阴非离子型Gemini表面活性剂合成及性能研究
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摘要
以马来酸酐、脂肪醇聚氧乙烯醚（AEO-3,AEO-5,AEO-7）、1,2-乙二醇，1,3-丙二醇，1,4-丁二醇、亚硫酸氢钠为原料，以自制的碳基固体酸为催化剂合成了系列阴-非离子型Gemini表面活性剂，并对各反应条件进行优化，利用红外光谱、~1H NMR等分析手段对各中间产物及目标产物进行结构表征，结果表明与目标产物相符。
表面性能研究结果表明：9种阴-非离子型Gemini表面活性剂在水溶液中胶束化过程是一个自发过程，主要来自熵驱动，温度升高不利于胶束化进行，且熵变对吉布斯自由能变的贡献有下降趋势，焓变的贡献也有增大趋势，在水溶液中胶束化存在焓熵补偿现象，补偿温度Tc均在307±2K范围，基本不随阴-非离子型Gemini表面活性剂的分子结构的改变而变化，随着Spacer或EO的增加形成胶束的能力与稳定性均提高，随着温度升高形成胶束的能力与稳定性均下降，Log cmc与Spacer length呈现出了很好的线性关系。
界面性能研究结果表明：9种阴-非离子型Gemini表面活性剂的最小烷烃碳数（nmin）,分别为：ANG3-Ⅳ-3，ANG5-Ⅳ-5，ANG7-Ⅳ-7的nmin分别为：10，13，13；ANG3-Ⅲ-3，ANG5-Ⅲ-5，ANG7-Ⅲ-7的nmin分别为：11，12，13；ANG3-Ⅱ-3，ANG5-Ⅱ-5，ANG7-Ⅱ-7的nmin分别为：10，11，11，与大庆采油一厂原油的45℃下油水界面张力，结果表明：部分ANG5-X-5，ANG7-X-7可以使大庆油水达到超低界面张力（10-3mN/m），与烷基苯磺酸盐复配体系界面性能结果表明：在ANG7-Ⅳ-7与C16-8MXS的复配比为2:1~3:1时，两者具有很好的复配作用，能够使大庆油水达到超低界面张力数量级(10~(-3)mN/m)，而在复配比为4:1~5:1时，复配体系能够使油水界面张力达到10~(-4)mN/m数量级。
泡沫性能研究结果表明：9种阴-非离子型Gemini表面活性剂起泡性能随着乙氧基（EO）结构单元增加，起泡性能逐渐增加，t1/2随着乙氧基（EO）结构单元增加逐渐增大，随着联接基链长的增加其起泡性能逐渐增大，t1/2随着联接基链长的增加而增加，随着盐浓度增加起泡性能先增加后降低，分别存在一个最佳盐浓度，NaCl最佳浓度为2%，CaCl_2最佳浓度为1g/L，t1/2随着浓度增加先增加后降低；随着温度增加其起泡性能先增加后减小，在50℃时达到最大，t1/2随着温度升高逐渐降低；随着醇浓度增加其起泡性能先增加后降低，并存在一个最佳醇浓度，乙醇为4mL/100mL，异丙醇为3mL/100mL，正丁醇为1mL/100mL，t1/2随着醇浓度增加先增加后降低。
乳化性能研究结果表明：9种阴-非离子型Gemini表面活性剂随疏水基及联接基碳数的增加，乳化性能变好；随着ANG7-Ⅳ-7与烷基苯磺酸盐（C16-8MXS）的复配比增大其乳化性能先增强后降低，在复配比为3：1时达到最大。考察了盐浓度对乳化性能的影响，结果表明：随着氯化钠浓度增加其乳化性能先小幅增加，后逐渐降低，在氯化钠浓度为2%时其乳化性能达到最大。考察了碱及碱浓度对乳化性能的影响，结果表明：随着NaOH，Na_2CO_3浓度增加，乳状液稳定性先增加后降低，在NaOH，Na_2CO_3浓度分别为2%和3%时，乳化性能达到最大，继续增加盐浓度乳状液稳定性变差。
增溶性能研究结果表明：9种阴-非离子型Gemini表面活性剂的增溶能力受增溶物的极性及结构影响显著，对苯、液体石蜡及正辛醇的增溶能力大小为：苯＞液体石蜡和正辛醇，随着联结基碳数增加其对苯的增溶能力先降低后升高，在联结基为1,3-丙二醇时增溶能力最差。
吸附性能研究结果表明：9种阴-非离子型Gemini表面活性剂吸附量与温度之间关系，结果表明：吸附量随温度的升高，逐渐减小，考察加入盐浓度对油砂表面吸附量的影响，结果表明：随着盐浓度增加其吸附量逐渐增加，加入Na2SO4的吸附量先增大后趋于平稳，总体吸附量要高于NaCl，在盐浓度为1g/L时达到平稳，考察碱浓度对吸附性能的影响，结果表明：表面活性剂ANG7-Ⅳ-7的浓度增加其在油砂表面吸附量逐渐增大，在活性剂浓度为2g/L时达到最大，继续增大浓度吸附量不再增加。
钙皂分散能力研究结果表明：9种阴-非离子型Gemini表面活性剂的钙皂分散指数远小于传统表面活性剂SDBS，这说明其具有较好的钙皂分散力，钙皂分散性能随该系列表面活性剂联结基碳数的增大而变好，随着联结基碳数增加其钙皂分散能力变好。
驱油性能研究结果表明：9种阴-非离子型Gemini表面活性剂驱岩心驱替实验表明，阴-非离子型Gemini表面活性剂可在水驱基础上提高原油采收率5%左右，随着氧乙烯结构单元的增加其表面活性剂驱提高原油采收率也越明显，对于相同氧乙烯结构单元的阴-非离子型Gemini表面活性剂，随着联结基碳数增加其表面活性剂驱提高原油采收率也越明显；三元驱岩心驱替实验表明，无论ANG7-Ⅳ-7弱碱或强碱三元复合驱体系，平均提高原油采收率均在20%左右，与目前用驱油用的烷基苯磺酸盐相当，与烷基苯磺酸盐复配使用也具有较好的驱油效率。
Base on maleic anhydride, fatty alcohol polyoxyethylene ether（AEO-3,AEO-5,AEO-7）1,2-ethylene glycol,1,3–propanediol1,4–butanediol and sodium bisulfite as materials.and with carbon based solid acid as catalyst synthesis of a series of anionic-nonionic GeminiSurfactants. And each of the reaction conditions were optimized structural characterizationresults show that the intermediate target products and finally products was confirmed by IRand1H NMR.
