Peroxide Or Peracid Utilized Patents (Class 568/803)
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Publication number: 20140296544Abstract: The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C—H bonds and one or more activated C—H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C—H bonds; oxidizing selectively one of the one or more aromatic C—H bonds in preference to the one or more activated C—H bonds; adding a hydroxyl group to the one of the one or more aromatic C—H bonds to form one or more phenols; and purifying the one or more phenols.Type: ApplicationFiled: August 14, 2013Publication date: October 2, 2014Inventors: Dionicio Siegel, Andrew M. Camelio, Anders Eliasen, Trevor C. Johnson, Abram Axelrod, Changxia Yuan
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Patent number: 8697916Abstract: The present invention provides a process for the preparation of Cu—Cr oxides by hydrothermal synthesis method using hydrazine as a reducing agent and cetyltrimethylammonium bromide as a surfactant and these oxides are very active for selective oxidation of benzene, toluene and ethylbenzene to produce phenol, benzaldehyde and acetophenone, respectively.Type: GrantFiled: September 20, 2012Date of Patent: April 15, 2014Assignee: Council of Scientific & Industrial ResearchInventors: Rajaram Bal, Bipul Sarkar, Shubhra Acharyya Shankha, Shilpi Ghosh, Chandrashekar Pendem, Kumar Jagdish
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Patent number: 8592636Abstract: The present invention relates to a process of reacting specific compounds, which are defined below with hydrogen in the presence of a structured catalyst based on sintered metal fibers (SMF) coated by a ZnO layer with Pd-nanoparticles, to reactions of these specific compounds with hydrogen in the presence of said catalyst and an organic base as well as to vitamins, carotinoids, perfume ingredients, and/or food or feed ingredients prepared by using this reaction.Type: GrantFiled: January 28, 2011Date of Patent: November 26, 2013Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Thomas Mueller, Lioubov Kiwi-Minsker, Albert Renken, Igor Iouranov
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Publication number: 20130085305Abstract: The present invention provides a process for the preparation of Cu—Cr oxides by hydrothermal synthesis method using hydrazine as a reducing agent and cetyltrimethylammonium bromide as a surfactant and these oxides are very active for selective oxidation of benzene, toluene and ethylbenzene to produce phenol, benzaldehyde and acetophenone, respectively.Type: ApplicationFiled: September 20, 2012Publication date: April 4, 2013Applicant: Council of Scientific & Industrial ResearchInventor: Council of Scientific & Industrial Research
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Publication number: 20110190543Abstract: In a process for oxidizing an alkylaromatic compound to the corresponding hydroperoxide, a feed comprising an alkylaromatic compound is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide. The contacting is conducted at a temperature of about 90° C. to about 150° C., with the cyclic imide being present in an amount between about 0.05 wt % and about 5 wt % of the alkylaromatic compound in the feed and the catalyst being substantially free of alkali metal compounds. The contacting oxidizes at least part of the alkylaromatic compound in said feed to the corresponding hydroperoxide.Type: ApplicationFiled: September 17, 2009Publication date: August 4, 2011Inventors: Jihad M. Dakka, Stephen Zushma, Jon E.R. Stanat
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Patent number: 7781622Abstract: The present invention provides a process for direct hydroxylation of aromatic hydrocarbons like benzene to phenol, toluene to cresols and anisole to methoxy phenols by using hydrogen peroxide as environmentally benign oxidant in polar solvent like acetonitrile using vanadium phthalocyanine or its derivative as a catalyst, at a temperature in the range of 25-100° C.Type: GrantFiled: October 30, 2008Date of Patent: August 24, 2010Assignee: Council of Scientific & Industrial ResearchInventors: Suman Lata Jain, Jomy K. Joseph, Sweety Singhal, Bir Sain, Ragunathan Sivakumaran, Basant Kumar
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Patent number: 7737310Abstract: A process for preparing biphenols of the general formula I by reaction of monophenols of the general formula II where the radicals R1, R2 and R3 are each, independently of one another, hydrogen, alkyl, aryl or arylalkyl having from 1 to 10 carbon atoms, in the presence of an oxidant in a reactor, wherein a) the reactor comprises no stationary internals which act as baffles, b) a total of not more than 0.6 mol of oxidant is used per one mol of monophenol, and c) the oxidant is introduced either continuously or discontinuously in a plurality of portions over a period of from 10 minutes to 24 hours, with the amount of oxidant introduced per unit time not being constant over the total period of time but instead being varied.Type: GrantFiled: April 5, 2006Date of Patent: June 15, 2010Assignee: BASF SEInventors: Michael Bartsch, Gerd Haderlein, Tobias Aechtner, Jens Scheidel, Christian Dienes, Alexander Tempel, Thorsten Hofrichter, Werner Weinle
