固体酸碱催化剂的制备及在酯交换和烷基化反应中的应用
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摘要
随着人类对环境保护意识的加强以及环境友好化学的不断发展，绿色化学工艺的研发逐渐成为热点课题。酸碱催化是石油化工及精细化工等领域中涉及最为广泛的一类工艺过程。传统的液体酸碱催化工艺存在着许多缺陷，例如：腐蚀设备、污染环境、分离和循环使用困难等。为了克服上述问题，人们已开展了大量的固体酸碱催化剂的研究工作，并已取得了显著进展。目前，针对一些具有重要应用背景的催化反应工艺过程研究和开发性能优异的固体酸碱催化剂仍是广泛关注的问题。
本文主要围绕酯交换法合成有机碳酸酯和甲苯-甲醇侧链烷基化反应开展了固体酸碱催化剂的制备、表征及催化性能研究工作。系统考察了不同方法制备的炭载氧化镁、介孔磷酸铝及Cs离子交换IM-5分子筛等催化剂体系对上述反应的催化性能；研究了催化剂组成、结构（孔径大小）和表面酸碱性质对催化剂反应性能的影响规律，并与催化剂的反应性能进行了关联；探讨了催化剂活性位性质和催化作用机制等问题。论文的主要研究内容和结果概述如下：
（一）炭载氧化镁催化剂在醇酯酯交换反应中的应用：
分别以三种炭材料（介孔炭NC-2、活性炭AC以及介孔炭CMK-3）为载体，采用浸渍法制备了负载型的MgO催化剂。考察了它们在碳酸二甲酯与乙醇酯交换以及碳酸二乙酯与各种醇类化合物酯交换反应中的催化性能。结果表明，几种炭载氧化镁都对该反应表现出了一定的催化活性，其中，MgO/NC-2材料的催化性能明显优于其它两种炭载氧化镁催化剂；在多相化测试反应中没有发现活性组分的流失现象；反应后的催化剂经过简单的焙烧处理后即可实现多次循环使用，且反应活性基本保持不变，表现出了良好的稳定性和循环性。结合催化剂的表征结果证实NC-2表面存在大量的含氧官能团，这些官能团的存在应该对MgO物种在炭载体表面实现高度分散起到了关键作用。此外，与单纯的MgO相比，负载的MgO/NC-2催化剂的碱性相对较弱，这表明MgO物种与载体NC-2之间存在一定的相互作用，这种相互作用的存在应该有助于提高催化剂的稳定性（抗流失），并且这种较弱的碱中心应该比较适合活化反应物，并能使形成的产物迅速从催化剂表面脱附，从而使MgO/NC-2催化剂表现出很高的催化活性。此外，NC-2载体及MgO/NC-2催化剂表面还含有一定量的含氮官能团，这些含氮官能团可能通过直接参与对反应物的活化或调整催化剂表面的亲疏水性，继而对催化剂反应活性的提高起到了积极的促进作用。
（二）介孔磷酸铝材料在碳酸二甲酯与碳酸二乙酯酯交换反应中的应用
采用柠檬酸法制备了介孔磷酸铝材料（AlPO），并将其用于碳酸二甲酯（DMC）与碳酸二乙酯（DEC）酯交换合成碳酸甲乙酯（EMC）的反应中。与微孔磷酸铝、氧化镁以及三氧化二铝等催化剂相比，介孔AlPO表现出很高的催化活性，且能在较低的反应温度下依然保持很高的催化活性，在反应温度为336K时，只需要反应3h反应即可达到反应平衡。在多相化测试反应中没有发现活性组分的流失现象，表明催化剂具有良好的稳定性。此外，反应后的催化剂经过简单的洗涤、干燥后即可实现多次循环使用，且反应活性基本保持不变，表现出了非常好的循环性，性能明显优于文献中报道的其它类型催化剂体系。
结合X射线粉末衍射、FT-IR、氮气吸附以及CO_2-TPD表征对AlPO催化剂结构以及表面性质进行了系统研究。结果表明，介孔磷酸铝表面存在丰富的弱酸弱碱中心。催化剂表面相邻的弱酸-弱碱对的存在，能够同时活化反应物碳酸二甲酯和碳酸二乙酯并形成活性中间体，如CH3O-和~+COOCH_3以及C2H5O-和+COOC2H5，这些相邻的活性中间体如~+COOCH_3以及C2H5O-之间的空间距离较近，很容易直接发生反应生成碳酸甲乙酯。由此可以认为：介孔磷酸铝催化剂表面存在的相邻的弱酸-弱碱对应该是酯交换反应的主要活性中心。
（三）铯离子交换分子筛在甲苯与甲醇侧链烷基化反应中的应用
采用离子交换法制备了铯离子交换的分子筛材料，如Cs-Y、Cs-MCM-56和Cs-IM-5等，并将其用于甲苯与甲醇侧链烷基化反应中。考察了反应温度、空速以及甲苯与甲醇投料比等对催化性能的影响，优化了反应条件。结果表明，Cs-IM-5具有很高的催化活性和对主产物（乙苯和苯乙烯）的选择性。在反应温度为708K、甲苯与甲醇摩尔比为3/1时，Cs-IM-5催化剂上甲苯转化率与苯乙烯收率分别为21.6%和8.1%，性能明显优于文献中报道的其它催化剂体系。催化剂稳定性和再生性的实验结果表明：随着反应进行，Cs-IM-5催化剂表面会形成积碳，从而使反应活性逐渐下降；在氧气气氛下，通过高温焙烧处理可以去除催化剂上的积碳，并使催化剂反应活性基本恢复。此外，采用硝酸回流的方法对IM-5分子筛进行脱铝预处理，可以对Cs-IM-5催化剂的积碳过程产生一定的抑制作用，从而提高了催化剂的稳定性。
采用原位红外光谱等技术研究了甲醇在Cs-IM-5催化剂表面的吸附行为。结果表明，甲醇的羟基易于同催化剂上的铯离子产生一定的相互作用，并且甲醇分子还能与分子筛的骨架氧形成氢键。结合其它的表征结果，推测催化剂表面存在的适合的Lewis酸和Br nsted碱中心对反应物（甲醇和甲苯）的活化起到至关重要的作用。此外，IM-5分子筛特定的孔道结构对甲苯与甲醇侧链烷基化反应中苯乙烯的生成也应该会起到一定的择形催化作用。
综上所述，本论文主要开展了一些固体酸碱催化剂（炭载MgO、介孔AlPO以及碱性沸石Cs-IM-5）的制备、表征和催化性能研究工作。得到了几种在酯交换反应以及侧链烷基化反应中催化性能比较优异的催化剂体系；并围绕催化剂活性中心性质以及反应机理等问题进行了探讨，所取得的研究结果将能为高性能固体酸碱催化剂的设计和开发提供一定的依据。
