高效低污染糠醛选择加氢催化剂的研究
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摘要
呋喃工业的重要产品——糠醛来源于生物质玉米芯、棉籽壳、甘蔗渣等可再生资源。由于在呋喃环上含有不饱和碳碳双键和侧链的羰基,糠醛的化学性质十分活泼,经催化加氢可制得众多的衍生物。糠醇和2-甲基呋喃是仅对糠醛的羰基进行选择加氢所获得的产品,主要采用加氢能力较弱的Cu系催化剂。目前,我国生产糠醇的催化剂是从国外进口的Cu-Cr催化剂,价格非常昂贵;生产2-甲基呋喃的催化剂为亚铬酸铜和Cu-Cr合金催化剂。这些催化剂均含有极毒的致癌物质Cr,既给操作人员带来了伤害,又造成了严重的环境污染。因此改善糠醛加氢生产技术的关键应是开发价廉、高效、低污染和无污染的环境友好催化剂,这对发展我国以农副产品等可再生资源为原料的精细化学品工业、推动绿色化学过程技术的发展意义重大。
本论文以研究低Cr和无Cr的负载型催化剂为目的,制备了低Cr的Cu-Cr/γ-Al_2O_3催化剂和无Cr的Cu-Ca/SiO_2催化剂,采用XRD、SEM、TEM、XPS和TPR等技术对催化剂结构进行了表征,并分别研究了两类催化剂糠醛选择性加氢的催化性能。
采用浸渍法制备出Cu-Cr/γ-Al_2O_3负载型催化剂,结构表征和糠醛选择加氢制2-甲基呋喃活性评价结果表明,Cr的加入形成了Cu和Cr之间的相互作用,使部分CuO转变成CuCrO_4,改善了Cu在载体中的分散状态。随着Cr含量的增加,Cu和Cr之间的相互作用更加紧密,深加氢能力增强,适宜的Cu/Cr摩尔比为12:5,其Cr含量为6%(wt%,按Cr_2O_3计),远低于工业亚铬酸铜催化剂的Cr含量(Cr_2O_3含量为45%)。在此基础上,加入Mg、Ca、Ba、Zn助剂调变Cu和Cr之间的相互作用,发现碱土金属Mg、Ca、Ba对CuCrO_4结构的破坏作用随助剂碱性的增强而加剧,加氢能力明显下降,不利于2-甲基呋喃的选择性生成。而Zn助剂对调变Cu和Cr之间的相互作用较为适宜,减缓了2-甲基呋喃的深度加氢,提高了2-甲基呋喃的选择性。对优选出的CuCr-Zn5催化剂进行100h的稳定性评价,糠醛的转化率保持在100%,2-甲基呋喃的选择性稳定在91.3%～92.2%之间,反应前后催化剂无明显的体相和表面结构变化,具有优良的结构稳定性和催化性能稳定性。
根据溶胶-凝胶法制备纳米催化材料的技术特点,以廉价的工业硅溶胶为硅源,利用絮凝剂对硅溶胶的凝胶化作用和对金属离子的沉积作用,制备了高分散的Cu-Ca/SiO_2负载型催化剂。研究结果表明,采用1.0 mol/l的Na_2CO_3溶液,控制pH值为中性,可以制得20～40 nm的超细SiO_2载体,同时可使活性组分以5 nm左右的CuO粒子的形式均匀分散于载体内,避免了后处理过程中活性组分的流失,催化剂具有良好的热稳定性。与浸渍法相比,溶胶-凝胶法制备的催化剂活性组分晶粒尺寸小,分散程度高,表面活性中心密度大,活性组分与载体和助剂间具有较强的相互作用。随着活性组分负载量的增加,活性组分晶粒变大,与载体和助剂间的相互作用增强,同时增加了催化剂的深加氢能力,助剂Ca的加入提高了催化剂的稳定性。当以糠醇为目的产物时,适宜的CuO负载量为15%,在反应温度120℃、H_2/醛摩尔比5～7、糠醛液空速0.36 h~(-1)的条件下,糠醇收率为98%以上。当以2-甲基呋喃为目的产物时,适宜的CuO负载量为20%,在反应温度220℃、H_2/醛摩尔比5～6、糠醛液空速0.4 h~(-1)的条件下,2-甲基呋喃收率为94%左右。
对优选出的Cu-Cr/γ-Al_2O_3催化剂和Cu-Ca/SiO_2催化剂进行单管放大实验。结果表明,Cu-Cr/γ-Al_2O_3催化剂表现出良好的稳定性,2-甲基呋喃的收率为90%以上,优于工业催化剂;而Cu-Ca/SiO_2催化剂经过1100 h糠醛加氢制2-甲基呋喃和500 h糠醛加氢制糠醇的连续运行,2-甲基呋喃和糠醇的收率分别在92%和98%以上。对使用后的催化剂进行结构表征,结果表明,吸附的糠醛和反应过程中生成的树脂类聚合物覆盖了催化剂的表面或堵塞了催化剂的孔道是导致催化剂失活的主要原因。Cu-Ca/SiO_2催化剂较弱的表面酸性和适宜的中孔结构使其催化性能和抗积炭能力均优于Cu-Cr/γ-Al_2O_3催化剂。
As an important product in the furan industry,furfural comes from renewable biomass resources such as corncob,cotton seed hulls and bagasse etc.Furfural is a very reactive molecule because of its unsaturated carbon-carbon double bonds in the furan ring and the carbonyl in the side chain,so a large number of derivatives can be obtained by catalytic hydrogenation.Furfuryl alcohol and 2-methyl furan are the products obtained by selective hydrogenation of the carbonyl over Cu-based catalysts which have appropriate hydrogenation capability.At present,the commercial catalysts for the furfuryl alcohol are Cu-Cr catalysts imported from abroad,which are very expensive.The catalysts for the 2-methyl furan are either copper chromite or Cu-Cr alloy.These catalysts not only bring harm to