硝基苯加氢合成对氨基苯酚的反应及其动力学研究
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摘要
相对传统的氯苯经过硝化、水解、还原三步反应制备对氨基苯酚的路线,硝基苯在Pt/C催化下选择性加氢生成羟基苯胺、同时在稀硫酸中经Bamberge重排,一步法制备对氨基苯酚和副产苯胺的路线,具有原子经济性高、有很好的工业化前景。
硝基苯在Pt/C催化剂和无机酸下加氢制备出对氨基苯酚,工业化要研究解决三类主要问题：硝基苯在Pt/C催化剂和无机酸下加氢的氢气相、硝基苯有机相、稀硫酸无机相、Pt/C催化剂固相的四相态(气-液-液-固)工程放大问题,工程上要设计出四相态的混合良好的大型反应器,需要解决四相态反应的工程或宏观动力学；贵金属Pt/C催化剂的寿命问题,工程上要设计试验出寿命满足经济要求Pt/C催化剂,需要解决加氢催化反应的催化剂失活动力学；反应温度下的稀硫酸的耐腐蚀设备材质选择问题。
采用文丘里涡流自吸结构搅拌装置,逐步增大变频调节的转速,反应速率逐步增大直至不变,消除了相间构成外扩散阻力；采用筛分分级的逐步减小的Pt/C催化剂粒径,反应速率逐步增大直至不变,消除了催化剂颗粒的内扩散阻力；在无内外扩散阻力下,硝基苯浓度可以认为不变,改变另一反应组分—氢气的压力,得到不同压力下的对氨基苯酚和苯胺的生产反应速率,积分法得到反应速率相对氢气压力的级数；改变反应温度,得到不同温度下的反应速率,利用Arrenius方程得到反应的活化能。
催化剂连续循环套用,反应速率随反应时间加长而减小,催化剂活性减小,利用Levenspiel的失活速率的模型方程拟合实验数据,得到失活速率对活性的级数；改变反应温度,得到不同温度下的失活速率,利用Arrenius方程得到失活速率的活化能。
本论文创新性研究了在消除催化剂的内外扩散阻力下,得到硝基苯选择性催化加氢四相态反应的对氨基苯酚和苯胺生成速率宏观动力学；利用催化剂连续循环套用,得到Pt/C催化剂的失活动力学,同时分析了随着Pt/C催化剂的失活,对氨基苯酚相对苯胺的选择性改变机理。研究给出的提高催化剂寿命的制备和使用方法,能满足满足经济要求。研究试验出耐稀硫酸腐蚀的哈氏合金材质,并对四相态反应器进行了设计,进一步进行了工业放大试验。
本研究的创新主要是建立了硝基苯选择性催化加氢四相态反应的对氨基苯酚和苯胺的生成速率宏观动力学,得到Pt/C催化剂的失活动力学,设计了经工业放大成功试验的四相态反应器。
As compared with the traditional processes of p-aminophenol from cholobenzene via three-step reaction of nitration and hydrolysis and reduction, the one-pot method for the preparation of p-aminophenol via hydroxylbenzeneamine precursor by Bamberge rearrangement from nitrobenzene in the presence of Pt/C catalyst appears of the atom economy towards an promising industrialization.
For the industrial preparation of p-aminophenol from nitrobenzene with catalytic hydrogenation it is necessary to resolve the three main problems, which are engineering scale-up for four-phase involving hydrogen gas phase, nitrobenzene organic phase, sulfuric acid inorganic phase and Pt/C solid phase, a well-mixed reactor design as well as the macro-kinetics in engineering. The catalyst for noble metal Pt supported C could be met the economic demand on theoretical and practical resolutions for the catalyst activity and the catalytic reaction kinetics. Besides, the reactor equipment resistance to the dilute sulfuric acid corrosion must be selected.
A Venturi mixer of vortex self-induction was employed to increase the rotating speed progressively by using frequency conversion equipment, since the rate could be increased correspondingly to a stable value so as to eliminate the exterior dispersion resistance from every phase. And with the decreasing the particle diameter progressively by a screening grading the rate was also increased correspondingly to a constant so that the interior dispersion resistance over the catalyst could be eliminated. The maintenance in constant concentration of nitrobenzene without the resistance from the interior and exterior dispersions the formation rate of p-aminophenol and aniline was varied with the hydrogen pressure and the reaction order could be obtained with an integration method. Moreover, the activation energy for the reaction can be obtained using the Arrenius equation by the formation rate of p-aminophenol and aniline with temperature variation.
The catalyst efficacy was decreased with the increasing recycle times. The order for the catalyst deactivation rate can be obtained using the simple expression (SPLE) model proposed by Leivenspill fitting the experiment date. The activation energy for the deactivation was obtained by the Arrenius equation.
Moreover, the four phase macro-kinetics for the formation of p-aminophenol and aniline by the selective catalytic hydrogenation of nitrobenzene without any resistance from the interior and exterior dispersion of catalyst, and deactivation kinetics for the Pt/C catalyst with the catalyst recycles were established. A plausible mechanism for the selective formation of p-aminophenol and aniline over Pt/C catalyst was suggested. The methodology for the preparation of Pt/C catalyst was developed to meet environmentally economic demand. Various technological parameters involving the Hastalloy resistant to the corrosion of the dilute sulfuric acid, the design for hydrogenation reactor for the four phases and the industrial scale experiment were discussed towards industrialization.