With the continuous development of environmentally friendly chemistry, greatefforts have been made to develop and improve green chemical process, especially inthe fine chemicals. Based on some defects of liquid acid and base in chemicalprocess (e.g., corrosion problem, pollution problem, separation and reuse problem),more attentions are paid to explore solid acid and base catalysts as a substitute.Heterogeneous acid and base catalysts show high catalytic activity and selectivityunder a mild condition, and they can be easily separated from reaction systems.
In this work, solid acid and base catalysts were synthesized and applied in thetransesterification reaction. The structure and surface properties of solid acid and basematerials were studied. And the effect of the support on the active site was alsoinvestigated. In addition, the catalytic reaction dynamics were studied to determinethe main kinetic parameters, including the reaction rate constant, apparent activationenergy, pre-exponential factors and so on. The main experimental results andconclusions are as follows:
1. Transesterification of carbonate with alcohols over porous carbon supportedMgO catalysts
Porous carbon-supported catalysts (MgO/NC-2), prepared by wet impregnationtechnique, showed remarkably high activity, recoverability and stability for thetransesterification of dialkyl carbonate with alcohols to unsymmetrical organiccarbonates. Besides, some characterization means were carried out in order to clarifythe role of surface functional groups of carbon materials in the formation of activesupported MgO catalysts.
Combined with different characterizations relusts (XRD, N_2adsorption/desorption,CO_2-TPD, TPD-MS, DRIFT and XPS), it is found that well-dispersed MgO/NC-2 material contains a large amount of ion pairs of Mg2+-O2-, attributed to the interactionbetween the rich oxygen-containing surface groups on the NC-2carbon support withMg species. The abundant ion pairs of Mg2+-O2-on the surface of MgO/NC-2materialshould play a critical role in the activation of the reactants in the transesterificationreactions. Besides, other surface functional groups like nitrogen-containing groupsmay also play positive role in activating reactants to produce unsymmetrical organiccarbonates.
2. Amorphous mesoporous aluminophosphate as highly efficient heterogeneouscatalysts for transesterification of diethyl carbonate with dimethyl carbonate
Mesoporous aluminophosphate (AlPO), prepared by citric acid route, were appliedto the transesterification of DEC with DMC in comparison with other solid acidand/or base catalysts. It was found that mesoporous AlPO showed high activity andstability. And the catalysts can be easily recycled without any special treatment (e.g.,heat-activation).
