Aziridines
Abstract
The article contains sections titled:
1. |
Introduction |
2. |
Physical Properties |
3. |
Chemical Properties |
3.1. |
Homopolymerization |
3.2. |
Aziridine-Modified Polymers |
3.3. |
Polyfunctional Aziridines |
3.4. |
Miscellaneous |
4. |
Production |
4.1. |
The β-Chloroethylamine Process |
4.2. |
The Dow Process |
4.3. |
The Wenker Process |
4.4. |
Catalytic 2-Aminoethanol Dehydration Process |
5. |
Environmental Protection |
6. |
Uses |
7. |
Economic Aspects |
8. |
Toxicology and Occupational Health |
8.1. |
Ethylenimine |
8.2. |
Propylenimine |
8.3. |
Aziridine Derivatives and Polyethylenimines |
Aziridines are three-membered organic heterocycles which contain one nitrogen atom in the ring. All commercially available aziridine derivatives are made from ethylenimine (aziridine) and propylenimine (2-methylaziridine). Aziridines can undergo polymerization reactions, i.e., homopolymerization to form polyethyleneimines, or graft and copolymerization reactions to give aziridine-modified polymers. Polyfunctional aziridines are obtained by reaction of ethylenimine and propyleneimine and trifunctional arcylates. Ethylenimine and propylenime react with thiols and amines in ring-opening reactions, with oxiranes and isocyanates under preservation of the aziridine ring.
Ethylenimine is produced industrially by the β-chloroethylamine process, the Dow process, the Wenker process and the catalytic 2-aminoethanol dehydration process. Aziridines, polyethylenimines and aziridine-modified polymers are used primarily in the coatings, paper, water treatment, textile, and petroleum industries. Aziridines are highly toxic. Their toxicity probably results from alteration of nucleic acids, proteins, and other important biochemicals by alkylation. Substances derived from aziridines but no longer containing the aziridine ring, e.g., polyethyleneimines, are normally of low toxicity.