Green Syntheses, Volume 1 / Edition 1

by Pietro Tundo, John Andraos

Overview

Many new methods directed to organic and inorganic syntheses of useful intermediates are being developed to specifically address green and sustainable chemistry principles. Highlighting the importance of green metrics, the Green Syntheses series focuses on how to reliably substantiate and validate the level of "greenness" of chemical processes, providing practical synthetic methodologies and metrics for a rigorous proof of "greenness." In Green Syntheses, Volume 1, the first book of its kind, the editors determine appropriate material efficiency green metrics and use them to compare syntheses provided by the chapter authors with those previously published.

Presenting a new concept in green chemistry, this book demonstrates what future publications might look like if green principles are followed and also incorporate the important ethical aspect of supplying rigorous procedures in laboratory practice and evidence of greenness of a given synthesis protocol using metrics analysis. This inaugural volume initiates the much-needed transition from stating the 12 guiding principles on the philosophy of green chemistry to the actualization and verification of it.

The book addresses primarily the issue of material efficiency metrics, which measure the amount of waste produced relative to desired product. In each contributed example, full experimental details are given showing all quantities of materials used in the procedure. Authors discuss the green merits of their protocols in conjunction with the results of a thorough metrics analysis, allowing for in-depth discussion of insights about synthesis strategy and performance characteristics of the new and prior cited plans.

Product Details

ISBN-13:	9780367378639
Publisher:	Taylor & Francis
Publication date:	09/05/2019
Pages:	246
Product dimensions:	6.12(w) x 9.19(h) x (d)

About the Author

John Andraos earned a PhD in 1992 from the University of Toronto in physical organic chemistry. He has done consulting assignments with the pharmaceutical industry on various aspects of synthesis optimization and green chemistry education, including Merck, Bioverdant, Scientific Update, Apotex Pharmaceuticals, and Row2 Technologies. Dr. Andraos is the author of 50 scientific papers in refereed journals, 8 book chapters on the subject of green chemistry metrics and education, and the book The Algebra of Organic Synthesis: Green Metrics, Design Strategy, Route Selection, and Optimization (CRC Press/Taylor & Francis, 2012). In 2000 he launched the CareerChem website (http://www.careerchem.com/MainFrame.html), and he is now a full-time consultant with CareerChem in Toronto, Canada.

Pietro Tundo is professor of organic chemistry at Ca’ Foscari University of Venice (Italy). He is holder of the Unesco Chair on Green Chemistry (UNTWIN No. 731) and author of approximately 260 scientific publications and 30 patents. He authored the book Continuous Flow Methods in Organic Synthesis (E. Horwood, Chichester, UK, 1991) and is editor of approximately 15 books. Dr. Tundo was president of the Organic and Biomolecular Chemistry Division of IUPAC (biennium 2007–2009) and presently is chairman of the Working Party on Green and Sustainable Chemistry of the European Association for Chemical and Molecular Sciences (EuCheMS). He is founder of the IUPAC International Conferences Series on Green Chemistry.

Table of Contents

Preface vii

About the Editors ix

Contributors xi

Chapter 1 Introduction to the Green Syntheses Series Pietro Tundo John Andraos 1

Chapter 2 Application of Material Efficiency Metrics to Assess Reaction Greenness: Illustrative Case Studies from Organic Syntheses John Andraos 13

Chapter 3 Reaction 1: Synthesis of 3-Benzyl-5-Methyleneoxazolidin-2-One from N-Benzylprop-2-yn-l-Amine and CO₂ Qing-Wen Song Liang-Nian He 47

Chapter 4 Reaction 2: Synthesis of the Five-Membered Cyclic Carbonates from Epoxides and CO₂ Qing-Wen Song Liang-Nian He 57

Chapter 5 Green Methods for the Epoxidation of Olefins Part I: Using Venturello Anion-Based Catalysts Yunxiang Qiao Zhenshan Hou 65

Chapter 6 Green Methods for the Epoxidation of Olefins Part II: Using Lacunary-Type Phosphotungstate Anion-Based Catalysts Yunxiang Qiao Zhenshan Hou 77

Chapter 7 Solvent-Free Flavone Synthesis Reaction Using KHSO₄ as Recyclable Catalyst Ángel G. Sathicq Diego M. Ruiz Gustavo P. Romanelli 101

Chapter 8 Waste-Minimized Synthesis of γ-Nitroketones Eleonora Ballerini Ferdinando Pizzo Luigi Vaccaro 111

Chapter 9 Green Syntheses of Ethers and Esters Using Dimethyl Carbonate Amarajothi Dhakshinamoorthy Kuppusamy Kanagaraj Kasi Pitchumani 123

Chapter 10 Synthesis of Ethyl Octyl Ether by Reaction between 1-Octanol and Ethanol over Amberlyst 70 Jordi Guilera Eliana Ramírez Montserrat Iborra Javier Tejero Fidel Cunill 133

Chapter 11 Reaction: Organocatalytic Asymmetric Tandem Epoxidation-Passerini Reaction Arlene G. Corrêa Máreio W. Paixão Anna M. Deobald Daniel G. Rivera 139

Chapter 12 Reaction: Green Synthesis of Chalcone and Coumarin Derivatives via a Suzuki Cross-Coupling Reaction Lucas C. C. Vieira Máreio W. Paixão Arlene G. Corrêa 149

Chapter 13 Enzymatic-Synthesized Hydroxy-L-Prolines as Asymmetric Catalysts for Green Synthesis Lo'ay A. Al-Momani 163

Chapter 14 Green Synthesis of Homoallylic Silyl Ethers Matthew R. Dintzner 183

Chapter 15 Environmentally Friendly Synthesis of Norstatines in Water Ermal Ismalaj Ferdinando Pizzo Luigi Vaccaro 193

Chapter 16 Five-Membered N- and O-Heterocycles by Dimethyl Carbonate Chemistry Fabio Aricò Pietro Tundo 205

Acronym Index 219

Compound Index 223

Formula Index 229

Subject Index 233