A charge of 100 ml. Hydrogen diffusivity enhancement in alumina pellets due to impregnated palladium. 11. Additionally, we believe that this substantial absence of undesired oxidation by-products of the olefin is, at least in part, a result of the use of a stoichiometric excess of the olefin during the second stage reaction. A method of converting ethylbenzene to styrene at high selectivity in accordance with claim 2 in which the solution of ethylbenzene hydroperoxide and ethylbenzene contains between about 5 and about 50 weight percent ethylbenzene hydroperoxide. of ten percent aqueous tetraethylammonium hydroxide was placed in a 300 ml. Owner name: The liquid reaction product contains 1-phenylethanol and acetophenone resulting from both the first stage oxidation reaction and the second stage decomposition reaction, ethylene or propylene glycol, the polar solvent, ethylbenzene, tetraalkylammonium hydroxide, osmium tetroxide and water, if added. of 0.5 percent osmium tetroxide (0.1 mmol) in t-butanol was pressured into the reactor in a stream of ethylene. 8. in-pct-2002-0415-che abstract-duplicate.pdf, in-pct-2002-0415-che claims-duplicate.pdf, in-pct-2002-0415-che correspondence-others.pdf, in-pct-2002-0415-che correspondence-po.pdf, in-pct-2002-0415-che description (complete)-duplicate.pdf, in-pct-2002-0415-che description (complete).pdf, in-pct-2002-0415-che drawings-duplicate.pdf. Since ethylbenzene hydroperoxide is not significantly soluble in water, a nonaqueous reaction medium is used to obtain the homogeneous reaction system. The stirrer was started and the reactor was heated to 135Â° C. for three hours. A 100 g. solution containing 33 percent acetophenone and 67 percent 1-phenylethanol, recovered as the bottoms after the distillative separation from ethylbenzene and ethylene glycol, is converted to styrene. The present process provides a method for the efficient production of styrene from ethylbenzene at significantly lower capital requirements and reduced operating costs. A sample of ethylbenzene hydroperoxide was purified as described in Example 3. Mathematical simulation of catalytic dehydrogenation of ethylbenzene to styrene in a composite palladium membrane reactor. The maximum amount of barium oxide needed to obtain the desired catalytic effect is about 0.15 weight percent with a maximum amount of about 0.1 percent being preferred. Any suitable source of molecular oxygen, such as air or pure oxygen, can be used. Nabeel S. Abo-Ghander, Filip Logist, John R. Grace, Jan F.M. This base is used in an amount between about 0.1 and about five weight percent of the reaction solution but it is preferred to use it within the range of about 0.2 to about two weight percent of the reaction solution, which amount provides a pH of about 14 in the solution. A process is described for the dehydrogenation of ethylbenzene lo styrene in a fluid - bed reactor-regenerator system, which uses a catalyst based on iron oxide supported on a modified alumina and promoted with further metal oxides. Analysis of the product mixture showed a conversion of 13.7 percent and a concentration of 11.4 percent ethylbenzene hydroperoxide, 8.2 percent acetophenone and 6.0 percent 1-phenylethanol. Suitable hydrogenation catalysts include copper chromite, nickel or cobalt on kieselguhr, and the like, and the hydrogenation temperatures will generally range from about 150Â° to about 200Â° C. The resulting 1-phenylethanol can be added to the stream of 1-phenylethanol and acetophenone fed to the dehydration reactor. The reaction is endothermic, nonequimolar and reversible, so high temperatures and low pressures are conducive to high conversion in the adiabatic vapor-phase reactors. If you do not receive an email within 10 minutes, your email address may not be registered, It is to be understood that the above disclosure is by way of specific example and that numerous modifications and variations are available to those of ordinary skill in the art without departing from the true spirit and scope of the invention. osmium. In this procedure ethylbenzene is placed in a reactor, preferably with between about 0.5 percent to above five weight percent of a hydroperoxide as a reaction initiator. A 14 g. (100 mmols) sample of 1-decene, 200 ml. The useful tetraalkylammonium hydroxides include those containing lower alkyl groups having from one to about five carbon atoms such as tetramethylammonium hydroxide, tetra-n-butylammonium hydroxide, and the like. When pure ethylbenzene hydroperoxide was pyrolyzed in the gas-liquid chromatograph, the analysis showed 56 percent acetophenone, 21 percent 1-phenylethanol with the balance assumed to be oxygen and water which were not determined. Shell Internationale Research Maatschappij B.V. Arizona Board Of Regents, A Body Corporate Of The State Of Arizona, Acting For And On Behalf Of Arizona State University, CHEVRON RESEARCH COMPANY, SAN FRANCISCO, CA. In the experiment 100 ml. The pressure is not critical, rather it determines the amount that dissolves in the reaction solution. The effluent of the reactor was analyzed on-line using two GCs. Also present as a solvent is the unoxidized ethylbenzene present as the predominant component in the ethylbenzene hydroperoxide solution. Propylene (10 g.) was introduced into the reactor from a charge tube. A method of converting ethylbenzene to styrene at high selectivitity in accordance with claim 5 in which the solution contains between about 0.01 and about 10 mmols of osmium tetroxide per 100 ml. The amount of polar solvent can be between about 30 and