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Patent number: 7586014Abstract: The present invention provides an improved process for the liquid phase selective hydroxylation of benzene. The process provides a direct single step selective liquid phase hydroxylation of benzene to phenol using environment friendly green oxidant, hydrogen peroxide, and vanadyl pyrophosphate as the catalyst under mild reaction conditions. The process provides benzene conversion of 30-70% and selectivity for phenol of up to 100%.Type: GrantFiled: March 11, 2008Date of Patent: September 8, 2009Assignee: Council of Scientific and Industrial ResearchInventors: Datta Arunabha, S. Sakthivel, Satyarthi Jitendra Kumar
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Publication number: 20080234524Abstract: The present invention provides an improved process for the liquid phase selective hydroxylation of benzene. The process provides a direct single step selective liquid phase hydroxylation of benzene to phenol using environment friendly green oxidant, hydrogen peroxide, and vanadyl pyrophosphate as the catalyst under mild reaction conditions. The process provides benzene conversion of 30-70% and selectivity for phenol of up to 100%.Type: ApplicationFiled: March 11, 2008Publication date: September 25, 2008Inventors: Datta Arunabha, S. Sakthivel, Satyarthi Jitendra Kumar
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Patent number: 7241908Abstract: The invention is directed to the preparation of organic or aqueous-organic hydrogen peroxide solutions by direct synthesis from a non-explosive gaseous mixture containing hydrogen and oxygen. The process is carried out in the presence of a noble metal catalyst, using a reaction medium containing a halide and a strong acid. It can be performed in a stainless steel reactor without corrosion occurring to the reactor material if, during the reaction, the surface of the stainless steel is, at no place, in permanent contact with the gaseous mixture passing through the reactor.Type: GrantFiled: May 9, 2005Date of Patent: July 10, 2007Assignee: Degussa AGInventors: Thomas Haas, Guido Stochniol, Robert Jahn
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Patent number: 7038093Abstract: The invention relates to a process for the preparation of phenol comprising the following phases: 1) preparation in continuous of phenol by means of the direct oxidation of benzene with hydrogen peroxide operating with an H2O2/benzene ratio ranging from 10 to 70%, in a three-phase reaction system comprising a first liquid phase consisting of benzene and an organic solvent, a second liquid phase consisting of water, a solid phase consisting of an activated catalyst based on titanium silicalite TS-1; 2) separation of the phenol and non-reacted benzene from the reaction mixture of the oxidation section (1), by means of fractionated distillation; 3) separation of the solvent and by-products from the mixture coming from the distillation tail (2), by means of basic extraction; 4) transformation of the by-products obtain in section (3) to phenol by means of hydrodeoxygenation with hydrogen operating in continuous, in aqueous solution, at a temperature ranging from 250 to 500° C.Type: GrantFiled: November 20, 2003Date of Patent: May 2, 2006Assignee: Polimeri Europa S.p.A.Inventors: Daniele Bianchi, Rossella Bortolo, Roberto Buzzoni, Alberto Cesana, Leonardo Dalloro, Rino D'Aloisio
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Patent number: 6943270Abstract: A cumene process of producing phenol and acetone comprises the joint oxidation of aldehydes and dimethylbenzene alcohol by aqueous hydrogen peroxide solutions in presence of 16 wt % to 94 wt % of cumene hydroperoxide by contacting of mutually insoluble phases of the organic products from a cumene oxidation stage and hydrogen peroxide containing water with optional addition of acidic catalysts in a conversion reactor for the purpose of conversion of aldehydes into organic acids and dimethylbenzene alcohol into cumene hydroperoxide and therefore significantly simplifying the process of fractionation of organic conversion products into high quality product phenol and product acetone.Type: GrantFiled: February 28, 2001Date of Patent: September 13, 2005Assignee: Illa International, LLCInventor: Vladimir Mikhailovitch Zakoshansky
