酰胺型双亲油基甜菜碱的合成与性能研究
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摘要
双长链甜菜碱型表面活性剂可用作三次采油中驱油用表面活性剂。双十二酰胺基甜菜碱表面活性剂属于在双长链甜菜碱结构的基础上进行改良的新型品种。两个疏水烷基长链使得双十二酰胺基甜菜碱的亲油性优于一般表面活性剂,这一点有利于降低油水界面张力,同时双十二酰胺基甜菜碱的结构中因酰胺基团的引入,一定程度上保证了产品具有良好的生物降解性、温和性和化学稳定性。
基于上述考虑,本论文设计了一种新结构的甜菜碱型两性表面活性剂—双十二酰胺基甜菜碱,并以十二酸、二乙烯三胺、氯乙酸钠等为主要原料分三步进行了制备,采用红外光谱、质谱、核磁等手段进行了结构确证。利用正交试验确定了中间体N,N-双-(十二酰基乙基)胺和N,N-双-(十二酰基乙基)-N-甲基胺的较优合成条件,研究了第三步合成的不同方法,并对双十二酰胺基甜菜碱的界面性能进行了研究。
正交试验研究结果表明,以十二酸和二乙烯三胺为原料,KOH作催化剂,经酰胺化合成N,N-双-(十二酰基乙基)胺的反应较优条件为:n(二乙烯三胺):n(十二酸)=1:2.0,反应温度170℃,反应时间8h,催化剂用量为反应物总质量的0.5%。N,N-双-(十二酰基乙基)胺与甲酸、甲醛的反应的反应较优条件为:乙醇作溶剂,n(双十二酰胺):n(甲酸):n(甲醛)=1:2.3:1.7,85℃反应10h。
本文还探讨了N,N-双-(十二酰基乙基)-N-甲基胺与氯乙酸钠合成N,N-双-(十二酰基乙基)胺基甜菜碱的不同方法,并研究了双十二酰胺基甜菜碱的界面性能。所合成的双十二酰胺基甜菜碱在25℃时临界胶束浓度cmc为1.2×10-5mol·L-1,γcmc为25.38mN/m,饱和吸附时在气/液界面上的分子截面积为0.28nm2,远远小于SDS的0.5nm2。作为甜菜碱型表面活性剂,双十二酰胺基甜菜碱具有较好的耐盐能力,类似于非离子表面活性剂,加入NaCl后cmc和γcmc仅有微小下降。用双十二酰胺基甜菜碱与其他表面活性剂复配,45℃下在表面活性剂总质量分数为0.05～0.3%的活性物浓度范围内,能使大庆原油/地层水的界面张力降至10-4mN/m数量级。
Zwitterionic betaine surfactants have been used as EOR surfactant in ASP flooding. Di-12 amide betaine was a new improved surfactant. It has better lipophilicity which owing to its two hydrophobic long-chain alkyl. This was beneficial to reduce oil-water interfacial tension. Due to two amide groups in the structure, the product has good chemical properties, such as biodegradability, mild, and chemical stability.
A new-style zwitterionic surfactant with amide group was synthesized in this paper. Due to its low-cost and high-powered, a new synthesis route of the three-step method was introduced. In this experiment, intermediates technoligical conditions, product structure, product technoligical condition, product surface and interface properties were investigated. Study and analyze the chemical stability of the target product, and to examine it as EOR surfactant.
The total results as following:
N,N-bis-(dodecylamidoethyl)-amine was synthesized from dodecanoic acid and diethylenetriamine by amidation. Optimum technics conditions were obtained by orthogonal experiment: n(diethylenetriamine):n(dodecanoic acid)=1:2.0, reaction temperature was 170℃and reaction time was 8h, the catalyst amount used was 0.5%.
N,N-bis(dodecylamidoethyl)-N-methylamine starting from formic acid and formaldehyde, ethanol as solvent. Optimum technics conditions were obtained by orthogonal experiment: in a molar ratio 1:2.3:1.7 of the intermediate and formic acid as well as formaldehyde at 85℃for 10h.
N,N-bis(dodecylamidoethyl)-N-methyl-N-carboxymethylammonium betaine can be synthesized by reacting, N,N-bis(dodecylamidoethyl)-N-methylamine with sodium chloroacetate, the reaction was a two phase reaction. The results show that the critical micelle concentration of the product is 1.2×10-5 mol·L-1,γcmc is 25.38mN/m. The saturated adsorption of the surfactant at air/water interface is so high that the cross section area of each molecule in the monolayer is 0.28nm2, which is much lower than that of sodium dodecyl sulfate, 0.5nm2. The product has a good tolerance to electrolytes. By mixing with other surfactants, they can reduce Daqing crude oil/water interfacial tension to an order of 10-4mN/m in a total surfactant concentration range of 0.05～0.3wt.% at 45℃.
