金属配合物配体上离子取代基对其催化活性影响的研究
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摘要
用传统有机取代基修饰金属配合物配体一直是大家广泛应用的增强催化剂活性的方法。但由于在金属配合物配体上变换不同传统有机取代基的困难性以及传统有机取代基的修饰较难改变金属配合物催化剂的可回收套用能力,因而学术界和工业界一直在努力寻求一种有效的方法来解决上述两个问题。用离子取代基修饰金属配合物催化剂配体是最近这一领域研究的热点。通过调节不同的阴阳离子组合可以使催化剂从低极性溶剂转移到高极性溶剂,因而这种配体被离子取代基修饰过的金属配合物可以方便的分离与循环套用。最近,这种通常被用来使均相催化剂在水中可溶解或者可回收的离子取代基又被用来改善催化剂催化活性。虽然人们已经清楚配体上的离子取代基可以改变催化剂的溶解能力,但是离子取代基对于金属配合物催化剂催化能力的影响并不清楚。因而对金属配合物配体上的离子取代基对其催化活性的研究将会非常有意义。
本论文主要设计和合成了三类新型的乙酰丙酮类金属配合物催化剂。它们最大的特点是离子型取代基与配体是以共轭双键连接,因此阴阳离子相互作用可以传递到金属中心。本文将此类型的催化剂应用于催化分子氧氧化4.甲基愈创木酚的反应中,并对氧化条件,反应机理,产物分离以及反应体系的循环套用等方面进行了研究。同时本文还研究了影响配体上含离子取代基的金属配合物催化剂催化活性的因素。
本文首先设计和合成了两类配体上含阳离子型离子取代基的乙酰丙酮类金属配合物Co-[Salen-X][Y]2(X=Py, Mim; Y=PF6-，ClO4-, BF4-,NO3-, Br-, BPh4-)和[Co(acac-Mim)2][Y]2(Y=Cl-, NO3-,BF4-, PF6-, ClO4-和一类配体上含阴离子型离子取代基的乙酰丙酮类金属配合物[X][Co(F6-acac)3](X=NH4+, C2Py+, N4,4,4,4+, C4Mim+, P4,4,4,10+)。通过常规的分析手段如红外光谱,质谱,核磁共振波谱,原子吸收光谱确定了这些金属配合物的分子结构。同时本文还培养出配体[Salen-Py][Br2]2,金属配合物Cu-[Salen-Mim][Br]2、Cu-[Salen-Py][NO3]2、 Cu-[Salen-Py][BPh4]2的单晶,通过X射线分析进一步证实了上述化合物的分子结构。
接下来本文用一种配体上含吡啶盐阳离子型离子取代基的钴席夫碱催化剂Co-[Salen-Py][PF6]2催化分子氧氧化4.甲基愈创木酚的反应,发现离子取代基和传统的吸电子有机取代基一样是通过降低金属配合物的活性中心金属的电子密度来增强催化剂的催化活性的。相对于配体上无离子取代基的乙酰丙酮金属配合物Co(acacen),配体上含离子取代基的金属配合物Co-[Salen-Py][PF6]2具有更高的催化活性。通过对氧化反应条件优化,本文中的工艺路线可以使氧化底物4-甲基愈创木酚的转化率达到99.9%,产物香兰素的选择性达到90%。与此同时,使用乙二醇和水的混合溶剂产物香兰素可以以钠盐的形式通过简单的结晶进行分离。含有大量NaOH的结晶母液(NaOH/4-甲基愈创木酚=2.38/1)可以至少成功套用3次,因而当结晶母液套用时反应中所加的NaOH/底物的摩尔比从3.3：1降低到1.05：1。这种工艺方法为工业上提供了一种潜在的更为绿色的途径去制备香兰素。对反应机理的研究,发现本文中的氧化反应机理为自由基链反应机理。
最后,本文研究了配体上的离子取代基的反离子对金属配合物催化剂催化活性的影响。对配体上含阳离子型离子取代基和阴离子型离子取代基的反离子进行了研究,发现改变与配体相连离子取代基的反离子对催化剂的催化活性改变不是很大。为了更进一步研究离子取代基的反离子对催化剂金属中心的电子影响,通过量化计算利用密度泛函的方法对上述催化剂的简化模型(离子取代基单取代的苯)的C-3NBO电荷密度进行了理论研究。研究结果发现与配体相连的离子取代基不论是阳离子型还是阴离子型都是吸电子型取代基,都不同程度的降低了金属配合物的中心金属的电子密度。但变化不同反离子对金属中心电子密度的影响并不是很大。不同中心金属和不同溶剂对该类催化剂催化活性影响的实验结果的得出,发现改变催化剂的中心金属比改变离子取代基的反离子可以更加有效的增强催化剂活性。
总的来说,本论文以配体上含离子取代基的乙酰丙酮类金属配合物催化分子氧氧化4-甲基愈创木酚为研究对象,开发和合成了三类新型的配体上含离子取代基的乙酰丙酮类金属配合物催化剂。至少在乙酰丙酮类金属配合物中阳离子型取代基和阴离子型取代基都是吸电子型取代基,离子取代基的反离子可以适度的调节催化剂的催化活性。这些研究结果可以为今后更好地利用离子取代基来设计高效的催化剂奠定基础。同时利用该类含离子取代基的乙酰丙酮催化剂催化氧化4-甲基愈创木酚制备香兰素的研究为香兰素的对甲酚工艺的产业化也提供了一定的技术支持。
