非茂稀土金属配合物的合成及其催化烯烃聚合反应
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摘要
在过去十几年中,稀土金属配合物的研究得到了快速的发展,尤其是在催化乙烯、苯乙烯和共轭二烯的均聚和共聚方面取得了一系列令人瞩目的成果。然而,采用稀土金属体系催化α-烯烃聚合的研究较少,而且大多存在活性较低、所得聚合物分子量不高等缺点。与茂金属配合物相比,非茂金属配合物具有种类丰富、配体合成和修饰简单等特点,是烯烃聚合催化剂研究的重要组成部分。本文开发了三类基于非茂稀土金属配合物的烯烃聚合体系,并详细研究了它们对a-烯烃和异戊二烯的聚合性能。主要研究内容如下：
(1)基于氮杂环卡宾配体合成和修饰简单、配位能力强的特点,设计合成了三类氮杂环卡宾配位的稀土金属烷基化物。经过2倍当量有机硼盐活化,大位阻氮杂环卡宾配位的三烷基钪配合物能够高活性引发α-烯烃聚合,表明强供电子能力的氮杂环卡宾配体能够很好地稳定催化活性物种。该体系也能够催化1-己烯与1,5-己二烯共聚,所得共聚物中1,5-己二烯环化程度很高,两种单体单元的比例可以通过改变加料比方便的调控。并且随着共聚物中1,5-己二烯单元含量的增加,共聚物的玻璃化转变温度成线性增加。此外,通过核磁共振跟踪表明,氮杂环卡宾配位的单烷基钪二价阳离子为催化活性物种。
(2)设计开发了一类基于三氯化钪的简单Ziegler-Natta催化体系,能够在室温下中等活性催化1-己烯聚合,得到高分子量(>100万)和完全等规结构的聚1-己烯(mmmm>99%)。该体系具有良好的热稳定性和立体选择性,在80℃高温条件下,也能够得到高等规度的聚1-己烯(mmmm=97.3％).这是迄今为止稀土金属催化体系在高温下得到的最高值。中心金属的种类对催化性能起决定性作用,当采用其他几种稀土金属氯化物时,相同条件下不能催化1-己烯聚合。烷基铝和有机硼盐的种类对催化体系的活性和立体选择性都有影响：催化剂中配位基团的种类对催化活性影响较大,但是对立体选择性影响不大。单体碳链的长度对所得聚合物立体选择性影响较大,当单体碳链长度大于等于6时,所得聚合物具有完全等规结构。
(3)设计合成了一系列NCN-钳形双嗯唑啉稀土金属氯化物,配合物分子具有C2对称结构。在烷基铝和有机硼盐共同作用下,该类配合物能够高活性催化异戊二烯聚合,所得聚合物具有较高的顺式-1,4结构(最高可达99.5%)。聚合物分子量随单体与催化剂比例的增加而成比例增大,说明了该催化体系的单活性中心的特征。该体系的催化活性随着中心金属离子半径的增大而增加。烷基铝试剂的种类对催化活性和聚合的选择性都有影响；有机硼盐的种类对催化活性亦有影响,而对聚合的选择性影响不大。此外,在80℃高温条件下,该催化体系表现了良好的热稳定性和定向聚合能力,能够催化得到顺式-1,4结构含量大于96%的聚异戊二烯。通过核磁共振波谱、红外光谱等分析手段表明,含有配体的烷基桥连稀土-铝双核离子对为催化活性物种。
Rare-earth-metal complexes were booming for their superior catalytic behavior in polymerizations of ethylene, styrene, or conjugated dienes in the past decade. However, only limited catalyst systems have been used for polymerization of-olefins. Most of them exhibited low formation rates for polymers with low molecular weight. Compared with cyclopentadienyl complexes, the non-cyclopentadienyl complexes, which could be easily prepared and modified in ligand structures, have been widely applied to olefm polymerization. In this thesis, three kinds of rare-earth-metal catalyst systems with non-cyclopentadienyl ligands were developed. Also, their catalytic behaviors were detailed for (co)polymerization of α-olefins or isoprene. The results are summarized as followings:
(1) N-heterocyclic carbenes (NHC) are an ideal ligand for coordinating to rare-earth metals, due to their strong σ-donating ability. Trialkyl rare-earth-metal complexes bearing three kinds of NHC ligands were designed and synthesized. Upon activation with two equivalents of [Ph3C][B(C6Fs)4], the scandium complexes with sterically hindered NHC ligands exhibited high activities for a-olefin polymerization, demonstrating that the NHC ligand is capable of stabilizing the presumed cationic active species. The catalyst systems with trialkyl scandium complexes also conducted copolymerization of1-hexene (H) with1,5-hexadiene (HD) to give random atactic H/HD copolymers with a wide range of HD contents(26.6-98.6mol%), a previously unreported copolymer. The cyclization selectivity of the copolymerization is very high. An increase of the HD content in copolymers results in an obvious change of Tg of the copolymers. The Tg value is proportional to the HD content in the copolymer. According to the in situ NMR monitoring, the active species was proposed to be the dicationic complex.