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Patent number: 6843978Abstract: The present invention refers to a microporous material formed by oxygen, silicon, germanium, aluminum, boron, gallium, zirconium and/or titanium in its composition, called TIQ-6, to its catalytic applications in oxidation reactions, and to a method of the TIQ-6 material's preparation based on the synthesis of a gel with a titanium and/or zirconium content, its hydrothermal treatment under controlled conditions, and the treatment of the resulting laminar material with a solution of an organic compound containing a proton accepting group. This swollen material is subjected to a specific treatment to obtain a high external area delaminated solid. A material, METIQ-6, similar to the TIQ-6 material, but also having organic groups anchored on its surface incorporated by a post-synthesis process onto the TIQ-6 material is also claimed.Type: GrantFiled: May 24, 2002Date of Patent: January 18, 2005Assignees: Consejo Superior De Investigaciones Cientificas, Universidad Politecnica De ValenciaInventors: Avelino Corma Canós, Vicente Fornes Segui, Urbano Díaz Morales, Marcelo Eduardo Domine
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Patent number: 6828466Abstract: A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.Type: GrantFiled: July 15, 2003Date of Patent: December 7, 2004Assignee: Board of Trustees of Michigan State UniversityInventors: Robert E. Maleczka, Jr., Milton R. Smith, III, Daniel Holmes, Feng Shi
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Patent number: 6768013Abstract: A novel process for the direct oxidation of hydrogen and hydrocarbons is disclosed, where the explosion risks inherent in gas phase oxidations are substantially eliminated. Gaseous oxidation reactants are soluble in a first reaction solvent phase such as a perfluorocarbon (e.g. C8F18) and the oxidation product is preferentially soluble in a second product solvent phase such as water or a dilute acid. A solid catalyst such as palladium on alumina is then contacted with the dissolved reactants. The oxidation product such as hydrogen peroxide may be separated from the reaction solvent phase by extraction into the immiscible product solvent phase and then separated from it by distillation, thereby allowing re-use of the aqueous phase. The present invention may be carried out using a two-phase reaction system whereby both the reaction solvent and product solvent are contained within a reaction vessel into which the solid catalyst is slurried and mechanically agitated to promote the reaction.Type: GrantFiled: June 15, 2001Date of Patent: July 27, 2004Assignee: UOP LLCInventor: Peter R. Pujado
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Patent number: 6649140Abstract: A process is described for the continuous production of alcoholic or hydro-alcoholic solutions of hydrogen peroxide in a concentration ranging from 2 to 10% by weight and their direct use in oxidation processes. The process operates under high safety conditions and with a high productivity and molar selectivity towards the formation of H2O2.Type: GrantFiled: June 1, 2001Date of Patent: November 18, 2003Assignees: Eni S.p.A., Enichem S.p.A.Inventors: Giuseppe Paparatto, Franco Rivetti, Pietro Andrigo, Giordano De Alberti
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Patent number: 6531615Abstract: This invention relates to a composition comprising antimony trifluoride and silica, a method for the preparation of said composition and use of said composition as a catalyst in a process for the oxidation of cyclohexanone to &egr;-caprolactone.Type: GrantFiled: January 30, 2001Date of Patent: March 11, 2003Assignee: Solvay (Societe Anonyme)Inventors: Michael C. Rocca, Graham Carr, Arnold B. Lambert, Duncan J. MacQuarrie, James H. Clark
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Patent number: 6479711Abstract: A process for producing an aromatic hydroxy compound having hydroxyl group at the para-position with respect to a hydroxy or an alkoxy substituent group present in the aromatic ring at a high yield and at a high selectivity, using a novel and useful hydroxylation catalyst which can afford to introduce hydroxyl group directly into aromatic ring at the para-position with respect to a hydroxy or an alkoxy substituent group, by reacting at least one compound selected from the group consisting of phenols, alkoxybenzenes and derivatives of them with hydrogen peroxide in the presence of the catalyst, wherein the hydroxylation catalyst is constituted of an oleophilized crystalline titanosilicate.Type: GrantFiled: April 28, 2000Date of Patent: November 12, 2002Assignee: Mitsui Chemicals, Inc.Inventors: Toshihiro Takai, Kazuaki Matsui
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Patent number: 6410805Abstract: A method and composition are disclosed for the hydroxylation of aromatic substrates in the presence of oxygen, hydrogen, and a catalyst. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadium catalyst, and hydrogen. The method is economical, safe, and amenable to commercial scale-up.Type: GrantFiled: January 16, 2001Date of Patent: June 25, 2002Assignee: General Electric CompanyInventor: Terence Michael Barnhart
