负载型铑催化剂的制备、表征及烯烃氢甲酰化反应研究
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摘要
烯烃氢甲酰化是用于合成有机含氧化合物的重要工业过程。低碳烯烃氢甲酰化普遍使用均相催化剂,并多用有机物或水作反应溶剂。对于高碳烯烃氢甲酰化反应,由于烯烃在水中的溶解度极低,从而限制了水/有机两相催化的应用;又由于高碳醛沸点较高,铑催化剂回收过程易引起失活。目前,高碳烯烃氢甲酰化反应工艺主要采用高压钴法,存在催化剂回收过程复杂,副反应多和能耗高等缺点。为了解决这些问题,近年来人们对高碳烯烃氢甲酰化均相催化多相化技术进行了大量研究,但仍存在着催化剂活性低、活性组分流失严重等技术难题。因此,开发新型负载型催化剂对于高碳烯烃氢甲酰化反应具有重要的理论和实际意义。
混合辛烯(主要含有2,4,4-三甲基-1-戊烯和2,4,4-三甲基-2-戊烯)氢甲酰化合成产物异壬醛具有重要的工业应用价值。本文首先根据2,4,4-三甲基-1-戊烯、2,4,4-三甲基-2-戊烯和异壬醛的分子结构特点以及有机合成理论,利用Benson和Constantinou-Gani基团贡献法对缺少的热力学数据进行了估算,对混合辛烯氢甲酰化反应体系进行了热力学分析。计算表明,异辛烯氢甲酰化是强放热反应且平衡常数很大,反应主要受动力学因素控制。
本文以活性炭为载体,以三氯化铑为催化剂前体,采用等体积浸渍法制备了无机磷酸改性的负载型铑催化剂Rh-P/AC。通过活性炭载体的N2吸附、Boehm滴定和FT-IR测定等表征手段,详细考察了载体类型、预处理和催化剂制备条件对Rh-P/AC催化性能的影响。结果表明,载体表面性质对催化剂性能影响很大,活性炭碱热活化处理较酸处理和碱洗处理更有利于催化剂活性的提高。碱热预处理后,活性炭载体的介孔比例和表面羟基、羰基以及碱性基团增加。通过正交实验对载体预处理和催化剂制备条件进行了优化,考察了各因素的影响程度。结果表明,以煤基颗粒为载体,碱热预处理的最优条件为:碱/炭质量比为1.0,活化终点温度790?C,活化时间75min,pH值9.0;催化剂制备最优条件为:Rh负载量为0.8%,磷酸负载量为5.0%,浸渍温度为45?C;在最优预处理条件下,异壬醛收率可达到50.5%,选择性接近100%。
对混合辛烯氢甲酰化反应条件研究表明,Rh-P/AC催化剂在107?C、5.0MPa条件下具有高的催化活性和成醛选择性,反应5.0h的平均TOF(转换频率)为539.4h-1,有效解决了均相催化剂分离困难和多相催化剂活性低的问题。Rh-P/AC催化剂连续使用4次铑流失量很小,稳定性好。当以甲苯作反应溶剂时,Rh-P/AC催化剂的氢甲酰化活性可进一步提高。
用低温N2吸附、FT-IR、XPS和XRD等技术对载体以及催化剂进行了表征。结果表明,活性炭负载RhCl3后,载体微孔表面积和微孔孔容基本不变,比表面积和总孔容降低,活性组分基本分布于介孔和大孔表面上。对催化剂制备过程中活性炭表面基团变化的分析表明,表面-OH、-C=O和碱性基团可以通过偶极-偶极(π-d)相互作用和氧化还原作用对铑进行锚定,有C-O-Rh配位键形成,并有Rh2O3和Rh?存在。磷酸改性在载体表面形成的磷酸物种与铑之间存在配位作用。XRD物相分析表明,铑物种高度分散在载体上。
助剂研究表明,碱金属和部分过渡金属(包括V、Zn、Zr、Cu、Pt、Mo和Co)的加入可以提高Rh-P/AC催化剂的氢甲酰化活性和选择性,其中以KOH和V复合改性对催化剂的促进效果最好。浸渍顺序对催化剂活性影响较大,先浸渍助剂后浸渍RhCl3的催化剂活性较好。对钒负载量的研究表明,钒的质量分数为1.0%时催化剂活性最好。XRD和XPS分析表明,钒物种的加入能够改善催化剂上活性组分的分散度,同时提高Rh3d的结合能,并抑制金属铑的形成。
在间歇高压釜中考察了Rh-P/AC催化混合辛烯氢甲酰化反应动力学。在消除内外扩散影响的条件下,通过测定氢甲酰化过程中烯烃浓度随时间的变化关系,获取了混合辛烯氢甲酰化的反应速率参数。按照Langmuir-Hinshelwood机理建立了2,4,4-三甲基-1-戊烯氢甲酰化的本征动力学机理模型,并由本征动力学数据通过数学方法估算了模型参数,证实了以催化剂上产物醛脱附为控制步骤的反应速率方程LHHW IV可以较好的描述实验结果。动力学结果为混合辛烯氢甲酰化合成异壬醛的过程放大提供了理论依据。
The hydroformylation of alkenes is a major commercial process used for the production of oxygenated organic compounds. The homogeneous catalyst and organic or aqueous solvents are commonly employed for the hydroformylation of light alkenes. However, the hydroformylation of long-chain olefins in aqueous-organic system is noneffective due to the low-solubility of long-chain olefins in water. Moreover, the homogeneous hydroformylation meets the deactivation of rhodium catalysts at high temperature distillation in separation process of catalysts. Up to now, most of the hydroformylation of long-chain olefins applied