金属卟啉仿生催化对二甲苯氧化反应、机理及动力学研究
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摘要
对苯二甲酸(TPA)是一种制备聚对苯二甲酸乙烯酯(PET)的重要原料。目前世界范围内70%的对苯二甲酸是通过催化氧化对二甲苯(PX)反应的途径而得到的。现代工业生产是在80%HOAc溶剂中采用Co(OAc)2/Mn(OAc)2/HBr作催化剂来实现对二甲苯氧化制备对苯二甲酸的。因HOAc使用而造成的反应器壁的腐蚀以及因溴化物的使用引起的环境污染已成为现代工业生产过程的主要缺点。为了实现对二甲苯更好的催化氧化,科学家们已经尝试了很多新的催化方法。但是上述成就并没有撼动工业制备对苯二甲酸所选用的Co(OAc)2/Mn(OAc)2/HBr催化剂体系。因此发展一种新的符合绿色化学要求的对二甲苯氧化方法仍然是富有挑战意义的课题。
本文我们首次研究了氯化[5,10,15,20-四苯基卟吩]合锰(Tp-Cl)PPMnCl)/Co(OAc)2催化空气无溶剂氧化对二甲苯制备对苯二甲酸的反应。无溶剂条件下T(p-Cl)PPMnCl与Co(OAc)2之间存在复合催化作用。我们还研究了金属卟啉-醋酸钴复合催化作用的机理以及对二甲苯氧化反应的动力学。论文工作内容如下：
1、尝试了以T(p-Cl)PPMnCl/Co(OAc)2为催化剂,在无溶剂的条件下通过对二甲苯氧化制备对苯二甲酸的新方法。研究发现,T(p-Cl)PPMnCl和Co(OAc)2之间存在复合催化作用。当T(p-Cl)PPMnCl和Co(OAc)2共同使用时,对苯二甲酸产率较二者单独使用时显著提高。研究表明,对甲基苯甲酸氧化步骤是对二甲苯氧化为对苯二甲酸反应过程的速决步,向Co(OAc)2催化反应体系中添加少量的T(p-Cl)PPMnCl能明显加快反应的速决步。我们还详细考察了催化剂浓度和反应条件对对二甲苯氧化反应的影响。
2、研究了T(p-Cl)PPMnCl/Co(OAc)2复合催化空气氧化对甲基苯甲酸(PTA)的反应。T(p-Cl)PPMnCl/Co(OAc)2在PTA的催化氧化反应中表现出复合催化作用。研究表明,对甲基苯甲酸氧化反应受催化剂组成、催化剂浓度以及反应条件的影响。
3、探讨了T(p-Cl)PPMnCl/Co(OAc)2复合催化作用的机理,通过研究Co3+催化空气氧化对甲基苯甲酸的反应,我们发现T(p-Cl)PPMnCl与底物作用会产生更多的过氧化物,过氧化物将Co2+氧化为Co3+,Co3+促进氧化反应的进行。研究了对二甲苯氧化反应过程中生成的中间产物对甲基苯甲醇(TALC)对T(p-Cl)PPMnCl的结构以及催化性能的影响。通过光谱学分析,我们发现对甲基苯甲醇可以与T(p-Cl)PPMnCl以1：1的比例轴向配位,配位与对甲基苯甲醇的浓度正相关。T(p-Cl)PPMnCl与对甲基苯甲醇配位会导致锰卟啉催化性能降低。基于上述实验结果,我们提出了T(p-Cl)PPMnCl与Co(OAc)2复合催化对二甲苯空气氧化制备对苯二甲酸的作用机理。
4、我们采用拟稳态假设建立了对二甲苯氧化反应的分数形式的动力学模型,并通过实验数据回归确定了模型参数。我们的动力学模型可以很好的解释实验中观察到的现象。动力学模型计算结果与实验数据能够较好地吻合,我们从动力学方面证明了金属卟啉在催化对二甲苯氧化时存在自由基逃逸和自由基捕获两种相互竞争途径的反应途径。
与其它无溶剂催化体系相比,本工艺具有较高的对苯二甲酸产率,反应条件相对更加温和,环境更友好,并且无需任何添加剂和引发剂。
Terephthalic acid (TPA) is an important raw material for the production of polyethylene terephthalate (PET). Nowadays70%of TPA used worldwide is prepared by the catalytic oxidation of p-xylene (PX). Typically, the oxidation of PX is catalyzed by a combination of Co(OAc)2/Mn(OAc)2/HBr using80%HO Ac as solvent in industry. The corrosion of the reactors due to the use of HOAc as solvent and the serious environmental threat posed by bromide have become the major shortcomings. In order to find out a better way for PX oxidation, scientists have studied many new catalytic processes. However, above achievements did not agitate the industrial preparation of TPA catalyzed by Co(OAc)2/Mn(OAc)2/HBr. The development of new PX oxidation processes fitting the requirements of green chemistry still remains a challenge.
