The Role of Cloisite 30B as a Phase Transfer Catalyst (PTC) in Polybutadiene Epoxidation

REFERENCES

• Ganesh , K. ; Sundarrajan , S. ; Kishore , K. ; Ninan , K.N. ; George , B. ; Surianarayanan , M. Primary pyrolysis products of hydroxy-terminated polybutadiene . Macromolecules 2000 , 33 , 326 – 330 .
   Web of Science ®Google Scholar
• Park , J.S. ; Ruckensten , E. Encapsulation of solid particles by the concentrated emulsion polymerization method . Polymer 1990 , 31 , 175 – 179 .
   Web of Science ®Google Scholar
• McGrath , M.P. ; Sall , E.D. ; Tremont , S.J. Functionalization of polymers processes . J. Chem. Rev. 1995 , 95 , 381 – 398 .
   Web of Science ®Google Scholar
• Stenberg , B. ; Ahlblad , G. ; Reitberger , T. ; Terselius , B. Thermal oxidation of hydroxyl- terminated polybutadiene rubber I. Chemiluminescence studies . Polym. Degrad. Stab. 1999 , 65 , 179 – 184 .
   Web of Science ®Google Scholar
• Gerbase , A.E. ; Gregorio , J.R. ; Martinelli , M. ; von Holleben , M.L.A. ; Jacobi , M.A.M. ; Freitas , L. ; Calcagno , C.I.W. ; Mendes , A.N.F. ; Pires , M.L. Polymers oxidation with VO(acac)2 complex . Catal. Today 2000 , 57 , 241 – 245 .
   Web of Science ®Google Scholar
• Martinez-mandez , S. ; Henriques , Y. ; Domingues , O. ; Ornelas , L.D. ; Krrentzien , H. Catalytic properties of silica supported titanium, vanadium and niobium oxide nanoparticles towards the oxidation of saturated and unsaturated hydrocarbons . Mol. Catal. A Chem. 2006 , 252 , 226 – 234 .
   Web of Science ®Google Scholar
• Swern , D. ; Billen , G.N. ; Findley , T.W. ; Scanlan , J.T. Hydroxylation of monounsaturated fatty materials with hydrogen peroxide . J. Am. Chem. Soc. 1945 , 67 , 1786 – 1789 .
   Web of Science ®Google Scholar
• Cameron , G.G. ; Duncan , A.W.S. Chemical modification of polydienes, 1. Grafting of chlorohydrinated polybutadiene and nitrile rubbers with poly (tetrahydrofuran) . Makromol. Chem. 1983 , 184 , 1153 – 1161 .
   Web of Science ®Google Scholar
• Cameron , G.G. ; Qureshi , M.Y. ; Rudin , A. Chemical modification of polydienes, 3 Copolymers. with polytetrahydrofuran by grafting-from butadiene polymers . Makromol. Chem. 1986 , 187 , 2763 – 2774 .
   Google Scholar
• Wang , Q. ; Zhang , X. ; Wang , L. ; Mi , Z. Epoxidation of hydroxyl- terminated polybutadiene with hydrogen peroxide under phase-transfer catalysis . J. Mol. Catal. A: Chem. 2009 , 309 , 89 – 94 .
   Web of Science ®Google Scholar
• Jian , X. ; Hay , A.S. Catalytic epoxidation of styrene-butadiene triblock copolymer with hydrogen peroxide . J. Polym. Sci. Polym. Chem. 1991 , 29 , 1183 – 1189 .
   Web of Science ®Google Scholar
• Antonietti , M. ; Forster , S. ; Hartmann , J. ; Oestriech , S. Novel amphiphilic block copolymers by polymer reactions and their use for solubilization of metal salts and metal colloids . Macromolecules 1996 , 29 , 3800 – 3806 .
   Web of Science ®Google Scholar
• Zuchowska , D. Polybutadiene modified by epoxidation. 1. Effect of polybutadiene microstructure on the reactivity of double bonds . Polymer 1980 , 21 , 514 – 520 .
   Web of Science ®Google Scholar
• Jian , X. ; Hay , A.S. Epoxidation of unsaturated polymers with hydrogen peroxide . J. Polym. Sci. Polym. Lett. 1990 , 28 , 285 – 288 .
   Web of Science ®Google Scholar
• Kachasakul , P. ; Assabumrungrat , S. ; Praserthdam , P. ; Pancharoen , U. Extractive reaction for epoxidation of cyclohexene to cyclohexene oxide using dioxirane in ketone/Oxone® system . Chem. Eng. J. 2003 , 92 , 131 – 139 .
   Web of Science ®Google Scholar
• Brown Ripin , D.H. ; Cai , W. ; Brenek , S.J. A safe, scaleable method for the oxidation of carbon–boron bonds with oxone . Tetrahedron Lett. 2000 , 41 , 5817 – 5819 .
   Web of Science ®Google Scholar
• Adam , W. ; Hadjiarapoglou , H.L. ; Nestler , B. Dimethyldioxirane epoxidation of α, β-unsaturated ketones, acids and esters . Tetrahedr. Lett. 1990 , 31 , 331 – 334 .
   Web of Science ®Google Scholar
• Aggarwal , V.K. ; Lopin , C.H. ; Sandrinelli , F. New insights in the mechanism of amine catalyzed epoxidation: dual role of protonated ammonium salts as both phase transfer catalysts and activators of oxone. J. Am. Chem. Soc. 2003, 125, 7596–7601.
   PubMed Web of Science ®Google Scholar
• Alavi Nikje , M.M. ; Rafiee , A. ; Haghshenas , M. Epoxidation of polybutadiene using in situ generated dimethyl dioxirane (DMD) in the presence of tetra-n-butyl ammonium bromide . Designed Monomers Polym. 2006 , 9 , 293 – 303 .
   Web of Science ®Google Scholar
• Alavi Nikje , M.M. ; Mozaffari , Z. 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 . J. Elastomers Plast. 2009 , 41 , 41 .
   Web of Science ®Google Scholar
• Erceg , M. ; Kovacic , T. ; Klaric , I. Poly(3-hydroxybutyrate) nanocomposites: Isothermal degradation and kinetic analysis . Thermochim. Acta. 2009 , 485 , 26 .
   Web of Science ®Google Scholar
• Akcelrud , L. ; Aguiar , M. ; Menezes , S.C.D. Configurational double bond selectivity in the epoxidation of hydroxy-terminated polybutadiene with m-chloroperbenzoic acid . Macromol. Chem. Phys. 1994 , 195 , 3937 – 3948 .
   Web of Science ®Google Scholar
• Gemmer , R.V. ; Golub , M.A. 13C-NMR spectroscopic study of epoxidized 1,4- polyisoprene and 1,4-polybutadiene . J. Polym. Sci. 1978 , 16 , 2985 – 2990 .
   Web of Science ®Google Scholar
• Roy , S. ; Gupta , B.R. ; De , S.K. Elastomer Technology Handbook . In: Cheremisinoff , N. P. , ed., CRC Press : FL , USA , 1993 , Chapter 17, 635–660.
   Google Scholar