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Handbook of Chitin and Chitosan: Volume 3: Chitin- and Chitosan-based Polymer Materials for Various Applications Sabu Thomas (Editor)
Handbook of Chitin and Chitosan: Volume 2: Composites and Nanocomposites from Chitin and Chitosan, Manufacturing and Characterisations 1st Edition Sabu Thomas (Editor)
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Library of Congress Cataloging‐in‐Publication data applied for
Set in 10/12pt Times by SPi Global, Pondicherry, India
10 9 8 7 6 5 4 3 2 1
Yvonne Joseph, Teofil Jesionowski, and Hermann Ehrlich 2.1
2.3
2.4
2.3.1 Methods of Isolating Chitin from Glass Sponges (Hexactinellida)
2.3.2 Methods of Isolating Chitin from Demosponges (Demospongiae)
2.4.1
2.4.2
3 Physicochemical Properties of Chitosan and its Degradation Products
Karolina Gzyra‐Jagieła, Bozenna Peczek, Maria Wis niewska‐Wrona, and Natalia Gutowska
3.1
3.1.1
3.1.6
3.1.7
3.1.8
3.1.9
3.1.10
3.1.11
4 New Developments in the Analysis of Partially Acetylated Chitosan Polymers and Oligomers
Stefan Cord‐Landwehr, Anna Niehues, Jasper Wattjes, and Bruno M. Moerschbacher
4.1
4.2 Chitosan Oligomers
4.2.1 Degree of Polymerisation (DP), Fraction and Pattern of Acetylation (FA and PA)
4.3 Chitosan Polymers
4.3.1 Molecular Weight (MW) / Degree of Polymerisation (DP) and its Dispersity (ÐMW / ÐDP)
4.3.2 Fraction of Acetylation (FA) and its Dispersity (ÐFA)
4.3.3 Pattern of Acetylation (PA)
4.4
5
Zhengke Wang, Ling Yang, and Wen Fang
5.1 Introduction
5.2 Chitosan‐Based Multilayered Hydrogels
5.2.1 Periodic Precipitation
5.2.2 Alternating Process
5.2.3 Induced by Electrical Signals
5.2.4 Layer‐by‐Layer (LbL) Assembly
5.2.5 Sequential Curing
5.3 Chitin/Chitosan Physical Hydrogels Based on Alkali/Urea Solvent System
5.3.1 Chitin Hydrogels Based on Alkali/Urea Solvent System
5.3.2 Chitosan Hydrogels Based on Alkali/Urea Solvent System
5.4 Chitosan‐Based Injectable Hydrogels
5.4.1
5.4.2 Chemical Association
5.4.3 Double‐Network Hydrogels
5.5 Chitosan‐Based Self‐Healing Hydrogels
5.5.1
5.5.2
5.6 Chitosan‐Based Shape Memory Hydrogels
5.6.1 Water‐/Solvent‐Triggered
5.6.2
5.6.3
5.6.4
5.6.5
5.7 Superabsorbent Chitosan‐Based
5.7.1
5.7.2 Hydrogels by Graft Copolymerization
5.7.3
Liyou Dong, Harry J. Wichers, and Coen Govers
6.1
6.2
6.2.1
6.3
6.4
6.5
7 Antimicrobial Properties of Chitin and Chitosan
Magdalena Kucharska, Monika Sikora, Kinga Brzoza‐Malczewska, and Monika Owczarek
7.1 Microbiological Activity of Chitosan – The Mechanism of its Antibacterial and Antifungal Activity 169
7.2 The use of Chitin/Chitosan’s Microbiological Activity in Medicine and Pharmacy
7.3 Microbiological Activity of Chitosan in the Food Industry
7.4 Microbiological Activity of Chitosan in Paper and Textile Industries
7.5 Microbiological Activity of Chitosan in Agriculture
7.6 Outlook
8 Enzymes for Modification of Chitin and Chitosan
Gustav Vaaje‐Kolstad, Tina Rise Tuveng, Sophanit Mekasha, and Vincent G.H. Eijsink
8.1 CAZymes in Chitin Degradation and Modification
8.1.1 Chitinases
8.1.2 β‐N‐acetylhexosaminidases
8.1.3 Exo‐β‐glucosaminidases
8.1.4
8.1.5
8.1.6 Carbohydrate Esterases
8.1.7 Carbohydrate‐Binding Modules
8.2 Modular Diversity in Chitinases, Chitosanases and LPMOs
8.3 Biological Roles of Chitin‐Active Enzymes
8.4 Microbial Degradation and Utilisation of Chitin
8.4.1 Chitin Degradation by Serratia marcescens
8.4.2 Chitin Degradation by Bacteria in the Bacteroidetes Phylum
8.4.3 Chitin Degradation by Thermococcus Kodakarensis
8.4.4 Chitin Degradation by Fungi
8.5 Biotechnological Perspectives
8.6 Biorefining of Chitin‐Rich Biomass
8.7 Outlook
9 Chitin and Chitosan as Sources of Bio‐Based Building Blocks and Chemicals
