离子液体两相催化体系中有机合成单元反应的研究
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摘要
离子液体是近年来在绿色化学的框架下发展起来的全新的介质与软功能材料,由于具有不挥发、不可燃、液态范围宽、热稳定性好、溶解性好、物化性质可调等优点,已被作为催化剂或反应介质成功的应用于有机合成、两相催化、电化学、分离提取等领域。催化剂的高效分离和回收利用问题一直以来是绿色化学研究的重点内容之一。具有“高温均相、低温两相”性质的温控离子液体两相催化体系和离子液体相转移催化体系,因其能有效结合均相催化体系反应高效与非均相催化体系催化剂易回收的优点己成为研究热点。
本课题主要研究了离子液体温控两相催化体系和离子液体相转移催化体系中芳烃化合物氯甲基化反应、胺解反应、水解反应、C-O偶联反应、氧化反应和还原C-C自偶联反应,以期开发出环境友好的新方法,具体的研究内容包括以下几个方面。
在实施芳烃化合物的氯甲基化反应中,分别研究了PEG1000-DAIL/甲基环己烷和PEG1000-DIL／甲基环己烷这两种离子液体温控两相催化体系对反应的影响规律。研究表明,PEG1000-DIL／甲基环己烷温控两相体系能够较好的催化芳烃化合物单氯甲基化反应；PEG1000-DAIL/甲基环己烷温控两相体系能更好的催化联苯、二甲苯和四氢萘的二氯甲基化反应,反应得到了一些对称的二氯甲基化产物。整个反应过程条件温和,选择性好,后处理简单,离子液体催化体系循环使用效果良好,实现了环境友好的氯甲基化反应。
以硫酸铜(CuS04)为催化剂,将PEG1000-DIL/甲基环己烷温控两相体系应用于有机卤化物的氨解反应。研究发现PEG1000-DIL/CuSO4催化体系可以高效的催化有机卤化物的氨解反应,反应收率在84%以上。反应选择性好,条件温和,操作简单,反应结束后产物相催化相易分离而且没有异构体生成,离子液体催化体系回收循环使用效果良好。
以酸性聚乙二醇型双子离子液体PEG1000-DAIL为基础合成了三种不同阴离子的离子液体PEG1000-DAIL[BF4],PEG1000-DAIL[PF6]和PEG1000-DAIL[OTf],发现了这三种离子液体都可以与甲苯形成良好的温控两相体系,并研究了它们在有机卤化物、环氧化合物和酯类化合物的水解反应。实验表明,采用Fe2(S04)3为辅助催化剂,在PEG1000-DAIL[BF4]/甲苯温控两相体系作用下,水解反应能够快速高效的进行。相对于环氧化合物和酯类化合物的催化水解反应过程,PEG1000-DAIL[BF4]/Fe2(SO4)3/甲苯温控两相催化体系能够更有效的催化有机卤化物的水解反应,反应速度更快。反应结束后,产物与催化体系形成油-水两相,通过简单的倾析便可实现产物与催化体系的分离。催化体系可以方便的回收循环使用而催化活性基本保持不变。
以PEG1000-DAIL为基础合成了一系列不同阴离子的过渡金属离子液体,这些离子液体可以与甲苯形成良好的温控两相体系。将所形成的温控两相体系应用于催化有机卤化物与醇和酚的C-O偶联反应,研究结果表明,过渡金属离子液体PEG1000-DAIL[CdCl3]/甲苯温控两相体系催化反应效果较好。
合成了一系列具有相转移催化性质的长链1-烷基-3-甲基咪唑盐过渡金属离子液体。分别研究了这些离子液体中有机卤化物的选择性氧化反应和有机卤化物的还原C-C自偶联反应。发明了一种新的[C12min][FeCl4]催化有机卤化物的选择性H5I06氧化体系,该体系能够有效的将一系列的有机卤化物选择性氧化为相应的醛或酮,并能高收率的得到氧化产品。离子液体催化剂可以方便的回收循环使用,反应条件温和,选择性好,操作简单,催化剂用量少,符合绿色化学的发展方向。发展了一种有效的还原C-C自偶联[C12mim][CuCl2]/Cu/Zn反应体系,该体系能够有效的将一系列苄基和芳基卤化物转化为相应的联苄和联苯类化合物,反应在无溶剂条件下进行,产品收率都在80%以上,反应选择性好,催化剂可以方便的回收循环使用,该工艺符合绿色化学的发展方向,具有良好的应用前景。
Recently, ionic liquids research has become a new field of green chemistry. Due to their favorable properties such as non-inflammability, negligible vapour pressure, reusability and high thermal stability, ionic liquid technology has been successfully applied to many areas of chemistry including organic and inorgnic synthesis, biphasic catalysis, separation proeesses, electrochemistry etc. Separation and recovery of catalyst with high efficiency plays an important role in green chemistry. Ionic liquids of catalytic system possess the thermoregulated biphasic behavior of "mono-phase under high temperature, bi-phase under room temperature" and phase transfter catalysis have been attracted much attention due to their advantages of both homogeneous and heterogeneous eatalysis with high product yield and the easy separation of product from catalytic system.
The main objective of this dissertation is to perform the chloromethylation of aromatic hydrocarbons, animation of organic halides, hydrolysis of organic halides、epoxides and esters, C-O coupling of organic halides, oxidation of organic halides, and the reductive homocoupling of benzyl and aryl halides in ionic liquids with a view to develop new environment-friendly methods, and the specific research contents include the following aspects.
