N,N'-双棕榈酰基对苯二胺二乙基磺酸钠的合成及性能
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摘要
以对苯二胺、棕榈酰氯、2-氯乙基磺酸钠为主要原料,经取代和酰化等反应合成了一种磺酸盐型双子表面活性剂——N,N'-双棕榈酰基对苯二胺二乙基磺酸钠(DS16-P-16),用FTIR、~1HNMR对中间体和目标产物进行了结构表征,并测定了其水溶性、表&界面活性、泡沫性能和乳化性能。结果表明:在25℃时,DS16-P-16的临界胶束浓度(CMC为5.01×10~(-4) mol/L)是传统表面活性剂十二烷基硫酸钠(SDS)的6.26%,pC20(水的表面张力降低20 mN/m时所需溶液浓度的负对数)为3.61,表现出更好的降低水表面张力的效率;随着温度和溶液浓度的增大,DS16-P-16溶液与吉林油田原油的界面张力逐渐降低,且均低于1×10~(-2) mN/m,在45℃下,质量分数为0.5%的该溶液可将油水界面张力降低至1.46×10~(-2) mN/m;在质量分数为0.1%时,DS16-P-16溶液的初始起泡高度为28 cm,稳泡率可达93%,乳状液稳定时间为437 s。相同条件下,质量分数为0.1%的十二烷基硫酸钠的初始起泡高度为15 cm,稳泡率为60%,乳化时间为128 s。
A sulfonate Gemini surfactant, N,N'-dipalmitoyl p-phenylenediamine diethyl sulfonate(DS16-P-16) was synthesized by substitution and acylation reaction using p-phenylenediamine, palmitoyl chloride and sodium 2-chloroethyl sulfonate as main raw materials. The intermediate and target product were identified by FTIR and ~1HNMR. The water solubility, surface/interfacial activity, foaming properties and emulsifying properties of DS16-P-16 were investigated. The results showed that the critical micelle concentration(CMC) of DS16-P-16 was 5.01×10~(–4) mol/L at 25 ℃, which was 6.26% of traditionalsurfactant sodium dodecyl sulfate(SDS), pC20(the negative logarithm of the concentration of DS16-P-16 solution required to reduce the surface tension of water by 20 mN/m) was 3.61, indicatedthat DS16-P-16 had a better ability to reduce water surface tension. With the increase of experimental temperature and solution concentration, the interfacial tension between DS16-P-16 solution and crude oil in Jilin oilfield gradually decreased, both were lower than 10~(–2) m N/m. At 45 ℃, 0.5%(mass fraction)DS16-P-16 solution could reduce the oil-water interfacial tension to 1.46×10~(–2) mN/m. The initial foaming height of 0.1% DS16-P-16 solution was 28 cm, the foam stabilization rate reached 93%, and the stable time of emulsion was 437 s.Under the same conditions, the initial foaming height of 0.1% SDS solution was only 15 cm, the foam stabilization rate was 60% and the emulsification time was 128 s.
A sulfonate Gemini surfactant, N,N'-dipalmitoyl p-phenylenediamine diethyl sulfonate(DS16-P-16) was synthesized by substitution and acylation reaction using p-phenylenediamine, palmitoyl chloride and sodium 2-chloroethyl sulfonate as main raw materials. The intermediate and target product were identified by FTIR and ~1HNMR. The water solubility, surface/interfacial activity, foaming properties and emulsifying properties of DS16-P-16 were investigated. The results showed that the critical micelle concentration(CMC) of DS16-P-16 was 5.01×10~(–4) mol/L at 25 ℃, which was 6.26% of traditionalsurfactant sodium dodecyl sulfate(SDS), pC20(the negative logarithm of the concentration of DS16-P-16 solution required to reduce the surface tension of water by 20 mN/m) was 3.61, indicatedthat DS16-P-16 had a better ability to reduce water surface tension. With the increase of experimental temperature and solution concentration, the interfacial tension between DS16-P-16 solution and crude oil in Jilin oilfield gradually decreased, both were lower than 10~(–2) m N/m. At 45 ℃, 0.5%(mass fraction)DS16-P-16 solution could reduce the oil-water interfacial tension to 1.46×10~(–2) mN/m. The initial foaming height of 0.1% DS16-P-16 solution was 28 cm, the foam stabilization rate reached 93%, and the stable time of emulsion was 437 s.Under the same conditions, the initial foaming height of 0.1% SDS solution was only 15 cm, the foam stabilization rate was 60% and the emulsification time was 128 s.
引文
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[19]Zhu Lili(祝丽丽),Kang Baoan(康保安),Yang Huiyan(杨卉艳),et al.Surface activity of sodium nonylphenol polyoxyethylenated propyl sulfonate and its application performance[J].Fine Chemicals(精细化工),2012,29(12):1176-1180.
[20]Sahar N,Andleeb Z N,Wajid H A,et al.Synthesis and investigation of surface active properties of counterion coupled gemini surfactants[J].Surfact Deterg,2014,17(3):409-417.