Malgorzata Kaisler, Lambertus A.M. van den Broek, and Carmen G. Boeriu
9.1 Introduction
9.2 Chitin Conversion into Chitosan, Chitooligosaccharides and Monosaccharides
9.2.1 Chitosan Production
9.2.2 Production of Chitooligosaccharides
9.2.3 Production of GlcNAc and GlcN from Chitin
9.3 Building Blocks for Polymers from Chitin and its Derivatives
9.3.1 Furan‐Based Monomers
9.3.2 Amino Alcohol and Amino Acid Building Blocks
10 Chemical and Enzymatic Modification of Chitosan to Produce New Functional Materials with Improved Properties
Carmen G. Boeriu and Lambertus A.M. van den Broek
10.1 Introduction
10.2 Functional Chitosan Derivatives by Chemical and Enzymatic Modification
10.2.1 Anionic Chitosan Derivatives
10.2.2 Hydroxyalkylchitosans
10.2.3 Quaternised and Highly Cationic Chitosan Derivatives
10.2.4 Hydroxyaryl Chitosan Derivatives
Carbohydrate‐Modified Chitosan
10.3 Graft Co‐Polymers of Chitosan
10.4 Cross‐Linked Chitosan and Chitosan Polymer Networks
Cristian Peptu, Andra Cristina Humelnicu, Razvan Rotaru, Maria Emiliana Fortuna, Xenia Patras, Mirela Teodorescu, Bogdan Ionel Tamba, and Valeria Harabagiu
Interaction with Anionic Drugs
Efflux Pump Inhibitory Properties
Permeation‐Enhancing Properties
11.3 Chitosan—an Active Polymer for Bypassing Biological Barriers
Chitosan‐Based DDS Formulations
and Membranes
12 The Application of Chitin and its Derivatives for the Design of Advanced
Marcin H. Struszczyk, Longina Madej‐Kiełbik, and Dorota Zielińska
12.1 Selection of the Raw Sources: Safety Criteria
12.1.1 Aspect of Animal Tissue‐Originated Derivatives
12.1.2 General Requirements for Chitinous Biopolymers Applied in Designing Medical
12.1.3 Characterisation of the Biopolymer for Application in Wound Dressing Designing
12.1.4 Aspect of the Sterilization of the Final Wound Dressing
12.2 Types of Wound Dressings Consisting of Chitin‐Derived Biopolymers Available in the Market
12.3 Performance and Safety
12.4
13
Suse Botelho da Silva, Daiana de Souza, and Liziane Dantas
14.2.1
Chitosan‐Based
14.3 Specific Case of Chitosan Nanoparticles (CSNPs)
14.4 Applications to Sensitive
15 The Use of Chitosan‐Based Nanoformulations for Controlling Fungi During Storage of Horticultural Commodities
Silvia Bautista‐Baños, Zormy Nacary Correa‐Pacheco, and Rosa Isela Ventura‐Aguilar
15.1
15.2 Importance of Fruits and Vegetables
15.3
15.4 Plant Fungi Inhibition by Chitosan Application
15.5 Chitosan Integrated with Other Alternative Methods for Controlling Postharvest Fungi
15.6 Chitosan‐Based Formulations
15.7 Physiological Response and Quality Retention of Horticultural Commodities to Chitosan Coating Application
15.8 Influence of Chitosan Coatings on the Shelf Life of Horticultural Products
15.9 Effects of Chitosan Coatings with Additional Compounds on Quality and Microorganisms Development
15.10 Integration of Chitosan Nanoparticles into Coating Formulations and their Effects on the Quality of Horticultural Commodities and Development of Microorganisms
15.11 Outlook
16 Chitosan Application in Textile Processing and Fabric Coating
Thomas Hahn, Leonie Bossog, Tom Hager, Werner Wunderlich, Rudi Breier, Thomas Stegmaier, and Susanne Zibek
16.1 Chitosan in the Textile Industry
16.2 Textile Production
16.3 General Test Methods
16.4 Fibres and Yarns from Chitin and Chitosan
16.4.1 Chitin and Chitosan Solubilisation for Spinning Purposes
16.4.2
Sizing with Chitosan
16.5.1 Miscibility of Chitosan with Other Sizing Agents
16.5.2 Viscosity of Chitosan‐Containing Sizing Agents
16.5.3
16.5.4
Chitosan as a Finishing Agent or Coating
16.6.1 Chitosan as a Carrier and Linker
Suse Botelho da Silva, Guilherme Lopes Batista, and Cristiane Krause Santin
Nathalie Berezina and Antoine Hubert
19.4
19.6
