铂—酸性离子液体双功能催化剂及催化合成对氨基苯酚研究
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摘要
对氨基苯酚( PAP)是一种重要有机合成中间体,被广泛应用于医药、染料、橡胶、照相等领域。本文针对以硝基苯为原料催化加氢合成对氨基苯酚工艺中存在的使用硫酸溶液等问题,通过设计由金属铂和酸性离子液体构成的新型催化剂,开发出了环境友好的合成对氨基苯酚新工艺。
采用两步法合成了一种新型季铵型Brφnsted酸性离子液体N,N,N-三甲基-N-磺丁基硫酸氢铵([HSO_3-b-N(CH_3)_3]HSO_4),通过FTIR、NMR、ESI-MS及元素分析等方法确定了该离子液体的结构,并发现其对苯基羟胺重排反应具有良好的催化活性;在此基础上,利用溶胶-凝胶法制备出了固载化的离子液体催化剂[HSO_3-b-N(CH_3)_3]HSO_4-SiO_2,在适宜反应条件下,苯基羟胺转化率为100%,对氨基苯酚选择性为60.5%。
设计并制备了由负载型铂催化剂(加氢活性位)和酸性离子液体(重排活性位)构成的新型高效双功能固-液相催化剂体系Pt/SiO_2+[HSO_3-b-N(CH_3)_3]HSO_4;研究了Pt/SiO_2催化剂用量、离子液体浓度、反应介质、助剂及反应条件等对其催化硝基苯加氢合成对氨基苯酚反应性能的影响规律。确定了铂催化剂用量与离子液体浓度的最佳匹配值:Pt/SiO_2用量5wt%,离子液体浓度为22.5wt%;在优化条件下,硝基苯转化率为96.6%,对氨基苯酚选择性为81.4%,高于硫酸体系;离子液体特有的季胺盐性质增加了硝基苯的溶解度,进而提高了反应性能;对反应后回收的离子液体结构进行了表征,证明其具有良好的稳定性。回收后的Pt/SiO_2催化剂和酸性离子液体构成的催化体系循环使用三次,活性无明显下降。
采用酸性离子液体[HSO_3-b-N(CH_3)_3]HSO_4,建立了同时获得均匀分散的Pt纳米粒子和具有金属和酸活性中心双功能催化剂的新方法;并采用TEM、UV-Vis、FTIR、XPS、XRD等对其结构进行了表征。所制备的Pt纳米粒子均匀分散在离子液体中,粒径约为3nm,具有面心立方相结构,并可长期(4个月以上)保持稳定分散状态。
采用直接法制备出了由铂纳米粒子和酸性离子液体构成的Pt-[HSO_3-b-N(CH_3)_3]HSO_4拟均相双功能催化剂;考察了醇/水比、回流时间及不同醇类等制备条件,以及铂纳米粒子含量、离子液体浓度、温度、氢分压等反应条件对硝基苯加氢合成对氨基苯酚反应性能的影响。优化确定了适宜的制备条件和反应条件,硝基苯转化率为99.3%,对氨基苯酚收率为77.5%;发现该酸性离子液体不仅起到酸催化剂的作用,而且还作为保护剂、稳定剂、分散剂能有效阻止Pt纳米粒子的团聚。
采用溶胶-凝胶法、浸渍法及化学键合法对铂-离子液体催化剂的固定化进行了研究,制备了Pt-离子液体/SiO_2固载型双功能催化剂。
利用溶胶-凝胶法将离子液体包埋在硅胶中,得到Pt-[HSO_3-b-N(CH_3)_3]HSO_4/SiO_2双功能催化剂,考察了铂固载量、制备温度、乙醇用量及凝胶老化时间等制备条件对催化反应性能的影响,在优化条件下,硝基苯转化率为66.7%,对氨基苯酚收率28.8%。
针对铂和离子液体的负载过程,分别利用顺序浸渍法和同时浸渍法制备了Pt-[HSO_3-bmim]HSO_4/SiO_2双功能催化剂。考察了负载量、干燥方式、还原方法等制备条件等对催化反应性能的影响。优化条件下,硝基苯转化率为68.6%,对氨基苯酚收率为41.4%。
合成并表征了一种新型Brφnsted酸性离子液体1-乙烯基-3-磺丁基咪唑硫酸氢盐([HSO_3-bvim]HSO_4),并通过自由基链转移反应将该酸性离子液体用化学键固定于氢硫基官能团化的硅胶表面,制备出了[HSO_3-bvim]HSO_4/SiO_2固体酸催化剂,再利用化学还原方法在该固体酸催化剂上负载金属铂,得到Pt-[HSO_3-bvim]HSO_4/SiO_2双功能催化剂。该双功能催化剂的反应性能较低,主要原因是键合在硅胶表面的离子液体数量较少和空间位阻作用造成的。但由于化学键合作用,使其稳定性明显高于溶胶-凝胶法和浸渍法制备的催化剂。
p-Aminophenol (PAP) is an important intermediate for organic synthesis and is widely used for the production of medicine, dyestuff, rubber and photographic chemicals, etc.. In this study, to settle the problems, such as the use of sulfuric acid, in the production of PAP through catalytic hydrogenation of nitrobenzene, a novel catalyst system, composed of metallic Pt and acidic ionic liquid, was designed and prepared to develop the environmentally benign technology for PAP synthesis.
