The reaction of o-hydroxybenzyl alcohol with phenyl isocyanate has been investigated in different polar solvents with in situ FT-IR. The rate constants for the reactions of the phenolic hydroxyl group and the aliphatic hydroxyl group were calculated as k1 and k2, respectively. It is found that the phenolic hydroxyl group reacts more easily than the aliphatic hydroxyl group. It is also found that k1 increases with increasing solvent polarity, while the trend of k2 is the opposite. Moreover, the reaction kinetics is second-order with respect to toluene, butyl acetate, cyclohexanone and pyridine, but is first-order with respect to NMP and DMF without distinction for the two kinds of hydroxyl groups.
Zia KM Zuber M Bhatti IA Barikani M Sheikh MA (2009) Int J Biol Macromol 44: 23 .
Hernandez R Weksler J Padsalgikar A Choi T Angelo E Lin JS Xu LC Siedlecki CA Runt J (2008) Macromolecules 41: 9767 .
Coles SR Barker G Clark AJ Kirwan K Jacobs D Makenji K Pink D (2008) Macromole-Biosci 8: 526 .
Lee DK Yang ZD Tsai HB Tsai RS (2009) Polym Eng Sci 49: 2264 .
Erdodi G Kang J Kennedy JP Yilgor E Yilgor I (2009) J Polym Sci A 47: 5278 .
Lee YR Raghu AV Jeong HM Kim BK (2009) Macromol Chem Phys 210: 1247 .
Eceiza A Kortaberria G Gabilondo N Marieta C Corcuera MA Mondragon I (2005) Eur Polym J 41: 3051 .
Han JL Chern YC Hsieh KH Chiu WY Ma CCM (1998) J Appl Polym Sci 68: 121 .
Wang WS Wiggins JS (2008) J Appl Polym Sci 110: 3683 .
Nagata I Miyamoto K (1990) Fluid Phase Equilib 56: 203 .
Boufi S Belgacem MN Quillerou J Gandini A (1993) Macromolecules 26: 6706 .
Draye AC Tondeur JJ (1999) React Kinet Catal Lett 66: 319 .
Ephraim S Woodward AE Mesrobian RB (1958) J Am Chem Soc 80: 1326 .
Kothandaraman H Sultan Nasar A (1992) J Indian Chem Soc 69: 281.
Ramachandran PS Suru Z Frank NJ Vijay S Albert IY (2000) J Appl Polym Sci 77: 2212 .
Yang PF Li TD Li JY Zhu XW Xia YM (2010) Prog React Kinet Mech 35: 93 .
Oberth AE Bruenner RS (1969) Ind Eng Chem Fundam 8: 383 .