Synthesis of cumene hydroperoxide

Preparation of cumene hydroperoxide

Preparation of cumene hydroperoxide

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)

IUPAC Name

2-hydroperoxypropan-2-ylbenzene

InChI

InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3

InChI Key

YQHLDYVWEZKEOX-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C1=CC=CC=C1)OO

MeSH Synonyms

cumene hydroperoxide, cumene hydroperoxide, sodium salt, cumyl hydroperoxide, cumylhydroperoxide, isopropyl benzene hydroperoxide

Depositor-Supplied Synonyms

CUMENE HYDROPEROXIDE, Cumyl hydroperoxide, 80-15-9, alpha,alpha-Dimethylbenzyl hydroperoxide, Cumenyl hydroperoxide, 7-Cumyl hydroperoxide, Cumolhydroperoxid, Cumolhydroperoxide, Hydroperoxide, 1-methyl-1-phenylethyl, Cument hydroperoxide, Isopropylbenzene hydroperoxide, Hydroperoxyde de cumene, Hydroperoxyde de cumyle, RCRA waste number U096, Cumeenhydroperoxyde, Kumenylhydroperoxid, 7-Hydroperoxykumen, Hydroperoxide de cumene, Idroperossido di cumene, Idroperossido di cumolo, 1-Methyl-1-phenylethyl hydroperoxide, Cumolhydroperoxid [German], RCRA waste no. U096, Cumeenhydroperoxyde [Dutch], Kumenylhydroperoxid [Czech], 7-Hydroperoxykumen [Czech], CCRIS 3801, HSDB 254, CHEBI:78673, Hydroperoxyde de cumene [French], Hydroperoxyde de cumyle [French], Idroperossido di cumene [Italian], Idroperossido di cumolo [Italian], YQHLDYVWEZKEOX-UHFFFAOYSA-N, EINECS 201-254-7, alpha,alpha-Dimethylbenzylhydroperoxide, BRN 1908117, Hydroperoxide, 1-methyl-1-phenylethyl-, Hydroperoxide, alpha,alpha-dimethylbenzyl, Hydroperoxide, alpha,alpha-dimethylbenzyl-, ST50824346, Hydroperoxide, .alpha.,.alpha.-dimethylbenzyl, cumylhydroperoxide, Hyperiz, Percumyl H, cumyl-hydroperoxide, Trigonox K 80, Trigonox K-95, Trigonox R 239A, alpha-Cumyl hydroperoxide, AC1L1MYA, alpha-Cumene hydroperoxide, DSSTox_CID_4869, UNII-PG7JD54X4I, .alpha.-Cumyl hydroperoxide, CHP-5, DSSTox_RID_77559, PG7JD54X4I, .alpha.-Cumene hydroperoxide, DSSTox_GSID_24869, SCHEMBL15251, KSC242S5N, r 239a, 2-hydroperoxy-2-phenylpropane, 247502_ALDRICH, 513296_ALDRICH, 2-hydroperoxypropan-2-ylbenzene, CHEMBL1518369, SCHEMBL11210695, CHP-158, MolPort-003-928-520, ZINC8585911, Tox21_300283, AR-1L3029, (1-hydroperoxy-1-methyl-ethyl)benzene, AKOS015841738, CCG-207896, LS-1792, RL05089, RTR-033452, UN 2116, CAS-80-15-9, Cumene hydroperoxide (Luperox(R) CU90), NCGC00091748-01, NCGC00091748-02, NCGC00091748-03, NCGC00254045-01, AN-42174, OR001343, OR342390, TR-033452, .alpha.,.alpha.-Dimethylbenzyl hydroperoxide, C2223, 4-06-00-03221 (Beilstein Handbook Reference), I14-19803, 79568-78-8

Removed Synonyms

Cumene peroxide radical, isopropyl benzene hydroperoxide, cumene hydroperoxide, sodium salt, CID6629, alpha, alpha- dimethylbenzyl hydroperoxide, C007164, CHP, 84447-04-1

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