Two temperature-dependent biphasic systems, PEG1000-DAIL/methylcyclohexane and PEG1000-DIL/methylcyclohexane, were used as isolated catalyst in the chloromethylation of aromatic hydrocarbons, and the effect of reaction conditions on the catalytic reaction was investigated. It was found that a new chloromethylation reaction system using PEG1000-DIL in combination with methylcyclohexane has been developed, which is capable of converting aromatic hydrocarbons into the corresponding mono-chloromethyl-substituted aromatic compounds in good to excellent isolated yield. And the new dichloromethylation reaction system using PEG1000-DA.IL in combination with methylcyclohexane has also been developed, which is capable of converting some aromatic compounds (e.g. biphenyl,p-xylene, m-xylene, o-xylene,1,2,3,4-tetrahydro-naphthalene) into the corresponding dichloromethyl-substituted aromatic compounds in good to excellent isolated yield. Mild reaction conditions, ease of workup, high yields, stability, easy isolation of the compounds, good thermoregulated biphasic behavior of IL, and excellent recyclability of the catalyst are the attractive features of this methodology, which is a good example of green chloromethylation method.
A simple, efficient, and environmentally friendly procedure for the amination of organic halides catalyzed by CuSO4·5H2O in PEG1000-DIL/methylcyclohexane temperature-dependent biphasic system has been developed. A wide range of aryl, benzylic, allylic, and aliphatic halides were found to be applicable to the catalytic system. This procedure include many advantages such as mild reaction conditions, simplicity of operation, high yields, easy isolation of products by a simple decantation, good thermoregulated biphasic behavior of the IL, and excellent recyclability of the catalytic system.
Three kinds of new PEGiooo-based dicationic acidic ionic liquids (PEG1000-DAIL[BF4], PEG1000-DAIL[PF6] and PEGiooo-DAIL[OTf]) have been synthesized from the ionic liquid PEGiooo-DAIL, and found that these ionic liquids can also exhibite good temperature-dependent phase behavior with toluene, and their applications in hydrolysis of organic halides, epoxides, and esters have been extensively studied. The results showed that Fe2(SO4)3was found to be the most effective cocatalyst in terms of yield and reaction rate in PEG1000-DAIL[BF4]/toluene temperature-dependen biphasic system. And the PEG1000-DAIL[BF4]/Fe2(SO4)3catalytic system was found to be more effective in hydrolysis of organic halides than that of both epoxides and esters. After the completion of the reaction, the phase-separation appeared along with cooling, and a complete oil-water biphasic system was formed again after being cooled to room temperature. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.
