微乳液法制备超微细包覆型催化剂及其催化苯酚氧化羰基化反应研究
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摘要
苯酚氧化羰基化反应合成碳酸二苯酯(DPC)直接利用初级化工原料CO、O_2及苯酚,具有工艺简单、原料便宜、无污染等特点,被视为合成DPC最有发展前途的方法。本文系统地研究了影响W/O微乳液体系相平衡的各种因素,利用W/O微乳液为纳米反应器制备了超微细包覆型催化剂,并对其在苯酚氧化羰基化反应中的活性进行了评价,最后对环境友好溶剂在该反应中的应用进行了探讨。
利用拟三元相图,对影响W/O微乳液相区的因素进行了考察。非离子表面活性剂TX-10较阳离子表面活性剂CTAB形成的W/O微乳液区域大;采用TX-10为表面活性剂时,当m(S)/m(CS)等于1:1时,所形成的界面膜具有较高的稳定性,因而具有较大的W/O微乳液区域;随着温度的升高,W/O微乳液区域呈缩小的趋势;水相pH值及助表面活性剂碳链长度的改变对W/O微乳液稳定区域的影响不大;当水相为电解质溶液时,W/O微乳液区域随其浓度的增大而减小。
当微乳液出现渗滤现象时,电导率的极大值随水相电导率的增大而增大,说明渗滤是由微乳液“内相”的连通所导致。在本文研究的微乳液体系中,首次发现当V(S+CS)/V(Oil)为1/1时,虽然微乳液体系的电导率随含水量的增加也出现极大值,但此值与水相的电导率无关。说明在此种情况下,随着水相含量的增加,W/O微乳液液滴数目逐渐增加,但互相之间并不连通,而是发生碰撞后又迅速分开,无法形成导电链,因此不能出现渗滤现象。
通过对TX-10/cyclohexane/n-hexanol/H_2O微乳液中水分子的O-H伸缩振动吸收峰的分峰拟合研究,发现该W/O微乳液中有三种不同的水分子,分别为处于表面活性剂长链之间的束缚水、水核中心部分的自由水和与表面活性剂氧乙烯链形成氢键的结合水。首次发现当含水量较低时,该微乳液中的水分子只有两种存在状态,一种是自由水,另一种是结合水。说明由于束缚水分子之间的作用力较弱,在含水量较低时,水分子优先形成自由水和与氧乙烯链形成结合水。微乳液中自由水、束缚水和结合水的摩尔分数随含水量增加的变化不大。
The direct synthesis of diphenyl carbonate (DPC) by oxidative carbonylation of phenolwith CO and O_2 is a promising synthetic method because of its simple process, cheap raw material and no pollutants produced. In this paper, the effects of various conditions on the phase equilibrium of water-in-oil (W/O) microemulsion were systematically studied. The preparation of ultrafine embedded catalyst using W/O microemulsion as nano-reactor for synthesis of DPC was also studied. At last, the exploration of environmentally friendly solvent for oxidative carbonylation of phenol was carried out.The influences on the homogeneous region in W/O microemulsion were studied by utilizing the pseudo-triangle phase diagram. The homogeneous region in W/O microemulsion stabilized by the nonionic surfactant TX-10 is larger than that of the microemulsion stabilized by the cation surfactant, CTAB. When using TX-10 as surfactant and the weight ratio of m(S)/m(CS) equals to 1, the interface between water and oil is the most stable and can form the largest W/O microemulsion homogeneous region. As the increase of temperature, the area of W/O microemulsion region decreases evidently. The pH value of the water phase and the length of the carbon chain of the co-surfactant have a less effect on the stability of the W/O microemulsion. When the electrolyte solution was used as water phase, the area of W/O microemulsion homogeneous region decreased with the increase of its concentration.The conductivity of the W/O microemulsion increases with that of water phase at percolation threshold. It indicates that the take place of percolation is due to the connection of 'inner phase' in W/O microemulsion. However, the percolation doesn't exist at any situations. When the weight ratio of V(S+CS)/V(Oil) equals to 1, the maximum value of the conductivity is independent of the value of the water phase. It can be concluded that the connection of the 'inner phase' doesn't occur at this situation. The number of the water core in the microemulsion increases with the increase of the water content. They collide with each other and then leave away rapidly not to form the electric chain, so the percolation doesn't happen.Using PeakFit 4.12 data processing soft, the stretching vibration of hydroxyl group of water molecular in W/O microemulsion was multiple fitted to study its existing mode. There are three different kinds of water molecular and they are the trapped water, which are trapped in the long carbon chain of the surfactant; the free water, which are located in the center of the water core; the bounded water, which are bounded with the oxyethylene of TX-10 by hydrogen bond. But when the water content is low, there are