the high-pressure-cobalt technique, but it has some disadvantages, such as complicated process of catalyst recycle, a great number of byproducts, high energy consumption and so on. In order to solve these problems, the heterogenization of homogeneous catalysis for hydroformylation of high olefins has been studied in recent years, but there still have been some disadvantages, such as low activity and high loss of catalysts. So, it is great significant to develop new supported catalysts.
The production of isononyl-aldehydes from mixed octenes (2,4,4-trimethyl-1-pentene and 2,4,4- trimethyl-2-pentene) by hydroformylation is of important industrial application. Firstly, thermodynamic analysis were done, and Benson and Constantinou-Gani groups contribution methods were used to calculate the absent thermodynamic data, on the basis of molecular structure of 2,4,4-trimethyl-1-pentene, 2,4,4-trimethyl-2-pentene, isononyl- aldehydes and the organic synthetic principle. It was found that the hydroformylation of isooctene was strongly exothermic reaction and its equilibrium constant was very large under reaction conditions, therefore, the reaction was governed by kinetic process.
The supported rhodium catalysts modified with phosphoric acid were prepared by incipient impregnation using activated carbon as support and rhodium trichloride trihydrate as precursor. N2 adsorption, Boehm titration and FT-IR spectra were used to investigate the influence of support, pretreatment and catalyst preparation conditions on catalyst performance. The results showed that the surface properties of support had great influence on catalyst. The alkali-heat-treatment of activated carbon was beneficial to improve catalytic performance, and was better than acid treatment and alkali washing treatment. Furthermore, the basic groups such as hydroxyl and carbonyl on activated carbon surface, as well as distribution of mesopores both got increased after alkali-heat-treatment. Orthogonal experiment was designed to optimize the process of support pretreatment and catalyst preparation. The optimized pretreatment conditions were alkali/carbon mass ratio of 1.0, activation temperature of 790?C, activation time of 75 min and pH of 9.0. The optimized catalyst preparation conditions were rhodium loading of 0.8%, phosphoric acid loading 5.0% and impregnation temperature of 45?C. The yield of isononyl-aldehydes could be up to 50.5% and the selectivity approach to 100% under the optimized conditions.
