Peroxy Containing Reactant Patents (Class 568/385)
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Patent number: 6225513Abstract: The present invention relates to an improved method for producing phenol and acetone by oxidizing cumene into technical cumol hydroperoxide (CHP) through catalytic cleavage of the CHP. According to the invention, the oxidation products are concentrated to up to a cumene content ranging from 21 to 30 wt % in the technical cumol hydroperoxide, said mixture being used for the catalytic cleavage.Type: GrantFiled: September 15, 1999Date of Patent: May 1, 2001Assignees: Illa International Ltd., Phenolchemie GmbH & Co. KgInventors: Vladimir Michailovitch Zakoshansky, Irina Ivanova Vasilieva, Andrei Konstantinovitch Griaznov, Youry Nikolaevitch Youriev, Heinrich Van Barnefeld, Otto Gerlich, Michael Kleine-Boymann, Werner Kleinloh, Christian Michalik
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Patent number: 6201157Abstract: An improved method for production of phenol and acetone by decomposition of cumene hydroperoxide in the presence of an acidic catalyst to phenol and acetone, wherein the improvement comprises neutralization of the acidic catalyst after substantial completion of the decomposition by addition of a substituted amine.Type: GrantFiled: January 10, 2000Date of Patent: March 13, 2001Assignee: Sunoco, Inc. (R&M)Inventor: Scott R. Keenan
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Patent number: 6169216Abstract: A process for producing phenol and acetone from cumene hydroperoxide is described in which the cumene hydroperoxide is contacted with a solid-acid catalyst comprising a sulfated transition metal oxide, preferably sulfated zirconia.Type: GrantFiled: April 22, 1999Date of Patent: January 2, 2001Assignee: Mobil Oil CorporationInventors: Doron Levin, Jose G. Santiesteban, James C. Vartuli
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Patent number: 6169215Abstract: A process for producing phenol and acetone from cumene hydroperoxide is described in which the cumene hydroperoxide is contacted with a solid-acid catalyst produced by calcining a source of a Group IVB metal oxide with a source of an oxyanion of a Group VIB metal at a temperature of at least 400°C.Type: GrantFiled: March 25, 1999Date of Patent: January 2, 2001Assignee: Mobil Oil CorporationInventors: Doron Levin, Jose G. Santiesteban, James C. Vartuli
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Patent number: 6127498Abstract: Hydrogenated fluoromodified polymers obtainable by reaction among hydrogenated polymers and the modifier having a polyether structure:RfO(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n --CF.sub.2 --A.sub.q --T.sub.p (I)wherein A is a linking bridge bound to the end group --CF.sub.2 -- of the perfluoropolyether chain, T represents one or more reactive functional groups; p and q are integers, p ranges from 1 to 4, q is an integer from 0 to 1; m and n are integers such that m/n is comprised between 0.2 and 5, Rf is a perfluoroalkyl from 1 to 3 carbon atoms.Type: GrantFiled: April 6, 1998Date of Patent: October 3, 2000Assignee: Ausimont S.p.A.Inventors: Claudio Tonelli, Giovanni Simeone, Tania Trombetta
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Patent number: 6106803Abstract: Granulates which contain titanium silicalite-1 are composed of silicon dioxide, titanium dioxide and titanium silicalite-1 crystals. The granulates can be prepared by spray-drying or spray granulating the crystallization suspension. The granulates may be used as suspension catalysts, such as for the epoxidation of olefins using hydrogen peroxide.Type: GrantFiled: July 23, 1998Date of Patent: August 22, 2000Assignee: Degussa-Huls AGInventors: Steffen Hasenzahl, Georg Markowz, Mathias Viandt, Eckehart E. Roland, Georg Thiele, Gustaaf Goor, Alexander Moller
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Patent number: 6066767Abstract: Purification of cumene hydroperoxide cleavage products from hydroxyacetone and carbonyl compounds is accomplished via extraction of hydroxyacetone and carbonyl compounds from cleavage products with a circulating water-salt solution in an extractor during an extraction stage and subsequent conversion of hydroxyacetone and other carbonyl compounds into deep condensation products in a HAC reactor operating as a plug-flow reactor or mixing reactor or as their combination. The conversion/condensation process is conducted in the water-salt solution by treating the hydroxyacetone and carbonyl compounds with alkaline agents. Various homogenous and/or heterogeneous alkaline catalysts may be used. Optionally multiple sequential extraction stages may be connected to the HAC reactor for improved performance.Type: GrantFiled: February 10, 1999Date of Patent: May 23, 2000Assignee: ILLA International, LLCInventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva
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Patent number: 6057483Abstract: Disclosed is a process for the cleavage of technical cumene hydroperoxide (CHP) into phenol, acetone and .alpha.-methylstyrene. In a first stage, the CHP cleavage process is conducted in such a way to maintain the heat generation rate and the heat removal rate balanced in each of the CHP cleavage reactors. The cleavage of the CHP is conducted under substantially isothermal conditions at a temperature in the range of 47-50.degree. C. In the second stage of the process dicumylperoxide (DCP) and dimethylbenzene alcohol (DMBA) cleavage is carried out in a multi-section plug-flow reactor under non-isothermal conditions at a controlled temperature increase. The temperature is controlled with the use of thermocouples installed in each section of the reactor. The obtained temperature profile is compared with the temperature profile required by the kinetic model based on .DELTA.T in each section of the reactor.Type: GrantFiled: September 4, 1998Date of Patent: May 2, 2000Assignee: Illa International, LLCInventors: Vladimir Mikhailovitch Zakoshansky, Andrei Konstantinovitch Griaznov, Irina Ivanovna Vassilieva
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Patent number: 6043399Abstract: The present invention lies in the field of the manufacture of phenol from cumene. The subject of the invention is a process for the continuous preparation of cumene hydroperoxide by oxidation, in the liquid phase, of cumene in the presence of oxygen. The process according to the invention is carried out in the presence of at least one agent chosen from the hydroxide or the carbonate of an alkali metal and/or alkaline-earth metal; the said agent being used in an amount of between 2 and 10 ppb (expressed as sodium hydroxide) with respect to the amount of cumene introduced. The invention likewise relates to the use of the hydroperoxide thus obtained for preparing phenol.Type: GrantFiled: February 12, 1999Date of Patent: March 28, 2000Assignee: Rhodia ChimieInventors: Joao Amadio, Brice Le Corre, Jean-Jacques Charrin, Xavier Houzard, Philippe Laurent, Roland Noyerie, Yves-Michel Quenton
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Patent number: 5756852Abstract: Process for the catalytic oxidation of a saturated hydrocarbon to obtain a ketone which involves carrying out the oxidation simultaneously with the oxidation of H.sub.2 S to form elemental sulfur and the ketone.Type: GrantFiled: October 15, 1996Date of Patent: May 26, 1998Inventor: Derek H. R. Barton
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Patent number: 5736479Abstract: The invention concerns new oxidation catalysts, methods of producing them and their use. These catalysts consist of titanium silicalites crystallized in situ onto activated charcoal or metal oxides. The titanium silicalite content lies preferably in the range of 30 to 60% by wt. The atomic ratio of Si to Ti in the carrier-borne phase is 10 to 100. Such catalysts are particularly suitable for oxidation reactions with H.sub.2 O.sub.2 under mild conditions, such as temperatures of 20.degree. to 120.degree. C. and pressures equal to or higher than atmospheric.Type: GrantFiled: May 24, 1995Date of Patent: April 7, 1998Assignee: Leuna-Katalysatoren GmbHInventors: Rainer Schodel, Peter Birke, Reinhard Geyer, Peter Kraak, Willibald Muller, Hans-Dieter Neubauer, Rolf Pester, Fritz Vogt, Klaus-Peter Wendlandt
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Patent number: 5723677Abstract: The invention comprises a method for the oxidation of alkanes to alcohols and for decomposition of hydroperoxides to alcohols utilizing new compositions of matter, which are metal complexes of porphyrins. Preferred complexes have hydrogen, haloalkyl or haloaryl groups in meso positions, two of the opposed meso atoms or groups being hydrogen or haloaryl, and two of the opposed meso atoms or groups being hydrogen or haloalkyl, but not all four of the meso atoms or groups being hydrogen. Other preferred complexes are ones in which all four of the meso positions are substituted with haloalkyl groups and the beta positions are substituted with halogen atoms. A new method of synthesizing porphyrinogens is also disclosed.Type: GrantFiled: June 27, 1996Date of Patent: March 3, 1998Assignee: Sun Company, Inc. (R&M)Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5639922Abstract: A process is described for the selective decomposition of aromatic primary hydroperoxides by contacting a hydroperoxide mixture containing aromatic primary hydroperoxides and aromatic tertiary hydroperoxides obtained by oxidation of alkylaromatic compounds under non-aqueous conditions with an alkali and an organic aromatic carboxylic acid salt.Type: GrantFiled: July 14, 1995Date of Patent: June 17, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Yoichi Ikeda, Motoo Hazama, Nobuhiro Kawara, Maki Okumura, Takanori Ito
