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Ultrasonic-assisted condensation of chitosan with salicylaldehyde

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Abstract

In order to synthesize an improved adsorbent for heavy metal ions, we studied the condensation reaction of chitosan with salicylaldehyde in ethanol to form a Schiff base. The effect irradiating the reaction using an ultrasonic liquid processor was contrasted with conventional methods. The IR spectra of condensed chitosan prepared by the two methods showed that their molecular structures were identical. The reaction conditions, including solvents, ultrasonic power density and irradiation time, pH, and reactant ratio, were optimized by orthogonal design. A shorter reaction time and a higher product yield were obtained using ultrasonic-assisted synthesis compared with the traditional method. A condensation degree of 89.63% was achieved using the optimized conditions: i.e. ultrasonic irradiation at 180 W for 60 min; 95% ethanol as the solvent, pH 4.0, and salicylaldehyde:chitosan ratio of 6:1.

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References

  • Chan P, Kurisawa M, Chung J E, Yang Y Y. 2007. Synthesis and characterization of chitosan-g-poly(ethylene glycol)-folate as a non-viral carrier for tumor-targeted gene delivery. Biomaterials, 28: 540–549.

    Article  Google Scholar 

  • Crini G, Badot P M. 2008. Application of chitosan, a natural aminopolysaccharide, for dye removal from aqueous solutions by adsorption processes using batch studies: A review of recent literature. Progress in Polymer Science, 33: 399–447.

    Article  Google Scholar 

  • Drofenik M, Kristl M, Makovec D, Jagličić Z, Hanžel D. 2008. Sonochemically assisted synthesis of zinc-doped maghemite. Ultrasonics Sonochemistry, 15: 791–798.

    Article  Google Scholar 

  • Ghasemi S, Mousavi M F, Shamsipur M, Karami H. 2008. Sonochemical-assisted synthesis of nano-structured lead dioxide. Ultrasonics Sonochemistry, 15: 448–455.

    Article  Google Scholar 

  • Jayakumar R, Nwe N, Tokura S, Tamura H. 2007. Sulfated chitin and chitosan as novel biomaterials. International Journal of Biological Macromolecules, 40: 175–181.

    Article  Google Scholar 

  • Kim I Y, Seo S J, Moon H S. 2008. Chitosan and its derivatives for tissue engineering applications. Biotechnology Advances, 26: 1–21.

    Article  Google Scholar 

  • Kim T H, Jiang H L, Dhananjay J. 2007. Chemical modification of chitosan as a gene carrier in vitro and in vivo. Progress in Polymer Science, 32: 726–753.

    Article  Google Scholar 

  • Krajewska B. 2005. Membrane-based processes performed with use of chitin/chitosan materials. Separation and Purification Technology, 41: 305–312.

    Article  Google Scholar 

  • Ma G. 2008. Preparation and characterization of water-soluble N-alkylated chitosan. Carbohydrate Polymers, 74: 121–126.

    Article  Google Scholar 

  • Majeti N V, Ravi K. 2000. A review of chitin and chitosan applications. Reactive & Functional Polymers, 46: 1–27.

    Article  Google Scholar 

  • Manuel G, Antonio S N, Maria E M. 1992. A derivative of chitosan and 2,4-pentanedione with strong chelating properties. Carbohydrate Research, 233: 255–259.

    Article  Google Scholar 

  • Neppolian B, Wang Q, Jung H, Choi H. 2008. Ultrasonic-assisted sol-gel method of preparation of TiO2 nano-particles: Characterization, properties and 4-chlor-ophenol removal application. Ultrasonics Sonochemistry, 15: 649–658.

    Google Scholar 

  • Qu R, Ma Q, Zheng X, Sun Y. 1995. Preparation of chitosan derivatives and their adsorption behavior. Chinese Journal of Applied Chemistry, 12: 117–118.

    Google Scholar 

  • Pasanphan W, Chirachanchai S. 2008. Conjugation of gallic acid onto chitosan: An approach for green and water-based antioxidant. Carbohydrate Polymers, 72: 169–177.

    Article  Google Scholar 

  • Perrin D D, interpreted by Shi Y. 1987. Purified methods of chemical leechdom in laboratory, Chemical industry publishing company. 320p.

  • Qu R, Zheng X, Sun Y. 1995. Preparation of chitosan derivatives and their adsorption behavior. Chinese Journal of Applied Chemistry, 12: 117–118.

    Google Scholar 

  • Rinaudo M. 2006. Chitin and chitosan: Properties and applications. Progress in Polymer Science, 31: 603–632.

    Article  Google Scholar 

  • Schuetz Y B, Gurny R, Jordan O. 2008. A novel thermoresponsive hydrogel based on chitosan. European Journal of Pharmaceutics and Biopharmaceutics, 68: 19–25.

    Article  Google Scholar 

  • Sinha V R, Singla A K, Wadhawan S, Kaushik R, Kumria R, Bansal K, Dhawan S. 2004. Chitosan microspheres as a potential carrier for drugs. International Journal of Pharmaceutics, 274: 1–33.

    Article  Google Scholar 

  • Stavarache C, Vinatoru M, Maeda Y. 2007. Aspects of ultrasonically assisted transesterification of various vegetable oils with methanol. Ultrasonics Sonochemistry, 14: 380–386.

    Article  Google Scholar 

  • Tian X L, Liu Z. 1997. Study of condensation chitosan by salicylaldehyde. Chinese Journal of Guangxi Normal University, Supplement: 268–272. (in Chinese)

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Correspondence to Siyuan Guo  (郭祀远).

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Supported by Doctoral Discipline Special Foundation, Education Ministry of China (No. 20050561014), and the National High Technology Research and Development Program of China (863 Program) (No. 2007AA100405)

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Duan, L., Guo, S., Yang, J. et al. Ultrasonic-assisted condensation of chitosan with salicylaldehyde. Chin. J. Ocean. Limnol. 27, 882–886 (2009). https://doi.org/10.1007/s00343-009-9204-1

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  • DOI: https://doi.org/10.1007/s00343-009-9204-1

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