Oxidation Processes: Experimental Study and Theoretical Investigations

Total Page:16

File Type:pdf, Size:1020Kb

Oxidation Processes: Experimental Study and Theoretical Investigations 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
Recommended publications
  • Download This Article PDF Format
    RSC Advances View Article Online PAPER View Journal | View Issue A new dendrimer series: synthesis, free radical scavenging and protein binding studies† Cite this: RSC Adv., 2020, 10,21914 Dhaval Makawana and Man Singh * Tri-o-tolyl benzene-1,3,5-tricarboxylate (TOBT (T0)), tri-4-hydroxyphenyl benzene-1,3,5-tricarboxylate (THBT (T1)), and tri-3,5-dihydroxyphenyl benzene-1,3,5-tricarboxylate (TDBT (T2)), a series of 1st tier dendrimers with a common 1,3,5-benzenetricarbonyl trichloride/trimesoyl chloride (TMC) core, are reported. T0 does not have any replaceable H+ on its terminal phenyl group, acting as a branch. T1 has one phenolic –OH at the para position and T2 has two phenolic –OH groups at the 3 and 5 positions of each terminal phenyl group. During synthesis, these –OH groups at the terminal phenyl groups were protected through tert-butyldimethylsilyl chloride (TBDMSCl) assisted with t-BuOK in DCM, THF, indazole, 4-dimethylaminopyridine (DMAP), and tertiary-n-butyl ammonium fluoride (TBAF). MTBDMSP (mono-tertiary butyl dimethylsilane phloroglucinol), DTBDMSP (di-tertiary butyl dimethylsilane phloroglucinol), and TTBDMSP (tri-tertiary butyl dimethylsilane phloroglucinol) were obtained with >90% Creative Commons Attribution-NonCommercial 3.0 Unported Licence. yield, and TTBDMSP phenolic derivatives (PDs) were developed to synthesize T0, T1, and T2 dendrimers by deprotecting with TBAF. T0 showed superhydrophobic properties as it did not dissolve in methanol, contrary to T1 and T2, but dissolved in acetone. Their structures were determined using 1H and 13C NMR Received 7th May 2020 spectroscopies, and mass spectrometry. Their scavenging activities were studied using UV-Vis Accepted 25th May 2020 spectrophotometry compared with ascorbic acid and protein binding was studied with bovine serum DOI: 10.1039/d0ra04102e albumin (BSA) and lysozyme (lyso).
    [Show full text]
  • PHENOLS Guidelines for the Protection Mono- and Dihydric Phenols of Aquatic Life
    Canadian Water Quality PHENOLS Guidelines for the Protection mono- and dihydric phenols of Aquatic Life henols and phenolic substances are aromatic may occur, as 1.3–15 µg⋅L-1 has been found in hydroxy compounds classified as monohydric (e.g., precipitation (Levsen et al. 1991). P phenol, cresols [methylphenols], xylenols [dimethylphenols]), dihydric (e.g., catechols [o- The concentration of total phenol is monitored more often dihydroxybenzenes], resorcinols [m-dihydroxybenzenes]) than monohydric or dihydric phenol (NAQUADAT or polyhydric (with three or more hydroxy groups), 1985). Most natural sources release only trace amounts of depending on the number of hydroxyl groups attached to phenolic substances to water. Phenol concentrations in the aromatic benzene ring (McNeely et al. 1979). The surface waters are generally <2 µg⋅L-1 (Environment -1 chemical formula for phenol (parent structure) is C6H5OH, Canada 1998a). Phenols levels ranging from <0.1 µg⋅kg and its CAS number is 108-95-2. Mono- and dihydric (detection limit) to 200 mg⋅kg-1 in sediment samples have phenols have not been produced in Canada since 1992, also been reported (Paul and Laliberté 1987; Laliberté although imports for 1995 and 1996 totaled 0.76 and 1990). 1.03 × 105 t, respectively, with 98% in the form of pure phenol (Environment Canada 1997). Phenols are a major Monohydric phenols such as phenol, o-, m- and p-cresol by-product of the pulp and paper, mineral (nonmetallic), and xylenols (2,3-, 2,4-, 2,5-, 2,6-, 3.4-, and 3,5- xylenol) chemical, steel and metal, and petroleum industries and dihydric phenols such as the derivatives of catechol, (Environment Canada 1997).