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Patent number: 6350921Abstract: Improved methods for the simultaneous production of dihydroxybenzene and dicarbinol from diisopropylbenzene are provided. These methods provide for continuous and simultaneous production of diisopropylbenzene dihydroperoxide (DHP) and diisopropylbenzene hydroxyhydroperoxide (HHP) using Karr Column extractors operated in series. A very high purity DHP-containing solution, the precursor to the dihydroxybenzene, can be produced according to the reported methods. A safe and efficient method for producing dicarbinol from HHP is also disclosed.Type: GrantFiled: February 24, 1998Date of Patent: February 26, 2002Assignee: Indspec Chemical CorporationInventors: Raj B. Durairaj, Vaughn J. Romell, Michael N. Tackie, Thomas K. Volek
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Publication number: 20020002312Abstract: A process for hydroxylating aliphatic compounds under catalytic distillation conditions to provide alcohols is provided. The aliphatic compound is contacted, in a distillation column reactor, with an oxidation catalyst and an oxidant under conditions effective to hydroxylate the aliphatic compound while maintaining at least a portion of the aliphatic compound in a liquid phase and separating the hydroxylated product from the un-reacted aliphatic compound in the distillation column reactor.Type: ApplicationFiled: April 24, 2001Publication date: January 3, 2002Inventors: Brendan Dermot Murray, David Morris Hamilton
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Patent number: 6323377Abstract: Preparation of 2,5-dichlorophenol by selectively oxidizing 1,4-dichlorobenzene using a peroxo-, hydroperoxo-, superoxo- or alkylperoxo-metal species in the presence of form or an alkanoic acid.Type: GrantFiled: September 8, 1998Date of Patent: November 27, 2001Assignee: Syngenta Participations AGInventors: Randall A. Scheuerman, Clive A. Henrick
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Publication number: 20010044559Abstract: A process for hydroxylating benzene under catalytic distillation conditions to produce hydroxylated products such as phenol is provided. The process provides for direct hydroxylation of liquid phase benzene with an oxidant and a zeolite catalyst under conditions effective to prevent coke formation on the catalyst.Type: ApplicationFiled: April 24, 2001Publication date: November 22, 2001Inventor: David Morris Hamilton
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Patent number: 6284213Abstract: The present invention relates to a catalyst consisting of a metal of the VIII group supported on acid activated carbon functionalized with sulfonic groups, a process for the synthesis of hydrogen peroxide from hydrogen and oxygen which uses said catalyst and the use of the hydrogen peroxide solution in oxidation processes catalyzed by titanium-silicalite.Type: GrantFiled: August 3, 1999Date of Patent: September 4, 2001Assignee: Enichem S.p.A.Inventors: Giuseppe Paparatto, Rino D'Aloisio, Giordano De Alberti, Piero Furlan, Vittorio Arca, Roberto Buzzoni, Laura Meda
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Patent number: 6239317Abstract: There is described a four step process for the production of halogeno-o-hydroxydiphenyl compounds having the formula in which X is —O—or —CH2—; m is 1 to 3; and n is 1 or 2; wherein in the first step, a diphenyl compound is chlorinated; in a second step the chlorinated compound is acylated in a Friedel-Crafts reaction and optionally again chlorinated after the acylation; in a third step the acyl compound is oxidised; and in a fourth step the oxidized compound is hydrolyzed. The compounds of formula (1) are useful for the protection of organic materials against microorganisms.Type: GrantFiled: February 5, 1998Date of Patent: May 29, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Surendra Umesh Kulkarni, Vadiraj Subbanna Ekkundi, Pradeep Jeevaji Nadkarni, Chandrasekhar Dayal Mudaliar, Kishore Ramachandra Nivalkar
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Patent number: 6187964Abstract: A method of producing a phenol compound comprising a step of oxidizing an aromatic aldehyde to an aryl formate and an aromatic carboxylic acid with an oxygen-containing gas, and a step of decomposing the aryl formate to the phenol compound. To facilitate the separation of the aryl formate and the unreacted aromatic aldehyde, a mixture of the aryl formate and the unreacted aromatic aldehyde is recycled to the oxidation process to concentrate the aryl formate in the oxidation mixture. Alternatively, the oxidation process is carried out in an organic solvent having substantially no ability of dissolving water to increase the conversion of the aromatic aldehyde and the selectivity of the aryl formate, thereby producing the aryl formate in a high yield.Type: GrantFiled: July 14, 1999Date of Patent: February 13, 2001Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuo Tanaka, Yukio Sakai, Yasuhiro Shoji, Takafumi Yoshimura, Masatoshi Yoshimura
