Autoxydation von Kohlenwasserstoffen, IX. Mitteil.: Über Peroxyde von Benzol‐Derivaten

Hock, Heinrich; Lang, S. A.

doi:10.1002/cber.19440770321

“…These reactions were first reported in 1944 by H. HOCK and S. LANG [9]. The industrial cumene oxidation process was developed and commercialized after World War II by The Distillers Co. in Great Britain and the Hercules Powder Company in the USA [10,11].…”

Section: Cumene Oxidation (Hock Process)mentioning

confidence: 97%

Phenol

Weber

¹

,

Weber

²

,

Kleine-Boymann

³

2004

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Physical Properties 3. Chemical Properties 4. Production 4.1. Cumene Oxidation (Hock Process) 4.2. Toluene Oxidation 4.3. Phenol from Coal 4.4. Other Processes 4.4.1. Sulfonation of Benzene 4.4.2. Chlorination of Benzene 4.4.3. Direct Oxidation of Benzene 5. Environmental Protection 6. Quality Specifications 7. Storage and Transportation 8. Uses and Economic Aspects 9. Toxicology and Occupational Health

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“…[1] In 2000, the worldwide production of phenol was 6.6 megatons. Most of this phenol is produced by the cumene process reported by Hock and Lang in 1944. [2] The direct conversion of benzene to phenol by hydroxylation with O 2 is the most desirable method among phenol syntheses.…”

mentioning

confidence: 99%

“…Most of this phenol is produced by the cumene process reported by Hock and Lang in 1944. [2] The direct conversion of benzene to phenol by hydroxylation with O 2 is the most desirable method among phenol syntheses. However, indirect phenol production through the formation of cumene hydroperoxide and oxidative decomposition of benzoic acid are currently employed.…”

mentioning

confidence: 99%

“…[7] In the course of our study on the coupling of benzene with acrylates in the presence of O 2 by Pd(OAc) 2 combined with molybdovanadophosphates, we found that a small amount of phenol is formed as a by-product. [11] Thus, our attention has been focused on the direct conversion of benzene (1) into phenol (2), and an efficient simple catalytic method for the synthesis of 2 from 1 using molybdovanadophosphoric acids as catalysts has been established [Eq. (1)].…”

mentioning

confidence: 99%

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Hydroxylation of Benzene to Phenol under Air and Carbon Monoxide Catalyzed by Molybdovanadophosphoric Acid

Tani

¹

,

Sakamoto

²

,

Mita

³

et al. 2005

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“…Bovine liver catalase (Sigma) was dialyzed prior to use to remove the preservative thymol. CuOOH was obtained from Aldrich and purified by extraction with alkali as described (28) prior to use. PhIO was prepared by the alkaline hydrolysis of the diacetate (29) and stored at Ϫ20°C.…”

Section: Methodsmentioning

confidence: 99%

Diversity in Mechanisms of Substrate Oxidation by Cytochrome P450 2D6

Hanna¹,

Krauser²,

Cai³

et al. 2001

Journal of Biological Chemistry

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Cytochrome P450 (P450) 2D6 was first identified as the polymorphic human debrisoquine hydroxylase and subsequently shown to catalyze the oxidation of a variety of drugs containing a basic nitrogen. Differences in the regioselectivity of oxidation products formed in systems containing NADPH-P450 reductase/NADPH and the model oxidant cumene hydroperoxide have been proposed by others to be due to an allosteric influence of the reductase on P450 2D6 (Modi, S., Gilham, D. E., Sutcliffe, M. J., Lian, L.-Y., Primrose, W. U., Wolf, C. R., and Roberts, G. C. K. (1997) Biochemistry 36, 4461-4470). We examined the differences in the formation of oxidation products of N-methyl-4-phenyl-1,2,5,6-tetrahydropyridine, metoprolol, and bufuralol between reductase-, cumene hydroperoxide-, and iodosylbenzene-supported systems. Catalytic regioselectivity was not influenced by the presence of the reductase in any of the systems supported by model oxidants, ruling out allosteric influences. The presence of the reductase had little effect on the affinity of P450 2D6 for any of these three substrates. The addition of the reaction remnants of the model oxidants (cumyl alcohol and iodobenzene) to the reductase-supported system did not affect reaction patterns, arguing against steric influences of these products on catalytic regioselectivity. Label from H 2 18 O was quantitatively incorporated into 1-hydroxybufuralol in the iodosylbenzene-but not in the reductase-or cumene hydroperoxide-supported reactions. We conclude that the P450 systems utilizing NADPH-P450 reductase, cumene hydroperoxide, and iodosylbenzene use similar but distinct chemical mechanisms. These differences are the basis for the variable product distributions, not an allosteric influence of the reductase. P4501 enzymes (also termed "heme-thiolate protein P450"; Ref. 1) are involved in the oxidations of many organic chemicals (2-4). The P450 enzymes are found in nearly all life forms, but there has been particular interest in the mammalian P450 enzymes that dominate the metabolism of drugs (5). P450s constitute an important target in pharmacogenomic efforts because variation among individual humans can have a major influence on the efficacy of drugs (6).P450 2D6 was first identified as the polymorphic enzyme involved in debrisoquine hydroxylation (7) and sparteine oxidation (8). This enzyme is involved in the metabolism of approximately one third of the drugs used today (5). P450 2D6 polymorphism is relatively well understood today (9 -11), and our own efforts have been directed to better understanding the biochemical basis of P450 2D6 activity. In our early research with purified P450 2D6 (12), the observation was made that most of the substrates of P450 2D6 contain a basic nitrogen atom, which is located ϳ5 Å away from the site of oxidation (13,14). This concept was developed with more detailed pharmacophore and homology models for P450 2D6 (15-18).A problem in modeling of P450 2D6 arose with the report of Modi et al. (19) that differences were observed between MPTP oxid...

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Autoxydation von Kohlenwasserstoffen, IX. Mitteil.: Über Peroxyde von Benzol‐Derivaten

Cited by 293 publications

References 6 publications

Phenol

Phenol

Hydroxylation of Benzene to Phenol under Air and Carbon Monoxide Catalyzed by Molybdovanadophosphoric Acid

Diversity in Mechanisms of Substrate Oxidation by Cytochrome P450 2D6

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