Chitosan: A Natural Biopolymer with a Wide and Varied Range of Applications

Abstract

Although chitin is of the most available biopolymers on Earth its uses and applications are limited due to its low solubility. The deacetylation of chitin leads to chitosan. This biopolymer, composed of randomly distributed β-(1-4)-linked D-units, has better physicochemical properties due to the facts that it is possible to dissolve this biopolymer under acidic conditions, it can adopt several conformations or structures and it can be functionalized with a wide range of functional groups to modulate its superficial composition to a specific application. Chitosan is considered a highly biocompatible biopolymer due to its biodegradability, bioadhesivity and bioactivity in such a way this biopolymer displays a wide range of applications. Thus, chitosan is a promising biopolymer for numerous applications in the biomedical field (skin, bone, tissue engineering, artificial kidneys, nerves, livers, wound healing). This biopolymer is also employed to trap both organic compounds and dyes or for the selective separation of binary mixtures. In addition, chitosan can also be used as catalyst or can be used as starting molecule to obtain high added value products. Considering these premises, this review is focused on the structure and modification of chitosan as well as its uses and applications.

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98. 98.

    Stolnik S., Illum L., Davis S.S. Long circulating microparticulate drug carriers. Adv. Drug Deliv. Rev. 2012;64:290-301.

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99. 99.

    Kim S.-K. Chitin, Chitosan, Oligosaccharides and Their Derivatives: Biological Activie and Applications. 2010.

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100. 100.

     Mathew M.E., Mohan J.C., Manzoor K., Nair S.V., Tamura H., Jayakumar R. Folate conjugated carboxymethyl chitosan-manganese doped zinc sulphide nanoparticles for targeted drug delivery and imaging of cancer cells. Carbohydr. Polym. 2010;80:442-448.

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101. 101.

     Hasegawa M., Yagi K., Iwakawa S., Hirai M. Chitosan induces apoptosis via caspase-3 activation in bladder tumor cells. Jpn. J. Cancer Res. 2001;92:459-466.

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102. 102.

     Chen W.R., Adams R.L., Carubelli R., Nordquist R.E. Laser-photosensitizer assisted immunotherapy: A novel modality for cancer treatment. Cancer Lett. 1997;115:25-30.

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103. 103.

     Nishimura I.C., Nishimura S., Nishi N., Saiki I., Tokura S., Azuma I. Immunological Activity of Chitin. Vaccine. 1984;2:93-99.

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104. 104.

     Qi L., Xu Z., Chen M. In vitro and in vivo suppression of hepatocellular carcinoma growth by chitosan nanoparticles. Eur. J. Cancer. 2007;43:184-193.

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105. 105.

     Gumińska M., Ignacak J., Wojcik E. In vitro inhibitory effect of chitosan and its degradation products on energy metabolism in Ehrlich ascites tumour cells (EAT). Polish J. Pharmacol. 1996;48:495-501.

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106. 106.

     Singh D.K., Ray A.R. Biomedical applications of chitin, chitosan, and their derivatives. J. Macromol. Sci. Polym. Rev. 2000;40:69-83.

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     Blair H.S., Guthrie J., Law T.-K., Turkington P. Chitosan and modified chitosan membranes I. Preparation and characterisation. J. Appl. Polym. Sci. 1987;33:641-656.

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108. 108.

     Kubota N., Kikuchi Y., Mizuhara Y., Ishihara T., Takita Y. Solid-phase modification of chitosan hydrogel membranes and permeability properties of modified chitosan membranes. J. Appl. Polym. Sci. 1993;50:1665-1670.

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109. 109.

     Hirano S., Tobetto K., Hasegawa M., Matsuda N. Permeability properties of gels and membranes derived from chitosan. J. Biomed. Mater. Res. 1980;14:477-485.

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     Xue L., Greisler H.P. Biomaterials in the development and future of vascular grafts. J. Vasc. Surg. 2003;37:472-480.

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111. 111.

     Chupa J.M., Foster A.M., Sumner S.R., Madihally S.V., Matthew H.W. Vascular cell responses to polysaccharide materials. Biomaterials. 2000;21:2315-2322.

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112. 112.

     Madihally S.V., Matthew H.W.T. Porous chitosan scaffolds for tissue engineering. Biomaterials. 1999;20:1133-1142.

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113. 113.

     Irvine S.A., Yun X., Venkatraman S. Anti-platelet and tissue engineering approaches to biomaterial blood compatibilization: How well have these been translated into the clinic? Drug Deliv. Transl. Res. 2012;2:384-397.

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114. 114.

     Chiellini E., Giusti P. Heparine-Like Substance and Blood Compatible Polymers Obtained from Chitin and Chitosan. 1983.

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115. 115.

     Hudson S.M., Jenkins D.W. Chitin and Chitosan. 2002.

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116. 116.

     Mark H.F., Kroschwitz J.I. Encyclopedia of Polymer Science and Engineering. 1989.

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117. 117.

     Gooday G.W. Advances in Microbial Ecology. 1990.

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118. 118.

     Schisler D.A., Slininger P.J., Behle R.W., Jackson M.A. Formulation of Bacillus spp. for biological control of plant diseases. Phytopathology. 2004;94:1267-1271.

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119. 119.

     Kumar M.N.V.R. A review of chitin and chitosan applications. React. Funct. Polym. 2000;46:1-27.

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120. 120.

     Shahidi F., Arachchi J.K.V., Jeon Y.J. Food applications of chitin and chitosans. Trends Food Sci. Technol. 1999;10:37-51.

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121. 121.

     Goy R.C., De Britto D., Assis O.B.G. A review of the antimicrobial activity of chitosan. Polimeros. 2009;19:241-247.

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122. 122.

     Sahariah P., Másson M. Antimicrobial Chitosan and Chitosan Derivatives: A Review of the Structure-Activity Relationship. Biomacromolecules. 2017;18:3846-3868.

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123. 123.

     Dutta P.K., Tripathi S., Mehrotra G.K., Dutta J. Perspectives for chitosan based antimicrobial films in food applications. Food Chem. 2009;114:1173-1182.

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124. 124.

     Geisberger G., Gyenge E.B., Hinger D., Käch A., Maake C., Patzke G.R. Chitosan-thioglycolic acid as a versatile antimicrobial agent. Biomacromolecules. 2013;14:1010-1017.

