There are numerous examples of CNT- and related ?-surface functionalization reported in the literature. Surprisingly, no organic rearrangement reaction has been utilized until recently when an Eschenmoser-Claisen rearrangement reaction was applied on graphite oxide to transform a surface allyl alcohol group, with the aid of N,N-dimethylacetamide dimethyl acetal into a carbon-bound N,N-dimethylamide group. Another common example is Beckmann Rearrangement, which is employed to transform oximes to amides. Industrially, the lactam monomer for nylon-6 synthesis is produced by Beckmann Rearrangement (BR) of cyclohexanone oxime using sulfuric acid as the catalyst. In this paper, we reported a first case of BR reaction applied on the MWNT surface. MWNTs were first grafted with carbonyl groups via Friedel-Crafts acylation in polyphosphoric acid, according to our previous work. The surface carbonyl groups were then converted into oxime groups followed by BR reaction in sulfuric acid. The ratios of the rearranged MWNT-bound amide isomers were determined by quantifying the hydrolyzed amides using GC-MS spectroscopy.

Beckmann rearrangement on the surface of multiwalled carbon nanotube

244th National Meeting (2012)

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