Alkylation of Phenols with Alkenes

Stroh, Rudolf; Seydel, R.; Hahn, W.

doi:10.1016/b978-0-12-395648-4.50019-2

Cited by 4 publications

(7 citation statements)

References 23 publications

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“…Isopropylation of o-and p-cresol yields rather complex product mixtures, depending on reaction conditions. o-Cresol is isopropylated under kinetic control and with aluminum phenolate as catalyst to form 6-isopropyl-2-methylphenol in good yield [178], which in turn can easily be isomerized to 4-isopropyl-2-methylphenol by treatment with catalytic amounts of sulfuric acid at 60 C [184]. Under thermodynamic control, at 300 C, and with an activated clay as catalyst, the main product is 5-isopropyl-2-methylphenol (carvacrol) [185].…”

Section: -Isopropyl-3-methylphenolmentioning

confidence: 99%

“…The alkylation of phenols with styrene, amethylstyrene, and indene can also be performed with aluminum phenolate as catalyst [178], [288]. Substitution of phenol or o-cresol with styrene takes place predominantly in the orthoposition, whereas with a-methylstyrene, mainly para substitution is found.…”

Section: Aralkylphenolsmentioning

confidence: 99%

“…p-Cresol reacts with propene in the presence of aluminum phenolate [178] or BF 3 -phosphoric acid [186] as catalysts to give 2-isopropyl-4-methylphenol and 2,6-diisopropyl-4-methylphenol under kinetic control. Conditions which establish the thermodynamic equilibrium lead to the additional formation of 3-isopropyl-4-methylphenol and 2,5-and 3,5-diisopropyl-4-methylphenols.…”

Section: -Isopropyl-3-methylphenolmentioning

confidence: 99%

“…Impregnation with metal sulfates, e.g., FeSO 4 , increases the activity of gAl 2 O 3 [176], [177]. Aluminum phenolate [178] and aqueous zinc halide -hydrogen halide solution [179] have also been used as catalysts. With these systems selectivities for thymol formation are about 75 -80 %.…”

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confidence: 99%

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Phenol Derivatives

Fiege

Voges²,

Hamamoto

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

188

175

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The article contains sections titled: 1. Alkylphenols 1.1. Physical Properties 1.2. Chemical Properties 1.3. Occurrence, Formation, Isolation 1.4. Production, General 1.4.1. Alkylation of Phenols 1.4.2. Other General Processes 1.5. Industrially Important Alkylphenols 1.5.1. Polymethylphenols 1.5.2. Ethylphenols 1.5.3. Isopropylphenols 1.5.4. sec ‐Butylphenols 1.5.5. tert ‐Butylphenols 1.5.6. tert ‐Pentylphenols 1.5.7. Higher Alkylphenols 1.5.8. Cycloalkylphenols 1.5.9. Aralkylphenols 1.5.10. Alkenylphenols 1.5.11. Indanols 2. Catechol 2.1. Physical Properties 2.2. Chemical Properties 2.3. Production 2.4. Uses 2.5. Economic Aspects 2.6. Toxicology 3. Trihydroxybenzenes 3.1. Pyrogallol 3.2. Hydroxyhydroquinone 3.3. Phloroglucinol 4. Bisphenols (Bishydroxyarylalkanes) 4.1. Physical Properties 4.2. Chemical Properties 4.3. Production 4.4. Analysis, Testing, Storage 4.5. Uses, Economic Aspects 4.6. Toxicology 5. Hydroxybiphenyls 5.1. Physical Properties 5.2. Chemical Properties 5.3. Production 5.4. Analysis, Quality Specifications, Storage 5.5. Uses 5.6. Toxicology 6. Phenol Ethers 6.1. Properties 6.2. Production 6.3. Representative Phenol Ethers 7. Halogen Derivatives of Phenolic Compounds 7.1. Introduction 7.2. Representative Compounds

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Section: -Isopropyl-3-methylphenolmentioning

confidence: 99%

Section: Aralkylphenolsmentioning

confidence: 99%

Section: -Isopropyl-3-methylphenolmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Phenol Derivatives

Fiege

Voges²,

Hamamoto

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

188

175

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“…The goal of this work is to build on the 1884 observation of Trouton (and others) that there is a useful empirical relationship between the normal boiling temperature and the enthalpy of vaporization at T b . The first step is to unambiguously identify 32 Sandulesco-1930; 33 Read-1932; 34 Smith-1934; 35 Tsukervanik-1937; 36 Bowman-1950; 30 Rosenwald-1950; 37 Dutton-1953; 38 Bader-1957; 39 Stroh-1957; 40 Goldsmith-1958; 41 Dewar-1959. 42 m-butylphenol 519.0 5.28 0 Read-1928; 32 Read-1932; 34 Pardee-1944; 43 Bowman-1950.…”

Section: ■ Summary and Conclusionmentioning

confidence: 99%

Modified Trouton’s Rule for the Estimation, Correlation, and Evaluation of Pure-Component Vapor Pressure

2017

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Insights from the venerable Trouton’s Rule have been used to guide the development of an applied-thermodynamic method for the estimation, correlation, and evaluation of pure-component vapor pressure. Trouton’s Rule very simply and succinctly states that the entropy of vaporization of fluids at their normal boiling point is a constant (≈10.5 times the gas constant). Detailed evaluation of the data for many families of chemical compounds reveals the subtle patterns of departures from the rule, and facilitates the development of a useful new correlation. Several examples are presented to demonstrate the value of the new correlation to estimate, correlate, extrapolate, and evaluate vapor-pressure data, and to understand the patterns of vapor-pressure behavior. The methodology provides a guide for the development of thermodynamic correlations, and the resulting correlations are expected to be useful for the practice of applied thermodynamics.

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Organometallic chemistry and catalysis in industry

Parshall¹,

Putscher²

1986

J. Chem. Educ.

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The period from 1950 to 1977 was one of the most remarkable in the history of chemistry for the development of both chemical science and chemical technology. These years encompassed a virtual explosion in our knowledge of organometallic chemistry and in the use of this chemistry in catalytic processes. A whole new technology of organometallic catalysis, especially for olefin polymerization, blossomed (1). Nobel prizes were awarded to

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Alkylation of Phenols with Alkenes

Cited by 4 publications

References 23 publications

Phenol Derivatives

Phenol Derivatives

Modified Trouton’s Rule for the Estimation, Correlation, and Evaluation of Pure-Component Vapor Pressure

Organometallic chemistry and catalysis in industry

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