环己烯环氧化催化剂的合成、表征及其催化性能研究
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摘要
本文是在河南省杰出人才创新基金项目(编号：0121001900)资金资助下完成的。
目前已知的烯烃环氧化用高活性催化剂大多是均相催化剂(如过渡金属V(Ⅴ)、Mo(Ⅵ)、W(Ⅵ)、Ti(Ⅳ)等的配合物)，虽反应条件温和、选择性好、转化率高，但难于从反应体系中分离回收和重复使用。因此选择合适的方法将活性组分负载到有机或无机载体上，是均相催化剂多相化研究的关键之一。许多研究表明，有机或无机高分子材料不仅是负载金属活性物种的一个惰性载体，而且还可以提供一种特定的环境(可充当配体，或提供酸碱性等)，通过三维空间的多点作用，可对金属活性中心进行修饰，使催化剂结构发生变化，从而影响催化剂性能达到高活性和选择性。还具有与反应物、产物易分离，可多次重复使用之优点。本文以二乙烯基苯交联的大孔聚苯乙烯树脂及价廉易得的无机高分子材料SiO_2为载体，键合引入前期已筛选出的活性、选择性都很优良的Mo(Ⅵ)活性物种，合成出了一系列高分子Mo配合物并用于催化环己烯环氧化反应研究，进而筛选出了具有工业应用价值的多相催化剂品种，消除了均相催化剂的诸多缺陷，达到了催化剂反应后分离方便且能循环使用之目的。
本文主要在以下几方面开展了研究工作并获得重要成果，具体如下：
(1)、选择过渡金属Mo(Ⅵ)为活性物种，以分子结构特别且具有优异活性和选择性的MoO_2(acac)_2为催化剂多相化研究样本，探讨了物料摩尔比，反应时间、温度、反应氛围、溶剂用量等因素对合成环氧环己烷反应的影响，用正交实验技术优化了环氧化合成条件，即：，以n(t-BuOOH)=0.1mol计，溶剂用量10ml，温度80℃，时间60min，MoO_2(acac)_2用量0.1g。以t-BuOOH计，环氧环己烷收率在99.5％以上。此外，还建立了易于操作的环氧环己烷气相色谱分析方法。
(2)、采用PS树脂为载体，设计并合成了以N为配位原子的乙二胺类系列高分子配体，首次合成了PS负载乙二胺类系列Mo(Ⅵ)配合物；设计并制备了以O为配位原子的乙酰丙酮(β—二酮)、乙二醇(α—二醇)类系列高分子配体，首次合成了PS负载乙酰丙酮系列Mo(Ⅵ)配合物和乙二醇系列配体Mo(Ⅵ)配合物；设计并制备了含有N、O为配位原子的乙醇胺、乙二胺缩水杨醛Schiff碱高分子配体，首次合成了PS负载乙醇胺及乙二胺缩水杨醛Schiff碱Mo(Ⅵ)配合物。用红外光谱(IR)、原子吸收光谱(AAS)、X-光电子能谱(XPS)等技术对合成催化剂进行了表征，检验了PS负载Mo(Ⅵ)活性组分的有效性，测定了负载金属Mo活性组分的量及其化合价态。工作中，还建立了PS负载Mo配合物中Mo的化学分析新方法。
环己烯环氧化催化剂的合成、表征及其催化性能研究
将上述PS负载Mo(vi)配合物用于催化t一Bu0OH环氧化环己烯反应，结果发现，
仅含有N配位原子的M。配合物虽具有很高催化活性，但N配位原子的强碱性，降低
了Mo活性中心的L酸性，反应时催化选择性严重下降。催化活性和选择性皆较高的
是含O配位原子的乙酞丙酮(p一二酮)、乙二醇(。一二醇)系列以及含N、O配位原
子的乙醇胺、乙二胺缩水杨醛等类Mo(vi)配合物，尤其是PS负载乙酞丙酮Mo少D、
乙二胺缩水杨醛Mo(VI)配合物的催化活性和选择性更为优秀。5次循环使用后，仍可
保持最初的优良催化性能。虽催化剂外观上有些微碎裂，但并不影响其催化效果。
(3)首次以Mo的3d52电子结合能值为判据，提出了Mo(Vl)催化环氧化规律，即:
对于结构相似的PS负载Mo(VI)配合物，若其M。的3d，2电子结合能值小(大)，其催
化环氧化活性和选择性就相对较低(高);当M。(VI)配合物的Mo3山2电子结合能值相
同(近)时，空间效应大的Mo(V工)催化选择性低，因此在Mo(VI)中心与载体表面间保持
适当的距离对选择性有利。
由于PS载体表面具有化学惰性，孔道为大孔，反应具有类液体特性，与结构相似
的小分子MO配合物具有相同的反应信息，因此本规律可外延至小分子M。配合物，对
寻找和设计新的Mo配合物环氧化催化剂，具有指导性和可操作性。
(4)、为减小催化剂成本，以无机高分子材料一510:代替PS树脂为载体，采用化
学键合方法，将 Mo活性组分在510:载体中进行新的设计与组装，并检测其催化性能。
结果发现，与PS载体负载乙酞丙酮、乙醇胺以及乙二醇类M。配合物相比，制备的
5102键合相同小分子配体M。配合物具有更优良的催化性能。优异催化剂品种为5102
键合乙酞丙酮MO配合物，循环使用5次后基本保持原始高活性和高选择性。此外，
还发现510:载体表面结构氧与M。活性中心存在强相互作用，使M。的3d5:结合能
值升高，有利于环氧化反应。
(5)、首次以(MoOCll)2/510:为前体，设计并合成出了MoO‘:2一/510:催化剂。该催化
剂具有优异的催化性能且循环使用5次后基本保持最初的高活性和选择性。
鉴于以上以PS负载或510:键合的乙酞丙酮\1o配合物、Mo叭2一/5102催化剂具有优
异催化环氧化活性和选择性，5次循环使用后，基本保持最初的催化活性和选择性，
特推荐为t一BuOOH环氧化环己烯合成环氧环己烷工业用催化剂品种样本。
This dissertation was financially supported by Henan Province Elitist Innovation Fund.
