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Oxidation Processes: Experimental Study and Theoretical Investigations

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Oxidation Processes: Experimental Study and Theoretical Investigations By Nada Mohammed Al-Ananzeh A Dissertation Submitted to the Faculty of the WORCESTER POLYTECHNIC INSTITUTE in partial fulfillment of the requirements for the Degree of Doctor of Philosophy in Chemical Engineering April 2004 Approved by: --------------------------------------------------------------------------------------- Robert Thompson, Ph.D., Advisor Professor of Chemical Engineering Worcester Polytechnic --------------------------------------------------------------------------------------- John Bergendahl, Ph.D. Assistant Professor of Civil and Environmental Engineering Worcester Polytechnic Institute -------------------------------------------------------------------------------- Fabio H. Ribeiro, Ph.D. Professor of Chemical Engineering Purdue University i Abstract Oxidation reactions are of prime importance at an industrial level and correspond to a huge market. Oxidation reactions are widely practiced in industry and are thoroughly studied in academic and industrial laboratories. Achievements in oxidation process resulted in the development of many new selective oxidation processes. Environmental protection also relies mainly on oxidation reactions. Remarkable results obtained in this field contributed to promote the social image of chemistry which gradually changes from being the enemy of nature to becoming its friend and savior. This study dealt with two aspects regarding oxidation process. The first aspect represented an experimental study for the catalytic partial oxidation of benzene to phenol using Pd membrane in the gaseous phase. The second part was a theoretical study for some of the advanced oxidation process (AOPs) which are applied for contaminant destructions in polluted waters. Niwa and coworkers* reported a one step catalytic process to convert benzene to phenol using Pd membrane. According to their work, this technique will produce a higher yield than current cumene and nitrous oxide based industrial routes to phenol. A similar system to produce phenol from benzene in one step was studied in this work. Results at low conversion of benzene to phenol were obtained with a different selectivity from the reported work. High conversion to phenol was not obtained using the same arrangement as the reported one. High conversion to phenol was obtained using a scheme different from the one reported by Niwa et al1. It was found that producing phenol from benzene is not related to Pd- membrane since phenol was produced by passing all reactants over a Pd catalyst. Within the studied experimental conditions, formation of phenol was related to Pd catalyst since Pt catalyst was not capable of activating benzene to produce phenol. Other evidence was the result of a blank experiment, where no catalyst was used. From this experiment no phenol was produced. A kinetic model for the advanced oxidation process using ultraviolet light and hydrogen peroxide (UV/H2O2) in a completely mixed batch reactor has been tested for the destruction of humic acid in aqueous solutions. Known elementary chemical reactions with the corresponding rate constants were taken from the literature and used in this model. Photochemical reaction parameters of hydrogen peroxide and humic acid were also taken from the literature. Humic acid was assumed to be mainly destroyed by direct photolysis and • OH radicals. The rate constant for the HA- • OH reaction was optimized from range of values in the literature. Other fitted parameters were the rate constant of direct photolysis of hydrogen peroxide and humic acid. A series of reactions were proposed for formation of organic byproducts of humic acid destruction by direct photolysis and • OH radicals. The corresponding rate constants were optimized based on the best fit within the range of available published data. This model doesn’t assume the net formation of free radicals species is zero. The model was verified by predicting the degradation of HA and H2O2 for experimental data taken from the literature. The kinetic model predicted the effect of initial HA and H2O2 concentration on the process performance regarding the residual fraction of hydrogen peroxide and nonpurgeable dissolved organic carbon (NPDOC). The kinetic model was used to study the effect of the presence of carbonate/bicarbonate on the rate of degradation of NPDOC using hydrogen peroxide and UV (H2O2/UV) oxidation. Experimental data taken from literature were used to test the kinetic model in the presence of carbonate/bicarbonate at different concentrations. The kinetic model was able to describe the trend of the experimental data. The kinetic model simulations, along with the experimental data