title: A simple and convenient method to synthesize N-[(2-hydroxyl)-propyl-3-trimethylammonium] chitosan chloride in an ionic liquid.
abstract: N-[(2-Hydroxyl)-propyl-3-trimethyl ammonium] chitosan chloride (HTCC) was synthesized through nucleophilic substitution of 2,3-epoxypropyltrimethyl ammonium chloride (EPTAC) onto chitosan using ionic liquid of 1-allyl-3-methylimidazole chloride (AmimCl) as a homogeneous and green reaction media. The chemical structure of HTCC was confirmed by FTIR, (1)H NMR and (13)C NMR. The FTIR peak intensity of amino group at 1595 cm(-1) decreased and that of [Formula: see text] at 1475 cm(-1) increased with the increase of reaction time, confirming the substitution of EPTAC on CS. The degree of substitutions (DS) were calculated from the integral area of (1)H NMR, and the optimum reaction condition was obtained, namely, reaction time of 8h, temperature of 80°C and [Formula: see text] of 3/1. The degree of crystallinity and thermal properties of HTCC were characterized by XRD, TG, DSC, and DMA methods. Data from XRD, TG, DSC and DMA show that the degree of crystallinity, thermal stability, as well as glass transition temperature of HTCC decreased with the increase of DS. The reaction mechanism of chitosan with EPTAC in AmimCl was elucidated by performing density functional theory (DFT) calculations.
authors.affiliation: Key Laboratory of Fine Chemicals (Shandong Province), Qilu University of Technology, Jinan 250353, PR China.
authors.forename: Xiaodeng
authors.initials: X
authors.lastname: Yang
authors.affiliation: Key Laboratory of Fine Chemicals (Shandong Province), Qilu University of Technology, Jinan 250353, PR China.
authors.forename: Chuanguang
authors.initials: C
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Fine Chemicals (Shandong Province), Qilu University of Technology, Jinan 250353, PR China.
authors.forename: Congde
authors.initials: C
authors.lastname: Qiao
authors.affiliation: Key Laboratory of Colloid and Interface Chemistry (Ministry of Education), Shandong University, Jinan 250100, PR China.
authors.forename: Xueli
authors.initials: X
authors.lastname: Mu
authors.affiliation: Key Laboratory of Fine Chemicals (Shandong Province), Qilu University of Technology, Jinan 250353, PR China. Electronic address: litianduo@163.com.
authors.forename: Tianduo
authors.initials: T
authors.lastname: Li
authors.affiliation: Key Laboratory of Fine Chemicals (Shandong Province), Qilu University of Technology, Jinan 250353, PR China.
authors.forename: Jinku
authors.initials: J
authors.lastname: Xu
authors.affiliation: Key Laboratory of Fine Chemicals (Shandong Province), Qilu University of Technology, Jinan 250353, PR China.
authors.forename: Lei
authors.initials: L
authors.lastname: Shi
authors.affiliation: Key Laboratory of Colloid and Interface Chemistry (Ministry of Education), Shandong University, Jinan 250100, PR China. Electronic address: zhangdj@sdu.edu.cn.
authors.forename: Dongju
authors.initials: D
authors.lastname: Zhang
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D048271:Chitosan / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007093:Imidazoles / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis*; D017550:Spectroscopy, Fourier Transform Infrared; D014961:X-Ray Diffraction
chemical_list: C544334:1-allyl-3-methylimidazolium; D000498:Allyl Compounds; D007093:Imidazoles; D052578:Ionic Liquids; D000644:Quaternary Ammonium Compounds; C576941:hydroxypropyltrimethyl ammonium chloride chitosan; D048271:Chitosan
keywords: 2,3-Epoxypropyltrimethyl ammonium chloride; AmimCl; Chitosan; Homogeneous reaction; N-[(2-Hydroxyl)-propyl-3-trimethyl ammonium] chitosan chloride