The epoxidation of alkene is a kind of complicated reactions because the oxidation can take palce either at the C=C double bond or at the a - H atom which result in low selectivity of the epoxidation. At present, most of the well-known catalysts with high activity for the epoxidation are homogeneous, such as high valence transition metal complexes of Ti(IV), V(V), Cr(VI), Mo(VI) and W(VI), which possess the merits of moderate reaction condition, high activity, selectivity and so on, but are difficult to be separated from the reaction system and to be reused. Thus, the methods and techniques to surpport high valence transition metal complexes on organic or inorganic materials is one of the key steps to make the homogeneous catalysts heterogeneous.
Divinylbenzene cross-linked macropore polystyrene resin( simply named with PS) is a kind of organic macromolecule materials which do not dissolve in water, acid, alkali or organic solvent, and own the merits of strong anti-oxidizability, good stability, easiness of being functionalized and due to the presence of macropores, their reactive properties are same to those of liquids. In this work, we designed and prepared several series of of macromolecule ligands and macromolecule metal complexes catalysts based on the structural characters of PS resin. Moreover, inexpensive and available inorganic macromolecule materials SiC>2, are also used as carriers to be anchored with Mo active species, which have the promising properties of anti-oxidizability, thermal stability, mechanical intensity, porousness, high specific surface area and which can also form strong chemical bond or absorption with the active sites through the H groups in the surface. All the above supported catalysts are used in the catalytic epoxid
ation of cyclohexene.
In the dissertation, we mainly carried out the following several aspects of research works and have made significant achievements:
(1) We have synthesized three kinds of micromolecule homogeneous catalysts, i.e. VO(acac)2, MoO2(acac)2 and MoO2(oxine)2, which are characterized by elemental analysis, IR etc. The results of epoxidation of cyclohexene with f-BuOOH catalyzed by such catalysts as VO(acac)2, MoO2(acac)2, Mo02(oxine)2, MoO3, WO3, Na2MoO4 and Na2W04, are compared to those of the previous researches with the transition metal complexes catalysts and finally we selected Mo(VI) O2(acac)2 as the active species. Effects of different factors, such as the mole ratio between different matariels, reaction time, tempreture,
WLPage]=006
reactive circumstance and amount of solvent on the yield of cyclohexene oxide, were discussed in this epoxidation and the optimal synthesis conditions were obtained by orthogonal technique, which are detailed as follow: ( based on 0.1 mol of f-BuOOH), 10 mL of solvent, temperature 353 K, raction time 60 min and 0.1 g of MoO2(acac)2. Under the above conditions, the yield of cyclohexene oxide were all over 99.5% and which are also used as the main reaction conditions to test the catalytic properties of different macromolecule Mo(VI) complexes prepared. In this research, we also found the easily operable GC analysis method of cyclohexene oxide.
