cumene hydroperoxide to phenol mechanism

It first overviews the cumene route, followed by a detailed description of the thermal decomposition behavior of CHP, and finally the mechanism of the liquid phase oxidation of cumene. Following the procedures of Example 1, the cogeneration of phenol plus acetone has been demonstrated using a series of heteropoly acid catalysts and sulfonic acid resins. Continuous generation of phenol/acetone in a plug flow reactor at LHSV's of 1-10 have been demonstrated. They are known as carbolic acids. The data show almost quantitative conversion of cumyl hydroperoxide over the full range of conditions evaluated in this work. 203-632-A describes a catalyst for decomposition of cumene hydroperoxide to produce phenol and acetone comprising zeolite crystals containing boron and aluminum bonded with silica. In the recent past, the focus of new developments was on alternative phenol processes that overcome the disadvantage of the coupled product acetone in the cumene oxidation process. Learn about our remote access options, INEOS Phenol GmbH, Technology Department, Dechenstrasse 3, 45966 Gladbeck, Germany, University of Wisconsin‐Madison, Department of Chemistry, 1101 University Avenue, Madison, WI 53706 United States, DSM Ahead R&D bv, Innovative Synthesis, P.O. Jianchu Ye, Jun Li, Yong Sha, Yale Xu, and Daowei Zhou . (3) Both the heteropoly acid and resin-type catalysts, convert much of the 2-phenyl-2-propanol in the cumene hydroperoxide feed (See Example I) into phenol/acetone. Assignors: HUNTSMAN CORPORATION (FORMERLY TEXACO CHEMICAL COMPANY), Assignors: HUNTSMAN CORPORATION ( FORMERLY TEXACO CHEMICAL COMPANY ). Minor by-products include alpha-methylstyrene; cumene, acetophenone and 2-phenylpropanol and are present in the cumene hydroperoxide feed and are apparently remaining to some extent in the mix during peroxide decomposition. (b) A substantial portion of the 2-phenyl-2-propanol in the feed is also converted to product. 261,818, and 261,819. to yield phenol and acetone. Box 1066, BB Geleen, 6160 The Netherlands. Continuous generation of phenol/acetone in a plug flow reactor at LHSV's of 1-10 have been demonstrated, for example, with AMBERLYST® XN-1010 resin, and with 12-molybdophosphoric acid-on-titania. Eurotecnica Development & Licensing S.P.A. TEXACO CHEMICAL COMPANY, 2000 WESTCHESTER AVENUE, ASSIGNMENT OF ASSIGNORS INTEREST. Assigned to HUNTSMAN PETROCHEMCIAL CORPORATION, Assignors: HUNTSMAN PETROCHEMICAL CORPORATION. 2,889,368 to Hiratsuka there is a process discussed for the decomposition of various organic hydroperoxide substances, such as, for example, cumene hydroperoxide. Politekh. Catalytic method of producing alkyl mercaptans by adding hydrogen sulphide to an olefin, Method for the production of alpha,beta-unsaturated ketones, Co-production of phenol, acetone, alpha-methylstyrene and propylene oxide, and catalyst therefor, Proton-catalysed reactions catalysed by hydrogen ion-exchanged layered clays, Proton-catalysed reactions in which water is not a stoichiometer reactant catalysed by metal cation- exchanged layered clays, Process for alkylating the ortho-position of phenol compounds, Catalytic decomposition of impurities in tertiary butyl alcohol, Process for the preparation of 1,3-propanediol, Process for producing carbonyl & hydroxy compound, Process for the preparation of phenol and acetone, A process for the preparation of a hydrocarbon mixture, and hydrocarbon mixtures so prepared, Two-stage process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal, Process for Oxidizing Alkylaromatic Compounds, Process for the hydroxylation of aromatic hydrocarbons, Lapse for failure to pay maintenance fees, Expired due to failure to pay maintenance fee, Information on status: patent discontinuation. Preferably the heteroatoms are phosphorus or silicon. Working off-campus? SECURITY AGREEMENT;ASSIGNOR:HUNTSMAN PETROCHEMICAL CORPORATION;REEL/FRAME:008209/0244, Free format text: (2) Other acidic catalysts such as phosphoric acid-on-titania and boric acid, prepared by methods similar to that of Example A, are far less effective for cumene hydroperoxide conversion to phenol/acetone (Examples 13 and 14). The above Cumene Process accounts for 80% of the total world production of phenol. Another way to prevent getting this page in the future is to use Privacy Pass. Abstracts 107:197676g (1987). Improved method and catalyst for hydrogenation of aldehydes. Upon further treatment of cumene hydroperoxide with dilute acid, phenols are obtained. Samples of crude liquid product effluent were collected and analyzed. 4,246,203 a hydroperoxide of an aromatic compound is converted to a volatile phenol and a carbonyl compound in a cleavage decomposition reaction. Step 2. 