the operators, but also cause serious environmental pollution because they contain highly toxic carcinogen Cr.Therefore,to develop an environment friendly catalyst of low cost,high efficiency and pollution free for furfural hydrogenation has become an imminent task.This will play a significant role not only for the development of the fine chemical industry using the renewable resources such as agricultural products but also for the development of the green chemical process technology in China.
This thesis aims at study on the low-Cr and the Cr free supported catalysts.The low-Cr Cu-Cr/γ-Al_2O_3 catalyst and the Cr free Cu-Ca/SiO_2 catalyst were prepared.Their structure was characterized by XRD,SEM,TEM,XPS,TPR,etc.techniques.Their catalytic performance for the selective hydrogenation of furfural was investigated.
The supported Cu-Cr/γ-Al_2O_3 catalyst was prepared by impregnation method.The results of structural characterization and activity evaluation for the selective hydrogenation of furfural to 2-methyl furan showed that the interaction between Cu and Cr species was formed by adding Cr,which resulted in the transformation of some CuO into CuCrO_4 and improved the Cu dispersion state in the cartier.It was noticed that increasing the Cr content could lead to enhanced interaction between Cu and Cr species,and improved deep hydrogenation ability of the catalyst.An appropriate Cu / Cr molar ratio was 12/5 where the Cr content in the catalyst was only 6%(wt%of Cr_2O_3),which was much lower than the commercial copper chromite catalyst(Cr_2O_3 45%).Based on this result,the interaction between Cu and Cr species was modified by adding Mg,Ca,Ba or Zn promoters to the catalysts.It was found that while increasing the alkaline-earth metal promoters the destructive effects of alkaline-earth metal Mg,Ca,Ba on CuCrO_4 structure was enhanced and the capacity of the hydrogenation catalyst was therefore reduced,resulting in decreased formation of 2-methyl furan.However,Zn is a more favorable promoter for the modification of the interaction between Cu and Cr species.The deep hydrogenation of 2-methyl furan was slowed down and the formation of 2-methyl furan was increased when using the catalyst modified by Zn promoter.The 100 hours stability test results for the optimum CuCr-Zn5 catalyst showed that the conversion of furfural remained at 100%and the selectivity of 2-methyl furan was stable between 91.3%and 92.2%.There were no visible structural changes of the catalysts after the reactions.Therefore,the CuCr-Zn5 catalyst possessed excellent stability of the structure and the stability of catalytic performance.