A novel quaternary ammonium type of Brφnsted acidic ionic liquid, N,N,N-trimethyl-N- sulfobutyl hydrogen sulfate ([HSO_3-b-N(CH_3)_3]HSO_4), was synthesized through a two-step method. FTIR, NMR, ESI-MS and elementary analysis were used to characterize its structure. The ionic liquid showed a high catalytic activity for the rearrangement of phenylhydroxylamine. A supported ionic liquid catalyst, [HSO_3-b-N(CH_3)_3]HSO_4-SiO_2, was prepared using sol-gel method. Under the optimized conditions, the phenylhydroxylamine conversion and PAP selectivity over the supported catalyst were 100% and 60.5%, respectively.
A novel highly efficient bifunctional catalyst system, Pt/SiO_2+[HSO_3-b-N(CH_3)_3]HSO_4, composed of hydrogenation sites in solid state and rearrangement active sites in liquid state was designed and prepared for the nitrobenzene hydrogenation to PAP. The effects of the amount of Pt/SiO_2 catalyst, ionic liquid concentration, reaction medium, promoter, and reaction conditions on the nitrobenzene hydrogenation were investigated. The best amount of Pt/SiO_2 catalyst and suitable ionic liquid concentration were determined, and were 5wt% and 22.5wt%, respectively. Under the suitable conditions, the nitrobenzene conversion and PAP selectivity over the bifunctional catalyst were 96.6% and 81.4%, respectively. The catalytic activity was higher than that of sulfuric acid system, which was attributed to the solubility enhancement of nitrobenzene due to the nature of quaternary ammonium type of acidic ionic liquid. The structure of the recovered ionic liquid showed a good stability, and the catalytic activity of the bifunctional catalytic system was no obvious deactivation after recycled 3 times.
Using the acidic ionic liquid [HSO_3-b-N(CH_3)_3]HSO_4,a novel method for simultaneously preparing of the uniformly dispersed Pt nanoparticles without using polymer as protecting agent, and a novel bifunctional catalyst with metallic and acidic active sites was developed. TEM, UV-Vis, FTIR, XPS, and XRD were used to characterize its structure. The Pt nanoparticles had a face-centered cubic structure with diameters about 3nm, and could be maintained in good dispersed state for more than 4 months.
