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Chapter 28: Problem 664

What commercial chemical reactions of terephthalic acid would be used to give a common polyester?

Short Answer

Expert verified
Terephthalic acid (C8H6O4) reacts with ethylene glycol (C2H6O2) in a condensation polymerization reaction to form polyethylene terephthalate (PET) through the formation of ester linkages (-CO-O-), while releasing water molecules. The chemical equation for this reaction is: \[n \ C_8H_6O_4 + n \ C_2H_6O_2 → [-C_6H_4(COOOC_2H_4OCOC_6H_4)-]_n + (2n-2) \ H_2O\] The physical and mechanical properties of PET are influenced by the degree of polymerization and the presence of ester linkages.

Step by step solution

01

Identify the reactants involved in the reaction

In this case, we will focus on the production of PET. The main reactants involved in the synthesis of PET are terephthalic acid (C8H6O4) from which the polyester's name is derived and ethylene glycol (C2H6O2).
02

Understand the main reaction mechanism

PET is synthesized using a condensation polymerization reaction, where the carboxylic acid group of terephthalic acid (-COOH) reacts with the alcoholic group of ethylene glycol (-OH), forming an ester linkage (-CO-O-) and releasing a water molecule in the process. This reaction is carried out at high temperatures and under specific catalyst conditions.
03

Write the chemical equation for the reaction

The balanced overall reaction for the synthesis of PET can be represented as follows: \[n \ C_8H_6O_4 + n \ C_2H_6O_2 → [-C_6H_4(COOOC_2H_4OCOC_6H_4)-]_n + (2n-2) \ H_2O\] Here, the square brackets represent the repeating unit in the PET polymer, and 'n' is the degree of polymerization, indicating the number of monomer units in the polymer chain.
04

Analyze the polymer properties

The physical and mechanical properties of PET are determined by the length of the polymer chain (degree of polymerization or molecular weight), as well as the presence of the ester linkage. The ester linkage contributes to the polymer's stability, strength, and resistance to heat and certain chemicals, making it suitable for various applications such as in clothing fibers, food packaging, and plastic materials.

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Most popular questions from this chapter

Write the structures for the following common polymeric materials: (a) Mylar (b) Polyurethan (c) Bakelite (d) Saran (e) Lucite (f) Orion

Outline all steps in a possible synthesis from non-polymeric starting materials of each of the following polymers. (a) Elastic fibers, used in girdles and bathing suits (Spandex, Lycra). (b) A polyester resin, used in making pipe, boats automobile bodies, etc.

Give an example of coordination polymerization. Name the chemists responsible for the discovery of this method of polymerization.

When formaldehyde is polymerized to a linear polymer in heptane solvent, with \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right){ }_{3} \mathrm{P}\) or a proton as a catalyst, it yields a thermally unstable material (A) that unzips readily to re-form formaldehyde. However, if the end of the polymer is 'capped", the product is a highly crystalline, tough polymer. The example below, \(\mathrm{B}\), is called Delrin and is already replacing nylon as a molding resin. Suggest a reason for the stability gained by capping the polymer.

Explain how natural rubber can be made durable for use in hot and cold weather.
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