棕榈酰基蛋氨酸表面活性剂的合成与性能
|
摘要
以天然产物棕榈酸和蛋氨酸为原料,通过酰氯化反应和酰胺化反应两步法合成棕榈酰基蛋氨酸表面活性剂(PMS),探究反应温度、反应时间、反应物摩尔比、反应介质体积比等因素对酰胺化反应的影响;通过傅里叶红外光谱(FTIR)、核磁共振氢谱(1H NMR)和质谱对产物的结构进行表征;研究产物的表面性能和复配体系的性能。实验结果表明:酰胺化反应最佳反应温度为30℃、n(棕榈酰氯)∶n(蛋氨酸)=1∶1.2、V(水)∶V(丙酮)=1∶2、反应时间为2.5h,在此条件下,得到产物产率89.0%;表征的结果为目标产物;合成产物临界胶束浓度为1.2×10-4mol/L,表面张力为29.59mN/m;对苯等有机溶剂的乳化作用明显优于月桂酰基谷氨酸(LAS);PMS与椰油丙基甜菜碱(CPBS)摩尔比为4∶6时复配体系表面活性最佳,临界胶束浓度达到9.5×10-5mol/L,复配体系表面张力为28.1mN/m。
Palmitoyl methionine surfactant(PMS) was synthesized using natural palmitic acid and methionine by acyl chloride reaction and amidation reaction. The effect of reaction temperature, molar ratio of reactants, reaction medium volume ratio, and reaction time on the amidation reaction was investigated by single factor experiment method. In addition, the structure of the product wascharacterized by FTIR、1H NMR and mass spectra, and the surface properties of the product and theproperties of the complex system were determined. The results showed that the optimal conditions ofamidation reaction were screened out as follows: reaction temperature of 30℃, the molar ratio of reactants1∶1.2, the volume ratio of reaction medium 1∶2, and the optimum reaction time 2.5h. Under the aboveconditions, the product yield was 89.0%. And the result of the characterization is the target product.Furthermore, the critical micelle concentration(CMC) and surface tension of product were 1.2×10-4mol/Land 29.59mN/m, respectively. The emulsification of the product with many organic solvents was clearlysuperior to lauroyl glutamic acid surfactant(LAS). When the molar ratio of PMS and coconut oil propyl betaine surfactant(CPBS)was 4∶6,the surface properties of the complex system was the best.Under those conditions,the CMC and surface tension of the complex system were 9.5×10-5mol/L and 28.1mN/m,respectively.
Palmitoyl methionine surfactant(PMS) was synthesized using natural palmitic acid and methionine by acyl chloride reaction and amidation reaction. The effect of reaction temperature, molar ratio of reactants, reaction medium volume ratio, and reaction time on the amidation reaction was investigated by single factor experiment method. In addition, the structure of the product wascharacterized by FTIR、1H NMR and mass spectra, and the surface properties of the product and theproperties of the complex system were determined. The results showed that the optimal conditions ofamidation reaction were screened out as follows: reaction temperature of 30℃, the molar ratio of reactants1∶1.2, the volume ratio of reaction medium 1∶2, and the optimum reaction time 2.5h. Under the aboveconditions, the product yield was 89.0%. And the result of the characterization is the target product.Furthermore, the critical micelle concentration(CMC) and surface tension of product were 1.2×10-4mol/Land 29.59mN/m, respectively. The emulsification of the product with many organic solvents was clearlysuperior to lauroyl glutamic acid surfactant(LAS). When the molar ratio of PMS and coconut oil propyl betaine surfactant(CPBS)was 4∶6,the surface properties of the complex system was the best.Under those conditions,the CMC and surface tension of the complex system were 9.5×10-5mol/L and 28.1mN/m,respectively.
引文
[1] INFANTE M R, PEREZ L, PINAZO A, et al. Amino acid-basedsurfactants[J].Comptes Rendus Chimie, 2004, 7(6):583-592.
[2] BORDES R, HOLMBERG K. Amino acid-based surfactants—do theydeserve more attention?[J]. Adv. Colloid Interface Sci., 2015, 222:79-91.
[3]汪保川,李宇鹏,戴国琛,等.蛋白基表面活性剂的合成、性能与应用进展[J].化工进展, 2017, 36(7):2607-2614.WANG Baochuan, LI Yupeng, DAI Guochen, et al. Synthesis,properties and applications of protein-based surfactants[J]. Chemical Industry and Engineering Progress, 2017, 36(7):2607-2614.
