一种pH响应性氨基酸酸液起泡剂的合成与应用
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摘要
以十二胺和甲基丙烯酸甲酯为原料,通过两步反应合成了一种pH响应性氨基酸两性表面活性剂——N-月桂基-(α-甲基)-β-氨基丙酸钠(AAS-1)。采用单因素实验进行了反应条件优化,得出最优工艺条件为:n(十二胺)∶n(甲基丙烯酸甲酯)=1.0∶1.4,反应温度为60℃,反应时间为10 h。以同样的方法合成了表面活性剂N-月桂基-β-氨基丙酸钠(AAS)作对比实验。采用FTIR和~1HNMR对产物结构进行了表征,用表面张力仪测定了不同pH下AAS和AAS-1的表面张力,得出表面张力曲线,并着重考察了α-烷基对AAS-1表面活性的影响。用WaringBlender法对AAS和AAS-1在不同pH下的泡沫性能进行了测定。结果表明:AAS和AAS-1均具有pH响应性。受α-烷基的影响,pH<7时,AAS-1的泡沫体积(V_0)最高可达523 mL,泡沫半衰期(t_(1/2))最高可达6.25 min;pH>7时,AAS-1的V_0<185 mL,t_(1/2)<0.58 min,说明AAS-1在酸性水介质中,起泡能力强,泡沫稳定性好;在碱性水介质中却可迅速消泡,与AAS的发泡规律恰好相反,且能反复起泡消泡,可用于泡沫酸液体系中充当起泡剂。
A pH-responsive amino acid amphoteric surfactant, N-lauryl-(α-methyl)-β-aminopropionate(AAS-1) was synthesized by two-step reaction using dodecylamine and methyl methacrylate as raw materials. The synthesis conditions were optimized by single factor experiments. The optimal synthesis conditions were obtained as follows: molar ratio of dodecylamine to methyl methacrylate was 1.0∶1.4,reaction temperature was 60 ℃, and reaction time was 10 h. For comparison, N-lauryl-β-aminopropionate(AAS) was prepared in the same way. The structures of products were characterized by FTIR and ~1HNMR.The surface tensions of AAS and AAS-1 at different pH were measured by surface tension meter, and the surface tension curves were achieved. Furthermore, the effect of α-alkyl on the surface activity of AAS-1 was investigated. Foam properties of AAS and AAS-1 at different pH were tested by Waring Blender method. The results showed that both AAS and AAS-1 had pH responsiveness. Due to the influence ofα-alkyl, when pH<7, AAS-1 had a foam volume(V_0) of up to 523 mL and a foam half-life(t_(1/2)) of up to6.25 min, but when pH>7, V_0<185 m L, t_(1/2)<0.58 min. This means that, in the acidic aqueous medium,AAS-1 has good foaming ability and good foam stability but can exhibit quick defoaming ability in alkaline water medium, which shows the opposite of AAS foaming regularity. Thus, ASS-1 can be used as foaming agent in the foamed acid system and can be repeatedly foamed and defoamed.
A pH-responsive amino acid amphoteric surfactant, N-lauryl-(α-methyl)-β-aminopropionate(AAS-1) was synthesized by two-step reaction using dodecylamine and methyl methacrylate as raw materials. The synthesis conditions were optimized by single factor experiments. The optimal synthesis conditions were obtained as follows: molar ratio of dodecylamine to methyl methacrylate was 1.0∶1.4,reaction temperature was 60 ℃, and reaction time was 10 h. For comparison, N-lauryl-β-aminopropionate(AAS) was prepared in the same way. The structures of products were characterized by FTIR and ~1HNMR.The surface tensions of AAS and AAS-1 at different pH were measured by surface tension meter, and the surface tension curves were achieved. Furthermore, the effect of α-alkyl on the surface activity of AAS-1 was investigated. Foam properties of AAS and AAS-1 at different pH were tested by Waring Blender method. The results showed that both AAS and AAS-1 had pH responsiveness. Due to the influence ofα-alkyl, when pH<7, AAS-1 had a foam volume(V_0) of up to 523 mL and a foam half-life(t_(1/2)) of up to6.25 min, but when pH>7, V_0<185 m L, t_(1/2)<0.58 min. This means that, in the acidic aqueous medium,AAS-1 has good foaming ability and good foam stability but can exhibit quick defoaming ability in alkaline water medium, which shows the opposite of AAS foaming regularity. Thus, ASS-1 can be used as foaming agent in the foamed acid system and can be repeatedly foamed and defoamed.
引文
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[2]Liu Junhai(刘军海).Synthesis and application of N-dodecyl-β-aminopropionic acid surfactant[J].China Cleaning Industry(中国洗涤用品工业),2008,8(3):45-46.
[3]Yu Xuejun(余学军),Xu Danlu(徐丹鲁),Zheng Quan(郑全).Synthesis and performance testing of N-dodecyl-β-aminopropionate[J].Fine Chemicals(精细化工),1996,13(6):16-17.