Conventional organic substituents on the ligand of metal complex catalysts have long been widely used to tune their activities and selectivities. Due to the difficult to synthesis different conventional organic substituents on the ligand of metal complex and this type of catalysts are also not easily recovered, it needs an efficient method to solve the problems mentioned above for both academia and industry. Modifying the ligand of metal complex by ionic compound is a recent development in this field. These metal complex catalysts with ionic substituents on the ligand are easily retrieved and recycled because their solubility can be adjusted by using different cation-anion combinations, enabling phase separation from less polar organic solvents to aqueous media. Recently, ionic substituents, which usually enable the homogeneous catalyst dissolved in water and recovered, are also involved to improve the activity of catalyst. Though it has been well known that ionic substituents on the ligand can change catalyst solubility, it is still unclear how exactly it influences their catalytic ability. Hence, the research of the effect of ionic substituent on the ligand on the catalytic activity is necessary.
We designed and synthesized three types of acetylacetone metal complexes catalysts. The most appealing features of the catalysts were that the ionic substituent connected with the metal center by conjugated double bond, thus the cation-anion interaction could easily deliver to the metal center. The catalysts were used in the allylic oxidation of4-methyl guaiacol, and the oxidation reaction conditions, reaction mechanism, Vanillin isolation and reaction medium recycling were researched. We also studied the influences on the catalytic activity of catalysts with ionic substituents on the ligand.
In this dissertation, two types of acetylacetone metal complexes catalysts with cationic ionic substituents on the ligand Co-[Salen-X][Y]2(X=Py, Mim; Y=PF6-, ClO4-, BF4-, NO3-, Br-, BPh4-) and [Co(acac-Mim)2][Y]2(Y=Cl-, NO3-, BF4-,PF6-, C1O4-) and one types of acetylacetone metal complexes catalysts with anionic ionic substituents on the ligand [X][Co(F6-acac)3](X=NH4+, C2Py+, N44,4,4,4+, C4Mim+, P4,4,4,10+) were designed and synthesized. These metal complexes were charactered by IR, MS and element analysis to check the molecular structure. At the same time, to further prove the identity of these complexes, we have succeeded obtain the single crystal for Cu-[Salen-Mim][Br]2, Cu-[Salen-Py][NO3]2,[Salen-Py][Br2]2, Cu-[Salen-Py][BPh4]2for X-ray analysis.