The pseudo homogenous bifunctional catalyst Pt-[HSO_3-b-N(CH_3)_3]HSO_4 was prepared by direct method. The effects of the preparation conditions, such as alcohol/H_2O ratio, reflux time and different alcohol, and the reaction conditions, including content of Pt nanoparticles, ionic liquid concentration, temperature, and H_2 pressure, on the nitrobenzene hydrogenation to PAP were investigated. Under the suitable conditions, the nitrobenzene conversion was 99.3%, and the PAP yield was 77.5%. In addition, it was found that the ionic liquid served not only as the acidic catalyst, but also the stabilizing agent to inhibit the aggregation of Pt nanoparticles.
The immobilization of Pt-ionic liquid catalyst was studied through sol-gel, impregnation and chemically bonded method.
The bifunctional catalyst, Pt-[HSO_3-b-N(CH_3)_3]HSO_4/SiO_2, was obtained by embedding ionic liquid into silica particles though sol-gel method. The effects of amount of Pt, preparation temperature, ethanol amount and aging time on the catalyst performance for nitrobenzene hydrogenation to PAP were investigated. Under the optimized conditions, the nitrobenzene conversion and the PAP yield were 66.7% and 28.8%, respectively.
Pt-[HSO_3-bmim]HSO_4/SiO_2 bifunctional catalysts were prepared by successive impregnation and co-impregnation methods. The effects of loadings, dry, and reduction on its catalytic activity were investigated. Under the optimized conditions, the nitrobenzene conversion and the PAP yield were 68.6% and 41.4%, respectively.
A novel Br?nsted type of acidic ionic liquid 1-vinyl-3-sulfobutyl imidazolium hydrogen sulfate, [HSO_3-bvim]HSO_4, was synthesized, and immobilized on silica gel, functionalized by sulphydryl, via free radical chain transfer reaction to obtain [HSO_3-bvim]HSO_4/SiO_2 solid acid catalyst. Then metallic Pt was supported on it using chemical reduction method to obtain the bifunctional catalyst Pt-[HSO_3-bvim]HSO_4/SiO_2. The catalyst showed a relative lower activity for nitrobenzene hydrogenation to PAP due to the less amount of ionic liquid bonded on the silica and the space hindrance effect. However, with the chemical bond, catalytic stability of it was better than those of the catalysts prepared by sol-gel and impregnation methods.
采用两步法合成了一种新型季铵型Brφnsted酸性离子液体N,N,N-三甲基-N-磺丁基硫酸氢铵([HSO_3-b-N(CH_3)_3]HSO_4),通过FTIR、NMR、ESI-MS及元素分析等方法确定了该离子液体的结构,并发现其对苯基羟胺重排反应具有良好的催化活性;在此基础上,利用溶胶-凝胶法制备出了固载化的离子液体催化剂[HSO_3-b-N(CH_3)_3]HSO_4-SiO_2,在适宜反应条件下,苯基羟胺转化率为100%,对氨基苯酚选择性为60.5%。
