Synthesis And Structure-activity Relationship Of O-methyl-nonylphenol Sulfonates

A novel anionic gemini surfactant methylene bis(sodium sulfonated O-methyl- nonylphenol) (MBSMN) was synthesized in this thesis. The catalyst of phase transfer catalyzed O-methylation, technics conditions of sulofnation and the surface properties of products were investigated.The intermediate methylene bis (O-methyl-nonylphenol) (MBMN) was prepared by phase transfer catalyzed O-methylation of methylene dinonylphenol (MDN) using green reagent dimethyl carbonate (DMC) as methylating agent, from which a novel anionic gemini surfactant MBSMN was synthesized by followed sulfonation and neutralization. The other two surfactants, sodium sulfonated O-methyl-nonylphenol (SMN) and sodium sulfonated methylene bis (O-methyl- nonylphenol) (SMBMN) were also synthesized for investigate the structure-activity relationship of O-methyl-nonylphenol sulfonates. The structures of intermediate and three final products were recognized by IR spectrometry, mass spectrometry and 1H-NMR. In the monofactorial experiment, the catalyst of phase transfer catalyzed O-methylation was screened, with K2CO3 as catalyst and tetrabutyl ammonium bromide (TBAB) as phase transfer catalyst, the yield of MBMN can be up to at least 92% by HPLC. Optimum sulofnation conditions were obtained by orthogonal experiment, n(MBMN) : n(HSO3Cl) = 1 : 4, T=30℃and t= 9 h. It is found that the molar rate of purified MBSMN to hyamine 1622 is 1 : 1.72.The krafft point of SMN, SMBMN and MBSMN were below zero all. Air-Liquid surface tensions of the surfactants were investigated in this thesis at the temperature of 298 K. The surface tension and the critical micelle concentration (cmc) of MBSMN was 30.4 mN·m^-1and 0.407×10-3 mol·L^-1. The experimental results indicated that the surface tension of MBSMN is lower than the ordinary anionic surfactant linear alkylbenzene sulfonate (LAS), and cmc is about one order of magnitude lower than that. The experimental results of lime soap dispersing power(LSDP) and anti-hard water stability indicate that: LSDP of MBSMN is 33 %, is superior to 41 % of LAS, the anti-hard water stability of MBSMN is 749.4 ppm, is superior to 497.2 ppm of LAS. The experimental results of acid resistance, alkali resistance and salt tolerance indicate that: MBSMN can remain stable in the solution of salinity 4 % or alkalinity 0.5 mol·L^-1, it is superior to salinity 2 % or alkalinity 0.4 mol·L^-1of LAS. In addition, foaming ability, foam stability and emulsifying capacity were investigated. The experimental results indicate that MBSMN has good surface properties with LAS, SMN and SMBMN. It can be apply in related industries .