以羟基茚满酮亚胺为配体的配合物的合成及其催化烯烃聚合的研究
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摘要
本论文首先合成了一系列羟基茚满酮亚胺配体,然后利用它们和各种金属源的反应制备、表征了一系列以镍、铜和钛为中心离子的过渡金属配合物,探讨了这些配合物在助催化剂的作用下催化烯烃和极性单体聚合的反应行为。
1.通过羟基茚满酮和苯胺或2,6-二异丙基苯胺的酮胺缩合反应,制备了一系列的羟基茚满酮亚胺配体。
2.合成了6个基于羟基茚满酮亚胺配体的新型镍(Ⅱ)配合物,其中3个是三核配合物,3个单核配合物,并解析其中四个配合物的单晶结构。在助催化剂MAO的活化下,它们能以很高的活性(2.55×10~7 gPNBmol~(-1)Nih~(-1))催化降冰片烯进行加成聚合,得到高分子量的低立构规整性的聚降冰片烯。系统地研究了催化剂的结构、MAO用量和聚合反应温度等因素对配合物的催化活性和聚合所得聚降冰片烯的分子量的影响。
3.借助于助催化剂MAO的作用,以羟基茚满酮亚胺为配体的新型镍(Ⅱ)配合物可以10~4 gPMMAmol~(-1)Nih~(-1)的活性催化甲基丙烯酸甲酯聚合,所得聚甲基丙烯酸甲酯的数均分子量的数量级在10~4 gmol~(-1),分子量分布相对较宽(M_w/M_n=4-7),间规三元组rr的含量在60-80%。系统地研究了催化剂的结构、MAO用量和聚合反应温度等因素对配合物的催化活性和聚合物的分子量及微观结构的影响。
4.在助催化剂MAO的作用下,单核镍(Ⅱ)配合物能以10~4 gPSmol~(-1)Nih~(-1)的活性催化苯乙烯聚合,所得聚苯乙烯的数均分子量在10~4 gmol~(-1),分子量分布在2左右,等规三元组mm的含量在50-60%。系统地研究了催化剂的结构、MAO用量和聚合反应温度等因素对配合物的催化活性和聚合物的分子量及微观结构的影响。利用聚合物的~(13)C NMR谱图讨论了苯乙烯聚合的机理,认为是配位聚合的机理。
5.合成了三个基于羟基茚满酮亚胺配体的单核铜配合物,而且得到了其中一个配合物的同质多晶异构体。通过X-射线衍射解析了它们的单晶结构,它们都为四配位N_2O_2结构,铜为完全平面或扭曲平面结构。在助催化剂MAO的作用下,它们能以最高为1.10×10~5 gPNBmol~(-1)Cuh~(-1)的活性催化降冰片烯进行加成聚合,所得聚降冰片烯的粘均分子量在10~6 gmol~(-1)。酚羟基对位的取代基的电子效应对催化剂的催化活性有较大的影响,变化序列是1(CH_3)＞2(H)＞3(Cl)。系统地研究了助催化剂MAO用量和聚合反应温度等因素对配合物的催化活性和聚合物的分子量的影响。
6.合成了一个三核钛配合物,通过X-射线衍射表征了其单晶结构。在助催化剂MAO的作用下,能以中等活性(0.14-2.55×10~5 gPEmol~(-1) Tih~(-1))催化乙烯常压聚合,得到相对分子量范围在35-186万之间变化的高分子量和超高分子量聚乙烯。助催化剂MAO用量和聚合反应温度等因素可以控制配合物的催化活性和聚合物的分子量。
In this dissertation,a series of complexes with hydroxyindanone-imine ligands have been synthesized and characterized,which included early transition metal complexes based on titanium and late transition metal complexes based on nickel and copper.And catalytic behavior of these complexes as catalysts for polymerization of olefins and polar monomers was investigated.The full dissertation was summarized as follows:
1.A series of new hydroxyindanone-imine ligands were synthesized by the condensation reaction of hydroxyindanone and corresponding aniline under acidic condition.
2.A series of Ni(Ⅱ) complexes beating hydroxyindanone-imine ligands had been synthesized and characterized.The X-ray structure analyses clearly indicate that Ni(Ⅱ) complexes bearing ligand without substituted groups on aniline are octahedral and trimeric,while Ni(Ⅱ) complexes bearing ligand containing more bulkly N-2,6-diisopropylphenyl moiety are mononuclear with a square planar N_2O_2 coordination geometry.Activated with methylaluminoxane(MAO),these Ni(Ⅱ) complexes can promote the addition polymerization of norbornene(NB) with very high activities(up to 10~7 gPNBmol~(-1)Nih~(-1)) to obtain the polynorbornene(PNB) with high molecular weights (10~6 gmol~(-1)),low stereoregularity and high heat stability.The effects of catalyst structures, polymerization conditions such as Al/Ni molar ratio,reaction temperature,and the concentration of catalyst and monomer on norbornene polymerization behavior had been discussed in detail.