设计并制备了由负载型铂催化剂(加氢活性位)和酸性离子液体(重排活性位)构成的新型高效双功能固-液相催化剂体系Pt/SiO_2+[HSO_3-b-N(CH_3)_3]HSO_4;研究了Pt/SiO_2催化剂用量、离子液体浓度、反应介质、助剂及反应条件等对其催化硝基苯加氢合成对氨基苯酚反应性能的影响规律。确定了铂催化剂用量与离子液体浓度的最佳匹配值:Pt/SiO_2用量5wt%,离子液体浓度为22.5wt%;在优化条件下,硝基苯转化率为96.6%,对氨基苯酚选择性为81.4%,高于硫酸体系;离子液体特有的季胺盐性质增加了硝基苯的溶解度,进而提高了反应性能;对反应后回收的离子液体结构进行了表征,证明其具有良好的稳定性。回收后的Pt/SiO_2催化剂和酸性离子液体构成的催化体系循环使用三次,活性无明显下降。
采用酸性离子液体[HSO_3-b-N(CH_3)_3]HSO_4,建立了同时获得均匀分散的Pt纳米粒子和具有金属和酸活性中心双功能催化剂的新方法;并采用TEM、UV-Vis、FTIR、XPS、XRD等对其结构进行了表征。所制备的Pt纳米粒子均匀分散在离子液体中,粒径约为3nm,具有面心立方相结构,并可长期(4个月以上)保持稳定分散状态。
采用直接法制备出了由铂纳米粒子和酸性离子液体构成的Pt-[HSO_3-b-N(CH_3)_3]HSO_4拟均相双功能催化剂;考察了醇/水比、回流时间及不同醇类等制备条件,以及铂纳米粒子含量、离子液体浓度、温度、氢分压等反应条件对硝基苯加氢合成对氨基苯酚反应性能的影响。优化确定了适宜的制备条件和反应条件,硝基苯转化率为99.3%,对氨基苯酚收率为77.5%;发现该酸性离子液体不仅起到酸催化剂的作用,而且还作为保护剂、稳定剂、分散剂能有效阻止Pt纳米粒子的团聚。
采用溶胶-凝胶法、浸渍法及化学键合法对铂-离子液体催化剂的固定化进行了研究,制备了Pt-离子液体/SiO_2固载型双功能催化剂。
利用溶胶-凝胶法将离子液体包埋在硅胶中,得到Pt-[HSO_3-b-N(CH_3)_3]HSO_4/SiO_2双功能催化剂,考察了铂固载量、制备温度、乙醇用量及凝胶老化时间等制备条件对催化反应性能的影响,在优化条件下,硝基苯转化率为66.7%,对氨基苯酚收率28.8%。
针对铂和离子液体的负载过程,分别利用顺序浸渍法和同时浸渍法制备了Pt-[HSO_3-bmim]HSO_4/SiO_2双功能催化剂。考察了负载量、干燥方式、还原方法等制备条件等对催化反应性能的影响。优化条件下,硝基苯转化率为68.6%,对氨基苯酚收率为41.4%。
合成并表征了一种新型Brφnsted酸性离子液体1-乙烯基-3-磺丁基咪唑硫酸氢盐([HSO_3-bvim]HSO_4),并通过自由基链转移反应将该酸性离子液体用化学键固定于氢硫基官能团化的硅胶表面,制备出了[HSO_3-bvim]HSO_4/SiO_2固体酸催化剂,再利用化学还原方法在该固体酸催化剂上负载金属铂,得到Pt-[HSO_3-bvim]HSO_4/SiO_2双功能催化剂。该双功能催化剂的反应性能较低,主要原因是键合在硅胶表面的离子液体数量较少和空间位阻作用造成的。但由于化学键合作用,使其稳定性明显高于溶胶-凝胶法和浸渍法制备的催化剂。
p-Aminophenol (PAP) is an important intermediate for organic synthesis and is widely used for the production of medicine, dyestuff, rubber and photographic chemicals, etc.. In this study, to settle the problems, such as the use of sulfuric acid, in the production of PAP through catalytic hydrogenation of nitrobenzene, a novel catalyst system, composed of metallic Pt and acidic ionic liquid, was designed and prepared to develop the environmentally benign technology for PAP synthesis.
A novel quaternary ammonium type of Brφnsted acidic ionic liquid, N,N,N-trimethyl-N- sulfobutyl hydrogen sulfate ([HSO_3-b-N(CH_3)_3]HSO_4), was synthesized through a two-step method. FTIR, NMR, ESI-MS and elementary analysis were used to characterize its structure. The ionic liquid showed a high catalytic activity for the rearrangement of phenylhydroxylamine. A supported ionic liquid catalyst, [HSO_3-b-N(CH_3)_3]HSO_4-SiO_2, was prepared using sol-gel method. Under the optimized conditions, the phenylhydroxylamine conversion and PAP selectivity over the supported catalyst were 100% and 60.5%, respectively.
