石墨烯基材料的制备及其在多相催化中的应用
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摘要
石墨烯是一种新型碳材料,其组成可控、易官能化,石墨烯的表面积较大且表面利用效率高,具有良好的耐酸碱和耐高温等特性；与此同时,通过改变石墨烯的组成还可以有效调控其在不同介质中的分散特性。因此,相比于传统的活性炭和碳纳米管,石墨烯有望成为一种新的、高效的催化剂载体。本论文以石墨烯、氧化石墨烯(GO)、氮杂石墨烯为载体,先后合成了系列石墨烯负载的金属(Pt,Pd)、氧化物(MnO2,Co3O4)及复合的金属-氧化物(Pd-Ni2O3)催化剂,并探讨了这些催化剂在多相催化中的应用。
首先,采用乙二醇直接还原法制备了石墨烯负载的纳米Pt催化齐(Pt/RGO_EG),并考察了其在芳香硝基化合物加氢反应中的活性规律。研究发现：在0℃,Pt/RGO-EG催化硝基苯加氢的比活性高达70.2mol-AN/(mol-pt·min),是活性炭和碳纳米管负载的Pt催化剂的19.5和12.5倍；当温度升至20℃,催化剂活性骤升至1138.3mol-AN/(mol-Pt·min)。这种催化剂可以在温和条件下实现系列硝基化合物的选择性加氢。我们认为,这种优异的催化活性不仅与石墨烯表面高分散的Pt纳米颗粒有关,而且还与催化剂在溶剂中的高分散性有关。
其次,为了探索石墨烯的可塑性,在石墨烯负载钯的同时引入了Ni203,借助Ni203颗粒的隔离效应来协助调控Pd的形貌和稳定性。结果发现：Ni203颗粒的加入,可以有效剥离石墨烯片层、促进Pd的分散、改进载体在介质中的分散以及对底物的富集作用。这种复合的Pd-Ni/RGO催化剂在偶联反应中表现出明显优于传统的钯碳和均相催化剂的活性,在80℃下进行的溴苯偶联反应中,单个Pd原子的比活性最高可达38,750h-1,而且催化剂可以重复使用。而单纯的Pd与石墨烯的作用较弱、活性及稳定性均不如复合的Pd-Ni/RGO催化剂。
为满足可持续发展的需求,本文还探究石墨烯上廉价活性物种的可控合成。在异丙醇-水组成的溶剂中、利用GO表面含氧官能团的静电作用,引导Mn02沿轴向生长,制备了特殊的MnO2纳米棒。通过优化GO的添加量、回流时间等,总结出MnO2纳米棒的可控生长规律。GO与MnO2的结合可以促进石墨烯片层的剥离、增加催化剂的表面积、改善活性组分的亲水性能。这种催化剂(MnO2/GO)特别适合于水相中芳香醇的一步氨氧化反应；催化剂活性高、稳定性好,而且产物的分离提纯简单,满足绿色化学的发展理念。
为进一步增强石墨烯载体与负载活性组分之间的作用,本文尝试对石墨烯载体的组成进行调控。通过在水热合成过程中添加配体(氨水)实现了对石墨烯载体的氮掺杂,同时氨水的加入还可以有效控制石墨烯表面上C0304的形貌。相比于纯碳石墨烯负载的C0304和单纯的Co3O4, Co3O4/RGO-N复合物在烯烃和芳香醇的选择性氧化反应中具有更高的活性和稳定性。表征结果表明：石墨烯中的氮原子可以抑制其再石墨化、增强活性组分与载体之间的相互作用、改善其分散性。
最后,本文采用分步法设计和构筑法制备了多功能的Pd/NRGO催化剂。先采用尿素水热法制备氮杂石墨烯,然后利用载体的“非均相配体”作用原位捕捉pd2+,并在H2气氛下还原制得Pd纳米颗粒。通过调控石墨烯中氮的含量,研究了氮杂石墨烯对活性组分形貌的控制和对底物分子的作用机制,从理论上深入探讨了氮杂石墨烯的催化机理。将所制备的催化剂用于肉桂醛的加氢测试,结果发现这种催化剂即使在水溶剂中也具有明显优于非氮杂催化剂的活性和产物选择性,且对各类不饱和化合物的水相加氢具有广泛的适用性。表征结果发现：石墨烯中的氮原子有利于形成高分散、超小尺寸和高稳定性的Pd纳米颗粒,这主要是由于载体与Pd之间的作用随着氮含量的增加而增强。理论计算结果表明：石墨烯的氮杂降低了H从Pd溢流至载体的能垒、促进了氢的活化、加速了反应的进行；同时氮杂石墨烯上的电子可以传递给C=O双键、保护C=O双键,从而间接提升C=C双键的活化和选择性转化。
总之,本论文对石墨烯基催化剂载体的制备和应用进行了初步的探索,为拓展这种新型碳材料的应用供了经验。
Graphene is a kind of new carbon material, which is not only easily controlled in composition and function, but also possesses high utilization efficiency toward large surface area, good resistance to acid/alkali and high temperature. At the same time, the adjustment of composition allows graphene well dispersing in different kinds of solvents. Therefore, compared with the traditional activated carbon and carbon nanotubes, graphene is expected to become a new and efficient catalyst support. Herein, graphene and graphene oxide, nitrogen doped graphene are used as supports for fabricating metal (Pt, Pd), metal oxide (MnO2, Co3O4) and hybrid metal-metal oxide (Pd-Ni2Os) catalysts, and their applications in heterogeneous catalysis are also discussed.
