壬基酚聚氧乙烯醚（10）衣康酸酯类表面活性剂的合成及表征
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摘要
以生物质衍生物—衣康酸替代石油化工原料—顺丁烯二酸酐合成阴离子表面活性剂,减少表面活性剂工业对石油资源的依赖,有利于可再生资源的循环利用。本文详细介绍了新型壬基酚聚氧乙烯醚(10)衣康酸酯类阴离子表面活性剂的合成方法,剖析了合成机理,并对其表面性能进行了研究;通过概述国内外研究进展及现状,阐明了产品广阔的应用前景。
以壬基酚聚氧乙烯醚(NPEO(10))、衣康酸(IA)和亚硫酸钠为原料,以浓硫酸为催化剂,通过酯化反应和磺化反应成功地合成了壬基酚聚氧乙烯醚(10)衣康酸单酯二钠盐(DNE(10)SIM)和壬基酚聚氧乙烯醚(10)衣康酸双酯钠盐(SNE(10)SID)新型阴离子表面活性剂。
系统地考察了反应温度、反应时间、物料摩尔比和催化剂用量对反应体系的影响。通过正交试验法确定了DNE(10)SIM和SNE(10)SID的最佳合成条件分别为:酯化反应温度为120℃和130℃,酯化反应时间为4h,n(NPEO(10)):n(IA)为1:1.05和3:1,催化剂用量为占衣康酸用量的6%和7%;磺化反应温度为90℃,磺化反应时间为4h,n(IA):n(Na2SO3)为1:1.05。
考察了两种阴离子表面活性剂的表面张力、临界胶束浓度、乳化性能和钙皂分散力,并与非离子表面活性剂壬基酚聚氧乙烯醚进行了比较。结果表明:在最佳合成条件下,DNE(10)SIM具有较低的表面张力和极低的临界胶束浓度,γCMC为35.45 mN/m,临界胶束浓度为1.77×10-6 mol/L,而SNE(10)SID的γCMC和临界胶束浓度分别为36.47 mN/m和5.42×10-5 mol/L ;SNE(10)SID具有较好的乳化性能;两种表面活性剂的钙皂分散力则与壬基酚聚氧乙烯醚相当。通过红外光谱(FTIR)和核磁共振光谱(1H NMR)进行产品结构分析,证明所得产品为目标产物。
Itaconic acid derived from the biomass ramification could be substituted for the maleic anhydride which was derived from the petrochemical materials. It was benefit for cyclic utilization of renewable resources and the dependence of surfactant industry on the oil would be reduced. In this paper, the method of the synthesis of sodium nonylphenol ethoxylate(10) sulfoitaconate esters anion surfactants were described in details and the synthetic mechanism was introduced. Meanwhile, the surface active of the anion surfantants were analyzed. Moreover, with discussing the status and development of the anion surfantants,it could be concluded that they had a broad application prospects.
With nonylphenol ethoxylate(10) ester, itaconic acid, sodium sulfite and concentrated sulfuric acid as the raw materials, a new type of sodium nonylphenol ethoxylate(10) sulfoitaconate ester surfactants, namely disodium nonylphenol ethoxylate(10) sulfoitaconate monoester (DNE(10)SIM) and sodium nonylphenol ethoxylate(10) sulfoitaconate diester (SNE(10)SID), were synthesized through the esterification and sulfonation reactions
The influence of the reaction temperature, reaction time, molar ratios of the materials and the dosage of analyst on the conversion were studied comprehensively. By the orthogonal test method to determine the optimum conditions: esterification reaction temperatures were 120℃and 130℃, reaction time were 4h, n(NPEO(10)):n(IA) were 1:1.05 and 3:1 and the dosage of concentrated sulfuric acid were 6% and 7%, respectively; sulfonation reaction temperature were 90℃, reaction time were 4h and n(IA):n(Na2SO3) were 1:1.05, respectively.
Comparing with the NPEO(10), the surface tension, critical micelle concentration, emulsification power and dispersing power of the new type of anion surfactants were investigated. The results indicated that: under the optimum conditions, DNE(10)SIM had low surface tension and the lowest critical micelle concentration. ItsγCMC was 35.45 mN/m and cmc was 1.77×10-6 mol/L. While, theγCMC and cmc of the SNE(10)SID were 36.47 mN/m and 5.42×10-5 mol/L, respectively; The emulsification power of SNE(10)SID was better than that of DNE(10)SIM. Compared with NPEO(10), both of them had ordinary dispersing power. The chemical structures of the prepared surfactants were confirmed by FTIR and 1H NMR.