    [Show full text]
  • Ni-DOPED Cu-BTC for DIRECT HYDROXYLATION of BENZENE to PHENOL”
    1 UNIVERSIDAD DE INVESTIGACIÓN DE TECNOLOGÍA EXPERIMENTAL YACHAY School of Chemical Sciences and Engineering TITTLE: “Ni-DOPED Cu-BTC FOR DIRECT HYDROXYLATION OF BENZENE TO PHENOL”. Trabajo de integración curricular presentado como requisito para la obtención del título de Ingeniero en Polímeros Author: Zenteno Sanchez Jeremee Paul Advisor: PhD Terencio Thibault Urcuquí, September 2019 2 3 4 5 6 Acknowledgments For god, family, and friends. For my family that has always been there to support me every day especially my mother who believes and supports me in the good and bad moments. For my friends and the special people who are an excellent company through these years and the good moments that I shared with them. For all the teachers that teach me in every class, especially Thibault Terencio excellent mentor that support and guiding me throughout the last year of this project. For all of them, thank you so much. 7 Abstract Metal Organic Frameworks (MOFs) are novel materials with vast applications such as catalysis, dye adsorption, drug retention, or gas storage.1 MOFs can retain molecules inside their microporosity or onto its surface due to its 3D structure. One of the main advantages of the MOFs is the chemical diversity present at their surface because they consist of an organic ligand and a metal center. In this case, Copper (II) acts as the metal center and benzene-1, 3, 5 tricarboxylic acid BTC as the organic ligand, to form HKUST-1 (also known as Cu-BTC or MOF-199). Despite the diversity of existing inorganic and organic parts, each MOF usually contains only one type of transition metal.
    [Show full text]
  • Presidential Green Chemistry Challenge Awards Program Summary of 1998 Award Entries and Recipients
    awrd98final.qxd 8/24/99 1:13 PM Page a United States Pollution Prevention and EPA744-R-98-001 Environmental Protection Toxics (7406) November 1998 Agency www.epa.gov/greenchemistry 1EPA The Presidential Green Chemistry Challenge Awards Program Summary of 1998 Award Entries and Recipients 2 Printed on paper that contains at least 20 percent postconsumer fiber. awrd98final.qxd 8/24/99 1:13 PM Page i The Presidential Green Chemistry Challenge Awards Program Contents Summary of 1998 Award Entries and Recipients . 1 Awards . 2 Academic Awards . 2 Small Business Award . 4 Alternative Synthetic Pathways Award . 5 Alternative Solvents/Reaction Conditions Award . 6 Designing Safer Chemicals Award . 7 Entries From Academia . 8 Entries From Small Businesses . 27 Entries From Industry and Government . 38 Index . 70 i awrd98final.qxd 8/24/99 1:13 PM Page ii ii awrd98final.qxd 8/24/99 1:13 PM Page 1 The Presidential Green Chemistry Challenge Awards Program Summary of 1998 Award Entries and Recipients President Clinton announced the Green Chemistry Challenge on March 16, 1995, as one of his Reinventing Environmental Regulations Initiatives. According to President Clinton, the Green Chemistry Challenge was established to “promote pollution prevention and indus- trial ecology through a new U.S. Environmental Protection Agency (EPA) Design for the Environment partnership with the chemical industry.” More specifically, the program was established to recognize and support fundamental and innovative chemical methodolo- gies that are useful to industry and that accomplish pollution prevention through source reduction. EPA Administrator Carol Browner announced the Green Chemistry Challenge Awards Program on October 30, 1995.
    [Show full text]
  • Acetone from Singapore and Spain
    CONTENTS Page Determinations .............................................................................................................................. 1 Views of the Commission ............................................................................................................... 3 Part I: Introduction .............................................................................................................. I-1 Background ................................................................................................................................ I-1 Statutory criteria ....................................................................................................................... I-2 Organization of report ............................................................................................................... I-3 Market summary ....................................................................................................................... I-3 Summary data and data sources ............................................................................................... I-4 Previous and related investigations .......................................................................................... I-4 Nature and extent of sales at LTFV ........................................................................................... I-5 Sales at LTFV .......................................................................................................................... I-5 The subject merchandise .........................................................................................................