Later on, a cobalt Schiff base catalyst with ionic substituents on the ligand Co-[Salen-Py][PF6]2was used for the oxidation of4-methyl guaiacol to vanillin. The results showed that the catalytic activities of this modified catalysts were significantly improved compared with their unmodified counterpart. Tentative reaction mechanism research indicated that the electron-withdrawing pyridinium substituent on the ligand of Co(acacen) is responsible for the high selectivity of vanillin. Meanwhile, utilizing ethylene glycol and water as solvent, vanillin can be isolated by simple crystallization in the form of a sodium salt, and the mother liquid of the crystallization, with a large amount of NaOH (the mole ratio of NaOH/4-methyl guaiacol=2.38/1), can be successfully recycled at least three times, thereby decreasing the mole ratio of base/substrate from3.3:1to1.05:1when the mother liquid of crystallization was recycled. This strategy provides a potentially greener alternative for the synthesis of vanillin in industry.
At last, the influences on the catalyst reactivity of the catalysts with ionic substituents on the ligand by changing the counter ions of the ionic substituents were explored. No matter what kinds of counter ions were changed--cationic or anionic, we still found that the counter ions were only moderate improved the activity. To further investigate the electronic effect of different counter ions of ionic substituents on the central metal of the catalyst, the NBO charge of C-3in the simply model of the real catalysts (ionic substituent-monosubtituted benzenes) was investigated by means of quantum chemical calculations utilizing Density Functional Theory (DFT). The result shown that the cationic ionic substituents and the anionic ionic substituents are electron-withdrawing substituents, the counter ions of ionic substituents also have moderate effect on electron density on the central metal. The inflence of different central metals and solvents on the catalytic activity of the acetylacetone metal complexes catalysts with imidazolium ionic substituents on the ligand were investigated. The result indicated that changed the central metal was a more effective method than change the counter ions of the ionic substituents to improve the catalytic activity.
In short, the oxidation of4-methyl guaiacol to vanillin by the metal complexes with ionic substituents on the ligand was studied, and three types of acetylacetone metal complexes catalysts with ionic substituents on the ligand were involved. The cationic ionic substituents and the anionic ionic substituents are electron-withdrawing substituents, and the counter ions of the ionic substituents were only moderate improved the activity may enlighten us to use the ionic substituents to design novel and efficient catalysts. At the same time, the oxidation4-methyl guaiacol to vanillin by the acetylacetone metal complexes with ionic substituents on the ligand is a potentially greener alternative for the synthesis of the vanillin in industry.