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125. 125.

     Kaya M., Cakmak Y.S., Baran T., Asan-Ozusaglam M., Mentes A., Tozak K.O. New chitin, chitosan, and O-carboxymethyl chitosan sources from resting eggs of Daphnia longispina (Crustacea); with physicochemical characterization, and antimicrobial and antioxidant activities. Biotechnol. Bioprocess Eng. 2014;19:58-69.

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126. 126.

     Hu L., Meng X., Xing R., Liu S., Chen X., Qin Y., Yu H., Li P. Design, synthesis and antimicrobial activity of 6-N-substituted chitosan derivatives. Bioorgan. Med. Chem. Lett. 2016;26:4548-4551.

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127. 127.

     Sano H., Shibasaki K.I., Matsukubo T., Takaesu Y. Effect of chitosan rinsing on reduction of dental plaque formation. Bull. Tokyo Dent. Coll. 2003;44:9-16.

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128. 128.

     Coma V., Deschamps A., Martial-Gros A. Bioactive Packaging Materials from Edible Chitosan Polymer—Antimicrobial Activity Assessment on Dairy-Related Contaminants. J. Food Sci. 2003;68:2788-2792.

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129. 129.

     Badawy M.E.I., Rabea E.I. A Biopolymer Chitosan and Its Derivatives as Promising Antimicrobial Agents against Plant Pathogens and Their Applications in Crop Protection. Int. J. Carbohydr. Chem. 2011;2011:1-29.

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130. 130.

     Ong S.Y., Wu J., Moochhala S.M., Tan M.H., Lu J. Development of a chitosan-based wound dressing with improved hemostatic and antimicrobial properties. Biomaterials. 2008;29:4323-4332.

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131. 131.

     Dai T., Tanaka M., Huang Y.Y., Hamblin M.R. Chitosan preparations for wounds and burns: Antimicrobial and wound-healing effects. Expert Rev. Anti. Infect. Ther. 2011;9:857-879.

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132. 132.

     Xiao Z., Luo Y., Luo Y., Wang Q. Combined effects of sodium chlorite dip treatment and chitosan coatings on the quality of fresh-cut d’Anjou pears. Postharvest Biol. Technol. 2011;62:319-326.

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133. 133.

     Dragostin O.M., Samal S.K., Dash M., Lupascu F., Pânzariu A., Tuchilus C., Ghetu N., Danciu M., Dubruel P., Pieptu D., et al. New antimicrobial chitosan derivatives for wound dressing applications. Carbohydr. Polym. 2016;141:28-40.

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134. 134.

     Dragostin O.M., Sama S.K., Lupascu F., Pânzariu A., Dubruel P., Lupascu D., Tuchilus C., Vasile C., Profire L. Development and characterization of novel films based on sulfonamide-chitosan derivatives for potential wound dressing. Int. J. Mol. Sci. 2015;16:29843-29855.

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135. 135.

     Stawski D., Sahariah P., Hjálmarsdóttir M., Wojciechowska D., Puchalski M., Másson M. N,N,N-trimethyl chitosan as an efficient antibacterial agent for polypropylene and polylactide nonwovens. J. Text. Inst. 2017;108:1041-1049.

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136. 136.

     Yang Z., Peng H., Wang W., Liu T. Crystallization behavior of poly(ε-caprolactone)/layered double hydroxide nanocomposites. J. Appl. Polym. Sci. 2010;116:2658-2667.

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137. 137.

     Sang W., Tang Z., He M.Y., Hua Y.P., Xu Q. Preparation, characterization and application of the novel chitosan derivative modified with phenylalanine. Fibers Polym. 2015;16:991-996.

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138. 138.

     Ignatova M., Manolova N., Markova N., Rashkov I. Electrospun non-woven nanofibrous hybrid mats based on chitosan and PLA for wound-dressing applications. Macromol. Biosci. 2009;9:102-111.

     Not in our library10.1002/mabi.200800189

139. 139.

     Ji Q.X., Zhong D.Y., Lü R., Zhang W.Q., Deng J., Chen X.G. In vitro evaluation of the biomedical properties of chitosan and quaternized chitosan for dental applications. Carbohydr. Res. 2009;344:1297-1302.

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140. 140.

     Sano H., Shibasaki K., Matsukubo T., Takaesu Y. Comparison of the activity of four chitosan derivatives in reducing initial adherence of oral bacteria onto tooth surfaces. Bull. Tokyo Dent. Coll. 2001;42:243-249.

     Not in our library10.2209/tdcpublication.42.243

141. 141.

     Nechita P., Bobu E., Parfene G., Dinicə R.M., Bəlan T. Antimicrobial coatings based on chitosan derivatives and quaternary ammonium salts for packaging paper applications. Cellul. Chem. Technol. 2015;49:625-632.

     Not in our library

142. 142.

     Gupta D., Haile A. Multifunctional properties of cotton fabric treated with chitosan and carboxymethyl chitosan. Carbohydr. Polym. 2007;69:164-171.

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143. 143.

     Ye W., Leung M.F., Xin J., Kwong T.L., Lee D.K.L., Li P. Novel core-shell particles with poly(n-butyl acrylate) cores and chitosan shells as an antibacterial coating for textiles. Polymer (Guildf). 2005;46:10538-10543.

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144. 144.

     Nigmatullin R., Konovalova V., Pobigay G. Development of Antimicrobial Membranes via the Surface Tethering of Chitosan. J. Appl. Polym. Sci. 2009;111:1697-1705.

     Not in our library10.1002/app.29135

145. 145.

     Xu X., Zhuang X., Cheng B., Xu J., Long G., Zhang H. Manufacture and properties of cellulose/O-hydroxyethyl chitosan blend fibers. Carbohydr. Polym. 2010;81:541-544.

     Not in our library10.1016/j.carbpol.2010.03.011

146. 146.

     Inta O., Yoksan R., Limtrakul J. Hydrophobically modified chitosan: A bio-based material for antimicrobial active film. Mater. Sci. Eng. C. 2014;42:569-577.

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147. 147.

     Sridhari T.R., Dutta P.K. Synthesis and characterization of maleilated chitosan for dye house effluent. Indian J. Chem. Technol. 2000;7:198-201.

     Not in our library

148. 148.