The effects of reaction conditions on the hydroformylation of mixed octenes over Rh-P/AC were studied. The results showed that Rh-P/AC catalyst exhibited a high activity and selectivity to aldehydes. The average TOF (turnover frequency) within 5.0 h for the hydroformylation of mixed octenes over Rh-P/AC catalyst was up to 539.4 h-1. The problems of recycle and low activity of some other catalysts were well solved in this system. It was found that Rh-P/AC can be recycled 4 times without significant loss of rhodium, demonstrating that catalyst had high stability. Also, the catalytic activity of Rh-P/AC could be increased when toluene was used as reaction solvent.
From the characterization of N2 adsorption, FT-IR, XPS and XRD, it was found that micropore surface area and pore volume of the activated carbon were nearly unchanged after loading with RhCl3. However, the total surface area and pore volume decreased, indicated that the active component dispersed on the external surface of mesopores and macropores. Simultaneously, it was observed that the -OH, -C=O and basic groups acted as the adsorption center to bond metal species by dipole-dipole (π-d) interaction and redox reaction mechanism. After loading, the rhodium species exists in Rh2O3, Rh? and C-O-Rh complexes. There was the coordination interaction between Rh species and phosphoric acid species in the phosphoric acid modified catalysts. The XRD results showed that rhodium species dispersed monolayer on support.
The experimental results revealed that alkali metals and some transition metals (including V, Zn, Zr, Cu, Pt, Mo and Co) could promote hydroformylation activity and selectivity of the Rh-P/AC catalysts. Among them, the combination of KOH and V exhibited the best promoting effect. The impregnation sequence had also influence the activity of the catalyst for hydroformylation. The catalyst impregnated RhCl3 after impregnation of promoters had the higher activity. The optimal loading amount of V species was 1.0% (mass fraction). The results of XRD and XPS indicated that V species increased the dispersity of Rh species and the binding energy of Rh3d on the support, as well as inhibited the formation of Rh? species.
Hydroformylation reaction kinetics of mixed octenes on Rh-P/AC catalyst was studied in a high-pressure batch reactor under conditions free from the influence of external and internal diffusions. And the kinetics parameters were determined by fitting the changes of octenes concentrations with time. Based on the Langmuir-Hinshelwood mechanism, the intrinsic kinetic models were established, and model parameters were fitted by using mathematical method. It can be confirmed that kinetic model LHHW IV with desorption of aldehydes from catalyst as rate-control step could depict the experimental data well. The kinetic model may provide a reference for the scaling-up of isononyl-aldehydes synthesis from hydroformylation of mixed octenes.
混合辛烯(主要含有2,4,4-三甲基-1-戊烯和2,4,4-三甲基-2-戊烯)氢甲酰化合成产物异壬醛具有重要的工业应用价值。本文首先根据2,4,4-三甲基-1-戊烯、2,4,4-三甲基-2-戊烯和异壬醛的分子结构特点以及有机合成理论,利用Benson和Constantinou-Gani基团贡献法对缺少的热力学数据进行了估算,对混合辛烯氢甲酰化反应体系进行了热力学分析。计算表明,异辛烯氢甲酰化是强放热反应且平衡常数很大,反应主要受动力学因素控制。