本论文主要设计和合成了三类新型的乙酰丙酮类金属配合物催化剂。它们最大的特点是离子型取代基与配体是以共轭双键连接,因此阴阳离子相互作用可以传递到金属中心。本文将此类型的催化剂应用于催化分子氧氧化4.甲基愈创木酚的反应中,并对氧化条件,反应机理,产物分离以及反应体系的循环套用等方面进行了研究。同时本文还研究了影响配体上含离子取代基的金属配合物催化剂催化活性的因素。
本文首先设计和合成了两类配体上含阳离子型离子取代基的乙酰丙酮类金属配合物Co-[Salen-X][Y]2(X=Py, Mim; Y=PF6-，ClO4-, BF4-,NO3-, Br-, BPh4-)和[Co(acac-Mim)2][Y]2(Y=Cl-, NO3-,BF4-, PF6-, ClO4-和一类配体上含阴离子型离子取代基的乙酰丙酮类金属配合物[X][Co(F6-acac)3](X=NH4+, C2Py+, N4,4,4,4+, C4Mim+, P4,4,4,10+)。通过常规的分析手段如红外光谱,质谱,核磁共振波谱,原子吸收光谱确定了这些金属配合物的分子结构。同时本文还培养出配体[Salen-Py][Br2]2,金属配合物Cu-[Salen-Mim][Br]2、Cu-[Salen-Py][NO3]2、 Cu-[Salen-Py][BPh4]2的单晶,通过X射线分析进一步证实了上述化合物的分子结构。
接下来本文用一种配体上含吡啶盐阳离子型离子取代基的钴席夫碱催化剂Co-[Salen-Py][PF6]2催化分子氧氧化4.甲基愈创木酚的反应,发现离子取代基和传统的吸电子有机取代基一样是通过降低金属配合物的活性中心金属的电子密度来增强催化剂的催化活性的。相对于配体上无离子取代基的乙酰丙酮金属配合物Co(acacen),配体上含离子取代基的金属配合物Co-[Salen-Py][PF6]2具有更高的催化活性。通过对氧化反应条件优化,本文中的工艺路线可以使氧化底物4-甲基愈创木酚的转化率达到99.9%,产物香兰素的选择性达到90%。与此同时,使用乙二醇和水的混合溶剂产物香兰素可以以钠盐的形式通过简单的结晶进行分离。含有大量NaOH的结晶母液(NaOH/4-甲基愈创木酚=2.38/1)可以至少成功套用3次,因而当结晶母液套用时反应中所加的NaOH/底物的摩尔比从3.3：1降低到1.05：1。这种工艺方法为工业上提供了一种潜在的更为绿色的途径去制备香兰素。对反应机理的研究,发现本文中的氧化反应机理为自由基链反应机理。
最后,本文研究了配体上的离子取代基的反离子对金属配合物催化剂催化活性的影响。对配体上含阳离子型离子取代基和阴离子型离子取代基的反离子进行了研究,发现改变与配体相连离子取代基的反离子对催化剂的催化活性改变不是很大。为了更进一步研究离子取代基的反离子对催化剂金属中心的电子影响,通过量化计算利用密度泛函的方法对上述催化剂的简化模型(离子取代基单取代的苯)的C-3NBO电荷密度进行了理论研究。研究结果发现与配体相连的离子取代基不论是阳离子型还是阴离子型都是吸电子型取代基,都不同程度的降低了金属配合物的中心金属的电子密度。但变化不同反离子对金属中心电子密度的影响并不是很大。不同中心金属和不同溶剂对该类催化剂催化活性影响的实验结果的得出,发现改变催化剂的中心金属比改变离子取代基的反离子可以更加有效的增强催化剂活性。
总的来说,本论文以配体上含离子取代基的乙酰丙酮类金属配合物催化分子氧氧化4-甲基愈创木酚为研究对象,开发和合成了三类新型的配体上含离子取代基的乙酰丙酮类金属配合物催化剂。至少在乙酰丙酮类金属配合物中阳离子型取代基和阴离子型取代基都是吸电子型取代基,离子取代基的反离子可以适度的调节催化剂的催化活性。这些研究结果可以为今后更好地利用离子取代基来设计高效的催化剂奠定基础。同时利用该类含离子取代基的乙酰丙酮催化剂催化氧化4-甲基愈创木酚制备香兰素的研究为香兰素的对甲酚工艺的产业化也提供了一定的技术支持。
Conventional organic substituents on the ligand of metal complex catalysts have long been widely used to tune their activities and selectivities. Due to the difficult to synthesis different conventional organic substituents on the ligand of metal complex and this type of catalysts are also not easily recovered, it needs an efficient method to solve the problems mentioned above for both academia and industry. Modifying the ligand of metal complex by ionic compound is a recent development in this field. These metal complex catalysts with ionic substituents on the ligand are easily retrieved and recycled because their solubility can be adjusted by using different cation-anion combinations, enabling phase separation from less polar organic solvents to aqueous media. Recently, ionic substituents, which usually enable the homogeneous catalyst dissolved in water and recovered, are also involved to improve the activity of catalyst. Though it has been well known that ionic substituents on the ligand can change catalyst solubility, it is still unclear how exactly it influences their catalytic ability. Hence, the research of the effect of ionic substituent on the ligand on the catalytic activity is necessary.
