环烷基甲胺的合成研究
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摘要
本论文主要研究环烷基甲胺合成过程中的环烷基化反应和氰基氢化反应。乙醇钠体系进行环烷基化反应时间长、收率低。以碳酸钾为碱,甲苯为溶剂,相转移催化丙二酸二乙酯及氰乙酸乙酯的环烷基化反应,该方法具有反应时间短、收率高等优势。相转移催化剂对环烷基化反应有着重要的作用,季铵盐、聚醚都可作为环烷基化反应的催化剂,本文采用季铵盐和聚乙二醇复配表现出“协同效应”使反应产率得到提高。相转移催化环烷基化反应不适合采用无溶剂法来进行,对反应过程中的溶剂效应进行分析后选择甲苯作为溶剂和带水剂。通过对环烷基化反应进行动力学分析,证明了该反应属于二级反应,同时计算出环烷基化反应的表观反应活化能。对相转移催化环烷基化反应的反应条件进行了优化,并且在1000L的反应釜中进行了中试放大实验,放大后收率稳定,为工业化提供了参考数据。
采用微波辐射进行相转移催化丙二酸二乙酯及氰乙酸乙酯的环烷基化反应。本文系统研究了极性非质子溶剂和弱极性非质子溶剂在微波环烷基化反应中的应用情况,发现弱极性的非质子溶剂如甲苯在环烷基化反应中具有比极性非质子溶剂更好的使用效果。对离子液体在微波环烷基化中的应用进行了研究,研究结果表明添加少量离子液体的反应介质能更好的促使反应的进行。微波对相转移催化环烷基化反应的作用分为“热效应”和“非致热效应”,通过实验证明了它们对环烷基化反应的影响。
采用非晶态合金Ni-B纳米管为催化剂进行环烷基氰化物的加氢反应,反应速度明显快于以Raney Ni和非晶态合金Ni-B纳米颗粒为催化剂的氢化速度,并且对伯胺的选择性远远高于后两种催化剂。非晶态合金Ni-B纳米管大的表面积以及纳米管具有良好的储氢性能都有利于加快氰基的氢化反应速度,特别是纳米管具有负曲率的内表面,使得多个表面位之间发生协同的概率增加,同时液体在非晶态合金纳米管内发生管的限域效应,促使氰基转化反应的平衡倾向于向右进行,加快氰基的转化速度。非晶态合金Ni-B纳米管在氰基催化氢化反应中保持了良好的稳定性。非晶态合金Ni-B纳米管对氯代硝基苯加氢也具有良好的催化活性,而且能很好的抑制脱氯反应的发生。
利用超声波处理非晶态合金Ni-B纳米管催化剂,处理后的催化剂对环烷基氰化物具有更好的加氢活性。根据超声波的“空穴效应”对超声波辅助常压氢化环烷基氰化物的反应机理及超声波促进催化氢化反应机理进行了研究,实验证明超声波辅助还原环烷基氰化物并未改变反应的表观反应活化能。超声波辅助常压下以非晶态合金Ni-B纳米管为催化剂对硝基苯进行氢化还原,该催化剂显示了较好的催化活性。
This paper mainly studied the cycloalkylation and hydrogenation in the synthesis of cycloalkanemethanamine. The traditional method of cycloalkylation was use sodium ethylate as catalyst and ethanol as solvent, this method with the disadvantage of long reaction period and low yield. The cycloalkylation of diethyl malonate and ethyl cyanoacetate with alkyl dihalide was investigated by using comminuted potassium carbonate as a base and toluene as solvent in the presence of phase-transfer catalyst (PTC), which provided a conventional procedure with the advantage of short reaction period and high product yield. PTCs were essential to cycloalkylation of diethyl malonate and ethyl cyanoacetate, quaternary ammonium compound and polyethyleneglycol were used selectively. Nevertheless, the mixtures of them were more active because of "synergistic interactions". The reaction was not suitable conducted under solvent-free condition, water formed during the reaction was removed by azeotropic distillation with toluene throughout the reaction. The factors influencing the product yield were discussed and the mechanism and kinetic of the reaction were also studied on the basis of the experimental data, the reaction can be described by the pseudo-second-order kinetics, and then calculated the cycloalkylation activation energy. Pilot-plant of cycloalkylation was investigated in 1000 L reaction equipment, the yield of the optimum technique show stable performance and the pilot-plant test provides the basic infromations for industrial production.