    [Show full text]
  • Page 1-21.FH10
    CHAPTER I GENERAL INTRODUCTION CHAPTER I GENERAL INTRODUCTION 1.1 Alkylation Reactions of Aromatic Hydrocarbons: The importance of alkylation in organic preparations was realized as early as 1877 with the reaction of benzene and amyl chloride, to produce amyl benzene, by Charles Friedel and James Mason Crafts-^. This was apparently the first typical alkylation reaction and came to be known as the Friedel-Crafts alkylation reaction. Friedel-Crafts reactions now find a number of industrial applications such as m the manufacture of high octane gasoline, synthetic rubber, plastics, synthetic fibers, synthetic detergents etc. Besides its commercial importance, the area of organic chemistry dealing with this reaction encompasses classic examples of some of the most interesting aspects of modern organic chemistry: electrophilic aromatic substitution, carbocation formation and rearrangement. In the Friedel-Crafts reaction, the alkylating or acylating agent and the catalyst, such as aluminium chloride and hydrogen chloride, react to form either carbonium or acylium ion or complex. The ion or complex then attacks the aromatic ring^. Thus in the alkylation of olefins in the presence of the catalyst, the following reactions take place. R-CH=CHo+ AICI^ + HCI R-CH-CH3AlC I4 CH-CH3 r -1- + R-CH-CH3AICI4 AlCl ^ +AICI4 + HCl The aromatic ring to which the olefin gets attached may be that of benzene, substituted benzene or more complicated ring systems like naphthalene or anthracene. Friedel-Crafts reactions are complicated by the rearrangement of the attacking agent and in some cases of the aromatic starting materials . There is a tendency for a carbonium ion formed during the reaction, to rearrange to a stable secondary or tertiary carbonium ion.
    [Show full text]
  • Formation of Highly Oxygenated Low-Volatility Products from Cresol Oxidation Rebecca H
    Atmos. Chem. Phys. Discuss., doi:10.5194/acp-2016-887, 2016 Manuscript under review for journal Atmos. Chem. Phys. Published: 10 October 2016 c Author(s) 2016. CC-BY 3.0 License. Formation of Highly Oxygenated Low-Volatility Products from Cresol Oxidation Rebecca H. Schwantes1, Katherine A. Schilling2,4, Renee C. McVay2,5, Hanna Lignell2,6, Matthew M. Coggon2,5, Xuan Zhang1,7, Paul O. Wennberg1,3, and John H. Seinfeld2,3 1Division of Geological and Planetary Sciences, California Institute of Technology, Pasadena, California 91125, United States 2Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States 3Division of Engineering and Applied Science, California Institute of Technology, Pasadena, California 91125, United States 4Current Affiliation: Chemistry and Firearms Branch, US Army Criminal Investigation Laboratory, Forest Park, Georgia, United States 5Current Affiliation: Cooperative Institute for Research in Environmental Science and National Oceanic and Atmospheric Administration, Boulder, Colorado, United States. 6Current Affiliation: South Coast Air Quality Management District, Diamond Bar, California, United States 7Current Affiliation: Aerodyne Research, Billerica, Massachusetts, United States. Correspondence to: Rebecca H. Schwantes ([email protected]) Abstract. Hydroxyl radical (OH) oxidation of toluene produces the ring-retaining products cresol and benzaldehyde, and the ring-opening products bicyclic intermediate compounds and epoxides. Here, first- and later-generation OH oxidation prod- ucts from cresol and benzaldehyde are identified in laboratory chamber experiments. For benzaldehyde, first-generation ring- retaining products are identified, but later-generation products are not detected. For cresol, low-volatility (saturation mass 4 3 3 5 concentration, C* 3.5 x 10 - 7.7 x 10− µg m− ) first- and later-generation ring-retaining products are identified.
