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Chemistry

The breakdown of polystyrene is a quest many scientists have faced in recent years. Now more than ever before, there is an urgency to find a biological route to degrade polystyrene in an economical and environmentally safe way: the inability to do this is really the only downside of polystyrene as a useful material. We, the organic chemists, are responsible for coming up with reactions to breakdown or convert polystyrene into useful products. We are working alongside the biochemists and geneticists of the iGEM team to find a safe and useful way to break down polystyrene.

Our research into current chemical techniques did not show anything that we thought was any use, this suggested that we were entering new territory which was something that was exciting to know. Equipped with the knowledge from our first two years of studying chemistry and our problem solving skills gained along the way, we devised chemical syntheses to the breakdown and/or conversion of polystyrene. Below is our syntheses and we hope that they will help any researchers who wish to take the project further. Our aim was to use readily available chemicals and in abundance, this would make the whole process as cheap as possible. One of our sponsors, Styropack, converted polymers to biodegradable polylactic acids; we took this idea as our starting point for our research.

Mechanism Insight

Mechanism 1: This was our initial idea using knowledge of our sponsors work. We thought this decomposition would be easy. Then we realised our mistake! We were researching the wrong route. (Decomposing styrene, not polystyrene!)

Mechanism 2 and 3: Once we had conferred, we realised that these mechanisms would not be possible as a heterogeneous catalyst Palladium would not work in this reaction so we looked for a suitable homogeneous catalyst.

Mechanism 4: Out of the mechanisms we studied, this is by far the most promising. Despite this, there is still an urgent need to find an enzyme that can generate a reactive oxygen species. This must then react further to oxidise the benzyl carbon as well as degrade the remaining aliphatic chain.

Mechanism 5: This was an attempt at using transition metal chemistry to break the aliphatic chain of the hydrocarbon. It is a theoretical idea but one that paves the way for more creative methods.

Mechanism 1

The first mechanism shows the conversion of styrene (monomer of polystyrene) to lactic acid, which can be converted to polylactic acid, an more biodegradeable product. This mechanism involves the use of harsh and dangerous chemicals such as Pyridinium Chlorochromate and Chromic Acid. The first step shows how benzyne is formed, which is a carcinogen. This can be reduced to benzene and disposed of easily or stablised by a transition metal.

This route, though it may work for styrene, will not work for the breakdown of the polymer itself. But the conversion of the monomer unit into lactic acid is an important downstream step for making waste polystyrene useful.

Mechanism 2

The second mechanism shows that as polystyrene is heated up, the intermolecular forces weaken. Because benzene can undergo electrophilic aromatic substitution, it is treated with nitric acid to afford a new compound that contains a new Nitrogen Dioxide side group. The final product of this reaction is a benzene ring with an alcohol side group. We are still researching practical uses and possible further reactions on this line.

Mechanism 3

This is an alternative mechanism to that proposed in mechanism 2. Instead of adding an alcohol functional group, a Bromine group is added. Ultimately this results in the formation of an acid anhydride chain, which is degradable in the environment. The hydrocarbon chain would need to be both weakened and then broken so as to afford pure anhydride monomers which can be easily broken down.

The mechanism above, in combination with mechanism 5 below, may work to break down polystyrene into smaller parts.

Mechanism 4

This final mechanism draws on peroxyl product formation. Organic peroxyls are used in many chemical reactions in industry so it may be possible that this organic peroxyl will have a use in the near future.

This seems like a viable chemical route. Conversion of the product to a smaller unit of benzoyl peroxide will have pharmaceutical uses if it's possible. To add to the mechanism above, the use of a cytochrome P450 or a peroxidase may be able to generate a reactive oxygen species that will oxidise the benzyl carbon. Degradation of the aliphatic hydrocarbon chain may also be possible via mechanism 5.

Mechanism 5

The fifth mechanism shows how we might be able to degrade polystyrene by pursuing an inorganic method. This is an interesting concept as most chemical research today is influenced by inorganic chemistry. We believe the route below could serve as a template for future efforts to breakdown polystyrene. However key reagents are notably missing so we have left this open to further research.

Hazards and Safety

To conclude, this research has shown the team organic chemists that although there may not be a definite chemical route, we have researched widely and pitched in our ideas to inform how biological approaches could work. We are confident that in the near future that there will definetly be a cheap way to break down polystyrene that is both economical and safe. We set out to break down polystyrene completely and we have learnt much about the application of chemistry in synthesis.

References

Vincent N. Cavaliere, Marco G. Crestani, Balazs Pinter, Maren Pink, Chun-Hsing Chen, Mu-Hyun Baik, and Daniel J. Mindiola. Room Temperature Dehydrogenation of Ethane to Ethylene Journal of the American Chemical Society

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