Aziridine

• Ethyleneimine
• Azacyclopropan

Colourless liquid with ammoniacal odor

Liquid

0.83 g · cm -3

-71 ° C

55 ° C.

213 hPa ( 20 ° C)

Miscible with water

Risk

For carcinogenic substances is generally no MAK value assigned ( class 2)

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Aziridine Azacyclopropan formally, is a chemical compound selected from the group of cyclic secondary amines. The common name also suggests a ethyleneimine but actually non-existent imine group ( H3CHC = NH) in the molecule.

Properties

Physical Properties

It is a colorless, water-soluble, highly mobile, volatile liquid of ammoniacal odor.

Chemical Properties

Aziridine is highly flammable and the vapors may form explosive mixtures with air. Small amounts of acids, acid-releasing compounds and already the normal carbon dioxide content of the air can lead also to some extent in stabilized products to a highly exothermic, explosive may polymerization.

Health Hazards

Aziridine acts acutely toxic by inhalation, ingestion and skin contact. Vapors are highly irritating to mucous membranes, excitation in the central nervous system and kidney- damaging. Acute symptoms are redness, blistering, and necrosis of the skin and mucous membranes, corneal opacity, bronchopneumonia, pulmonary edema and respiratory distress. Long term carcinogenicity is assumed. Increasingly, allergies are on aziridines detected ( type 1 and type 3 allergies: asthma, allergic rhinitis, allergic contact dermatitis and urticaria ). Monomer residues in the formulation to polyfunctional aziridines and PFAs itself can cause allergies.

Production

The first production in 1899 succeeded Willy Marckwald by treating β -halo amines with sodium hydroxide.

Aziridine is industrially produced by the dehydration of monoethanolamine in the gas phase over the modified zeolite ZSM5:

This method was further developed in the 1990s by Nippon Shokubai based on a previous method, which was invented in 1969.

Another method is the Wenker synthesis, is first esterified with the monoethanolamine with sulfuric acid and then treated with aqueous sodium hydroxide:

Derivatives and using

Aziridine can be polymerized to polyethylene imine, which is used as a wet strength and retention means for transfection, as precipitation reagent or (possibly after reaction with epichlorohydrin ) in papermaking.

Derivatives of aziridine such as mitomycin, and thiotepa triaziquone be used as alkylating cytostatic drugs for about 50 years for the treatment of cancers such as breast cancer, bladder cancer and ovarian cancer. The importance of these agents, however, has declined significantly since they have significant side effects.

Derivatives, polyfunctional aziridines (PFA) can be used as the crosslinking agent of water-soluble resins.