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Patent number: 6180836Abstract: The invention relates to a novel one-step process for preparation of phenol by oxidation of benzene with hydrogen peroxide catalyzed by molecular sieves doped with copper ions. With proper solvent, a phenol yield around 15-35%, selectivity close to 100% and phenol/Cu TON around 100 could be achieved. These results show that the inventive process is of great economical value for further development in large scale production of phenol.Type: GrantFiled: August 17, 1999Date of Patent: January 30, 2001Assignee: National Science Council of Republic of ChinaInventors: Soofin Cheng, Berryinne Chou
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Patent number: 6156939Abstract: The invention relates to a process for the hydroxylation of aromatic hydrocarbons by direct oxidation with hydrogen peroxide. The process is carried out in the presence of a catalyst comprising:iron, administered as inorganic salt;iron ligand, consisting of carboxylic acids of ether-aromatic compounds containing nitrogen, in particular pyrazin-2-carboxylic acid and derivatives;acidifying agent, especially trifluoracetic acid, and a solvent system comprising an organic phase consisting of a substrate and acetonitrile and an aqueous phase containing the catalyst and hydrogen peroxide.Type: GrantFiled: April 4, 2000Date of Patent: December 5, 2000Assignee: Enichem S.p.A.Inventors: Rodolfo Vignola, Ezio Battistel, Daniele Bianchi, Rossella Bortolo, Roberto Tassinari
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Patent number: 6133487Abstract: An improved process is described for the synthesis of hydroxylated aromatic compounds by means of the oxidation of an aromatic substrate with hydrogen, peroxide in an organic solvent, in the presence of synthetic zeolites, wherein the improvement consists in the fact that the organic solvent is selected from compounds having general formula (I) ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4, the same or different, represent a hydrogen atom or an alkyl group with from 1 to 4 carbon atoms or from compounds having general formula (II) ##STR2## wherein R and R', the same or different, represent an alkyl radical with from 1 to 4 carbon atoms.Type: GrantFiled: October 22, 1998Date of Patent: October 17, 2000Assignee: Enichem S.p.A.Inventors: Raffaele Ungarelli, Luigi Balducci, Daniele Bianchi
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Patent number: 6118029Abstract: A batch or continuous process produces highly pure 3,3',5,5'-tetra-t-butylbiphenol suitable as a starting material for the synthesis of 4,4'-biphenol. The process for producing 3,3',5,5'-tetra-t-butylbiphenol comprises conducting an oxidation coupling of purified 2,6-di-t-butylphenol(i) or crude 2,6-di-t-butylbiphenol(ii), said crude 2,6-di-t-butylphenol being obtained by reacting isobutylene with phenol in the presence of an aluminum catalyst, and removing the aluminum catalyst. The 2,6-di-t-butylphenol is oxidatively coupled in an alkali metal catalyst mixture comprising (1) an alkali metal catalyst and alkylphenols, or (2) alkali metal catalyst, alkylphenols and phenol to produce 3,3',5,5'-tetra-t-butylbiphenol. The oxidative coupling is conducted together with 10-30% by weight of phenol and/or t-butylphenol per 100% by weight of 2,6-di-t-butylphenol in the presence of an alkali metal catalyst.Type: GrantFiled: January 30, 1998Date of Patent: September 12, 2000Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Yoichiro Isota, Kazuhiko Yao, Mikio Kawahara
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Patent number: 6080895Abstract: An improved process for producing a catechol derivative (1) useful as a intermediate of pharmaceuticals and agricultural chemicals, being shown by the following reaction scheme. The process is characterized in that formulation in the first step is carried out in the two stages, that is, the reaction is carried out in the presence of a tin catalyst at 60-85.degree. C. to a conversion of 30 to 80% and then is completed at 95-105.degree. C. to produce a salicylaldehyde derivative (3) in a high yield and a high selectivity. Thereby, the objective catechol derivative (1) can be obtained in a high yield and with a high purity. ##STR1## In the above formula, R is alkyl, cycloalkyl, aralkyl, alkoxy, halogen atom, allyl, or aryl, and R.sup.1 is a hydroxy protective group.Type: GrantFiled: June 19, 1998Date of Patent: June 27, 2000Assignee: Daiso Co., Ltd.Inventors: Yoshiro Furukawa, Keishi Takenaka
