Cloisite 15Aº nanoclay as an effective PTC for the epoxidation of hydroxyl terminated polybutadiene (HTPB)

A simple method is reported for the epoxidation of hydroxyl-terminated polybutadiene (HTPB) by using in-situ generated dimethyl dioxirane (DMD) as an oxidant and Cloisite 15Ao nanoclay as a phase-transfer catalyst (PTC). In order to find the optimum reaction conditions, real time analyses of the products as well as epoxidation progress, followed by 1HNMR and FTIR techniques at various reaction times and different PTC concentrations, were done. Obtained data revealed the selectivity of DMD/ Cloisite 15Ao in predominant cis double bonds epoxidation in comparison with trans and pendant vinyl functional groups.

[1]  Hassan Hajifatheali,et al.  Performance of dimethyl dioxirane/nano-TiO2 on epoxidation of polybutadiene and hydroxyl terminated polybutadiene , 2013 .

[2]  Hassan Hajifatheali,et al.  The Role of Cloisite 30B as a Phase Transfer Catalyst (PTC) in Polybutadiene Epoxidation , 2011 .

[3]  Hassan Hajifatheali,et al.  Nanoclay-Mediated Epoxidation of HTPB Using In-Situ-Generated Dimethyl Dioxirane , 2011 .

[4]  Li Wang,et al.  Kinetics of Epoxidation of Hydroxyl-Terminated Polybutadiene with Hydrogen Peroxide under Phase Transfer Catalysis , 2009 .

[5]  Z. Mozaffari,et al.  In situ Generated Dimethyl Dioxirane (DMD)/Copper(II) (2,2'-diamino-4, 4'-bithiazole) Complex as a New Oxidant for Polybutadiene and Hydroxyl Terminated Polybutadiene (HTPB) Epoxidation , 2009 .

[6]  Mir Mohammad Alavi Nikje,et al.  Polybutadiene and Hydroxyl-Terminated Polybutadiene Epoxidation Using In Situ-Generated Dimethyl Dioxirane (DMD)/Transition Metal Salts Complex , 2008 .

[7]  Z. Mozaffari,et al.  Chemoselective epoxidation of hydroxyl-terminated polybutadiene (HTPB) using in-situ generated dimethyl dioxirane (DMD) , 2007 .

[8]  Y. Henríquez,et al.  Catalytic properties of silica supported titanium, vanadium and niobium oxide nanoparticles towards the oxidation of saturated and unsaturated hydrocarbons , 2006 .

[9]  M. Haghshenas,et al.  Epoxidation of polybutadiene using in situ generated dimethyl dioxirane (DMD) in the presence of tetra-n-butyl ammonium bromide , 2006 .

[10]  M. Alizadeh,et al.  Immobilized copper(II) complexes on montmorillonite and MCM-41 as selective catalysts for epoxidation of alkenes , 2005 .

[11]  V. Aggarwal,et al.  New insights in the mechanism of amine catalyzed epoxidation: dual role of protonated ammonium salts as both phase transfer catalysts and activators of oxone. , 2003, Journal of the American Chemical Society.

[12]  S. Assabumrungrat,et al.  Extractive reaction for epoxidation of cyclohexene to cyclohexene oxide using dioxirane in ketone/Oxone® system , 2003 .

[13]  Jen-Ming Yang,et al.  Properties of modified hydroxyl-terminated polybutadiene based polyurethane membrane , 2002 .

[14]  Jen-Ming Yang,et al.  Properties of HTPB based polyurethane membrane prepared by epoxidation method , 2001 .

[15]  Steven J. Brenek,et al.  A safe, scaleable method for the oxidation of carbonboron bonds with oxone , 2000 .

[16]  S. Sundarrajan,et al.  Primary Pyrolysis Products of Hydroxy-Terminated Polybutadiene , 2000 .

[17]  T. Reitberger,et al.  Thermal oxidation of hydroxyl-terminated polybutadiene rubber I. Chemiluminescence studies , 1999 .

[18]  J. Edwards,et al.  H-Bonding Interactions in the Epoxidation of Alkenylammonium Salts with Dimethyldioxirane and m-Chloroperbenzoic Acid: A Kinetic Study. , 1999, The Journal of organic chemistry.

[19]  S. Girois,et al.  Polym. Degrad. Stab. , 1996 .

[20]  Erik D. Sall,et al.  Functionalization of Polymers by Metal-Mediated Processes , 1995 .

[21]  L. Akcelrud,et al.  Characterization of hydroxyl-terminated polybutadiene , 1994 .

[22]  N. Cheremisinoff,et al.  Elastomer Technology Handbook , 1993 .

[23]  A. S. Hay,et al.  Epoxidation of unsaturated polymers with hydrogen peroxide , 1990 .

[24]  E. Ruckenstein,et al.  Encapsulation of solid particles by the concentrated emulsion polymerization method , 1990 .

[25]  D. Żuchowska.  Polybutadiene modified by epoxidation. 1. Effect of polybutadiene microstructure on the reactivity of double bonds , 1980 .

[26]  B. S. Turov,et al.  Kinetics and mechanism of epoxidation of low-molecular weight cis-butadiene rubber by tert-butyl hydroperoxide☆ , 1980 .

[27]  Henry Lee,et al.  Handbook of Epoxy Resins , 1967 .