(2) A simple Ziegler-Natta catalyst system based on ScCl3was developed. The system could conduct highly isospecific polymerization of1-hexene (mmmm>99%), and the resultant polymers possess high molecular weight(～106). This system proved to be showed an excellent stereoselectivity(mmmm>97%) even at80℃, the highest record for this polymerization at elevated temperatures. The activity showed a strong dependence on the central metal type. Replacing ScCl3(THF)3with YC13(THF)3.5, LaCl3(THF)2or LuCl3(THF)3resulted in nearly complete loss in activity for1-hexene polymerization. The activity and stereoselectivity were strongly affected by the types of aluminum alkyls and organic borates. The change of ligands resulted in different catalytic activities, while it didn't influence the stereoselectivity. When the chain lengths of monomers were longer than C6, the system will conducted highly isospecific polyolefins of more than99%.
(3) NCN-pincer2,6-bis(4'-isopropyl-2'-oxazolinyl)phenyl-ligated rare-earth-metal dichlorides were designed and synthesized, which have C2-symmetric geometry. Upon activation with organic borates and trialkylaluminium, the complexes exhibited highly catalytic activities and more than98%cas-1,4selectivity for isoprene polymerization (up to99.5%). When the monomer to initiator ratio was increased from500to4000, the molecular weights of the resultant polymers increased linearly from11.7x104to49.9x104. Meanwhile, the molecular weight distribution and cis-1,4-selectivity were almost constant. These indicate that the system is probably a single active site to induce controllable polymerization. The activity showed a strong dependence on the central metal type. The order of activities is in agreement with the size of the metal ionic radii. The activity and stereoselectivity was strongly affected by the types of aluminum alkyls, while the types of organic borates influenced the activity only. This system showed a tolerance of change in the polymerization temperature. When polymerization was performed at elevated temperatures, the catalytic activity increased strikingly. The reaction temperature had little effect on the regioselectivity, and high cis-1,4selectivity almost remained even at80℃(cis-1,4>96%). According to the NMR, IR and MS spectra, the alkyl bridged Ln-Al bimetallic cations were proven to be the actual active species.
(1)基于氮杂环卡宾配体合成和修饰简单、配位能力强的特点,设计合成了三类氮杂环卡宾配位的稀土金属烷基化物。经过2倍当量有机硼盐活化,大位阻氮杂环卡宾配位的三烷基钪配合物能够高活性引发α-烯烃聚合,表明强供电子能力的氮杂环卡宾配体能够很好地稳定催化活性物种。该体系也能够催化1-己烯与1,5-己二烯共聚,所得共聚物中1,5-己二烯环化程度很高,两种单体单元的比例可以通过改变加料比方便的调控。并且随着共聚物中1,5-己二烯单元含量的增加,共聚物的玻璃化转变温度成线性增加。此外,通过核磁共振跟踪表明,氮杂环卡宾配位的单烷基钪二价阳离子为催化活性物种。
(2)设计开发了一类基于三氯化钪的简单Ziegler-Natta催化体系,能够在室温下中等活性催化1-己烯聚合,得到高分子量(>100万)和完全等规结构的聚1-己烯(mmmm>99%)。该体系具有良好的热稳定性和立体选择性,在80℃高温条件下,也能够得到高等规度的聚1-己烯(mmmm=97.3％).这是迄今为止稀土金属催化体系在高温下得到的最高值。中心金属的种类对催化性能起决定性作用,当采用其他几种稀土金属氯化物时,相同条件下不能催化1-己烯聚合。烷基铝和有机硼盐的种类对催化体系的活性和立体选择性都有影响：催化剂中配位基团的种类对催化活性影响较大,但是对立体选择性影响不大。单体碳链的长度对所得聚合物立体选择性影响较大,当单体碳链长度大于等于6时,所得聚合物具有完全等规结构。
(3)设计合成了一系列NCN-钳形双嗯唑啉稀土金属氯化物,配合物分子具有C2对称结构。在烷基铝和有机硼盐共同作用下,该类配合物能够高活性催化异戊二烯聚合,所得聚合物具有较高的顺式-1,4结构(最高可达99.5%)。聚合物分子量随单体与催化剂比例的增加而成比例增大,说明了该催化体系的单活性中心的特征。该体系的催化活性随着中心金属离子半径的增大而增加。烷基铝试剂的种类对催化活性和聚合的选择性都有影响；有机硼盐的种类对催化活性亦有影响,而对聚合的选择性影响不大。此外,在80℃高温条件下,该催化体系表现了良好的热稳定性和定向聚合能力,能够催化得到顺式-1,4结构含量大于96%的聚异戊二烯。通过核磁共振波谱、红外光谱等分析手段表明,含有配体的烷基桥连稀土-铝双核离子对为催化活性物种。
Rare-earth-metal complexes were booming for their superior catalytic behavior in polymerizations of ethylene, styrene, or conjugated dienes in the past decade. However, only limited catalyst systems have been used for polymerization of-olefins. Most of them exhibited low formation rates for polymers with low molecular weight. Compared with cyclopentadienyl complexes, the non-cyclopentadienyl complexes, which could be easily prepared and modified in ligand structures, have been widely applied to olefm polymerization. In this thesis, three kinds of rare-earth-metal catalyst systems with non-cyclopentadienyl ligands were developed. Also, their catalytic behaviors were detailed for (co)polymerization of α-olefins or isoprene. The results are summarized as followings:
