Green Sustainable Process for Chemical and Environmental Engineering and Science

Sustainable Organic Synthesis

Rajender Boddula, Abdullah M. Asiri, Inamuddin, Dr. Inamuddin

• Publisher: Elsevier
• Year: 2020
• Print ISBN: 9780128195390
• eBook ISBN: 9780128227602
• Topic: Technology & Engineering
• Subtopic: Chemical & Biochemical Engineering
• Index: Technology & Engineering

Green Sustainable Process for Chemical and Environmental Engineering and Science: Sustainable Organic Synthesis provides an in-depth overview in the area of organic, pharmaceutical, engineering and environmental sciences, with a focus on the purification and extraction of fine chemicals, alternative green solvents, medicinal, analytical drugs, and bioactive compounds utilizing green chemistry protocols. It also focuses on the nanocatalysis, biocatalysis, solvent-free, recyclable organocatalysis, solid-supported reagents, heterogeneous polymer reusable catalysis, and CO2 conversion to commercial chemicals, utilizing industrial strategies such as flow-reactor, microwave, ultrasonics, ball-mill, photochemical and electrochemical methods. - Covers a broad overview of sustainable organic synthesis - Outlines eco-friendly organic synthesis using novel techniques and chemical processes, i.e., photochemical, electrochemical, microwave, bio-strategies, etc. - Gives a detailed account of green, large-scale techniques in organic synthesis and their applications in pharmaceutical production - Presents cutting-edge, recent advances in industrial pharmaceuticals and the technologies involved in medicinal and organic chemistry - Provides a systematic discussion of each technology in organic synthesis, including main parameters and challenges

Chapter 1: Atom economy in green organic synthesis

Felicia Phei Lin Lim^a; Anton V. Dolzhenko^{a,b a} School of Pharmacy, Monash University Malaysia, Bandar Sunway, Selangor, Malaysia
^b School of Pharmacy and Biomedical Sciences, Curtin Health Innovation Research Institute, Curtin University, Perth, WA, Australia

Abstract

Atom economy is the second of the 12 green chemistry principles. This principle is particularly useful for the synthesis of fine organic chemicals and active pharmaceutical ingredients. The power of this principle comes from its quantifiable nature. Moreover, this metric can be applied at the stage of the synthesis planning prior to real experiments. However, atom economy as a sole criterion of the process greenness is deficient and should be applied for such assessments together with other principles. Being very important for the design of synthesis routes, atom economy may turn into a minor contributor to the overall greenness of a synthesis when experimental results become available. This chapter illustrates the role of atom economy in the synthesis of three important medicines (ibuprofen, praziquantel, and sildenafil citrate) via different synthetic routes, including commercial ones.

Keywords

Green synthesis; Green chemistry principles; Atom economy

1: Introduction

The term atom economy (AE) or atom utilization was first coined by Trost [1] and is defined as the theoretical ratio of product mass to mass of substrates in a chemical reaction. Mathematically, AE is calculated by the molecular mass of the product (C) divided by the molecular mass of the reactants (A + B) (Eq. 1) [1]. In the case of linear synthetic process and convergent-type syntheses, the AE expression should be reformulated since it is impossible to multiply the AE of each stage to obtain an overall AE of the process [2, 3]. Hence, intermediates are systematically ignored in the calculation of AE for linear (Eq. 2) and branched syntheses (Eq. 3) [2, 3].

AE is one of the oldest fundamental metrics in green chemistry. Being the second principle of Winterton's “Twelve Principles of Green Chemistry” [4], AE is one of the driving forces for a more efficient use of raw materials and minimization of waste creation. Green metrics are divided into two groups, viz., the quantitatively calculated one based on kg/kg and the one represented as percentage. AE belongs to the latter group and larger AE values correspond to greater percentage of reactants incorporated into the product [1–3]. An ideal synthesis would have an AE of 100%, which translates into the incorporation of all reactants into the final products with no by-product formation. However, it is a concept with severe limitations, prominently with disregard to molar excess of reactants, use of reactant auxiliaries (catalyst, solvents), incomplete conversion of reactants and reagents, and yield of reaction [1, 3]. Thus, in calculations of AE, an emphasis is made on the reaction stoichiometry, rendering the calculations relatively simple.

Hence, during synthetic planning, the AE concept should be considered for the predictio...

Table of contents

• Cover image
• Title page
• Table of Contents
• Copyright
• Contributors
• Chapter 1: Atom economy in green organic synthesis
• Chapter 2: Click chemistry: A tool for green chemical organic synthesis
• Chapter 3: Continuous-flow chemistry toward sustainable chemical synthesis
• Chapter 4: Nanocatalysis in green organic synthesis
• Chapter 5: Biocatalysis in green organic synthesis
• Chapter 6: Biomass-derived aqueous extracts as green solvents for organic transformations
• Chapter 7: Green organic synthesis by photochemical protocol
• Chapter 8: Anthology of heterocyclic pharmacophores synthesized under solvent-free conditions: A decade survey
• Chapter 9: Ionic liquids-assisted green organic synthesis
• Chapter 10: Green organic synthesis by carbon oxide conversion
• Chapter 11: Green organic synthesis in supercritical water
• Chapter 12: Significance of drug reprofiling and metabolic engineering in drug synthesis
• Chapter 13: Bioenzyme-assisted green organic synthesis
• Chapter 14: Environmentally sustainable organo-modification of selected metal oxides and their hybrids: Characterization, properties, and utilizations
• Chapter 15: Green organo-modification of cyclodextrin metal oxide hybrids: Characterization, properties, and applications
• Chapter 16: Recent advances in photo-irradiated synthesis of bioactive heterocycles
• Chapter 17: Tri-liquid phase transfer catalysis: A green reaction technology
• Index