Insights into the Optimization of Alkyl Phenol/Alkyl Halide Ratio in Gemini Surfactant Synthesis

摘要

H-1 NMR and thin layer chromatography (TLC) were applied to analyze the component of two series of synthesized sulfonated Gemini surfactants with different spacer lengths (2, 4, and 6 carbons) and hydrophobic chain lengths (9, 12 carbons). Gemini surfactants were prepared by reacting alkylphenol with alkyl halide followed by sulfonation with chlorosulfonic acid. The influence of the molar ratio of alkyphenol to alkyl halide on the mono- to diether ratio was investigated and the results indicated that the molar ratio is a key factor to minimize impurities in the target material, due to the high reactivity of alkyl halide. In addition, the results showed that alkyl halide with a shorter spacer group length required a higher molar ratio of alkyl halide to alkylphenol. To synthesize the intermediate Gemini product with 80 % diether content, the molar ratios were optimized using n(alkylphenol):n(1,6-dibromohexane) = 1:0.55, n(alkylphenol):n(1,4-dibromobutane) = 1:0.7, and n(alkylphenol):n(1,2-dibromoethane) = 1:2.5, respectively.