(2) In this section, we designed and prepared three series of macromolecule ligands, i.e. ethylenediamine Hands in which the coordinate atom is N, acetylacetone( 3 -dione) and glycol( a -diol) ligands in which the coordinate atom is O and other macromolecule ligands with the coordinate atoms of both N and O, such as ethanolamine and the condensate of ethylenediamine and salicylaldehyde Schiff Base. And for the first time, we have synthesized PS-grafted different Mo(VI) complexes with the above ligands which are characterized by using IR, AAS, XPS etc to confirm that Mo active species have been grafted on the PS resin. We also determined the amount and the valence of the grafted Mo(VI) active species and built the chemical analysis method of amount of Mo in the PS-grafted Mo co
目前已知的烯烃环氧化用高活性催化剂大多是均相催化剂(如过渡金属V(Ⅴ)、Mo(Ⅵ)、W(Ⅵ)、Ti(Ⅳ)等的配合物)，虽反应条件温和、选择性好、转化率高，但难于从反应体系中分离回收和重复使用。因此选择合适的方法将活性组分负载到有机或无机载体上，是均相催化剂多相化研究的关键之一。许多研究表明，有机或无机高分子材料不仅是负载金属活性物种的一个惰性载体，而且还可以提供一种特定的环境(可充当配体，或提供酸碱性等)，通过三维空间的多点作用，可对金属活性中心进行修饰，使催化剂结构发生变化，从而影响催化剂性能达到高活性和选择性。还具有与反应物、产物易分离，可多次重复使用之优点。本文以二乙烯基苯交联的大孔聚苯乙烯树脂及价廉易得的无机高分子材料SiO_2为载体，键合引入前期已筛选出的活性、选择性都很优良的Mo(Ⅵ)活性物种，合成出了一系列高分子Mo配合物并用于催化环己烯环氧化反应研究，进而筛选出了具有工业应用价值的多相催化剂品种，消除了均相催化剂的诸多缺陷，达到了催化剂反应后分离方便且能循环使用之目的。
本文主要在以下几方面开展了研究工作并获得重要成果，具体如下：
(1)、选择过渡金属Mo(Ⅵ)为活性物种，以分子结构特别且具有优异活性和选择性的MoO_2(acac)_2为催化剂多相化研究样本，探讨了物料摩尔比，反应时间、温度、反应氛围、溶剂用量等因素对合成环氧环己烷反应的影响，用正交实验技术优化了环氧化合成条件，即：，以n(t-BuOOH)=0.1mol计，溶剂用量10ml，温度80℃，时间60min，MoO_2(acac)_2用量0.1g。以t-BuOOH计，环氧环己烷收率在99.5％以上。此外，还建立了易于操作的环氧环己烷气相色谱分析方法。
(2)、采用PS树脂为载体，设计并合成了以N为配位原子的乙二胺类系列高分子配体，首次合成了PS负载乙二胺类系列Mo(Ⅵ)配合物；设计并制备了以O为配位原子的乙酰丙酮(β—二酮)、乙二醇(α—二醇)类系列高分子配体，首次合成了PS负载乙酰丙酮系列Mo(Ⅵ)配合物和乙二醇系列配体Mo(Ⅵ)配合物；设计并制备了含有N、O为配位原子的乙醇胺、乙二胺缩水杨醛Schiff碱高分子配体，首次合成了PS负载乙醇胺及乙二胺缩水杨醛Schiff碱Mo(Ⅵ)配合物。用红外光谱(IR)、原子吸收光谱(AAS)、X-光电子能谱(XPS)等技术对合成催化剂进行了表征，检验了PS负载Mo(Ⅵ)活性组分的有效性，测定了负载金属Mo活性组分的量及其化合价态。工作中，还建立了PS负载Mo配合物中Mo的化学分析新方法。
环己烯环氧化催化剂的合成、表征及其催化性能研究
将上述PS负载Mo(vi)配合物用于催化t一Bu0OH环氧化环己烯反应，结果发现，
仅含有N配位原子的M。配合物虽具有很高催化活性，但N配位原子的强碱性，降低
了Mo活性中心的L酸性，反应时催化选择性严重下降。催化活性和选择性皆较高的
是含O配位原子的乙酞丙酮(p一二酮)、乙二醇(。一二醇)系列以及含N、O配位原
子的乙醇胺、乙二胺缩水杨醛等类Mo(vi)配合物，尤其是PS负载乙酞丙酮Mo少D、
乙二胺缩水杨醛Mo(VI)配合物的催化活性和选择性更为优秀。5次循环使用后，仍可
保持最初的优良催化性能。虽催化剂外观上有些微碎裂，但并不影响其催化效果。
(3)首次以Mo的3d52电子结合能值为判据，提出了Mo(Vl)催化环氧化规律，即:
对于结构相似的PS负载Mo(VI)配合物，若其M。的3d，2电子结合能值小(大)，其催
化环氧化活性和选择性就相对较低(高);当M。(VI)配合物的Mo3山2电子结合能值相
同(近)时，空间效应大的Mo(V工)催化选择性低，因此在Mo(VI)中心与载体表面间保持
适当的距离对选择性有利。
由于PS载体表面具有化学惰性，孔道为大孔，反应具有类液体特性，与结构相似
的小分子MO配合物具有相同的反应信息，因此本规律可外延至小分子M。配合物，对
寻找和设计新的Mo配合物环氧化催化剂，具有指导性和可操作性。
(4)、为减小催化剂成本，以无机高分子材料一510:代替PS树脂为载体，采用化
学键合方法，将 Mo活性组分在510:载体中进行新的设计与组装，并检测其催化性能。
结果发现，与PS载体负载乙酞丙酮、乙醇胺以及乙二醇类M。配合物相比，制备的
5102键合相同小分子配体M。配合物具有更优良的催化性能。优异催化剂品种为5102
键合乙酞丙酮MO配合物，循环使用5次后基本保持原始高活性和高选择性。此外，
还发现510:载体表面结构氧与M。活性中心存在强相互作用，使M。的3d5:结合能
值升高，有利于环氧化反应。
(5)、首次以(MoOCll)2/510:为前体，设计并合成出了MoO‘:2一/510:催化剂。该催化
剂具有优异的催化性能且循环使用5次后基本保持最初的高活性和选择性。
鉴于以上以PS负载或510:键合的乙酞丙酮\1o配合物、Mo叭2一/5102催化剂具有优
异催化环氧化活性和选择性，5次循环使用后，基本保持最初的催化活性和选择性，
特推荐为t一BuOOH环氧化环己烯合成环氧环己烷工业用催化剂品种样本。
This dissertation was financially supported by Henan Province Elitist Innovation Fund.