[2]Wang Yunfei(王云斐),Liu Yun(刘云).Progress in the synthesis of gemini surfactants[J].Fine Chemicals(精细化工),2004,21(2):98-103.
[3]Tsubone K,Arakawa Y,Rosen M J.Structural effects on surface and micellar properties of alkanediyl-α,ω-bis(sodium N-acyl-β-alaninate)gemini surfactants[J].J Colloid Interface Sci,2003,262(2):516-524.
[4]Kabir U D,Shafi M,Bhat P A,et al.Solubilization capabilities of mixtures of cationic Gemini surfactant with conventional cationic,nonionic and anionic surfactants towards polycyclic aromatic hydrocarbons[J].Journal of Hazardous Materials,2009,167(1):575-581.
[5]Zana R,Xia J.Gemini surfactants:synthesis,interfacial and solution-phase behavior,and applications[M].Marcel Dekker,2004:348.
[6]Murguia M C,Cristaldi M D,Porto A,et al.Synthesis,surface-active properties,and antimicrobial activities of new neutral and cationic trimeric surfactants[J].Journal of Surfactants&Detergents,2008,11(1):41-48.
[7]Asefi D,Mahmoodi N M,Arami M.Effect of nonionic co-surfactants on corrosion inhibition effect of cationic gemini surfactant[J].Colloids&Surfaces A:Physicochemical&Engineering Aspects,2010,355(1):183-186.
[8]Ye Zhiwen(叶志文),Lv Chunxu(吕春绪),Qian Hua(钱华).Synthesis and characterization of new quaternary ammonium gemini surfactants[J].Fine Chemicals(精细化工),2005,(S1):137-139.
[9]Wang Jun(王军),Li Junjian(李军舰),Chu Hongtao(初红涛),et al.Green synthesis of 2-substituted benzimidazoles by microwave irradiation[J].Chemical Research and Application(化学研究与应用),2013,(3):423-426.
[10]Su Yuhui(苏玉辉),Xu Xingzhi(许兴志),Song Jiying(宋吉英),et al.Microwave-assisted synthesis of o-hydroxybutyrophenone[J].Chemical Research and Application(化学研究与应用),2011,(4):483-485.
[11]Qin Wenlong(秦文龙),Liu Xuan(刘旋),Xiao Zengli(肖曾利),et al.Synthesis and properties of long-chain amido sulfonate type gemini surfactants[J].China Surfactant Detergent&Cosmetics(日用化学工业),2014,(1):6-9.
[12]Wang Jian(王健),Wu Yihui(吴一慧),Yan Zhanghong(严章宏),et al.Study on the determination of anionic active substances in fatty alcohol ether sulfate by two-phase titration[J].Contemporary Chemical Industry(当代化工),2018,47(2):282-285.
[13]Wang Liyan(王丽艳),He Xianyou(何显优),Bai Liming(白丽明),et al.Synthesis and properties of surfactants containing amine bond[J].Fine Chemicals(精细化工),2018,35(6):941-948.
[14]Song Qi(宋奇),Zhao Xiutai(赵修太),Wang Yanling(王彦玲),et al.Study on the effect of hydrophobic chain on gemini surfactants[J].Chemical Engineering of Oil&Gas(石油与天然气化工),2011,(3):266-270.
[15]Ma Xiping(马喜平),Jiao Wenchao(焦文超),Wang Xiaolei(王晓磊),et al.Synthesis and properties of anionic gemini surfactant GMAS-14[J].Oilfield Chemistry(油田化学),2015,(3):376-380.
[16]Li Gangsen(李刚森),Zhao Linxiu(赵林秀),Wang Peiyi(王培义),et al.Synthesis and surface activity of cationic gemini surfactant N,N?-bis(octadecyl/tetradecyl dimethyl)-1,2-dichloro-1,4-benzene dimethyl ammonium salt[J].Fine Chemicals(精细化工),2016,33(5):519-523.
[17]Kang Wanli(康万利),Meng Lingwei(孟令伟),Gao Huimei(高慧梅).Study on the interfacial tensions of the surfactants used for bi-component combination flooding[J].Chinese Journal of Colloid&Polymer(胶体与聚合物),2005,(4):23-25.
[18]Fan Yaxun(范雅珣),Han Yuchun(韩玉淳),Wang Yilin(王毅琳).Effects of molecular structures on aggregation behavior of gemini surfactants in aqueous solutions[J].Acta Physico-Chimica Sinica(物理化学学报),2016,32(1):214-226.
[19]Zhu Lili(祝丽丽),Kang Baoan(康保安),Yang Huiyan(杨卉艳),et al.Surface activity of sodium nonylphenol polyoxyethylenated propyl sulfonate and its application performance[J].Fine Chemicals(精细化工),2012,29(12):1176-1180.
[20]Sahar N,Andleeb Z N,Wajid H A,et al.Synthesis and investigation of surface active properties of counterion coupled gemini surfactants[J].Surfact Deterg,2014,17(3):409-417.