The polymerization of vinyl chloride
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Vinyl chloride is a monomer, which means it is a small molecule that can be combined with others to form a polymer. Show more…
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Use structural formulas and data from Table $12.6$ to write the chemical equation for the formation of a polymer of five monomer units from these monomers. (a) Vinylidene chloride, $\mathrm{H}_{2} \mathrm{C}=\mathrm{CCl}_{2}$ (b) Tetrafluoroethylene
Using structural formulas, show how vinyl chloride can polymerize to form three types of PVC polymers.
Polyvinyl chloride (PVC) is one of the most commercially important polymers (Table 12.5). PVC is made by addition polymerization of vinyl chloride $\left(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Cl}\right)$. Vinyl chloride is synthesized from ethylene $\left(\mathrm{C}_{2} \mathrm{H}_{4}\right)$ in a twostep process involving the following equilibria: Equilibrium 1: $\mathrm{C}_{2} \mathrm{H}_{4}(g)+\mathrm{Cl}_{2}(g) \rightleftharpoons \mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}(g)$ Equilibrium 2: $\quad \mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}(g) \rightleftharpoons \mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Cl}(g)+\mathrm{HCl}(g)$ The product of Equilibrium 1 is 1,2 -dichloroethane, a compound in which one $\mathrm{Cl}$ atom is bonded to each $\mathrm{C}$ atom. (a) Draw Lewis structures for $\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}$ and $\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Cl}$. What are the $\mathrm{C}-\mathrm{C}$ bond orders in these two compounds? (b) Use average bond enthalpies (Table 8.4) to estimate the enthalpy changes in the two equilibria. (c) How would the yield of $\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}$ in Equilibrium 1 vary with temperature and volume? (d) How would the yield of $\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Cl}$ in Equilibrium 2 vary with temperature and volume? (e) Look up the normal boiling points of 1,2 -dichloroethane and vinyl chloride in a sourcebook, such as the CRC Handbook of Chemistry and Physics. Based on these data, propose a reactor design (analogous to Figure 15.12) that could be used to maximize the amount of $\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Cl}$ produced by using the two equilibria.
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