The surface performance results show that:9kinds of anionic-nonionic Geminisurfactants’micellization in solution is a spontaneous process mainly from the entropy-driven,and with the temperature increased micellization make against. And the entropy change of theGibbs free energy change contribution downward trend, Enthalpy change contributionincreasing trend, micellization in solution exist enthalpy-entropy compensation phenomenonand compensation temperature Tc is307±2K, do not change to change of the molecularstructure of anionic-nonionic Gemini surfactants, and with the spacer or EO increased themicellization capacity and stability was enhanced. and with temperature increased, themicellization capacity and stability was declined. between Log cmc and spacer length have agood linear relationship.
The interface result show that:9kinds of anionic-nonionic-Gemini surfactants have anminrespectively. ANG3-Ⅳ-3，ANG5-Ⅳ-5，ANG7-Ⅳ-7is10，13，13; ANG3-Ⅲ-3，ANG5-Ⅲ-5，ANG7-Ⅲ-7is11，12，13;ANG3-Ⅱ-3，ANG5-Ⅱ-5，ANG7-Ⅱ-7is10，11，11. Someof ANG5-X-5，ANG7-X-7can make daqing oil-water to achieve ultra-low interfacial tension(10~(-3)mN/m) at45℃. With alkyl benzene sulfonate complex system interface performanceresults show that: the ANG7-Ⅳ-7and C16-8MXS complex ratio at2:1~3:1, they have a goodcomplex performance. Make daqing oil-water to achieve ultra-low interfacial tension (10~(-3)mN/m) at45℃. And when complex ratio at4:1~5:1, the interfacial tension was reduce to10~(-4)mN/m.
Foaming performance results show that with the structural unit of ethoxy (EO) increasedthe foaming ability and the stability of foam（t1/2）increased too. With spacer length increasethe foaming ability was Strengthen. T1/2was increased; with the salt concentration increased,the foaming ability show increases at first and then decreases. Have an optimal saltconcentration. The optimal NaCl concentration is2%. The optimal CaCl2concentration is1g/L. With the salt concentration increase, t1/2shown increases at first and then decreases. With temperature increases foaming ability show increases at first and then decreases,maximum at50℃, t1/2decreases with the temperature increases. With the concentration ofalcohol increase, the foaming ability show increases at first and then decreases.
