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Isocyanates

Dear Reader,

We have had a lot to think about recent regarding polyurethane, so I think it is a good idea if we discuss the chemistry which is the basis of polyurethanes. The key chemicals for making polyurethanes are the isocyanates.

Now for those of you who have never encountered the isocyanates, I can tell you that they are rather reactive electrophiles which are often strong irritants. It is normal to make then from phosgene (carbonyl chloride) and a primary amine. They are similar to both carbon dioxide and the protein synthesis reagent (DCC, N,N’-Dicyclohexylcarbodiimide). All three have a sp carbon in an allene like system.

Using extended Huckel theory we can predict that carbon dioxide will have a charge of + 0.6 on the carbon, while diphenylcarbodiimide will have a charge of + 0.37 on the central sp carbon while the phenyl isocyanate will have a charge of + 0.46 on the central sp carbon. Here is a picture of phenyl isocyanate.

phenyl isocyanate space

Nucleophiles such as water, alcohol and amines will attack this carbon to form addition products. Here is a picture of phenyl isocyanate in which I have calculated the charges on the atoms, these are projected as colours onto the solvent accessable surface of the molecule. The more red they are then the more positive they are and the more blue then the more negative they are.

phenyl isocyanate charges

What you should be able to see is that the carbon in the isocyanate group is the most positive part of the molecule. I have a line drawing for you which will explain what happens when the molecule reacts with an alcohol, which is below.

urethane formation

In this way the isocyanate group can react with an alcohol group to form a bond between the alcohol molecule and the isocyanate molecule. The synthesis of polyurethane normally uses a diisocyanate and a long molecule which has two alcohol groups at the different ends of it. This will allow the creation of bigger and bigger molecules (polymerization) which transforms the small molecules into a very large molecule (a macromolecule).

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