Phenol, from benzene hydroxylation, also

Starting from Benzene. In the direct oxidation of benzene [71-43-2] to phenol, formation of hydroquinone and catechol is observed (64). Ways to favor the formation of dihydroxybenzenes have been explored, hence CuCl in aqueous sulfuric acid medium catalyzes the hydroxylation of benzene to phenol (24%) and hydroquinone (8%) (65). The same effect can also be observed with Cu(II)—Cu(0) as a catalytic system (66). Efforts are now directed toward the use of Pd° on a support and Cu in aqueous acid and in the presence of a reducing agent such as CO, H2, or ethylene (67). Aromatic... 

The loss of the hydroxyl group from either the starting cyclohexanol (to give cyclohexane), or from phenol (to give benzene) can also take place. Dehydration of cyclohexanol to cyclohexene is also possible as summarised in Scheme 3. These reactions were studied over various metal catalysts, by using different mixtures containing one labelled component. Typical results obtained on Cu, Ni and Pt catalysts are summarised in Table 5. The specific radioactivities decreased in the sequence cH-ol > cH-one > phenol on Cu and Ni catalysts, while a different order cH-ol > phenol > cH-one was observed on Pt, as well as on Pd. Thus, the sequential reaction 1 2 leads to phenol in the former two catalysts and the direct route to phenol lA is possible on Pt and Pd. The following relative rates were determined for Ni catalyst ... 

Direct oxidation of benzene to phenol is of great interest not only for its industrial importance, but also from a purely scientific point of view. Apart from many earlier reports [35] on the oxidation of benzene to phenol by hydroxyl radicals generated by the reaction of Fe2+ salt (Fenton reagent) with H202 not much is known about the homogeneously catalysed oxyfunctionalization of aromatic C-H bonds. The lack of studies is largely attributable to the fact that the activation of the C-H bond in benzene is difficult owing to its resonance stability and the reactivity of phenol, which is consecutively oxidized to quinones and other by-products. 

V.D). When the electron density in the ring is high (as in polyalkyl phenols) and the ortho- and/or para position (with respect to the OH group) is vacant, the formation of ortho- or para-benzoquinone also occurs. Indeed, in the hydroxylation of phenol to catechol and hydroquinone, one of the major side products (and the main cause of the tar formation) is the formation of benzo-quinones and products derived from them. The benzoquinones of polyalkyl-benzenes are starting materials for many products in the photographic and fine chemicals industries. Trukhan et al. 234) reported the oxidation of 2,3,-... 

Oxidations with peroxybenzoic acid are carried out in solutions in dichloromethane, chloroform, benzene, ether, or ethyl acetate at or below room temperature and include epoxidation of double bonds [295, 296, 297, 298, 299, 300, 301], oxidation of benzaldehydes to carboxylic acids or phenols [302], the Baeyer-Villiger reaction of ketones [303, 304, 305, 306, 307], and oxidation of sulfides to sulfoxides [308, 309]. Peroxybenzoic acid is also used for the anti hydroxylation of double bonds [310], the oxidation of pyrrolidines to pyrrolidones [377] and of pyrroles to succinimides [377], and the preparation of azoxy compounds from azo compounds [372]. 

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