In this paper, solvent-free oxidation of PX to TPA with air catalyzed by tetra(p-chlorophenylporphinato)manganese chloride (T(p-Cl)PPMnCl)/Co(OAc)2was reported for the first time, and the co-catalysis between T(p-Cl)PPMnCl and cobalt acetate was discovered. Mechanism and kinetics studies on the oxidation of p-xylene to terephthalate acid cocatalyzed by metalloporphyrin and cobalt acetate were conducted. The main work of this paper was as follows:
Firstly, an attempt has been made to prepare TPA by solvent-free oxidation of PX with air over T(p-Cl)PPMnCl and cobalt acetate. The co-catalysis between T(p-Cl)PPMnCl and Co(OAc)2has been discovered. TPA yield could be increased significantly when T(p-Cl)PPMnCl and Co(OAc)2were used together. Studies indicate that the p-toluic acid (PTA) oxidation step is the rate-determining step of the oxidation process of PX to TPA. The addition of T(p-Cl)PPMnCl into the reaction mixture over Co(OAc)2significantly accelerated the rate-determining step. Effects of catalyst concentrations and reaction conditions on the reaction were also investigated.
Secondly, the aerobic oxidation of PTA to TPA over T(p-Cl)PPMnCl and Co(OAc)2was studied. The co-catalysis of T(p-Cl)PPMnCl/Co(OAc)2was operative in the catalytic oxidation of PTA. The studies indicated that the PTA oxidation was influenced by the catalyst composition, catalyst concentrations and reaction conditions.
Thirdly, the mechanism of co-catalysis between T(p-Cl)PPMnCl and Co(OAc)2 was investigated. The study of aerobic oxidation of PTA catalyzed by Co3+indicated that the function of T(p-Cl)PPMnCl might be to produce more peroxides from the substrate; The Co3+, obtained by the reaction of peroxides and Co2+, could promote the PTA oxidation. Effects of p-toluic alcohol (TALC) product on the structure and catalytic performance of T(p-Cl)PPMnCl in aerobic oxidation of PX were also studied. Axial coordination of TALC to T(p-Cl)PPMnCl was confirmed by spectroscopic analysis. The molecular TALC could axially coordinate to the T(p-Cl)PPMnCl in the ratio1:1, and the coordination is positively related with TALC concentration. The catalytic performance of T(p-Cl)PPMnCl dropped sharply when T(p-Cl)PPMnCl was coordinated with TALC. A preliminary mechanism of this co-catalyzed oxidation reaction was proposed based on these experimental results.
Fourthly, a fractional-like kinetic model was derived from the assumed mechanism via the application of steady state approximation. We applied the experimental data to regress the kinetic model parameters in order to obtain those model parameters. Our kinetic model could explain and correlate the experimental observations well. Based on the fact that the kinetic model's well fitting of experimental data, we speculate that the aerobic oxidation of PX has two competing reaction paths, i.e. the radicals escape way and the radicals capture way.
Compared with other solvent-free catalyst systems, the reaction system in this paper has the advantages of giving higher TPA yield, operating under relatively milder reaction conditions, being more environmental friendly and it do not require the use of any additive or initiator.
本文我们首次研究了氯化[5,10,15,20-四苯基卟吩]合锰(Tp-Cl)PPMnCl)/Co(OAc)2催化空气无溶剂氧化对二甲苯制备对苯二甲酸的反应。无溶剂条件下T(p-Cl)PPMnCl与Co(OAc)2之间存在复合催化作用。我们还研究了金属卟啉-醋酸钴复合催化作用的机理以及对二甲苯氧化反应的动力学。论文工作内容如下：
1、尝试了以T(p-Cl)PPMnCl/Co(OAc)2为催化剂,在无溶剂的条件下通过对二甲苯氧化制备对苯二甲酸的新方法。研究发现,T(p-Cl)PPMnCl和Co(OAc)2之间存在复合催化作用。当T(p-Cl)PPMnCl和Co(OAc)2共同使用时,对苯二甲酸产率较二者单独使用时显著提高。研究表明,对甲基苯甲酸氧化步骤是对二甲苯氧化为对苯二甲酸反应过程的速决步,向Co(OAc)2催化反应体系中添加少量的T(p-Cl)PPMnCl能明显加快反应的速决步。我们还详细考察了催化剂浓度和反应条件对对二甲苯氧化反应的影响。
2、研究了T(p-Cl)PPMnCl/Co(OAc)2复合催化空气氧化对甲基苯甲酸(PTA)的反应。T(p-Cl)PPMnCl/Co(OAc)2在PTA的催化氧化反应中表现出复合催化作用。研究表明,对甲基苯甲酸氧化反应受催化剂组成、催化剂浓度以及反应条件的影响。
3、探讨了T(p-Cl)PPMnCl/Co(OAc)2复合催化作用的机理,通过研究Co3+催化空气氧化对甲基苯甲酸的反应,我们发现T(p-Cl)PPMnCl与底物作用会产生更多的过氧化物,过氧化物将Co2+氧化为Co3+,Co3+促进氧化反应的进行。研究了对二甲苯氧化反应过程中生成的中间产物对甲基苯甲醇(TALC)对T(p-Cl)PPMnCl的结构以及催化性能的影响。通过光谱学分析,我们发现对甲基苯甲醇可以与T(p-Cl)PPMnCl以1：1的比例轴向配位,配位与对甲基苯甲醇的浓度正相关。T(p-Cl)PPMnCl与对甲基苯甲醇配位会导致锰卟啉催化性能降低。基于上述实验结果,我们提出了T(p-Cl)PPMnCl与Co(OAc)2复合催化对二甲苯空气氧化制备对苯二甲酸的作用机理。
4、我们采用拟稳态假设建立了对二甲苯氧化反应的分数形式的动力学模型,并通过实验数据回归确定了模型参数。我们的动力学模型可以很好的解释实验中观察到的现象。动力学模型计算结果与实验数据能够较好地吻合,我们从动力学方面证明了金属卟啉在催化对二甲苯氧化时存在自由基逃逸和自由基捕获两种相互竞争途径的反应途径。
