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Green and Sustainable Solvents in Chemical Processes Coby J Review Cite This: Chem. Rev. 2018, 118, 747−800 pubs.acs.org/CR Green and Sustainable Solvents in Chemical Processes Coby J. Clarke, Wei-Chien Tu, Oliver Levers, Andreas Bröhl, and Jason P. Hallett* Department of Chemical Engineering, Imperial College, London SW7 2AZ, United Kingdom ABSTRACT: Sustainable solvents are a topic of growing interest in both the research community and the chemical industry due to a growing awareness of the impact of solvents on pollution, energy usage, and contributions to air quality and climate change. Solvent losses represent a major portion of organic pollution, and solvent removal represents a large proportion of process energy consumption. To counter these issues, a range of greener or more sustainable solvents have been proposed and developed over the past three decades. Much of the focus has been on the environmental credentials of the solvent itself, although how a substance is deployed is as important to sustainability as what it is made from. In this Review, we consider several aspects of the most prominent sustainable organic solvents in use today, ionic liquids, deep eutectic solvents, supercritical fluids, switchable solvents, liquid polymers, and renewable solvents. We examine not only the performance of each class of solvent within the context of the reactions or extractions for which it is employed, but also give consideration to the wider context of the process and system within which the solvent is deployed. A wide range of technical, economic, and environmental factors are considered, giving a more complete picture of the current status of sustainable solvent research and development. CONTENTS 6.1.3. Materials Processing 777 6.2. CO2 Expanded Liquids (CXLs) 778 1. Introduction 747 6.2.1. Chemical Reactions 778 1.1. Green Chemistry and Sustainability 748 6.2.2. Extractions 780 1.2. Sustainability and Solvents 748 6.3. Switchable Solvents 780 1.3. Evaluating Chemical Processes 750 6.3.1. Switchable Polarity Solvents (SPSs) 781 1.4. Economic Considerations 751 6.3.2. Switchable Hydrophobicity Solvents 2. Renewable Solvents 752 (SHSs) 782 2.1. Introduction 752 fi 6.3.3. Switchable Water (SW) 785 2.2. Integrated Biore nery 752 7. Future Outlook 786 2.3. Constraints 753 Author Information 787 2.4. Solvents Derived from Cellulose and Starch 753 Corresponding Author 787 2.4.1. 2-MeTHF 753 γ ORCID 787 2.4.2. -Valerolactone (GVL) 754 Notes 787 2.4.3. Cyrene 756 Biographies 787 Downloaded via LEBANESE AMERICAN UNIV on August 4, 2018 at 13:22:51 (UTC). 3. Ionic Liquids (ILs) 757 Acknowledgments 788 3.1. Introduction 757 References 788 See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles. 3.2. Environmental Impacts 758 3.3. Economic Viability of Ionic Liquids 760 3.4. Renewable Ionic Liquids 762 1. INTRODUCTION 4. Deep Eutectic Solvents (DES) 763 4.1. Introduction 763 In 2015, the UN outlined a new sustainability focused development plan under the title “Transforming Our World: 4.2. Toxicity of DES 764 ” 1 4.3. Applications of DES 766 The 2030 Agenda for Sustainable Development . The plan is 5. Liquid Polymers 767 composed of 17 sustainable development goals (SDGs) that 5.1. Polyethylene Glycol (PEG) and Polypropy- address a wide range of issues, many of which recognize the lene Glycol (PPG) Properties 767 need for green and sustainable chemistry and engineering. This 5.2. Separations and Extractions Using PEG 767 ambitious project highlights the role of sustainable imperatives 5.3. Organic Synthesis in PEG 768 as drivers for chemical research, which provide new challenges, 5.4. Synthesis of Nanomaterials and Polymers 770 opportunities, and importantly, direction. Sustainability has 6. CO2 Tunable Solvents 770 6.1. Supercritical CO2 (scCO2) 771 Special Issue: Sustainable Chemistry 6.1.1. Extractions 771 Received: September 18, 2017 6.1.2. Chemical Synthesis 773 Published: January 4, 2018 © 2018 American Chemical Society 747 DOI: 10.1021/acs.chemrev.7b00571 Chem. Rev. 2018, 118, 747−800 Chemical Reviews Review previously been described by Csefalvaý et al.: “Resources A number of alternative chemical procedures have been including energy should be used at a rate at which they can be proposed to help reduce the amount of toxic, harmful organic replaced naturally and the generation of waste cannot be faster solvents in use. Mechanochemistry can be used to eliminate the − than the rate of their remediation.”2 The concept of sustainable usage of solvents altogether;20 22 however, these processes are chemistry is well established.3,4 limited by slow reaction rates, high capital costs, and low energy Large quantities of organic solvents, relative to reagents, are efficiencies. Replacing harmful organic solvents with less usually essential