for the conditions in this work, showed a retardation effect on the rate of degradation of NPDOC due to the presence of bicarbonate and carbonate. This effect was attributed to the scavenging of the hydroxyl radicals by carbonate and bicarbonate. A kinetic model for the degradation of methyl tert-butyl ether (MTBE) in a batch reactor applying II o Fenton’s reagent (Fe / H2O2) and Fenton-like reagent (Fe / H2O2) in aqueous solutions was proposed. All of the rate and equilibrium constants for hydrogen peroxide chemistry in aqueous solutions were taken from the literature. Rate and equilibrium constants for ferric and ferrous ions reactions in this model were taken from the reported values in the literature, except for the rate constant for the reaction of ferric ions with hydrogen peroxide where it was fitted within the range that was reported in the literature. Rate constant for iron dissolution was also a fitted parameter. The mechanism of MTBE degradation by the * Niwa, S. et al., Science 295 (2002) 105 ii hydroxyl radicals was proposed based on literature studies. The kinetic model was tested on available experimental data from the literature which involved the use of Fenton’s reagent and Fenton-like reagent for MTBE degradation. The degradation of MTBE in Fenton’s reagent work was characterized to proceed II by two stages, a fast one which involved the reaction of ferrous ions with hydrogen peroxide (Fe /H2O2 stage) and another, relatively, slower stage which involved the reaction of ferric ions with hydrogen III II peroxide (Fe /H2O2 stage). The experimental data of MTBE degradation in the Fe /H2O2 stage were not III sufficient to validate the model, however the model predictions of MTBE degradation in the Fe /H2O2 stage was good. Also, the model was able to predict the byproducts formation from MTBE degradation and their degradation especially methyl acetate, and tert-butyl alcohol. The effect of each proposed reaction on MTBE degradation and the byproducts formation and degradation was elucidated based on a sensitivity analysis. The kinetic model predicted the degradation of MTBE for Fenton-like reagent for the tested experimental data. Matlab (R13) was used to solve the set of ordinary nonlinear stiff differential equations that described rate of species concentrations in each advanced oxidation kinetic model. iii Extended Abstract Oxidation reactions are of prime importance at an industrial level and correspond to a huge market, for example in the US in 1994, about 31% of the catalytic production of major organic chemicals corresponded to oxidation catalytic processes. Oxidation reactions are widely practiced in industry and are thoroughly studied in academic and industrial laboratories. Catalyzed oxidation reactions are today one of the most dynamic and fruitful field in catalysis. Major achievements were attained in oxidation catalysis. They resulted in the development of many new selective oxidation processes; for example, oxidation of ethylene to acetaldehyde, oxidation of butylenes to maleic anhydride, oxidation of methanol to formaldehyde, etc. These processes have deeply affected the structure of the global chemical industry. Environmental protection also relies mainly on oxidation reactions. Remarkable results obtained in this field contribute to promote the social image of chemistry which gradually changes from being the enemy of nature to becoming its friend and savior. This study dealt with two major aspects regarding oxidation processes. The first aspect represented an experimental study of the partial oxidation of benzene to phenol in the gaseous phase using Pd membrane. The second part was a theoretical study for some of the advanced oxidation process (AOPs) which are applied for contaminant destructions in polluted waters. In both parts the main oxidant was the hydroxyl radical ( • OH ) which was produced insitu from the system reagents. The first chapter of this thesis addresses the experimental study and the remaining chapters address the theoretical study. In Chapter 2, a kinetic model for the destruction of humic acids (HA) using UV/H2O2 was tested on experimental data from the literature. The study conducted in Chapter 2 was investigated further in Chapter 3 by including the effect of bicarbonate/carbonate on the rate of HA degradation. This was performed by testing the kinetic model on reported experimental data. In Chapter 4 another type of AOPs, which relies on the use of Fenton’s reagent and Fenton-like reagent, was studied. Experimental data, taken from the literature, for methyl tert-butyl ether (MTBE) degradation in such systems, was used to test a kinetic model for such systems. Phenol is an important intermediate for the synthesis of petrochemicals, agrochemicals, and plastics. An example of using phenol as an intermediate in the synthetic
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