19.4.2 Differences of Physical Assemblies of Chains and Molecules
Extraction and Purification Specificities of Chitins from Insects
List of Contributors
Artur Bartkowiak Center of Bioimmobilisation and Innovative Packaging Materials, Faculty of Food Sciences and Fisheries, West Pomeranian University of Technology, Szczecin, Poland
Leen Bastiaens VITO (Flemish Institute for Technological Research), Mol, Belgium
Silvia Bautista‐Baños Centro de Desarrollo de Productos Bióticos (CEPROBI), Instituto Politécnico Nacional (IPN), Yautepec, Morelos, Mexico
Nathalie Berezina Ynsect, Évry, France
Carmen G. Boeriu Wageningen Food & Biobased Research, Wageningen, The Netherlands
Leonie Bossog Textilchemie Dr. Petry GmbH, Reutlingen, Germany
Suse Botelho da Silva Food and Chemical Engineering, Polytechnic School, Unisinos University, São Leopoldo, RS, Brazil
Rudi Breier Textilchemie Dr. Petry GmbH, Reutlingen, Germany
Lambertus A.M. van den Broek Wageningen Food & Biobased Research, Wageningen, The Netherlands
Kinga Brzoza‐Malczewska Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Corneliu Cojocaru ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Véronique Coma University of Bordeaux, LCPO, UMR 5629, Centre National de la Recherche Scientifique (CNRS), Pessac, France
Stefan Cord‐Landwehr University of Münster, Institute for Biology and Biotechnology of Plants, Münster, Germany
Zormy Nacary Correa‐Pacheco CONACYT-CEPROBI, Instituto Politécnico Nacional, Yautepec, Morelos, Mexico
Els D’Hondt VITO (Flemish Institute for Technological Research), Mol, Belgium
Liyou Dong Food & Health Research, Wageningen Food & Biobased Research, Wageningen, The Netherlands; Food Chemistry, Wageningen University, Wageningen, The Netherlands
Hermann Ehrlich Institute of Electronics and Sensor Materials, TU Bergakademie‐Freiberg, Freiberg, Germany
Vincent G.H. Eijsink Faculty of Chemistry, Biotechnology, and Food Science, The Norwegian University of Life Sciences (NMBU), Ås, Norway
Kathy Elst VITO (Flemish Institute for Technological Research), Mol, Belgium
Wen Fang Institute of Biomedical Macromolecules, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China
Maria Emiliana Fortuna ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Coen Govers Food & Health Research, Wageningen Food & Biobased Research, Wageningen, The Netherlands
Natalia Gutowska Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Karolina Gzyra‐Jagieła Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Tom Hager German Institutes of Textile and Fiber Research, Denkendorf, Germany
Thomas Hahn Fraunhofer Institute of Interfacial Engineering and Biotechnology, Stuttgart, Germany
Valeria Harabagiu ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Antoine Hubert Ynsect, Évry, France
Andra Cristina Humelnicu ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Maria Ignat ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Teofil Jesionowski Institute of Chemical Technology and Engineering, Faculty of Chemical Technology, Poznan University of Technology, Poznan, Poland
Yvonne Joseph Institute of Electronics and Sensor Materials, TU Bergakademie‐Freiberg, Freiberg, Germany
Malgorzata Kaisler Bioprocess Engineering Group, Wageningen University, Wageningen, The Netherlands; Wageningen Food & Biobased Research, Wageningen, The Netherlands
Christine Klinger Institute of Physical Chemistry, TU Bergakademie‐Freiberg, Freiberg, Germany
Cristiane Krause Santin Food and Chemical Engineering, Polytechnic School, Unisinos University, São Leopoldo, RS, Brazil; itt CHIP – Unisinos Semiconductor Institute, São Leopoldo, RS, Brazil
Magdalena Kucharska Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Liziane Dantas Lacerda Food and Chemical Engineering, Polytechnic School, Unisinos University, São Leopoldo, RS, Brazil
