Phase-transfer catalyzed esterification of brominated poly(isobutylene-co- isoprene)

Industrial and Engineering Chemistry Research

Volumn 48, Issue 24, 2009, Pages 10759-10764

  McLean, J Keith ^a   Guillén Castellanos, Sergio A ^a   Parent, J Scott ^a   Whitney, Ralph A ^a   Kulbaba, Kevin ^b   Osman, Akhtar ^b  

^a QUEEN S UNIVERSITY   (Canada)

^b Lanxess Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BLEND COMPATIBILIZATION; CBR; DUAL ROLE; ESTER DERIVATIVES; ESTER SYNTHESIS; PHASE-TRANSFER CATALYSTS; TETRABUTYLAMMONIUM BROMIDE; TRANSFER TECHNIQUE;

BUTENES; CARBOXYLATION; CATALYSIS; CATALYSTS; ESTERS; ISOMERS; POLYBUTADIENES;

ESTERIFICATION;

EID: 73349142664     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie901284j     Document Type: Article

References (19)

1. Parent, J. S.; White, G. D. F.; Thom, D. J.; Whitney, R. A.; Hopkins, W. Sulfuration and Reversion Reactions of Brominated Poly-(isobutylene-co-isoprene. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1915-1926.
2. Guillén-Castellanos, S. A.; Parent, J. S.; Whitney, R. A. Synthesis of Ester Derivatives of Brominated Poly(isobutylene-co-isoprene): Solventfree Phase Transfer Catalysis. Macromolecules 2006, 39, 2514-2520.
3. Powers, K. W.; Wang, H. C.; Chung, T. C.; Dias, A. J.; Olkusz, J. A. Para-alkylstyrene/isoolefin Copolymers and Functionalized Copolymers Thereof. United States Patent 5,162,445, 1992.
4. Starks, C. M. Phase Transfer Catalysis. I. Heterogeneous Reactions Involving Anion Transfer by Quaternary Ammonium and Phosphonium Salts. J. Am. Chem. Soc. 1971, 93, 195-199.
5. Hennis, H. E.; Easterly, J. P.; Collins, L. R.; Thompson, L. R. Esters from the Reactions of Alkyl Halides and Salts of Carboxylic Acids. Ind. Eng. Chem. Prod. Res. Dev. 1967, 6, 193-195.
6. Nishikubo, T.; Iizawa, T.; Kobayashi, K.; Masuda, Y. Esterification reaction of poly[(chloromethyl)styrene] with salts of carboxylic acid using phase-transfer catalysts. Macromolecules 1983, 16, 722-727.
7. Landini, D.; Maia, A.; Montanari, F. Phase-transfer catalysis. Nucleophilicity of anions in aqueous organic two-phase reactions catalyzed by onium salts. A comparison with homogeneous organic systems. J. Am. Chem. Soc. 1978, 100, 2796-2801.
8. Wagenknecht, J. H.; Baizer, M. M.; Chruma, J. L. A Rapid Mild Esterification Method. Synth. Commun. 1972, 2, 215-219.
9. Frechet, J. M. J. Chemical Modification of Polymers Under Phase Transfer Conditions. J. Macromol. Sci.-Chem. 1981, A15, 877-890.
10. Ho, C. H.; Hopkins, W. Halogenated Butyl Rubber Graft Copolymers. United States Patent 5,264,494, 1993.
11. Parent, J. S.; Thom, D. J.; White, G.; Whitney, R. A.; Hopkins, W. Thermal Stability of Brominated Poly(isobutylene-co-isoprene). J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 2019-2026.
12. Pfeffer, P. E.; Silbert, L. S. Esterification by alkylation of carboxylate salts. Influence of steric factors and other parameters on reaction rates. J. Org. Chem. 1976, 41 (8), 1373-1379.
13. N2′ Mechanisms. J. Am. Chem. Soc. 1987, 109, 1773-1782.
14. Guillén-Castellanos, S. A.; Parent, J. S.; Whitney, R. A. Synthesis and Characterization of Ether Derivatives of Brominated Poly(isobutylene-co-isoprene). J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 983-992.
15. Asai, S.; Nakamura, H.; Tanabe, M.; Sakamoto, K. Distribution and Dissociation Equilibria of Phase-Transfer Catalysts, Tetrabutylammonium Salts. Ind. Eng. Chem. Res. 1993, 32, 1438-1441.
16. Yufit, S. S.; Zinovyev, S. S. A Comparative Study of Nucleophilic Subsitution under PTC Conditions in Liquid-Liquid and Solid-Liquid Systems. Tetrahedron 1999, 55, 6319-6328.
17. McLean, J. K.; Guillen-Castellanos, S. A.; Parent, J. S.; Whitney, R. A.; Resendes, R. Synthesis of Graft Copolymer Derivatives of Brominated Poly(isobutylene-co-isoprene. Eur. Polym. J. 2007, 43, 4619-4627.
18. Yamashita, S.; Kodama, K.; Ikeda, Y.; Kohjiya, S. Chemical Modification of Butyl Rubber. I. Synthesis and Properties of Poly(ethylene oxide)-Grafted Butyl Rubber. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2437-2444.
19. Ajji, A.; Utracki, L. A. Interphase and Compatibilization of Polymer Blends. Polym. Eng. Sci. 1996, 36, 1574-1585.