3.Activated with MAO,these Ni(Ⅱ) complexes we firstly prepared can also polymerize methyl methacrylate(MMA) containing polar ester group,producing syndiotactic-rich poly(methyl methacrylate)(PMMA)(rr up to 80%) with relatively wide molecular weight distribution(M_w/M_n=4-7).And the influence of catalyst structures and polymerization conditions on catalytic activities of Ni(Ⅱ) complexes and the microstructure of PMMA had been discussed in detail.
4.After activation with MAO,these Ni(Ⅱ) complexes are also capable of catalyzing the polymerization of styrene to obtain isotactic-rich polystyrene(PS)(mm up to 60%). The molecular weight distributions of polymer are around 2 which indicated the presence of single active site during the polymerization reaction.And the effects of catalyst structures and polymerization conditions on catalytic activities of Ni(Ⅱ) complexes and the microstructure of PS had been discussed in detail.According to the analysis of ~(13)C NMR spectra of obtained polymer,the polymerization proceeds through a coordination mechanism,which was supported by the structure of dimmer of styrene obtained in the low Al/Ni ratio.
5.A series of Cu(Ⅱ) complexes beating hydroxyindanone-imine ligands had been synthesized and characterized.X-ray structures reveal that Cu(Ⅱ) complexes adopt a square planar or distorted square planar N_2O_2 coordination geometry.The moderate catalytic activities(up to 10~5 gPNBmol~(-1)Cuh~(-1)) for the addition polymerization of norbornene have been provided by them at the activation of MAO.The polymers with high molecular weights(10~6 gmol~(-1)),low stereoregularity and high heat stability were obtained.At the similar reaction condition,the catalytic activities change in descending order R=Me＞H＞Cl.The effects of polymerization conditions such as Al/Cu molar ratio and reaction temperature on norbornene polymerization behavior had been discussed in detail.
6.A trinuclear titanium complex beating hydroxyindanone-imine and cyclopentadienyl ligand had been synthesized and characterized.After activation with MAO, the complex can polymerize polymerization of ethylene with moderate catalytic activities (up to 10~5 gPEmol~(-1)Tih~(-1)).The molecular weights of polyethylene(PE) ranged from 35×10~4 gmol~(-1) to 186×10~4 gmol~(-1),which suggests the production of high to ultrahigh molecular weight polyethylene.The effects of polymerization conditions such as Al/Ti molar ratio and reaction temperature on catalytic activities of complex and the molecular weights of PE had been discussed in detail.
1.通过羟基茚满酮和苯胺或2,6-二异丙基苯胺的酮胺缩合反应,制备了一系列的羟基茚满酮亚胺配体。
2.合成了6个基于羟基茚满酮亚胺配体的新型镍(Ⅱ)配合物,其中3个是三核配合物,3个单核配合物,并解析其中四个配合物的单晶结构。在助催化剂MAO的活化下,它们能以很高的活性(2.55×10~7 gPNBmol~(-1)Nih~(-1))催化降冰片烯进行加成聚合,得到高分子量的低立构规整性的聚降冰片烯。系统地研究了催化剂的结构、MAO用量和聚合反应温度等因素对配合物的催化活性和聚合所得聚降冰片烯的分子量的影响。
3.借助于助催化剂MAO的作用,以羟基茚满酮亚胺为配体的新型镍(Ⅱ)配合物可以10~4 gPMMAmol~(-1)Nih~(-1)的活性催化甲基丙烯酸甲酯聚合,所得聚甲基丙烯酸甲酯的数均分子量的数量级在10~4 gmol~(-1),分子量分布相对较宽(M_w/M_n=4-7),间规三元组rr的含量在60-80%。系统地研究了催化剂的结构、MAO用量和聚合反应温度等因素对配合物的催化活性和聚合物的分子量及微观结构的影响。
4.在助催化剂MAO的作用下,单核镍(Ⅱ)配合物能以10~4 gPSmol~(-1)Nih~(-1)的活性催化苯乙烯聚合,所得聚苯乙烯的数均分子量在10~4 gmol~(-1),分子量分布在2左右,等规三元组mm的含量在50-60%。系统地研究了催化剂的结构、MAO用量和聚合反应温度等因素对配合物的催化活性和聚合物的分子量及微观结构的影响。利用聚合物的~(13)C NMR谱图讨论了苯乙烯聚合的机理,认为是配位聚合的机理。
5.合成了三个基于羟基茚满酮亚胺配体的单核铜配合物,而且得到了其中一个配合物的同质多晶异构体。通过X-射线衍射解析了它们的单晶结构,它们都为四配位N_2O_2结构,铜为完全平面或扭曲平面结构。在助催化剂MAO的作用下,它们能以最高为1.10×10~5 gPNBmol~(-1)Cuh~(-1)的活性催化降冰片烯进行加成聚合,所得聚降冰片烯的粘均分子量在10~6 gmol~(-1)。酚羟基对位的取代基的电子效应对催化剂的催化活性有较大的影响,变化序列是1(CH_3)＞2(H)＞3(Cl)。系统地研究了助催化剂MAO用量和聚合反应温度等因素对配合物的催化活性和聚合物的分子量的影响。
6.合成了一个三核钛配合物,通过X-射线衍射表征了其单晶结构。在助催化剂MAO的作用下,能以中等活性(0.14-2.55×10~5 gPEmol~(-1) Tih~(-1))催化乙烯常压聚合,得到相对分子量范围在35-186万之间变化的高分子量和超高分子量聚乙烯。助催化剂MAO用量和聚合反应温度等因素可以控制配合物的催化活性和聚合物的分子量。
In this dissertation,a series of complexes with hydroxyindanone-imine ligands have been synthesized and characterized,which included early transition metal complexes based on titanium and late transition metal complexes based on nickel and copper.And catalytic behavior of these complexes as catalysts for polymerization of olefins and polar monomers was investigated.The full dissertation was summarized as follows:
1.A series of new hydroxyindanone-imine ligands were synthesized by the condensation reaction of hydroxyindanone and corresponding aniline under acidic condition.