Combined with different characterizations relusts (XRD, N_2adsorption/desorption,and CO_2-TPD), a mechanism for the transesterification of DMC with DEC overAlPO materials was proposed. First, chemisorption of DEC and DMC could occuron the neighboring acid-base pairs simultaneously. Then the two adjacentchemisorbed species (e.g.,+COOC2H5and CH3O-) react directly to form EMC thatdesorbs easily. In addition, the abundant weak acid-base pairs on the surface ofmesoporous AlPO materials should play a critical role in the activation of thereactants in the transesterification reaction.
3. Side-chain alkylation of toluene with methanol over ion-exchanged Cs-IM-5zeolites
Cs-IM-5catalysts were prepared by ion-exchange method with cesium acetateaqueous solution. Compared with other basic zeolites (e.g., Cs-Y, Cs-MCM-56),Cs-IM-5zeolites exhibited remarkably high activity and selectivity for side-chainalkylation of toluene with methanol. Cs-IM-5and Cs-IM-5(d) prepared withdealuminated IM-5showed21.6%and26.2%conversion of toluene with8.1%and 6.0%yield of styrene, respectively. Moreover, the two catalysts showed relativelyhigh stability and recyclability.
By using a variety of characterization means, including XRD, TPD, IR spectra ofCO_2, pyridine and in situ IR spectroscopy, the physicochemical properties ofCs-IM-5zeolites were investigated. It was found that both acidic and basic siteswere present on the surface of Cs-IM-5zeolites. A certain amount Lewis acidic sites(Cs+) could interact with π-electrons of toluene and facilitate the polarization of themethyl C-H bond. And suitable basic centers could dehydrogenate methanol toformaldehyde (a key side-chain alkylating species), thus leading to high selectivitytoward styrene. Besides, the specific topology of IM-5zeolite, such as possessingmultidimensional large-pore system with intersecting12-and10-ring channel, mayprovide enough space for the formation of large intermediates and offershape-selectivity for the side-chain alkylation products.
In summary, several solid acid and base catalysts including MgO/NC-2, AlPO andCs-IM-5were prepared and investigated for the transesterification reaction andside-chain alkylation with toluene and methanol. Several excellent solid catalystswere obtained and it provides a profound understanding of the nature of the activesite, reaction mechanism and reaction kinetics, which is in favour of the preparationof high active solid acid and base catalysts for the transesterification reaction andside-chain alkylation reaction.