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Patent number: 6040484Abstract: The present invention relates to a process for the hydroxylation of phenolic compounds and, more particularly, to a process for the hydroxylation of phenols and phenolic ethers with hydrogen peroxide. The invention relates to a process for the hydroxylation of phenolic compounds using hydrogen peroxide, said process being characterized in that the reaction is carried out in the presence of an effective quantity of at least one rare earth or bismuth triflate.Type: GrantFiled: August 13, 1998Date of Patent: March 21, 2000Assignee: Rhodia ChimieInventors: Michel Costantini, Laurent Gilbert, Michel Spagnol
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Patent number: 5965476Abstract: The present invention relates to silica/zeolite composite materials in spherical form and the process for their preparation which occurs by the dispersion of submicronic particles of titanium silicalite, beta zeolite, or mixtures of beta zeolite with titanium silicalite, in a silica sol synthesized by acid hydrolysis of silicon alkoxides; the hybrid sol thus obtained, subjected to emulsification and gelation techniques in organic mediums, produces these materials in a spherical form with an average diameter of between 20 and 150 .mu.m and containing up to 70% by weight of titanium silicalite, beta zeolite or mixtures of titanium silicalite/beta zeolite.The materials of the invention, having a high mechanical resistance and characterized by a surface area of between 300 and 800 m.sup.2 /g, are applied as catalysts; in particular, those consisting of titanium silicalite or mixtures of titanium silicalite/beta zeolite are advantageously used in oxidation reactions of organic compounds with hydrogen peroxide.Type: GrantFiled: February 14, 1997Date of Patent: October 12, 1999Assignee: Enichem S.p.A.Inventors: Luigi Balducci, Raffaele Ungarelli, Cristina Tonini
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Patent number: 5840997Abstract: Alkoxybenzaldehydes and aryloxybenzaldehydes are converted to the corresponding phenols by reacting the benzaldehydes in an organic solvent phase with formic acid and hydrogen peroxide in an aqueous solvent phase to produce the corresponding formate ester. The formate ester is then saponified to produce the corresponding phenol.Type: GrantFiled: March 31, 1997Date of Patent: November 24, 1998Assignee: Dakota Gasification CompanyInventors: Paul D. Pansegrau, Brant P. Munson
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Patent number: 5811599Abstract: A process for the oxidation of hydrocarbons and their derivatives having the general formula RX, wherein R is from n-alkyl, iso-alkyl, benzyl, cyclohexyl, mono, di or tricyclic aryl, or alkenic groups and X is selected from H, OH or Cl to compounds having formula R.sup.1 XY wherein R.sup.1 =(R--H), X has the meaning defined as above and Y=OH; which comprises of reacting the appropriate hydrocarbon or it's derivative of the formula RX where R and X have the meaning given above, with a solution of aqueous hydrogen peroxide at a temperature in the range of 10.degree.-100.degree. C. in the presence of an amorphous titanium-silicate catalyst having molar chemical composition in terms of the anhydrous oxides of TiO.sub.2 : (5-400) SiO.sub.2, having an average micropore radius between 10 and 40 .ANG., an absorption band around 220 nm in the ultraviolet region, a band around 960 cm.sup.-1 in the infrared region, interatomic vectors around 1.6-1.7, 2.7-2.8, 4.1-4.2 and 5.0-5.2 .ANG.Type: GrantFiled: August 2, 1995Date of Patent: September 22, 1998Inventors: Keshavaraja Alive, Ramaswamy Arumugamangalam Venkataraman, Ratnasamy Paul
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Patent number: 5670465Abstract: p-Dihydroxylated aromatic compounds are prepared via the oxidation of p-fuchsones, the latter advantageously being synthesized by reacting a phenolic compound having at least one hydrogen atom in the para-position to the hydroxyl function with a non-enolizable ketonic compound, in the presence of a catalytically effective amount of an acid catalyst and, optionally, a cocatalytically effective amount of an ionizable sulfur-containing compound.Type: GrantFiled: June 5, 1995Date of Patent: September 23, 1997Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Daniel Manaut, Daniel Michelet
