Synthesis and Aqueous Ozonation of Some Pyridinium Salts with Alkoxymethyl and Alkylthiomethyl Hydrophobic Groups

Abstract

The reaction of ozone with a number of pyridinium salts containing 1-alkoxymethyl and 1-alkylthiomethyl substituents was determined at a total substrate concentration of 2 g/L. Ozonation of pyridinium salts was strongly dependent on the kinds and positions of the substituents in the pyridine ring. The most favorable were the third position and the substituents including hydroxyl or dimethylamino groups. In an aqueous solution, 1-(alkoxymethyl)-3hydroxypyridinium, 1-(alkylthiomethyl)-3-hydroxypyridinium, and 1-(alkoxymethyl)-3-(dimethylamino)pyridinium salts reacted with ozone. The reaction was fast, and pyridinium salts were quantitatively removed. 1-(Alkoxymethyl)-and 1-(alkylthiomethyl)pyridinium chlorides were obtained by the Menschutkin reaction. In general, the procedure was simple and the reaction was productive and short. During the course of this study, we synthesized a new generation of cationic surfactants that were extremely reactive with ozone in an aqueous solution.

Biodegradation of ionic liquids – a critical review

“…Pyridinium ILs(109)(110)(111)(112) 68. 83 *Biodegradation values assessed by the CO 2 headspace test (ISO 14593).…”

Ionic Liquids: Methods of Degradation and Recovery

“…For this reason, chemical, photochemical or electrochemical oxidation have been put forward as processes for removing from wastewater both non-recoverable ILs and their degradation products (Czerwicka et al, 2009;Li et al, 2007;Pernak & Branicka, 2004;Siedlecka et al, 2008;Stepnowski & Zalewska, 2005;Stolte et al, 2008) (Fig.2.). Biological wastewater treatment is regarded as environmentally very friendly, and some examples of this process are given in this chapter.…”

“…Additionally, the ozonation products of 1-(tetradecyloxy)methylpyridinium chlorides substituted by a hydroxyl group in position 3 or 5 or containing a dimethylamino group in position 3, demonstrated no bacteriostatic or mycostatic effects. (Pernak & Branicka, 2004). These authors conclude that the products formed are less harmful than parent pyridinium compounds.…”

“…Information is available on ozonation (Pernak & Branicka, 2004), the Fenton reaction and Fenton-like reactions (Siedlecka et al, 2008a;Siedlecka et al, 2008b;). Ozonation of 1-(alkoxymethyl)-3-hydroxypyridinium, 1-(alkoxythiomethyl)-3-hydroxypyridinium and 1-(alkoxymethyl)-3-(dimethylamino)pyridinium chlorides was found to be rapid and effective.…”

Biodegradation of diesel fuel by a microbial consortium in the presence of 1-alkoxymethyl-2-methyl-5-hydroxypyridinium chloride homologues

“…Since the beginning of the twentieth century chemists have given considerable attention to design and synthesis of pyridinium chlorides or bromides because of their biocidal properties (Pernak et al 2001a, b;Pernak and Chwała 2003). Most of performed research on the toxicity of quaternary ILs was conducted with the use of single species (Pernak and Branicka 2004;Docherty and Kulpa 2005). This approach is fully justified because allows comparing chemicals, as well as microorganisms, to each other.…”