介孔碳材料负载铂催化剂及氧化铝包埋铂催化剂的制备、表征及其不对称催化氢化性能研究
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摘要
有序介孔碳材料是近年来发展起来的一类新型的非硅基介孔材料,既具有均一的孔径、高度有序的孔道分布和巨大的比表面积等优点,又具有疏水性高、易修饰和良好的机械稳定性等优点。MPC型介孔碳材料是一种具有p6mm结构对称性的新型介孔碳材料。它首先以F127为模板剂、预聚的酚醛树脂为有机源,正硅酸乙酯(TEOS)为无机源,通过溶剂挥发自组装合成有机-无机杂化树脂硅材料,然后再将树脂硅材料经氮气氛围高温炭化和氢氟酸去硅后得到有序介孔碳材料MP-C-61。这是目前一种可以通过“一步法”合成的具有高比表面积(1600m2/g)和大孔容(1.22 cm3/g)的新型介孔碳材料。因此,本论文选择此类新型介孔碳材料,负载贵金属铂催化剂,再通过手性分子对其表面进行修饰后用于α-酮酸酯的多相不对称催化氢化反应中。
在论文的第一部分工作中,采用氯铂酸的乙醇溶液和水溶液为铂前驱体通过浸渍法分别制备了介孔碳材料MP-C-61负载的质量分数为4%和10%的催化剂Pt/MP-C-61,并利用XRD、TEM、N2气吸脱附和CO化学吸附等手段对催化剂进行了表征。考察了经过手性分子辛可尼定修饰后的Pt/MP-C-61催化剂在丙酮酸乙酯不对称氢化反应中的催化性能。对于担载量4%的催化剂,以氯铂酸乙醇溶液为前体制备的催化剂因其具有较小的粒径和较高的分散度而表现出较高的催化活性。而以氯铂酸水溶液为前体制备的催化剂则具有较强的手性诱导能力,前体经150℃真空焙烧的催化剂上无论是转化率还是光学选择性均有所提高,水溶剂中的TOF值高达8820 h-1。对于担载量10%的催化剂,在乙酸溶剂中对(R)-(+)-乳酸乙酯的光学选择性可以达到66% e.e.。值得指出的是,担载量为4%的Pt/MP-C-61催化剂表现出比质量分数为5%的商品化Pt/C更高的催化活性。Cat-4Pt-W催化剂在水溶剂中可以重复使用高达10次以上。还将担载量为4%的催化剂用于手性药物依那普利前体(EOPB)的不对称合成中,所有催化剂上EOPB的转化率均为100%。前体经150℃真空焙烧的催化剂在乙酸溶剂中可以取得61% e.e.的光学选择性。
近年来,氧化铝负载的铂催化剂(Pt/Al2O3)经手性分子修饰后用于潜手性羰基化合物的不对称催化氢化被当作多相不对称催化领域的一个里程碑。由于传统的氧化铝比表面积小,孔径分布较宽,所以制备出高比表面积、孔道有序和较高热稳定性的介孔氧化铝(MA)一直是这一领域的研究目标。简单溶胶-凝胶法是目前最常用的一种合成介孔氧化铝的方法。
在本论文的第二部分工作中,我们利用“一步法”将Pt纳米粒子引入介孔氧化铝的孔道里,合成了介孔氧化铝包埋的铂纳米粒子催化剂,并将催化剂应用到丙酮酸乙酯的不对称氢化反应中。研究结果表明：在利用“一步法”合成的不同Pt担载量和催化剂前体经不同气氛焙烧的所有催化剂xPt/MA中,Pt担载量为3%并于还原前在空气中焙烧的催化剂3Pt/MA(E)-A经95℃甲酸钠水溶液还原后,仍然保持着良好的介孔结构和Pt粒子的分散状态,所以它表现出最好的催化性能,其对丙酮酸乙酯的转化率为83.5%,对(R)-(+)-乳酸乙酯的光学选择性为74.4% e.e.,甚至优于浸渍法制备的担载量为5%的催化剂E-5Pt/MA。
The well-ordered carbon materials are a class of advanced non-silicon materials, which possess the textural porosities of mesoporous materials with uniform pore size, well-ordered mesopores and high specific surface area, and simultaneously possess the merits of carbons with high hydrophobicity, easy functionalization and high mechanical stability. MP-C-type mesoporous carbon materials, derived from ordered mesoporous polymer-silica which is calcined under N2 flow and and then removed silica by HF etching, are a class of newly-developed advanced materials, with two-dimensional hexagonal p6mm symmetry, large pore volumes (1.22 cm3/g) and high surface areas (1600 m2/g). They have been successfully synthesized via one pot synthesis of solvent evaporation self-assembly (EISA), wherein soluble resol polymer is used as an organic precursor; TEOS is used as an inorganic precursor, and triblock copolymer F127 is used as a template. The application of MP-C-type OMCs supported Pt nanoparticles in heterogeneous asymmetric hydrogenation ofα-functionalized ketones has been rarely reported up to now.