According to the characteristics of sol-gel technique used for preparing the nano-particles catalyst,highly dispersed Cu-Ca/SiO_2 supported catalyst was prepared by the gelation of the flocculant for the commercial silica sol at a low price and its sedimentation for the metal ion.The research results indicated that the 20～40 nanometer ultrafine SiO_2 carrier can be prepared by using solution of 1.0 mol / 1 Na_2CO_3 and controlling pH at the neutrality. At the same time,the active component can be dispersed uniformly in the carrier in the form of 5 nanometer CuO particles,with no loss in the post-processing,to give the catalyst of good thermal stability.Compared with the impregnation method,the grain size of the active component was smaller and its dispersion degree was higher,the density of active site on surface was bigger,and the interaction between active component and the cartier or promoters was stronger for the catalyst prepared by the sol-gel method.The crystal grains of active component became larger,and the interaction between the active component and the carrier or promoters was enhanced,and the deep hydrogenation ability of the catalyst was increased with increasing the content of the active component.The stability of the catalyst was improved by adding Ca promoter in the catalysts.When furfuryl alcohol was the target product,the appropriate loading amount of CuO was 15%,and the yield of furfuryl alcohol could reach above 98%at the reaction temperature 120℃,the H_2/furfural molar ratio of 5-7 and liquid space velocity of furfural 0.36 h~(-1).When 2-methyl furan was the target product,the appropriate loading amount of CuO was 20%,and the yield of 2-methyl furan was about 94% at the reaction temperature 220℃,the H_2/furfural molar ratio 5-6 and liquid space velocity of furfural 0.4 h~(-1).
The scale-up experiments for the optimum Cu-Cr/γ-Al_2O_3 catalyst and the Cu-Ca/SiO_2 catalyst were carried out in the single-tube reactor.The results showed that the Cu-Cr/γ-Al_2O_3 catalyst displayed good stability.The yield of 2-methyl furan was above 90%,which was superior to one of the commercial catalysts.The yield of 2-methyl furan was above 92%for the Cu-Ca/SiO_2 catalyst after the continuous operations of 1100 hours for the hydrogenation of superior to one of the commercial catalysts.The yield of 2-methyl furan was above 92%for the Cu-Ca/SiO_2 catalyst after the continuous operations of 1100 hours for the hydrogenation of furfural..The yield of furfuryl alcohol was above 98%for the Cu-Ca/SiO_2 catalyst after the continuous operations of 500 hours for the hydrogenation of furfural.The structural characterization of the used catalysts indicated that the deactivation of the catalyst is mainly due to the fact that furfural absorbed on the surface of the catalyst and the resin like polymer generated in the reaction have covered the surface of the catalyst or blocked the pores of the catalyst.It is believed that Cu-Ca/SiO_2 has superior catalytic performance and the ability of resisting the composition of the coke compared with the Cu-Cr/γ-Al_2O_3 catalyst,mainly due to its weaker surface acidity and appropriate pore structure.
