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A rhodium catalyst for single-step styrene production from benzene and ethylene

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Science  24 Apr 2015:
Vol. 348, Issue 6233, pp. 421-424
DOI: 10.1126/science.aaa2260

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A more direct way to synthesize styrene

Foam cups, foam pellets, plastic cutlery: All are made of polystyrene, which in turn is made of styrene. The massive manufacturing scale of this commodity chemical places a premium on the efficiency of its synthesis. The current industrial route requires three steps to make styrene from benzene and ethylene. Vaughan et al. present a rhodium catalyst that achieves the coupling in a single step by using a recyclable copper salt as an oxidant. Although the catalyst is slow for industrial application, it demonstrates the viability of a more direct process.

Science, this issue p. 421

Abstract

Rising global demand for fossil resources has prompted a renewed interest in catalyst technologies that increase the efficiency of conversion of hydrocarbons from petroleum and natural gas to higher-value materials. Styrene is currently produced from benzene and ethylene through the intermediacy of ethylbenzene, which must be dehydrogenated in a separate step. The direct oxidative conversion of benzene and ethylene to styrene could provide a more efficient route, but achieving high selectivity and yield for this reaction has been challenging. Here, we report that the Rh catalyst (FlDAB)Rh(TFA)(η2–C2H4) [FlDAB is N,N′-bis(pentafluorophenyl)-2,3-dimethyl-1,4-diaza-1,3-butadiene; TFA is trifluoroacetate] converts benzene, ethylene, and Cu(II) acetate to styrene, Cu(I) acetate, and acetic acid with 100% selectivity and yields ≥95%. Turnover numbers >800 have been demonstrated, with catalyst stability up to 96 hours.

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