Phase transfer catalyst benzyltriethyl ammonium

Anionicallv Activated Alumina. At this time we had also developed an interest in anionically activated alumina. These basic reagents were active in promoting alkylation(42), condensation(43) and hydrolysis(44) reactions. Thus, we impregnated alumina with sodium hydroxide and used this combination both with and without a phase transfer catalyst (benzyltriethyl ammonium chloride). When BTEAC was added, the conversion to ether was decreased and the formation of ester was noted. In the absence of a phase transfer catalyst, the ether became a minor product and methyl phenylacetate became the major product with coproduction of phenylacetic acid. This ester does not result from esterification of the acid as simple stirring of phenylacetic acid with Na0H/A1203 in methanol does not produce methyl phenylacetate. 

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. 

Uses Phase transfer catalyst chemical reagent Manuf./Distrib. Acros Org. http //www.acros.be] Amyl http //www.amyi.com] Lancaster Synthesis TCI Am. http //www.tciamerica.com] Yancheng Huaue Pharm. Chem. http //www.huayepharm. com Yixing Fangqiao East Chemical http //www. eastchemicais. com Benzyltriethyl ammonium chloride CAS 56-37-1 EINECS/ELINCS 200-270-1 Synonyms Ammonium, benzyltriethyl-, chloride Benzenemethanaminium, N,N,N-triethyl-, chloride BETEC BTEAC TEBAC N,N,N-Triethylbenzenemethanaminium chloride Triethyl benzyl ammonium chloride Classification Quaternary ammonium salt Empirical C13H22N Cl Formula C6H5CH2N(CI)(C2H5)3 Properties Solid m.w. 227.8 m.p. 197-199 C (dec.)... 

Phase-transfer catalysis. A Polish group reported that the Wittig-Horner reaction with a-phosphoryl sulfoxides, sulfones, and sulfides could be conducted in a two-phase system (aqueous NaOH-methylene chloride) with benzyltriethyl-ammonium chloride as catalyst. Later work showed that a catalyst was not necessary because these sulfur compounds themselves can function as catalysts for phase-transfer reactions. Thus (1) is an effective catalyst for alkylation of ketones by alkyl halides in the presence of 50% aqueous NaOH. Related, but somewhat less active, catalysts are sulfones such as (2), a-disulfoxides (3), and bisphosphonates (4). 

Phosphorylation of primary alcohols and phenols. Zwierzak has found that the Atherton-Todd phosphorylation can be carried out advantageously under phase-transfer eatalysis. Carbon tetrachloride and 50% aqueous sodium hydroxide serve as the solvent pair tetra-/i-butylammonium bromide or benzyltriethyl-ammonium chloride serve equally well as catalysts. Yields are 35 90% for primary alcohols and phenols low yields are obtained from other alcohols. 

---