Guilherme Lopes Batista itt CHIP – Unisinos Semiconductor Institute, São Leopoldo, RS, Brazil
Longina Madej‐Kiełbik The Institute of Security Technologies “MORATEX”, Lodz, Poland
Sophanit Mekasha Faculty of Chemistry, Biotechnology, and Food Science, The Norwegian University of Life Sciences (NMBU), Ås, Norway
Bruno M. Moerschbacher University of Münster, Institute for Biology and Biotechnology of Plants, Münster, Germany
Anna Niehues University of Münster, Institute for Biology and Biotechnology of Plants, Münster, Germany
Monika Owczarek Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Xenia Patras ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Boz enna Pe czek Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Cristian Peptu ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Iaroslav Petrenko Institute of Experimental Physics, TU Bergakademie‐Freiberg, Freiberg, Germany
Razvan Rotaru ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Petrisor Samoila ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Monika Sikora Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Lise Soetemans VITO (Flemish Institute for Technological Research), Mol, Belgium
Daiana de Souza Food and Chemical Engineering, Polytechnic School, Unisinos University, São Leopoldo, RS, Brazil
Thomas Stegmaier German Institutes of Textile and Fiber Research, Denkendorf, Germany
Marcin H. Struszczyk The Institute of Security Technologies “MORATEX”, Lodz, Poland
Bogdan Ionel Tamba A&B Pharm Corporation, Roman, Neamt , Romania
Mirela Teodorescu ‘Petru Poni’ Institute of Macromolecular Chemistry, Romanian Academy, Ias i, Romania
Tina Rise Tuveng Faculty of Chemistry, Biotechnology, and Food Science, The Norwegian University of Life Sciences (NMBU), Ås, Norway
Gustav Vaaje‐Kolstad Faculty of Chemistry, Biotechnology, and Food Science, The Norwegian University of Life Sciences (NMBU), Ås, Norway
Rosa Isela Ventura‐Aguilar CONACYT-CEPROBI, Instituto Politécnico Nacional, Yautepec, Morelos, Mexico
Zhengke Wang Institute of Biomedical Macromolecules, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China
Jasper Wattjes University of Münster, Institute for Biology and Biotechnology of Plants, Münster, Germany
Harry J. Wichers Food & Health Research, Wageningen Food & Biobased Research, Wageningen, The Netherlands; Food Chemistry, Wageningen University, Wageningen, The Netherlands
Maria Wis niewska‐Wrona Institute of Biopolymers and Chemical Fibres, Lodz, Poland
Werner Wunderlich German Institutes of Textile and Fiber Research, Denkendorf, Germany
Marcin Wysokowski Institute of Chemical Technology and Engineering, Faculty of Chemical Technology, Poznan University of Technology, Poznan, Poland; Institute of Electronics and Sensor Materials, TU Bergakademie‐Freiberg, Freiberg, Germany
Ling Yang Institute of Biomedical Macromolecules, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China
Susanne Zibek Fraunhofer Institute of Interfacial Engineering and Biotechnology, Stuttgart, Germany
Dorota Zielinska The Institute of Security Technologies “MORATEX”, Lodz, Poland
Sonia Z ółtowska Institute of Chemical Technology and Engineering, Faculty of Chemical Technology, Poznan University of Technology, Poznan, Poland; Institute of Electronics and Sensor Materials, TU Bergakademie‐Freiberg, Freiberg, Germany
Series Preface
Renewable resources, their use and modification are involved in a multitude of important processes with a major influence on our everyday lives. Applications can be found in the energy sector; paints and coatings; and the chemical, pharmaceutical, and textile industry, to name but a few.