for chemical reactions to proceed. In addition, harmful organic solvents (e.g., chloroform with ethanol) can many extractions, purifications, and cleaning processes also offer simple solutions; however, such substitutions can be depend on solvents, with large excesses necessary to achieve synthetically restricting and may be economically unfeasible. sufficient product purity. The annual industrial-scale production This Review aims to describe an overview of chemical of organic solvents has been estimated at almost 20 million MT processes employing neoteric solvents that are proposed as (metric tons).5 The excessive consumption of nonrenewable, sustainable alternatives. The following sections cover a wide toxic solvents is environmentally detrimental and an out- range of neoteric solvents with very different properties, each standing example of unsustainable practices. Nonetheless, suited to particular applications or processes. Moreover, the solvents are essential for many chemical processes, and chosen solvents are at various stages of development, meaning solvation provides several major advantages, such as selectivity that the challenges facing each solvent are significantly different. control, safety (for example, as a heat sink or containment of We aim to place an emphasis on the environmental and any toxic reagents), and improved handling.6 Reichardt and economic impacts of implementing developed neoteric solvents Welton have published a detailed description of the role of as the technical aspects have been covered elsewhere.9,23,24 solvents and their effects in organic chemical reactions.7 However, the technical aspects of more recent neoteric solvents The fine chemical and pharmaceutical industries have are considered in a sustainable context. Examples of sustainable previously been identified as significant sources of chemical solvent processes include, but are not limited to, solvents waste.8 This is largely due to the production of complex derived from renewable sources such as biomass, solvents molecules, which require large quantities of solvent during designed to facilitate product isolation and reaction workups, synthesis and purification. For example, the raw materials solvents that may be tuned to improve reaction outcomes, and needed to prepare active pharmaceutical ingredients (APIs) can solvents that possess little to no environmental risk. 9 be up to 85% solvent by mass. Furthermore, solvent 1.1. Green Chemistry and Sustainability requirements do not decrease for many drug manufacturing The objective of green chemistry is to reduce the usage and processes as they pass from early stage development to production of hazardous substances for chemical processes, commercial processes.10 Efforts to address these issues are a while reducing energy consumption and moving toward central part of sustainable development, and many industrial renewable sources. In an effort to guide researchers toward processes are now being scrutinized for solvent consump- − this goal, Anastas and Werner published the 12 principles of tion.11 13 However, in terms of absolute volume, large-scale green chemistry in 1998.25 Today, green chemistry is sectors such as the oil refining industry (106−108 tonnes considered a tool for introducing sustainable concepts at the product, E-factor <0.1) and bulk chemicals industry (104−106 fundamental level and therefore aimed toward inventing new tonnes product, E-factor <1−5) produce more waste than the products, routes, and processes, rather than improving existing fine chemical or pharmaceutical sectors (product tonnage 10− 26,27 3 14,15 ones. Many published articles claim to provide green 10 , E-factor 25−100). Hence, regardless of material or 28 alternatives to existing processes, often by stating how their process efficiency, significant progress can be made by moving research complies with one or more of the green principles. toward more sustainable solvent alternatives. Winterton argues that such strategies are in fact “green In recent years, environmental directives and legislation have herrings”, and consideration must be given to the larger sought to reduce solvent emissions (such as the Clean Air Act context, particularly in terms of scalability, economics, and of 1990 and the European Union Solvents Emission Directive regulatory constraints.29 This viewpoint is in accordance with 1999/13/EC) or regulate the usage of potentially harmful or sustainable chemistry, which takes a more holistic approach to environmentally damaging chemical substances (Registration, the development of chemical technologies. A multidisciplinary Evaluation, Authorisation and Restriction of Chemicals 16 approach is therefore an integral part of green and sustainable (REACH)). However, many existing chemical processes
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