Nine kinds of new PEG1000-based dicationic ionic liquids based on transition metals (PEG1000-DAIL[CdCl3], PEG,ooo-DAIL[FeCl3], PEG1000-DAIL[FeCl4], PEG1000-DAIL[CuCl2], PEG1000-DAIL[CuCl3], PEG1000-DAIL[ZnCl3], PEG1000-DAIL[PdCl3], PEG1000-DAIL[MnCl3] and PEG1000-DAIL[AlCl4) have been synthesized from the ionic liquid PEG1000-DAIL, and found that these ionic liquids can also exhibite good temperature-dependent phase behavior with toluene, and their applications in C-O coupling of organic halides with phenols and alcohols have been extensively studied. The results showed that PEG1000-DAIL[CdCl3] demonstrated the best performance, and an experimentally simple and efficient protocol for the C-O coupling of organic halides with phenols and alcohols in PEG1000-DAIL[CdCl3]/toluene temperature-dependent biphasic system has been developed.
A series of ionic liquids of transition metals based on1-alkyl-3-methylimidazolium cation [Cnmim]+) as phase transfer catalysts were synthesized, and their applications in the selective oxidation of organic halides to aldehydes and ketones and reductive homocoupling of benzyl and aryl halides have been extensively studied. A simple, mild, and efficient procedure for the oxidation of organic halides to aldehydes and ketones with H5IO6in ionic liquid [C12mim][FeCl4] has been developed. The oxidation reactions afford the target products in good to high yields and no overoxidation was observed. The products can be separated by a simple extraction with organic solvent, and the catalytic system can be recycled and reused without loss of catalytic activity. A facile and efficient synthesis of bibenzyl and biaryl derivatives by reductive C-C homocoupling reaction has been described. Treatment of benzyl and aryl halides with metallic zinc and copper powder in the presence of a catalytic amount of [C12mim][CuCl2] under ligand-and base-free conditions gives the corresponding bibenzyls and biaryls in good to high yields. The product can be isolated by a simple extraction with organic solvent, and the advantages of our procedure include simplicity of operation, low cost, high yields, and excellent recyclability of the catalyst.
本课题主要研究了离子液体温控两相催化体系和离子液体相转移催化体系中芳烃化合物氯甲基化反应、胺解反应、水解反应、C-O偶联反应、氧化反应和还原C-C自偶联反应,以期开发出环境友好的新方法,具体的研究内容包括以下几个方面。
在实施芳烃化合物的氯甲基化反应中,分别研究了PEG1000-DAIL/甲基环己烷和PEG1000-DIL／甲基环己烷这两种离子液体温控两相催化体系对反应的影响规律。研究表明,PEG1000-DIL／甲基环己烷温控两相体系能够较好的催化芳烃化合物单氯甲基化反应；PEG1000-DAIL/甲基环己烷温控两相体系能更好的催化联苯、二甲苯和四氢萘的二氯甲基化反应,反应得到了一些对称的二氯甲基化产物。整个反应过程条件温和,选择性好,后处理简单,离子液体催化体系循环使用效果良好,实现了环境友好的氯甲基化反应。
以硫酸铜(CuS04)为催化剂,将PEG1000-DIL/甲基环己烷温控两相体系应用于有机卤化物的氨解反应。研究发现PEG1000-DIL/CuSO4催化体系可以高效的催化有机卤化物的氨解反应,反应收率在84%以上。反应选择性好,条件温和,操作简单,反应结束后产物相催化相易分离而且没有异构体生成,离子液体催化体系回收循环使用效果良好。
以酸性聚乙二醇型双子离子液体PEG1000-DAIL为基础合成了三种不同阴离子的离子液体PEG1000-DAIL[BF4],PEG1000-DAIL[PF6]和PEG1000-DAIL[OTf],发现了这三种离子液体都可以与甲苯形成良好的温控两相体系,并研究了它们在有机卤化物、环氧化合物和酯类化合物的水解反应。实验表明,采用Fe2(S04)3为辅助催化剂,在PEG1000-DAIL[BF4]/甲苯温控两相体系作用下,水解反应能够快速高效的进行。相对于环氧化合物和酯类化合物的催化水解反应过程,PEG1000-DAIL[BF4]/Fe2(SO4)3/甲苯温控两相催化体系能够更有效的催化有机卤化物的水解反应,反应速度更快。反应结束后,产物与催化体系形成油-水两相,通过简单的倾析便可实现产物与催化体系的分离。催化体系可以方便的回收循环使用而催化活性基本保持不变。
