and the depletion may increase the cell over-potential, which results in loss of power.
Currently, no commercially available PCM meets this demand.
NAFION, the industrial standard PCM by DuPont, is widely used in PEFC; yet it is sensitive to humidity, a very undesirable characteristic.
Other existing proton conducting membranes, commercially available or under development, are as good or even better than NAFION under fully humidified condition, but very few outperform NAFION under low humidity conditions.
Lack of membranes capable of functioning under low RH, (i.e., maintaining high conductivity, ˜10−1 S cm−1) has been an obstacle to bringing PEFC to market.
The challenge for the industry is how to improve the conductivity of PCMs, where water plays a vital role in proton transportation, under dry condition.
The problem with such an approach is that

Method used

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  • Hydro cyano and cyano fullerene derivatives
  • Hydro cyano and cyano fullerene derivatives
  • Hydro cyano and cyano fullerene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Example

Example 1

Preparation of the Acid Source / Proton-Source Agent (Hydrogen cyano fullerenes)

[0053] Again, C60H(CN) and C60(CN)2 were synthesized according the literature (Keshavarz, M., Knight, Srdanov, G, and Wudl F., JACS 1995, 11371).

[0054] In particular, for the preparation of C60H(CN)3 a degassed solution of NaCN (20 mg, 1.2 eq.) in DMF (20 mL) was added to a degassed solution of C60(CN)2 (260 mg, 0.34 mmol.) in ODCB (30 mL) via canula at room temperature. After being stirred 3 minutes, the resultant deep green solution was treated with perchloric acid (0.25 mL). After 30 minutes, the brown mixture was concentrated and the solid obtained was chromatographed on silica gel (CS2 / Toluene (1:3)), C60H(CN)3 was dissolved in ODCB and crystallized by adding ethyl ether or methanol (51% yield). It is noted that during the synthesis of C60H(CN)3, that the acidity of trifluoroacetic acid (pKa: 0.52) is not strong enough to protonate the C60(CN)3− and a stronger acid like perchloric acid (pK...

Example

Example 2

Preparation of the Mixing Agent (Poly(ethylene oxide) Attached Fullerenes)

[0060] Poly(ethylene oxide) monomethyl ethers (for example, where n˜3, 8, 12, 17, and 45) were functionalized with benzyl bromide in three steps as shown immediately below in Scheme 1:

[0061] As seen in FIG. 5, in the ATRA step, the fullerene was first dissolved in o-dichlorobenzene (ODCB) in a pressure vessel, then 8 equivalents of PEO-benzylbromide (one equivalent yields a mono-PEO final product and the like) and 2,2′-bipyridine were added and the solution was degassed for 10 minutes. After 8 equivalents of Cu(I)Br was added, the vessel was sealed and heated to 110° C. for 24 h until a green precipitate formed. Air was bubbled through the reaction mixture to precipitate un-reacted copper (I) complex. Upon filtration, the solution was concentrated and precipitated into 200 ml of ether. The product, with “n” final PEO chains and “y” bromines, was collected by filtration as a brown oil or solid (fin...

Example

Example 3

Membrane / Film Preparation

[0069] 1. Appropriate amounts of the C60(CN)3H (it is noted that any hydrogen cyano fullerene may be used for the exemplary C60(CN)3H proton-source agent) and, if desired, PEOmC60 (mixing agent) were weighed and added to ˜5 g of Chlorobenzene.

[0070] 2. Required amount of any desired PEO (host polymer) was added to ˜5 g of chlorobenzene in a separate container.

[0071] 3. These mixtures were sonicated (˜10 mins).

[0072] 4. They were then stirred in an 85° C. oil bath for 1˜2 hours.

[0073] 5. After confirming complete dissolution, they were mixed together and stirred for about 1 hour at 85° C. in an oil bath. (PEO tends to gel if the mixing in the earlier stages is not proper.)

[0074] 6. The resultant homogeneous solution was poured into a TEFLON dish and dried in a 120° C. oven for 2˜3 hours to get a composite film.

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Abstract

Novel acidic hydrogen cyano fullerenes and cyano fullerenes are disclosed that may be utilized as components in a proton conducting membrane (PCM). In particular, C60H(CN)n, wherein n>1, and C60(CN)n, wherein n>2, species are provided.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation of copending application Ser. No. 11 / 067,599, filed on Feb. 25, 2005. STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT [0002] Not Applicable INCORPORATION-BY-REFERENCE OF MATERIAL SUBMITTED ON A COMPACT DISC [0003] Not Applicable NOTICE OF MATERIAL SUBJECT TO COPYRIGHT PROTECTION [0004] A portion of the material in this patent document is subject to copyright protection under the copyright laws of the United States and of other countries. The owner of the copyright rights has no objection to the facsimile reproduction by anyone of the patent document or the patent disclosure, as it appears in the United States Patent and Trademark Office publicly available file or records, but otherwise reserves all copyright rights whatsoever. The copyright owner does not hereby waive any of its rights to have this patent document maintained in secrecy, including without limitation its rights pursuant t...

Claims

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Application Information

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IPC IPC(8): B01D71/00
CPCB01D67/0046Y10T428/292B01D69/141B01D71/021B01D2325/26B82Y30/00B82Y40/00C01B31/0206C01B31/0213C08J5/2275H01B1/122H01M8/1023H01M8/1025H01M8/1039H01M8/1044H01M8/1048H01M2300/0082Y02E60/523C08J2323/00Y10S977/779B01D67/0079C01B32/15C01B32/156Y02E60/50B01D69/14111B01D67/00793B01D71/0212
Inventor WUDL, FREDSTUCKY, GALEN D.WANG, HENGBINJOUSSELME, BRUNO
Owner RGT UNIV OF CALIFORNIA
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