The Hydroxylation of Unsaturated Substances. IV. The Catalytic Hydroxylation of Unsaturated Hydrocarbons¹

Hydrogen Peroxide Reactions with Olefins

“…The reaction of hydrogen peroxide in tert-butyl alcohol with liquid olefins can be carried out in glass flasks equipped with cooling and condensing facilities. The reaction of gaseous olefins is more diffi cult: either the gas must be entrained through the reagent (22), or its solubility must be increased by pressure.…”

“…A review of the chemical literature (1,2,5,16,20,30,40) and laboratory experiments confirmed that the Milas reagent ( 14,19,21,22,23,24,26,28 ), osmium tetroxide in f erf-butyl alcohol, is one of the more effective catalysts for liquid-phase oxidation.…”

“…uydrogen peroxide is becoming less expensive and has been used for the " liquid-phase oxidation of olefins (7,21,22,23,24,26,34,38,39); but its use in oxidizing gaseous olefins has not received much attention. We have investigated its use in oxidizing gaseous olefins, especially propylene, noting in particular the glycol and by-product yields obtained.…”

Metal-Catalysed Epoxidations of Olefins with Hydroperoxides

“…The synthesis of glycols by reaction of olefins with hydrogen peroxide, in the presence of compounds of certain metals as catalysts, was first reported by Epoxidations with hydrogen peroxide 7 Milas et al [18][19][20] in the 1930s. and these reagents are generally referred to as Milas reagents.…”

“…tungstic and vanadic acids and their salts, are capable of forming effective catalysts for this reaction [18][19][20][21][22][23][24][25][26][27][28]. such as OS04' Mo0 3 , W0 3 , V 2 0 S and Cr0 3 , and derivatives such as molybdic.…”