Preparation of cumene hydroperoxide
A three-necked flask with stirrer, reflux condenser, gas-inlet tube with attached sintered plate, safety wash-bottle is charged with 1 mole of cumene, 350 ml of 2% sodium carbonate, 1 g of an emulsifier (sodium palmitate or sodium stearate), and 10 ml of an at least 15% solution of the cumene hydroperoxide (if cumene hydroperoxide is not available the reaction could be initiated with 0.5 g of azo-bis-isobutyronitrile) are heated on the water bath to the reaction temperature (85°C) and a powerful stream of oxygen is passed in until the hydroperoxide content of the solution increases no further (8-10 hours). b.p. 100-101 °C/8 mm; n20/D 1.5210; d=1.03 g/mL at 25 °C.
Determination of the hydroperoxide content
About 2 ml of the reaction solution is treated with 2 g of sodium chloride, and the organic phase is allowed to separate. 0.4 to 1 g of this is weighed accurately into a 200-ml Erlenmeyer flask with a ground-in stopper. 10 ml of acetic anhydride and 1 to 2 g of potassium iodide are added and, after 10 min, 70 ml of water. Then the mixture is shaken vigorously for 30 sec. The iodine liberated is titrated with 0.1 N sodium thiosulphate solution with starch as indicator.
% hydroperoxide = consumption of Na2S203 (ml) x molecular wt. of cumene hydroperoxide (152.19g/mol)/weight of sample (g) x 200
The determination of the hydroperoxide is carried out hourly and the result is plotted on a graph (ordinates: moles of oxygen absorbed; abscissae: time in hours).
Cumene hydroperoxide can be stored for months in closed bottles at 0°C.
Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 177-178, (1973)
cumene hydroperoxide, cumene hydroperoxide, sodium salt, cumyl hydroperoxide, cumylhydroperoxide, isopropyl benzene hydroperoxide
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Cumene peroxide radical, isopropyl benzene hydroperoxide, cumene hydroperoxide, sodium salt, CID6629, alpha, alpha- dimethylbenzyl hydroperoxide, C007164, CHP, 84447-04-1