本文以活性炭为载体,以三氯化铑为催化剂前体,采用等体积浸渍法制备了无机磷酸改性的负载型铑催化剂Rh-P/AC。通过活性炭载体的N2吸附、Boehm滴定和FT-IR测定等表征手段,详细考察了载体类型、预处理和催化剂制备条件对Rh-P/AC催化性能的影响。结果表明,载体表面性质对催化剂性能影响很大,活性炭碱热活化处理较酸处理和碱洗处理更有利于催化剂活性的提高。碱热预处理后,活性炭载体的介孔比例和表面羟基、羰基以及碱性基团增加。通过正交实验对载体预处理和催化剂制备条件进行了优化,考察了各因素的影响程度。结果表明,以煤基颗粒为载体,碱热预处理的最优条件为:碱/炭质量比为1.0,活化终点温度790?C,活化时间75min,pH值9.0;催化剂制备最优条件为:Rh负载量为0.8%,磷酸负载量为5.0%,浸渍温度为45?C;在最优预处理条件下,异壬醛收率可达到50.5%,选择性接近100%。
对混合辛烯氢甲酰化反应条件研究表明,Rh-P/AC催化剂在107?C、5.0MPa条件下具有高的催化活性和成醛选择性,反应5.0h的平均TOF(转换频率)为539.4h-1,有效解决了均相催化剂分离困难和多相催化剂活性低的问题。Rh-P/AC催化剂连续使用4次铑流失量很小,稳定性好。当以甲苯作反应溶剂时,Rh-P/AC催化剂的氢甲酰化活性可进一步提高。
用低温N2吸附、FT-IR、XPS和XRD等技术对载体以及催化剂进行了表征。结果表明,活性炭负载RhCl3后,载体微孔表面积和微孔孔容基本不变,比表面积和总孔容降低,活性组分基本分布于介孔和大孔表面上。对催化剂制备过程中活性炭表面基团变化的分析表明,表面-OH、-C=O和碱性基团可以通过偶极-偶极(π-d)相互作用和氧化还原作用对铑进行锚定,有C-O-Rh配位键形成,并有Rh2O3和Rh?存在。磷酸改性在载体表面形成的磷酸物种与铑之间存在配位作用。XRD物相分析表明,铑物种高度分散在载体上。
助剂研究表明,碱金属和部分过渡金属(包括V、Zn、Zr、Cu、Pt、Mo和Co)的加入可以提高Rh-P/AC催化剂的氢甲酰化活性和选择性,其中以KOH和V复合改性对催化剂的促进效果最好。浸渍顺序对催化剂活性影响较大,先浸渍助剂后浸渍RhCl3的催化剂活性较好。对钒负载量的研究表明,钒的质量分数为1.0%时催化剂活性最好。XRD和XPS分析表明,钒物种的加入能够改善催化剂上活性组分的分散度,同时提高Rh3d的结合能,并抑制金属铑的形成。
在间歇高压釜中考察了Rh-P/AC催化混合辛烯氢甲酰化反应动力学。在消除内外扩散影响的条件下,通过测定氢甲酰化过程中烯烃浓度随时间的变化关系,获取了混合辛烯氢甲酰化的反应速率参数。按照Langmuir-Hinshelwood机理建立了2,4,4-三甲基-1-戊烯氢甲酰化的本征动力学机理模型,并由本征动力学数据通过数学方法估算了模型参数,证实了以催化剂上产物醛脱附为控制步骤的反应速率方程LHHW IV可以较好的描述实验结果。动力学结果为混合辛烯氢甲酰化合成异壬醛的过程放大提供了理论依据。
The hydroformylation of alkenes is a major commercial process used for the production of oxygenated organic compounds. The homogeneous catalyst and organic or aqueous solvents are commonly employed for the hydroformylation of light alkenes. However, the hydroformylation of long-chain olefins in aqueous-organic system is noneffective due to the low-solubility of long-chain olefins in water. Moreover, the homogeneous hydroformylation meets the deactivation of rhodium catalysts at high temperature distillation in separation process of catalysts. Up to now, most of the hydroformylation of long-chain olefins applied the high-pressure-cobalt technique, but it has some disadvantages, such as complicated process of catalyst recycle, a great number of byproducts, high energy consumption and so on. In order to solve these problems, the heterogenization of homogeneous catalysis for hydroformylation of high olefins has been studied in recent years, but there still have been some disadvantages, such as low activity and high loss of catalysts. So, it is great significant to develop new supported catalysts.
The production of isononyl-aldehydes from mixed octenes (2,4,4-trimethyl-1-pentene and 2,4,4- trimethyl-2-pentene) by hydroformylation is of important industrial application. Firstly, thermodynamic analysis were done, and Benson and Constantinou-Gani groups contribution methods were used to calculate the absent thermodynamic data, on the basis of molecular structure of 2,4,4-trimethyl-1-pentene, 2,4,4-trimethyl-2-pentene, isononyl- aldehydes and the organic synthetic principle. It was found that the hydroformylation of isooctene was strongly exothermic reaction and its equilibrium constant was very large under reaction conditions, therefore, the reaction was governed by kinetic process.