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Patent number: 5616734Abstract: The invention relates to the use of compounds of the formula IR.sup.1.sub.a Re.sub.b O.sub.c (I),where a is from 1 to 6, b is from 1 to 4 and c is from 1 to 14 and the sum of a, b and c is in accordance with the valence of from 5 to 7 of the rhenium, with the proviso that c is not greater than 3.multidot.b, and where R.sup.1 is identical or different and is an aliphatic hydrocarbon radical having from 1 to 10 carbon atoms, an aromatic hydrocarbon radical having from 6 to 10 carbon atoms or an arylalkyl radical having from 7 to 9 carbon atoms, with the radicals R.sup.1 being able, if desired, to be identically or differently substituted independently of one another and, in the case of .sigma.-bonded radicals, at least one hydrogen atom still being bonded to the carbon atom in the .alpha. position, as catalysts for the oxidation of electron-rich aromatic compounds and their derivatives and to a process for the oxidation of electron-rich aromatic compounds which comprises oxidizing electron-rich C.sub.6 -C.sub.Type: GrantFiled: January 25, 1995Date of Patent: April 1, 1997Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Joao D. G. Correia, Richard Fischer, Waldemar Adam, Jianhua Lin, Chantu R. Saha-Moller, Masao Shimizu
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Patent number: 5569791Abstract: Phenol is produced from a hydrocarbon feedstock using a process combination offering unexpected synergy. Benzene is produced from the hydrocarbon feedstock using a highly selective aromatization catalyst which provides substantial quantities of high-purity hydrogen. The hydrogen is converted to hydrogen peroxide, which in turn is used to convert the benzene to phenol in high yield.Type: GrantFiled: April 25, 1995Date of Patent: October 29, 1996Assignee: UOPInventors: John I. Hammerman, Peter R. Pujado
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Patent number: 5559274Abstract: Phenol is produced from a hydrocarbon feedstock using a process combination offering unexpected synergy. Benzene is produced from the hydrocarbon feedstock using a highly selective aromatization catalyst which provides substantial quantities of high-purity hydrogen. The hydrogen is converted to hydrogen peroxide, which in turn is used to convert the benzene to phenol in high yield.Type: GrantFiled: April 25, 1995Date of Patent: September 24, 1996Assignee: UOPInventors: John I. Hammerman, Peter R. Pujado
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Patent number: 5493061Abstract: This invention relates to a process for the oxidation of phenol to a mixture of hydroquinone and catechol using hydrogen peroxide as oxidant in the presence of titanium silicate molecular sieves in a multistage fixed bed reactor.Type: GrantFiled: December 9, 1994Date of Patent: February 20, 1996Assignee: Council of Scientific & Industrial ResearchInventors: Paul Ratnasamy, Subramanian Sivasanker
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Patent number: 5426244Abstract: Phenols are reacted with a hydrogen peroxide in the presence of a crystalline titanosilicate catalyst and a cyclic ether, such as dioxane, as a solvent. The method provides especially high para-selectivity compared with conventional methods, and, at the same time, provides high yields of dihydric phenols versus hydrogen peroxide.Type: GrantFiled: May 2, 1994Date of Patent: June 20, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Ryuji Sugai, Osamu Kondo, Yuki Motoyama, Shu Yoshida
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Patent number: 5414155Abstract: o-Dihydroxylated aromatic compounds, for example pyrocatechol, are selectively prepared by reacting an o-fuchsone with an oxidizing agent, for example hydrogen peroxide, optionally in the presence of a catalytically effective amount of an acid catalyst.Type: GrantFiled: January 10, 1994Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Daniel Manaut, Daniel Michelet
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Patent number: 5387724Abstract: Phenols, and related aromatic compounds, phenolic ethers, can be hydroxylated selectively using hydrogen peroxide in the presence of an amorphous or microcrystalline zirconium phosphate catalyst in a solvent containing an aliphatic carboxylic acid. The process is particularly suitable for phenol itself, and advantageously employs a partially dehydrated microcrystalline catalyst obtained by heating an hydrated microcrystalline zirconium phosphate for example at about 100.degree. C. A convenient reaction temperature is 50.degree. to 90.degree. C., and convenient solvent is acetic acid. In an improved method of producing the catalyst, zirconium phosphate is precipitated from an aqueous phosphoric acid solution of zirconium oxychloride in the presence of a cationic phase transfer agent such as an alkylpyridinium salt or tetraalkylquaternary ammonium salt or a nonionic surfactant such as an alcohol ethoxylate.Type: GrantFiled: October 12, 1993Date of Patent: February 7, 1995Assignee: Solvay Interox LimitedInventors: Alexander Johnstone, William R. Sanderson, Robert C. Wasson
