Oxygen-Containing Quaternary Phosphonium Salts (oxy-QPSs): Synthesis, Properties, and Cellulose Dissolution

Abstract

In the present study, the synthesis of oxygen-containing quaternary phosphonium salts (oxy-QPSs) was described. Within this work, structure–property relationships of oxy-QPSs were estimated by systematic analysis of physical–chemical properties. The influence of the oxygen-containing substituent was examined by comparing the properties of oxy-QPSs in homology series as well as with phosphonium analog-included alkyl side chains. The crystal structure analysis showed that the oxygen introduction influences the conformation of the side chain of the oxy-QPS. It was found that oxy-QPSs, using an aprotic co-solvent, dimethylsulfoxide (DMSO), can dissolve microcrystalline cellulose. The cellulose dissolution in oxy-QPSs appeared to be dependent on the functional group in the cation and anion nature. For the selected conditions, dissolution of up to 5 wt% of cellulose was observed. The antimicrobial activity of oxy-QPSs under study was expected to be low. The biocompatibility of oxy-QPSs with fermentative microbes was tested on non-pathogenic Saccharomyces cerevisiae, Lactobacillus plantarum, and Bacillus subtilis. This reliably allows one to safely address the combined biomass destruction and enzyme hydrolysis processes in one pot.

Keywords

• oxygen-containing quaternary phosphonium salts
• melting point
• crystal structure
• cellulose dissolution
• antimicrobial properties
• toxicity