Autoxidation of Isopropylbenzene

Armstrong, G. P.; Hall, Ross H.; Quin, D. C.

doi:10.1038/164834a0

Cited by 11 publications

(3 citation statements)

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“…Four variables were studied: temperature, sodium naphthenate concentration, ozone partial pressure, and initiation time. Their influences on overall conversion of Knopf, 1966;Sotelo et al, 1984" Simanov and Nemtsov, I960;6 Armstrong et al, 1949* Wagner, 1965Sotelo et al, 1983;* Hock and Lang, 1944 " T = 115 °C. 6Transition-metal oxides or organic salts. "…”

Section: Resultsmentioning

confidence: 99%

Liquid-phase oxidation of cumene initiated by ozone in the presence of sodium cyclohexanecarboxylate

Sotelo¹,

Beltrán²,

Beltrán‐Heredia³

et al. 1985

Ind. Eng. Chem. Prod. Res. Dev.

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Liquid-phase oxidation of cumene initiated by ozone using sodium naphthenate as a catalyst has been investigated. The effects of temperature, catalyst concentration, ozone partial pressure, and initiation time have been studied. Maximum selectivities and yields of cumene hydroperoxide of about 65 % and 85 %, respectively, were reached. Likewise, a mechanism and kinetic equation for hydroperoxide formation were deduced. In this mechanism, the bimolecular hydroperoxide decomposition and the catalyst attack on hydroperoxide constitute the initiation step in the autoxidation period. Finally, the kinetic equation reproduces experimental hydroperoxide concentrations within a 15% deviation.

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Section: Resultsmentioning

confidence: 99%

Liquid-phase oxidation of cumene initiated by ozone in the presence of sodium cyclohexanecarboxylate

Sotelo¹,

Beltrán²,

Beltrán‐Heredia³

et al. 1985

Ind. Eng. Chem. Prod. Res. Dev.

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“…The findings of Hock and Lang lead to the technical method of cumene-phenol processing by the decomposition of cumene hydroperoxide to phenol and acetone through strong acids. Oxidation of cumene was later carried out in aqueous-alkaline emulsion at 80-140°C and later by homogenous oxidation 19,20 at 120-130°C.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Alkylaromatics

Rao

Awasthi

2006

Journal of Chemistry

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Hydroperoxide atα-position to the aromatic ring is the primary oxidation product formed. In all cases monoalkylbenzenes lead to the formation of benzoic acid. Oxidation in the presence of transition metal salts not only accelerate but also selectively decompose the hydroperoxides. Alkyl naphthalenes mainly produce the corresponding naphthalene carboxylic acids. Hock-rearrangement by the influence of strong acids converts the hydroperoxides to hemiacetals. Peresters formed from the hydroperoxides undergo Criegee rearrangement easily. Alkali metals accelerate the oxidation while CO2as co-oxidant enhances the selectivity. Microwave conditions give improved yields of the oxidation products.

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“…The effects of the catalyst type and concentration on the yield and product distribution in the decomposition reaction of 2-IPNHP are not available in the literature. However, the decomposition ofsthe key intermediate of the analogous reaction pathwayscumene hydroperoxide (CHP) into phenol and acetone has been extensively studied in the presence of H 2 SO 4 (Armstrong, 1950;Kharasch et al, 1950;Topchiev et al, 1964;Pujado et al, 1976;Hatch and Matar, 1978;Wallace, 1996), and this catalyst is currently used in several industrial phenol production plants (Pujado, 1990;Shelpakova et al, 1991;Jordan et al, 1991;Weissermel and Arpe, 1993;Wallace, 1996). The catalytic activities of HClO 4 and HCl in the CHP decomposition process are also reported (Kharasch et al, 1950;Tobolsky and Mesrobian, 1954;Kislina et al, 1988;Kislina et al, 1990;Vinnik et al, 1990).…”

Section: Introductionmentioning

confidence: 99%

Decomposition of 2-Isopropylnaphthalene Hydroperoxide into 2-Naphthol and Acetone in the Presence of Acetic Acid and H₂O₂

Boyacı

Takaç

Özdamar

1999

Ind. Eng. Chem. Res.

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Process conditions for the acid-catalyzed decomposition of 2-isopropylnaphthalene hydroperoxide (2-IPNHP) into 2-naphthol and acetone were investigated in the presence of acetic acid and H2O2 as the solvent and oxidizing reagent, respectively. 2-Naphthol and acetone are produced from 2-IPNHP by the ionic decomposition mechanism; however, reaction conditions that lead to the formation of radicals mainly favor the byproducts dimethyl-2-naphthylcarbinol (DMNC) and acetonaphthone (AN). The effects of the catalyst type and concentration on the 2-naphthol yield and on the product distribution were investigated by HClO4, H2SO4, H3PO4, and HCl. The catalytic activities of the acids in the decomposition of 2-IPNHP to produce 2-naphthol decreased in the order HClO4 > H2SO4 > HCl > H3PO4 depending on their acid strengths in acetic acid. The higher the catalyst concentration employed, the higher the 2-naphthol yield obtained. The high concentrations of 2-IPNHP did not lead to the hydroperoxide-induced decomposition reactions; instead they increased the ionic decomposition rate due to the polar character of 2-IPNHP. The increase in the DMNC concentration in the decomposition medium slightly decreased the 2-naphthol production rate and yield. The increase in temperature in the range of 22−40 °C increased the 2-naphthol production. The process conditions such as low acid strength, low catalyst concentration, and high temperature that lead to radical reactions increased the production of AN. The other byproduct DMNC was also oxidized to 2-IPNHP with H2O2 in the reactor. A 61% yield of 2-naphthol was obtained under the batch reactor conditions of 0.114 mol dm-3 HClO4 and 1.036 mol dm-3 initial 2-IPNHP concentrations at 22 °C.

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Autoxidation of Isopropylbenzene

Cited by 11 publications

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Liquid-phase oxidation of cumene initiated by ozone in the presence of sodium cyclohexanecarboxylate

Liquid-phase oxidation of cumene initiated by ozone in the presence of sodium cyclohexanecarboxylate

Oxidation of Alkylaromatics

Decomposition of 2-Isopropylnaphthalene Hydroperoxide into 2-Naphthol and Acetone in the Presence of Acetic Acid and H₂O₂

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Autoxidation of Isopropylbenzene

Cited by 11 publications

References 0 publications

Liquid-phase oxidation of cumene initiated by ozone in the presence of sodium cyclohexanecarboxylate

Liquid-phase oxidation of cumene initiated by ozone in the presence of sodium cyclohexanecarboxylate

Oxidation of Alkylaromatics

Decomposition of 2-Isopropylnaphthalene Hydroperoxide into 2-Naphthol and Acetone in the Presence of Acetic Acid and H2O2

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Decomposition of 2-Isopropylnaphthalene Hydroperoxide into 2-Naphthol and Acetone in the Presence of Acetic Acid and H₂O₂