We designed and synthesized three types of acetylacetone metal complexes catalysts. The most appealing features of the catalysts were that the ionic substituent connected with the metal center by conjugated double bond, thus the cation-anion interaction could easily deliver to the metal center. The catalysts were used in the allylic oxidation of4-methyl guaiacol, and the oxidation reaction conditions, reaction mechanism, Vanillin isolation and reaction medium recycling were researched. We also studied the influences on the catalytic activity of catalysts with ionic substituents on the ligand.
In this dissertation, two types of acetylacetone metal complexes catalysts with cationic ionic substituents on the ligand Co-[Salen-X][Y]2(X=Py, Mim; Y=PF6-, ClO4-, BF4-, NO3-, Br-, BPh4-) and [Co(acac-Mim)2][Y]2(Y=Cl-, NO3-, BF4-,PF6-, C1O4-) and one types of acetylacetone metal complexes catalysts with anionic ionic substituents on the ligand [X][Co(F6-acac)3](X=NH4+, C2Py+, N44,4,4,4+, C4Mim+, P4,4,4,10+) were designed and synthesized. These metal complexes were charactered by IR, MS and element analysis to check the molecular structure. At the same time, to further prove the identity of these complexes, we have succeeded obtain the single crystal for Cu-[Salen-Mim][Br]2, Cu-[Salen-Py][NO3]2,[Salen-Py][Br2]2, Cu-[Salen-Py][BPh4]2for X-ray analysis.
Later on, a cobalt Schiff base catalyst with ionic substituents on the ligand Co-[Salen-Py][PF6]2was used for the oxidation of4-methyl guaiacol to vanillin. The results showed that the catalytic activities of this modified catalysts were significantly improved compared with their unmodified counterpart. Tentative reaction mechanism research indicated that the electron-withdrawing pyridinium substituent on the ligand of Co(acacen) is responsible for the high selectivity of vanillin. Meanwhile, utilizing ethylene glycol and water as solvent, vanillin can be isolated by simple crystallization in the form of a sodium salt, and the mother liquid of the crystallization, with a large amount of NaOH (the mole ratio of NaOH/4-methyl guaiacol=2.38/1), can be successfully recycled at least three times, thereby decreasing the mole ratio of base/substrate from3.3:1to1.05:1when the mother liquid of crystallization was recycled. This strategy provides a potentially greener alternative for the synthesis of vanillin in industry.
At last, the influences on the catalyst reactivity of the catalysts with ionic substituents on the ligand by changing the counter ions of the ionic substituents were explored. No matter what kinds of counter ions were changed--cationic or anionic, we still found that the counter ions were only moderate improved the activity. To further investigate the electronic effect of different counter ions of ionic substituents on the central metal of the catalyst, the NBO charge of C-3in the simply model of the real catalysts (ionic substituent-monosubtituted benzenes) was investigated by means of quantum chemical calculations utilizing Density Functional Theory (DFT). The result shown that the cationic ionic substituents and the anionic ionic substituents are electron-withdrawing substituents, the counter ions of ionic substituents also have moderate effect on electron density on the central metal. The inflence of different central metals and solvents on the catalytic activity of the acetylacetone metal complexes catalysts with imidazolium ionic substituents on the ligand were investigated. The result indicated that changed the central metal was a more effective method than change the counter ions of the ionic substituents to improve the catalytic activity.
In short, the oxidation of4-methyl guaiacol to vanillin by the metal complexes with ionic substituents on the ligand was studied, and three types of acetylacetone metal complexes catalysts with ionic substituents on the ligand were involved. The cationic ionic substituents and the anionic ionic substituents are electron-withdrawing substituents, and the counter ions of the ionic substituents were only moderate improved the activity may enlighten us to use the ionic substituents to design novel and efficient catalysts. At the same time, the oxidation4-methyl guaiacol to vanillin by the acetylacetone metal complexes with ionic substituents on the ligand is a potentially greener alternative for the synthesis of the vanillin in industry.
引文
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