Isocyanate

Isocyanate is the functional group with the formula R–N=C=O. Organic compounds that contain an isocyanate group are referred to as isocyanates. An isocyanate that has two isocyanate groups is known as a di-isocyanate. Di-isocyanates are manufactured for reactions with polyols in the production of polyurethanes, a class of polymers.

Isocyanates should not be confused with cyanate esters and isocyanides, whose behaviors are very different. The cyanate (cyanate ester) functional group (R–O–C≡N) is arranged differently than the isocyanate group (R–N=C=O). Isocyanides have the connectivity R-N≡C, lacking the oxygen of the cyanate groups.

Isocyanates are produced by treating amines with phosgene:

These reactions proceed via the intermediacy of a carbamoyl chloride (RNHC(O)Cl). Owing to the hazards associated with phosgene, the production of isocyanates requires special precautions.

Isocyanates are electrophiles, and as such they are reactive toward a variety of nucleophiles including alcohols, amines, and even water. Upon treatment with an alcohol, an isocyanate forms a urethane linkage:

If a di-isocyanate is treated with a compound containing two or more hydroxyl groups, such as a diol or a polyol, polymer chains are formed, which are known as polyurethanes. Isocyanates react with water to form carbon dioxide:

This reaction is exploited in tandem with the production of polyurethane to give polyurethane foams. The carbon dioxide functions as a blowing agent.

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