Triethyl benzyl ammonium chloride

Oxidation of indoles.5 Indoles react with K02 in conjunction with 18-crown-6 or benzyl(triethyl)ammonium chloride in THF to give products (1, 2, 3) that arise from an indoxyl hydroperoxide intermediate (a). 

Chloride ion in benzyl(triethyl)ammonium chloride can activate a nitrile group in dicyanomethylenedithiazole 42 which then cyclizes onto S-l to form the aromatic isothiazole ring and a new cyano group (Equation 17) <1997J(P1)3345>. The yield of isothiazole 86 is quantitative. 

Thiobenzophenone reacted in 20 min with dichlotocarbene, generated from chloroform and NaOH in the presence of benzyl(triethyl)ammonium chloride, in a two-phase system, to give 2,2-dichloro-3,3-diphenylthiirane in 80% yield (Equation 48) <1999HCA946>. 

AI3-14906 Ammonium, benzyltriethyl-, chloride Benzenemethanaminium, N,N,N-triethyl-, chloride Benzyl triethyl ammonium chloride Benzyltriethyl-ammonium chloride BTEAC EINECS 200-270-1 Sumquat 2355 TEAC TEBA TEBAC Triethyl-benzylammonium chloride N,N,N-Triethylbenzene-methanaminium chloride. Quaternary ammonium salt solvent for cellulose gelling Inhibitor in polyester resins intermediate In chemical manufxturing. Also used as a fibre dyeing auxilliary and phase transfer catalyst. Solid mp = 185° soluble in H2O (170 g/100 ml). Hexcel Janssen Chimica Zeeland Chem. Inc. 

In this paper we report experimental results on the kinetics of the polyaddition reaction in the melt and in solution (diglyme) using two different catalysts, namely tetrabutyl ammonium hydroxide (TBAH) and benzyl triethyl ammonium chloride (BTAC) at different temperatures. By simultaneous measurements of a, and in two cases we have also evaluated the critical branching parameters. 

Benzyl triethyl ammonium chloride (BTAC) as catalyst. 

When B is triethyl amine, a quaternary ammonium salt is formed. Since triethyl amine is volatile at the temperatures usually used for polyaddition, the catalyst would be depleted from the reaction mixture as the reaction progresses. In the case of a catalyst such as benzyl triethyl ammonium chloride, which would be expected to undergo thermal decomposition into benzyl chloride and triethyl amine, such a mechanism would predict why not only... 

Dichloromethane/aqueous NaOH 1.0 Benzyl triethyl ammonium chloride 1,2-Cyclododecanediol (50)... 

When the same procedure was employed adding 0.004 g (0.000019 mole) of benzyl triethyl ammonium chloride as a phase transfer catalyst in the reaction step, a white solid was obtained which dissolved in 5% aqueous sodium hydroxide and could not be reprecipitated. 

It is interesting to note that the very widely used Makosza catalyst , benzyl triethyl ammonium chloride, does not show high efficiency in this study. 4) Phosphonium ions are somewhat more effective and thermally stable than the corresponding ammonium catalysts and both are better than arsonium systems. 5) Substitution of the quaternary ion by alkyl rather than aryl groups yields more effective catalysts. 6) Reaction rates are generally greater in orf/io-dichlorobenzene (and presumably in other chlorocarbon media) than in benzene, and botli are better than heptane. In connection with this latter point, Ugelstad and coworkers have studied the reactions of quaternary ammonium phenoxide ions with alkyl halides in a variety of media and concluded that the... 

---