金属多氧酸盐离子化合物的设计合成和催化应用
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摘要
烯烃的环氧化反应是合成环氧化物的重要途径,而环氧化合物是重要的化工合成中间体,因此研究烯烃的环氧化反应具有很重要的理论和实践意义。由于室温离子液体具有特殊的物化性质,被认为是继水和超临界二氧化碳之后又一大类在现代有机催化合成中具有良好应用前景的反应介质和新型绿色溶剂系列。而金属多氧酸盐由于具有结构确定、溶于极性溶剂、可参与均相或者非均相反应、同时具有酸性和氧化性等一系列优点,广泛应用在烯烃的环氧化反应中。
首先,为了深入了解离子液体的物化性质,主要通过核磁共振技术(NMR)、红外光谱(FT-IR)以及紫外光谱(UV-vis)三种方法表征了一系列1-丁基-3-甲基咪唑类离子液体,考察了不同的阴离子与咪唑环上两个氮原子之间的H2质子间氢键强度的区别,以期理解一系列离子液体分子内氢键的形成规律和作用强度。同时,利用离子液体“可设计”的特殊性质,将钨酸根阴离子引入烷基咪唑类离子液体的结构中。首次合成得到了钨酸根阴离子功能化的新颖离子液体,通过IR、NMR和元素分析对其结构进行了表征确认,并对其在不同温度下的电导率和粘度的变化,以及室温下的电化学性质进行了详细的表征。主要探讨了分子内静电相互作用、氢键、分子间范德华力以及阴阳离子的结构对于离子液体物化性质的影响,从而得到离子液体的结构与性质间的关系。
其次,设计并合成了基于同多阴离子的质子化咪唑离子液体,将其应用于烯烃的环氧化反应,发现质子化十二烷基咪唑的过氧钨酸盐可以作为一种反应控制的相分离催化剂催化环氧化反应。利用催化剂在反应过程中溶解,反应结束后析出的特点,实现反应后催化剂的自分离,一定程度上解决了均相催化剂难分离的缺陷。
然后,利用磁分离具有简单易分离的特性以及均相催化反应始终存在着催化剂不易分离和循环效果不好的缺点。合成了磁性纳米颗粒负载的过氧酸盐催化剂,通过活性物种分子中的硅羟基与载体表面硅羟基间的氢键作用固定活性过氧钨酸根,得到的催化剂在进行了详细的结构表征后,用于催化环氧化反应。并且与传统的共价键负载方式得到的催化剂进行了活性和稳定性的比较。
同时,基于磺酸基与硅羟基间可以形成氢键的特性,我们将杂多阴离子(PW110397-)通过磺酸内盐与硅羟基间的氢键作用固定到二氧化硅包覆的四氧化三铁磁性载体表面合成了另一类磁性催化剂。同样将该磁性催化剂用于烯烃的催化环氧化反应,对该催化剂在无溶剂及有机溶剂中的反应过程进行了深入的研究。总的来说,两类不同类型的磁性催化剂结合了均相催化剂高活性的优点以及非均相催化剂易分离的特性。
在对基于磺酸基的负载型催化剂进行活性测试的过程中,我们发现：即使在冰浴反应的条件下,非负载的离子液体内盐-缺位多氧酸盐(Na7PW11O39)的复合物(DSPIM-POM)表现出优异的环氧化活性。于是对复合物DSPIM-POM在冰浴条件下催化的环氧化反应进行了详细的研究,从复合物中两组分的摩尔比、反应物与催化剂的投料比以及不同的反应温度等多个角度对该体系进行了详细的探讨。
Olefin epoxidation is an important approach to the synthesis of epoxide, which is remarkable chimical synthesis intermediate and thus plays an important role in scientific and potential applications. Due to the wonderful physicochemical properties, Ionic Liquid (IL) was considerd as one of the most promising reaction medium and green solvent series besides water and supercritical carbon dioxide. Meanwhile, polyoxometalate was applied in olefin epoxidation extensively because of its good properties as well-defined structure, good solubility in polar solvents, tunable acidity and redox.
First, to know more about ILs'physicochemical properties, NMR, FT-IR and UV-vis were used to characterize a series of1-butyl-3-methylimidazolium ILs. The hydrogen-bonding interaction between imidazolium cations and different anions has been investigated to understand the hydrogen-bonding formation and strength in imidazolium IL molecules. At the same time, novel tungstate-based room temperature ILs were obtained as ILs were "designable" in both cations and anions. And then the physicochemical properties of these ILs, including the temperature dependency of the dynamic ionic conductivity, viscosity and the electrochemical stability were determined and analyzed according to the nature of the cations and/or anions in detail, which were also compared with those of the conventional ILs. This part mainly discussed the electrostatic interaction, the hydrogen bonding, and van der Waals interactions in these ILs and attempted to identify the structure-property relationships, including the effect of both cations and anions.
