A novel approach of utilizing quaternized chitosan as a catalyst for the eco-friendly cycloaddition of epoxides with CO2

A novel attempt of using quaternized chitosan (QCHT) as a catalyst for the cycloaddition reaction of allyl glycidyl ether (AGE) and CO2 under solvent-free conditions has been made. The surface quaternization of CHT has been characterized by means of various physicochemical methods, such as X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), and elemental analysis. The effects of reaction parameters like catalyst amount, reaction time, reaction temperature, and CO2 pressure have been investigated. The catalyst system was recyclable and was reused. It has been demonstrated that the inherently present hydroxyl group in the catalyst had a synergistic effect with halide anions, and a high yield of cyclic carbonates and excellent selectivity could be obtained under optimum conditions. These results reveal that QCHT is an efficient and environmentally friendly catalyst for the cycloaddition reaction.

[1]  Suojiang Zhang,et al.  Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO2 , 2012 .

[2]  A. Gaumont,et al.  Catalytic materials based on catalysts containing ionic liquid phase supported on chitosan or alginate: Importance of the support , 2011 .

[3]  S. Klaus,et al.  Recent advances in CO2/epoxide copolymerization—New strategies and cooperative mechanisms , 2011 .

[4]  Lina Han,et al.  Ionic liquids containing carboxyl acid moieties grafted onto silica: Synthesis and application as heterogeneous catalysts for cycloaddition reactions of epoxide and carbon dioxide , 2011 .

[5]  Lina Han,et al.  Porous polymer bead-supported ionic liquids for the synthesis of cyclic carbonate from CO2 and epoxide , 2011 .

[6]  S. Kiatkamjornwong,et al.  Enhancing antibacterial activity of chitosan surface by heterogeneous quaternization , 2011 .

[7]  U. Ruktanonchai,et al.  Quaternization of N-(3-pyridylmethyl) chitosan derivatives: Effects of the degree of quaternization, molecular weight and ratio of N-methylpyridinium and N,N,N-trimethyl ammonium moieties on bactericidal activity , 2010 .

[8]  Michael North,et al.  Synthesis of cyclic carbonates from epoxides and CO2 , 2010 .

[9]  Xiaoying Wang,et al.  Preparation and Characterization of Quaternized Chitosan Under Microwave Irradiation , 2010 .

[10]  J. Goupil,et al.  Importance of the Conditioning of the Chitosan Support in a Catalyst‐Containing Ionic Liquid Phase Immobilised on Chitosan: The Palladium‐Catalysed Allylation Reaction Case , 2010 .

[11]  Mikkel Jørgensen,et al.  The teraton challenge. A review of fixation and transformation of carbon dioxide , 2010 .

[12]  Dae-Won Park,et al.  Synthesis of cyclic carbonate from allyl glycidyl ether and carbon dioxide using ionic liquid-functionalized amorphous silica , 2009 .

[13]  Suojiang Zhang,et al.  Reusable and efficient polymer-supported task-specific ionic liquid catalyst for cycloaddition of epoxide with CO2 , 2009 .

[14]  Lina Han,et al.  Silica grafted imidazolium-based ionic liquids: efficient heterogeneous catalysts for chemical fixation of CO2 to a cyclic carbonate , 2009 .

[15]  Y. Iwasawa,et al.  Silica-supported aminopyridinium halides for catalytic transformations of epoxides to cyclic carbonates under atmospheric pressure of carbon dioxide , 2009 .

[16]  S. Yin,et al.  The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts , 2009 .

[17]  Mi-Kyung Lee,et al.  Functionalization of organic ions on hybrid MCM-41 for cycloaddition reaction: The effective conversion of carbon dioxide , 2009 .

[18]  I. Aranaz,et al.  Functional Characterization of Chitin and Chitosan , 2009 .

[19]  M. North,et al.  One-component catalysts for cyclic carbonate synthesis. , 2009, Chemical communications.

[20]  Mi-Kyung Lee,et al.  Imidazolium derivatives functionalized MCM-41 for catalytic conversion of carbon dioxide to cyclic carbonate , 2009 .

[21]  Pengcheng Li,et al.  Synthesis and hydroxyl radicals scavenging activity of quaternized carboxymethyl chitosan , 2008 .

[22]  Jian Sun,et al.  Hydroxyl-functionalized ionic liquid: a novel efficient catalyst for chemical fixation of CO2 to cyclic carbonate , 2008 .

