铑膦（Rh-P）催化剂的制备、固载化及其在丙烯制丁醛/辛烯醛中的应用
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摘要
众所周知,催化剂的研究和开发是现代化学工业的核心问题之一。目前工业上4套丁辛醇装置都存在高能耗、高污染等问题,在呼唤节能减排、绿色催化和绿色生产工艺的今天,该问题显得尤为突出。因此,开发出应用于丁辛醇装置的绿色环保催化工艺是一项有挑战性但又势在必行的研究。
本文首先采用一步法制备了铑膦配合物催化剂HRh(CO)(PPh_3)_3,考察了不同氢源对催化剂结构的影响。结果表明:以氢氧化钾为氢源能够高效的合成目标催化剂HRh(CO)(PPh_3)_3,铑的利用率为95%左右;以硼氢化钠为氢源,产物为trans-RhCl(CO)(PPh_3)_2和HRh(CO)(PPh_3)_3的混合物,甲醛的滴加速度对两种产物的组分有着重要的影响,随甲醛滴加速度的逐渐减慢,目标催化剂HRh(CO)(PPh_3)_3含量逐渐增多,trans-RhCl(CO)(PPh_3)_2的含量逐渐减少,铑的利用率为85%左右;常压下,以氢气作为氢源不能合成目标催化剂HRh(CO)(PPh_3)_3,产物为trans-RhCl(CO)(PPh_3)_2;
其次,利用丙烯加氢甲酰化反应对所制备催化剂HRh(CO)(PPh_3)_3的催化性能进行评价,并和工业上所用的催化剂ROPAC进行对比;考察了膦铑比、铑浓度、温度和一氧化碳分压等工艺条件对催化剂催化性能的影响。结果表明:该催化剂在丙烯加氢甲酰化反应中表现出较好的催化性能,在同等条件下其催化性能要优于工业上所用的ROPAC催化剂;其催化丙烯加氢甲酰化反应的较佳工艺条件为:温度为90℃,一氧化碳的分压为0.1 MPa,膦铑比为300,铑的浓度为300 ppm,该条件下2 h内丙烯的转化率为71.7%,产物的正异构比为8.10,平均反应速率为0.042 mol·L~(-1)·min~(-1),丙烯转化为丁醛的转化频率为864 h~(-1);
最后,本文通过在分子筛MCM-41表面嫁接有机胺官能团和锚定铑膦配合物催化剂HRh(CO)(PPh_3)_3制备双功能催化剂,考察了负载胺类型、氮和铑的负载量对催化剂催化性能的影响。结果显示:通过该法可以制得双功能催化剂MCM-41-NR1R2-Rh-P,制备过程中载体分子筛MCM-41的晶体结构未被破坏,但比表面积及孔道直径降低;该催化剂能够实现丙烯一锅法制备辛烯醛反应;两种活性组分的合适配比为氮(伯胺)的负载量为1.73%左右,铑的负载量为0.19%左右,该条件下6 h内辛烯醛的收率高达75.0%。
As we all know, study and development of catalyst are one of the core issues of the modern chemical industry. Nowadays, there are many problems in 4 sets of octanol devices in the current industry such as high energy consumption and high pollution, which is especially prominent in the days of calling energy conservation, green catalysis and green production processes. Therefore, it is a challenging but imperative research to develop a green catalytic process used in octanol devices.
First, a rhodium-phosphine complex catalyst HRh(CO)(PPh_3)_3 was prepared in one-step process. The effects of different hydrogen were investigated on the structure of catalyst. The results showed that with potassium hydroxide as a hydrogen source, HRh(CO)(PPh_3)_3 can be efficiently synthesized and the utilization ratio of Rh reached about 95%. While with sodium borohydride as a hydrogen source, the product was the mixture of trans-RhCl(CO)(PPh_3)_2 and HRh(CO)(PPh_3)_3. The dropping rate of formaldehyde had a significant impact on components of the two products. As the dropping rate of formaldehyde gradually slowed down, the concentration of HRh(CO)(PPh_3)_3 gradually increased, while the content of trans-RhCl(CO)(PPh_3)_2 gradually decreased, and the utilization rate of Rh was about 85%. Using hydrogen as a hydrogen source under atmospheric pressure, HRh(CO)(PPh_3)_3 can not be synthesized, and the product was trans-RhCl(CO)(PPh_3)_2.
