Abstract
Selective photochemical oxidation of styrene was performed in an active acetonitrile medium, using H2O2 with or without ultraviolet (UV) light radiation. Pyrithione metal complexes (M–Pth: M = Cu(II), Ni(II), Ru(II); Pth = 2-mercaptopyridine-N-oxide) were used as catalysts. Catalytic testing measurements were done by varying the time, chemical reaction temperature and H2O2 concentration with or without UV energy. Epoxide styrene oxide (SO), benzaldehyde and acetophenone were the major synthesized products. A high batch rate, conversion and selectivity towards SO was shown in the presence of UV. A minor constant formation of CO2 was observed in the stream. Coordinated Ru-based compounds demonstrated the highest process productivity of SO at 60 °C. The effect of the functional alkyl substituent on the ligand Pth, attached to the specific ruthenium(II) centre, decreased the activity of the substance. Ni-Pth selectively yielded benzaldehyde. The stability of the catalysts was examined by applying nuclear magnetic resonance (NMR) spectroscopy and thermogravimetric analysis coupled with mass spectrometry. Tested metal complexes with pyrithione (M–Pth) exhibited excellent reuse recyclability up to 3 cycles.
Highlights
The oxidative transformation of hydrocarbons is an economical way for the production of corresponding alkenes[1,2]
The results showed that the oxo species of M nV(N) acts as an active oxidation species for photochemical oxidation catalysts
This study focused on various metal complexes, namely RuII, CuII and N iII, with the ligand 2-mercaptopyridine-N-oxide or pyrithione (Pth) (Fig. 1)
Summary
The oxidative transformation of hydrocarbons is an economical way for the production of corresponding alkenes[1,2]. The amount of styrene oxide formed during the reaction was high, the conversion of styrene was low compared to the other non-photocatalytic reaction systems reported in the literature. Ru complexes showed high selectivity towards styrene oxide, which could be due to the lower affinity of N iII and CuII-oxo complexes towards olefins.
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