only two kinds of water molecular and the trapped water is disappear. It shows that the acting force between the trapped water is weak. The free water and bounded water have priorities to be come into being when the water is a little. Moreover, the molar fractions of the three kinds of water molecular don't change markedly with the increase of the water content in microemulsion.The size controllable mono-dispersed spherical silica particles were prepared in the W/O microemulsion composed of ammonia, cyclohexane, TX-10 and n-hexanol. The silica particles' sizes range from 50 to 90 nm and can keep stability at high temperatures. A novel method, W/O microemulsion coupling with sol-gel process, for the preparation of ordered mesoporous silica powder with large specific surface area was developed.A novel ultrafine embedded catalyst Pd-Cu-O/SiO2 was prepared using W/O microemulsion as nano reactor. XRD, TEM, SEM and XPS were used to characterize it. It shows that the active center of the catalyst is the complex oxide CuPdO2 which was wholly or partly embedded in the silica particles in nano scale. Because of the protection by silica, this catalyst has higher activity and longer service time than that of the catalyst prepared by impregnation or sol-gel process. The DPC yield can reach to 35.4% and the TOP (Turnover of frequency) on Pd atom is 20.1 mol DPC/mol Pd?h. The heterogeneous Cu( II) promoter can change the active species from PdO to CuPdO2, then change the chemical environment of Pd atom and make it easy for Pd atoms to transfer electron to Cu atoms around. The homogeneous Cu2+ can promote the change Pd(0) -? Pd( II) more effectively than the heterogeneous Cu( II) because all the Cu2+ in the system can take action. While, only the Cu( II) that enter into the crystal lattice of PdO to form the CuPdO2 can obtain electron from Pd(0).The silica embedded metal palladium catalysts Pd/SiO2 were prepared using W/O microemulsion as nano-reactor. The size of metal palladium particles can be controlled in the range of 8-30 nm. From the evaluation by the synthesis of DPC, the catalyst with small palladium particles has higher activity and selectivity because the little the palladium particles, the larger the surface area of it and it implies the more probability for the molecular of reactants to contact with the active center. The reaction mechanism of oxidative carbonylation over Pd/SiO2 catalyst is the multiple step electron transfer process. Firstly, the metal Pd is oxidized to bivalent Pd( II) by Cu2+, while Cu2+ changes into Cu+. Then Pd( II) combines with PhO- to obtain the PhO-Pd-O-, which can react with CO to form PhO-C(=O)-Pd-O-. Finally, PhO-C(=O)-Pd-O- reacts with the second PhO- to prepare the PhO-C(=O)-O-Ph (DPC) and Pd(II) is reduced to Pd(0) simultaneously to finish the catalytic cycle.
利用拟三元相图,对影响W/O微乳液相区的因素进行了考察。非离子表面活性剂TX-10较阳离子表面活性剂CTAB形成的W/O微乳液区域大;采用TX-10为表面活性剂时,当m(S)/m(CS)等于1:1时,所形成的界面膜具有较高的稳定性,因而具有较大的W/O微乳液区域;随着温度的升高,W/O微乳液区域呈缩小的趋势;水相pH值及助表面活性剂碳链长度的改变对W/O微乳液稳定区域的影响不大;当水相为电解质溶液时,W/O微乳液区域随其浓度的增大而减小。
当微乳液出现渗滤现象时,电导率的极大值随水相电导率的增大而增大,说明渗滤是由微乳液“内相”的连通所导致。在本文研究的微乳液体系中,首次发现当V(S+CS)/V(Oil)为1/1时,虽然微乳液体系的电导率随含水量的增加也出现极大值,但此值与水相的电导率无关。说明在此种情况下,随着水相含量的增加,W/O微乳液液滴数目逐渐增加,但互相之间并不连通,而是发生碰撞后又迅速分开,无法形成导电链,因此不能出现渗滤现象。
通过对TX-10/cyclohexane/n-hexanol/H_2O微乳液中水分子的O-H伸缩振动吸收峰的分峰拟合研究,发现该W/O微乳液中有三种不同的水分子,分别为处于表面活性剂长链之间的束缚水、水核中心部分的自由水和与表面活性剂氧乙烯链形成氢键的结合水。首次发现当含水量较低时,该微乳液中的水分子只有两种存在状态,一种是自由水,另一种是结合水。说明由于束缚水分子之间的作用力较弱,在含水量较低时,水分子优先形成自由水和与氧乙烯链形成结合水。微乳液中自由水、束缚水和结合水的摩尔分数随含水量增加的变化不大。
The direct synthesis of diphenyl carbonate (DPC) by oxidative carbonylation of phenolwith CO and O_2 is a promising synthetic method because of its simple process, cheap raw material and no pollutants produced. In this paper, the effects of various conditions on the phase equilibrium of water-in-oil (W/O) microemulsion were systematically studied. The preparation of ultrafine embedded catalyst using W/O microemulsion as nano-reactor for synthesis of DPC was also studied. At last, the exploration of environmentally friendly solvent for oxidative carbonylation of phenol was carried out.The influences on the homogeneous region in W/O microemulsion were studied by utilizing the pseudo-triangle phase diagram. The homogeneous region in W/O microemulsion stabilized by the nonionic surfactant TX-10 is larger than that of the microemulsion stabilized by the cation surfactant, CTAB. When using TX-10 as surfactant and the weight ratio of m(S)/m(CS) equals to 1, the interface between water and oil is the most stable and can form the largest W/O microemulsion homogeneous region. As the increase of temperature, the area of W/O microemulsion region decreases evidently. The pH value of the water phase and the length of the carbon chain of the co-surfactant have a less effect on the stability of the W/O microemulsion. When the electrolyte