固体氧化物催化草酸二乙酯和苯酚酯交换反应的研究
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摘要
碳酸二苯酯(DPC)是一种用途广泛的环保型化工中间体。以苯酚和草酸二乙酯(DEO)酯交换合成草酸二苯酯(DPO),DPO再脱羰基生成DPC是一条具有广阔发展前景的非光气法绿色合成工艺路线。本论文重点研究了苯酚与DEO的非均相酯交换合成DPO反应,对负载型TiO_2/SiO_2、MoO_3/SiO_2催化剂及复合型MoO_3-SiO_2催化剂在此酯交换反应中的催化作用进行了探讨。
通过对酯交换用催化剂进行活性测试以及BET、XRD、Raman、ICP、IR、XPS、NH3-TPD和吸附吡啶IR等表征,结果表明在苯酚和DEO酯交换反应中,催化剂的催化性能与活性组分在载体表面上的高度分散以及催化剂的弱酸性密切相关。
弱的Lewis酸中心是TiO_2/SiO_2、MoO_3/SiO_2和MoO_3-SiO_2催化剂催化DEO和苯酚酯交换反应合成DPO的活性中心。弱酸中心的唯一存在是获得产物高选择性的重要原因。
TiO_2和MoO_3在载体表面的存在状态是影响TiO_2/SiO_2、MoO_3/SiO_2及复合型MoO_3-SiO_2催化剂活性的关键因素,TiO_2和MoO_3以无定型单分子层高度分散在催化剂表面时,催化剂活性提高,并有助于中间产物乙基苯基草酸酯(EPO)歧化反应生成DPO,提高DPO选择性。当TiO_2和MoO_3以晶相存在时,催化剂活性下降,DPO选择性也降低。TiO_2和MoO_3负载量及催化剂焙烧温度是影响TiO_2和MoO_3存在状态的主要原因,负载量或焙烧温度过高都会引起TiO_2和MoO_3晶相的产生。
复合型MoO_3-SiO_2催化剂的反应性能优于负载型MoO_3/SiO_2。对于复合型MoO_3-SiO_2,MoO_3与SiO_2之间的相互作用较强,MoO_3主要以Mo-O-Si键的形式存在,形成更多的酸性中心,同时分散状态更好,因而有利于催化活性和DPO选择性的提高。当MoO_3含量为12%时,MoO_3-SiO_2的催化性能最佳,DEO转化率及DPO选择性、DPO收率分别为71.0%、32.0%和22.7%,目的产物EPO和DPO的总选择性为100%。
Much attention has been paid to the synthesis and application of diphenyl carbonate (DPC) because it can be used as an environmentally benign chemical intermediate. The transesterification of diethyl oxalate (DEO) with phenol to diphenyl oxalate (DPO) followed by decarbonylation of DPO to DPC is a promising non-phosgene route. In this thesis, the transesterification of diethyl oxalate (DEO) with phenol over heterogeneous catalysts are studied. The activity performance of supported TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3/SiO_2 mixed oxides catalysts are investigated in detail.
By means of BET, XRD, Raman, ICP, IR, XPS, NH3-TPD and FT-IR analysis of adsorbed pyridine, it can be concluded that the catalytic activities of supported catalysts are mainly attributed to the high dispersion of the catalysts on the support and the weak Lewis acid sites on the catalyst surface.
The weak lewis acid sites of TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3-SiO_2 catalysts are the active centers for the transesterification from DEO and Phenol. The merely existed weak Lewis acid sites in the TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3-SiO_2 catalysts result in high selectivity to target products.
The catalytic properties of TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3-SiO_2 catalysts are closely related with the state of TiO_2 and MoO_3. The TiO_2 and MoO_3 species in the form of amorphous state is responsible for the synthesis of ethylphenyl oxlate(EPO) and DPO, especially, for the disproportionation of EPO to DPO. When the crystal is formed, the catalyst activity and selectivity to DPO is decreased. Increasing the loading amount of TiO_2 and MoO_3 and improving calcination temperature lead to the formation of TiO_2 and MoO_3 crystalline, accordingly, the active properties of MoO_3/SiO_2 catalyst decreased.
The activity of MoO_3-SiO_2 mixed oxides by sol-gel method is better than the supported MoO_3/SiO_2 catalysts. IR investigation shows that most MoO_3 species insert into the silica framework, suggesting the strong interaction of MoO_3 and silica via the formation of Mo-O-Si bond. Accordingly, more acid aites are produced in more dispersed state, resulting in the improvement of the catalytic activity and selectivity to DPO. The catalyst of MoO_3/SiO_2 with 12% MoO_3 performed best, giving 71.0% conversion of DEO, 32.0% selectivity of DPO, 22.7% yield of DPO, and 100% total selectivity to DPO and EPO.
