DOI: 10.1002/anie.201002160. Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions

Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions

10.1002/anie.201002160

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Dreyer, D. R., Jia, H., & Bielawski, C. W. (2010). Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions. Angewandte Chemie International Edition, 49(38), 6813â6816. Portico.

Authors 3

Daniel R. Dreyer (first)
Hong‐Peng Jia (additional)
Christopher W. Bielawski (additional)

References 44 Referenced 525

10.1055/s-1994-25538
10.1021/jo070887i
10.1021/ja053462r
10.1039/B917103G
10.1016/j.carbon.2007.02.034
10.1002/adfm.200900167
10.1021/jp710931h
10.1021/cm0630800
10.1002/ange.200901678
10.1002/anie.200901678
10.1021/ja01539a017
10.1021/jp9731821
10.1002/cber.18980310237
10.1002/cber.18990320208
10.1016/0008-6223(94)90168-6
10.1016/j.carbon.2005.08.005
10.1016/B978-0-08-009707-7.50013-3
10.1021/ja901105a
10.1016/j.carbon.2009.11.034
10.1021/jp900360k
10.1126/science.1161916
10.1021/ja9061097
10.1103/PhysRevB.73.125415
The GO employed as a catalyst for these studies was prepared from natural flake graphite using the Hummers method;[5]however similar results were obtained when GO was prepared using the Staudenmaier method (see Table 1).[6]
10.1021/jp907613s
The BET surface area of the GO starting material (0.7 m2 g−1) was similar to that measured for the reduced product obtained after the oxidation reaction (3.2 m2 g−1).
10.1021/ja00005a029
At high initial loadings (≥50 wt %) no change in activity was observed for up to 10 cycles. However at low catalyst loadings (≤20 wt %) the recovered catalyst exhibited only approximately 5 % conversion of PhCH2OH into PhCHO after 24 h at 100 °C. Hence as the alcohol oxidation reaction proceeds the catalyst may undergo reduction to a point such that reversion to GO is no longer favored under ambient conditions.
10.1016/j.chemphyslip.2004.03.005
10.1021/ja00855a036
10.1021/nn901689k
In some of the oxidation reactions described the initial heterogeneous dispersion stabilized upon heating/stirring. The respective catalyst was conveniently separated by dissolution of the product mixture in methylene chloride or chloroform followed by filtration of the precipitated solids. There was no loss of the carbon content of the employed catalyst during the reaction based on elemental analysis data; however the total mass of the catalyst decreased as it lost a portion of its oxygen functionality and was reduced.
Similarly benzylamine was converted into benzaldehyde (28 % conversion; conditions: 50 wt % GO 75 °C 24 h). Presumably the reaction proceeded through the respective imine which underwent rapid hydrolysis. In contrast 1‐butanol allyl alcohol 2‐mercaptoethanol and 2‐(methylthio)ethanol showed little or no conversion into their oxidized products under any of the conditions tested.
10.1016/S0040-4020(98)01227-7
10.1021/jo00008a058
10.1021/jo962115k
10.1055/s-2004-817749
10.1039/b507094p

Dates

Type	When
Created	15 years, 1 month ago (July 6, 2010, 9:47 a.m.)
Deposited	1 year, 10 months ago (Oct. 17, 2023, 12:28 a.m.)
Indexed	1 month ago (July 30, 2025, 11:33 a.m.)
Issued	15 years, 2 months ago (July 2, 2010)
Published	15 years, 2 months ago (July 2, 2010)
Published Online	15 years, 2 months ago (July 2, 2010)
Published Print	14 years, 11 months ago (Sept. 10, 2010)

Funders 0

None

BibTeX

@article{Dreyer_2010, title={Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions}, volume={49}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.201002160}, DOI={10.1002/anie.201002160}, number={38}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Dreyer, Daniel R. and Jia, Hong‐Peng and Bielawski, Christopher W.}, year={2010}, month=jul, pages={6813–6816} }

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