     El Mouzdahir Y., Elmchaouri A., Mahboub R., Gil A., Korili S.A. Equilibrium modeling for the adsorption of methylene blue from aqueous solutions on activated clay minerals. Desalination. 2010;250:335-338.

     Not in our library10.1016/j.desal.2009.09.052

149. 149.

     Chang M.Y., Juang R.S. Adsorption of tannic acid, humic acid, and dyes from water using the composite of chitosan and activated clay. J. Colloid Interface Sci. 2004;278:18-25.

     Not in our library10.1016/j.jcis.2004.05.029

150. 150.

     Wan Ngah W.S., Ariff N.F.M., Hanafiah M.A.K.M. Preparation, characterization, and environmental application of crosslinked chitosan-coated bentonite for tartrazine adsorption from aqueous solutions. Water. Air. Soil Pollut. 2010;206:225-236.

     Not in our library10.1007/s11270-009-0098-5

151. 151.

     Ngah W.S.W., Ariff N.F.M., Hashim A., Hanafiah M.A.K.M. Malachite green adsorption onto chitosan coated bentonite beads: Isotherms, kinetics and mechanism. Clean Soil Air Water. 2010;38:394-400.

     Not in our library10.1002/clen.200900251

152. 152.

     Zhu H.Y., Jiang R., Xiao L. Adsorption of an anionic azo dye by chitosan/kaolin/γ-Fe2O3 composites. Appl. Clay Sci. 2010;48:522-526.

     Not in our library10.1016/j.clay.2010.02.003

153. 153.

     Wang L., Wang A. Adsorption characteristics of Congo Red onto the chitosan/montmorillonite nanocomposite. J. Hazard. Mater. 2007;147:979-985.

     Not in our library10.1016/j.jhazmat.2007.01.145

154. 154.

     Hasan M., Ahmad A.L., Hameed B.H. Adsorption of reactive dye onto cross-linked chitosan/oil palm ash composite beads. Chem. Eng. J. 2008;136:164-172.

     Not in our library10.1016/j.cej.2007.03.038

155. 155.

     Lee H.C., Jeong Y.G., Min B.G., Lyoo W.S., Lee S.C. Preparation and acid dye adsorption behavior of polyurethane/chitosan composite foams. Fibers Polym. 2009;10:636-642.

     Not in our library10.1007/s12221-010-0636-1

156. 156.

     Ahmad A.L., Sumathi S., Hameed B.H. Chitosan: A natural biopolymer for the adsorption of residue oil from oily wastewater. Adsorpt. Sci. Technol. 2004;22:75-88.

     Not in our library10.1260/026361704323151015

157. 157.

     Yang T., Zall R.R. Chitosan Membranes for Reverse Osmosis Application. J. Food Sci. 1984;49:91-93.

     Not in our library10.1111/j.1365-2621.1984.tb13677.x

158. 158.

     Wan Ngah W.S., Teong L.C., Hanafiah M.A.K.M. Adsorption of dyes and heavy metal ions by chitosan composites: A review. Carbohydr. Polym. 2011;83:1446-1456.

     Not in our library10.1016/j.carbpol.2010.11.004

159. 159.

     Monier M. Adsorption of Hg2+, Cu2+ and Zn2+ ions from aqueous solution using formaldehyde cross-linked modified chitosan-thioglyceraldehyde Schiff’s base. Int. J. Biol. Macromol. 2012;50:773-781.

     Not in our library10.1016/j.ijbiomac.2011.11.026

160. 160.

     Lü H., An H., Xie Z. Ion-imprinted carboxymethyl chitosan-silica hybrid sorbent for extraction of cadmium from water samples. Int. J. Biol. Macromol. 2013;56:89-93.

     Not in our library10.1016/j.ijbiomac.2013.02.003

161. 161.

     Ngah W.S.W., Fatinathan S. Adsorption of Cu(II) ions in aqueous solution using chitosan beads, chitosan-GLA beads and chitosan-alginate beads. Chem. Eng. J. 2008;143:62-72.

     Not in our library10.1016/j.cej.2007.12.006

162. 162.

     Vijaya Y., Popuri S.R., Boddu V.M., Krishnaiah A. Modified chitosan and calcium alginate biopolymer sorbents for removal of nickel (II) through adsorption. Carbohydr. Polym. 2008;72:261-271.

     Not in our library10.1016/j.carbpol.2007.08.010

163. 163.

     Qiao Z., Wang Z., Zhang C., Yuan S., Zhu Y., Wang J. PVAm–PIP/PS composite membrane with high performance for CO2/N2 separation. AIChE J. 2012;59:215-228.

     Not in our library10.1002/aic.13781

164. 164.

     Boddu V.M., Abburi K., Talbott J.L., Smith E.D., Haasch R. Removal of arsenic (III) and arsenic (V) from aqueous medium using chitosan-coated biosorbent. Water Res. 2008;42:633-642.

     Not in our library10.1016/j.watres.2007.08.014

165. 165.

     Boddu V.M., Abburi K., Randolph A.J., Smith E.D. Removal of copper (II) and nickel (II) ions from aqueous solutions by a composite chitosan biosorbent. Sep. Sci. Technol. 2008;43:1365-1381.

     Not in our library10.1080/01496390801940762

166. 166.

     Boddu V.M., Abburi K., Talbott J.L., Smith E.D. Removal of hexavalent chromium from wastewater using a new composite chitosan biosorbent. Environ. Sci. Technol. 2003;37:4449-4456.

     Not in our library10.1021/es021013a

167. 167.

     Dragan E.S., Dinu M.V., Timpu D. Preparation and characterization of novel composites based on chitosan and clinoptilolite with enhanced adsorption properties for Cu2+. Bioresour. Technol. 2010;101:812-817.

     Not in our library10.1016/j.biortech.2009.08.077

168. 168.

     Dinu M.V., Dragan E.S. Evaluation of Cu2+, Co2+ and Ni2+ ions removal from aqueous solution using a novel chitosan/clinoptilolite composite: Kinetics and isotherms. Chem. Eng. J. 2010;160:157-163.

     Not in our library10.1016/j.cej.2010.03.029

169. 169.

     Qu R., Sun C., Ma F., Zhang Y., Ji C., Xu Q., Wang C., Chen H. Removal and recovery of Hg(II) from aqueous solution using chitosan-coated cotton fibers. J. Hazard. Mater. 2009;167:717-727.

