The increasing global demand for fossil resources has sparked a renewed interest in new catalytic technologies for the conversion of hydrocarbons from petroleum and natural gas to higher value chemicals. For example, styrene is produced from benzene and ethylene on a scale of approximately 18.5 million tons annually. The current route for styrene production involves acid-catalyzed formation of ethylbenzene, trans-alkylation to optimize the yield of mono-functionalized product, and dehydrogenation of ethylbenzene. The direct oxidative conversion of benzene and ethylene to produce styrene could provide a more efficient route, but catalysts that have been developed previously for this transformation suffer from low selectivity and/or low yields. The new rhodium catalyst (FlDAB)Rh(TFA)(η2–C2H4­) [FlDAB = N,N’-bis(pentafluorophenyl)-2,3-dimethyl-1,4-diaza-1,3-butadiene; TFA = trifluoroacetate] converts benzene, ethylene and air-recyclable Cu(II) oxidants to styrene with yields ≥ 95% (based on Cu(II) as the limiting reagent) and with quantitative selectivity. Turnover numbers &gt; 800 have been demonstrated with catalyst stability up to 96 hours. A combined experimental and computational study has been employed to elucidate mechanistic features of this unique catalytic process.

Development of a rhodium(I) catalyst for single-step styrene production

251st National Meeting (2016)

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