The emulsifying properties results show that: With the surfactants’hydrophobic group orthe carbon number of the spacer increases, the surfactants emulsifying properties turned good.With alkyl benzene sulfonate complex system emulsifying properties performance resultsshow that: with the ANG7-Ⅳ-7and C16-8MXS complex ratio increased emulsifyingproperties show increases at first and then decreases. The best complex ratio is3：1, the resultsof the effects of salt concentration on the emulsifying properties show that: with theconcentration of salt increased, emulsifying properties show increases at first and thendecreases, the optimal concentration of NaCl is2%; research on alkali and alkaliconcentration to the emulsifying properties the results show that: with the concentration of theNaOH，Na_2CO_3increased, emulsifying properties shown increased at first and then decreases.the optimal concentration of NaCl and Na_2CO_3is2%and3%respectively.
The solubilization results show that: the effect of solubilization capacity by polarity andstructure significantly for the9kinds of anionic-nonionic-Gemini surfactants. Therelationship of solubilization for benzene, liquid paraffin and n-octanol is benzene＞iquidparaffin and n-octanol. Of benzene solubilization ability with ethoxy increase in the numberwith the EO increase the ability of solubilization for benzene increase too. But with thecarbon number of spacer increased, the ability of solubilization for benzene decrease first andthen increased.
The adsorption performance results show that with temperature increase adsorptiongradually decreases, with the concentration of salt increase the absorption increase too. Theeffect of add Na_2SO_4has great influence on absorption then add NaCl, the optimalconcentration of salt is1g/L, and investigate the effect of add alkali on the absorption resultsshow that with the concentration of ANG7-Ⅳ-7increase the adsorption gradually increasingin the oil sands surface, maximum is2g/L, continue to increase the concentration of ANG7-Ⅳ-7the adsorption no longer increases.
The lime soap dispersion performance results show that9kinds ofanionic-nonionic-Gemini surfactants’ lime soap dispersion is much smaller than traditionalsurfactants SDBS, this results indicates that this series of surfactant have a good washingability. With the length of the carbon of alkyl chain and the spacer length increase the abilityof lime soap dispersion turned good.
Oil flooding performance results show that this series of anionic-nonionic-Geminisurfactants in enhanced oil recovery by more than11%on the basis of water flooding. Andwith the EO and spacer length increase the surfactant flooding enhance oil recovery turned more obvious. ASP flooding results show that ANG7-Ⅳ-7have a good a recovery by morethan20%in strong base or weak base system. And ANG7-Ⅳ-7have a good complex withalkyl benzene sulfonate in enhance oil recovery
表面性能研究结果表明：9种阴-非离子型Gemini表面活性剂在水溶液中胶束化过程是一个自发过程，主要来自熵驱动，温度升高不利于胶束化进行，且熵变对吉布斯自由能变的贡献有下降趋势，焓变的贡献也有增大趋势，在水溶液中胶束化存在焓熵补偿现象，补偿温度Tc均在307±2K范围，基本不随阴-非离子型Gemini表面活性剂的分子结构的改变而变化，随着Spacer或EO的增加形成胶束的能力与稳定性均提高，随着温度升高形成胶束的能力与稳定性均下降，Log cmc与Spacer length呈现出了很好的线性关系。
