Biobased surfactants : synthesis, properties, and applications PDF
Preview Biobased surfactants : synthesis, properties, and applications
BIOBASED SURFACTANTS BIOBASED SURFACTANTS Synthesis, Properties, and Applications SECOND EDITION Edited by Douglas G. Hayes Daniel K.Y. Solaiman Richard D. Ashby Academic Press and AOCS Press Academic Press is an imprint of Elsevier 125 London Wall, London EC2Y 5AS, United Kingdom 525 B Street, Suite 1650, San Diego, CA 92101, United States 50 Hampshire Street, 5th Floor, Cambridge, MA 02139, United States The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, United Kingdom Copyright © 2019 AOCS Press. Published by Elsevier Inc. All rights reserved. Published in cooperation with American Oil Chemists’ Society www.aocs.org Director, Membership and Publications, Janet Brown No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any information storage and retrieval system, without permission in writing from the publisher. Details on how to seek permission, further information about the Publisher’s permissions policies and our arrangements with organizations such as the Copyright Clearance Center and the Copyright Licensing Agency, can be found at our website: www.elsevier.com/permissions. This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). Notices Knowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary. Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility. To the fullest extent of the law, neither the Publisher nor the authors, contributors, or editors, assume any liability for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions, or ideas contained in the material herein. Library of Congress Cataloging-in-Publication Data A catalog record for this book is available from the Library of Congress British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library ISBN 978-0-12-812705-6 For information on all Academic Press publications visit our website at https://www.elsevier.com/books-and-journals Publisher: Charlotte Cockle Acquisition Editor: Nancy Maragioglio Editorial Project Manager: Michelle Fisher Production Project Manager: Vignesh Tamil Cover Designer: Matthew Limbert Typeset by SPi Global, India Contributors Edgar Acosta Department of Chemical Engi- Rudolf Hausmann Department of Bioprocess neering and Applied Chemistry, University of Engineering, Institute of Food Science and Bio- Toronto, Toronto, ON, Canada technology, University of Hohenheim, Stutt- gart, Germany Sampson Anankanbil Department of Engineer- ing, Faculty of Science and Technology, Aarhus Douglas G. Hayes Department of Biosystems University, Aarhus, Denmark Engineering and Soil Science, University of Tennessee, Knoxville, TN, United States Richard D. Ashby Eastern Regional Research Center, Agricultural Research Service, US Yongjin He Department of Engineering, Faculty Department of Agriculture, Wyndmoor, PA, of Science and Technology, Aarhus University, United States Aarhus, Denmark; College of Life Science, Fujian Normal University, Fuzhou, China Long Bai Department of Bioproducts and Bio- systems, School of Chemical Engineering, Aalto Marius Henkel Department of Bioprocess University, Aalto, Finland Engineering, Institute of Food Science and Biotechnology, University of Hohenheim, Alexander Beck Institute of Interfacial Engi- Stuttgart, Germany neering and Plasma Technology IGVP, Univer- sity of Stuttgart, Stuttgart, Germany Krutika Invally Department of Chemical and Biomolecular Engineering, The University of Neil W. Boaz Eastman Chemical Company, Akron, Akron, OH, United States Kingsport, TN, United States François Jérome Ecole Nationale Superieure Jiazhi Chen Guangdong Provincial Key Labo- d’Ingenieurs de Poitiers, Institut de Chimie des ratory of Industrial Surfactant, Guangdong Milieux et Materiaux de Poitiers (IC2MP, Research Institute of Petrochemical and Fine UMR7285), University of Poitiers, Poitiers Chemical Engineering, Guangzhou, P. R. Cedex, France China Lu-Kwang Ju Department of Chemical and Bio- Stephanie K. Clendennen Eastman Chemical molecular Engineering, The University of Company, Kingsport, TN, United States Akron, Akron, OH, United States Mª del Carmen Morán Biochemistry and Phys- Toshio Kakui LION Corporation, Sumida-ku, iology Department, Physiology Section, Phar- Tokyo, Japan macy and Food Sciences, Barcelona University, Jingbo Li Department of Engineering, Faculty Barcelona, Spain of Science and Technology, Aarhus University, Boris Estrine Agro Industrie Recherches et Aarhus, Denmark; Department of Chemical Développements, Pomacle, France Engineering, Massachusetts Institute of Tech- Mareen Geissler Department of Bioprocess