Second, the activity of the as-prepared catalysts has been evaluated by hydroformylation of propylene, which was compared with ROPAC used as the industrial catalyst. The ratio of phosphine and rhodium, the concentration of rhodium, temperature and partial pressure of carbon monoxide had great impact on catalytic performance. As-synthesized HRh(CO)(PPh_3)_3 had better catalytic performances for the hydroformylation of propylene, which was better than ROPAC used as the industrial catalyst under the same conditions. The better conditions of HRh(CO)(PPh_3)_3 in catalyzing hydroformylation of propylene were that temperature was 90℃, the partial pressure of carbon monoxide was 0.1 MPa, the ratio of phosphine and rhodium was 300 and the concentration of rhodium was 300 ppm. Under these conditions, the conversion of propylene was 71.7% within 2h and the n/i of product was 8.10 while the average reaction rate was 0.042 mol·L~(-1)·min~(-1) and the conversion frequency of propylene to butyraldehyde was 864 h-1;
Last, the dual-function catalyst was prepared by grafting organoamine and rhodium-phosphine HRh(CO)(PPh_3)_3 on the MCM-41 surface. And the impact of types of amines, nitrogen amount and the amount of rhodium on the catalyst properties was investigated. The results were summarized as follows: dual-function catalyst MCM-41-NH_2-Rh-P was obtained by grafting method, and the crystal structure of MCM-41 had not been destroyed, but the surface area and pore diameter were reduced. One-pot preparation of 2-ethylhexenal from propylene was achieved by as-mentioned catalyst. The appropriate ratio of two active species was that the content of nitrogen (primary amine) was about 1.73% and rhodium content was about 0.19%. And the field of 2-ethylhexenal was up to 75.0% within 6h under this condition.
本文首先采用一步法制备了铑膦配合物催化剂HRh(CO)(PPh_3)_3,考察了不同氢源对催化剂结构的影响。结果表明:以氢氧化钾为氢源能够高效的合成目标催化剂HRh(CO)(PPh_3)_3,铑的利用率为95%左右;以硼氢化钠为氢源,产物为trans-RhCl(CO)(PPh_3)_2和HRh(CO)(PPh_3)_3的混合物,甲醛的滴加速度对两种产物的组分有着重要的影响,随甲醛滴加速度的逐渐减慢,目标催化剂HRh(CO)(PPh_3)_3含量逐渐增多,trans-RhCl(CO)(PPh_3)_2的含量逐渐减少,铑的利用率为85%左右;常压下,以氢气作为氢源不能合成目标催化剂HRh(CO)(PPh_3)_3,产物为trans-RhCl(CO)(PPh_3)_2;
其次,利用丙烯加氢甲酰化反应对所制备催化剂HRh(CO)(PPh_3)_3的催化性能进行评价,并和工业上所用的催化剂ROPAC进行对比;考察了膦铑比、铑浓度、温度和一氧化碳分压等工艺条件对催化剂催化性能的影响。结果表明:该催化剂在丙烯加氢甲酰化反应中表现出较好的催化性能,在同等条件下其催化性能要优于工业上所用的ROPAC催化剂;其催化丙烯加氢甲酰化反应的较佳工艺条件为:温度为90℃,一氧化碳的分压为0.1 MPa,膦铑比为300,铑的浓度为300 ppm,该条件下2 h内丙烯的转化率为71.7%,产物的正异构比为8.10,平均反应速率为0.042 mol·L~(-1)·min~(-1),丙烯转化为丁醛的转化频率为864 h~(-1);
最后,本文通过在分子筛MCM-41表面嫁接有机胺官能团和锚定铑膦配合物催化剂HRh(CO)(PPh_3)_3制备双功能催化剂,考察了负载胺类型、氮和铑的负载量对催化剂催化性能的影响。结果显示:通过该法可以制得双功能催化剂MCM-41-NR1R2-Rh-P,制备过程中载体分子筛MCM-41的晶体结构未被破坏,但比表面积及孔道直径降低;该催化剂能够实现丙烯一锅法制备辛烯醛反应;两种活性组分的合适配比为氮(伯胺)的负载量为1.73%左右,铑的负载量为0.19%左右,该条件下6 h内辛烯醛的收率高达75.0%。
As we all know, study and development of catalyst are one of the core issues of the modern chemical industry. Nowadays, there are many problems in 4 sets of octanol devices in the current industry such as high energy consumption and high pollution, which is especially prominent in the days of calling energy conservation, green catalysis and green production processes. Therefore, it is a challenging but imperative research to develop a green catalytic process used in octanol devices.
