烷基酚类双子表面活性剂的合成及其性能研究
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摘要
本文研究了烷基酚类双子表面活性剂的合成、表征及其性能。以脂肪酸、苯酚为原料,经酰化反应、酯化反应、Fries重排、黄鸣龙还原等步骤,得到正构长链烷基酚,再与多聚甲醛在酸性催化剂下进行缩合反应,生成二(2-羟基-5-长链烷基苯基)甲烷,用核磁共振氢谱和碳谱、红外光谱对产物进行了结构鉴定。据上述反应路线,以工业品壬基酚和多聚甲醛为原料,合成出了二(2-羟基-5-壬基苯基)甲烷,并对其工艺条件进行了研究。结果表明,选用固体酸A作催化剂,烷基酚和甲醛配比为2:1,130℃反应4h,产物产率达到60.1%,且反应转化率和选择性分别为63.1%和95.3%。
将中间体二(2-羟基-5-壬基苯基)甲烷与环氧乙烷在碱性条件下加成反应,通过改变反应物配比等因素来控制环氧乙烷加成数,得到一系列具有不同亲水基长度(加成数m分别为4、7、10、15、20、30)的非离子双子表面活性剂。并进行了性能测定,结果为:壬基酚聚氧乙烯醚NP-10及其二聚体GNP-10的HLB值均为13.6; NP-10溶液(1%, wt)的浊点为60℃,GNP-10溶液(1%, wt)的浊点为53℃;水溶液中GNP-10的CMC = 0.0242 mmol·L-1,γCMC = 38.3 mN·m-1,与其相应的传统表面活性剂NP-10的CMC = 0.0775 mmol·L-1,γCMC = 40.2 mN·m-1。由此说明这种新型双子表面活性剂具有较高的表面活性。GNP-10的表观黏度随剪切速率增加明显降低,是假塑性流体;NP-10表现为近似牛顿性。在相同剪切速率下,GNP-10的表观黏度要大于NP-10。
Five intermediates for preparing long chain n-alkylphenol Gemini surfactants, bis-(2-hydroxy-5-n-alkylphenyl)-methanes, were synthesized from fatty acid, phenol, and paraformaldehyde through Friedel-Crafts acylation, esterification, Fries rearrangement, Huang Minlon reduction, and condensation, and their molecular structures were confirmed by NMR and FTIR. According to this synthesis route of bis-(2-hydroxy-5-n-alkylphenyl)- methane, the bis-(2-hydroxy-5-nonylphenyl)-methane has also been synthesized by using isononylphenol (industrial product) and paraformaldehyde successfully. It was showed that when n-alkylphenol and paraformaldehyde in molar ratio 2:1 reacted at 130℃for 4 hours, the product yield could be reached 60.1% and the alkylphenol conversion and selectivity of product were 63.1% and 95.3% respectively.
A series of novel nonionic Gemini surfactants (m = 4, 7, 10, 15, 20, 30) were synthesized from bis-(2-hydroxy-5-alkylphenyl)-methanes and ethylene oxide. Critical micelle concentrations (CMC) and surface tensions of the monomer and dimer surfactant in aqueous solution were tested by Wilhelmy-Plate method. The CMC of Gemini isononylphenol polyethoxylate-10 (GNP-10) and isononylphenol polyethoxylate-10 (NP-10) were 0.0242 mmol·L-1 and 0.0775 mmol·L-1. Their surface tensions at CMC were 38.3 mN·m-1 and 40.2 mN·m-1. Their HLB values were both 13.6. And their cloud points were 60℃and 53℃, respectively. The result showed that this kind of Gemini surfactant exhibited much better surface activity. GNP-10 showed shear-thinning behavior, while Newtonian behavior was found on NP-10. The viscosity of GNP-10 was higher than NP-10 at the same shear-rate.
将中间体二(2-羟基-5-壬基苯基)甲烷与环氧乙烷在碱性条件下加成反应,通过改变反应物配比等因素来控制环氧乙烷加成数,得到一系列具有不同亲水基长度(加成数m分别为4、7、10、15、20、30)的非离子双子表面活性剂。并进行了性能测定,结果为:壬基酚聚氧乙烯醚NP-10及其二聚体GNP-10的HLB值均为13.6; NP-10溶液(1%, wt)的浊点为60℃,GNP-10溶液(1%, wt)的浊点为53℃;水溶液中GNP-10的CMC = 0.0242 mmol·L-1,γCMC = 38.3 mN·m-1,与其相应的传统表面活性剂NP-10的CMC = 0.0775 mmol·L-1,γCMC = 40.2 mN·m-1。由此说明这种新型双子表面活性剂具有较高的表面活性。GNP-10的表观黏度随剪切速率增加明显降低,是假塑性流体;NP-10表现为近似牛顿性。在相同剪切速率下,GNP-10的表观黏度要大于NP-10。
Five intermediates for preparing long chain n-alkylphenol Gemini surfactants, bis-(2-hydroxy-5-n-alkylphenyl)-methanes, were synthesized from fatty acid, phenol, and paraformaldehyde through Friedel-Crafts acylation, esterification, Fries rearrangement, Huang Minlon reduction, and condensation, and their molecular structures were confirmed by NMR and FTIR. According to this synthesis route of bis-(2-hydroxy-5-n-alkylphenyl)- methane, the bis-(2-hydroxy-5-nonylphenyl)-methane has also been synthesized by using isononylphenol (industrial product) and paraformaldehyde successfully. It was showed that when n-alkylphenol and paraformaldehyde in molar ratio 2:1 reacted at 130℃for 4 hours, the product yield could be reached 60.1% and the alkylphenol conversion and selectivity of product were 63.1% and 95.3% respectively.
A series of novel nonionic Gemini surfactants (m = 4, 7, 10, 15, 20, 30) were synthesized from bis-(2-hydroxy-5-alkylphenyl)-methanes and ethylene oxide. Critical micelle concentrations (CMC) and surface tensions of the monomer and dimer surfactant in aqueous solution were tested by Wilhelmy-Plate method. The CMC of Gemini isononylphenol polyethoxylate-10 (GNP-10) and isononylphenol polyethoxylate-10 (NP-10) were 0.0242 mmol·L-1 and 0.0775 mmol·L-1. Their surface tensions at CMC were 38.3 mN·m-1 and 40.2 mN·m-1. Their HLB values were both 13.6. And their cloud points were 60℃and 53℃, respectively. The result showed that this kind of Gemini surfactant exhibited much better surface activity. GNP-10 showed shear-thinning behavior, while Newtonian behavior was found on NP-10. The viscosity of GNP-10 was higher than NP-10 at the same shear-rate.
引文
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3梁梦兰.表面活性剂和洗涤剂――制备、性质、应用.北京:科学技术文献出版社, 1990. 1~20
4段世铎,王万兴.非离子表面活性剂.北京:中国铁道出版社, 1990. 1~5
5黄惠琴.表面活性剂的应用与发展趋势.现代化工, 2001, 21(5): 6~8
6郑薇.表面活性剂工业的技术进展.化工进展, 2003, 22(4): 329~335
7赵国玺.表面活性剂科学的一些进展.物理化学学报, 1997, 13(8): 760~768
8耿云鹏,李明远,林梅钦,等.非离子型Gemini表面活性剂对交联聚合物溶液性质的影响.石油学报(石油加工), 2006, 22(4): 30~33
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10郭万奎,杨振宇,伍晓林,等.用于三次采油的新型弱碱表面活性剂.石油学报, 2006, 27(5): 75~78
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