nology, Cambridge, MA, United States Engineering, Institute of Food Science and Bio- Sofie Lodens Faculty of Bioscience Engineer- technology, University of Hohenheim, Stutt- ing, Centre for Industrial Biotechnology and gart, Germany Biocatalysis (InBio.be), Ghent University, Zheng Guo Department of Engineering, Faculty Ghent, Belgium of Science and Technology, Aarhus University, Sinisa Marinkovic Agro Industrie Recherches Aarhus, Denmark et Développements, Pomacle, France ix x CONTRIBUTORS Kambiz Morabbi Heravi Department of Bio- Cosima Stubenrauch Institute of Physical process Engineering, Institute of Food Science Chemistry, University of Stuttgart, Stuttgart, and Biotechnology, University of Hohenheim, Germany Stuttgart, Germany Sang-Jin Suh Department of Biological Sci- Lourdes Pérez IInstitute for Advanced Chemis- ences, Auburn University, Auburn, AL, United try of Catalonia, IQAC-CSIC, Barcelona, Spain States Aurora Pinazo Institute for Advanced Chemis- Suryavarshini Sundar Department of Chemical try of Catalonia, IQAC-CSIC, Barcelona, Spain Engineering and Applied Chemistry, Univer- Ramon Pons Institute for Advanced Chemistry sity of Toronto, Toronto, ON, Canada of Catalonia, IQAC-CSIC, Barcelona, Spain Blaise Tardy Department of Bioproducts and Sang-Hyun Pyo Department of Biotechnology, Biosystems, School of Chemical Engineering, Aalto University, Aalto, Finland Center for Chemistry and Chemical Engineer- ing, Lund University, Lund, Sweden Norio Tobori LION Specialty Chemicals Co., Sophie Roelants Faculty of Bioscience Engi- Ltd., Sumida-ku, Tokyo, Japan neering, Centre for Industrial Biotechnology Lisa Van Renterghem Faculty of Bioscience and Biocatalysis (InBio.be), Ghent University; Engineering, Centre for Industrial Biotechnol- Bio Base Europe Pilot Plant, Ghent, Belgium ogy and Biocatalysis (InBio.be), Ghent Univer- Orlando J. Rojas Department of Bioproducts sity, Ghent, Belgium and Biosystems, School of Chemical Engineer- Nicole Werner Fraunhofer Institute for Interfa- ing, Aalto University, Aalto, Finland cial Engineering and Biotechnology IGB, Stutt- George A. Smith Sasol Performance Chemicals gart, Germany North America LLC, Westlake, LA, United States Wenchao Xiang Department of Bioproducts Wim Soetaert Faculty of Bioscience Engineer- and Biosystems, School of Chemical Engineer- ing, Aalto University, Aalto, Finland ing, Centre for Industrial Biotechnology and Biocatalysis (InBio.be), Ghent University; Bio Ran Ye Roha USA, St. Louis, MO, United States Base Europe Pilot Plant, Ghent, Belgium Susanne Zibek Institute of Interfacial Engineer- Daniel K.Y. Solaiman Eastern Regional ing and Plasma Technology IGVP, University of Research Center, Agricultural Research Service, Stuttgart; Fraunhofer Institute for Interfacial US Department of Agriculture, Wyndmoor, PA, Engineering and Biotechnology IGB, Stuttgart, United States Germany Introduction As we wrote in the introduction of the become more efficient and economically and First Edition of Biobased Surfactants in 2008, environmentally friendly, partly as a result “for the majority of the 20th century, pe- of technological developments in biotechnol- troleum was utilized as the main feedstock ogy, catalyst development, and green chem- for transportation and other fuels, chemical istry. Some examples include the increased intermediates, and many co-products. The performance of microorganisms to pro- Surfactants and Detergents industrial sector, duce surfactants utilizing lower-cost carbon like many others, relied heavily upon petro- sources (“biosurfactants”) and production of leum as its main feedstock.” medium-chain fatty acids by algae through When the First Edition was being pre- metabolic engineering and improved cata- pared, a major driving force for the interest in lysts (e.g., the Grubbs catalyst employed for biobased surfactants was the concern of the metathesis and the Shvo catalyst for conduct- increasing price and decreasing availability ing oxidation-reduction) to enhance process of petroleum. However, after the publication selectivity. In addition, several new and of the First Edition, the price of petroleum has emerging biobased surfactants have been decreased greatly due to its increased pro- developed, for example, new amino acid sur- duction as a result of improved “fracking,” factants designed for several different non- tertiary oil recovery, and other technological food applications. advances, applied particularly to recover re- The developments described above moti- sidual amounts of oil from previously retired vated us to prepare the Second Edition. A few oil wells in the Southwest United States