First, a rhodium-phosphine complex catalyst HRh(CO)(PPh_3)_3 was prepared in one-step process. The effects of different hydrogen were investigated on the structure of catalyst. The results showed that with potassium hydroxide as a hydrogen source, HRh(CO)(PPh_3)_3 can be efficiently synthesized and the utilization ratio of Rh reached about 95%. While with sodium borohydride as a hydrogen source, the product was the mixture of trans-RhCl(CO)(PPh_3)_2 and HRh(CO)(PPh_3)_3. The dropping rate of formaldehyde had a significant impact on components of the two products. As the dropping rate of formaldehyde gradually slowed down, the concentration of HRh(CO)(PPh_3)_3 gradually increased, while the content of trans-RhCl(CO)(PPh_3)_2 gradually decreased, and the utilization rate of Rh was about 85%. Using hydrogen as a hydrogen source under atmospheric pressure, HRh(CO)(PPh_3)_3 can not be synthesized, and the product was trans-RhCl(CO)(PPh_3)_2.
Second, the activity of the as-prepared catalysts has been evaluated by hydroformylation of propylene, which was compared with ROPAC used as the industrial catalyst. The ratio of phosphine and rhodium, the concentration of rhodium, temperature and partial pressure of carbon monoxide had great impact on catalytic performance. As-synthesized HRh(CO)(PPh_3)_3 had better catalytic performances for the hydroformylation of propylene, which was better than ROPAC used as the industrial catalyst under the same conditions. The better conditions of HRh(CO)(PPh_3)_3 in catalyzing hydroformylation of propylene were that temperature was 90℃, the partial pressure of carbon monoxide was 0.1 MPa, the ratio of phosphine and rhodium was 300 and the concentration of rhodium was 300 ppm. Under these conditions, the conversion of propylene was 71.7% within 2h and the n/i of product was 8.10 while the average reaction rate was 0.042 mol·L~(-1)·min~(-1) and the conversion frequency of propylene to butyraldehyde was 864 h-1;
Last, the dual-function catalyst was prepared by grafting organoamine and rhodium-phosphine HRh(CO)(PPh_3)_3 on the MCM-41 surface. And the impact of types of amines, nitrogen amount and the amount of rhodium on the catalyst properties was investigated. The results were summarized as follows: dual-function catalyst MCM-41-NH_2-Rh-P was obtained by grafting method, and the crystal structure of MCM-41 had not been destroyed, but the surface area and pore diameter were reduced. One-pot preparation of 2-ethylhexenal from propylene was achieved by as-mentioned catalyst. The appropriate ratio of two active species was that the content of nitrogen (primary amine) was about 1.73% and rhodium content was about 0.19%. And the field of 2-ethylhexenal was up to 75.0% within 6h under this condition.
引文
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