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This section provides an overview for aziridine as well as their applications and principles. Also, please take a look at the list of 2 aziridine manufacturers and their company rankings. Here are the top-ranked aziridine companies as of December, 2024: 1.Moltus Research Laboratories, 2.Menadiona.
Table of Contents
Aziridine is an organic compound with the chemical formula C2H5N.
It is also known as ethylene imine. The reaction of sodium hydroxide with β-aminoethyl sulfate yields aziridine. Industrially, aziridine can be produced from 1,2-dichloroethane and ammonia.
Aziridines share a common toxicity: they bind to nucleophiles, such as nucleobases in DNA, while opening the ring, leading to the mutagenicity of aziridines.
Aziridine is used in the manufacture of adhesives, fiber treatment agents, raw materials for polyethyleneimine, agricultural chemicals, and ion exchange resins. However, exposure of aziridine to skin and mucous membranes is highly toxic to the human body. Because of its toxic nature, it should be handled with care.
Aziridine compounds with aziridine groups are marketed as chemitites. This chemitite is used as a cross-linking agent in paints, adhesives, and coatings.
Aziridine has a melting point of -77.9°C and a boiling point of 55-56°C. It is a colorless, clear liquid. Aziridine has a characteristic ammonia-like odor.
Aziridine has an acid dissociation constant of 7.9 and is less basic than linear aliphatic amines.
Aziridine has a three-membered ring structure; it is a hetero three-membered ring compound consisting of one nitrogen atom and two carbon atoms. It has a molecular weight of 43.07 and a density of 0.8321 g/ml at 20°C.
Like cyclopropane and ethylene oxide, it is angularly strained. This is because the bond angle of the atoms in aziridine is approximately 60°, much smaller than the 109.5° that normal hydrocarbons have.
The bonding of these compounds can be explained using the banana bent bond model. That is, covalent bonds in the shape of a banana.
The bond angle of aziridine provides a high enough barrier to invert the nitrogen atom so that the trans and cis forms of N-chloro-2-methylaziridine can be separated.
Aziridines can be synthesized from haloamines by intermolecular nucleophilic substitution reactions of halogens with adjacent amino groups. Similar reactions can proceed with amino alcohols if the hydroxy group is converted to a superior leaving group. The cyclization of haloamines is called the Gabriel Ethylenimine Method, while the cyclization of amino alcohols is called the Wenker synthesis.
Aziridine can be synthesized by the addition of nitrenes produced by photolysis or thermal decomposition of azides to alkenes. Aziridine is also formed when a triazoline obtained by cycloaddition of an azide with an alkene is pyrolyzed or photolyzed to liberate a nitrogen atom.
Furthermore, ring-opening of epoxides in the presence of sodium azide and removal of the nitrogen atom by reduction with triphenylphosphine also yields aziridine.
Aziridine rings, which are highly sterically strained, undergo ring-opening reactions with nucleophiles. When amines, alcohols, and thiols are added to aziridines, aminoethylation products can be formed. Gilman reagent and alkyl lithium are also effective nucleophiles.
Ring-opening reactions have also been applied to the asymmetric synthesis of oseltamivir using trimethylsilyl azides and asymmetric ligands.
Aziridines produce a wide variety of polymer derivatives called polyethyleneimines (PEIs). Polyethyleneimine is useful as a cross-linker and a precursor for coatings.
*Including some distributors, etc.
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Menadiona, established in 1970 and headquartered in Barcelona, Spain, is a manufacturer specializing in the production of special chemicals such as aziridine and its derivatives, crosslinkers, and chemical intermediates. The company's main product line includes 2-Aminoethil diisopropylamine, Hydroxypivalic Acid (HPA), EI derivatives, PI derivatives, 2-Methyl Aziridine, and more. These products serve various industries, including the pharmaceutical, veterinary, plant health, nutraceutical, and others. The company also offers services, including contract development and full contract manufacturing for APIs, advanced intermediates, starting materials, and industrial products.
Moltus Research Laboratories, established in 2014 and headquartered in Thane, Maharashtra, is a manufacturer, exporter, and supplier of quality pharmaceutical chemicals. The company offers a diverse product portfolio, including 1-Thiocarbonyldiimidazole Naphthalene, 2,6-dimethylphenyl Isothiocyanate, Benzyl Isothiocyanate, methyl 6-methyl nicotinate, benzoyl isothiocyanate, and various other compounds. These products have wide-ranging applications, such as aiding in the formulation of medicines, activating carboxylic acids in organic synthesis, contributing to cosmetic product manufacturing, participating in the formation of thioureas, and being studied for potential biological activities in various industrial sectors.
Ranking as of December 2024
Derivation Method| Rank | Company | Click Share |
|---|---|---|
| 1 | Moltus Research Laboratories |
58.1%
|
| 2 | Menadiona |
41.9%
|
Derivation Method
The ranking is calculated based on the click share within the aziridine page as of December 2024. Click share is defined as the total number of clicks for all companies during the period divided by the number of clicks for each company.Number of Employees
Newly Established Company
Company with a History
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
Spain
|
1 | 50.0% |
|
India
|
1 | 50.0% |
