Friedel-Crafts alkylation of anisole in supercritical carbon dioxide: A comparative study of catalysts

Rodrigo Amandi; Peter Licence; Stephen K. Ross; Olli Aaltonen; Martyn Poliakoff

doi:10.1021/op050044y

Friedel-Crafts alkylation of anisole in supercritical carbon dioxide: A comparative study of catalysts

Rodrigo Amandi, Peter Licence, Stephen K. Ross, Olli Aaltonen, Martyn Poliakoff (Corresponding Author)

VTT Technical Research Centre of Finland

Research output: Contribution to journal › Article › Scientific › peer-review

43 Citations (Scopus)

Abstract

The Friedel−Crafts alkylation of anisole with n-propanol was carried out over five different Brønsted solid acid catalysts using supercritical carbon dioxide as the reaction medium. The reaction temperature and pressure were evaluated in terms of selectivity for the monoalkylated products, conversion of the starting material, and the products' isomeric ratio. Desulfonation of the catalysts was observed when the temperature was increased above 150 °C for the organic supported catalysts investigated Amberlyst 15 and Purolite CT-175, and above 200 to 250 °C for the inorganic supported catalysts Nafion SAC-13 and Deloxan ASP I/7. A decrease in the catalytic performance of organic supported catalysts was observed with increasing pressure. This decrease was related to the phase behaviour of the reaction.

Original language	English
Pages (from-to)	451-456
Journal	Organic Process Research and Development
Volume	9
Issue number	4
DOIs	https://doi.org/10.1021/op050044y
Publication status	Published - 2005
MoE publication type	A1 Journal article-refereed

Keywords

alkylation
Friedel-Crafts alkylation
carbon-carbon bond
catalysts
anisoles

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title = "Friedel-Crafts alkylation of anisole in supercritical carbon dioxide: A comparative study of catalysts",

abstract = "The Friedel−Crafts alkylation of anisole with n-propanol was carried out over five different Br{\o}nsted solid acid catalysts using supercritical carbon dioxide as the reaction medium. The reaction temperature and pressure were evaluated in terms of selectivity for the monoalkylated products, conversion of the starting material, and the products' isomeric ratio. Desulfonation of the catalysts was observed when the temperature was increased above 150 °C for the organic supported catalysts investigated Amberlyst 15 and Purolite CT-175, and above 200 to 250 °C for the inorganic supported catalysts Nafion SAC-13 and Deloxan ASP I/7. A decrease in the catalytic performance of organic supported catalysts was observed with increasing pressure. This decrease was related to the phase behaviour of the reaction. ",

keywords = "alkylation, Friedel-Crafts alkylation, carbon-carbon bond, catalysts, anisoles",

author = "Rodrigo Amandi and Peter Licence and Ross, {Stephen K.} and Olli Aaltonen and Martyn Poliakoff",

note = "Project code: D0SU00555",

year = "2005",

doi = "10.1021/op050044y",

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journal = "Organic Process Research and Development",

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TY - JOUR

T1 - Friedel-Crafts alkylation of anisole in supercritical carbon dioxide

T2 - A comparative study of catalysts

AU - Amandi, Rodrigo

AU - Licence, Peter

AU - Ross, Stephen K.

AU - Aaltonen, Olli

AU - Poliakoff, Martyn

N1 - Project code: D0SU00555

PY - 2005

Y1 - 2005

N2 - The Friedel−Crafts alkylation of anisole with n-propanol was carried out over five different Brønsted solid acid catalysts using supercritical carbon dioxide as the reaction medium. The reaction temperature and pressure were evaluated in terms of selectivity for the monoalkylated products, conversion of the starting material, and the products' isomeric ratio. Desulfonation of the catalysts was observed when the temperature was increased above 150 °C for the organic supported catalysts investigated Amberlyst 15 and Purolite CT-175, and above 200 to 250 °C for the inorganic supported catalysts Nafion SAC-13 and Deloxan ASP I/7. A decrease in the catalytic performance of organic supported catalysts was observed with increasing pressure. This decrease was related to the phase behaviour of the reaction.

AB - The Friedel−Crafts alkylation of anisole with n-propanol was carried out over five different Brønsted solid acid catalysts using supercritical carbon dioxide as the reaction medium. The reaction temperature and pressure were evaluated in terms of selectivity for the monoalkylated products, conversion of the starting material, and the products' isomeric ratio. Desulfonation of the catalysts was observed when the temperature was increased above 150 °C for the organic supported catalysts investigated Amberlyst 15 and Purolite CT-175, and above 200 to 250 °C for the inorganic supported catalysts Nafion SAC-13 and Deloxan ASP I/7. A decrease in the catalytic performance of organic supported catalysts was observed with increasing pressure. This decrease was related to the phase behaviour of the reaction.

KW - alkylation

KW - Friedel-Crafts alkylation

KW - carbon-carbon bond

KW - catalysts

KW - anisoles

U2 - 10.1021/op050044y

DO - 10.1021/op050044y

M3 - Article

SN - 1083-6160

VL - 9

SP - 451

EP - 456

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 4

ER -

Friedel-Crafts alkylation of anisole in supercritical carbon dioxide: A comparative study of catalysts

Abstract

Keywords

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