New Friedel-Crafts chemistry. 34. Production of branched alkanes by acid-catalyzed dealkylation of linear alkylbenzenes

Roberts, Royston M.; Chen, Hoffman Hor-Fu; Junhasavasdikul, Banja

doi:10.1021/jo00409a009

Cited by 4 publications

(1 citation statement)

References 6 publications

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“…The relative rate of alkylbenzene dealkylation was found to be in the order tertiary > secondary > primary alkyl. [47][48][49] Alkylbenzenes with sec-alkyl groups, like 5, are consequently more difficult to dealkylate and can therefore accumulate, while those with tert-alkyl groups, like 4, are subject to constant dealkylation and realkylation (Figure 10). Under reaction conditions where 4 is the main or only product, the reaction is kinetically controlled, while reactions under equilibrium control would yield 5 as a major product.…”

Section: Discussionmentioning

confidence: 99%

Alkylation of Benzene with 1-Pentene over Solid Phosphoric Acid

Cowley

Klerk

Nel

et al. 2006

Ind. Eng. Chem. Res.

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The solid phosphoric acid (SPA) catalyzed alkylation of benzene with 1-pentene was studied in the range 160−220 °C, 3.8 MPa, and with aromatic to olefin ratios in the range 6:1−1:6. It could be shown that SPA has the potential to be a selective alkylation catalyst for the production of linear alkyl benzenes (LABs) even at low aromatic to olefin ratios, provided that reaction pathways leading to skeletal isomerization can be suppressed. It was also found that steric effects were more important than electronic effects in governing the alkylation selectivity of SPA and that a protonated cyclopropane structure was the most likely transition-state for alkylation that followed an Eley−Rideal mechanism. Laboratory and pilot plant studies indicated that the carbon chain length of the product was limited to C15, with less than 5% di-alkylation of benzene taking place, even for reactions at 1:6 aromatic to olefin ratio.

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Section: Discussionmentioning

confidence: 99%

Alkylation of Benzene with 1-Pentene over Solid Phosphoric Acid

Cowley

Klerk

Nel

et al. 2006

Ind. Eng. Chem. Res.

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ChemInform Abstract: NEW FRIEDEL‐CRAFTS CHEMISTRY. 34. PRODUCTION OF BRANCHED ALKANES BY ACID‐CATALYZED DEALKYLATION OF LINEAR ALKYLBENZENES

Roberts¹,

Chen²,

Junhasavasdikul³

1978

Chemischer Informationsdienst

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Säurekatalysierte Umsetzungen von Aromaten mit Alkanen und Cycloalkanen. X. Alkylierungen mit Cyclohexan

1983

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Acid‐catalyzed Reactions of Aromatic Hydrocarbons with Alkanes and Cycloalkanes. X. Alkylations with Cyclohexane The complex reaction mixtures of the nonconventional alkylation of benzene with cyclohexane in the presence of Lewis/proton acids and promotors were investigated by gas‐liquid chromatography and mass spectrometry. Four representative groups of hydrocarbons were found including cycloalkylbenzenes, substituted indanes or tetralines (C12H16), C1‐C6‐alkylbenzenes and isomeric biscycloalkyls (C12H22). Their formation is interpreted as a competition between alkylation, (without or with isomerization), ringfission with cycloalkylation or fragmentation, and self‐alkylation; phenylcycloalkylcations and phenylalkylcations are the intermediates.

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New Friedel-Crafts chemistry. 34. Production of branched alkanes by acid-catalyzed dealkylation of linear alkylbenzenes

Cited by 4 publications

References 6 publications

Alkylation of Benzene with 1-Pentene over Solid Phosphoric Acid

Alkylation of Benzene with 1-Pentene over Solid Phosphoric Acid

ChemInform Abstract: NEW FRIEDEL‐CRAFTS CHEMISTRY. 34. PRODUCTION OF BRANCHED ALKANES BY ACID‐CATALYZED DEALKYLATION OF LINEAR ALKYLBENZENES

Säurekatalysierte Umsetzungen von Aromaten mit Alkanen und Cycloalkanen. X. Alkylierungen mit Cyclohexan

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