Acid-catalyzed Decomposition of Cumene Hydroperoxide

Seubold, Frank H.; Vaughan, William E.

doi:10.1021/ja01111a055

Cited by 59 publications

(23 citation statements)

References 3 publications

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“…The peroxide levels found in our study would be high enough to explain their observations of H 2 O 2 . Acid catalysed decomposition has been shown to be rather slow (Miner and Hagan, 1972;Seubold and Vaughan, 1953). Based on those data, we estimate that the decomposition of the reactive peroxides by hydronium ions would be below 5 % within 60 min.…”

Section: Soa From Photo-oxidation Of α-Pinenementioning

confidence: 97%

Development of a sensitive long path absorption photometer to quantify peroxides in aerosol particles (Peroxide-LOPAP)

et al. 2012

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Abstract.A new off-line instrument to quantify peroxides in aerosol particles using iodometry in long path absorption spectroscopy has been developed and is called peroxide long path absorption photometer (Peroxide-LOPAP). The new analytical setup features important technical innovations compared to hitherto published iodometric peroxide measurements. Firstly, the extraction, chemical conversion and measurement of the aerosol samples are performed in a closed oxygen-free (∼ 1 ppb) environment. Secondly, a 50-cm optical detection cell is used for an increased photometric sensitivity. The limit of detection was 0.1 µM peroxide in solution or 0.25 nmol m −3 with respect to an aerosol sample volume of 1 m 3 . The test reaction was done at a constant elevated temperature of 40 • C and the reaction time was 60 min.Calibration experiments showed that the test reaction with all reactive peroxides, i.e. hydrogen peroxide (H 2 O 2 ), peracids and peroxides with vicinal carbonyl groups (e.g. lauroyl peroxide) goes to completion and their sensitivity (slope of calibration curve) varies by only ±5 %. However, very inert peroxides have a lower sensitivity. For example, tert-butyl hydroperoxide shows only 37 % sensitivity compared to H 2 O 2 after 1 h. A kinetic study revealed that even after 5 h only 85 % of this inert compound had reacted.The time trends of the peroxide content in secondary organic aerosol (SOA) from the ozonolysis and photooxidation of α-pinene in smog chamber experiments were measured. The highest mass fraction of peroxides with 34 % (assuming a molecular weight of 300 g mol −1 ) was found in freshly generated SOA from α-pinene ozonolysis. Mass fractions decreased with increasing NO levels in the photooxidation experiments. A decrease of the peroxide content was also observed with aging of the aerosol, indicating a decomposition of peroxides in the particles.

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Section: Soa From Photo-oxidation Of α-Pinenementioning

confidence: 97%

Development of a sensitive long path absorption photometer to quantify peroxides in aerosol particles (Peroxide-LOPAP)

et al. 2012

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“…The effect of acid activation, catalyst quantity, concentration of CHP and temperature were optimized using activated bentonite catalyst. An ionic decomposition mechanism has been suggested for the decomposition of CHP by bentonite catalyst (Scheme 2), which is analogous to a mechanism reported in the literature [16]. The formation of byproducts depends on the strength of the acid catalyst and the reaction conditions such as temperature.…”

Section: Catalytic Studiesmentioning

confidence: 87%

“…The formation of byproducts depends on the strength of the acid catalyst and the reaction conditions such as temperature. In the presence of strong acid such as sulfuric acid at relatively high temperature, one can expect the minor olefinic product, a-methylstyrene through elimination [16]. The change in the strength of the catalyst as well as the reaction temperature changes the selectivity of the reaction products during the decomposition of CHP.…”

Section: Catalytic Studiesmentioning

confidence: 99%

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Preparation of acid-modified bentonite for selective decomposition of cumene hydroperoxide into phenol and acetone

Selvin

Hsu

Aneesh

et al. 2010

Reac Kinet Mech Cat

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Phenol is industrially produced by the Hock process, in which cumene hydroperoxide (CHP) is decomposed with sulfuric acid to obtain equimolar amounts of phenol and acetone. Use of the liquid acid requires subsequent neutralization and purification of the phenol at substantial cost, and a waste stream generation that could be avoided if an effective solid acid catalyst could be used. Modified clays exhibit attractive properties as solid acids. Acid treatment produces an increase in surface area and acidity. The present study was undertaken to modify bentonite clay by treatment with hydrochloric acid for the production of phenol and acetone via the decomposition of cumene hydroperoxide. The effects of various parameters such as acid activation, catalyst weight, concentration of CHP, reaction temperature and reusability of catalyst were studied. The results indicate that the acid-modified bentonite catalyst may be used instead of sulfuric acid for selective decomposition of CHP into phenol and acetone.

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“…The requirement of both an acid and a free-radical source for the initiation of polymerization appears to be another example of a growing class of hybrid s y s t e d in which the free-radical and ionic stages are cooperatively involved, such as some Zeigler types of polymerization2* and those recently described by Okamura et al 26 Another method of producing high polymer from a-phenylethylisonitrile was found to be accomplished by simply warming in air at 50°C. for several days monomer that which had been seeded w-ith polymer produced by the ground-glass catalyst system.…”

Section: Initiation Of Polymerization Of A-phenylethylisonitrilementioning

confidence: 98%

Polyisonitriles. II. Heterophasic catalytic synthesis of poly(α‐phenylethylisonitrile) and of poly(n‐hexylisonitrile)

Millich

Sinclair

1968

J. Polym. Sci. A‐1 Polym. Chem.

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synopsisA three-component catalytic system has been discovered, which successfully polymerizes a-phenylethylisonitrile to high polymer ( D P = 200-900) and also polymerizes n-hexylisonitrile. The catalyst componqnts ate a strong acid, a free-radical source, and a heterophase and are all necessary in this system. The use of a liquid medium in which the polymer is insoluble promotes the rate of polymerization and total yield. Poly-(a-phenylethylisonitrile), formed from monomer in a presence of oxygen and finely ground glass coated with sulfuric acid, can itself serve, in the presence of monomer and oxygen, a s a catalyst for this polymerization. Preparative details and discussion of these synthesis factors are given.

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Acid-catalyzed Decomposition of Cumene Hydroperoxide

Cited by 59 publications

References 3 publications

Development of a sensitive long path absorption photometer to quantify peroxides in aerosol particles (Peroxide-LOPAP)

Development of a sensitive long path absorption photometer to quantify peroxides in aerosol particles (Peroxide-LOPAP)

Preparation of acid-modified bentonite for selective decomposition of cumene hydroperoxide into phenol and acetone

Polyisonitriles. II. Heterophasic catalytic synthesis of poly(α‐phenylethylisonitrile) and of poly(n‐hexylisonitrile)

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