界面性能研究结果表明：9种阴-非离子型Gemini表面活性剂的最小烷烃碳数（nmin）,分别为：ANG3-Ⅳ-3，ANG5-Ⅳ-5，ANG7-Ⅳ-7的nmin分别为：10，13，13；ANG3-Ⅲ-3，ANG5-Ⅲ-5，ANG7-Ⅲ-7的nmin分别为：11，12，13；ANG3-Ⅱ-3，ANG5-Ⅱ-5，ANG7-Ⅱ-7的nmin分别为：10，11，11，与大庆采油一厂原油的45℃下油水界面张力，结果表明：部分ANG5-X-5，ANG7-X-7可以使大庆油水达到超低界面张力（10-3mN/m），与烷基苯磺酸盐复配体系界面性能结果表明：在ANG7-Ⅳ-7与C16-8MXS的复配比为2:1~3:1时，两者具有很好的复配作用，能够使大庆油水达到超低界面张力数量级(10~(-3)mN/m)，而在复配比为4:1~5:1时，复配体系能够使油水界面张力达到10~(-4)mN/m数量级。
泡沫性能研究结果表明：9种阴-非离子型Gemini表面活性剂起泡性能随着乙氧基（EO）结构单元增加，起泡性能逐渐增加，t1/2随着乙氧基（EO）结构单元增加逐渐增大，随着联接基链长的增加其起泡性能逐渐增大，t1/2随着联接基链长的增加而增加，随着盐浓度增加起泡性能先增加后降低，分别存在一个最佳盐浓度，NaCl最佳浓度为2%，CaCl_2最佳浓度为1g/L，t1/2随着浓度增加先增加后降低；随着温度增加其起泡性能先增加后减小，在50℃时达到最大，t1/2随着温度升高逐渐降低；随着醇浓度增加其起泡性能先增加后降低，并存在一个最佳醇浓度，乙醇为4mL/100mL，异丙醇为3mL/100mL，正丁醇为1mL/100mL，t1/2随着醇浓度增加先增加后降低。
乳化性能研究结果表明：9种阴-非离子型Gemini表面活性剂随疏水基及联接基碳数的增加，乳化性能变好；随着ANG7-Ⅳ-7与烷基苯磺酸盐（C16-8MXS）的复配比增大其乳化性能先增强后降低，在复配比为3：1时达到最大。考察了盐浓度对乳化性能的影响，结果表明：随着氯化钠浓度增加其乳化性能先小幅增加，后逐渐降低，在氯化钠浓度为2%时其乳化性能达到最大。考察了碱及碱浓度对乳化性能的影响，结果表明：随着NaOH，Na_2CO_3浓度增加，乳状液稳定性先增加后降低，在NaOH，Na_2CO_3浓度分别为2%和3%时，乳化性能达到最大，继续增加盐浓度乳状液稳定性变差。
增溶性能研究结果表明：9种阴-非离子型Gemini表面活性剂的增溶能力受增溶物的极性及结构影响显著，对苯、液体石蜡及正辛醇的增溶能力大小为：苯＞液体石蜡和正辛醇，随着联结基碳数增加其对苯的增溶能力先降低后升高，在联结基为1,3-丙二醇时增溶能力最差。
吸附性能研究结果表明：9种阴-非离子型Gemini表面活性剂吸附量与温度之间关系，结果表明：吸附量随温度的升高，逐渐减小，考察加入盐浓度对油砂表面吸附量的影响，结果表明：随着盐浓度增加其吸附量逐渐增加，加入Na2SO4的吸附量先增大后趋于平稳，总体吸附量要高于NaCl，在盐浓度为1g/L时达到平稳，考察碱浓度对吸附性能的影响，结果表明：表面活性剂ANG7-Ⅳ-7的浓度增加其在油砂表面吸附量逐渐增大，在活性剂浓度为2g/L时达到最大，继续增大浓度吸附量不再增加。
钙皂分散能力研究结果表明：9种阴-非离子型Gemini表面活性剂的钙皂分散指数远小于传统表面活性剂SDBS，这说明其具有较好的钙皂分散力，钙皂分散性能随该系列表面活性剂联结基碳数的增大而变好，随着联结基碳数增加其钙皂分散能力变好。
驱油性能研究结果表明：9种阴-非离子型Gemini表面活性剂驱岩心驱替实验表明，阴-非离子型Gemini表面活性剂可在水驱基础上提高原油采收率5%左右，随着氧乙烯结构单元的增加其表面活性剂驱提高原油采收率也越明显，对于相同氧乙烯结构单元的阴-非离子型Gemini表面活性剂，随着联结基碳数增加其表面活性剂驱提高原油采收率也越明显；三元驱岩心驱替实验表明，无论ANG7-Ⅳ-7弱碱或强碱三元复合驱体系，平均提高原油采收率均在20%左右，与目前用驱油用的烷基苯磺酸盐相当，与烷基苯磺酸盐复配使用也具有较好的驱油效率。
Base on maleic anhydride, fatty alcohol polyoxyethylene ether（AEO-3,AEO-5,AEO-7）1,2-ethylene glycol,1,3–propanediol1,4–butanediol and sodium bisulfite as materials.and with carbon based solid acid as catalyst synthesis of a series of anionic-nonionic GeminiSurfactants. And each of the reaction conditions were optimized structural characterizationresults show that the intermediate target products and finally products was confirmed by IRand1H NMR.
The surface performance results show that:9kinds of anionic-nonionic Geminisurfactants’micellization in solution is a spontaneous process mainly from the entropy-driven,and with the temperature increased micellization make against. And the entropy change of theGibbs free energy change contribution downward trend, Enthalpy change contributionincreasing trend, micellization in solution exist enthalpy-entropy compensation phenomenonand compensation temperature Tc is307±2K, do not change to change of the molecularstructure of anionic-nonionic Gemini surfactants, and with the spacer or EO increased themicellization capacity and stability was enhanced. and with temperature increased, themicellization capacity and stability was declined. between Log cmc and spacer length have agood linear relationship.
