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Fig. 5-5 Polymerization of styrene by sodium naphthalene in 3-methyltetrahydrofuran at 20 C. After Schmitt and Schulz [1975] (by permission of Pergamon Press and Elsevier, Oxford).
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differences between kp and kp have been observed in polymerizations of methyl methacrylate (MMA), 2-vinylpyridine (2VP), and isoprene (IP) [Bywater, 1985; Jeuk and Muller, 1982; Van Beylen et al., 1988]. For reference, kp has values of 3:8 103 , 1:0 105 , and 2:0 103 L mol 1 s 1 for IP (25 C), 2VP (25 C), MMA ( 98 C), respectivley, all measured in THF [Bywater, 1985].
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Fig. 5-6 Polymerization of styrene by sodium naphthalene in 3-methyltetrahydrofuran at 20 C in the presence of sodium tetraphenylborate. After Schmitt and Schulz [1975] (by permission of Pergamon Press and Elsevier, Oxford).
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TABLE 5-11 Effect of Counterion on Anionic Polymerization of Styrenea; b Polymerization in Tetrahydrofuran K 107 kp kp 9 160 2.2 > > > > 80 1.5 = 60 80 0.8 6:5 104 > > > 50 80 0.1 > ; 22 0.02
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0.94 3.4 19.8 21.5 24.5
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Units of K are mol L 1 ; rate constants are L mol 1 s 1 . Data from Bhattacharyya et al. [1965a,b].
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The K values in Table 5-11 indicate that increased solvating power affects the reaction rate primarily through an increase in the concentration of free ions. When lithium is the counterion, one calculates from the equilibium constant that 1.5% of the propagating centers are free ions in THF (for a system where the total concentration of all propagating centers is 10 3 M) compared to zero in dioxane. Since free ions are so much more reactive than ion pairs, their small concentration has a very large effect on the observed polymerization rate. The majority of the propagation is carried by free ions; only about 10% of the observed reaction rate is due to ion pairs. It is worth mentioning that K values independently measured by conductivity are in excellent agreement with those obtained from the kinetic measurements. The K values from conductivity are 1.9, 1.5, 0.7, and 0:028 10 7 , respectively, for lithium, sodium, potassium, and cesium counterions [Geacintov et al., 1962; Shimomura et al., 1967a,b; Szwarc, 1969]. Table 5-11 shows that the dissociation constant for the ion pair decreases in going from lithium to cesium as the counterion. The order of increasing K is the order of increasing solvation of the counterion. The smaller Li is solvated to the greater extent and the larger Cs is the least solvated. The decrease in K has a very signi cant effect on the overall polymerization, since there is a very signi cant change in the concentration of the highly reactive free ions. Thus the free-ion concentration for polystyryl cesium (K 0:02 10 7 ) is less than 10% that of polystyryl lithium (K 10 7 ). The reactivities of the various ion pairs also increase in the same order as the K values: Li > Cs. The fraction of the ion pairs that are of the solvent-separated type increases with increasing solvation of the counterion. Solvent-separated ion pairs are much more reactive than contact ion pairs (Sec. 5-3d-4). The lower values of kp in dioxane relative to THF are also a consequence of the presence of a smaller fraction of the more reactive solventseparated ion pairs. The order of reactivity for the different ion pairs in dioxane is the reverse of that in tetrahydrofuran. Solvation is not important in dioxane. The ion pair with the highest reactivity is that with the weakest bond between the carbanion center and counterion. The bond strength decreases and reactivity increases with increasing size of counterion. However, the effect of increasing counterion size levels off after K as kp is approximately the same for potassium, rubidium, and cesium. The effect of counterion on ion-pair reactivity is dif ferent for methyl methacrylate (MMA) compared to styrene. The value of kp is 1 for lithium counterion and 30 33 for the larger alkali metal counterions for polymerization in tetrahydrofuran at 98 C [Jeuk and Muller, 1982; Szwarc, 1983]. The difference between lithium counterion and the larger counterions for MMA in THF is similar to that observed for styrene in dioxane. These results have been interpreted as indicating the absence of solvation by THF
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