高碳烯烃氢甲酰化铑膦配合物催化剂的制备研究
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摘要
烯烃氢甲酰化反应由于其重要的工业应用背景和代表性的配位络合催化化学学术意义，一直是均相催化乃至多相催化领域备受重视的研究课题之一。本学位论文以高碳烯烃氢甲酰化反应为研究对象，以开拓新型催化剂体系为研究目的，获得如下主要进展。
1、通过邻二苯基苯甲醛与不同烷基胺的还原胺化，合成了5个胺基膦双齿配体；除此之外，在合成了十六烷基二苯基膦和3个烷基取代的三苯基膦基础上，进而制备了5个水溶性膦配体。对所合成配体的结构、物理化学性质及与铑配位化学进行较系统的研究。
2、处于苯环邻位的胺膦配位原子可与铑形成双齿配合物，其氢甲酰化反应活性随着烷基链的增长而降低，反应体系中引入适量的水则有利于提高配合物催化活性。采用三胺基单膦为配体，在一定程度上可实现pH值调控的催化剂循环使用。
3、所合成的水溶性新配体的水溶液表现出明显的表面活性性质。采用适当的P／Rh比，可获得较高的活性和选择性；个别水溶性铑配合物还表现出较好的催化性能稳定性。
4、水溶性铑配合物的催化性能与离子液体和水溶性配体结构、铑配合物的溶解度等密切相关。通过对离子液体和配体结构调变及反应条件优化，可使水溶性铑配合物在离子液体中表现出较高的氢甲酰化性能，并且反应后催化剂与产物自动分层，从而实现催化剂多次循环使用。
5、苯环上含叔丁基的三苯基膦-铑配合物在均相氢甲酰化反应中，表现出明显的配位锥角效应，获得较好的正构醛选择性；由此固载于胺基官能团化介孔分子筛载体后，胺基和配合物之间发生明显的相互作用，获得高分散负载型铑膦配合物催化剂，表现出与均相体系类似的配位锥角效应和催化性能，并具有较好的稳定性。
The present dissertation sets the hydroformylation of higher olefins as the object of study. Works have been focused on the development of novel catalyst system. The significant results are described as follows:
1. A series of bidentate P,N ligands were synthesized by reductive amination with 2-(diphenylphosphino)benzaldehyde and different alkyl-amines; On the other hand, on the basis of successful syntheses of a linear chain alkyl(diphenyl)phosphine and three alkyl-substituted triphenylphsophines, a series of amphiphilic phosphines were prepared with oleum in high yields. The structures and physical-chemical properties of the above ligands and their rhodium complexes were characterized systemically.
2. The coordination of phosphine and nitrogen atoms with rhodium was observed by using the bidentate P,N ligands. The shorter of the chain in the structure of P,N ligand, the higher activity of 1-hexene hydroformlylation with aminophosphine rhodium complexes. The addition of appropriate water to the catalyst system caused a rate enhancement for the hydroformylation of 1-hexene. The tri-o-amino phosphine rhodium complex could be recycled to a certain extent by setting proper pH value after reaction.
3. The aqueous phosphine ligands were found to be of typical surfactants and micelle effects. A higher activity along with a higher selectivity to normal aldehyde was achieved with a proper L/Rh ratio. No significant losses in the catalystic performances were observed for several consecutive runs with the catalyst generated from the better hydrophilic phosphine.
4. It was found that the aqueous phosphine-rhodium complexes showed higher activity of 1-hexen hydroformylation in the media of hydrophilic ionic liquid coupled with suitable reaction conditions. The catalyst could be readily reused for several times through the phase separation after the reaction.
5. The rhodium complexes generated from terr-butyl group(s) substituted triphenylphosphines showed cone angle effect for normal aldehyde in homogeneous system. Such Rh-P complexes could be uniformly and highly dispersed at the surfaces of amino-functionalized mesoporous silicas due to the chemical interaction between the surface amino-groups and the Rh-P complexes. Besides the good stability, the heterogenized catalysts afforded the catalytic activity and cone angle effect comparable to those of the corresponding homogeneous ones.
