1st Edition

Advances in Friedel-Crafts Acylation Reactions Catalytic and Green Processes

By Giovanni Sartori, Raimondo Maggi Copyright 2010
    216 Pages 20 B/W Illustrations
    by CRC Press

    220 Pages 20 B/W Illustrations
    by CRC Press

    Used in the production of a wide number of fine chemicals and pharmaceuticals, the Friedel-Crafts acylation reaction represents a synthetic process of great interest to organic chemists of academia and industry. Nearly 40 years since the last major treatise on the topic and reflecting the growing emphasis on green technology, Advances in Friedel-Crafts Acylation Reactions: Catalytic and Green Processes focuses on how to make this reaction more economically and environmentally friendly by using green acylating conditions, thus minimizing the formation of waste and decreasing production costs.

    Divided into four parts, the book explores stoichiometric acylations, catalytic homogeneous acylations, catalytic heterogeneous acylations, and phenol acylations. It is structured according to the role played by the catalyst in the activation of reagents as well as in the different modes of regioselectivity encountered in the acylation of arenes, aromatic ethers, and phenols.

    Incorporating examples of all acid-catalyzed Friedel-Crafts acylation reactions, the text considers classic Lewis and Brönsted acid types along with more innovative and advanced multicomponent superacid catalysts. These range from rare earth triflates or triflimides and their combination with ionic liquids to metal-promoted zeolites and zeotypes, clays, polymetal oxides, sulfated zirconia, heteropoly acids, and Nafion. The book emphasizes the major industrial applications, providing a critical assessment of the differences, advantages, and disadvantages of homogeneous and heterogeneous catalysis.

    Helping readers to better understand the mechanism of the Friedel-Crafts acylation, the examples in the book substantiate the development of more effective catalysts and more selective processes achieved during the last few decades, enabling industry to embark on a safer and more efficient synthesis of aromatic ketones for the manufacture of a wide array of products.

    Introduction and Scope

    Stoichiometric Acylations

    Acylation

    Cycloacylation

    Catalytic Homogeneous Acylations

    Metal Halides

    Trifluoroacetic Acid, Triflic Acid and (Metal) Derivatives

    Metals

    Miscellaneous

    Catalytic Heterogeneous Acylations

    Zeolites

    Clays

    Metal Oxides

    Sulphated Zirconia

    HPA

    Nafion

    Miscellaneous

    Direct Phenol Acylation – Fries Rearrangement

    Direct Phenol Acylation

    Metal phenolates

    Metal halides

    Metal triflates

    Zeolites

    Clays

    Graphite

    Fries Rearrangement

    Metal triflates

    Metal halides

    Metals

    sec-Butyllithium

    Zeolites

    HPA

    Clays

    Nafion

    Photo-Fries Rearrangement

    Biography

    Giovanni Sartori is the Head of the "Clean Synthetic Methodologies Groups" of the University of Parma in Italy. His research interests include all aspects of the heterogeneous catalysis applied to the fine chemicals and pharmaceuticals production with particular attention to the preparation and use of supported organic (chiral) catalysts. Raimondo Maggi is an Associate Professor of Organic Chemistry at the University of Parma. His research interests include the preparation and use of heterogeneous (chiral) catalysts for the environmentally friendly synthesis of fine chemicals and pharmaceuticals.

    The Friedel-Crafts acylation reaction is of interest to organic chemists in academia and industry. This work reviews the most important research on the Friedel-Crafts acylation reaction published during the past 30 years, and demonstrates how to make this reaction more economical and less damaging to the environment.

    Book News, June 2010

    The book is well structured and provides the reader with up-to-date references … New researchers in the field as well as expert industrial practitioners will find valuable insights and up-to-date references here. I would personally recommend this book to all colleagues and graduate-level students who are pursuing research in the field of synthetic manipulation of aromatic compounds, A perfect balance between historical background and new trends toward low-impact environmental strategies can be found throughout the book.

    —Marco Bandini, Università di Bologna, Journal of the American Chemical Society, Vol. 132 Issue 21-24, 2010