Acrylonitrile in .NET

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CHAIN COPOLYMERIZATION
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TABLE 6-2 (Continued) M2 Methyl acrylate r1 0.84 0.07 3.6 2.8 0.4 0.80 6.4 4.4 0.17 0.2 0.36 0.46 9.0 2.4 0.14 0.04 0.27 0.14 0.35 8.3 1.8 90 42 15 1.8 3.4 0.24 0.030 M2 Acrylonitrile 1,3-Butadiene Butyl vinyl ether Maleic anhydride Methyl methacrylate Styrene Vinyl acetate Vinyl chloride 2-Vinylpyridine 4-Vinylpyridine Acenaphthylene Styrene Vinyl chloride Vinylidene chloride Acrylonitrile Maleic anhydride Methyl methacrylate Styrene Styrene Vinyl chloride Vinylidene chloride Ethyl vinyl ether Vinyl acetate Vinyl chloride Vinylidene chloride Ethyl vinyl ether Vinyl chloride Vinylidene chloride r2 1.5 1.1 0 0.012 2.2 0.19 0.03 0.093 1.7 1.7 1.1 0.52 0.07 0.36 0.03 0.08 0.48 1.2 0.29 0.1 0.55 0 0 0.01 0.13 0.26 1.8 4.7 T ( C) 50 5 60 75 50 60 60 50 60 60 60 60 68 60 75 60 60 60 60 70 70 80 60 60 60 60 60 68
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Data from Young [1975]; all other data from Greenley [1989a, 1999].
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TABLE 6-3 Relative Reactivities 1=r of Monomers with Various Polymer Radicalsa Polymer Radical Vinyl Vinyl Methyl Methyl Butadiene Styrene Acetate Chloride Methacrylate Acrylate Acrylonitrile 0.7 1.3 3.3 1.3 0.11 1.7 1.9 3.4 2.5 1.3 0.54 0.059 0.019 100 67 20 20 10 10 4.4 29 50 10 10 25 17 0.59 4 2.2 0.82 0.52 0.39 0.10 0.050 20 5.0 2 1.2 0.25 0.11 50 25 6.7 1.7 0.67 1.1 0.37 0.24
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Monomer 1,3-Butadiene Styrene Methyl methacrylate Methyl vinyl ketone Acrylonitrile Methyl acrylate Vinylidene chloride Vinyl chloride Vinyl acetate
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1=r values calculated from data of Table 6-2.
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TABLE 6-4 Rate Constants k12 for Radical Monomer Reactionsa
Monomer (M2) 2,060 1,130 515 422 268 52 26 41,800 10,045 4,180 2,510 2,090 520 230 98,000 49,000 13,100 1,960 1,310 720 230 230,000 154,000 46,000 23,000 10,100 2,300
Polymer Radical Methyl Methyl Vinyl 1,3-Butadiene Acrylonitrile Q e Styrene Acrylate Methyacrylate Vinyl Acetate Chloride 319,000 550,000 110,000 225,000 187,000 11,000 6,490 1.70 0.50 1.00 0.80 0.78 0.40 0.48 1.23 0.45 0.64 0.16 0.056 0.026 0.88
1,3-Butadiene Styrene Methyl methacrylate Acrylonitrile Methyl acrylate Vinyl chloride Vinyl acetate
100 70 130 330 130 11
280 165 314 413 215 9.7 3.4
k12 values calculated from data in Tables 3-11 and 6-3.
CHAIN COPOLYMERIZATION
of certain comonomer pairs. Table 6-3 and other similar data show that substituents increase the reactivity of a monomer toward radical attack in the general order
, Cl > CH CH2 > OCOR, CN, R > COR > OR, H COOH, COOR >
The order of monomer reactivities corresponds to the order of increased resonance stabilization by the particular substituent of the radical formed from the monomer. Substituents composed of unsaturated linkages are most effective in stabilizing the radicals because of the loosely held p-electrons, which are available for resonance stabilization. Substituents such as halogen, acetoxy, and ether are increasingly ineffective in stabilizing the radicals since only the nonbonding electrons on halogen or oxygen are available for interaction with a radical. The spread in the effectiveness of the various substituents in enhancing monomer reactivity is about 50 200-fold depending on the reactivity of the radical. The less reactive the attacking radical, the greater is the spread in reactivities of the different monomers. The effect of a second substituent in the 1-position as in vinylidene chloride is approximately additive. The order of radical reactivities can be obtained by multiplying the 1=r values by the appropriate propagation rate constants for homopolymerization (k11 ). This yields the values of k12 for the reactions of various radical monomer combinations (Table 6-4). The k12 values in any vertical column in Table 6-4 give the order or monomer reactivities as was the case for the data in Table 6-3. The data in any horizontal row give the order of radical reactivities toward a reference monomer. (The Q1 and e1 values in the last two vertical columns should be ignored at this point; they will be considered in Sec. 6-3b-4.) As with monomer reactivities it is seen that the order of radical reactivities is essentially the same irrespective of the monomer used as reference. The order of substituents in enhancing radical reactivity is the opposite of their order in enhancing monomer reactivity. A substituent that increases monomer reactivity does so because it stabilizes and decreases the reactivity of the corresponding radical. A consideration of Table 6-4 shows that the effect of a substituent on radical reactivity is considerably larger than its effect on monomer reactivity. Thus vinyl acetate radical is about 100 1000 times more reactive than styrene radical toward a given monomer, while styrene monomer is only 50 100 times more reactive than vinyl acetate monomer toward a given radical. A comparison of the self-propagation rate constants (kp ) for vinyl acetate and styrene shows that these two effects very nearly compensate each other. The kp for vinyl acetate is only 16 times that of styrene (Table 3-11). The interaction of radical reactivity and monomer reactivity in determining the rate of a radical monomer reaction can be more clearly seen by the use of the reaction coordinate diagram in Fig. 6-11. Figure 6-11 shows the potential-energy changes accompanying the radical monomer reaction as a function of the separation between the atoms forming the new bond. These energy changes are shown for the four possible reactions between resonance-stabilized and nonstabilized monomers and radicals