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DOE OSTI · 1817908

An Iron-Based Dehydration Catalyst for Selective Formation of Styrene

Nachtigall, Olaf·VanderWeide, Andrew I.·Brennessel, William W.·Jones, William D.
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Abstract

In this work, we report the synthesis and crystal structure of [Fe(OTf) 2 (FOX)] (A). This robust iron(II) complex was successfully applied as a homogeneous catalyst for the dehydration of 1-phenylethanol to styrene. Even at low catalyst loadings and moderate reaction temperatures, A showed a high catalytic efficiency. It was found to selectively activate the benzylic alcohol group of 1-phenylethanol. This is challenging since the vinyl system of styrene is highly reactive. In contrast to most of the other dehydration processes, the use of a Brønsted acid was not necessary. Furthermore, mechanistic insights into this E 1 -type transformation and its competing S N 1-type side reactions are reported. [Fe( c HexOH)(OTf)(FOX)][OTf] (B), an alcohol adduct of A, [Fe(H 2 O) 2 (FOX)][OTf] 2 (C), the completely hydrated derivative of A, and [μ-O{Fe(OTf)(FOX)} 2 ][OTf] 2 (D), a dinuclear oxidation product of A, were also characterized and are discussed.

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02 PETROLEUM37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRYcatalysiscatalysis, dehydration, iron, industrial chemistry, kinetics, isotopes, reactive intermediatesdehydrationindustrial chemistryironisotopeskineticsreactive intermediates

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Nachtigall, Olaf, VanderWeide, Andrew I., Brennessel, William W., Jones, William D.. 2021-08-24. An Iron-Based Dehydration Catalyst for Selective Formation of Styrene. https://doi.org/10.1021/acscatal.1c03037

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