The cycloalkylation was investigated using microwave irradiation in the presence of PTC. As we known, solvents were very important to the reaction, the comprehensive study showed some less polar aromatic solvent (toluene) had better effect, comparing to dipolar solvents in cycloalkylation under microwave irradiation. The applications of ionic liquids were also studied, indicating the reactions with added ionic liquids into the solvent were more efficient. Since the early days of microwave synthesis, the observed rate accelerations compared to oil-bath experiments have led to speculation on the existence of so-called "thermal" and "non-thermal" effect, this article analyzed the affection on cycloalkylation on the basis of the experiment data.
In comparison with noncrystalline Ni-B nanoparticales and Raney Ni catalysts, the noncrystalline Ni-B nanotubes exhibited higher activity and better selectivity in the hydrogenation of cycloalkanecarbonitrile. The higher catalytic activity of the nanotubes can be partially ascribed to their larger surface area and good hydrogen storage properties. Especially, the negative curvature of the nanotube's inner surface can enhance the coordination of reaction molecules by the multiple active centers, which should affect the reaction equilibrium and result in an increase in the yield of cycloalkanemethanamine. Transmission electron microscopy (TEM) was used to determine the characterization and stability of the nanotubes. Noncrystalline Ni-B nanotubes exhibited higher activity and better selectivity in the hydrogenation of chloronitrobenzene compared wtih noncrystalline Ni-B nanoparticales and Raney Ni catalysts.
The effect of the preultrasonication on the catalytic performance of noncrystalline Ni-B nanotubes was investigated in selcetive hydrogenation of cycloalkanecarbonitrile to cycloalkanemethanamine. The results demonstrated that employment of ultrasonic wave had benefit on the maintenance of catalyst activity. The mechanic of ultrasonic hydrogenation of cycloalkanecarbonitrile under normal pressure was discussed on the basis of the "cavitation effect". The activation energy of the reaction was calculated, which had no obvious changed under ultrasonic compared with traditional hydrogenation. The noncrystalline Ni-B nanotubes also exhibited good activity for hydrogenation of nitrobeneze under ultrasonic irradition at atmospheric pressure.
采用微波辐射进行相转移催化丙二酸二乙酯及氰乙酸乙酯的环烷基化反应。本文系统研究了极性非质子溶剂和弱极性非质子溶剂在微波环烷基化反应中的应用情况,发现弱极性的非质子溶剂如甲苯在环烷基化反应中具有比极性非质子溶剂更好的使用效果。对离子液体在微波环烷基化中的应用进行了研究,研究结果表明添加少量离子液体的反应介质能更好的促使反应的进行。微波对相转移催化环烷基化反应的作用分为“热效应”和“非致热效应”,通过实验证明了它们对环烷基化反应的影响。
采用非晶态合金Ni-B纳米管为催化剂进行环烷基氰化物的加氢反应,反应速度明显快于以Raney Ni和非晶态合金Ni-B纳米颗粒为催化剂的氢化速度,并且对伯胺的选择性远远高于后两种催化剂。非晶态合金Ni-B纳米管大的表面积以及纳米管具有良好的储氢性能都有利于加快氰基的氢化反应速度,特别是纳米管具有负曲率的内表面,使得多个表面位之间发生协同的概率增加,同时液体在非晶态合金纳米管内发生管的限域效应,促使氰基转化反应的平衡倾向于向右进行,加快氰基的转化速度。非晶态合金Ni-B纳米管在氰基催化氢化反应中保持了良好的稳定性。非晶态合金Ni-B纳米管对氯代硝基苯加氢也具有良好的催化活性,而且能很好的抑制脱氯反应的发生。
利用超声波处理非晶态合金Ni-B纳米管催化剂,处理后的催化剂对环烷基氰化物具有更好的加氢活性。根据超声波的“空穴效应”对超声波辅助常压氢化环烷基氰化物的反应机理及超声波促进催化氢化反应机理进行了研究,实验证明超声波辅助还原环烷基氰化物并未改变反应的表观反应活化能。超声波辅助常压下以非晶态合金Ni-B纳米管为催化剂对硝基苯进行氢化还原,该催化剂显示了较好的催化活性。