2.A series of Ni(Ⅱ) complexes beating hydroxyindanone-imine ligands had been synthesized and characterized.The X-ray structure analyses clearly indicate that Ni(Ⅱ) complexes bearing ligand without substituted groups on aniline are octahedral and trimeric,while Ni(Ⅱ) complexes bearing ligand containing more bulkly N-2,6-diisopropylphenyl moiety are mononuclear with a square planar N_2O_2 coordination geometry.Activated with methylaluminoxane(MAO),these Ni(Ⅱ) complexes can promote the addition polymerization of norbornene(NB) with very high activities(up to 10~7 gPNBmol~(-1)Nih~(-1)) to obtain the polynorbornene(PNB) with high molecular weights (10~6 gmol~(-1)),low stereoregularity and high heat stability.The effects of catalyst structures, polymerization conditions such as Al/Ni molar ratio,reaction temperature,and the concentration of catalyst and monomer on norbornene polymerization behavior had been discussed in detail.
3.Activated with MAO,these Ni(Ⅱ) complexes we firstly prepared can also polymerize methyl methacrylate(MMA) containing polar ester group,producing syndiotactic-rich poly(methyl methacrylate)(PMMA)(rr up to 80%) with relatively wide molecular weight distribution(M_w/M_n=4-7).And the influence of catalyst structures and polymerization conditions on catalytic activities of Ni(Ⅱ) complexes and the microstructure of PMMA had been discussed in detail.
4.After activation with MAO,these Ni(Ⅱ) complexes are also capable of catalyzing the polymerization of styrene to obtain isotactic-rich polystyrene(PS)(mm up to 60%). The molecular weight distributions of polymer are around 2 which indicated the presence of single active site during the polymerization reaction.And the effects of catalyst structures and polymerization conditions on catalytic activities of Ni(Ⅱ) complexes and the microstructure of PS had been discussed in detail.According to the analysis of ~(13)C NMR spectra of obtained polymer,the polymerization proceeds through a coordination mechanism,which was supported by the structure of dimmer of styrene obtained in the low Al/Ni ratio.
5.A series of Cu(Ⅱ) complexes beating hydroxyindanone-imine ligands had been synthesized and characterized.X-ray structures reveal that Cu(Ⅱ) complexes adopt a square planar or distorted square planar N_2O_2 coordination geometry.The moderate catalytic activities(up to 10~5 gPNBmol~(-1)Cuh~(-1)) for the addition polymerization of norbornene have been provided by them at the activation of MAO.The polymers with high molecular weights(10~6 gmol~(-1)),low stereoregularity and high heat stability were obtained.At the similar reaction condition,the catalytic activities change in descending order R=Me＞H＞Cl.The effects of polymerization conditions such as Al/Cu molar ratio and reaction temperature on norbornene polymerization behavior had been discussed in detail.
6.A trinuclear titanium complex beating hydroxyindanone-imine and cyclopentadienyl ligand had been synthesized and characterized.After activation with MAO, the complex can polymerize polymerization of ethylene with moderate catalytic activities (up to 10~5 gPEmol~(-1)Tih~(-1)).The molecular weights of polyethylene(PE) ranged from 35×10~4 gmol~(-1) to 186×10~4 gmol~(-1),which suggests the production of high to ultrahigh molecular weight polyethylene.The effects of polymerization conditions such as Al/Ti molar ratio and reaction temperature on catalytic activities of complex and the molecular weights of PE had been discussed in detail.
引文
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