In the first part,4% and 10%(mass fraction) Pt catalysts supported on MP-C-61 were prepared by an impregnation method using two different Pt precursors, ethanolic solution and aqueous solution of H2PtCl6.These Pt/MP-C-61 catalysts were characterized by XRD, N2-sorption, TEM and CO chemisorption. The Pt/MP-C-61 catalysts can be effectively applied in the asymmetric hydrogenation of ethyl pyruvate after chirally modified with cinchonidine. The Cat-4Pt-E catalyst derived from the ethanolic solution of H2PtCl6 afforded better conversions of ethyl pyruvate due to smaller Pt particle size with higher Pt dispersion. While the Cat-4Pt-W catalysts derived from the aqueous solution of H2PtCl6 showed higher chiral induction ability. The catalyst Cat-4Pt-W-150 that was calcined at 150℃under vacuum gave higher conversion and higher enantioselectivity than Cat-4Pt-W did, the highest TOF reaching 8820 h-1 in water. A 66% e.e. value was furnished by Cat-lOPt-E catalyst in acetic acid. In particular, the Cat-4Pt-W catalyst showed superior catalytic activity to the 5% mass fraction of commercial Pt/C catalyst, mainly due to the ordered mesoporous structure feature of MP-C-61 support. Moreover, Cat-4Pt-W can be recycled easily for more than 10 times without distinct loss activity or enantioselectivity in the water. The 4% Pt catalysts supported on MP-C-61 can also be effectively applied in the asymmetric hydrogenation of ethyl 2-oxo-4-phenylbutyrate, of which the hydrogenation product can be used to produce A.C.E inhibitors. Under the optimal conditions, the catalyst Cat-4Pt-W-150 gave a 61% e.e. value of (R)-(+)-ethyl 2-hydroxyl-4-phenylbutyrate in acetic acid.
In recent years, Pt/Al2O3 has also been successfully applied to the heterogeneous enantioselective hydrogenation of a-functionalized ketones. It is a target to prepare ordered mesoporous alumina with high surface area, ordered pore channel and high thermal stability due toγ-Al2O3 has lower surface area and wide Pore-size distribution. Simple sol-gel route is a high-throughput method to synthesize MA as reported in the literature.
In the second part, we prepared the highly ordered Pt-containing mesoporous alumina catalyst by one-pot synthesis and investigated the catalytic performance in the heterogeneous enantioselective hydrogenation of ethyl pyruvate after modifying the catalysts with cinchonidine. Among all the xPt/MA catalysts prepared by the one-pot method with different Pt loadings and ever calcined in different atomsphere, 3Pt/MA(E)-A, which possessed 3 wt.% Pt loading and was calcined in air before reduction, maintained the mesoporous structure well and had high dispersion of Pt particles, so it showed the best catalytic performance, as a result,83.5% conversion of ethyl pyruvate was obtained with 74.4% e.e. value of (R)-(+)-ethyl lactate, which is even better than 5Pt/MA prepared via an impregnation method.
在论文的第一部分工作中,采用氯铂酸的乙醇溶液和水溶液为铂前驱体通过浸渍法分别制备了介孔碳材料MP-C-61负载的质量分数为4%和10%的催化剂Pt/MP-C-61,并利用XRD、TEM、N2气吸脱附和CO化学吸附等手段对催化剂进行了表征。考察了经过手性分子辛可尼定修饰后的Pt/MP-C-61催化剂在丙酮酸乙酯不对称氢化反应中的催化性能。对于担载量4%的催化剂,以氯铂酸乙醇溶液为前体制备的催化剂因其具有较小的粒径和较高的分散度而表现出较高的催化活性。而以氯铂酸水溶液为前体制备的催化剂则具有较强的手性诱导能力,前体经150℃真空焙烧的催化剂上无论是转化率还是光学选择性均有所提高,水溶剂中的TOF值高达8820 h-1。对于担载量10%的催化剂,在乙酸溶剂中对(R)-(+)-乳酸乙酯的光学选择性可以达到66% e.e.。值得指出的是,担载量为4%的Pt/MP-C-61催化剂表现出比质量分数为5%的商品化Pt/C更高的催化活性。Cat-4Pt-W催化剂在水溶剂中可以重复使用高达10次以上。还将担载量为4%的催化剂用于手性药物依那普利前体(EOPB)的不对称合成中,所有催化剂上EOPB的转化率均为100%。前体经150℃真空焙烧的催化剂在乙酸溶剂中可以取得61% e.e.的光学选择性。
近年来,氧化铝负载的铂催化剂(Pt/Al2O3)经手性分子修饰后用于潜手性羰基化合物的不对称催化氢化被当作多相不对称催化领域的一个里程碑。由于传统的氧化铝比表面积小,孔径分布较宽,所以制备出高比表面积、孔道有序和较高热稳定性的介孔氧化铝(MA)一直是这一领域的研究目标。简单溶胶-凝胶法是目前最常用的一种合成介孔氧化铝的方法。
在本论文的第二部分工作中,我们利用“一步法”将Pt纳米粒子引入介孔氧化铝的孔道里,合成了介孔氧化铝包埋的铂纳米粒子催化剂,并将催化剂应用到丙酮酸乙酯的不对称氢化反应中。研究结果表明：在利用“一步法”合成的不同Pt担载量和催化剂前体经不同气氛焙烧的所有催化剂xPt/MA中,Pt担载量为3%并于还原前在空气中焙烧的催化剂3Pt/MA(E)-A经95℃甲酸钠水溶液还原后,仍然保持着良好的介孔结构和Pt粒子的分散状态,所以它表现出最好的催化性能,其对丙酮酸乙酯的转化率为83.5%,对(R)-(+)-乳酸乙酯的光学选择性为74.4% e.e.,甚至优于浸渍法制备的担载量为5%的催化剂E-5Pt/MA。
