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Chapter 29: Problem 14

Nomex, another aromatic polyamide (compare aramid), is prepared by polymerization of 1,3 -benzenediamine and the diacid chloride of 1,3 -benzenedicarboxylic acid. The physical properties of the polymer make it suitable for high-strength, hightemperature applications such as parachute cords and jet aircraft tires. Draw a structural formula for the repeating unit of Nomex.

Short Answer

Expert verified
Answer: The structural formula for the repeating unit of Nomex is: \[\ce{[-NH-}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-NH-C(O)}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-]}_{n}\]

Step by step solution

01

Identify the monomers

The two monomers in this case are 1,3-benzenediamine and the diacid chloride of 1,3-benzenedicarboxylic acid. The chemical structure of 1,3-benzenediamine is: \[\ce{NH2}\] \[\ce{-}\] \[{\begin{array}{c}\ce{C6H4}\end{array}}\] \[\ce{-}\] \[\ce{NH2}\] The chemical structure of diacid chloride of 1,3-benzenedicarboxylic acid is: \[\ce{Cl}\] \[\ce{-}\] \[{\begin{array}{c}\ce{C6H4}\end{array}}\] \[\ce{-}\] \[\ce{Cl}\]
02

Show polymerization reaction

During the polymerization process, the amine group (\[\ce{NH2}\]) from 1,3-benzenediamine reacts with one of the acid chloride groups (\[\ce{Cl}\]) from the diacid chloride of 1,3-benzenedicarboxylic acid, forming an amide bond. The reaction is as follows: \[\ce{NH2-}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-NH2 + Cl-}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-Cl -> [-NH-}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-NH-\] \[\ce{C(O)}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-Cl}]\]
03

Determine the repeating unit

The resulting polymer consists of alternating 1,3-benzenediamine and diacid chloride units connected by amide bonds (\[\ce{-NH-}\]). The structural formula for the repeating unit of Nomex is: \[\ce{[-NH-}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-NH-C(O)}\[{\begin{array}{c}\ce{C6H4}\end{array}}\]\ce{-]}_{n}\] Where n represents the number of repeating units in the polymer chain.

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Most popular questions from this chapter

Low-density polyethylene (LDPE) has a higher degree of chain branching than highdensity polyethylene (HDPE). Explain the relationship between chain branching and density.

At one time, a raw material for the production of hexamethylenediamine was the pentose-based polysaccharides of agricultural wastes, such as oat hulls. Treatment of these wastes with sulfuric acid or hydrochloric acid gives furfural. Decarbonylation of furfural over a zinc-chromium-molybdenum catalyst gives furan. Propose reagents and experimental conditions for the conversion of furan to hexamethylenediamine.

Draw a structural formula of the polymer resulting from base-catalyzed polymerization of each compound. Would you expect the polymers to be optically active? \((S)-(+)\)-lactide is the dilactone formed from two molecules of \((S)\) - \((+)\)-lactic acid.

Polymerization of 2-chloro-1,3-butadiene under Ziegler-Natta conditions gives a synthetic elastomer called neoprene. All carbon-carbon double bonds in the polymer chain have the trans configuration. Draw the repeat unit in neoprene.

We saw how intramolecular chain transfer in radical polymerization of ethylene creates a four-carbon branch on a polyethylene chain. What branch is created by a comparable intramolecular chain transfer during radical polymerization of styrene?
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