A novel highly efficient bifunctional catalyst system, Pt/SiO_2+[HSO_3-b-N(CH_3)_3]HSO_4, composed of hydrogenation sites in solid state and rearrangement active sites in liquid state was designed and prepared for the nitrobenzene hydrogenation to PAP. The effects of the amount of Pt/SiO_2 catalyst, ionic liquid concentration, reaction medium, promoter, and reaction conditions on the nitrobenzene hydrogenation were investigated. The best amount of Pt/SiO_2 catalyst and suitable ionic liquid concentration were determined, and were 5wt% and 22.5wt%, respectively. Under the suitable conditions, the nitrobenzene conversion and PAP selectivity over the bifunctional catalyst were 96.6% and 81.4%, respectively. The catalytic activity was higher than that of sulfuric acid system, which was attributed to the solubility enhancement of nitrobenzene due to the nature of quaternary ammonium type of acidic ionic liquid. The structure of the recovered ionic liquid showed a good stability, and the catalytic activity of the bifunctional catalytic system was no obvious deactivation after recycled 3 times.
Using the acidic ionic liquid [HSO_3-b-N(CH_3)_3]HSO_4,a novel method for simultaneously preparing of the uniformly dispersed Pt nanoparticles without using polymer as protecting agent, and a novel bifunctional catalyst with metallic and acidic active sites was developed. TEM, UV-Vis, FTIR, XPS, and XRD were used to characterize its structure. The Pt nanoparticles had a face-centered cubic structure with diameters about 3nm, and could be maintained in good dispersed state for more than 4 months.
The pseudo homogenous bifunctional catalyst Pt-[HSO_3-b-N(CH_3)_3]HSO_4 was prepared by direct method. The effects of the preparation conditions, such as alcohol/H_2O ratio, reflux time and different alcohol, and the reaction conditions, including content of Pt nanoparticles, ionic liquid concentration, temperature, and H_2 pressure, on the nitrobenzene hydrogenation to PAP were investigated. Under the suitable conditions, the nitrobenzene conversion was 99.3%, and the PAP yield was 77.5%. In addition, it was found that the ionic liquid served not only as the acidic catalyst, but also the stabilizing agent to inhibit the aggregation of Pt nanoparticles.
The immobilization of Pt-ionic liquid catalyst was studied through sol-gel, impregnation and chemically bonded method.
The bifunctional catalyst, Pt-[HSO_3-b-N(CH_3)_3]HSO_4/SiO_2, was obtained by embedding ionic liquid into silica particles though sol-gel method. The effects of amount of Pt, preparation temperature, ethanol amount and aging time on the catalyst performance for nitrobenzene hydrogenation to PAP were investigated. Under the optimized conditions, the nitrobenzene conversion and the PAP yield were 66.7% and 28.8%, respectively.
Pt-[HSO_3-bmim]HSO_4/SiO_2 bifunctional catalysts were prepared by successive impregnation and co-impregnation methods. The effects of loadings, dry, and reduction on its catalytic activity were investigated. Under the optimized conditions, the nitrobenzene conversion and the PAP yield were 68.6% and 41.4%, respectively.
A novel Br?nsted type of acidic ionic liquid 1-vinyl-3-sulfobutyl imidazolium hydrogen sulfate, [HSO_3-bvim]HSO_4, was synthesized, and immobilized on silica gel, functionalized by sulphydryl, via free radical chain transfer reaction to obtain [HSO_3-bvim]HSO_4/SiO_2 solid acid catalyst. Then metallic Pt was supported on it using chemical reduction method to obtain the bifunctional catalyst Pt-[HSO_3-bvim]HSO_4/SiO_2. The catalyst showed a relative lower activity for nitrobenzene hydrogenation to PAP due to the less amount of ionic liquid bonded on the silica and the space hindrance effect. However, with the chemical bond, catalytic stability of it was better than those of the catalysts prepared by sol-gel and impregnation methods.
引文
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