用于烯烃硅氢加成反应铑配合物/离子液体催化剂体系的研究
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摘要
本论文针对现有烯烃和烷(氧)基氢硅烷硅氢加成反应体系存在的若干重要基础问题,如催化剂活性、加成产物的选择性、贵金属配合物催化剂循环利用等进行研究。将过渡金属铑配合物/离子液体(有机融盐)催化剂体系用于烯烃和烷(氧)基氢硅烷的硅氢加成反应,建立了催化剂结构、催化性能及循环使用性能之间的关系。
本论文首先将Rh(PPh_3)_3Cl/离子液体(有机融盐)催化剂体系用于烯烃和烷(氧)基氢硅烷的硅氢加成反应。研究发现离子液体的空间结构直接影响了β加成、加成产物的选择性。随着二烷基咪唑六氟磷酸盐、烷基吡啶六氟磷酸盐中咪唑、吡啶环上取代烷基空间位阻增大,β加成物/加成物的比值也随之增加。其中,用Rh(PPh_3)_3Cl/Bn_2ImPF_6催化苯乙烯和三乙氧基氢硅烷硅氢加成反应,β加成的选择性最高,为95.7%。
接着将离子液体固载到无机载体,进而制备得到Rh(PPh_3)_3Cl /离子液体功能化载体的负载型催化剂。用于催化烯烃和三乙氧基氢硅烷硅氢加成反应,可获得较高的反应转化率和β加成物的选择性。反应结束后,催化剂可以比较容易地与产物分离,重复再使用。其中Rh(PPh_3)_3Cl/ Rh(PPh_3)_3Cl/SiO_2-(CH_2CH_2CH_2)MimPF6催化剂重复使用性能最佳,回收使用10次后,其活性和β加成产物的选择性基本保持不变。
在本论文中,还制备了一系列2-咪唑膦配位的铑配合物,并将2-咪唑膦配位的铑配合物/离子液体催化剂体系用于烷(氧)基氢硅烷硅氢加成反应。利用咪唑环中的两个氮原子含有孤对电子,可通过π键向咪唑环中的2-位碳提供电子迁移,从而稳定Rh-P键,同时P原子上的电荷富集也可稳定中心金属Rh,进而稳定了Rh和底物形成的中间态,提高铑配合物的催化活性。当催化剂2-咪唑膦配位的Rh配合物的用量为苯乙烯用量的0.02mol%时,苯乙烯的转化率仍可>90.4%,β-加成产物的选择性>89.8%。
此外,本论文还首次将超临界CO_2/室温离子液体体系应用到烷(氧)基氢硅烷硅氢加成反应。利用超临界CO_2和室温离子液体二者之间的不对称的相溶性,反应物系可在相间实现所需的转移。过渡金属铑配合物仅溶于离子液体而不溶于超临界CO_2中,而离子液体相几乎不挥发,尽可能地避免了催化剂的流失。同时产物随着超临界CO_2离开反应体系,实现了催化剂重复使用。研究还发现,N-杂环铑卡宾配合物在超临界CO_2/室温离子液体两相介质中催化烯烃硅氢加成反应可有效地抑制烯烃加氢副反应的发生,如苯乙烯和烷(氧)基氢硅烷硅氢加成反应的产物中没有检测到苯乙烷。
In this paper, issues dealing with hydrosilylation of different olefins , such as activity of catalyst, selectivity of adduct, reuse of noble metal catalyst, were focused. It was founded the relation of the catalyst structure and activity or circulation by rhodium complex/ionic liquid (molten salt) as a catalytic system for the hydrosilylation of different olefins with trialkoxysilane (trialkylsiane).