     Not in our library10.1016/j.jhazmat.2009.01.043

170. 170.

     Qu R., Sun C., Wang M., Ji C., Xu Q., Zhang Y., Wang C., Chen H., Yin P. Adsorption of Au(III) from aqueous solution using cotton fiber/chitosan composite adsorbents. Hydrometallurgy. 2009;100:65-71.

     Not in our library10.1016/j.hydromet.2009.10.008

171. 171.

     Zhang G., Qu R., Sun C., Ji C., Chen H., Wang C., Niu Y. Adsorption for Metal Ions of Chitosan Coated Cotton Fiber. J. Appl. Polym. Sci. 2008;110:2321-2327.

     Not in our library10.1002/app.27515

172. 172.

     Huang G., Zhang H., Shi J.X., Langrish T.A.G. Adsorption of chromium(VI) from aqueous solutions using cross-linked magnetic chitosan beads. Ind. Eng. Chem. Res. 2009;48:2646-2651.

     Not in our library10.1021/ie800814h

173. 173.

     Tran H.V., Tran L.D., Nguyen T.N. Preparation of chitosan/magnetite composite beads and their application for removal of Pb(II) and Ni(II) from aqueous solution. Mater. Sci. Eng. C. 2010;30:304-310.

     Not in our library10.1016/j.msec.2009.11.008

174. 174.

     Kalyani S., Priya J.A., Rao P.S., Krishnaiah A. Removal of copper and nickel from aqueous solutions using chitosan coated on perlite as biosorbent. Sep. Sci. Technol. 2005;40:1483-1495.

     Not in our library10.1081/ss-200055940

175. 175.

     Hasan S., Krishnaiah A., Ghosh T.K., Viswanath D.S., Boddu V.M., Smith E.D. Adsorption of divalent cadmium (Cd(II)) from aqueous solutions onto chitosan-coated perlite beads. Ind. Eng. Chem. Res. 2006;45:5066-5077.

     Not in our library10.1021/ie0402620

176. 176.

     Hasan S., Krishnaiah A., Ghosh T.K., Viswanath D.S., Boddu V.M., Smith E.D. Adsorption of chromium(VI) on chitosan-coated perlite. Sep. Sci. Technol. 2003;38:3775-3793.

     Not in our library10.1081/ss-120024229

177. 177.

     Hasan S., Ghosh T.K., Viswanath D.S., Boddu V.M. Dispersion of chitosan on perlite for enhancement of copper(II) adsorption capacity. J. Hazard. Mater. 2008;152:826-837.

     Not in our library10.1016/j.jhazmat.2007.07.078

178. 178.

     Kumar M., Tripathi B.P., Shahi V.K. Crosslinked chitosan/polyvinyl alcohol blend beads for removal and recovery of Cd(II) from wastewater. J. Hazard. Mater. 2009;172:1041-1048.

     Not in our library10.1016/j.jhazmat.2009.07.108

179. 179.

     Wan Ngah W.S., Kamari A., Koay Y.J. Equilibrium and kinetics studies of adsorption of copper (II) on chitosan and chitosan/PVA beads. Int. J. Biol. Macromol. 2004;34:155-161.

     Not in our library10.1016/j.ijbiomac.2004.03.001

180. 180.

     Popuri S.R., Vijaya Y., Boddu V.M., Abburi K. Adsorptive removal of copper and nickel ions from water using chitosan coated PVC beads. Bioresour. Technol. 2009;100:194-199.

     Not in our library10.1016/j.biortech.2008.05.041

181. 181.

     Jiang Z., Yu Y., Wu H. Preparation of CS/GPTMS hybrid molecularly imprinted membrane for efficient chiral resolution of phenylalanine isomers. J. Membr. Sci. 2006;280:876-882.

     Not in our library10.1016/j.memsci.2006.03.006

182. 182.

     Jiraratananon R., Chanachai A., Huang R.Y.M., Uttapap D. Pervaporation dehydration of ethanol-water mixtures with chitosan/hydroxyethylcellulose (CS/HEC) composite membranes I. Effect of operating conditions. J. Membr. Sci. 2002;195:143-151.

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183. 183.

     Mochizuki A., Amiya S., Sato Y., Ogawara H., Yamashita S. Pervaporation separation of water/ethanol mixtures through polysaccharide membranes. III. The Permselectivity of the Neutralized Chitosan Membrane and the Relationships between Its Permselectivity and Solid State Structure. J. Appl. Polym. Sci. 1989;37:3385-3398.

     Not in our library10.1002/app.1989.070371210

184. 184.

     Goto M., Shiosaki A., Hirose T. Separation of Water/Ethanol Vapor Mixtures through Chitosan and Crosslinked Chitosan Membranes. Sep. Sci. Technol. 1994;29:1915-1923.

     Not in our library10.1080/01496399408002180

185. 185.

     Shieh J.J., Huang R.Y.M. Preparation of N-methylol nylon-6 membranes for pervaporation of ethanol-water mixtures. J. Appl. Polym. Sci. 1997;64:855-863.

     Not in our library10.1002/(sici)1097-4628(19970502)64:5<855::aid-app5>3.0.co;2-o

186. 186.

     Chen X., Yang H., Gu Z., Shao Z. Preparation and characterization of HY zeolite-filled chitosan membranes for pervaporation separation. J. Appl. Polym. Sci. 2001;79:1144-1149.

     Not in our library10.1002/1097-4628(20010207)79:6<1144::aid-app190>3.0.co;2-d

187. 187.

     Uragami T., Tanaka Y., Nishida S. Permeation and separation under high temperature and high pressure for ethanol/water vapors through cross-linked quaternized chitosan composite membranes. Desalination. 2002;147:449-454.

     Not in our library10.1016/s0011-9164(02)00642-2

188. 188.

     Nawawi M.G.M., Huang R.Y.M. Pervaporation dehydration of isopropanol with chitosan membranes. J. Membr. Sci. 1997;124:53-62.

     Not in our library

189. 189.

     Chanachai A., Jiraratananon R., Uttapap D., Moon G.Y., Anderson W.A., Huang R.Y.M. Pervaporation with chitosan/hydroxyethylcellulose (CS/HEC) blended membranes. J. Membr. Sci. 2000;166:271-280.

     Not in our library10.1016/s0376-7388(99)00269-0

190. 190.