The epoxidation of alkene is a kind of complicated reactions because the oxidation can take palce either at the C=C double bond or at the a - H atom which result in low selectivity of the epoxidation. At present, most of the well-known catalysts with high activity for the epoxidation are homogeneous, such as high valence transition metal complexes of Ti(IV), V(V), Cr(VI), Mo(VI) and W(VI), which possess the merits of moderate reaction condition, high activity, selectivity and so on, but are difficult to be separated from the reaction system and to be reused. Thus, the methods and techniques to surpport high valence transition metal complexes on organic or inorganic materials is one of the key steps to make the homogeneous catalysts heterogeneous.
Divinylbenzene cross-linked macropore polystyrene resin( simply named with PS) is a kind of organic macromolecule materials which do not dissolve in water, acid, alkali or organic solvent, and own the merits of strong anti-oxidizability, good stability, easiness of being functionalized and due to the presence of macropores, their reactive properties are same to those of liquids. In this work, we designed and prepared several series of of macromolecule ligands and macromolecule metal complexes catalysts based on the structural characters of PS resin. Moreover, inexpensive and available inorganic macromolecule materials SiC>2, are also used as carriers to be anchored with Mo active species, which have the promising properties of anti-oxidizability, thermal stability, mechanical intensity, porousness, high specific surface area and which can also form strong chemical bond or absorption with the active sites through the H groups in the surface. All the above supported catalysts are used in the catalytic epoxid
ation of cyclohexene.
In the dissertation, we mainly carried out the following several aspects of research works and have made significant achievements:
(1) We have synthesized three kinds of micromolecule homogeneous catalysts, i.e. VO(acac)2, MoO2(acac)2 and MoO2(oxine)2, which are characterized by elemental analysis, IR etc. The results of epoxidation of cyclohexene with f-BuOOH catalyzed by such catalysts as VO(acac)2, MoO2(acac)2, Mo02(oxine)2, MoO3, WO3, Na2MoO4 and Na2W04, are compared to those of the previous researches with the transition metal complexes catalysts and finally we selected Mo(VI) O2(acac)2 as the active species. Effects of different factors, such as the mole ratio between different matariels, reaction time, tempreture,
WLPage]=006
reactive circumstance and amount of solvent on the yield of cyclohexene oxide, were discussed in this epoxidation and the optimal synthesis conditions were obtained by orthogonal technique, which are detailed as follow: ( based on 0.1 mol of f-BuOOH), 10 mL of solvent, temperature 353 K, raction time 60 min and 0.1 g of MoO2(acac)2. Under the above conditions, the yield of cyclohexene oxide were all over 99.5% and which are also used as the main reaction conditions to test the catalytic properties of different macromolecule Mo(VI) complexes prepared. In this research, we also found the easily operable GC analysis method of cyclohexene oxide.
(2) In this section, we designed and prepared three series of macromolecule ligands, i.e. ethylenediamine Hands in which the coordinate atom is N, acetylacetone( 3 -dione) and glycol( a -diol) ligands in which the coordinate atom is O and other macromolecule ligands with the coordinate atoms of both N and O, such as ethanolamine and the condensate of ethylenediamine and salicylaldehyde Schiff Base. And for the first time, we have synthesized PS-grafted different Mo(VI) complexes with the above ligands which are characterized by using IR, AAS, XPS etc to confirm that Mo active species have been grafted on the PS resin. We also determined the amount and the valence of the grafted Mo(VI) active species and built the chemical analysis method of amount of Mo in the PS-grafted Mo co
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