Therefore, three novel results have been achived in this paper. The first is the four phase macrokinetics for the formation of p-aminophenol and aniline by the selective catalytic hydrogenation of nitrobenzene. The second is the deactivation kinetics for the Pt/C catalyst with the catalytic recycles. The third is the design for hydrogenation reactor for the four phases via successful industrial scale experiment.
硝基苯在Pt/C催化剂和无机酸下加氢制备出对氨基苯酚,工业化要研究解决三类主要问题：硝基苯在Pt/C催化剂和无机酸下加氢的氢气相、硝基苯有机相、稀硫酸无机相、Pt/C催化剂固相的四相态(气-液-液-固)工程放大问题,工程上要设计出四相态的混合良好的大型反应器,需要解决四相态反应的工程或宏观动力学；贵金属Pt/C催化剂的寿命问题,工程上要设计试验出寿命满足经济要求Pt/C催化剂,需要解决加氢催化反应的催化剂失活动力学；反应温度下的稀硫酸的耐腐蚀设备材质选择问题。
采用文丘里涡流自吸结构搅拌装置,逐步增大变频调节的转速,反应速率逐步增大直至不变,消除了相间构成外扩散阻力；采用筛分分级的逐步减小的Pt/C催化剂粒径,反应速率逐步增大直至不变,消除了催化剂颗粒的内扩散阻力；在无内外扩散阻力下,硝基苯浓度可以认为不变,改变另一反应组分—氢气的压力,得到不同压力下的对氨基苯酚和苯胺的生产反应速率,积分法得到反应速率相对氢气压力的级数；改变反应温度,得到不同温度下的反应速率,利用Arrenius方程得到反应的活化能。
催化剂连续循环套用,反应速率随反应时间加长而减小,催化剂活性减小,利用Levenspiel的失活速率的模型方程拟合实验数据,得到失活速率对活性的级数；改变反应温度,得到不同温度下的失活速率,利用Arrenius方程得到失活速率的活化能。
本论文创新性研究了在消除催化剂的内外扩散阻力下,得到硝基苯选择性催化加氢四相态反应的对氨基苯酚和苯胺生成速率宏观动力学；利用催化剂连续循环套用,得到Pt/C催化剂的失活动力学,同时分析了随着Pt/C催化剂的失活,对氨基苯酚相对苯胺的选择性改变机理。研究给出的提高催化剂寿命的制备和使用方法,能满足满足经济要求。研究试验出耐稀硫酸腐蚀的哈氏合金材质,并对四相态反应器进行了设计,进一步进行了工业放大试验。
本研究的创新主要是建立了硝基苯选择性催化加氢四相态反应的对氨基苯酚和苯胺的生成速率宏观动力学,得到Pt/C催化剂的失活动力学,设计了经工业放大成功试验的四相态反应器。
As compared with the traditional processes of p-aminophenol from cholobenzene via three-step reaction of nitration and hydrolysis and reduction, the one-pot method for the preparation of p-aminophenol via hydroxylbenzeneamine precursor by Bamberge rearrangement from nitrobenzene in the presence of Pt/C catalyst appears of the atom economy towards an promising industrialization.
For the industrial preparation of p-aminophenol from nitrobenzene with catalytic hydrogenation it is necessary to resolve the three main problems, which are engineering scale-up for four-phase involving hydrogen gas phase, nitrobenzene organic phase, sulfuric acid inorganic phase and Pt/C solid phase, a well-mixed reactor design as well as the macro-kinetics in engineering. The catalyst for noble metal Pt supported C could be met the economic demand on theoretical and practical resolutions for the catalyst activity and the catalytic reaction kinetics. Besides, the reactor equipment resistance to the dilute sulfuric acid corrosion must be selected.
A Venturi mixer of vortex self-induction was employed to increase the rotating speed progressively by using frequency conversion equipment, since the rate could be increased correspondingly to a stable value so as to eliminate the exterior dispersion resistance from every phase. And with the decreasing the particle diameter progressively by a screening grading the rate was also increased correspondingly to a constant so that the interior dispersion resistance over the catalyst could be eliminated. The maintenance in constant concentration of nitrobenzene without the resistance from the interior and exterior dispersions the formation rate of p-aminophenol and aniline was varied with the hydrogen pressure and the reaction order could be obtained with an integration method. Moreover, the activation energy for the reaction can be obtained using the Arrenius equation by the formation rate of p-aminophenol and aniline with temperature variation.
The catalyst efficacy was decreased with the increasing recycle times. The order for the catalyst deactivation rate can be obtained using the simple expression (SPLE) model proposed by Leivenspill fitting the experiment date. The activation energy for the deactivation was obtained by the Arrenius equation.
Moreover, the four phase macro-kinetics for the formation of p-aminophenol and aniline by the selective catalytic hydrogenation of nitrobenzene without any resistance from the interior and exterior dispersion of catalyst, and deactivation kinetics for the Pt/C catalyst with the catalyst recycles were established. A plausible mechanism for the selective formation of p-aminophenol and aniline over Pt/C catalyst was suggested. The methodology for the preparation of Pt/C catalyst was developed to meet environmentally economic demand. Various technological parameters involving the Hastalloy resistant to the corrosion of the dilute sulfuric acid, the design for hydrogenation reactor for the four phases and the industrial scale experiment were discussed towards industrialization.
Therefore, three novel results have been achived in this paper. The first is the four phase macrokinetics for the formation of p-aminophenol and aniline by the selective catalytic hydrogenation of nitrobenzene. The second is the deactivation kinetics for the Pt/C catalyst with the catalytic recycles. The third is the design for hydrogenation reactor for the four phases via successful industrial scale experiment.
引文
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