The area interconnects several scientific disciplines (agriculture, biochemistry, chemistry, technology, environmental sciences, forestry), which makes it very difficult to have an expert view on the complicated interaction. Therefore, the idea to create a series of scientific books, focusing on specific topics concerning renewable resources, has been very opportune and can help to clarify some of the underlying connections in this area.
In a very fast‐changing world, trends are not only characteristic of fashion and political standpoints; science too is not free from hypes and buzzwords. The use of renewable resources is again more important nowadays; however, it is not part of a hype or a fashion. As the lively discussions among scientists continue about how many years we will still be able to use fossil fuels – opinions ranging from 50 to 500 years – they do agree that the reserve is limited, and that it is essential not only to search for new energy carriers but also for new material sources.
In this respect, the field of renewable resources is a crucial area in the search for alternatives for fossil‐based raw materials and energy. In the field of energy supply, biomass‐ and renewables‐based resources will be part of the solution alongside other alternatives such as solar energy, wind energy, hydraulic power, hydrogen technology and nuclear energy. In the field of material sciences, the impact of renewable resources will probably be even bigger. Integral utilisation of crops and the use of waste streams in certain industries will grow in importance, leading to a more sustainable way of producing materials. Although our society was much more (almost exclusively) based on renewable resources centuries ago, this disappeared in the Western world in the nineteenth century. Now it is time to focus again on this field of research. However, it should not mean a ‘retour à la nature’, but should be a multidisciplinary effort on a highly technological level to perform research towards new opportunities, to develop new crops and products from renewable resources. This will be essential to guarantee an acceptable level of comfort for the growing number of people living on our planet. It is ‘the’ challenge for the coming generations of scientists to develop more sustainable ways to create prosperity and to fight poverty and hunger in the world. A global approach is certainly favoured.
This challenge can only be dealt with if scientists are attracted to this area and are recognised for their efforts in this interdisciplinary field. It is, therefore, also essential that consumers recognise the fate of renewable resources in a number of products.
Furthermore, scientists do need to communicate and discuss the relevance of their work. The use and modification of renewable resources may not follow the path of the genetic engineering concept in view of consumer acceptance in Europe. Related to this aspect, the series will certainly help to increase the visibility of the importance of renewable resources. Being convinced of the value of the renewables approach for the industrial world, as well as for developing countries, I was myself delighted to collaborate on this series of books focusing on the different aspects of renewable resources. I hope that readers become aware of the complexity, the interaction and interconnections, and the challenges of this field, and that they will help to communicate on the importance of renewable resources.
I certainly want to thank the people of Wiley’s Chichester office, especially David Hughes, Jenny Cossham and Lyn Roberts, in seeing the need for such a series of books on renewable resources, for initiating and supporting it, and for helping to carry the project to the end.
Last, but not least, I want to thank my family, especially my wife Hilde and children Paulien and Pieter‐Jan, for their patience, and for giving me the time to work on the series when other activities seemed to be more inviting.