about 98 weight percent of the reaction mixture, but will preferably comprise between about 50 and 80 percent of the reaction mixture. Since the acetophenone and 1-phenylethanol coproduced in the first stage are ultimately converted to styrene, the overall selectivity of this first stage is essentially 100 percent. The reaction of ethylbenzene hydroperoxide with the olefin is preferably carried out with a stoichiometric excess, more preferably at least a 25 percent excess, of the olefin to substantially completely react all of the ethylbenzene hydroperoxide. (68.9 kPa) but a partial pressure of oxygen as low as about 5 psia. 2. The conversion of 1-phenylethanol is 96 percent and the selectivity to styrene is 98 percent. After adding 59 g. of the purified 26.5 percent ethylbenzene hydroperoxide to the chilled solution, the reactor was sealed. Ethylbenzene hydroperoxide was purified of 1-phenylethanol and acetophenone in order to accurately determine the amount of 1-phenylethanol and acetophenone that is produced in its decomposition. A very high temperature of about 600Â° C. is required for this endothermic reaction involving large quantities of high temperature steam. (344 kPa). Modeling and sensitivity analysis of styrene monomer production process and investigation of catalyst behavior. In such process, fresh and recycled liquid ethylbenzene streams are combined and heated from 25°C to 500°C in a heater 1, and the heated ethylbenzene is mixed with steam (vaporized water, w) at 700°C in mixer 2 to get the feed to the reactor at 600°C. 4. Then 5 ml. This water of reaction can be used in an amount up to about twenty weight percent of the reaction solution, but generally it is used in an amount between about one and about ten percent. of the reaction solution is suitable, however, we prefer to carry out the reaction using from about 0.03 to about 0.1 mmol of catalyst per 100 ml. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, © 2020 American Institute of Chemical Engineers, Journal of Advanced Manufacturing and Processing, Environmental Progress & Sustainable Energy, I have read and accept the Wiley Online Library Terms and Conditions of Use. Chapter 14 Feasibility of the application of porous inorganic gas separation membranes in some large-scale chemical processes. Steam is mixed with the ethylbenzene (EB) fed to the reactors to lower the partial pressure of ethylbenzene and increase conversion. A method of converting ethylbenzene to styrene at high selectivity in accordance with claim 2 in the presence of between about 0.01 and about ten mmols of osmium tetroxide per 100 ml. of the reaction solution. Since these bases are conventionally supplied in aqueous solution, the water for reaction if desired can be supplied by this solution. VIA SPILAMBERTO 3/A, I-20097 SAN DONATO MILANESE. After reaching temperature, 113 g. of 20 percent (160 mmols) ethylbenzene hydroperoxide and 10 ml. conditions, i.e., temperature, feed molar ratio of steam to ethylbenzene, styrene to ethylbenzene, and hydrogen to ethylbenzene and space time. The yield of ethylbenzene hydroperoxide and the selectivity to ethylbenzene hydroperoxide can be substantially increased in this oxidation reaction for an overall increase in process efficiency by including a minute amount of powdered barium oxide in the reaction vessel. Product analysis for 1-phenylethanol and acetophenone was made by gas-liquid chromatographic analysis using a one-eighth inch I.D. 1. With this data the selectivity to acetophenone and 1-phenylethanol was determined to be 5.7 percent and 5.4 percent, respectively. glass reactor maintained in a constant temperature bath equipped with a magnetic stirrer, a gas bubbling tube and a dip tube for sampling. A small amount of a tetraalkylammonium hydroxide is also present in the reaction solution. This mixture is subjected to dehydration to convert the 1-phenylethanol to styrene. Learn more. ;ASSIGNOR:GULF RESEARCH AND DEVELOPMENT COMPANY, A CORP. OF DE. 12. The reaction can also be carried out in a semicontinuous manner by metering the reaction components into the first of one or more tank reactors in series. The second stage reaction is carried out at a moderate temperature. The amount of catalyst can also be related to the amount of osmium metal that is used. When this reaction for the decomposition of the ethylbenzene hydroperoxide is carried out under anhydrous conditions, 1-phenylethanol and acetophenone are produced in equimolar amounts. We have discovered that ethylbenzene can be converted to styrene at an overall selectivity of 85 percent or higher in a multistage process involving ethylbenzene hydroperoxide as an intermediate product, in which each step of the process operates at high selectivity. thick-walled glass reactor equipped with a thermocouple and a stirring magnet. Therefore, insuring the substantial absence of the hydroperoxide in the reaction product is a safety procedure and avoids extra processing costs. But further analysis was carried out to account for possible handling losses of the gas. Ethylbenzene/Styrene Monomer The Lummus/UOP EBOne ethylbenzene and Lummus/UOP “Classic” styrene monomer technolo-gies have earned the reputation for being the most modern, eﬃcient, and reliable processes for the production of intermediate ethylbenzene (EB) and styrene monomer (SM), respectively. The high boiling fraction was separated and analyzed by gas chromatograph which had been calibrated using pure samples of 1-phenylethanol and acetophenone.
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