与其它无溶剂催化体系相比,本工艺具有较高的对苯二甲酸产率,反应条件相对更加温和,环境更友好,并且无需任何添加剂和引发剂。
Terephthalic acid (TPA) is an important raw material for the production of polyethylene terephthalate (PET). Nowadays70%of TPA used worldwide is prepared by the catalytic oxidation of p-xylene (PX). Typically, the oxidation of PX is catalyzed by a combination of Co(OAc)2/Mn(OAc)2/HBr using80%HO Ac as solvent in industry. The corrosion of the reactors due to the use of HOAc as solvent and the serious environmental threat posed by bromide have become the major shortcomings. In order to find out a better way for PX oxidation, scientists have studied many new catalytic processes. However, above achievements did not agitate the industrial preparation of TPA catalyzed by Co(OAc)2/Mn(OAc)2/HBr. The development of new PX oxidation processes fitting the requirements of green chemistry still remains a challenge.
In this paper, solvent-free oxidation of PX to TPA with air catalyzed by tetra(p-chlorophenylporphinato)manganese chloride (T(p-Cl)PPMnCl)/Co(OAc)2was reported for the first time, and the co-catalysis between T(p-Cl)PPMnCl and cobalt acetate was discovered. Mechanism and kinetics studies on the oxidation of p-xylene to terephthalate acid cocatalyzed by metalloporphyrin and cobalt acetate were conducted. The main work of this paper was as follows:
Firstly, an attempt has been made to prepare TPA by solvent-free oxidation of PX with air over T(p-Cl)PPMnCl and cobalt acetate. The co-catalysis between T(p-Cl)PPMnCl and Co(OAc)2has been discovered. TPA yield could be increased significantly when T(p-Cl)PPMnCl and Co(OAc)2were used together. Studies indicate that the p-toluic acid (PTA) oxidation step is the rate-determining step of the oxidation process of PX to TPA. The addition of T(p-Cl)PPMnCl into the reaction mixture over Co(OAc)2significantly accelerated the rate-determining step. Effects of catalyst concentrations and reaction conditions on the reaction were also investigated.
Secondly, the aerobic oxidation of PTA to TPA over T(p-Cl)PPMnCl and Co(OAc)2was studied. The co-catalysis of T(p-Cl)PPMnCl/Co(OAc)2was operative in the catalytic oxidation of PTA. The studies indicated that the PTA oxidation was influenced by the catalyst composition, catalyst concentrations and reaction conditions.
Thirdly, the mechanism of co-catalysis between T(p-Cl)PPMnCl and Co(OAc)2 was investigated. The study of aerobic oxidation of PTA catalyzed by Co3+indicated that the function of T(p-Cl)PPMnCl might be to produce more peroxides from the substrate; The Co3+, obtained by the reaction of peroxides and Co2+, could promote the PTA oxidation. Effects of p-toluic alcohol (TALC) product on the structure and catalytic performance of T(p-Cl)PPMnCl in aerobic oxidation of PX were also studied. Axial coordination of TALC to T(p-Cl)PPMnCl was confirmed by spectroscopic analysis. The molecular TALC could axially coordinate to the T(p-Cl)PPMnCl in the ratio1:1, and the coordination is positively related with TALC concentration. The catalytic performance of T(p-Cl)PPMnCl dropped sharply when T(p-Cl)PPMnCl was coordinated with TALC. A preliminary mechanism of this co-catalyzed oxidation reaction was proposed based on these experimental results.
Fourthly, a fractional-like kinetic model was derived from the assumed mechanism via the application of steady state approximation. We applied the experimental data to regress the kinetic model parameters in order to obtain those model parameters. Our kinetic model could explain and correlate the experimental observations well. Based on the fact that the kinetic model's well fitting of experimental data, we speculate that the aerobic oxidation of PX has two competing reaction paths, i.e. the radicals escape way and the radicals capture way.
Compared with other solvent-free catalyst systems, the reaction system in this paper has the advantages of giving higher TPA yield, operating under relatively milder reaction conditions, being more environmental friendly and it do not require the use of any additive or initiator.
引文
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