Rh(PPh_3)_3Cl/ionic liquid (molten salt) as a thermoregulated and recyclable catalytic system for the hydrosilylation of different olefins with trialkoxysilane (trialkylsiane) have been investigated. N, N-dialkylimidazolium salts or N-alkylpyridinium salts can specifically vary their physical and chemical properties by altering the attached substituents, and it was found that both activity and selectivity of catalyst system could be influenced by the alkyl chains attached to the pyridinium or imidazolium cations. The ratio of theβ-adduct to the -adduct (β/ ) is clearly increased with increasing length of alkyl chain attached to the pyridinium or imidazolium cations. And hydrosilylation reaction of styrene with triethoxysilane was conducted by Rh(PPh_3)_3Cl/Bn_2ImPF_6. The Rh(PPh_3)_3Cl/Bn_2ImPF_6 showed the highest conversion of styrene, 95.7%。
Along with research to minimize the amount of ionic liquid and noble metal catalyst in hydrosilylation processes, this paper reported in the present study that ionic liquid (IL)-functionalized SiO_2 can be prepared by a one-step procedure. The Rh(PPh_3)_3Cl was then supported on the IL-functionalized SiO_2 to obtain the Rh(PPh_3)_3Cl/IL-functionalized SiO_2 catalyst. Subsequently, the hydrosilylation of styrene and -olefins with triethoxysilane catalyzed with this supported catalyst was investigated. Furthermore, the catalyst system could be recovered easily. For example, the Rh(PPh_3)_3Cl/SiO_2-(CH_2CH_2CH_2)MimPF6 catalyst system could be recovered easily and reused more than 10 times without any notable loss of catalytic activity or selectivity.
A series of rhodium complexes employing 2-imidazolium phosphines as ligands synthesized exhibited greater catalytic activity and selectivity for hydrosilylation of different olefins with trialkoxysilane (trialkylsiane). The electron-rich heterocycle provides a suitable framework that stabilizes the Rh-phosphine center located between the two nitrogen atoms. It is possible that close proximity of the positive charge to the phosphorus atom greatly enhances the catalytic activity and can afford highly efficient catalytic activity. When amounts of rhodium complexes employing 2-imidazolium phosphines as ligands were 0.02mol% of styrene, the conversion of styrene were >90.4%,the selectivity ofβ-adduct were >89.8%.
The hydrosilylation of alkenes in a supercritical CO_2 (scCO_2) /ionic liquid system was first investigated. scCO_2 can be used to extract high boiling point organic substances from ILs without cross-contamination. During hydrosilylation in the scCO_2/IL system, the reactants were possibly transferred into the IL phase by scCO_2, in which the catalyst was dissolved. The products can be flushed with scCO_2 after the reaction and the catalyst/IL system reused. During a new hydrosilylation process in a scCO_2/IL system with a rhodium complex as the catalyst process, rhodium complexes of NHC were formed by direct carboxylation of 1,3-dialkylimidazolium hexafluorophosphate with CO_2 in situ. Herein, It was found that both the catalytic activity and selectivity of the rhodium complexes bearing NHC ligands were influenced by the attached substituents of the imidazolium cation, and no hydrogenation by-product (alkane) was detected.
本论文首先将Rh(PPh_3)_3Cl/离子液体(有机融盐)催化剂体系用于烯烃和烷(氧)基氢硅烷的硅氢加成反应。研究发现离子液体的空间结构直接影响了β加成、加成产物的选择性。随着二烷基咪唑六氟磷酸盐、烷基吡啶六氟磷酸盐中咪唑、吡啶环上取代烷基空间位阻增大,β加成物/加成物的比值也随之增加。其中,用Rh(PPh_3)_3Cl/Bn_2ImPF_6催化苯乙烯和三乙氧基氢硅烷硅氢加成反应,β加成的选择性最高,为95.7%。
接着将离子液体固载到无机载体,进而制备得到Rh(PPh_3)_3Cl /离子液体功能化载体的负载型催化剂。用于催化烯烃和三乙氧基氢硅烷硅氢加成反应,可获得较高的反应转化率和β加成物的选择性。反应结束后,催化剂可以比较容易地与产物分离,重复再使用。其中Rh(PPh_3)_3Cl/ Rh(PPh_3)_3Cl/SiO_2-(CH_2CH_2CH_2)MimPF6催化剂重复使用性能最佳,回收使用10次后,其活性和β加成产物的选择性基本保持不变。
在本论文中,还制备了一系列2-咪唑膦配位的铑配合物,并将2-咪唑膦配位的铑配合物/离子液体催化剂体系用于烷(氧)基氢硅烷硅氢加成反应。利用咪唑环中的两个氮原子含有孤对电子,可通过π键向咪唑环中的2-位碳提供电子迁移,从而稳定Rh-P键,同时P原子上的电荷富集也可稳定中心金属Rh,进而稳定了Rh和底物形成的中间态,提高铑配合物的催化活性。当催化剂2-咪唑膦配位的Rh配合物的用量为苯乙烯用量的0.02mol%时,苯乙烯的转化率仍可>90.4%,β-加成产物的选择性>89.8%。
此外,本论文还首次将超临界CO_2/室温离子液体体系应用到烷(氧)基氢硅烷硅氢加成反应。利用超临界CO_2和室温离子液体二者之间的不对称的相溶性,反应物系可在相间实现所需的转移。过渡金属铑配合物仅溶于离子液体而不溶于超临界CO_2中,而离子液体相几乎不挥发,尽可能地避免了催化剂的流失。同时产物随着超临界CO_2离开反应体系,实现了催化剂重复使用。研究还发现,N-杂环铑卡宾配合物在超临界CO_2/室温离子液体两相介质中催化烯烃硅氢加成反应可有效地抑制烯烃加氢副反应的发生,如苯乙烯和烷(氧)基氢硅烷硅氢加成反应的产物中没有检测到苯乙烷。
In this paper, issues dealing with hydrosilylation of different olefins , such as activity of catalyst, selectivity of adduct, reuse of noble metal catalyst, were focused. It was founded the relation of the catalyst structure and activity or circulation by rhodium complex/ionic liquid (molten salt) as a catalytic system for the hydrosilylation of different olefins with trialkoxysilane (trialkylsiane).
