Synthesis and properties of itaconic acid diester disulfonate Gemini surfactant

doi:10.16085/j.issn.1000-6613.2017-0075

Abstract

Abstract: A new type of Gemini surfactant(Gemini-12)was synthesized with cheap materials such as itaconic anhydride(IAn),lauryl alcohol,1,4-butanediol and sodium bisulfite by the monoesterification,sulfonation and diesterification reaction processes. The optimal reaction conditions of the diesterification obtained via orthogonal experiments were:ratio of sodium lauryl sulfoitaconic monoester to 1,4-butanediol=2.30:1.00,and 1.0% p-methyl benzenesulfonic acid at 150℃ for 6.0h. The structures of intermediate products and Gemini-12 were confirmed by FTIR and ¹H NMR. Finally,the primary physico-chemical properties of Gemini-12 were characterized. The critical micelle concentration(CMC)was 1.38×10^-3mol/L,and the surface tension at CMC was 28.60mN/m;the efficient factor pC₂₀ was 3.14;CMC/C₂₀ was 1.91;the saturation adsorption Γ_CMC was 1.15mmol/m²;the area per molecule at interface was 1.44×10^-3nm²/mole;the standard free energy of micellization was -9.018kJ/mol and the standard free energy of adsorption was -31.22kJ/mol. The CMC of Gemini-12 decreased with the increase of the concentration of NaCl solution.

Key words: itaconic anhydride, lauryl alcohol, sulfonation, esterification, surfactants, synthesis

摘要： 采用衣康酸酐、月桂醇、1，4-丁二醇、亚硫酸氢钠为主要原料，依次经单酯化、磺化、双酯化反应，合成了一种新颖的双子表面活性剂——1，4-丁二醇双衣康酸月桂醇双酯磺酸钠（Gemini-12），并通过正交试验对双酯化合成条件进行了优化。较佳工艺条件如下：双酯化反应温度150℃，反应时间6.0h，衣康酸单月桂醇酯磺酸钠与1，4-丁二醇的摩尔比为2.30：1.00，催化剂用量为物料总量的1.0%（质量分数）。通过FTIR和¹H NMR对中间产物和Gemini-12的结构进行了确认，并对终产物的物化性能进行了初步表征，测得其临界胶束浓度（CMC）为1.38×10^-3mol/L，表面张力γ_CMC为28.60mN/m，效率因子pC₂₀为3.14，表面活性剂的效能CMC/C₂₀为1.91，表面过剩量Γ_CMC为1.15mmol/m²，极限分子面积A_CMC为1.44×10^-3nm²/mol，标准胶束自由能△G_mic^Θ为-9.018 kJ/mol，标准吸附自由能△G_ads^Θ为-31.22 kJ/mol。随NaCl浓度的增加，Gemini-12的CMC值不断降低。

关键词: 衣康酸酐, 月桂醇, 磺化, 酯化, 表面活性剂, 合成

CLC Number:

TQ423.4

LI Pan, XU Hong, XIE Hongyu, ZHANG Huanhuan, DU Lei, XU Jun. Synthesis and properties of itaconic acid diester disulfonate Gemini surfactant[J]. Chemical Industry and Engineering Progress, 2017, 36(08): 3047-3052.

李盼, 徐红, 解鸿宇, 张欢欢, 杜蕾, 许军. 衣康酸双酯磺酸钠型双子表面活性剂的合成与性能[J]. 化工进展, 2017, 36(08): 3047-3052.

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