    [Show full text]
  • Immediate Hydroxylation of Arenes to Phenols Via V-Containing All-Silica ZSM-22 Zeolite Triggered Non-Radical Mechanism
    ARTICLE DOI: 10.1038/s41467-018-05351-w OPEN Immediate hydroxylation of arenes to phenols via V-containing all-silica ZSM-22 zeolite triggered non-radical mechanism Yu Zhou1, Zhipan Ma1, Junjie Tang1, Ning Yan 2, Yonghua Du 3, Shibo Xi3, Kai Wang1, Wei Zhang1, Haimeng Wen1 & Jun Wang1 – 1234567890():,; Hydroxylation of arenes via activation of aromatic Csp2 H bond has attracted great attention for decades but remains a huge challenge. Herein, we achieve the ring hydroxylation of various arenes with stoichiometric hydrogen peroxide (H2O2) into the corresponding phenols on a robust heterogeneous catalyst series of V–Si–ZSM-22 (TON type vanadium silicalite zeolites) that is straightforward synthesized from an unusual ionic liquid involved dry-gel- conversion route. For benzene hydroxylation, the phenol yield is 30.8% (selectivity >99%). Ring hydroxylation of mono-/di-alkylbenzenes and halogenated aromatic hydrocarbons cause the yields up to 26.2% and selectivities above 90%. The reaction is completed within 30 s, the fastest occasion so far, resulting in ultra-high turnover frequencies (TOFs). Sys- tematic characterization including 51V NMR and X-ray absorption fine structure (XAFS) analyses suggest that such high activity associates with the unique non-radical hydroxylation mechanism arising from the in situ created diperoxo V(IV) state. 1 State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University (former Nanjing University of Technology), Nanjing 210009, P.R. China. 2 Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117585, Singapore. 3 Institute of Chemical and Engineering Sciences, 1 Pesek Road, Jurong Island, Singapore 627833, Singapore.
    [Show full text]
  • Process for Preparing Phenol and Acetone from Cumene
    Patentamt JEuropSischesEuropean Patent Office (5) Publication number: 0 164 568 Office europeen des brevets A1 EUROPEAN PATENT APPLICATION @ Application number: 85105584.8 © mt.ci.4: C 07 C 45/53 C 07 C 37/08, C 07 C 27/00 © Date of filing: 07.05.85 C 07 C 39/04, C 07 C 49/08 (S3) Priority: 24.05.84 US 614124 © Applicant: GENERAL ELECTRIC COMPANY 1 River Road Schenectady New York 12305(US) © Date of publication of application: 18.12.85 Bulletin 85/51 @ Inventor: Fulmer, John William 78 Park Ridge Drive © Designated Contracting States: Mfc Vernon Indiana 47620IUS) DE FR GB rr © Representative: Catherine, Alain General Electric - Deutschland Munich Patent Operations Frauenstrasse 32 D-8000Munchen5(DE) @ Process for preparing phenol and acetone from cumene. Benzene, toluene and ethylbenzene is removed from the heavy residues of a phenol distillation in a phenol and ace- tone from cumene process. r- DO S BACKGROUND OF THE INVENTION Phenol is a basic commodity chemical with many end uses. Most of the phenol manufactured is prepared from isopropyl benzene, hereafter referred to as cumene. The reaction sequence is short and entails the follow- ing steps: 1. Air oxidation of cumene to give cumene hydro- peroxide. 2. Acid cleavage of the hydroperoxide to provide phenol and acetone. The phenol and acetone are separated and each one purified to the degree necessary to satisfy its ulti- mate use. As is readily observed, for every mole of phenol that is produced, a mole of acetone is also theoretically produced. Acetone is also a commodity chemical with various end uses.
    [Show full text]
  • Phenol/Acetone/Cumene December 2015 Report Contents
    Phenol/Acetone/Cumene December 2015 Report Contents Phenol/Acetone/Cumene Table of Contents A Report by NexantThinking™ Process Evaluation/Research Planning (PERP) Program PERP Report 2015-6 – Published December 2015 www.nexantthinking.com Section Page 1 Executive Summary ............................................................................................................... 1 1.1 INDUSTRY OVERVIEW AND TECHNOLOGY LICENSORS ................................... 1 1.2 BUSINESS AND STRATEGIC ANALYSIS REVIEW ................................................ 2 1.3 COMMERCIAL PRODUCTION TECHNOLOGIES ................................................... 4 Cumene Consumption.................................................................................. 4 Selection of Phenol Technologies by Customers for Grassroots and Retrofitting Projects ...................................................................................... 6 1.4 ALTERNATIVE AND “DEVELOPING” TECHNOLOGIES ........................................ 7 SBB to Phenol Process ................................................................................ 7 Benzene Oxidation (with Nitrous Oxide) to Phenol Process ........................ 7 Green Technology Developments ................................................................ 8 1.5 PROCESS ECONOMICS.......................................................................................... 9 Sensitivity Analyses ...................................................................................... 10 Concluding Remarks ...................................................................................