基于上述考虑,本论文设计了一种新结构的甜菜碱型两性表面活性剂—双十二酰胺基甜菜碱,并以十二酸、二乙烯三胺、氯乙酸钠等为主要原料分三步进行了制备,采用红外光谱、质谱、核磁等手段进行了结构确证。利用正交试验确定了中间体N,N-双-(十二酰基乙基)胺和N,N-双-(十二酰基乙基)-N-甲基胺的较优合成条件,研究了第三步合成的不同方法,并对双十二酰胺基甜菜碱的界面性能进行了研究。
正交试验研究结果表明,以十二酸和二乙烯三胺为原料,KOH作催化剂,经酰胺化合成N,N-双-(十二酰基乙基)胺的反应较优条件为:n(二乙烯三胺):n(十二酸)=1:2.0,反应温度170℃,反应时间8h,催化剂用量为反应物总质量的0.5%。N,N-双-(十二酰基乙基)胺与甲酸、甲醛的反应的反应较优条件为:乙醇作溶剂,n(双十二酰胺):n(甲酸):n(甲醛)=1:2.3:1.7,85℃反应10h。
本文还探讨了N,N-双-(十二酰基乙基)-N-甲基胺与氯乙酸钠合成N,N-双-(十二酰基乙基)胺基甜菜碱的不同方法,并研究了双十二酰胺基甜菜碱的界面性能。所合成的双十二酰胺基甜菜碱在25℃时临界胶束浓度cmc为1.2×10-5mol·L-1,γcmc为25.38mN/m,饱和吸附时在气/液界面上的分子截面积为0.28nm2,远远小于SDS的0.5nm2。作为甜菜碱型表面活性剂,双十二酰胺基甜菜碱具有较好的耐盐能力,类似于非离子表面活性剂,加入NaCl后cmc和γcmc仅有微小下降。用双十二酰胺基甜菜碱与其他表面活性剂复配,45℃下在表面活性剂总质量分数为0.05～0.3%的活性物浓度范围内,能使大庆原油/地层水的界面张力降至10-4mN/m数量级。
Zwitterionic betaine surfactants have been used as EOR surfactant in ASP flooding. Di-12 amide betaine was a new improved surfactant. It has better lipophilicity which owing to its two hydrophobic long-chain alkyl. This was beneficial to reduce oil-water interfacial tension. Due to two amide groups in the structure, the product has good chemical properties, such as biodegradability, mild, and chemical stability.
A new-style zwitterionic surfactant with amide group was synthesized in this paper. Due to its low-cost and high-powered, a new synthesis route of the three-step method was introduced. In this experiment, intermediates technoligical conditions, product structure, product technoligical condition, product surface and interface properties were investigated. Study and analyze the chemical stability of the target product, and to examine it as EOR surfactant.
The total results as following:
N,N-bis-(dodecylamidoethyl)-amine was synthesized from dodecanoic acid and diethylenetriamine by amidation. Optimum technics conditions were obtained by orthogonal experiment: n(diethylenetriamine):n(dodecanoic acid)=1:2.0, reaction temperature was 170℃and reaction time was 8h, the catalyst amount used was 0.5%.
N,N-bis(dodecylamidoethyl)-N-methylamine starting from formic acid and formaldehyde, ethanol as solvent. Optimum technics conditions were obtained by orthogonal experiment: in a molar ratio 1:2.3:1.7 of the intermediate and formic acid as well as formaldehyde at 85℃for 10h.
N,N-bis(dodecylamidoethyl)-N-methyl-N-carboxymethylammonium betaine can be synthesized by reacting, N,N-bis(dodecylamidoethyl)-N-methylamine with sodium chloroacetate, the reaction was a two phase reaction. The results show that the critical micelle concentration of the product is 1.2×10-5 mol·L-1,γcmc is 25.38mN/m. The saturated adsorption of the surfactant at air/water interface is so high that the cross section area of each molecule in the monolayer is 0.28nm2, which is much lower than that of sodium dodecyl sulfate, 0.5nm2. The product has a good tolerance to electrolytes. By mixing with other surfactants, they can reduce Daqing crude oil/water interfacial tension to an order of 10-4mN/m in a total surfactant concentration range of 0.05～0.3wt.% at 45℃.
引文
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