Firstly, reduced graphene oxide (RGO)-supported platinum (Pt) catalyst was prepared by simple ethylene glycol (EG) reduction and used for the hydrogenation of aromatic nitro compounds. Characterizations showed that EG as a reductant exhibited many more advantages than the widely used hydrazine hydrate to fabricate monodispersed, small sized Pt nanoparticles on the surface of RGO. The yield of aniline over the Pt/RGO-EG catalyst reached70.2mol-AN/(mol-p1·min) at0℃, which is12.5and19.5times higher than that of multi-walled carbon nanotube-and active carbon-supported Pt catalysts, respectively. When the reaction temperature was increased to20℃, the catalytic activity of Pt/RGO-EG jumped to1138.3mol-AN/(mol-pt·min), and it was also extremely active for the hydrogenation of a series of aromatic nitro compounds. The unique catalytic activity of Pt/RGO-EG is not only related to the well dispersed Pt clusters on the RGO sheets but also the well dispersion of Pt/RGO-EG in the reaction mixture.
The active component can be modulated for further exploring the application scope of graphene. Here, Ni2O3-around-Pd hybrid can be fabricated on graphene oxide (Pd-Ni/RGO) by a simple one-pot wet chemical route. These isolated Pd clusters showed significantly improved performance for Suzuki coupling reaction compared to that of pure Pd/RGO, Ni2O3/RGO, popularly reported Pd/AC, as well as homogeneous PdCl2and PdCl2(PPh3)2. Characterizations disclosed that Ni2O3plays a multiple roles in exfoliating graphene sheets, mediating the size as well as stability of Pd clusters. Pd-Ni/RGO dispersed homogeneously in the aqueous reaction mixture, exhibited high enrichment towards reactants as well as extremely high activity and stability for the Suzuki coupling reaction. The best turnover frequencies of all Pd atoms reached38750h-1at80℃for bromobenzene coupling. It was concluded that the intimate interaction between Ni2O3nanoparticles and Pd clusters appears to be beneficial for activating the Pd surface for the catalytic cycle.
To meet the sustainable development need, exploring the controllable synthesis of cheap active species on graphene is also carried out. Here, well-organized MnCO2nanorods on graphene oxide (MnO2/GO) were fabricated though a novel and easily controlled chemical route. The rod-like MnO2with5-20nm in diameter and100-600nm in length, uniformly and densely attached on both side of GO sheets. Compared with the bare MnO2, MnO2/GO nanocomposite is an efficient heterogeneous catalyst for a widely applicable synthesis of primary amides from primary alcohols and ammonia as well as for transformation of aldehydes or nitriles. More importantly, water is a superior medium for this reaction than other commonly used organic solvents, which is beneficial for catalyst/product separation. MnO2/GO catalyst has good recyclability in these reactions. High dispersion in water, high MnO dispersion on GO and suitable functional groups on carbon materials are important for a synergistic ammoxidation catalytic activity of MnO2and GO in the hybrid.
Attempts to control the dispersion and durability of catalytic metal NPs are essential to catalytic performance and economical feasibility, which implys us to strengthen the interaction between support and active species by introducing dopant and defect into the graphene. Here, a sandwich-like N-doped graphene/Co3O4hybrid was prepared via a simple one-pot hydrothermal reaction in the solution of NH3. Characterizations disclosed that highly dispersed Co3O4nanoparticles with dominant exposed {112} and {110} planes were fabricated on both sides of well-exfoliated N-doped graphene, N-dopants in graphene matrix can prevent re-graphitization of graphene, strengthen the interaction between Co3O4and graphene matrix, and improve the dispersion of Co3O4. This hybrid (Co3O4/RGO-N) exhibited predominant activity and stability for the epoxidation of styrene than bulk Co3O4and N-free graphene supported Co3O4. At the same time, the resulting catalyst also showed high compatibility to various olefins and alcohols with good conversion and high selectivity.
In order to further explore the effect of support modification on the active component and its catalytic performance, the catalyst is fabricated by two-step method. Here, N-doped graphene, which is synthesized via a facial one-step hydrothermal reaction of graphene oxide with urea, is especially adapted for anchoring extremely ultrafine and highly stabilized Pd clusters under a very "clean" strategy using H2as reductant. This in situ hydrogen-water strategy allows catalyst self-assembly at atom level, and the adjustment of concentration of doped N in graphene results in a significant variation of Pd morphology. This N-doped graphene supported Pd (Pd/NRGO) is exclusively selective for the activation of C=C or benzene ring in aqueous medium. Our experimental work shows N-doped graphene is not only a good support for strong anchorage of Pd, and its well dispersion in both water and substrate phase, but also a powerful mediator in tuning reaction path. Density functional theory calculations disclosed that N dopants can obviously enhance the binding of Pd atom with graphene, decrease the barrier of H spillover from Pd to support, and promote the electrons transfer from support to substrate that protected C=O group and improved the activation of C=C.
In conclusion, this thesis has carried out the preliminary exploration on both the preparation and application of graphene based catalyst supports. We except our research can provide simple, efficient and versatile blue-prints for low-cost fabrication of graphene-based nanocomposites for extending applications where graphene has rarely been exploited and beyond.
首先,采用乙二醇直接还原法制备了石墨烯负载的纳米Pt催化齐(Pt/RGO_EG),并考察了其在芳香硝基化合物加氢反应中的活性规律。研究发现：在0℃,Pt/RGO-EG催化硝基苯加氢的比活性高达70.2mol-AN/(mol-pt·min),是活性炭和碳纳米管负载的Pt催化剂的19.5和12.5倍；当温度升至20℃,催化剂活性骤升至1138.3mol-AN/(mol-Pt·min)。这种催化剂可以在温和条件下实现系列硝基化合物的选择性加氢。我们认为,这种优异的催化活性不仅与石墨烯表面高分散的Pt纳米颗粒有关,而且还与催化剂在溶剂中的高分散性有关。
其次,为了探索石墨烯的可塑性,在石墨烯负载钯的同时引入了Ni203,借助Ni203颗粒的隔离效应来协助调控Pd的形貌和稳定性。结果发现：Ni203颗粒的加入,可以有效剥离石墨烯片层、促进Pd的分散、改进载体在介质中的分散以及对底物的富集作用。这种复合的Pd-Ni/RGO催化剂在偶联反应中表现出明显优于传统的钯碳和均相催化剂的活性,在80℃下进行的溴苯偶联反应中,单个Pd原子的比活性最高可达38,750h-1,而且催化剂可以重复使用。而单纯的Pd与石墨烯的作用较弱、活性及稳定性均不如复合的Pd-Ni/RGO催化剂。
为满足可持续发展的需求,本文还探究石墨烯上廉价活性物种的可控合成。在异丙醇-水组成的溶剂中、利用GO表面含氧官能团的静电作用,引导Mn02沿轴向生长,制备了特殊的MnO2纳米棒。通过优化GO的添加量、回流时间等,总结出MnO2纳米棒的可控生长规律。GO与MnO2的结合可以促进石墨烯片层的剥离、增加催化剂的表面积、改善活性组分的亲水性能。这种催化剂(MnO2/GO)特别适合于水相中芳香醇的一步氨氧化反应；催化剂活性高、稳定性好,而且产物的分离提纯简单,满足绿色化学的发展理念。
为进一步增强石墨烯载体与负载活性组分之间的作用,本文尝试对石墨烯载体的组成进行调控。通过在水热合成过程中添加配体(氨水)实现了对石墨烯载体的氮掺杂,同时氨水的加入还可以有效控制石墨烯表面上C0304的形貌。相比于纯碳石墨烯负载的C0304和单纯的Co3O4, Co3O4/RGO-N复合物在烯烃和芳香醇的选择性氧化反应中具有更高的活性和稳定性。表征结果表明：石墨烯中的氮原子可以抑制其再石墨化、增强活性组分与载体之间的相互作用、改善其分散性。
最后,本文采用分步法设计和构筑法制备了多功能的Pd/NRGO催化剂。先采用尿素水热法制备氮杂石墨烯,然后利用载体的“非均相配体”作用原位捕捉pd2+,并在H2气氛下还原制得Pd纳米颗粒。通过调控石墨烯中氮的含量,研究了氮杂石墨烯对活性组分形貌的控制和对底物分子的作用机制,从理论上深入探讨了氮杂石墨烯的催化机理。将所制备的催化剂用于肉桂醛的加氢测试,结果发现这种催化剂即使在水溶剂中也具有明显优于非氮杂催化剂的活性和产物选择性,且对各类不饱和化合物的水相加氢具有广泛的适用性。表征结果发现：石墨烯中的氮原子有利于形成高分散、超小尺寸和高稳定性的Pd纳米颗粒,这主要是由于载体与Pd之间的作用随着氮含量的增加而增强。理论计算结果表明：石墨烯的氮杂降低了H从Pd溢流至载体的能垒、促进了氢的活化、加速了反应的进行；同时氮杂石墨烯上的电子可以传递给C=O双键、保护C=O双键,从而间接提升C=C双键的活化和选择性转化。
总之,本论文对石墨烯基催化剂载体的制备和应用进行了初步的探索,为拓展这种新型碳材料的应用供了经验。
Graphene is a kind of new carbon material, which is not only easily controlled in composition and function, but also possesses high utilization efficiency toward large surface area, good resistance to acid/alkali and high temperature. At the same time, the adjustment of composition allows graphene well dispersing in different kinds of solvents. Therefore, compared with the traditional activated carbon and carbon nanotubes, graphene is expected to become a new and efficient catalyst support. Herein, graphene and graphene oxide, nitrogen doped graphene are used as supports for fabricating metal (Pt, Pd), metal oxide (MnO2, Co3O4) and hybrid metal-metal oxide (Pd-Ni2Os) catalysts, and their applications in heterogeneous catalysis are also discussed.
Firstly, reduced graphene oxide (RGO)-supported platinum (Pt) catalyst was prepared by simple ethylene glycol (EG) reduction and used for the hydrogenation of aromatic nitro compounds. Characterizations showed that EG as a reductant exhibited many more advantages than the widely used hydrazine hydrate to fabricate monodispersed, small sized Pt nanoparticles on the surface of RGO. The yield of aniline over the Pt/RGO-EG catalyst reached70.2mol-AN/(mol-p1·min) at0℃, which is12.5and19.5times higher than that of multi-walled carbon nanotube-and active carbon-supported Pt catalysts, respectively. When the reaction temperature was increased to20℃, the catalytic activity of Pt/RGO-EG jumped to1138.3mol-AN/(mol-pt·min), and it was also extremely active for the hydrogenation of a series of aromatic nitro compounds. The unique catalytic activity of Pt/RGO-EG is not only related to the well dispersed Pt clusters on the RGO sheets but also the well dispersion of Pt/RGO-EG in the reaction mixture.
The active component can be modulated for further exploring the application scope of graphene. Here, Ni2O3-around-Pd hybrid can be fabricated on graphene oxide (Pd-Ni/RGO) by a simple one-pot wet chemical route. These isolated Pd clusters showed significantly improved performance for Suzuki coupling reaction compared to that of pure Pd/RGO, Ni2O3/RGO, popularly reported Pd/AC, as well as homogeneous PdCl2and PdCl2(PPh3)2. Characterizations disclosed that Ni2O3plays a multiple roles in exfoliating graphene sheets, mediating the size as well as stability of Pd clusters. Pd-Ni/RGO dispersed homogeneously in the aqueous reaction mixture, exhibited high enrichment towards reactants as well as extremely high activity and stability for the Suzuki coupling reaction. The best turnover frequencies of all Pd atoms reached38750h-1at80℃for bromobenzene coupling. It was concluded that the intimate interaction between Ni2O3nanoparticles and Pd clusters appears to be beneficial for activating the Pd surface for the catalytic cycle.
To meet the sustainable development need, exploring the controllable synthesis of cheap active species on graphene is also carried out. Here, well-organized MnCO2nanorods on graphene oxide (MnO2/GO) were fabricated though a novel and easily controlled chemical route. The rod-like MnO2with5-20nm in diameter and100-600nm in length, uniformly and densely attached on both side of GO sheets. Compared with the bare MnO2, MnO2/GO nanocomposite is an efficient heterogeneous catalyst for a widely applicable synthesis of primary amides from primary alcohols and ammonia as well as for transformation of aldehydes or nitriles. More importantly, water is a superior medium for this reaction than other commonly used organic solvents, which is beneficial for catalyst/product separation. MnO2/GO catalyst has good recyclability in these reactions. High dispersion in water, high MnO dispersion on GO and suitable functional groups on carbon materials are important for a synergistic ammoxidation catalytic activity of MnO2and GO in the hybrid.
Attempts to control the dispersion and durability of catalytic metal NPs are essential to catalytic performance and economical feasibility, which implys us to strengthen the interaction between support and active species by introducing dopant and defect into the graphene. Here, a sandwich-like N-doped graphene/Co3O4hybrid was prepared via a simple one-pot hydrothermal reaction in the solution of NH3. Characterizations disclosed that highly dispersed Co3O4nanoparticles with dominant exposed {112} and {110} planes were fabricated on both sides of well-exfoliated N-doped graphene, N-dopants in graphene matrix can prevent re-graphitization of graphene, strengthen the interaction between Co3O4and graphene matrix, and improve the dispersion of Co3O4. This hybrid (Co3O4/RGO-N) exhibited predominant activity and stability for the epoxidation of styrene than bulk Co3O4and N-free graphene supported Co3O4. At the same time, the resulting catalyst also showed high compatibility to various olefins and alcohols with good conversion and high selectivity.
In order to further explore the effect of support modification on the active component and its catalytic performance, the catalyst is fabricated by two-step method. Here, N-doped graphene, which is synthesized via a facial one-step hydrothermal reaction of graphene oxide with urea, is especially adapted for anchoring extremely ultrafine and highly stabilized Pd clusters under a very "clean" strategy using H2as reductant. This in situ hydrogen-water strategy allows catalyst self-assembly at atom level, and the adjustment of concentration of doped N in graphene results in a significant variation of Pd morphology. This N-doped graphene supported Pd (Pd/NRGO) is exclusively selective for the activation of C=C or benzene ring in aqueous medium. Our experimental work shows N-doped graphene is not only a good support for strong anchorage of Pd, and its well dispersion in both water and substrate phase, but also a powerful mediator in tuning reaction path. Density functional theory calculations disclosed that N dopants can obviously enhance the binding of Pd atom with graphene, decrease the barrier of H spillover from Pd to support, and promote the electrons transfer from support to substrate that protected C=O group and improved the activation of C=C.
In conclusion, this thesis has carried out the preliminary exploration on both the preparation and application of graphene based catalyst supports. We except our research can provide simple, efficient and versatile blue-prints for low-cost fabrication of graphene-based nanocomposites for extending applications where graphene has rarely been exploited and beyond.
引文
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