(1) N-heterocyclic carbenes (NHC) are an ideal ligand for coordinating to rare-earth metals, due to their strong σ-donating ability. Trialkyl rare-earth-metal complexes bearing three kinds of NHC ligands were designed and synthesized. Upon activation with two equivalents of [Ph3C][B(C6Fs)4], the scandium complexes with sterically hindered NHC ligands exhibited high activities for a-olefin polymerization, demonstrating that the NHC ligand is capable of stabilizing the presumed cationic active species. The catalyst systems with trialkyl scandium complexes also conducted copolymerization of1-hexene (H) with1,5-hexadiene (HD) to give random atactic H/HD copolymers with a wide range of HD contents(26.6-98.6mol%), a previously unreported copolymer. The cyclization selectivity of the copolymerization is very high. An increase of the HD content in copolymers results in an obvious change of Tg of the copolymers. The Tg value is proportional to the HD content in the copolymer. According to the in situ NMR monitoring, the active species was proposed to be the dicationic complex.
(2) A simple Ziegler-Natta catalyst system based on ScCl3was developed. The system could conduct highly isospecific polymerization of1-hexene (mmmm>99%), and the resultant polymers possess high molecular weight(～106). This system proved to be showed an excellent stereoselectivity(mmmm>97%) even at80℃, the highest record for this polymerization at elevated temperatures. The activity showed a strong dependence on the central metal type. Replacing ScCl3(THF)3with YC13(THF)3.5, LaCl3(THF)2or LuCl3(THF)3resulted in nearly complete loss in activity for1-hexene polymerization. The activity and stereoselectivity were strongly affected by the types of aluminum alkyls and organic borates. The change of ligands resulted in different catalytic activities, while it didn't influence the stereoselectivity. When the chain lengths of monomers were longer than C6, the system will conducted highly isospecific polyolefins of more than99%.
(3) NCN-pincer2,6-bis(4'-isopropyl-2'-oxazolinyl)phenyl-ligated rare-earth-metal dichlorides were designed and synthesized, which have C2-symmetric geometry. Upon activation with organic borates and trialkylaluminium, the complexes exhibited highly catalytic activities and more than98%cas-1,4selectivity for isoprene polymerization (up to99.5%). When the monomer to initiator ratio was increased from500to4000, the molecular weights of the resultant polymers increased linearly from11.7x104to49.9x104. Meanwhile, the molecular weight distribution and cis-1,4-selectivity were almost constant. These indicate that the system is probably a single active site to induce controllable polymerization. The activity showed a strong dependence on the central metal type. The order of activities is in agreement with the size of the metal ionic radii. The activity and stereoselectivity was strongly affected by the types of aluminum alkyls, while the types of organic borates influenced the activity only. This system showed a tolerance of change in the polymerization temperature. When polymerization was performed at elevated temperatures, the catalytic activity increased strikingly. The reaction temperature had little effect on the regioselectivity, and high cis-1,4selectivity almost remained even at80℃(cis-1,4>96%). According to the NMR, IR and MS spectra, the alkyl bridged Ln-Al bimetallic cations were proven to be the actual active species.
引文
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