solution was used as water phase, the area of W/O microemulsion homogeneous region decreased with the increase of its concentration.The conductivity of the W/O microemulsion increases with that of water phase at percolation threshold. It indicates that the take place of percolation is due to the connection of 'inner phase' in W/O microemulsion. However, the percolation doesn't exist at any situations. When the weight ratio of V(S+CS)/V(Oil) equals to 1, the maximum value of the conductivity is independent of the value of the water phase. It can be concluded that the connection of the 'inner phase' doesn't occur at this situation. The number of the water core in the microemulsion increases with the increase of the water content. They collide with each other and then leave away rapidly not to form the electric chain, so the percolation doesn't happen.Using PeakFit 4.12 data processing soft, the stretching vibration of hydroxyl group of water molecular in W/O microemulsion was multiple fitted to study its existing mode. There are three different kinds of water molecular and they are the trapped water, which are trapped in the long carbon chain of the surfactant; the free water, which are located in the center of the water core; the bounded water, which are bounded with the oxyethylene of TX-10 by hydrogen bond. But when the water content is low, there are
only two kinds of water molecular and the trapped water is disappear. It shows that the acting force between the trapped water is weak. The free water and bounded water have priorities to be come into being when the water is a little. Moreover, the molar fractions of the three kinds of water molecular don't change markedly with the increase of the water content in microemulsion.The size controllable mono-dispersed spherical silica particles were prepared in the W/O microemulsion composed of ammonia, cyclohexane, TX-10 and n-hexanol. The silica particles' sizes range from 50 to 90 nm and can keep stability at high temperatures. A novel method, W/O microemulsion coupling with sol-gel process, for the preparation of ordered mesoporous silica powder with large specific surface area was developed.A novel ultrafine embedded catalyst Pd-Cu-O/SiO2 was prepared using W/O microemulsion as nano reactor. XRD, TEM, SEM and XPS were used to characterize it. It shows that the active center of the catalyst is the complex oxide CuPdO2 which was wholly or partly embedded in the silica particles in nano scale. Because of the protection by silica, this catalyst has higher activity and longer service time than that of the catalyst prepared by impregnation or sol-gel process. The DPC yield can reach to 35.4% and the TOP (Turnover of frequency) on Pd atom is 20.1 mol DPC/mol Pd?h. The heterogeneous Cu( II) promoter can change the active species from PdO to CuPdO2, then change the chemical environment of Pd atom and make it easy for Pd atoms to transfer electron to Cu atoms around. The homogeneous Cu2+ can promote the change Pd(0) -? Pd( II) more effectively than the heterogeneous Cu( II) because all the Cu2+ in the system can take action. While, only the Cu( II) that enter into the crystal lattice of PdO to form the CuPdO2 can obtain electron from Pd(0).The silica embedded metal palladium catalysts Pd/SiO2 were prepared using W/O microemulsion as nano-reactor. The size of metal palladium particles can be controlled in the range of 8-30 nm. From the evaluation by the synthesis of DPC, the catalyst with small palladium particles has higher activity and selectivity because the little the palladium particles, the larger the surface area of it and it implies the more probability for the molecular of reactants to contact with the active center. The reaction mechanism of oxidative carbonylation over Pd/SiO2 catalyst is the multiple step electron transfer process. Firstly, the metal Pd is oxidized to bivalent Pd( II) by Cu2+, while Cu2+ changes into Cu+. Then Pd( II) combines with PhO- to obtain the PhO-Pd-O-, which can react with CO to form PhO-C(=O)-Pd-O-. Finally, PhO-C(=O)-Pd-O- reacts with the second PhO- to prepare the PhO-C(=O)-O-Ph (DPC) and Pd(II) is reduced to Pd(0) simultaneously to finish the catalytic cycle.
引文
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