The supported rhodium catalysts modified with phosphoric acid were prepared by incipient impregnation using activated carbon as support and rhodium trichloride trihydrate as precursor. N2 adsorption, Boehm titration and FT-IR spectra were used to investigate the influence of support, pretreatment and catalyst preparation conditions on catalyst performance. The results showed that the surface properties of support had great influence on catalyst. The alkali-heat-treatment of activated carbon was beneficial to improve catalytic performance, and was better than acid treatment and alkali washing treatment. Furthermore, the basic groups such as hydroxyl and carbonyl on activated carbon surface, as well as distribution of mesopores both got increased after alkali-heat-treatment. Orthogonal experiment was designed to optimize the process of support pretreatment and catalyst preparation. The optimized pretreatment conditions were alkali/carbon mass ratio of 1.0, activation temperature of 790?C, activation time of 75 min and pH of 9.0. The optimized catalyst preparation conditions were rhodium loading of 0.8%, phosphoric acid loading 5.0% and impregnation temperature of 45?C. The yield of isononyl-aldehydes could be up to 50.5% and the selectivity approach to 100% under the optimized conditions.
The effects of reaction conditions on the hydroformylation of mixed octenes over Rh-P/AC were studied. The results showed that Rh-P/AC catalyst exhibited a high activity and selectivity to aldehydes. The average TOF (turnover frequency) within 5.0 h for the hydroformylation of mixed octenes over Rh-P/AC catalyst was up to 539.4 h-1. The problems of recycle and low activity of some other catalysts were well solved in this system. It was found that Rh-P/AC can be recycled 4 times without significant loss of rhodium, demonstrating that catalyst had high stability. Also, the catalytic activity of Rh-P/AC could be increased when toluene was used as reaction solvent.
From the characterization of N2 adsorption, FT-IR, XPS and XRD, it was found that micropore surface area and pore volume of the activated carbon were nearly unchanged after loading with RhCl3. However, the total surface area and pore volume decreased, indicated that the active component dispersed on the external surface of mesopores and macropores. Simultaneously, it was observed that the -OH, -C=O and basic groups acted as the adsorption center to bond metal species by dipole-dipole (π-d) interaction and redox reaction mechanism. After loading, the rhodium species exists in Rh2O3, Rh? and C-O-Rh complexes. There was the coordination interaction between Rh species and phosphoric acid species in the phosphoric acid modified catalysts. The XRD results showed that rhodium species dispersed monolayer on support.
The experimental results revealed that alkali metals and some transition metals (including V, Zn, Zr, Cu, Pt, Mo and Co) could promote hydroformylation activity and selectivity of the Rh-P/AC catalysts. Among them, the combination of KOH and V exhibited the best promoting effect. The impregnation sequence had also influence the activity of the catalyst for hydroformylation. The catalyst impregnated RhCl3 after impregnation of promoters had the higher activity. The optimal loading amount of V species was 1.0% (mass fraction). The results of XRD and XPS indicated that V species increased the dispersity of Rh species and the binding energy of Rh3d on the support, as well as inhibited the formation of Rh? species.
Hydroformylation reaction kinetics of mixed octenes on Rh-P/AC catalyst was studied in a high-pressure batch reactor under conditions free from the influence of external and internal diffusions. And the kinetics parameters were determined by fitting the changes of octenes concentrations with time. Based on the Langmuir-Hinshelwood mechanism, the intrinsic kinetic models were established, and model parameters were fitted by using mathematical method. It can be confirmed that kinetic model LHHW IV with desorption of aldehydes from catalyst as rate-control step could depict the experimental data well. The kinetic model may provide a reference for the scaling-up of isononyl-aldehydes synthesis from hydroformylation of mixed octenes.
引文
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