The well-ordered carbon materials are a class of advanced non-silicon materials, which possess the textural porosities of mesoporous materials with uniform pore size, well-ordered mesopores and high specific surface area, and simultaneously possess the merits of carbons with high hydrophobicity, easy functionalization and high mechanical stability. MP-C-type mesoporous carbon materials, derived from ordered mesoporous polymer-silica which is calcined under N2 flow and and then removed silica by HF etching, are a class of newly-developed advanced materials, with two-dimensional hexagonal p6mm symmetry, large pore volumes (1.22 cm3/g) and high surface areas (1600 m2/g). They have been successfully synthesized via one pot synthesis of solvent evaporation self-assembly (EISA), wherein soluble resol polymer is used as an organic precursor; TEOS is used as an inorganic precursor, and triblock copolymer F127 is used as a template. The application of MP-C-type OMCs supported Pt nanoparticles in heterogeneous asymmetric hydrogenation ofα-functionalized ketones has been rarely reported up to now.
In the first part,4% and 10%(mass fraction) Pt catalysts supported on MP-C-61 were prepared by an impregnation method using two different Pt precursors, ethanolic solution and aqueous solution of H2PtCl6.These Pt/MP-C-61 catalysts were characterized by XRD, N2-sorption, TEM and CO chemisorption. The Pt/MP-C-61 catalysts can be effectively applied in the asymmetric hydrogenation of ethyl pyruvate after chirally modified with cinchonidine. The Cat-4Pt-E catalyst derived from the ethanolic solution of H2PtCl6 afforded better conversions of ethyl pyruvate due to smaller Pt particle size with higher Pt dispersion. While the Cat-4Pt-W catalysts derived from the aqueous solution of H2PtCl6 showed higher chiral induction ability. The catalyst Cat-4Pt-W-150 that was calcined at 150℃under vacuum gave higher conversion and higher enantioselectivity than Cat-4Pt-W did, the highest TOF reaching 8820 h-1 in water. A 66% e.e. value was furnished by Cat-lOPt-E catalyst in acetic acid. In particular, the Cat-4Pt-W catalyst showed superior catalytic activity to the 5% mass fraction of commercial Pt/C catalyst, mainly due to the ordered mesoporous structure feature of MP-C-61 support. Moreover, Cat-4Pt-W can be recycled easily for more than 10 times without distinct loss activity or enantioselectivity in the water. The 4% Pt catalysts supported on MP-C-61 can also be effectively applied in the asymmetric hydrogenation of ethyl 2-oxo-4-phenylbutyrate, of which the hydrogenation product can be used to produce A.C.E inhibitors. Under the optimal conditions, the catalyst Cat-4Pt-W-150 gave a 61% e.e. value of (R)-(+)-ethyl 2-hydroxyl-4-phenylbutyrate in acetic acid.
In recent years, Pt/Al2O3 has also been successfully applied to the heterogeneous enantioselective hydrogenation of a-functionalized ketones. It is a target to prepare ordered mesoporous alumina with high surface area, ordered pore channel and high thermal stability due toγ-Al2O3 has lower surface area and wide Pore-size distribution. Simple sol-gel route is a high-throughput method to synthesize MA as reported in the literature.
In the second part, we prepared the highly ordered Pt-containing mesoporous alumina catalyst by one-pot synthesis and investigated the catalytic performance in the heterogeneous enantioselective hydrogenation of ethyl pyruvate after modifying the catalysts with cinchonidine. Among all the xPt/MA catalysts prepared by the one-pot method with different Pt loadings and ever calcined in different atomsphere, 3Pt/MA(E)-A, which possessed 3 wt.% Pt loading and was calcined in air before reduction, maintained the mesoporous structure well and had high dispersion of Pt particles, so it showed the best catalytic performance, as a result,83.5% conversion of ethyl pyruvate was obtained with 74.4% e.e. value of (R)-(+)-ethyl lactate, which is even better than 5Pt/MA prepared via an impregnation method.
引文
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