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trimethylamine : ウィキペディア英語版
trimethylamine

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Trimethylamine is an organic compound with the formula N(CH3)3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations. It is a gas at room temperature but is usually sold in pressurized gas cylinders or as a 40% solution in water.
Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the odor often associated with rotting fish, some infections, bad breath and can be a cause of vaginal odor due to bacterial vaginosis. It is also associated with taking large doses of choline and carnitine.
Trimethylamine is a nitrogenous base and can be readily protonated to give trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications.
==Production==
Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:〔A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 〕
:3 CH3OH + NH3 → (CH3)3N + 3 H2O
This reaction coproduces the other methylamines, dimethylamine (CH3)2NH and methylamine CH3NH2.
Trimethylamine has also been prepared via a reaction of ammonium chloride and paraformaldehyde, according to the following equation:
: 9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2

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