Second, protic alkylimidazolium polyoxometalates were synthesized and characterized by the methods of NMR, IR and TGA etc. Then, these salts were employed as catalysts for the epoxidation of cyclooctene in different media. The novel protic N-dodecylimidazolium peroxotungstate [HDIm]2[{W=O(O2)2}2(μ-O)] was found to be a room temperature liquid molten salt (IL) and the most effective catalyst for the epoxidation of cyclooctene. On the basis of experimental observation, an efficient reaction-induced phase-separation catalyst system has been developed:the reaction system can switch from tri-phase to emulsion and then to biphase and finally to all the catalyst self-precipitating at the end of the reaction, which made the recovery and reuse of the present catalyst very convenient.
Then, to overcome the disadvantages of hard separation and poor recyclability of homogeneous catalysis as well as the obvious advantages of magnetic separation compared to conventional separation methods. Magnetically separable catalyst has been prepared and the catalytically active IL-type peroxotungstate is expected to be immobilized by hydrogen-bonding. It was also employed for the epoxidation of olefins with hydrogen peroxide. The activity of both activity and stability of hydrogen-bonding catalyst were also compard with the conventional covalent-bonding catalyst.
Since there definitely exist hydrogen-bonding interactions between the silanol groups of the support and the sulfonate groups, lacunary-type anion (PW11O397-) was successfully immobilized by hydrogen bonding between the sulfonate anion and silanol group on the surface of the core-shell Fe3O4/SiO2MNPs. And the catalytic potential was evaluated in the epoxidation of a variety of olefins as well as allylic alcohols. The catalytic epoxidation was investigated under the condition of no solvent and in organic solvent, respectively. After all, we expect that both magnetically separable catalysts would combine the advantages of high activity of homogeneous catalysts and easy separation of heterogeneous catalysts.
Last but not the least, we found another extremely efficient catalyst:sulfate zwittion-POM (Na7PW11O39) composite. The catalytic epoxidation by this novel hybrid material in ice bath was investigated in detail. It was found that the molar ratio of sulfate zwittion to POM (Na7PW11O39) influenced the activity significantly, and reaction conditions like the molar ratios among substrate, oxygen source and catalyst, reaction temperatures have also been optimized to obtain high yield toward epoxides.
首先,为了深入了解离子液体的物化性质,主要通过核磁共振技术(NMR)、红外光谱(FT-IR)以及紫外光谱(UV-vis)三种方法表征了一系列1-丁基-3-甲基咪唑类离子液体,考察了不同的阴离子与咪唑环上两个氮原子之间的H2质子间氢键强度的区别,以期理解一系列离子液体分子内氢键的形成规律和作用强度。同时,利用离子液体“可设计”的特殊性质,将钨酸根阴离子引入烷基咪唑类离子液体的结构中。首次合成得到了钨酸根阴离子功能化的新颖离子液体,通过IR、NMR和元素分析对其结构进行了表征确认,并对其在不同温度下的电导率和粘度的变化,以及室温下的电化学性质进行了详细的表征。主要探讨了分子内静电相互作用、氢键、分子间范德华力以及阴阳离子的结构对于离子液体物化性质的影响,从而得到离子液体的结构与性质间的关系。
其次,设计并合成了基于同多阴离子的质子化咪唑离子液体,将其应用于烯烃的环氧化反应,发现质子化十二烷基咪唑的过氧钨酸盐可以作为一种反应控制的相分离催化剂催化环氧化反应。利用催化剂在反应过程中溶解,反应结束后析出的特点,实现反应后催化剂的自分离,一定程度上解决了均相催化剂难分离的缺陷。
然后,利用磁分离具有简单易分离的特性以及均相催化反应始终存在着催化剂不易分离和循环效果不好的缺点。合成了磁性纳米颗粒负载的过氧酸盐催化剂,通过活性物种分子中的硅羟基与载体表面硅羟基间的氢键作用固定活性过氧钨酸根,得到的催化剂在进行了详细的结构表征后,用于催化环氧化反应。并且与传统的共价键负载方式得到的催化剂进行了活性和稳定性的比较。
同时,基于磺酸基与硅羟基间可以形成氢键的特性,我们将杂多阴离子(PW110397-)通过磺酸内盐与硅羟基间的氢键作用固定到二氧化硅包覆的四氧化三铁磁性载体表面合成了另一类磁性催化剂。同样将该磁性催化剂用于烯烃的催化环氧化反应,对该催化剂在无溶剂及有机溶剂中的反应过程进行了深入的研究。总的来说,两类不同类型的磁性催化剂结合了均相催化剂高活性的优点以及非均相催化剂易分离的特性。
在对基于磺酸基的负载型催化剂进行活性测试的过程中,我们发现：即使在冰浴反应的条件下,非负载的离子液体内盐-缺位多氧酸盐(Na7PW11O39)的复合物(DSPIM-POM)表现出优异的环氧化活性。于是对复合物DSPIM-POM在冰浴条件下催化的环氧化反应进行了详细的研究,从复合物中两组分的摩尔比、反应物与催化剂的投料比以及不同的反应温度等多个角度对该体系进行了详细的探讨。
Olefin epoxidation is an important approach to the synthesis of epoxide, which is remarkable chimical synthesis intermediate and thus plays an important role in scientific and potential applications. Due to the wonderful physicochemical properties, Ionic Liquid (IL) was considerd as one of the most promising reaction medium and green solvent series besides water and supercritical carbon dioxide. Meanwhile, polyoxometalate was applied in olefin epoxidation extensively because of its good properties as well-defined structure, good solubility in polar solvents, tunable acidity and redox.