以PEG1000-DAIL为基础合成了一系列不同阴离子的过渡金属离子液体,这些离子液体可以与甲苯形成良好的温控两相体系。将所形成的温控两相体系应用于催化有机卤化物与醇和酚的C-O偶联反应,研究结果表明,过渡金属离子液体PEG1000-DAIL[CdCl3]/甲苯温控两相体系催化反应效果较好。
合成了一系列具有相转移催化性质的长链1-烷基-3-甲基咪唑盐过渡金属离子液体。分别研究了这些离子液体中有机卤化物的选择性氧化反应和有机卤化物的还原C-C自偶联反应。发明了一种新的[C12min][FeCl4]催化有机卤化物的选择性H5I06氧化体系,该体系能够有效的将一系列的有机卤化物选择性氧化为相应的醛或酮,并能高收率的得到氧化产品。离子液体催化剂可以方便的回收循环使用,反应条件温和,选择性好,操作简单,催化剂用量少,符合绿色化学的发展方向。发展了一种有效的还原C-C自偶联[C12mim][CuCl2]/Cu/Zn反应体系,该体系能够有效的将一系列苄基和芳基卤化物转化为相应的联苄和联苯类化合物,反应在无溶剂条件下进行,产品收率都在80%以上,反应选择性好,催化剂可以方便的回收循环使用,该工艺符合绿色化学的发展方向,具有良好的应用前景。
Recently, ionic liquids research has become a new field of green chemistry. Due to their favorable properties such as non-inflammability, negligible vapour pressure, reusability and high thermal stability, ionic liquid technology has been successfully applied to many areas of chemistry including organic and inorgnic synthesis, biphasic catalysis, separation proeesses, electrochemistry etc. Separation and recovery of catalyst with high efficiency plays an important role in green chemistry. Ionic liquids of catalytic system possess the thermoregulated biphasic behavior of "mono-phase under high temperature, bi-phase under room temperature" and phase transfter catalysis have been attracted much attention due to their advantages of both homogeneous and heterogeneous eatalysis with high product yield and the easy separation of product from catalytic system.
The main objective of this dissertation is to perform the chloromethylation of aromatic hydrocarbons, animation of organic halides, hydrolysis of organic halides、epoxides and esters, C-O coupling of organic halides, oxidation of organic halides, and the reductive homocoupling of benzyl and aryl halides in ionic liquids with a view to develop new environment-friendly methods, and the specific research contents include the following aspects.
Two temperature-dependent biphasic systems, PEG1000-DAIL/methylcyclohexane and PEG1000-DIL/methylcyclohexane, were used as isolated catalyst in the chloromethylation of aromatic hydrocarbons, and the effect of reaction conditions on the catalytic reaction was investigated. It was found that a new chloromethylation reaction system using PEG1000-DIL in combination with methylcyclohexane has been developed, which is capable of converting aromatic hydrocarbons into the corresponding mono-chloromethyl-substituted aromatic compounds in good to excellent isolated yield. And the new dichloromethylation reaction system using PEG1000-DA.IL in combination with methylcyclohexane has also been developed, which is capable of converting some aromatic compounds (e.g. biphenyl,p-xylene, m-xylene, o-xylene,1,2,3,4-tetrahydro-naphthalene) into the corresponding dichloromethyl-substituted aromatic compounds in good to excellent isolated yield. Mild reaction conditions, ease of workup, high yields, stability, easy isolation of the compounds, good thermoregulated biphasic behavior of IL, and excellent recyclability of the catalyst are the attractive features of this methodology, which is a good example of green chloromethylation method.
