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Cyclohexane Functionalization Catalyzed by Octahedral Molecular Sieve (OMS-1) Materials

Journal of Catalysis
Publication Date
DOI: 10.1006/jcat.1998.2049


Abstract Both the abundance of alkanes and their extremely low activity have greatly interested several researchers. In this paper, different metal substituted 3×3 octahedral molecular sieves (OMS-1) materials were used to catalyze the functionalization of cyclohexane by using tert-butyl hydroperoxide as oxidant and tert-butyl alcohol as solvent at different temperatures (60, 80, and 100°C). [Fe]-OMS-1 at 80°C exhibits the best activity and selectivity. The solvent t-butyl alcohol (the reduced state of t-butyl hydroperoxide) was first introduced to the reaction system which makes the system simple to study. The effects of catalyst amount and ratio of tert-butyl alcohol to cyclohexane were examined. Variable speed stirring (200–800 rpm) experiments suggest that under conditions reported here that diffusion is not a problem. Studies of the liquid phase after separation from the solid OMS-1 catalysts have shown that metal does not leach into the solution and that heterogeneous catalysis occurs. At 80°C, the conversion of cyclohexane or the total yield of products can reach 13.1% in 40 h. The yields of cyclohexanone, cyclohexanol, and cyclohexyl hydroperoxide were 6.57, 2.83, and 1.38%, respectively, and t-butyl cyclohexyl perether was 2.36%. The reaction conditions are mild, and the catalysts retain their crystallinity after reaction. Moreover, the catalyst can be easily separated from the reaction mixture and used catalysts retain similar catalytic activity over a 40-h time period.

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