Question

A well-known company selling outdoor clothing has recently introduced jackets made of recycled polyethylene terephthalate (PET), the principal material in many soft drink bottles. Another company makes PET fibers by treating recycled bottles with methanol to give the diester dimethyl terephthalate and ethylene glycol and then repolymerizes these compounds to give new PET. Write a chemical equation to show how the reaction of PET with methanol can give dimethyl terephthalate and ethylene glycol.

Short answer

PET reacts with methanol to form dimethyl terephthalate and ethylene glycol through transesterification.

Step-by-step solution

Identify the Reactants

The reaction involves the polymer PET (polyethylene terephthalate) and methanol (CH₃OH) as the reactants. PET is composed of repeating units of ethylene glycol and terephthalic acid.

Understand the Structure of PET

PET is a polyester formed from ethylene glycol (C₂H₆O₂) and terephthalic acid (C₈H₆O₄). Its repeating unit is \[\begin{aligned}(& ext{-CO-C₆H₄-COO-CH₂-CH₂-O-})_n\end{aligned}\]where \( n \) represents the number of repeating units.

Analyze the Reaction with Methanol

The reaction with methanol (CH₃OH) involves breaking the ester linkages in PET to form dimethyl terephthalate (a diester) and ethylene glycol (an alcohol). Methanol helps in the transesterification process.

Write the Balanced Chemical Equation

The chemical equation for the reaction can be written as:\[\begin{aligned}(&\text{-CO-C₆H₄-COO-CH₂-CH₂-O-})_n + n \text{ CH₃OH} \rightarrow \& n \text{ COOCH₃-C₆H₄-COOCH₃ (dimethyl terephthalate)} + n \text{ HO-CH₂-CH₂-OH (ethylene glycol)}\end{aligned}\]This equation shows the conversion of ester bonds in PET to form dimethyl terephthalate and ethylene glycol.

Key concepts

Polyethylene Terephthalate (PET)

Polyethylene Terephthalate, widely known as PET, is an essential polyester polymer. It is frequently used in manufacturing everyday products, most notably beverage bottles. PET is synthesized through a chemical reaction between two main components: ethylene glycol and terephthalic acid.

• Ethylene glycol is a simple diol with two hydroxyl groups, contributing flexibility to the polymer.
• Terephthalic acid contains benzene rings, providing structural rigidity.

PET's ability to be recycled and repurposed into new materials is what makes it valuable for sustainability efforts. Recycling PET involves breaking it back down into its original monomers. This process conserves resources and reduces the environmental impact of plastic waste.

Transesterification

Transesterification is a vital chemical process often used in the recycling of polymers such as PET. In this process, an ester group in an organic compound is exchanged with another alcohol, producing a new ester.

• The reaction typically requires an alcohol (e.g., methanol) and a catalyst to proceed efficiently.
• Methanol helps break the existing ester bonds in PET, resulting in the formation of new ester compounds.

In the context of PET recycling, transesterification allows PET to be broken down into smaller compounds. This makes it possible to convert PET into other useful materials like fibers or films.

Dimethyl Terephthalate

Dimethyl terephthalate (DMT) is a diester formed during the transesterification of PET. It is an important intermediate chemical used in the production of polyester and other polymers.

• DMT is produced by esterifying terephthalic acid with methanol.
• The structure of DMT includes two methyl ester groups attached to a benzene ring.

DMT serves as a building block that can be repolymerized to manufacture fresh PET, showcasing the closed loop potential of PET recycling. It highlights how recycled PET can be returned to its original components and then rebuilt into new products.

Ethylene Glycol

Ethylene glycol is a vital compound obtained from the depolymerization of PET alongside dimethyl terephthalate. It is a basic organic molecule, features a simple two-carbon chain, and has two hydroxyl groups, making it a diol.

• Ethylene glycol is an important chemical in the creation of PET, contributing its flexibility and chemical structure.
• When PET undergoes transesterification, ethylene glycol is often one of the recovery products.

This compound is widely used in different industries beyond plastics, including as a coolant in automotive engines and a precursor for other chemical syntheses. Its recovery from PET highlights the effective reuse of resources in recycling techniques.