First, to know more about ILs'physicochemical properties, NMR, FT-IR and UV-vis were used to characterize a series of1-butyl-3-methylimidazolium ILs. The hydrogen-bonding interaction between imidazolium cations and different anions has been investigated to understand the hydrogen-bonding formation and strength in imidazolium IL molecules. At the same time, novel tungstate-based room temperature ILs were obtained as ILs were "designable" in both cations and anions. And then the physicochemical properties of these ILs, including the temperature dependency of the dynamic ionic conductivity, viscosity and the electrochemical stability were determined and analyzed according to the nature of the cations and/or anions in detail, which were also compared with those of the conventional ILs. This part mainly discussed the electrostatic interaction, the hydrogen bonding, and van der Waals interactions in these ILs and attempted to identify the structure-property relationships, including the effect of both cations and anions.
Second, protic alkylimidazolium polyoxometalates were synthesized and characterized by the methods of NMR, IR and TGA etc. Then, these salts were employed as catalysts for the epoxidation of cyclooctene in different media. The novel protic N-dodecylimidazolium peroxotungstate [HDIm]2[{W=O(O2)2}2(μ-O)] was found to be a room temperature liquid molten salt (IL) and the most effective catalyst for the epoxidation of cyclooctene. On the basis of experimental observation, an efficient reaction-induced phase-separation catalyst system has been developed:the reaction system can switch from tri-phase to emulsion and then to biphase and finally to all the catalyst self-precipitating at the end of the reaction, which made the recovery and reuse of the present catalyst very convenient.
Then, to overcome the disadvantages of hard separation and poor recyclability of homogeneous catalysis as well as the obvious advantages of magnetic separation compared to conventional separation methods. Magnetically separable catalyst has been prepared and the catalytically active IL-type peroxotungstate is expected to be immobilized by hydrogen-bonding. It was also employed for the epoxidation of olefins with hydrogen peroxide. The activity of both activity and stability of hydrogen-bonding catalyst were also compard with the conventional covalent-bonding catalyst.
Since there definitely exist hydrogen-bonding interactions between the silanol groups of the support and the sulfonate groups, lacunary-type anion (PW11O397-) was successfully immobilized by hydrogen bonding between the sulfonate anion and silanol group on the surface of the core-shell Fe3O4/SiO2MNPs. And the catalytic potential was evaluated in the epoxidation of a variety of olefins as well as allylic alcohols. The catalytic epoxidation was investigated under the condition of no solvent and in organic solvent, respectively. After all, we expect that both magnetically separable catalysts would combine the advantages of high activity of homogeneous catalysts and easy separation of heterogeneous catalysts.
Last but not the least, we found another extremely efficient catalyst:sulfate zwittion-POM (Na7PW11O39) composite. The catalytic epoxidation by this novel hybrid material in ice bath was investigated in detail. It was found that the molar ratio of sulfate zwittion to POM (Na7PW11O39) influenced the activity significantly, and reaction conditions like the molar ratios among substrate, oxygen source and catalyst, reaction temperatures have also been optimized to obtain high yield toward epoxides.
引文
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