本文主要围绕酯交换法合成有机碳酸酯和甲苯-甲醇侧链烷基化反应开展了固体酸碱催化剂的制备、表征及催化性能研究工作。系统考察了不同方法制备的炭载氧化镁、介孔磷酸铝及Cs离子交换IM-5分子筛等催化剂体系对上述反应的催化性能；研究了催化剂组成、结构（孔径大小）和表面酸碱性质对催化剂反应性能的影响规律，并与催化剂的反应性能进行了关联；探讨了催化剂活性位性质和催化作用机制等问题。论文的主要研究内容和结果概述如下：
（一）炭载氧化镁催化剂在醇酯酯交换反应中的应用：
分别以三种炭材料（介孔炭NC-2、活性炭AC以及介孔炭CMK-3）为载体，采用浸渍法制备了负载型的MgO催化剂。考察了它们在碳酸二甲酯与乙醇酯交换以及碳酸二乙酯与各种醇类化合物酯交换反应中的催化性能。结果表明，几种炭载氧化镁都对该反应表现出了一定的催化活性，其中，MgO/NC-2材料的催化性能明显优于其它两种炭载氧化镁催化剂；在多相化测试反应中没有发现活性组分的流失现象；反应后的催化剂经过简单的焙烧处理后即可实现多次循环使用，且反应活性基本保持不变，表现出了良好的稳定性和循环性。结合催化剂的表征结果证实NC-2表面存在大量的含氧官能团，这些官能团的存在应该对MgO物种在炭载体表面实现高度分散起到了关键作用。此外，与单纯的MgO相比，负载的MgO/NC-2催化剂的碱性相对较弱，这表明MgO物种与载体NC-2之间存在一定的相互作用，这种相互作用的存在应该有助于提高催化剂的稳定性（抗流失），并且这种较弱的碱中心应该比较适合活化反应物，并能使形成的产物迅速从催化剂表面脱附，从而使MgO/NC-2催化剂表现出很高的催化活性。此外，NC-2载体及MgO/NC-2催化剂表面还含有一定量的含氮官能团，这些含氮官能团可能通过直接参与对反应物的活化或调整催化剂表面的亲疏水性，继而对催化剂反应活性的提高起到了积极的促进作用。
（二）介孔磷酸铝材料在碳酸二甲酯与碳酸二乙酯酯交换反应中的应用
采用柠檬酸法制备了介孔磷酸铝材料（AlPO），并将其用于碳酸二甲酯（DMC）与碳酸二乙酯（DEC）酯交换合成碳酸甲乙酯（EMC）的反应中。与微孔磷酸铝、氧化镁以及三氧化二铝等催化剂相比，介孔AlPO表现出很高的催化活性，且能在较低的反应温度下依然保持很高的催化活性，在反应温度为336K时，只需要反应3h反应即可达到反应平衡。在多相化测试反应中没有发现活性组分的流失现象，表明催化剂具有良好的稳定性。此外，反应后的催化剂经过简单的洗涤、干燥后即可实现多次循环使用，且反应活性基本保持不变，表现出了非常好的循环性，性能明显优于文献中报道的其它类型催化剂体系。
结合X射线粉末衍射、FT-IR、氮气吸附以及CO_2-TPD表征对AlPO催化剂结构以及表面性质进行了系统研究。结果表明，介孔磷酸铝表面存在丰富的弱酸弱碱中心。催化剂表面相邻的弱酸-弱碱对的存在，能够同时活化反应物碳酸二甲酯和碳酸二乙酯并形成活性中间体，如CH3O-和~+COOCH_3以及C2H5O-和+COOC2H5，这些相邻的活性中间体如~+COOCH_3以及C2H5O-之间的空间距离较近，很容易直接发生反应生成碳酸甲乙酯。由此可以认为：介孔磷酸铝催化剂表面存在的相邻的弱酸-弱碱对应该是酯交换反应的主要活性中心。
（三）铯离子交换分子筛在甲苯与甲醇侧链烷基化反应中的应用
采用离子交换法制备了铯离子交换的分子筛材料，如Cs-Y、Cs-MCM-56和Cs-IM-5等，并将其用于甲苯与甲醇侧链烷基化反应中。考察了反应温度、空速以及甲苯与甲醇投料比等对催化性能的影响，优化了反应条件。结果表明，Cs-IM-5具有很高的催化活性和对主产物（乙苯和苯乙烯）的选择性。在反应温度为708K、甲苯与甲醇摩尔比为3/1时，Cs-IM-5催化剂上甲苯转化率与苯乙烯收率分别为21.6%和8.1%，性能明显优于文献中报道的其它催化剂体系。催化剂稳定性和再生性的实验结果表明：随着反应进行，Cs-IM-5催化剂表面会形成积碳，从而使反应活性逐渐下降；在氧气气氛下，通过高温焙烧处理可以去除催化剂上的积碳，并使催化剂反应活性基本恢复。此外，采用硝酸回流的方法对IM-5分子筛进行脱铝预处理，可以对Cs-IM-5催化剂的积碳过程产生一定的抑制作用，从而提高了催化剂的稳定性。
采用原位红外光谱等技术研究了甲醇在Cs-IM-5催化剂表面的吸附行为。结果表明，甲醇的羟基易于同催化剂上的铯离子产生一定的相互作用，并且甲醇分子还能与分子筛的骨架氧形成氢键。结合其它的表征结果，推测催化剂表面存在的适合的Lewis酸和Br nsted碱中心对反应物（甲醇和甲苯）的活化起到至关重要的作用。此外，IM-5分子筛特定的孔道结构对甲苯与甲醇侧链烷基化反应中苯乙烯的生成也应该会起到一定的择形催化作用。
综上所述，本论文主要开展了一些固体酸碱催化剂（炭载MgO、介孔AlPO以及碱性沸石Cs-IM-5）的制备、表征和催化性能研究工作。得到了几种在酯交换反应以及侧链烷基化反应中催化性能比较优异的催化剂体系；并围绕催化剂活性中心性质以及反应机理等问题进行了探讨，所取得的研究结果将能为高性能固体酸碱催化剂的设计和开发提供一定的依据。
With the continuous development of environmentally friendly chemistry, greatefforts have been made to develop and improve green chemical process, especially inthe fine chemicals. Based on some defects of liquid acid and base in chemicalprocess (e.g., corrosion problem, pollution problem, separation and reuse problem),more attentions are paid to explore solid acid and base catalysts as a substitute.Heterogeneous acid and base catalysts show high catalytic activity and selectivityunder a mild condition, and they can be easily separated from reaction systems.
