Complex formation of 1-methylcyclohexylhydroper oxide with esters of boric acid

Puring, M. N.; Potekhin, V. M.; Itskovich, V. A.; Lebedev, V. B.

doi:10.1007/bf00614260

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“…According to several investigators [22,[37][38][39][40], it has been suggested that during the borateassisted oxidation of alkanes, a coordinatively bonded complex is formed between the boron atom and unpaired electrons on the oxygen atom of the intermediate alkyl hydroperoxide, as illustrated in Scheme 3. The unstable complex may subsequently decompose homolytically into free radicals such as R 1 O • and HO • , which further propagate the oxidation, or it can undergo heterolytic decomposition resulting in the formation of molecular products, mainly alcohols.…”

Section: Mechanism Of Liquid-phase Oxidation Of N-pentanementioning

confidence: 99%

Borate-assisted liquid-phase selective oxidation of n-pentane

Aworinde¹,

Wang²,

Lapkin³

2018

Applied Catalysis A: General

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Oxidation of n-pentane with molecular oxygen to sec-pentanols was performed in the presence of a free radical initiator (di-tert-butyl peroxide) and a boron compound (sec-butyl metaborate), with in situ adsorption of water on molecular sieve 3A. Kinetics of the reaction was studied in a laboratory-scale batch reactor over a broad range of conditions (130-150°C, 20-30 bar, 5-10 vol% O 2) in order to establish the optimum parameters for maximising the selectivity and yield of sec-pentanols. Results show that the initiator markedly improves the rate of oxidation, and hence yield, compared to thermal oxidation without an initiator, while the boron species enhances the selectivity to sec-pentanols. Under the conditions investigated, maximum secpentanol selectivity is 56% with an alcohol-to-ketone ratio of 3.6:1 for the borate-assisted oxidation compared to 33% and 1.1:1, respectively, for the oxidation without borate. This work demonstrates the feasibility of oxyfunctionalization of n-pentane with industrially relevant selectivity and yield.

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