1、通过邻二苯基苯甲醛与不同烷基胺的还原胺化，合成了5个胺基膦双齿配体；除此之外，在合成了十六烷基二苯基膦和3个烷基取代的三苯基膦基础上，进而制备了5个水溶性膦配体。对所合成配体的结构、物理化学性质及与铑配位化学进行较系统的研究。
2、处于苯环邻位的胺膦配位原子可与铑形成双齿配合物，其氢甲酰化反应活性随着烷基链的增长而降低，反应体系中引入适量的水则有利于提高配合物催化活性。采用三胺基单膦为配体，在一定程度上可实现pH值调控的催化剂循环使用。
3、所合成的水溶性新配体的水溶液表现出明显的表面活性性质。采用适当的P／Rh比，可获得较高的活性和选择性；个别水溶性铑配合物还表现出较好的催化性能稳定性。
4、水溶性铑配合物的催化性能与离子液体和水溶性配体结构、铑配合物的溶解度等密切相关。通过对离子液体和配体结构调变及反应条件优化，可使水溶性铑配合物在离子液体中表现出较高的氢甲酰化性能，并且反应后催化剂与产物自动分层，从而实现催化剂多次循环使用。
5、苯环上含叔丁基的三苯基膦-铑配合物在均相氢甲酰化反应中，表现出明显的配位锥角效应，获得较好的正构醛选择性；由此固载于胺基官能团化介孔分子筛载体后，胺基和配合物之间发生明显的相互作用，获得高分散负载型铑膦配合物催化剂，表现出与均相体系类似的配位锥角效应和催化性能，并具有较好的稳定性。
The present dissertation sets the hydroformylation of higher olefins as the object of study. Works have been focused on the development of novel catalyst system. The significant results are described as follows:
1. A series of bidentate P,N ligands were synthesized by reductive amination with 2-(diphenylphosphino)benzaldehyde and different alkyl-amines; On the other hand, on the basis of successful syntheses of a linear chain alkyl(diphenyl)phosphine and three alkyl-substituted triphenylphsophines, a series of amphiphilic phosphines were prepared with oleum in high yields. The structures and physical-chemical properties of the above ligands and their rhodium complexes were characterized systemically.
2. The coordination of phosphine and nitrogen atoms with rhodium was observed by using the bidentate P,N ligands. The shorter of the chain in the structure of P,N ligand, the higher activity of 1-hexene hydroformlylation with aminophosphine rhodium complexes. The addition of appropriate water to the catalyst system caused a rate enhancement for the hydroformylation of 1-hexene. The tri-o-amino phosphine rhodium complex could be recycled to a certain extent by setting proper pH value after reaction.
3. The aqueous phosphine ligands were found to be of typical surfactants and micelle effects. A higher activity along with a higher selectivity to normal aldehyde was achieved with a proper L/Rh ratio. No significant losses in the catalystic performances were observed for several consecutive runs with the catalyst generated from the better hydrophilic phosphine.
4. It was found that the aqueous phosphine-rhodium complexes showed higher activity of 1-hexen hydroformylation in the media of hydrophilic ionic liquid coupled with suitable reaction conditions. The catalyst could be readily reused for several times through the phase separation after the reaction.
5. The rhodium complexes generated from terr-butyl group(s) substituted triphenylphosphines showed cone angle effect for normal aldehyde in homogeneous system. Such Rh-P complexes could be uniformly and highly dispersed at the surfaces of amino-functionalized mesoporous silicas due to the chemical interaction between the surface amino-groups and the Rh-P complexes. Besides the good stability, the heterogenized catalysts afforded the catalytic activity and cone angle effect comparable to those of the corresponding homogeneous ones.
引文
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