and of the chapters are updated versions of chap- from the sand shales of North Dakota and ters written for the First Edition, but even Alberta. these chapters contain new information. Yet, the manufacture and utilization of We added several new chapters on import- biobased surfactants has continued to in- ant topics not directly addressed in the First crease over the past 10 years, now reaching Edition, including methyl ethyl sulfonates, 24% of the surfactant market, with continued fatty acid ethoxylates, betaines, phospholip- growth expected. The increase is likely due ids, and lipopeptide biosurfactants. to increased concern for climate change by We are thankful for the chapter authors consumers and retailers as extreme climatic for their diligence in preparing 15 outstand- changes and events have been observed to ing chapters. We deeply appreciate the in- an increasing extent in recent years. The in- volvement and support of the American Oil creased interest and utilization was observed Chemists’ Society. The original concept of in Europe first, followed by North America, this book originated after the first sympo- and now is expected to follow suit in Asia. sium on Biobased Surfactants at the AOCS Since the publication of the First Edition, Annual Meeting in Quebec City in 2007. This the production of biobased surfactants has symposium has been given in every year xi xii INTRODUCTION since this date. We thank the editorial staff and that it will inspire you to serve as an of Elsevier for their patience and kind assis- advocate for the preparation of chemicals, tance in preparing this book. We hope you materials, and other products from renew- find this book useful for your own research able resources using green manufacturing and development in biobased s urfactants principles. Douglas G. Hayes Daniel K.Y. Solaiman Richard D. Ashby C H A P T E R 1 Biobased Surfactants: Overview and Industrial State of the Art † Douglas G. Hayes*, George A. Smith ⁎Department of Biosystems Engineering and Soil Science, University of Tennessee, Knoxville, TN, United States †Sasol Performance Chemicals North America LLC, Westlake, LA, United States 1.1 WHAT ARE BIOBASED SURFACTANTS? Surfactants, molecules that adhere to interfaces (e.g., water-oil, liquid-gas, and solid-liquid or -gas) and lower their surface energy, have numerous applications in our everyday lives, including foods, medicines, toiletries, cleaners, automotive fluids, paints and coatings, and processing aids. Their surface activity is enabled by their molecular structure, consisting of separated hydrophilic and lipophilic domains. As one adds surfactant to a two-phase sys- tem (e.g., water and oil), the concentration of surfactant adsorbed at the fluid-fluid interface increases, and concurrently, the surface energy (i.e., interfacial tension) decreases until the interface becomes saturated in surfactant, known as the critical micelle concentration (CMC). As surfactant concentration exceeds the CMC, the surface tension remains relatively constant, and the excess surfactant frequently forms self-assembly systems such as micelles. The inter- facial tension for a liquid-gas system is commonly referred to as the “surface tension.” Surfactants can be categorized by their chemistry, particularly that of their polar moiety, or “head group”: cationic, anionic, amphoteric, or nonionic. The relative strength of hydrophilic and lipophilic moieties in a surfactant (known as hydrophilic-lipophilic balance, or HLB) determines the nature of their surface activity, whether they are able to dissolve water into oil (more lipophilic), oil into water (more hydrophilic), or nearly balanced in hydrophilicity and lipophilicity, allowing them to form bicontinuous and lamellar structures. Surfactants’ HLB values can be tuned by environmental factors such as temperature (which increases the polar- ity of ionic surfactants and the lipophilicity of alkyl ethoxylate nonionic surfactants) and sa- linity (which decreases the hydrophilicity of ionic surfactants via Debye shielding). The ideal surfactant is described as inducing a low surface or interfacial tension and possessing low Krafft point temperature; high solubility in water or oil; insensitivity of its surface activity to temperature, salinity, or other environmental factors; fast kinetics for their self-assembly; high biodegradability and biocompatibility; an excellent environmental profile; and a low 3 Biobased Surfactants Copyright © 2019 AOCS Press. https://doi.org/10.1016/B978-0-12-812705-6.00002-2 Published by Elsevier Inc. All rights reserved.
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