3,947,332 (1976)]. HUNTSMAN PETROCHEMCIAL CORPORATION, UTAH, Free format text: See Stozhkova, G. A., et al. Typically, phenol is generated continuously in up to ca. In the preparation of a tungstophosphoric acid-on-titania catalyst, on the other hand, the tungsten content may be 1-30 wt %. Said cumene hydroperoxide is generally diluted with inert solvent, or product, prior to being fed to the decomposer. (d) Cumene hydroperoxide conversion is essentially quantitative at the lower operating temperature (60° C.). If you are at an office or shared network, you can ask the network administrator to run a scan across the network looking for misconfigured or infected devices. Molybdenum, vanadium and titanium catalysts have also been used for the catalytic decomposition of cumyl hydroperoxide to yield mainly phenol and acetone. Employing the reactor and procedures of Example 15, 150 cc of 12-molybdophosphoric acid-on-titania were pretreated with acetone (150 cc/hr) at 60° C., then fed a mixture of "80%" cumene hydroperoxide (900 g, composition as in Example 1) diluted with acetone/cumene/phenol (6.4:2.4:9.1 weight ratio 0.2100 g) at a feed rate of 150 cc/hr. In the first embodiment heterogeneous catalysts comprise heteropoly acids, such as tungstophosphoric, molybdophosphoric, tungstosilicic and molybdosilicic, supported on titania. Another embodiment comprises the use of particular ion exchange resins having a sulfonic acid functionality. The reaction may be carried out in either a stirred slurry reactor or in a fixed bed continuous flow reactor. Hence, phenols prepared by … Lewis acid catalysts were employed in the invention of U.S. Pat. Mechanism of Acid-Catalyzed Decomposition of Dicumyl Peroxide in Dodecane: Intermediacy of Cumene Hydroperoxide. In all cases the catalyst concentration should be sufficient to provide the desired catalytic effect. Assignors: KNIFTON, JOHN F., SANDERSON, JOHN R. Assigned to UNITED STATES TRUST COMPANY OF NEW YORK (AS COLLATERAL AGENT), UNITED STATES TRUST COMPANY OF NEW YORK (AS COLLATERAL AGENT). The method of claim 3 wherein the wt % concentration of polyatom in the formulated catalyst is in the range of 0.1 to 30 wt %. The method of claim 1 wherein the heteropoly acid is 12-tungstophosphoric acid, the support is titanium dioxide and the tungsten content in the formulated catalyst is in the range of 1 to 30 wt %. alumina, silica (silicon dioxide), titania (titanium dioxide) and zirconia, as well as combinations thereof. A decomposition catalyst of sulfur dioxide or sulfuric acid is also used in U.S. Pat. The main research on the cumene oxidation process is process intensification by improving the oxidation reaction and improved process and reactor design. Completing the CAPTCHA proves you are a human and gives you temporary access to the web property. 4,209,465, also to Austin et al, it was found that cumene hydroperoxide could be decomposed to phenol and acetone using an isolable carbonium, tropylium or oxonium salt, such as triphenylcarbonium tetrafluoroborate, as the catalyst. See Izv. Phenol yields, based on hydroperoxide charged, are >99 mole %. Today, the disadvantages of using soluble strong acid catalysts in this application include (a) the need for an efficient means of separating the phenol/acetone products from the acid or spent acid catalyst, (b) the need to neutralize said acids with caustic etc., (c) the disposal of salts generated as a result of said neutralization, and (d) the difficulty in obtaining >99.9% purity phenol from such a process if there is any entrainment or contamination of the crude phenol/acetone product by said acid catalyst. ;ASSIGNORS:KNIFTON, JOHN F.;SANDERSON, JOHN R.;REEL/FRAME:004962/0894, Owner name: The mixture is heated to reflux (57° C.) with stirring, and 40.0 g of 80% cumene hydroperoxide solutiona added dropwise at a rate such that the pot temperature did not exceed 80° C. After the peroxide addition was complete, the mixture was heated to reflux for an additional 2 hours. Migration of the phenyl group to form a carbocation. 60 wt % concentration in the crude product liquid effluent, and likewise, acetone may be generated in 40 wt % concentrations. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). These include the gel type or macroreticular ion exchange resin with sulfonic acid (--SO3 H), or substituted sulfonic acid functional groups, wherein the sulfonic acid functional group is bonded directly or indirectly to an organic, preferably polystyrene or styrene-divinylbenzene polymer backbone. Sample #18: Cumene hydroperoxide conversion was essentially complete. Where the heteropoly acid is, for example, 12-molybdophosphoric acid, supported on titania, a suitable quantity of molybdenum is 1-10 wt %. • Akad. No. Expert Answer . selective catalysts. 1. 5. 11. and you may need to create a new Wiley Online Library account. A method is disclosed for the synthesis of phenol and acetone by decomposition over a heterogeneous catalyst from the group consisting of a heteropoly acid on an inert support or an ion exchange resin with a sulfonic acid functionality.

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