     Devi D.A., Smitha B., Sridhar S., Aminabhavi T.M. Pervaporation separation of isopropanol/water mixtures through crosslinked chitosan membranes. J. Membr. Sci. 2005;262:91-99.

     Not in our library10.1016/j.memsci.2005.03.051

191. 191.

     Kittur A.A., Kulkarni S.S., Aralaguppi M.I., Kariduraganavar M.Y. Preparation and characterization of novel pervaporation membranes for the separation of water-isopropanol mixtures using chitosan and NaY zeolite. J. Membr. Sci. 2005;247:75-86.

     Not in our library10.1016/j.memsci.2004.09.010

192. 192.

     Svang-Ariyaskul A., Huang R.Y.M., Douglas P.L., Pal R., Feng X., Chen P., Liu L. Blended chitosan and polyvinyl alcohol membranes for the pervaporation dehydration of isopropanol. J. Membr. Sci. 2006;280:815-823.

     Not in our library10.1016/j.memsci.2006.03.001

193. 193.

     Liu Y.L., Yu C.H., Lee K.R., Lai J.Y. Chitosan/poly(tetrafluoroethylene) composite membranes using in pervaporation dehydration processes. J. Membr. Sci. 2007;287:230-236.

     Not in our library10.1016/j.memsci.2006.10.040

194. 194.

     Chen J.H., Liu Q.L., Fang J., Zhu A.M., Zhang Q.G. Composite hybrid membrane of chitosan-silica in pervaporation separation of MeOH/DMC mixtures. J. Colloid Interface Sci. 2007;316:580-588.

     Not in our library10.1016/j.jcis.2007.09.022

195. 195.

     Choudhari S.K., Kittur A.A., Kulkarni S.S., Kariduraganavar M.Y. Development of novel blocked diisocyanate crosslinked chitosan membranes for pervaporation separation of water-isopropanol mixtures. J. Membr. Sci. 2007;302:197-206.

     Not in our library10.1016/j.memsci.2007.06.045

196. 196.

     Tsai H.A., Chen W.H., Kuo C.Y., Lee K.R., Lai J.Y. Study on the pervaporation performance and long-term stability of aqueous iso-propanol solution through chitosan/polyacrylonitrile hollow fiber membrane. J. Membr. Sci. 2008;309:146-155.

     Not in our library10.1016/j.memsci.2007.10.018

197. 197.

     Rachipudi P.S., Kittur A.A., Choudhari S.K., Varghese J.G., Kariduraganavar M.Y. Development of polyelectrolyte complexes of chitosan and phosphotungstic acid as pervaporation membranes for dehydration of isopropanol. Eur. Polym. J. 2009;45:3116-3126.

     Not in our library10.1016/j.eurpolymj.2009.08.011

198. 198.

     Varghese J.G., Kittur A.A., Rachipudi P.S., Kariduraganavar M.Y. Synthesis, characterization and pervaporation performance of chitosan-g-polyaniline membranes for the dehydration of isopropanol. J. Membr. Sci. 2010;364:111-121.

     Not in our library10.1016/j.memsci.2010.08.007

199. 199.

     Sajjan A.M., Jeevan Kumar B.K., Kittur A.A., Kariduraganavar M.Y. Novel approach for the development of pervaporation membranes using sodium alginate and chitosan-wrapped multiwalled carbon nanotubes for the dehydration of isopropanol. J. Membr. Sci. 2013;425–426:77-88.

     Not in our library10.1016/j.memsci.2012.08.042

200. 200.

     Yong Nam S., Moo Lee Y. Pervaporation of ethylene glycol-water mixtures. I. Pervaporation performance of surface crosslinked chitosan membranes. J. Membr. Sci. 1999;153:155-162.

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201. 201.

     Hu C., Guo R., Li B., Ma X., Wu H., Jiang Z. Development of novel mordenite-filled chitosan-poly(acrylic acid) polyelectrolyte complex membranes for pervaporation dehydration of ethylene glycol aqueous solution. J. Membr. Sci. 2007;293:142-150.

     Not in our library10.1016/j.memsci.2007.02.009

202. 202.

     Du J.R., Chakma A., Feng X. Dehydration of ethylene glycol by pervaporation using poly(N,N-dimethylaminoethyl methacrylate)/polysulfone composite membranes. Sep. Purif. Technol. 2008;64:63-70.

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203. 203.

     Hyder M.N., Chen P. Pervaporation dehydration of ethylene glycol with chitosan-poly(vinyl alcohol) blend membranes: Effect of CS-PVA blending ratios. J. Membr. Sci. 2009;340:171-180.

     Not in our library10.1016/j.memsci.2009.05.021

204. 204.

     Cao S., Shi Y., Chen G. Properties and pervaporation characteristics of chitosan-poly(N-vinyl-2-pyrrolidone) blend membranes for MeOH-MTBE. J. Appl. Polym. Sci. 1999;74:1452-1458.

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205. 205.

     Yong Nam S., Moo Lee Y. Pervaporation separation of methanol/methyl t-butyl ether through chitosan composite membrane modified with surfactants. J. Membr. Sci. 1999;157:63-71.

     Not in our library10.1016/s0376-7388(98)00368-8

206. 206.

     Huang R.Y.M., Moon G.Y., Pal R. Chitosan/anionic surfactant complex membranes for the pervaporation separation of methanol/MTBE and characterization of the polymer/surfactant system. J. Membr. Sci. 2001;184:1-15.

     Not in our library10.1016/s0376-7388(00)00604-9

207. 207.

     Huang R.Y.M., Moon G.Y., Pal R. N-acetylated chitosan membranes for the pervaporation separation of alcohol/toluene mixtures. J. Membr. Sci. 2000;176:223-231.

     Not in our library10.1016/s0376-7388(00)00443-9

208. 208.

     Patil M.B., Aminabhavi T.M. Pervaporation separation of toluene/alcohol mixtures using silicalite zeolite embedded chitosan mixed matrix membranes. Sep. Purif. Technol. 2008;62:128-136.

     Not in our library10.1016/j.seppur.2008.01.013

209. 209.

     Won W., Feng X., Lawless D. Pervaporation with chitosan membranes: Separation of dimethyl carbonate/methanol/water mixtures. J. Membr. Sci. 2002;209:493-508.

     Not in our library10.1016/s0376-7388(02)00367-8

210. 210.