通过对酯交换用催化剂进行活性测试以及BET、XRD、Raman、ICP、IR、XPS、NH3-TPD和吸附吡啶IR等表征,结果表明在苯酚和DEO酯交换反应中,催化剂的催化性能与活性组分在载体表面上的高度分散以及催化剂的弱酸性密切相关。
弱的Lewis酸中心是TiO_2/SiO_2、MoO_3/SiO_2和MoO_3-SiO_2催化剂催化DEO和苯酚酯交换反应合成DPO的活性中心。弱酸中心的唯一存在是获得产物高选择性的重要原因。
TiO_2和MoO_3在载体表面的存在状态是影响TiO_2/SiO_2、MoO_3/SiO_2及复合型MoO_3-SiO_2催化剂活性的关键因素,TiO_2和MoO_3以无定型单分子层高度分散在催化剂表面时,催化剂活性提高,并有助于中间产物乙基苯基草酸酯(EPO)歧化反应生成DPO,提高DPO选择性。当TiO_2和MoO_3以晶相存在时,催化剂活性下降,DPO选择性也降低。TiO_2和MoO_3负载量及催化剂焙烧温度是影响TiO_2和MoO_3存在状态的主要原因,负载量或焙烧温度过高都会引起TiO_2和MoO_3晶相的产生。
复合型MoO_3-SiO_2催化剂的反应性能优于负载型MoO_3/SiO_2。对于复合型MoO_3-SiO_2,MoO_3与SiO_2之间的相互作用较强,MoO_3主要以Mo-O-Si键的形式存在,形成更多的酸性中心,同时分散状态更好,因而有利于催化活性和DPO选择性的提高。当MoO_3含量为12%时,MoO_3-SiO_2的催化性能最佳,DEO转化率及DPO选择性、DPO收率分别为71.0%、32.0%和22.7%,目的产物EPO和DPO的总选择性为100%。
Much attention has been paid to the synthesis and application of diphenyl carbonate (DPC) because it can be used as an environmentally benign chemical intermediate. The transesterification of diethyl oxalate (DEO) with phenol to diphenyl oxalate (DPO) followed by decarbonylation of DPO to DPC is a promising non-phosgene route. In this thesis, the transesterification of diethyl oxalate (DEO) with phenol over heterogeneous catalysts are studied. The activity performance of supported TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3/SiO_2 mixed oxides catalysts are investigated in detail.
By means of BET, XRD, Raman, ICP, IR, XPS, NH3-TPD and FT-IR analysis of adsorbed pyridine, it can be concluded that the catalytic activities of supported catalysts are mainly attributed to the high dispersion of the catalysts on the support and the weak Lewis acid sites on the catalyst surface.
The weak lewis acid sites of TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3-SiO_2 catalysts are the active centers for the transesterification from DEO and Phenol. The merely existed weak Lewis acid sites in the TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3-SiO_2 catalysts result in high selectivity to target products.
The catalytic properties of TiO_2/SiO_2, MoO_3/SiO_2 and MoO_3-SiO_2 catalysts are closely related with the state of TiO_2 and MoO_3. The TiO_2 and MoO_3 species in the form of amorphous state is responsible for the synthesis of ethylphenyl oxlate(EPO) and DPO, especially, for the disproportionation of EPO to DPO. When the crystal is formed, the catalyst activity and selectivity to DPO is decreased. Increasing the loading amount of TiO_2 and MoO_3 and improving calcination temperature lead to the formation of TiO_2 and MoO_3 crystalline, accordingly, the active properties of MoO_3/SiO_2 catalyst decreased.
The activity of MoO_3-SiO_2 mixed oxides by sol-gel method is better than the supported MoO_3/SiO_2 catalysts. IR investigation shows that most MoO_3 species insert into the silica framework, suggesting the strong interaction of MoO_3 and silica via the formation of Mo-O-Si bond. Accordingly, more acid aites are produced in more dispersed state, resulting in the improvement of the catalytic activity and selectivity to DPO. The catalyst of MoO_3/SiO_2 with 12% MoO_3 performed best, giving 71.0% conversion of DEO, 32.0% selectivity of DPO, 22.7% yield of DPO, and 100% total selectivity to DPO and EPO.
引文
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