In this work, solid acid and base catalysts were synthesized and applied in thetransesterification reaction. The structure and surface properties of solid acid and basematerials were studied. And the effect of the support on the active site was alsoinvestigated. In addition, the catalytic reaction dynamics were studied to determinethe main kinetic parameters, including the reaction rate constant, apparent activationenergy, pre-exponential factors and so on. The main experimental results andconclusions are as follows:
1. Transesterification of carbonate with alcohols over porous carbon supportedMgO catalysts
Porous carbon-supported catalysts (MgO/NC-2), prepared by wet impregnationtechnique, showed remarkably high activity, recoverability and stability for thetransesterification of dialkyl carbonate with alcohols to unsymmetrical organiccarbonates. Besides, some characterization means were carried out in order to clarifythe role of surface functional groups of carbon materials in the formation of activesupported MgO catalysts.
Combined with different characterizations relusts (XRD, N_2adsorption/desorption,CO_2-TPD, TPD-MS, DRIFT and XPS), it is found that well-dispersed MgO/NC-2 material contains a large amount of ion pairs of Mg2+-O2-, attributed to the interactionbetween the rich oxygen-containing surface groups on the NC-2carbon support withMg species. The abundant ion pairs of Mg2+-O2-on the surface of MgO/NC-2materialshould play a critical role in the activation of the reactants in the transesterificationreactions. Besides, other surface functional groups like nitrogen-containing groupsmay also play positive role in activating reactants to produce unsymmetrical organiccarbonates.
2. Amorphous mesoporous aluminophosphate as highly efficient heterogeneouscatalysts for transesterification of diethyl carbonate with dimethyl carbonate
Mesoporous aluminophosphate (AlPO), prepared by citric acid route, were appliedto the transesterification of DEC with DMC in comparison with other solid acidand/or base catalysts. It was found that mesoporous AlPO showed high activity andstability. And the catalysts can be easily recycled without any special treatment (e.g.,heat-activation).
Combined with different characterizations relusts (XRD, N_2adsorption/desorption,and CO_2-TPD), a mechanism for the transesterification of DMC with DEC overAlPO materials was proposed. First, chemisorption of DEC and DMC could occuron the neighboring acid-base pairs simultaneously. Then the two adjacentchemisorbed species (e.g.,+COOC2H5and CH3O-) react directly to form EMC thatdesorbs easily. In addition, the abundant weak acid-base pairs on the surface ofmesoporous AlPO materials should play a critical role in the activation of thereactants in the transesterification reaction.
3. Side-chain alkylation of toluene with methanol over ion-exchanged Cs-IM-5zeolites
Cs-IM-5catalysts were prepared by ion-exchange method with cesium acetateaqueous solution. Compared with other basic zeolites (e.g., Cs-Y, Cs-MCM-56),Cs-IM-5zeolites exhibited remarkably high activity and selectivity for side-chainalkylation of toluene with methanol. Cs-IM-5and Cs-IM-5(d) prepared withdealuminated IM-5showed21.6%and26.2%conversion of toluene with8.1%and 6.0%yield of styrene, respectively. Moreover, the two catalysts showed relativelyhigh stability and recyclability.
By using a variety of characterization means, including XRD, TPD, IR spectra ofCO_2, pyridine and in situ IR spectroscopy, the physicochemical properties ofCs-IM-5zeolites were investigated. It was found that both acidic and basic siteswere present on the surface of Cs-IM-5zeolites. A certain amount Lewis acidic sites(Cs+) could interact with π-electrons of toluene and facilitate the polarization of themethyl C-H bond. And suitable basic centers could dehydrogenate methanol toformaldehyde (a key side-chain alkylating species), thus leading to high selectivitytoward styrene. Besides, the specific topology of IM-5zeolite, such as possessingmultidimensional large-pore system with intersecting12-and10-ring channel, mayprovide enough space for the formation of large intermediates and offershape-selectivity for the side-chain alkylation products.
In summary, several solid acid and base catalysts including MgO/NC-2, AlPO andCs-IM-5were prepared and investigated for the transesterification reaction andside-chain alkylation with toluene and methanol. Several excellent solid catalystswere obtained and it provides a profound understanding of the nature of the activesite, reaction mechanism and reaction kinetics, which is in favour of the preparationof high active solid acid and base catalysts for the transesterification reaction andside-chain alkylation reaction.
引文
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