     Liu B., Cao Y., Wang T., Yuan Q. Preparation of Novel ZSM-5 Zeolite-Filled Chitosan Membranes for Pervaporation Separation of Dimethyl Carbonate/Methanol Mixtures. J. Appl. Polym. Sci. 2007;116:2117-2125.

     Not in our library10.1002/app.26876

211. 211.

     Lu L., Peng F., Jiang Z., Wang J. Poly(vinyl alcohol)/chitosan blend membranes for pervaporation of benzene/cyclohexane mixtures. J. Appl. Polym. Sci. 2006;101:167-173.

     Not in our library10.1002/app.23158

212. 212.

     Shen J., Chu Y., Ruan H., Wu L., Gao C., Van der Bruggen B. Pervaporation of benzene/cyclohexane mixtures through mixed matrix membranes of chitosan and Ag+/carbon nanotubes. J. Membr. Sci. 2014;462:160-169.

     Not in our library10.1016/j.memsci.2014.03.040

213. 213.

     Anjali Devi D., Smitha B., Sridhar S., Aminabhavi T.M. Dehydration of 1,4-dioxane through blend membranes of poly(vinyl alcohol) and chitosan by pervaporation. J. Membr. Sci. 2006;280:138-147.

     Not in our library10.1016/j.memsci.2006.01.006

214. 214.

     Smitha B., Dhanuja G., Sridhar S. Dehydration of 1,4-dioxane by pervaporation using modified blend membranes of chitosan and nylon 66. Carbohydr. Polym. 2006;66:463-472.

     Not in our library10.1016/j.carbpol.2006.04.006

215. 215.

     Reddy A.S., Kalyani S., Kumar N.S., Boddu V.M., Krishnaiah A. Dehydration of 1,4-dioxane by pervaporation using crosslinked calcium alginate-chitosan blend membranes. Polym. Bull. 2008;61:779-790.

     Not in our library10.1007/s00289-008-1003-x

216. 216.

     Ong Y.T., Ahmad A.L., Zein S.H.S., Sudesh K., Tan S.H. Poly(3-hydroxybutyrate)-functionalised multi-walled carbon nanotubes/chitosan green nanocomposite membranes and their application in pervaporation. Sep. Purif. Technol. 2011;76:419-427.

     Not in our library10.1016/j.seppur.2010.11.013

217. 217.

     Li Q., Yu P., Zhu T., Zhang L., Li Q., Luo Y. Pervaporation performance of crosslinked PVA and chitosan membranes for dehydration of caprolactam solution. Desalin. Water Treat. 2010;16:304-312.

     Not in our library10.5004/dwt.2010.1568

218. 218.

     Lin W., Li Q., Zhu T. New chitosan/Konjac glucomannan blending membrane for application in pervaporation dehydration of caprolactam solution. J. Ind. Eng. Chem. 2012;18:934-940.

     Not in our library10.1016/j.jiec.2011.09.008

219. 219.

     Li Q., Lin W., Zhu T., Luo Y., Yu P. New chitosan/poly (acrylic acid) composite membrane for application in pervaporation dehydration of caprolactam solution. Desalin. Water Treat. 2012;43:43-51.

     Not in our library10.1080/19443994.2012.672197

220. 220.

     Sahu P.K., Sahu P.K., Gupta S.K., Agarwal D.D. Chitosan: An efficient, reusable, and biodegradable catalyst for green synthesis of heterocycles. Ind. Eng. Chem. Res. 2014;53:2085-2091.

     Not in our library10.1021/ie402037d

221. 221.

     Safari J., Zarnegar Z., Sadeghi M., Azizi F. Chitosan-SO3H: An efficient and biodegradable catalyst for the green syntheses of 1,4-dihydropyridines. Curr. Org. Chem. 2016;20:2926-2932.

     Not in our library10.2174/1385272820666160805112208

222. 222.

     Guibal E., Vincent T., Navarro R. Metal ion biosorption on chitosan for the synthesis of advanced materials. J. Mater. Sci. 2014;49:5505-5518.

     Not in our library10.1007/s10853-014-8301-5

223. 223.
     “The Good, the Bad and the Ugly” of Chitosans · 2016

     No notice
224. 224.
     O-Carboxymethyl Chitosan Supported Heterogeneous Palladium and Ni Catalysts for Heck Reaction · 2017

     Not checked
225. 225.

     Bradshaw M., Zou J., Byrne L., Swaminathan Iyer K., Stewart S.G., Raston C.L. Pd(ii) conjugated chitosan nanofibre mats for application in Heck cross-coupling reactions. Chem. Commun. 2011;47:12292-12294.

     Not in our library10.1039/c1cc14717j

226. 226.

     Hajipour A.R., Boostani E., Mohammadsaleh F. Proline-functionalized chitosan-palladium(ii) complex, a novel nanocatalyst for C-C bond formation in water. RSC Adv. 2015;5:24742-24748.

     Not in our library10.1039/c5ra01187f

227. 227.

     Baran T., Sargin I., Menteş A., Kaya M. Exceptionally high turnover frequencies recorded for a new chitosan-based palladium(II) catalyst. Appl. Catal. A Gen. 2016;523:12-20.

     Not in our library10.1016/j.apcata.2016.05.012

228. 228.

     Baran T., Menteş A. Microwave assisted synthesis of biarlys by C-C coupling reactions with a new chitosan supported Pd(II) catalyst. J. Mol. Struct. 2016;1122:111-116.

     Not in our library10.1016/j.molstruc.2016.05.091

229. 229.

     Zeng M., Sun X., Qi C., Zhang X.M. Preparation of a novel CuI/PCMS heterogeneous catalyst for heck-type cross-coupling reactions. Kinet. Catal. 2013;54:716-723.

     Not in our library10.1134/s0023158413060141

230. 230.

     Rafiee F., Hosseini S.A. CNC pincer palladium complex supported on magnetic chitosan as highly efficient and recyclable nanocatalyst in C─C coupling reactions. Appl. Organomet. Chem. 2018;32:1-10.

     Not in our library10.1002/aoc.4519

231. 231.

     Fakhri A., Naghipour A. Organometallic polymer-functionalized Fe3O4 nanoparticles as a highly efficient and eco-friendly nanocatalyst for C–C bond formation. Transit. Met. Chem. 2018;43:463-472.

     Not in our library10.1007/s11243-018-0233-5

232. 232.