This paper mainly studied the cycloalkylation and hydrogenation in the synthesis of cycloalkanemethanamine. The traditional method of cycloalkylation was use sodium ethylate as catalyst and ethanol as solvent, this method with the disadvantage of long reaction period and low yield. The cycloalkylation of diethyl malonate and ethyl cyanoacetate with alkyl dihalide was investigated by using comminuted potassium carbonate as a base and toluene as solvent in the presence of phase-transfer catalyst (PTC), which provided a conventional procedure with the advantage of short reaction period and high product yield. PTCs were essential to cycloalkylation of diethyl malonate and ethyl cyanoacetate, quaternary ammonium compound and polyethyleneglycol were used selectively. Nevertheless, the mixtures of them were more active because of "synergistic interactions". The reaction was not suitable conducted under solvent-free condition, water formed during the reaction was removed by azeotropic distillation with toluene throughout the reaction. The factors influencing the product yield were discussed and the mechanism and kinetic of the reaction were also studied on the basis of the experimental data, the reaction can be described by the pseudo-second-order kinetics, and then calculated the cycloalkylation activation energy. Pilot-plant of cycloalkylation was investigated in 1000 L reaction equipment, the yield of the optimum technique show stable performance and the pilot-plant test provides the basic infromations for industrial production.
The cycloalkylation was investigated using microwave irradiation in the presence of PTC. As we known, solvents were very important to the reaction, the comprehensive study showed some less polar aromatic solvent (toluene) had better effect, comparing to dipolar solvents in cycloalkylation under microwave irradiation. The applications of ionic liquids were also studied, indicating the reactions with added ionic liquids into the solvent were more efficient. Since the early days of microwave synthesis, the observed rate accelerations compared to oil-bath experiments have led to speculation on the existence of so-called "thermal" and "non-thermal" effect, this article analyzed the affection on cycloalkylation on the basis of the experiment data.
In comparison with noncrystalline Ni-B nanoparticales and Raney Ni catalysts, the noncrystalline Ni-B nanotubes exhibited higher activity and better selectivity in the hydrogenation of cycloalkanecarbonitrile. The higher catalytic activity of the nanotubes can be partially ascribed to their larger surface area and good hydrogen storage properties. Especially, the negative curvature of the nanotube's inner surface can enhance the coordination of reaction molecules by the multiple active centers, which should affect the reaction equilibrium and result in an increase in the yield of cycloalkanemethanamine. Transmission electron microscopy (TEM) was used to determine the characterization and stability of the nanotubes. Noncrystalline Ni-B nanotubes exhibited higher activity and better selectivity in the hydrogenation of chloronitrobenzene compared wtih noncrystalline Ni-B nanoparticales and Raney Ni catalysts.
The effect of the preultrasonication on the catalytic performance of noncrystalline Ni-B nanotubes was investigated in selcetive hydrogenation of cycloalkanecarbonitrile to cycloalkanemethanamine. The results demonstrated that employment of ultrasonic wave had benefit on the maintenance of catalyst activity. The mechanic of ultrasonic hydrogenation of cycloalkanecarbonitrile under normal pressure was discussed on the basis of the "cavitation effect". The activation energy of the reaction was calculated, which had no obvious changed under ultrasonic compared with traditional hydrogenation. The noncrystalline Ni-B nanotubes also exhibited good activity for hydrogenation of nitrobeneze under ultrasonic irradition at atmospheric pressure.
引文
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