本论文以研究低Cr和无Cr的负载型催化剂为目的,制备了低Cr的Cu-Cr/γ-Al_2O_3催化剂和无Cr的Cu-Ca/SiO_2催化剂,采用XRD、SEM、TEM、XPS和TPR等技术对催化剂结构进行了表征,并分别研究了两类催化剂糠醛选择性加氢的催化性能。
采用浸渍法制备出Cu-Cr/γ-Al_2O_3负载型催化剂,结构表征和糠醛选择加氢制2-甲基呋喃活性评价结果表明,Cr的加入形成了Cu和Cr之间的相互作用,使部分CuO转变成CuCrO_4,改善了Cu在载体中的分散状态。随着Cr含量的增加,Cu和Cr之间的相互作用更加紧密,深加氢能力增强,适宜的Cu/Cr摩尔比为12:5,其Cr含量为6%(wt%,按Cr_2O_3计),远低于工业亚铬酸铜催化剂的Cr含量(Cr_2O_3含量为45%)。在此基础上,加入Mg、Ca、Ba、Zn助剂调变Cu和Cr之间的相互作用,发现碱土金属Mg、Ca、Ba对CuCrO_4结构的破坏作用随助剂碱性的增强而加剧,加氢能力明显下降,不利于2-甲基呋喃的选择性生成。而Zn助剂对调变Cu和Cr之间的相互作用较为适宜,减缓了2-甲基呋喃的深度加氢,提高了2-甲基呋喃的选择性。对优选出的CuCr-Zn5催化剂进行100h的稳定性评价,糠醛的转化率保持在100%,2-甲基呋喃的选择性稳定在91.3%～92.2%之间,反应前后催化剂无明显的体相和表面结构变化,具有优良的结构稳定性和催化性能稳定性。
根据溶胶-凝胶法制备纳米催化材料的技术特点,以廉价的工业硅溶胶为硅源,利用絮凝剂对硅溶胶的凝胶化作用和对金属离子的沉积作用,制备了高分散的Cu-Ca/SiO_2负载型催化剂。研究结果表明,采用1.0 mol/l的Na_2CO_3溶液,控制pH值为中性,可以制得20～40 nm的超细SiO_2载体,同时可使活性组分以5 nm左右的CuO粒子的形式均匀分散于载体内,避免了后处理过程中活性组分的流失,催化剂具有良好的热稳定性。与浸渍法相比,溶胶-凝胶法制备的催化剂活性组分晶粒尺寸小,分散程度高,表面活性中心密度大,活性组分与载体和助剂间具有较强的相互作用。随着活性组分负载量的增加,活性组分晶粒变大,与载体和助剂间的相互作用增强,同时增加了催化剂的深加氢能力,助剂Ca的加入提高了催化剂的稳定性。当以糠醇为目的产物时,适宜的CuO负载量为15%,在反应温度120℃、H_2/醛摩尔比5～7、糠醛液空速0.36 h~(-1)的条件下,糠醇收率为98%以上。当以2-甲基呋喃为目的产物时,适宜的CuO负载量为20%,在反应温度220℃、H_2/醛摩尔比5～6、糠醛液空速0.4 h~(-1)的条件下,2-甲基呋喃收率为94%左右。
对优选出的Cu-Cr/γ-Al_2O_3催化剂和Cu-Ca/SiO_2催化剂进行单管放大实验。结果表明,Cu-Cr/γ-Al_2O_3催化剂表现出良好的稳定性,2-甲基呋喃的收率为90%以上,优于工业催化剂;而Cu-Ca/SiO_2催化剂经过1100 h糠醛加氢制2-甲基呋喃和500 h糠醛加氢制糠醇的连续运行,2-甲基呋喃和糠醇的收率分别在92%和98%以上。对使用后的催化剂进行结构表征,结果表明,吸附的糠醛和反应过程中生成的树脂类聚合物覆盖了催化剂的表面或堵塞了催化剂的孔道是导致催化剂失活的主要原因。Cu-Ca/SiO_2催化剂较弱的表面酸性和适宜的中孔结构使其催化性能和抗积炭能力均优于Cu-Cr/γ-Al_2O_3催化剂。
As an important product in the furan industry,furfural comes from renewable biomass resources such as corncob,cotton seed hulls and bagasse etc.Furfural is a very reactive molecule because of its unsaturated carbon-carbon double bonds in the furan ring and the carbonyl in the side chain,so a large number of derivatives can be obtained by catalytic hydrogenation.Furfuryl alcohol and 2-methyl furan are the products obtained by selective hydrogenation of the carbonyl over Cu-based catalysts which have appropriate hydrogenation capability.At present,the commercial catalysts for the furfuryl alcohol are Cu-Cr catalysts imported from abroad,which are very expensive.The catalysts for the 2-methyl furan are either copper chromite or Cu-Cr alloy.These catalysts not only bring harm to the operators, but also cause serious environmental pollution because they contain highly toxic carcinogen Cr.Therefore,to develop an environment friendly catalyst of low cost,high efficiency and pollution free for furfural hydrogenation has become an imminent task.This will play a significant role not only for the development of the fine chemical industry using the renewable resources such as agricultural products but also for the development of the green chemical process technology in China.
This thesis aims at study on the low-Cr and the Cr free supported catalysts.The low-Cr Cu-Cr/γ-Al_2O_3 catalyst and the Cr free Cu-Ca/SiO_2 catalyst were prepared.Their structure was characterized by XRD,SEM,TEM,XPS,TPR,etc.techniques.Their catalytic performance for the selective hydrogenation of furfural was investigated.