     Jadhav S., Kumbhar A., Salunkhe R. Palladium supported on silica-chitosan hybrid material (Pd-CS@SiO2) for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions. Appl. Organomet. Chem. 2015;29:339-345.

     Not in our library10.1002/aoc.3290

233. 233.

     Zeng M., Yuan X., Zuo S., Qi C. Novel chitosan-based/montmorillonite/palladium hybrid microspheres as heterogeneous catalyst for Sonogashira reactions. RSC Adv. 2015;5:37995-38000.

     Not in our library10.1039/c5ra01902h

234. 234.

     Affrose A., Suresh P., Azath I.A., Pitchumani K. Palladium nanoparticles embedded on thiourea-modified chitosan: A green and sustainable heterogeneous catalyst for the Suzuki reaction in water. RSC Adv. 2015;5:27533-27539.

     Not in our library10.1039/c4ra14411b

235. 235.

     Veisi H., Ghadermazi M., Naderi A. Biguanidine-functionalized chitosan to immobilize palladium nanoparticles as a novel, efficient and recyclable heterogeneous nanocatalyst for Suzuki-Miyaura coupling reactions. Appl. Organomet. Chem. 2016;30:341-345.

     Not in our library10.1002/aoc.3437

236. 236.

     Sophiphun O., Wittayakun J., Dhital R.N., Haesuwannakij S., Murugadoss A., Sakurai H. Gold/palladium bimetallic alloy nanoclusters stabilized by chitosan as highly efficient and selective catalysts for homocoupling of arylboronic acid. Aust. J. Chem. 2012;65:1238-1243.

     Not in our library10.1071/ch12175

237. 237.

     Hajipour A.R., Abolfathi P. Novel triazole-modified chitosan@nickel nanoparticles: Efficient and recoverable catalysts for Suzuki reaction. New J. Chem. 2017;41:2386-2391.

     Not in our library10.1039/c6nj03789e

238. 238.

     Ruiz-Castillo P., Buchwald S.L. Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions. Chem. Rev. 2016;116:12564-12649.

     Not in our library10.1021/acs.chemrev.6b00512

239. 239.

     Wang L.-X., Wang Z.-W., Wang G.-S., Lin X.-D., Ren J.-G. Catalytic performance of chitosan-Schiff base supported Pd/Co bimetallic catalyst for acrylamide with phenyl halide. Polym. Adv. Technol. 2010;21:244-249.

     Not in our library

240. 240.

     Anuradha, Kumari S., Pathak D.D. Synthesis and development of Chitosan anchored copper(II) Schiff base complexes as heterogeneous catalysts for N-arylation of amines. Tetrahedron Lett. 2015;56:4135-4142.

     Not in our library10.1016/j.tetlet.2015.05.049

241. 241.

     Bodhak C., Kundu A., Pramanik A. An efficient and recyclable chitosan supported copper(II) heterogeneous catalyst for C-N cross coupling between aryl halides and aliphatic diamines. Tetrahedron Lett. 2015;56:419-424.

     Not in our library10.1016/j.tetlet.2014.11.120

242. 242.

     Nasir Baig R.B., Vaddula B.R., Gonzalez M.A., Varma R.S. N-Allylation of amines with allyl acetates using chitosan-immobilized palladium. RSC Adv. 2014;4:9103-9106.

     Not in our library10.1039/c3ra47899h

243. 243.

     Shen C., Xu J., Yu W., Zhang P. A highly active and easily recoverable chitosan@copper catalyst for the C-S coupling and its application in the synthesis of zolimidine. Green Chem. 2014;16:3007-3012.

     Not in our library10.1039/c4gc00161c

244. 244.

     Frindy S., El Kadib A., Lahcini M., Primo A., García H. Copper Nanoparticles Stabilized in a Porous Chitosan Aerogel as a Heterogeneous Catalyst for C-S Cross-coupling. ChemCatChem. 2015;7:3307-3315.

     Not in our library10.1002/cctc.201500565

245. 245.

     Chiessi E., Pispisa B. Polymer-supported catalysis: Oxidation of catecholamines by Fe(III) and Cu(II) complexes immobilized to chitosan. J. Mol. Catal. 1994;87:177-193.

     Not in our library10.1016/0304-5102(93)e0235-9

246. 246.

     Huang G., Guo C.C., Tang S.S. Catalysis of cyclohexane oxidation with air using various chitosan-supported metallotetraphenylporphyrin complexes. J. Mol. Catal. A Chem. 2007;261:125-130.

     Not in our library10.1016/j.molcata.2006.08.014

247. 247.

     Huang G., Luo J., Cai C.C., Guo Y.A., Luo G.W. The influence of chitosan on the performances of mono and μ-oxo dimeric iron tetraphenylporphyrins catalysts for aerobic oxidation of toluene. Catal. Commun. 2008;9:1882-1885.

     Not in our library10.1016/j.catcom.2008.03.007

248. 248.

     Di Giuseppe A., Crucianelli M., Passacantando M., Nisi S., Saladino R. Chitin- and chitosan-anchored methyltrioxorhenium: An innovative approach for selective heterogeneous catalytic epoxidations of olefins. J. Catal. 2010;276:412-422.

     Not in our library10.1016/j.jcat.2010.10.003

249. 249.

     Hatefi Ardakani M., Moghadam M., Saeednia S., Pakdin-Parizi Z. Epoxidation of alkenes with NaIO4 catalyzed by an efficient and reusable natural polymer-supported ruthenium(III) salophen catalyst. J. Iran. Chem. Soc. 2016;13:631-636.

     Not in our library10.1007/s13738-015-0774-x

250. 250.

     Ghiaci M., Dorostkar N., Martínez-Huerta M.V., Fierro J.L.G., Moshiri P. Synthesis and characterization of gold nanoparticles supported on thiol functionalized chitosan for solvent-free oxidation of cyclohexene with molecular oxygen. J. Mol. Catal. A Chem. 2013;379:340-349.

     Not in our library10.1016/j.molcata.2013.08.030

251. 251.

     Shaabani A., Boroujeni M.B., Sangachin M.H. Cobalt-chitosan: Magnetic and biodegradable heterogeneous catalyst for selective aerobic oxidation of alkyl arenes and alcohols. J. Chem. Sci. 2015;127:1927-1935.

     Not in our library10.1007/s12039-015-0959-y

252. 252.