以壬基酚聚氧乙烯醚(NPEO(10))、衣康酸(IA)和亚硫酸钠为原料,以浓硫酸为催化剂,通过酯化反应和磺化反应成功地合成了壬基酚聚氧乙烯醚(10)衣康酸单酯二钠盐(DNE(10)SIM)和壬基酚聚氧乙烯醚(10)衣康酸双酯钠盐(SNE(10)SID)新型阴离子表面活性剂。
系统地考察了反应温度、反应时间、物料摩尔比和催化剂用量对反应体系的影响。通过正交试验法确定了DNE(10)SIM和SNE(10)SID的最佳合成条件分别为:酯化反应温度为120℃和130℃,酯化反应时间为4h,n(NPEO(10)):n(IA)为1:1.05和3:1,催化剂用量为占衣康酸用量的6%和7%;磺化反应温度为90℃,磺化反应时间为4h,n(IA):n(Na2SO3)为1:1.05。
考察了两种阴离子表面活性剂的表面张力、临界胶束浓度、乳化性能和钙皂分散力,并与非离子表面活性剂壬基酚聚氧乙烯醚进行了比较。结果表明:在最佳合成条件下,DNE(10)SIM具有较低的表面张力和极低的临界胶束浓度,γCMC为35.45 mN/m,临界胶束浓度为1.77×10-6 mol/L,而SNE(10)SID的γCMC和临界胶束浓度分别为36.47 mN/m和5.42×10-5 mol/L ;SNE(10)SID具有较好的乳化性能;两种表面活性剂的钙皂分散力则与壬基酚聚氧乙烯醚相当。通过红外光谱(FTIR)和核磁共振光谱(1H NMR)进行产品结构分析,证明所得产品为目标产物。
Itaconic acid derived from the biomass ramification could be substituted for the maleic anhydride which was derived from the petrochemical materials. It was benefit for cyclic utilization of renewable resources and the dependence of surfactant industry on the oil would be reduced. In this paper, the method of the synthesis of sodium nonylphenol ethoxylate(10) sulfoitaconate esters anion surfactants were described in details and the synthetic mechanism was introduced. Meanwhile, the surface active of the anion surfantants were analyzed. Moreover, with discussing the status and development of the anion surfantants,it could be concluded that they had a broad application prospects.
With nonylphenol ethoxylate(10) ester, itaconic acid, sodium sulfite and concentrated sulfuric acid as the raw materials, a new type of sodium nonylphenol ethoxylate(10) sulfoitaconate ester surfactants, namely disodium nonylphenol ethoxylate(10) sulfoitaconate monoester (DNE(10)SIM) and sodium nonylphenol ethoxylate(10) sulfoitaconate diester (SNE(10)SID), were synthesized through the esterification and sulfonation reactions
The influence of the reaction temperature, reaction time, molar ratios of the materials and the dosage of analyst on the conversion were studied comprehensively. By the orthogonal test method to determine the optimum conditions: esterification reaction temperatures were 120℃and 130℃, reaction time were 4h, n(NPEO(10)):n(IA) were 1:1.05 and 3:1 and the dosage of concentrated sulfuric acid were 6% and 7%, respectively; sulfonation reaction temperature were 90℃, reaction time were 4h and n(IA):n(Na2SO3) were 1:1.05, respectively.
Comparing with the NPEO(10), the surface tension, critical micelle concentration, emulsification power and dispersing power of the new type of anion surfactants were investigated. The results indicated that: under the optimum conditions, DNE(10)SIM had low surface tension and the lowest critical micelle concentration. ItsγCMC was 35.45 mN/m and cmc was 1.77×10-6 mol/L. While, theγCMC and cmc of the SNE(10)SID were 36.47 mN/m and 5.42×10-5 mol/L, respectively; The emulsification power of SNE(10)SID was better than that of DNE(10)SIM. Compared with NPEO(10), both of them had ordinary dispersing power. The chemical structures of the prepared surfactants were confirmed by FTIR and 1H NMR.
引文
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