The interface result show that:9kinds of anionic-nonionic-Gemini surfactants have anminrespectively. ANG3-Ⅳ-3，ANG5-Ⅳ-5，ANG7-Ⅳ-7is10，13，13; ANG3-Ⅲ-3，ANG5-Ⅲ-5，ANG7-Ⅲ-7is11，12，13;ANG3-Ⅱ-3，ANG5-Ⅱ-5，ANG7-Ⅱ-7is10，11，11. Someof ANG5-X-5，ANG7-X-7can make daqing oil-water to achieve ultra-low interfacial tension(10~(-3)mN/m) at45℃. With alkyl benzene sulfonate complex system interface performanceresults show that: the ANG7-Ⅳ-7and C16-8MXS complex ratio at2:1~3:1, they have a goodcomplex performance. Make daqing oil-water to achieve ultra-low interfacial tension (10~(-3)mN/m) at45℃. And when complex ratio at4:1~5:1, the interfacial tension was reduce to10~(-4)mN/m.
Foaming performance results show that with the structural unit of ethoxy (EO) increasedthe foaming ability and the stability of foam（t1/2）increased too. With spacer length increasethe foaming ability was Strengthen. T1/2was increased; with the salt concentration increased,the foaming ability show increases at first and then decreases. Have an optimal saltconcentration. The optimal NaCl concentration is2%. The optimal CaCl2concentration is1g/L. With the salt concentration increase, t1/2shown increases at first and then decreases. With temperature increases foaming ability show increases at first and then decreases,maximum at50℃, t1/2decreases with the temperature increases. With the concentration ofalcohol increase, the foaming ability show increases at first and then decreases.
The emulsifying properties results show that: With the surfactants’hydrophobic group orthe carbon number of the spacer increases, the surfactants emulsifying properties turned good.With alkyl benzene sulfonate complex system emulsifying properties performance resultsshow that: with the ANG7-Ⅳ-7and C16-8MXS complex ratio increased emulsifyingproperties show increases at first and then decreases. The best complex ratio is3：1, the resultsof the effects of salt concentration on the emulsifying properties show that: with theconcentration of salt increased, emulsifying properties show increases at first and thendecreases, the optimal concentration of NaCl is2%; research on alkali and alkaliconcentration to the emulsifying properties the results show that: with the concentration of theNaOH，Na_2CO_3increased, emulsifying properties shown increased at first and then decreases.the optimal concentration of NaCl and Na_2CO_3is2%and3%respectively.
The solubilization results show that: the effect of solubilization capacity by polarity andstructure significantly for the9kinds of anionic-nonionic-Gemini surfactants. Therelationship of solubilization for benzene, liquid paraffin and n-octanol is benzene＞iquidparaffin and n-octanol. Of benzene solubilization ability with ethoxy increase in the numberwith the EO increase the ability of solubilization for benzene increase too. But with thecarbon number of spacer increased, the ability of solubilization for benzene decrease first andthen increased.
The adsorption performance results show that with temperature increase adsorptiongradually decreases, with the concentration of salt increase the absorption increase too. Theeffect of add Na_2SO_4has great influence on absorption then add NaCl, the optimalconcentration of salt is1g/L, and investigate the effect of add alkali on the absorption resultsshow that with the concentration of ANG7-Ⅳ-7increase the adsorption gradually increasingin the oil sands surface, maximum is2g/L, continue to increase the concentration of ANG7-Ⅳ-7the adsorption no longer increases.
The lime soap dispersion performance results show that9kinds ofanionic-nonionic-Gemini surfactants’ lime soap dispersion is much smaller than traditionalsurfactants SDBS, this results indicates that this series of surfactant have a good washingability. With the length of the carbon of alkyl chain and the spacer length increase the abilityof lime soap dispersion turned good.
Oil flooding performance results show that this series of anionic-nonionic-Geminisurfactants in enhanced oil recovery by more than11%on the basis of water flooding. Andwith the EO and spacer length increase the surfactant flooding enhance oil recovery turned more obvious. ASP flooding results show that ANG7-Ⅳ-7have a good a recovery by morethan20%in strong base or weak base system. And ANG7-Ⅳ-7have a good complex withalkyl benzene sulfonate in enhance oil recovery
引文
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