Christian V. Stevens,
Faculty of Bioscience Engineering
Ghent University, Belgium Series Editor, ‘Renewable Resources’ June 2005
Preface
Chitin was reported for the first time about 200 years ago, in extracts of mushrooms and insects. About 40 years later, chitosan was obtained from chitin by acid treatment. These polysaccharides are among the most abundant natural biopolymers in the world. They are, for example, present in crustaceans, insects and fungi. Just before World War II, there was a huge interest in the applications of these polysaccharides as a bioplastic. However, the simultaneous upcoming of synthetic polymers and the exponential increase in high‐performance synthetic polymers, which outperformed their natural counterparts, resulted in a decrease of interest in chitin/chitosan materials. In the 1970s, large‐scale production of chitin and chitosan from the shells of marine organisms started, owing to the development of aquaculture and the enactment of severe environmental regulations to decrease the amount of shellfish dumping in the oceans. Nowadays there is a need to be less dependent on fossil resources. The transition to a biobased economy and the increasing societal demand for more green and environmentally friendly products urge us to look for chemicals, materials and fuels based on renewable resources. The enormous potential of chitin and chitosan on account of their abundance, unique properties and numerous applications makes them interesting biomass resources. This book, Chitin and Chitosan: Properties and Applications, shows the state‐of‐the‐art and future perspectives of chitin and chitosan materials and applications. The book presents the most recent developments in the science and technology of all related fields, from extraction and characterisation to modification, material synthesis and end‐user applications. This book comprises 19 chapters that deal with most topics related to chitin and chitosan polymers and materials.
In Chapters 1–4, the sources of chitin and chitosan are described and how these biopolymers can be isolated. Next to the isolation, the analysis of the biopolymers is described. The different sources and/or isolation methods can result in different structures and properties. In Chapter 5–7, hydrogels, health effects and the anti‐microbial effects of chitin and chitosan are discussed. To improve or to modify the properties, enzymes and chemical reactions can be applied to customise these biopolymers, as shown in Chapters 8–10. The applications of chitin and chitosan in drug delivery, medical devices, agriculture, food, packaging, horticulture, textile, water purification and sensors are discussed in more detail in Chapters 11–18. And finally, Chapter 19 is devoted to the market and regulation of chitin and chitosan.
These topics have never been addressed previously in a single book. Books, book chapters and reviews have been dedicated to the specific fields of application of chitin and chitosan materials. This book presents an overview of the latest scientific and technological advances in almost all areas of application, and show the great potential of chitin and chitosan as materials of the future. We hope that the reader will be inspired by the examples given of these biopolymers in different areas. We are confident that chitin and chitosan will become major renewable resources in the biobased circular economy.
This book should be useful for scholars and those in academia, such as undergraduate and postgraduate students in the areas of agriculture, polymer and material sciences, biobased economy and life sciences. In addition, we hope this book will aid researchers and specialists from industry in the field of (bio)polymers, packaging, biomedical applications, water treatment, textiles, sensors, and agriculture and food – as well as regional and national policy‐makers.
The input is from well‐known experts from all over the world. We would like to express our great gratitude to all chapter authors of this book, who have made excellent contributions. In addition, we would like to thank Sarah Higginbotham, Emma Strickland and Lesley Jebaraj from Wiley for all their help.
Lambertus A.M. van den Broek and Carmen G. Boeriu Wageningen 2019
1Sources of Chitin and Chitosan and their Isolation
Leen Bastiaens, Lise Soetemans, Els D’Hondt, and Kathy Elst
VITO – (Flemish
Institute for Technological Research), Mol, Belgium
Chitin is a natural biomolecule that was reported for the first time in 1811 by the French professor Henri Braconnot as fungine [1] and in 1823 by Antoine Odier as chitin. Chitin consists of large, crystalline nitrogen‐containing polysaccharides made of chains of a modified glucose monosaccharide, being N‐acetylglucosamine. It is ubiquitously present in the world and has even been reported to be one of the most abundant biomolecules on earth, with an estimated annual production of 1011–1014 tons [2, 3]. Chitin serves as template for biomineralization such as calcification and silicification, providing preferential sites for nucleation, and controlling the location and orientation of mineral phases [4, 5]. This phenomenon explains the presence of chitin in solid structures in a variety of biomass such as cell walls of fungi and diatoms and in exoskeletons of Crustaceans. Chitin is present in diverse structures in at least 19 animal phyla besides its presence in bacteria, fungi, and algae [5].