[4]王娟,王丹,商士斌,等.天然产物基Gemini表面活性剂研究进展[J].化工进展, 2012, 31(12):2761-2765.WANG Juan, WANG Dan, SHANG Shibing, et al. Development ofnatural product Gemini surfactants[J]. Chemical Industry andEngineering Progress, 2012, 31(12):2761-2765.
[5] SáNCHEZ L, MARTINEZ V, INFANTE M R, et al. Hemolysis andantihemolysis induced by amino acid-based surfactants[J]. ToxicologyLetters, 2007, 169(2):177-184.
[6] PINHEIRO L, FAUSTINO C. Amino acid-based surfactants forbiomedical applications[M]//Application and Characterization ofSurfactants. London:IntechOpen,2017.
[7] PERINELLI D R, CASETTARI L, CESPI M, et al. Chemical-physicalproperties and cytotoxicity of N-decanoyl amino acid-basedsurfactants:effect of polar heads[J]. Colloids and Surfaces A:Physicochemical and Engineering Aspects, 2016, 492:38-46.
[8] AMPATZIDIS C D, VARKA E M A, KARAPANTSIOS T D. Interfacialactivity of amino acid-based glycerol ether surfactants and theirperformance in stabilizing O/W cosmetic emulsions[J]. Colloids&Surfaces A:Physicochemical&Engineering Aspects, 2014, 460(9):176-183.
[9] LIANG Y, HU Z, CAO D. Surface adsorption and aggregationproperties of novel L-lysine-based Gemini surfactants[J]. Journal ofSurfactants&Detergents, 2014, 17(4):693-701.
[10]曾哲灵,王林林,郑菲,等.樟树籽仁油合成癸/月桂酰基谷氨酸钠工艺研究[J].中国油脂, 2013, 38(2):69-72.ZENG Zheling, WANG linlin, ZHENG Fei, et al. Study on thesynthesis of decyl/lauroyl glutamate from camphor tree seed oil[J].Chinese Oils, 2013, 38(2):69-72.
[11]卢峰,周侨发. N-月桂酰基-L-谷氨酸钠的合成及性能[J].广东化工, 2013, 40(6):13-14.LU Feng, ZHOU Qiaofa. Synthesis and properties of N-lauroyl-L-glutamate[J]. Guangdong Chemical Industry, 2013, 40(6):13-14.
[12]陈燕妮,卢云,吴昊,等. N-酰基氨基酸系列表面活性剂的合成和应用[J].化学研究与应用, 2001, 13(2):192-195.CHEN Yanni, LU Yun, WU Hao, et al. Synthesis and application of N-acyl amino acid series surfactants[J]. Chinese Journal of ChemicalResearch, 2001, 13(2):192-195.
[13]张逸伟,饶磊,徐旭辉,等.含亚砜基蛋氨酸型表面活性剂的合成及性能[J].精细化工, 2015, 32(11):1212-1216.ZHANG Yiwei, RAO lei, XU Xuhui, et al. Synthesis and properties ofsulfoxide-containing methionine surfactants[J]. Fine Chemicals, 2015,32(11):1212-1216.
[14]王信锐,尚小琴,赖雅平,等.棕榈酰胺丙基甜菜碱两性表面活性剂的合成及其性能[J].精细化工, 2017, 34(3):268-273.WANG Xinrui, SHANG Xiaoqin, LAI Yaping, et al. Synthesis andproperties of palmitamide propyl betaine amphoteric surfactant[J]. FineChemicals, 2017, 34(3):268-273.
[15]林璟,郑成,黄武欢,等.双酯基型有机硅季铵盐表面活性剂性能研究[J].广州大学学报(自然科学版), 2014(4):43-46.LIN Jing, ZHENG Cheng, HUANG Wuhuan, et al. Diester-basedsilicone quaternary ammonium surfactants[J]. Journal of GuangzhouUniversity(Natural Science), 2014(4):43-46.
[2] BORDES R, HOLMBERG K. Amino acid-based surfactants—do theydeserve more attention?[J]. Adv. Colloid Interface Sci., 2015, 222:79-91.
