Quaternary ammonium salts poisoning

The production of a quaternary ammonium salt from a tertiary amine and an alkyl halide forms the synthetic route to decamethonium, the first of a range of synthetic muscle relaxants having an action like the natural materials found in the arrow-poison curare. Decamethonium is actually a di-quaternary salt, as are more modem analogues, such as suxamethonium. Suxamethonium superseded decamethonium as a drug because it has a shorter and more desirable duration of action in the body. This arise because it can be metabolized by ester-hydrolysing enzymes (esterases) (see also Box 6.9). 

TiAl-Beta catalyst ion-exchanged with quaternary ammonium salts.1253 This is due to the selective poisoning of the acid sites without suppressing the oxidation activity of Ti sites. 

It is used as a methylating agent in the manufacture of many organic compounds, such as, phenols and thiols. Also, it is used in the manufacture of dyes and perfumes, and as an intermediate for quaternary ammonium salts. It was used in the past as a military poison. 

Trade Name Synonyms Catinal STB-70 [Toho Chem. Ind. http //www.toho-chem.co.jp], Zeonet B [Zeon http //www.zeon.co.jp, Zeon Europe http //www.zeon-europe.de] Steartrimonium chloride CAS 112-03-8 EINECS/ELINCS 203-929-1 Synonyms Ammonium, trimethyloctadecyl-, chloride Monostearyl trimethyl ammonium chloride Octadecyl trimethyl ammonium chloride Quaternium-10 STAC Stearyl trimethyl ammonium chloride N,N,N-Trimethyl-1 -octadecanaminium chloride Trimethyl octadecyl ammonium chloride Trimethyl stearyl ammonium chloride Classification Quaternary ammonium salt Empirical C21H46N Cl Formula [CH3(CH2)i6CH2N(CH3)3]"Cr Properties M.w. 348.13 cationic Toxicology LD50 (oral, mouse) 536 mg/kg, (skin, mouse) 1600 mg/kg poison by ing. mod. toxic by skin contact TSCA listed Hazardous Decomp. Prods. Heated to decomp., emits very toxic fumes of NOx, NH3, Cl"... 

Phase-transfer catalysts can also be poisoned by the presence of halides. Quaternary ammonium cations may form salts with iodide that is generated during reactions. Such salts do not partition well into aqueous phases, disrupting the catalytic phase-transfer cycling mechanism [39]. The presence and generation of iodide (and sometimes bromide) during PTC reactions should always be considered. 

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