Chitosan is mainly known as a partially deacetylated derivative of chitin that is more water soluble than chitin, and as such is easier to process. For this reason, chitosan—and, in some cases, even more preferably, the relatively small sized (1–10 kDa) chitosan oligomers—are the molecules that are envisioned for multiple applications such as agriculture; water and wastewater treatment; food and beverages; chemicals; feed; cosmetics; and personal care [6, 7]. In addition, chitosan oligomers have been reported as being bioactive [8], offering potential for application in, for instance, wound dressing and cosmetics. Although chitin and chitosan are versatile and promising biomaterials [9], the extraction
Chitin and Chitosan: Properties and Applications, First Edition. Edited by Lambertus A.M. van den Broek and Carmen G. Boeriu.
and purification of chitin and its conversion to chitosan (oligomers) require several process steps, and these have been mentioned as bottlenecks that hinder the wider use of the underspent chitin in the world.
This chapter intends to provide more information related to (1) the structure of chitin, (2) sources of chitin and chitosan, and (3) their extraction and purification, as well as (4) the conversion of chitin into chitosan. The further conversion of chitosan to chitosan oligomers is the subject of Chapter 3.
1.1 Chitin and Chitosan
1.1.1
Chemical Structure
Chitin, and its derivate chitosan, are natural polysaccharides consisting of 2 monosaccharides, N‐acetyl‐D‐glucosamine and D‐glucosamine, connected by β‐1,4‐ glycoside bonds. Depending on the frequency of the latter monosaccharides, the molecule is defined as chitin or chitosan. Chitin contains mainly N‐acetyl‐D‐glucosamine and can be transformed to chitosan by partial deacetylation of the monomer N‐acetyl‐D‐glucosamine to D‐glucosamine (see Figure 1.1) [7]. Diverse definitions of chitin and chitosan circulate in literature. Most sources mention a deacetylation degree of at least 50% [7, 10] as a criterion to define the molecule as chitosan. Others report a deacetylation degree of at least 60% or 75% for chitosan, implying that, respectively, more than 60% or 75% of the monosaccharides are D‐glucosamine moieties [11–13]. Chitin in its natural appearance is usually already a heteropolymer, with a deacetylation degree ranging between 5% and 20% [14]. The structure of chitin is very similar to that of cellulose and shares generally the same function of providing structure integrity and protection of the organism.
1.1.2 Different Crystalline Forms of Chitin
Chitin usually functions as a supporting material and is composed of layers of polysaccharide sheets. Each individual sheet consists of multiple parallel‐positioned chitin chains [17], as schematically presented in Figure 1.2. Highly crystalline fibers are formed when the polymer sheets are placed next to each other and form interactions [12]. Depending on their orientation, three crystalline forms have been reported (α, β, and γ).
The most abundant form is α‐chitin, which is present in almost all crustaceans, insects, fungi, and yeast cell walls [7]. In this formation, the chitin sheets (three sheets as example in Figure 1.2a), consisting of parallel chitin chains (for each sheet, two chains are presented in Figure 1.2a), are positioned in an anti‐parallel way, allowing a maximum formation of hydrogen bonding. More specifically, two intramolecular and two intermolecular bondings are formed: a first intermolecular bonding with a vertical neighbor chain (in the same sheet), and another with a horizontal neighbor chain form a different sheet [15]. These hydrogen bounds create a remarkably high crystallinity, resulting in a more stiff and stable material. Therefore, α‐chitin is characterized as a non‐reactive and insoluble product [16]. Since this form is the most common polymorphic, α‐chitin has been extensively studied [12].
On the other hand, in β‐chitin, the chitin sheets are ordered in parallel (Figure 1.2b) with weaker intermolecular forces. This results in a softer molecule with a higher affinity
Fungi
Mollusks
Chitin
Algae
Chitosan
Crustaceans
Insects
Figure 1.1 Chemical structure of chitin and chitosan and some examples of species that contain chitin.
1.2 Schematic representation of (a) α‐form and (b) β‐form of chitin.