[4]Wang Jie(王杰),Bo Chunling(薄纯玲),Wang Shuyu(王淑钰),et al.Progress of amino acid surfactants[J].China Cleaning Industry(中国洗涤用品工业),2018,18(6):61-68.
[5]Shi Yingying(石莹莹).Research progress in the properties and application of N-acylamino acid surfactants[J].Henan Chemical Industry(河南化工),2016,33(2):16-18.
[6]Kong Yuming(孔玉明),Luo Yue(罗跃),Ren Zhaohua(任朝华),et al.Progress in the synthesis of amino acid amphoteric surfactants[J].Chemistry&Bioengineering(化学与生物工程),2012,29(3):9-12.
[7]Du Yongfeng(杜永峰),LüFang(吕方).Synthesis of N-dodecyl alanine[J].China Surfactant Detergent&cosemetics(日用化学工业),2000,30(5):65-66.
[8]Lan Yunjun(兰云军),Bao Lihong(鲍利红).Synthesis of N-alkyl-β-aminopropionic acid[J].Leather and Chemical Industry(皮革与化工),2002,19(2):21-23.
[9]Zhao Xiaodong(赵晓东),Li Jufeng(李巨峰).Synthesis and foaming properties of N-alkyl-β-aminopropionic acid amphoteric surfactants[J].China Surfactant Detergent&Cosemetics(日用化学工业),1998,28(6):9-13.
[10]Shui Lingling(水玲玲),Zheng Liqiang(郑利强),Zhao Jianxi(赵剑曦),et al.Study on the interfacial activity of Gemini surfactant system[J].Fine Chemicals(精细化工),2001,18(2):67-69.
[11]Yu Xuexing(俞雪兴),Wu Jingfeng(吴京峰),Tan Longmei(谈龙妹),et al.Synthesis and application of amino acid fluorocarbon surfactants[J].Fine Chemicals(精细化工),2008,25(6):569-572.
[12]Jiang Z,Li X,Yang G,et al.pH-responsive surface activity and solubilization with novel pyrrolidone-based Gemini surfactants[J].Langmuir the Acs Journal of Surfaces&Colloids,2012,28(18):7174.
[13]Wang Jun(王军),Chen Yufei(陈玉菲),Li Nini(李妮妮),et al.Surface activity of glycosyl Gemini cationic surfactants[J].China Surfactant Detergent&Cosemetics(日用化学工业),2015,45(10):541-545.
[14]Li P,Chen Q,Zhao J,et al.Synthesis and properties of x-type alkyl sulfonate Gemini surfactants derived from cyanuric chloride[J].Journal of Surfactants&Detergents,2012,15(4):449-456.
[15]Lai Xiaojuan(赖小娟),Wang Jie(汪洁),Wang Lei(王磊),et al.Synthesis of novel sulfonic acid-based Gemini surfactants and their application in oil and gas wells[J].Chemical Industry and Engineering Progress(化工进展),2018,37(5):1956-1961.
[16]Fang Yun(方云),Xia Yongmei(夏咏梅).Amphoteric surfactants:(Ⅰ)overview of amphoteric surfactants[J].China Surfactant Detergent&cosemetics(日用化学工业),2000,30(3):53-55.
[17]Du Li(杜丽).Synthesis and study of mesoporous materials with special morphology[D].Guangzhou:South China University of Technology(华南理工大学),2009.
[18]Zhou Long(周龙).Design,synthesis and properties of carboxylate Gemini surfactants[D].Dalian:Liaoning Normal University(辽宁师范大学),2012.
[19]Wang Ruijuan(王瑞娟),Li Gangsen(李刚森),Yan Haitao(闫海涛),et al.Synthesis and properties of sulfonate Gemini surfactants[J].Fine Chemicals(精细化工),2017,34(2):166-171.
[20]Li Pan(李盼),Xu Hong(徐红),Xie Hongyu(解鸿宇),et al.Synthesis and properties of sodium itaconate diester sulfonate type Gemini surfactant[J].Chemical Industry and Engineering Progress(化工进展),2017,36(8):3047-3052.
[21]Hou Lu(侯璐),Hu Zhiyong(胡志勇),Jiang Xinxin(姜欣欣),et al.Synthesis and surface activity of asymmetric surfactants containing hydroxyl-sulfonic acid groups[J].China Surfactant Detergent&Cosemetics(日用化学工业),2014,44(3):121-125,130.
[22]Deng Honglin(邓红琳),Zhao Wenbin(赵文彬),Yuan Lihe(袁立鹤).Application of drilling fluid non-landing technology in daniudi gas field[J].Fault Block Oil&Gas Field(断块油气田),2014,21(1):97-99.
[23]Ji Zhonglun(冀忠伦),Ren Xiaorong(任小荣),Yang Qin(杨琴),et al.Discussion on the technology and mode of non-dumping treatment of waste drilling fluid[J].Environmental Protection of Oil&Gas Fields(油气田环境保护),2016,26(2):30-32.
[24]Xiao Chunxue(肖春学),Wang Yong(王勇).Research on drilling fluid dumping technology in sulige gas field[J].Environmental Protection of Oil&Gas Fields(油气田环境保护),2017,27(6):36-38.