     Murugadoss A., Sakurai H. Chitosan-stabilized gold, gold-palladium, and gold-platinum nanoclusters as efficient catalysts for aerobic oxidation of alcohols. J. Mol. Catal. A Chem. 2011;341:1-6.

     Not in our library10.1016/j.molcata.2011.03.019

253. 253.

     Shen C., Qiao J., Zhao L., Zheng K., Jin J., Zhang P. An efficient silica supported Chitosan@vanadium catalyst for asymmetric sulfoxidation and its application in the synthesis of esomeprazole. Catal. Commun. 2017;92:114-118.

     Not in our library10.1016/j.catcom.2017.01.018

254. 254.

     Barskiy D.A., Kovtunov K.V., Primo A., Corma A., Kaptein R., Koptyug I.V. Selective Hydrogenation of 1,3-Butadiene and 1-Butyne over a Rh/Chitosan Catalyst Investigated by using Parahydrogen-Induced Polarization. ChemCatChem. 2012;4:2031-2035.

     Not in our library10.1002/cctc.201200414

255. 255.

     Wu L.H., Nordin M.R., Yaakob Z., Liew K.Y., Li J.L. Effects of Fe on catalytic hydrogenation of palm oil in aqueous solution. Chem. Pap. 2017;71:119-126.

     Not in our library10.1007/s11696-016-0063-x

256. 256.

     Adlim M., Bakar M.A. The properties of Pd/Au bimetallic colloidal catalysts stabilized by chitosan and prepared by simultaneous and stepwise chemical reduction of the precursor ions. Kinet. Catal. 2013;54:586-596.

     Not in our library10.1134/s0023158413050017

257. 257.

     Zhou J., Dong Z., Yang H., Shi Z., Zhou X., Li R. Pd immobilized on magnetic chitosan as a heterogeneous catalyst for acetalization and hydrogenation reactions. Appl. Surf. Sci. 2013;279:360-366.

     Not in our library10.1016/j.apsusc.2013.04.113

258. 258.

     Liu B., Zhou H., Li Y., Wang J. Asymmetric transfer hydrogenation of acetophenone promoted by chitosan ester ruthenium complex. Chin. J. Org. Chem. 2014;34:2554-2558.

     Not in our library10.6023/cjoc201406025

259. 259.

     Szőllősi G., Kolcsár V.J. Highly Enantioselective Transfer Hydrogenation of Prochiral Ketones Using Ru(II)-Chitosan Catalyst in Aqueous Media. ChemCatChem. 2019;11:820-830.

     Not in our library10.1002/cctc.201801602

260. 260.

     Viswanadhan M., Potdar A., Divakaran A., Badiger M., Rode C. Product distribution in hydrogenation of styrene oxide over Pd/chitosan catalyst. Res. Chem. Intermed. 2016;42:7581-7595.

     Not in our library10.1007/s11164-016-2554-3

261. 261.

     Ríos-Caloch G., Santes V., Escobar J., Pérez-Romo P., Díaz L., Lartundo-Rojas L. Effect of Chitosan on the Performance of NiMoP-Supported Catalysts for the Hydrodesulfurization of Dibenzothiophene. J. Nanomater. 2016;2016:13.

     Not in our library10.1155/2016/4047874

262. 262.

     Lee S.B., Jeong G.T. Catalytic Conversion of Chitosan to 5-Hydroxymethylfurfural Under Low Temperature Hydrothermal Process. Appl. Biochem. Biotechnol. 2015;176:1151-1161.

     Not in our library10.1007/s12010-015-1636-9

263. 263.

     Li M., Zang H., Feng J., Yan Q., Yu N., Shi X., Cheng B. Efficient conversion of chitosan into 5-hydroxymethylfurfural via hydrothermal synthesis in ionic liquids aqueous solution. Polym. Degrad. Stab. 2015;121:331-339.

     Not in our library10.1016/j.polymdegradstab.2015.09.009

264. 264.

     Wang Y., Pedersen C.M., Deng T., Qiao Y., Hou X. Direct conversion of chitin biomass to 5-hydroxymethylfurfural in concentrated ZnCl2 aqueous solution. Bioresour. Technol. 2013;143:384-390.

     Not in our library10.1016/j.biortech.2013.06.024

265. 265.

     Chen X., Yang H., Yan N. Shell Biorefinery: Dream or Reality? Chem. Eur. J. 2016;22:13402-13421.

     Not in our library10.1002/chem.201602389

266. 266.

     Bozell J.J., Holladay J.E., Johnson D., White J.F. Top Value Added Chemicals from Biomass Volume II: Results of Screening for Potential Candidates from Biorefinery Lignin Produced. 2007.

     Not in our library

267. 267.

     van Putten R.-J., de Vries J.G., van der Waal J.C., de Jong E., Rasrendra C.B., Heeres H.J. Hydroxymethylfurfural, A Versatile Platform Chemical Made from. Chem. Rev. 2013;113:1499-1597.

     Not in our library10.1021/cr300182k

268. 268.

     Szabolcs Á., Molnár M., Dibó G., Mika L.T. Microwave-assisted conversion of carbohydrates to levulinic acid: An essential step in biomass conversion. Green Chem. 2013;15:439-445.

     Not in our library10.1039/c2gc36682g

269. 269.

     Omari K.W., Besaw J.E., Kerton F.M. Hydrolysis of chitosan to yield levulinic acid and 5-hydroxymethylfurfural in water under microwave irradiation. Green Chem. 2012;14:1480-1487.

     Not in our library10.1039/c2gc35048c

270. 270.

     Jeong G.T. Production of levulinic acid from glucosamine by dilute-acid catalyzed hydrothermal process. Ind. Crop. Prod. 2014;62:77-83.

     Not in our library10.1016/j.indcrop.2014.08.006

271. 271.

     Ohmi Y., Nishimura S., Ebitani K. Synthesis of α-amino acids from glucosamine-HCl and its derivatives by aerobic oxidation in water catalyzed by au nanoparticles on basic supports. ChemSusChem. 2013;6:2259-2262.

     Not in our library10.1002/cssc.201300303

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• Novel Trends in Hydrogel Development for Biomedical Applications: A Review · 2022
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• Polylactic Acid (PLA) Biocomposite: Processing, Additive Manufacturing and Advanced Applications · 2021
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