[23]  T. Ema,et al.  Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides , 2008 .

[24]  B. Han,et al.  CO(2) cycloaddition reactions catalyzed by an ionic liquid grafted onto a highly cross-linked polymer matrix. , 2007, Angewandte Chemie.

[25]  Pengcheng Li,et al.  The influence of the cationic of quaternized chitosan on antifungal activity. , 2007, International journal of food microbiology.

[26]  M. Aresta,et al.  Utilisation of CO2 as a chemical feedstock: opportunities and challenges. , 2007, Dalton transactions.

[27]  Liang‐Nian He,et al.  Quaternary ammonium salt-functionalized chitosan: An easily recyclable catalyst for efficient synthesis of cyclic carbonates from epoxides and carbon dioxide , 2007 .

[28]  Hiroyuki Yasuda,et al.  Transformation of carbon dioxide. , 2007, Chemical reviews.

[29]  I. Yamskov,et al.  New approach to the quaternization of chitosan and its amphiphilic derivatives , 2007 .

[30]  K. Qiao,et al.  Rapid synthesis of cyclic carbonates from CO2 and epoxides under microwave irradiation with controlled temperature and pressure , 2007 .

[31]  Anlian Zhu,et al.  Supported choline chloride/urea as a heterogeneous catalyst for chemical fixation of carbon dioxide to cyclic carbonates , 2007 .

[32]  Pengcheng Li,et al.  Hydroxyl radicals scavenging activity of N-substituted chitosan and quaternized chitosan. , 2006, Bioorganic & medicinal chemistry letters.

[33]  Suobo Zhang,et al.  Chitin and chitosan dissolved in ionic liquids as reversible sorbents of CO2 , 2006 .

[34]  Fuwei Li,et al.  Immobilized ionic liquid/zinc chloride: Heterogeneous catalyst for synthesis of cyclic carbonates from carbon dioxide and epoxides , 2006 .

[35]  Jie Wu,et al.  A thermo- and pH-sensitive hydrogel composed of quaternized chitosan/glycerophosphate. , 2006, International journal of pharmaceutics.

[36]  Suobo Zhang,et al.  Highly active, hexabutylguanidinium salt/zinc bromide binary catalyst for the coupling reaction of carbon dioxide and epoxides , 2006 .

[37]  Fuwei Li,et al.  An easily recoverable and efficient natural biopolymer-supported zinc chloride catalyst system for the chemical fixation of carbon dioxide to cyclic carbonate , 2005 .

[38]  L. Sabbatini,et al.  Heck Reaction Catalyzed by Nanosized Palladium on Chitosan in Ionic Liquids , 2004 .

[39]  R. Srivastava,et al.  Synthesis of Polycarbonate Precursors over Titanosilicate Molecular Sieves , 2003 .

[40]  T. Sakakura,et al.  Cyclic carbonate synthesis from supercritical carbon dioxide and epoxide over lanthanide oxychloride , 2002 .

[41]  Masahiko Arai,et al.  Synthesis of dimethyl carbonate and glycols from carbon dioxide, epoxides, and methanol using heterogeneous basic metal oxide catalysts with high activity and selectivity , 2001 .

[42]  Robert J. Davis,et al.  Cycloaddition of CO2 to epoxides over solid base catalysts , 2001 .

[43]  Jiajian Peng,et al.  Cycloaddition of carbon dioxide to propylene oxide catalyzed by ionic liquids , 2001 .

[44]  Y. Ikushima,et al.  Chemical fixation of carbon dioxide to styrene carbonate under supercritical conditions with DMF in the absence of any additional catalysts , 2000 .

[45]  T. Yano,et al.  Magnesium oxide-catalysed reaction of carbon dioxide with anepoxide with retention of stereochemistry , 1997 .

[46]  T. Endo,et al.  Catalytic activity of various salts in the reaction of 2,3-epoxypropyl phenyl ether and carbon dioxide under atmospheric pressure , 1993 .

[47]  M. Rinaudo,et al.  New method for the quaternization of chitosan , 1986 .

[48]  J. Desbrières,et al.  Quaternization of poly(acrylonitrile‐co‐2‐methyl‐5‐vinylpyridine) and properties of the products in N,N‐dimethylformamide solution , 1981 .