Rh(PPh_3)_3Cl/ionic liquid (molten salt) as a thermoregulated and recyclable catalytic system for the hydrosilylation of different olefins with trialkoxysilane (trialkylsiane) have been investigated. N, N-dialkylimidazolium salts or N-alkylpyridinium salts can specifically vary their physical and chemical properties by altering the attached substituents, and it was found that both activity and selectivity of catalyst system could be influenced by the alkyl chains attached to the pyridinium or imidazolium cations. The ratio of theβ-adduct to the -adduct (β/ ) is clearly increased with increasing length of alkyl chain attached to the pyridinium or imidazolium cations. And hydrosilylation reaction of styrene with triethoxysilane was conducted by Rh(PPh_3)_3Cl/Bn_2ImPF_6. The Rh(PPh_3)_3Cl/Bn_2ImPF_6 showed the highest conversion of styrene, 95.7%。
Along with research to minimize the amount of ionic liquid and noble metal catalyst in hydrosilylation processes, this paper reported in the present study that ionic liquid (IL)-functionalized SiO_2 can be prepared by a one-step procedure. The Rh(PPh_3)_3Cl was then supported on the IL-functionalized SiO_2 to obtain the Rh(PPh_3)_3Cl/IL-functionalized SiO_2 catalyst. Subsequently, the hydrosilylation of styrene and -olefins with triethoxysilane catalyzed with this supported catalyst was investigated. Furthermore, the catalyst system could be recovered easily. For example, the Rh(PPh_3)_3Cl/SiO_2-(CH_2CH_2CH_2)MimPF6 catalyst system could be recovered easily and reused more than 10 times without any notable loss of catalytic activity or selectivity.
A series of rhodium complexes employing 2-imidazolium phosphines as ligands synthesized exhibited greater catalytic activity and selectivity for hydrosilylation of different olefins with trialkoxysilane (trialkylsiane). The electron-rich heterocycle provides a suitable framework that stabilizes the Rh-phosphine center located between the two nitrogen atoms. It is possible that close proximity of the positive charge to the phosphorus atom greatly enhances the catalytic activity and can afford highly efficient catalytic activity. When amounts of rhodium complexes employing 2-imidazolium phosphines as ligands were 0.02mol% of styrene, the conversion of styrene were >90.4%,the selectivity ofβ-adduct were >89.8%.
The hydrosilylation of alkenes in a supercritical CO_2 (scCO_2) /ionic liquid system was first investigated. scCO_2 can be used to extract high boiling point organic substances from ILs without cross-contamination. During hydrosilylation in the scCO_2/IL system, the reactants were possibly transferred into the IL phase by scCO_2, in which the catalyst was dissolved. The products can be flushed with scCO_2 after the reaction and the catalyst/IL system reused. During a new hydrosilylation process in a scCO_2/IL system with a rhodium complex as the catalyst process, rhodium complexes of NHC were formed by direct carboxylation of 1,3-dialkylimidazolium hexafluorophosphate with CO_2 in situ. Herein, It was found that both the catalytic activity and selectivity of the rhodium complexes bearing NHC ligands were influenced by the attached substituents of the imidazolium cation, and no hydrogenation by-product (alkane) was detected.
引文
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