Synthesis and structure characterization of diethyldiallylammonium chloride

Abstract

The unsaturated quaternary ammonium salt diethyladiallylammonium chloride(DEDAAC) was synthesized in a two-step synthetic method. The influences of the adding method of raw materials and temperature on the yields of diethylallylamine (DEAA), and drying and temperature on the synthesis of DEDAAC were investigated. The content of in-process product DEAA was determined by non-aqueous titration. The structure of product DEDAAC was identified with IR, ¹H NMR and elemental analysis. The results show that adding allyl chloride and sodium hydroxide alternately can increase the yield of DEAA and decrease by-products. In further synthesizing of DEDAAC from DEAA, the step of drying DEAA is very necessary. When DEAA is dried by solid sodium hydroxide, good columnar crystals with a high purity(mp 199.5–201.0 °C) are obtained; when DEAA is undried or the content of water in DEAA is above 2%, only platelets with bad quality are obtained even without crystals. The suitable synthesis conditions for DEAA and DEDAAC are 35 °C, 6 h and 40 °C, 36 h, respectively, and their yeilds are 69.7% and 67.3%, respectively.

Keywords

unsaturated quaternary ammoniun salt / diethylallylamine / diethyldiallylammonium chloride / diethylamine / allyl chloride / synthesis / characterization