    [Show full text]
  • Phenol and Cumene Process Summary
    IHS Chemical Process Economics Program Review 2013-11 Phenol and Cumene Process Summary By Girish Ballal December 2013 ihs.com/chemical IHS Chemical Process Economics Program | Review 2013-11 IHS Chemical agrees to assign professionally qualified personnel to the preparation of the Process Economics Program’s reports and will perform the work in conformance with generally accepted professional standards. No other warranties expressed or implied are made. Because the reports are of an advisory nature, neither IHS Chemical nor its employees will assume any liability for the special or consequential damages arising from the Client’s use of the results contained in the reports. The Client agrees to indemnify, defend, and hold IHS Chemical, its officers, and employees harmless from any liability to any third party resulting directly or indirectly from the Client’s use of the reports or other deliverables produced by IHS Chemical pursuant to this agreement. For detailed marketing data and information, the reader is referred to one of the IHS Chemical programs specializing in marketing research. THE IHS CHEMICAL ECONOMICS HANDBOOK Program covers most major chemicals and chemical products produced throughout the world. In addition the IHS DIRECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by company, product, and plant for the United States, Europe, East Asia, China, India, South & Central America, the Middle East & Africa, Canada, and Mexico. December 2013 © 2013 IHS IHS Chemical Process Economics Program | Review 2013-11 PEP Review 2013-11 Phenol and Cumene Process Summary By Girish Ballal December 2013 Abstract Phenol is an important chemical intermediate, which is mostly consumed in the production of phenolic resins and polycarbonates via bisphenol A.
    [Show full text]
  • United States Patent (19) 11) Patent Number: 5,015,786 Araki Et Al
    United States Patent (19) 11) Patent Number: 5,015,786 Araki et al. 45 Date of Patent: May 14, 1991 54 PREPARATION OF CUMENE THROUGH 4,267,380 5/1981 Austin et al. ........................ 568/385 ALKYLATION OF ANAROMATIC 4,268,454 5/1981 Pez et al. ............................. 568/880 4,567,304 l/1986 Fulmer ................................ 568/385 COMPOUND AND PREPARATION OF 4,783,559 11/1988 Matsushita et al.................. 568/862 PHENOL THROUGH CUMENE 4,877,909 10/1989 Mizusaki et al. .................... 568/880 75) Inventors: Shintaro Araki, Ichihara; Fujihisa Matsunaga, Wakayama; Hiroshi FOREIGN PATENT DOCUMENTS Fukuhara, Ichihara, all of Japan O164568 12/1985 European Pat. Off. ............ 568/385 0025653 5/1974 Japan ................................... 568/385 73) Assignee: Mitsui Petrochemical Industries Inc., 0073796 6/1980 Japan ................................... 568/385 Tokyo, Japan Primary Examiner-Werren B. Lone 21 Appl. No.: 441,477 Attorney, Agent, or Firm-Nixon & Vanderhye 22 Filed: Nov. 27, 1989 57 ABSTRACT (30) Foreign Application Priority Data In a first form, a process is provided for preparing phe nol by converting acetone by-produced by the cumene Nov. 28, 1988 (JP) Japan ................................ 63-300300 process into isopropanol, and alkylating benzene with Nov. 30, 1988 JP Japan ...... ... 63-302617 the isopropanol and optional propylene, thereby form Dec. 12, 1988 (JP) Japan ................................ 63-328722 ing phenol without acetone by-product. And cumene is 51) Int. Cl. ....................... C07C37/07; CO7C39/04 prepared by alkylating benzene in the presence of a 52 U.S. C. .................................... 568/798; 568/362; zeolite catalyst using isopropanol or a mixture of isopro 568/385; 568/754; 568/768; 568/862; 585/446 panol and propylene as an alkylating agent.
    [Show full text]