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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 ]
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. C 6 H 5 OH + CH 2 N ...
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:
More so than thiophenol, benzeneselenol is easily oxidized by air. The facility of this reaction reflects the weakness of the Se-H bond, bond dissociation energy of which is estimated to be between 67 and 74 kcal/mol. [1] In contrast, the S-H BDE for thiophenol is near 80 kcal/mol. [3] The product is diphenyl diselenide as shown in this idealized equation:
Dow process (phenol), a method of phenol production through the hydrolysis of chlorobenzene Topics referred to by the same term This disambiguation page lists articles associated with the title Dow process .
In organic chemistry, an azo coupling is an reaction between a diazonium compound (R−N≡N +) and another aromatic compound that produces an azo compound (R−N=N−R’).In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activated carbon (usually from an arene, which is called coupling agent), serves as a nucleophile.