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The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), [1] and independently by Heinrich Hock in 1944. [2] [3] This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone.
The Raschig–Hooker process's ability to make phenol makes it comparable to other methods, such as the Dow and Bayer process, which also converts benzene into phenol. In fact, the ability to recycle the hydrogen chloride made the Raschig–Hooker process preferable to the Dow and Bayer process, which requires its sodium chloride product to be ...
Benzene can be easily converted to chlorobenzene by nucleophilic aromatic substitution via a benzyne intermediate. [1] It is treated with aqueous sodium hydroxide at 350 °C and 300 bar or molten sodium hydroxide at 350 °C to convert it to sodium phenoxide, which yields phenol upon acidification. [2]
The first stage of Fenton's reaction (oxidation of Fe 3+ with hydrogen peroxide) is used in Haber–Weiss reaction; Fenton's reagent can be used in organic synthesis reactions: e.g. hydroxylation of arenes via a free radical substitution; Conversion of benzene into phenol by using Fenton's reagent; Oxidation of barbituric acid into alloxan.
To convert from / to /, divide by 1000. a (L ... Benzene: 18.24 0.1193 Bromobenzene: 28.94 0.1539 ... Phenol [2] 22.93 0.1177 Phosphine: 4.692 0.05156
Phenol is reduced to benzene when it is distilled with zinc dust or when its vapour is passed over granules of zinc at 400 °C: [22] C 6 H 5 OH + Zn → C 6 H 6 + ZnO When phenol is treated with diazomethane in the presence of boron trifluoride ( BF 3 ), anisole is obtained as the main product and nitrogen gas as a byproduct.
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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: