有机—无机杂化材料固载离子液体钯催化剂的制备及催化性能研究
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摘要
均相催化剂虽然有较高的活性,但存在催化剂与产物分离困难及对反应容器腐蚀严重等缺点;而多相催化剂则易于与产物分离、回收重复使用。为使液相氧化羰化催化剂兼具均相与多相催化剂的优点,本文首次将离子液体与均相催化剂同时固载在有机-无机杂化材料上,并用于苯酚氧化羰化法合成碳酸二苯酯(DPC)反应,主要内容如下:
以2-吡啶甲醛作为有机配体,与γ-胺丙基三乙氧基硅烷反应合成席夫碱,再经NaBH4还原成仲胺,然后与正硅酸乙酯(TEOS)通过溶胶-凝胶过程合成有机-无机杂化材料(OIH),并与Pd(PhCN)_2Cl_2配位制备多相化PdCl_2/OIH催化剂。在此基础上,将合成好的四氟硼酸和六氟磷酸咪唑离子液体通过物理吸附或化学嫁接的方法固载到OIH上,制备新型固载型催化剂PdCl_2/OIH/BF_4-C、PdCl_2/OIH/BF_4-P、PdCl_2/OIH/PF_6-C、PdCl_2/OIH/PF_6-P。采用傅立叶红外光谱(FT-IR)、X-射线衍射(XRD)、固体核磁共振(~(29)SiNMR)、火焰原子吸收光谱(AA)等表征手段对载体及固载型催化剂的结构进行了表征。
考察所合成的催化剂在苯酚氧化羰化反应中的催化性能,以PdCl_2作主催化剂,Cu_2O和苯醌为助催化剂,3A分子筛作脱水剂。分别考察了均相PdCl_2、多相PdCl_2/OIH以及固载离子液体后的多相催化体系,结果表明固载离子液体后的多相PdCl_2/OIH催化剂具有更好的活性,其中PdCl_2/OIH/PF_6-C催化剂具有最好的活性,DPC产率和TON分别达到为10.5%和52.1。还考察了固载不同类型的离子液体及固载方式对催化性能的影响,结果表明采用化学嫁接固载六氟磷酸离子液体的催化剂催化性能最好。
Homogeneous catalysts show high catalytic activity, but it is usually difficult to separate the catalyst from the products and recycle the catalyst. Heterogeneous catalysts have attractive advantages over homogeneous ones, including easy removal of catalysts from reaction mixtures and recycling of the catalysts. In order to combine the advantages of both the homogeneous and heterogeneous catalysts, ionic liquids and PdCl_2 catalyst was supported on the organic-inorganic hybrid materials, and the catalytic performance of the supported catalysts in liquid phase oxidative carbonylation of phenol to diphenyl carbonate (DPC) was investigated.
PdCl_2/OIH were prepared as follows: 1) synthesis of the Schiff-bases fromγ-aminopropyltriethoxysilane and 2-pyridine-carboxaldehyde; 2) reduction of the Schiff-bases by NaBH_4 in methanol; 3) cogelification with tetraetyl orthosilicate to produce OIH; 4) Pd(PhCN)_2Cl_2 reacing with OIH materials. Synthesize [Bmim]BF_4 and [Bmim]PF_6 ionic liqueds, then support them on OIH materials by physical adsorption or chemical grafting to produce PdCl_2/OIH/BF_4-C、PdCl_2/OIH/BF_4-P、PdCl_2/OIH/PF_6-C、PdCl_2/OIH/PF_6-P catalysts. The strucure of the support and the heterogeneous catalysts were characterized by FT-IR, XRD, ~(29)SiNMR and AA.
The resultant catalysts were used in the reaction of liquid phase oxidative carbonylation of phenol to diphenyl carbonate with PdCl_2 as main catalyst, Cu_2O and tetrahydrofuran as additives, 3A molecular sieves as dehydrating agent. It was found that the heterogeneous PdCl_2/OIH catalyst showed similar catalytic activity to the homogeneous PdCl_2 catalyst. The OIH supported ionic liquids catalysts showed higher catalytic activity than the heterogeneous PdCl_2/OIH catalyst, and PdCl_2/OIH/PF_6-C catalyst revealed good catalytic activity with DPC yield and TON of 10.5% and 52.1, respectively. The catalytic activity of different ionic liquids was also studied, and PdCl_2/OIH supported [Bmim]PF_6 catalyst prepared by chemical grafting showed the best catalytic activity
以2-吡啶甲醛作为有机配体,与γ-胺丙基三乙氧基硅烷反应合成席夫碱,再经NaBH4还原成仲胺,然后与正硅酸乙酯(TEOS)通过溶胶-凝胶过程合成有机-无机杂化材料(OIH),并与Pd(PhCN)_2Cl_2配位制备多相化PdCl_2/OIH催化剂。在此基础上,将合成好的四氟硼酸和六氟磷酸咪唑离子液体通过物理吸附或化学嫁接的方法固载到OIH上,制备新型固载型催化剂PdCl_2/OIH/BF_4-C、PdCl_2/OIH/BF_4-P、PdCl_2/OIH/PF_6-C、PdCl_2/OIH/PF_6-P。采用傅立叶红外光谱(FT-IR)、X-射线衍射(XRD)、固体核磁共振(~(29)SiNMR)、火焰原子吸收光谱(AA)等表征手段对载体及固载型催化剂的结构进行了表征。
考察所合成的催化剂在苯酚氧化羰化反应中的催化性能,以PdCl_2作主催化剂,Cu_2O和苯醌为助催化剂,3A分子筛作脱水剂。分别考察了均相PdCl_2、多相PdCl_2/OIH以及固载离子液体后的多相催化体系,结果表明固载离子液体后的多相PdCl_2/OIH催化剂具有更好的活性,其中PdCl_2/OIH/PF_6-C催化剂具有最好的活性,DPC产率和TON分别达到为10.5%和52.1。还考察了固载不同类型的离子液体及固载方式对催化性能的影响,结果表明采用化学嫁接固载六氟磷酸离子液体的催化剂催化性能最好。
Homogeneous catalysts show high catalytic activity, but it is usually difficult to separate the catalyst from the products and recycle the catalyst. Heterogeneous catalysts have attractive advantages over homogeneous ones, including easy removal of catalysts from reaction mixtures and recycling of the catalysts. In order to combine the advantages of both the homogeneous and heterogeneous catalysts, ionic liquids and PdCl_2 catalyst was supported on the organic-inorganic hybrid materials, and the catalytic performance of the supported catalysts in liquid phase oxidative carbonylation of phenol to diphenyl carbonate (DPC) was investigated.
PdCl_2/OIH were prepared as follows: 1) synthesis of the Schiff-bases fromγ-aminopropyltriethoxysilane and 2-pyridine-carboxaldehyde; 2) reduction of the Schiff-bases by NaBH_4 in methanol; 3) cogelification with tetraetyl orthosilicate to produce OIH; 4) Pd(PhCN)_2Cl_2 reacing with OIH materials. Synthesize [Bmim]BF_4 and [Bmim]PF_6 ionic liqueds, then support them on OIH materials by physical adsorption or chemical grafting to produce PdCl_2/OIH/BF_4-C、PdCl_2/OIH/BF_4-P、PdCl_2/OIH/PF_6-C、PdCl_2/OIH/PF_6-P catalysts. The strucure of the support and the heterogeneous catalysts were characterized by FT-IR, XRD, ~(29)SiNMR and AA.
The resultant catalysts were used in the reaction of liquid phase oxidative carbonylation of phenol to diphenyl carbonate with PdCl_2 as main catalyst, Cu_2O and tetrahydrofuran as additives, 3A molecular sieves as dehydrating agent. It was found that the heterogeneous PdCl_2/OIH catalyst showed similar catalytic activity to the homogeneous PdCl_2 catalyst. The OIH supported ionic liquids catalysts showed higher catalytic activity than the heterogeneous PdCl_2/OIH catalyst, and PdCl_2/OIH/PF_6-C catalyst revealed good catalytic activity with DPC yield and TON of 10.5% and 52.1, respectively. The catalytic activity of different ionic liquids was also studied, and PdCl_2/OIH supported [Bmim]PF_6 catalyst prepared by chemical grafting showed the best catalytic activity
引文
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[7] Ishii H, Takeuchi K, Asai M. et al. Oxidative Carbonylation of Phenol to Diphenyl Carbonate Catalyzed by Pd-pyridyl Complexes Tethered on Polymer Support. Catal Commun, 2001, 2(3-4): 145～150
[8] Hui X F, Rong M W, Shu B L. et al. Preparation and Catalytic activity of Polymer-bound 1,10-Phenantholine and its Complexes Reactive Functional Polymers , 1999, 42(2): 87～92
[9]刘海涛,熊辉,莫婉玲等. CuCl/菲咯啉/甲基咪唑催化甲醇/乙醇氧化羰化一步合成碳酸甲乙酯,催化学报, 2004, 25(3): 243～246
[10] Mieke D, De V, Pierre A J. et al. Ordered Mesoporous and Microporous Molecular Sieves Functionalized with Transition Metal Complexes as Catalyst for Selective Organic Transformations. Chem Rev, 2002, 102(10): 3615～3640
[11]王峰.多相催化选择氧化甲苯合成芳香醛类化合物的研究:[博士学位论文].保存地点:中国科学院大连化学物理研究所,2005.
[12] Iwane H, Hidekau M, Satoshi I. et al. Method of Preparing Aromatic Carbonates. US Patent 5543574, 1996.
[13] Beck J S, Vartuli J C, Roth W J. et al. A New Family of Mesoporous Molecular Sieves Prepared with Liquid Crystal Templates. J Am Chem Soc, 1992, 114(27): 10834～10843.
[14]刘持标,叶兴凯,吴越.八羟基喹啉铁/MCM-41对苯酚羟化的催化作用.催化学报, 1997, 18(2): 1402～1431
[15] Astruc D, Chardac F. Dendritic Catalysts and Dendrimers in Catalysis. Chem Rev, 2001, 101(9): 2991～3003
[16] Wight A P, Davis M E. Design and Preparation of Organic-Inorganic Hybrid Catalysts. Chem. Rev, 2002, 102(10): 3589～3614
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