[3]汪保川,李宇鹏,戴国琛,等.蛋白基表面活性剂的合成、性能与应用进展[J].化工进展, 2017, 36(7):2607-2614.WANG Baochuan, LI Yupeng, DAI Guochen, et al. Synthesis,properties and applications of protein-based surfactants[J]. Chemical Industry and Engineering Progress, 2017, 36(7):2607-2614.
[4]王娟,王丹,商士斌,等.天然产物基Gemini表面活性剂研究进展[J].化工进展, 2012, 31(12):2761-2765.WANG Juan, WANG Dan, SHANG Shibing, et al. Development ofnatural product Gemini surfactants[J]. Chemical Industry andEngineering Progress, 2012, 31(12):2761-2765.
[5] SáNCHEZ L, MARTINEZ V, INFANTE M R, et al. Hemolysis andantihemolysis induced by amino acid-based surfactants[J]. ToxicologyLetters, 2007, 169(2):177-184.
[6] PINHEIRO L, FAUSTINO C. Amino acid-based surfactants forbiomedical applications[M]//Application and Characterization ofSurfactants. London:IntechOpen,2017.
[7] PERINELLI D R, CASETTARI L, CESPI M, et al. Chemical-physicalproperties and cytotoxicity of N-decanoyl amino acid-basedsurfactants:effect of polar heads[J]. Colloids and Surfaces A:Physicochemical and Engineering Aspects, 2016, 492:38-46.
[8] AMPATZIDIS C D, VARKA E M A, KARAPANTSIOS T D. Interfacialactivity of amino acid-based glycerol ether surfactants and theirperformance in stabilizing O/W cosmetic emulsions[J]. Colloids&Surfaces A:Physicochemical&Engineering Aspects, 2014, 460(9):176-183.
[9] LIANG Y, HU Z, CAO D. Surface adsorption and aggregationproperties of novel L-lysine-based Gemini surfactants[J]. Journal ofSurfactants&Detergents, 2014, 17(4):693-701.
[10]曾哲灵,王林林,郑菲,等.樟树籽仁油合成癸/月桂酰基谷氨酸钠工艺研究[J].中国油脂, 2013, 38(2):69-72.ZENG Zheling, WANG linlin, ZHENG Fei, et al. Study on thesynthesis of decyl/lauroyl glutamate from camphor tree seed oil[J].Chinese Oils, 2013, 38(2):69-72.
[11]卢峰,周侨发. N-月桂酰基-L-谷氨酸钠的合成及性能[J].广东化工, 2013, 40(6):13-14.LU Feng, ZHOU Qiaofa. Synthesis and properties of N-lauroyl-L-glutamate[J]. Guangdong Chemical Industry, 2013, 40(6):13-14.
[12]陈燕妮,卢云,吴昊,等. N-酰基氨基酸系列表面活性剂的合成和应用[J].化学研究与应用, 2001, 13(2):192-195.CHEN Yanni, LU Yun, WU Hao, et al. Synthesis and application of N-acyl amino acid series surfactants[J]. Chinese Journal of ChemicalResearch, 2001, 13(2):192-195.
[13]张逸伟,饶磊,徐旭辉,等.含亚砜基蛋氨酸型表面活性剂的合成及性能[J].精细化工, 2015, 32(11):1212-1216.ZHANG Yiwei, RAO lei, XU Xuhui, et al. Synthesis and properties ofsulfoxide-containing methionine surfactants[J]. Fine Chemicals, 2015,32(11):1212-1216.
[14]王信锐,尚小琴,赖雅平,等.棕榈酰胺丙基甜菜碱两性表面活性剂的合成及其性能[J].精细化工, 2017, 34(3):268-273.WANG Xinrui, SHANG Xiaoqin, LAI Yaping, et al. Synthesis andproperties of palmitamide propyl betaine amphoteric surfactant[J]. FineChemicals, 2017, 34(3):268-273.
[15]林璟,郑成,黄武欢,等.双酯基型有机硅季铵盐表面活性剂性能研究[J].广州大学学报(自然科学版), 2014(4):43-46.LIN Jing, ZHENG Cheng, HUANG Wuhuan, et al. Diester-basedsilicone quaternary ammonium surfactants[J]. Journal of GuangzhouUniversity(Natural Science), 2014(4):43-46.