A simple, efficient, and environmentally friendly procedure for the amination of organic halides catalyzed by CuSO4·5H2O in PEG1000-DIL/methylcyclohexane temperature-dependent biphasic system has been developed. A wide range of aryl, benzylic, allylic, and aliphatic halides were found to be applicable to the catalytic system. This procedure include many advantages such as mild reaction conditions, simplicity of operation, high yields, easy isolation of products by a simple decantation, good thermoregulated biphasic behavior of the IL, and excellent recyclability of the catalytic system.
Three kinds of new PEGiooo-based dicationic acidic ionic liquids (PEG1000-DAIL[BF4], PEG1000-DAIL[PF6] and PEGiooo-DAIL[OTf]) have been synthesized from the ionic liquid PEGiooo-DAIL, and found that these ionic liquids can also exhibite good temperature-dependent phase behavior with toluene, and their applications in hydrolysis of organic halides, epoxides, and esters have been extensively studied. The results showed that Fe2(SO4)3was found to be the most effective cocatalyst in terms of yield and reaction rate in PEG1000-DAIL[BF4]/toluene temperature-dependen biphasic system. And the PEG1000-DAIL[BF4]/Fe2(SO4)3catalytic system was found to be more effective in hydrolysis of organic halides than that of both epoxides and esters. After the completion of the reaction, the phase-separation appeared along with cooling, and a complete oil-water biphasic system was formed again after being cooled to room temperature. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.
Nine kinds of new PEG1000-based dicationic ionic liquids based on transition metals (PEG1000-DAIL[CdCl3], PEG,ooo-DAIL[FeCl3], PEG1000-DAIL[FeCl4], PEG1000-DAIL[CuCl2], PEG1000-DAIL[CuCl3], PEG1000-DAIL[ZnCl3], PEG1000-DAIL[PdCl3], PEG1000-DAIL[MnCl3] and PEG1000-DAIL[AlCl4) have been synthesized from the ionic liquid PEG1000-DAIL, and found that these ionic liquids can also exhibite good temperature-dependent phase behavior with toluene, and their applications in C-O coupling of organic halides with phenols and alcohols have been extensively studied. The results showed that PEG1000-DAIL[CdCl3] demonstrated the best performance, and an experimentally simple and efficient protocol for the C-O coupling of organic halides with phenols and alcohols in PEG1000-DAIL[CdCl3]/toluene temperature-dependent biphasic system has been developed.
A series of ionic liquids of transition metals based on1-alkyl-3-methylimidazolium cation [Cnmim]+) as phase transfer catalysts were synthesized, and their applications in the selective oxidation of organic halides to aldehydes and ketones and reductive homocoupling of benzyl and aryl halides have been extensively studied. A simple, mild, and efficient procedure for the oxidation of organic halides to aldehydes and ketones with H5IO6in ionic liquid [C12mim][FeCl4] has been developed. The oxidation reactions afford the target products in good to high yields and no overoxidation was observed. The products can be separated by a simple extraction with organic solvent, and the catalytic system can be recycled and reused without loss of catalytic activity. A facile and efficient synthesis of bibenzyl and biaryl derivatives by reductive C-C homocoupling reaction has been described. Treatment of benzyl and aryl halides with metallic zinc and copper powder in the presence of a catalytic amount of [C12mim][CuCl2] under ligand-and base-free conditions gives the corresponding bibenzyls and biaryls in good to high yields. The product can be isolated by a simple extraction with organic solvent, and the advantages of our procedure include simplicity of operation, low cost, high yields, and excellent recyclability of the catalyst.
引文
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