Issue 7, 2010

Solvent-free dehydrogenation of γ-terpinene in a ball mill: investigation of reaction parameters

Abstract

The present article reports on the solvent-free dehydrogenation of γ-terpinene (1) in a planetary ball mill affording p-cymene (2) as the predominant reaction product. The influence of various reaction parameters and technical variables on the transformation of 1 has been assessed. Thus, it is shown that KMnO4 can be substituted by other, less-toxic and environmentally-benign oxidation agents (Oxone®, NaIO4, I2). In most cases the reaction yielded 2 with high selectivities, whereby conversion can be fine-tuned by variation of the oxidant-to-substrate ratio, the rotation frequency νrot, the number of milling balls nball or the type of grinding auxiliary employed. Contrary to particle refinement processes, the size of the milling balls d (constant mass) has no influence on the conversion and chemical yield.

Graphical abstract: Solvent-free dehydrogenation of γ-terpinene in a ball mill: investigation of reaction parameters

Supplementary files

Article information

Article type
Paper
Submitted
12 Feb 2010
Accepted
14 Apr 2010
First published
04 Jun 2010

Green Chem., 2010,12, 1288-1294

Solvent-free dehydrogenation of γ-terpinene in a ball mill: investigation of reaction parameters

T. Szuppa, A. Stolle, B. Ondruschka and W. Hopfe, Green Chem., 2010, 12, 1288 DOI: 10.1039/C002819C

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