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Patent number: 5364983Abstract: The present invention relates to a process for the preparation of aromatic polyhydroxy compounds, by reacting an aromatic hydroxyaldehyde with hydrogen peroxide, with or without the addition of a base, in the presence of a nitrile R--CN, in which R is an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, which is unsubstituted or substituted by one or more alkyl groups.Type: GrantFiled: October 7, 1993Date of Patent: November 15, 1994Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Heinz Strutz
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Patent number: 5364982Abstract: Hydroxylation of phenol is prone to the production of tarry by-products. Selective hydroxylation of phenol can be obtained by reacting a limited amount of hydrogen peroxide with phenol in solution in a compatible organic solvent and in the presence of a catalyst that is at least partly soluble in the reaction medium and is the salt of a heteropolyacid of general formula: i) Q.sub.3 PMo.sub.m W.sub.12-m O.sub.40 or ii) Q.sub.3+v PM.sub.n V.sub.v O.sub.40, in which Q represents a compatible organic cation, m is zero or an integer less than 6, M represents molybdenum or tungsten, v is an integer which is up to 3, and n is an integer such that n+v=12. A preferred organic cation comprises cetyl pyridinium. Selectivity towards catechol is particularly observed employing heteropolyacid salts in which m=0 in formula i) and when n=11 and M=tungsten in formula ii) and towards hydroquinone when n=11 and M=molybdenum in formula ii). Preferably the reaction medium comprises acetonitrile.Type: GrantFiled: August 3, 1993Date of Patent: November 15, 1994Assignee: Solvay Interox LimitedInventors: Scott W. Brown, Anthony Hackett, Angela M. King, Alexander Johnstone, William R. Sanderson
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Patent number: 5331103Abstract: The present invention relates to a process for monohydroxylation of phenolic compounds which allows an increase in the amount of para isomer.The invention relates to a process for monohydroxylation of a phenolic compound having a hydrogen atom in the para position to the hydroxyl group, for the purpose of obtaining a dihydroxylated aromatic compound by reacting the initial phenolic compound with hydrogen peroxide in the presence of an effective amount of a strong acid and of a ketonic compound, said process being characterized by the fact that the reaction is carried out in the presence of an effective amount of a polar aprotic organic solvent with a basicity such that it has a "donor number" below 25.Type: GrantFiled: February 26, 1993Date of Patent: July 19, 1994Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5276216Abstract: Process for oxidizing aromatic and aliphatic compounds, by using, in aqueous solution, an enzymatic system constituted by hydrogen, peroxide as the oxidizer compound, peroxidase and activated oxygen, or an enzyme which releases activated oxygen from H.sub.2 O.sub.2.In the preferred process, the enzymatic system is a double-enzyme one, in which peroxidase and catalase are used as enzymes.Type: GrantFiled: October 27, 1992Date of Patent: January 4, 1994Assignee: Ausimont S.p.A.Inventors: Ivan Wlassics, Fulvio Burzio
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Patent number: 5245086Abstract: The phenols/phenol ethers are hydroxylated by reaction with hydrogen peroxide, in the presence of a catalytically effective amount of (a) at least one alkali metal or alkaline earth metal salt of a protonic acid having a pKa in water of less than -0.1 and (b) a free protonic acid.Type: GrantFiled: December 5, 1990Date of Patent: September 14, 1993Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5233097Abstract: Certain crystalline titanoaluminosilicate molecular sieve compositions having titanium, aluminum, and silicon present as framework tetrahedral oxide units are particularly effective in hydroxylating the aromatic nucleus of aromatic compounds using hydrogen peroxide, even where the hydrogen peroxide is used at concentrations of 10 weight percent or less. The variant where the exchangeable hydrogens of the titanoaluminosilicate are replaced by an alkali or alkaline earth metal cation is particularly favored because of the concomitant increase in selectivity. Excellent utilization of hydrogen peroxide often is observed, even when the hydroxylation is effected at temperatures under about 60.degree. C.Type: GrantFiled: October 15, 1992Date of Patent: August 3, 1993Assignee: UOPInventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
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Patent number: 5160496Abstract: The phenols and phenol ethers are economically and efficiently hydroxylated using hydrogen peroxide, in the presence of a catalytically effective amount of a bridged clay, e.g., a zeolite or smectite.Type: GrantFiled: July 16, 1990Date of Patent: November 3, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Constantini, Jean-Michel Popa