The supported Cu-Cr/γ-Al_2O_3 catalyst was prepared by impregnation method.The results of structural characterization and activity evaluation for the selective hydrogenation of furfural to 2-methyl furan showed that the interaction between Cu and Cr species was formed by adding Cr,which resulted in the transformation of some CuO into CuCrO_4 and improved the Cu dispersion state in the cartier.It was noticed that increasing the Cr content could lead to enhanced interaction between Cu and Cr species,and improved deep hydrogenation ability of the catalyst.An appropriate Cu / Cr molar ratio was 12/5 where the Cr content in the catalyst was only 6%(wt%of Cr_2O_3),which was much lower than the commercial copper chromite catalyst(Cr_2O_3 45%).Based on this result,the interaction between Cu and Cr species was modified by adding Mg,Ca,Ba or Zn promoters to the catalysts.It was found that while increasing the alkaline-earth metal promoters the destructive effects of alkaline-earth metal Mg,Ca,Ba on CuCrO_4 structure was enhanced and the capacity of the hydrogenation catalyst was therefore reduced,resulting in decreased formation of 2-methyl furan.However,Zn is a more favorable promoter for the modification of the interaction between Cu and Cr species.The deep hydrogenation of 2-methyl furan was slowed down and the formation of 2-methyl furan was increased when using the catalyst modified by Zn promoter.The 100 hours stability test results for the optimum CuCr-Zn5 catalyst showed that the conversion of furfural remained at 100%and the selectivity of 2-methyl furan was stable between 91.3%and 92.2%.There were no visible structural changes of the catalysts after the reactions.Therefore,the CuCr-Zn5 catalyst possessed excellent stability of the structure and the stability of catalytic performance.
According to the characteristics of sol-gel technique used for preparing the nano-particles catalyst,highly dispersed Cu-Ca/SiO_2 supported catalyst was prepared by the gelation of the flocculant for the commercial silica sol at a low price and its sedimentation for the metal ion.The research results indicated that the 20～40 nanometer ultrafine SiO_2 carrier can be prepared by using solution of 1.0 mol / 1 Na_2CO_3 and controlling pH at the neutrality. At the same time,the active component can be dispersed uniformly in the carrier in the form of 5 nanometer CuO particles,with no loss in the post-processing,to give the catalyst of good thermal stability.Compared with the impregnation method,the grain size of the active component was smaller and its dispersion degree was higher,the density of active site on surface was bigger,and the interaction between active component and the cartier or promoters was stronger for the catalyst prepared by the sol-gel method.The crystal grains of active component became larger,and the interaction between the active component and the carrier or promoters was enhanced,and the deep hydrogenation ability of the catalyst was increased with increasing the content of the active component.The stability of the catalyst was improved by adding Ca promoter in the catalysts.When furfuryl alcohol was the target product,the appropriate loading amount of CuO was 15%,and the yield of furfuryl alcohol could reach above 98%at the reaction temperature 120℃,the H_2/furfural molar ratio of 5-7 and liquid space velocity of furfural 0.36 h~(-1).When 2-methyl furan was the target product,the appropriate loading amount of CuO was 20%,and the yield of 2-methyl furan was about 94% at the reaction temperature 220℃,the H_2/furfural molar ratio 5-6 and liquid space velocity of furfural 0.4 h~(-1).
The scale-up experiments for the optimum Cu-Cr/γ-Al_2O_3 catalyst and the Cu-Ca/SiO_2 catalyst were carried out in the single-tube reactor.The results showed that the Cu-Cr/γ-Al_2O_3 catalyst displayed good stability.The yield of 2-methyl furan was above 90%,which was superior to one of the commercial catalysts.The yield of 2-methyl furan was above 92%for the Cu-Ca/SiO_2 catalyst after the continuous operations of 1100 hours for the hydrogenation of superior to one of the commercial catalysts.The yield of 2-methyl furan was above 92%for the Cu-Ca/SiO_2 catalyst after the continuous operations of 1100 hours for the hydrogenation of furfural..The yield of furfuryl alcohol was above 98%for the Cu-Ca/SiO_2 catalyst after the continuous operations of 500 hours for the hydrogenation of furfural.The structural characterization of the used catalysts indicated that the deactivation of the catalyst is mainly due to the fact that furfural absorbed on the surface of the catalyst and the resin like polymer generated in the reaction have covered the surface of the catalyst or blocked the pores of the catalyst.It is believed that Cu-Ca/SiO_2 has superior catalytic performance and the ability of resisting the composition of the coke compared with the Cu-Cr/γ-Al_2O_3 catalyst,mainly due to its weaker surface acidity and appropriate pore structure.
引文
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