Aerobic oxidation of cumene catalysed by 4-alkyloxycarbonyl-N-hydroxyphthalimide

Abstract

Abstract4-Hexyloxycarbonyl-, 4-dodecyloxycarbonyl- and 4-hexadecyloxycarbonyl-N-hydroxyphthalimides were synthesised using trimellitic anhydride chloride as the starting material. The obtained lipophilic derivatives of N-hydroxyphthalimide were applied as catalysts of the cumene oxidation reaction with oxygen performed in polar acetonitrile, in non-polar tert-butylbenzene and in the absence of a solvent. The courses of reactions catalysed by N-hydroxyphthalimide and its derivatives were compared.

Solvent-free aerobic oxidative cleavage of alkenes catalyzed by N-hydroxyphthalimide

“…C16-NHPI was synthesized based on previously the described procedure [15]. 4-Methoxy-a-methylstyrene (4MeOAMS) was obtained by the reported twostep method [16] consisting of the alkaline cleavage of bisphenol A to phenol and 4-isopropenylphenol, followed by the alkylation of 4-isopropenylphenol using dimethyl sulfate.…”

“…Oxidation reactions carried out in the presence of NHPI often require polar solvent due to low solubility of NHPI in hydrocarbons. As solvent elimination is an important factor in green chemistry, to overcome this problem, some lipophilic derivatives of NHPI has been synthesized and applied in solvent-free oxidations of alkylaromatics [13][14][15]. In this paper, in contrast to previous studies, the catalytic aerobic cleavage of alkenes in solvent-free conditions has been performed.…”

<i>N</i>-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide

“…The influence of polar products formed in the reaction, on the increase of NHPI solubility has been observed previously by us in the reactions of oxidation of several hydrocarbons with oxygen. [14] …”

“…[14] N,N'-Dihydroxypyromelitimide, NDHPI, was obtained from 1,2,4,5-benzenetetracarboxylic anhydride and hydroxylamine hydrochloride according to the reported method. [15] …”

N-Hydroxyphthalimide Immobilized on Poly(HEA-co-DVB) as Catalyst for Aerobic Oxidation Processes

“…[52]. p-Methoxytoluene (2.0 mL, 15.9 mmol) or α-methylstyrene (2.0 mL, 16.3 mmol), HEA/ DVB-NHPI (0.10 g), AIBN (0.03 mmol) and/or Co(OAc) 2 · H 2 O (0.02 mmol) were placed in a flask connected to a gas burette filled with oxygen under atmospheric pressure.…”