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The cumene radical then bonds with an oxygen molecule to give cumene peroxide radical, which in turn forms cumene hydroperoxide (C 6 H 5 C(CH 3) 2 O 2 H) by abstracting a benzylic hydrogen from another cumene molecule. This latter cumene converts into cumene radical and feeds back into subsequent chain formations of cumene hydroperoxides.
Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C.
In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process:
Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone.In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:
Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol. [3] It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene: [4] C 6 H 5 (CH 3) 2 CH + O 2 → C 6 H 5 (CH 3) 2 COOH. Dicumyl peroxide is a side product.
A single gas or propane burner used on high or an oven set to 350 °F for 45 minutes raised benzene concentrations in the air above the baseline in every kitchen that was tested and, in some cases ...
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Normally these cumene radicals are converted to cumene hydroperoxide, however they can also undergo radical disproportionation to form AMS. Although this is only a minor side reaction, the cumene process is run at such a large scale that the recovery of AMS is commercially viable and satisfies much of the global demand. AMS can also be produced ...