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Patent number: 5580996Abstract: The compounds of the invention are characterised by the formulae ##STR1## wherein index p represents an integer equal to 2 or 3 and q can take the value zero or 1, with the provision that p+q=3. Said compounds are obtained from hex-3-yne-2,5-diol following a process which comprises reacting an ethylenic compound of formula(CH.sub.3).sub.2 C.dbd.C(H).sub.n (CH.sub.3).sub.m (I)wherein index n represents an integer equal to 1 or 2 and m can take the values zero or 1 and wherein n+m=2, with hex-3-yne-2,5-diol, followed by the oxidation of the acetylenic ether obtained by means of ruthenium tetroxide. The compounds of formula (III) can be used as intermediate products for the preparation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol.RTM.).Type: GrantFiled: April 13, 1995Date of Patent: December 3, 1996Assignee: Firmenich SAInventors: Hubert Mimoun, Alexander Zaslona, Jean-Paul Leresche
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Patent number: 5530166Abstract: Technical cumylhydroperoxide of a wide composition range is cleaved in circulating reactors of a shell and tube design at the same elevated pressure as dicumyl peroxide is cleaved in a plug flow reactor with a recirculation ratio of at least 26. The cleavage process is controlled using two calorimeters and controlling the absolute .DELTA.T value which is the difference in the temperature drop between the two calorimeters.Type: GrantFiled: January 13, 1995Date of Patent: June 25, 1996Assignees: General Electric Company, Illa InternationalInventors: Vladimir M. Zakoshansky, Andrei K. Griaznov
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Patent number: 5510537Abstract: A process for oxidizing silyl enone ethers to alpha, beta-unsaturated enodes having the formulas ##STR1## which comprises reacting the appropriate silyl enone ether with a radical generated by the metal catalyst decomposition of a peroxide composition.Type: GrantFiled: April 26, 1995Date of Patent: April 23, 1996Assignee: The Upjohn CompanyInventor: Paul M. Herrinton
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Patent number: 5475157Abstract: There is disclosed a process for producing an aromatic hydroxylic compound by acid decomposition of a hydroperoxide having the general formula (I) ##STR1## wherein Ar represents an aromatic hydrocarbon group having a valence of n; and n represents an integer of 1 or 2, in the presence of an acid catalyst, thereby to provide an aromatic hydroxylic compound having the general formula (II)Ar--(OH)n (II)wherein Ar and n are the same as above defined, characterized in that tetrafluoroboric acid, hexafluorosilicic acid or hexafluorophosphoric acid is used as the acid catalyst. According to this process, the aromatic hydroxylic compound is obtained in a high yield while the by-production of hydroxyacetone is effectively suppressed.Type: GrantFiled: September 2, 1994Date of Patent: December 12, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Shintaro Araki, Hiroshi Iwasaki, Hiroyasu Ohno, Isao Hashimoto, Teruaki Mukaiyama
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Patent number: 5463136Abstract: A process for the decomposition of cumene hydroperoxide to phenol, acetone, and alpha-methylstyrene is presented. In this process, cumene hydroperoxide and sulfuric acid are reacted in a reflux cooled reactor the products of which are transported under inhibited conditions to a plug flow reactor, and are reacted to produce phenol, acetone, and alpha-methylstyrene. In one embodiment of the invention, a heat exchanger is used to obtain and maintain the inhibited conditions of the transported reactor products.Type: GrantFiled: December 22, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: Robert L. Blackbourn, Edgar D. Allan, Loc B. Le, Snehal Patel
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Patent number: 5430200Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.Type: GrantFiled: September 16, 1994Date of Patent: July 4, 1995Assignee: Hercules IncorporatedInventor: Horace E. Hood
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Patent number: 5414162Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of pentagonally cross-sectioned alumina having palladium deposited thereon and is brought into contact with the catalyst in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.Type: GrantFiled: November 12, 1993Date of Patent: May 9, 1995Assignee: Texaco Chemical Inc.Inventors: John R. Sanderson, John F. Knifton
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Patent number: 5406002Abstract: An organophosphine-treated titanium-containing zeolite is a catalyst for hydrocarbon oxidation.Type: GrantFiled: February 25, 1994Date of Patent: April 11, 1995Assignee: Exxon-Chemical Patents Inc.Inventors: Luc R. M. Martens, Georges M. K. Mathys
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Patent number: 5399794Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina having gold-promoted palladium deposited thereon and is brought into contact with the catalyst in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.Type: GrantFiled: November 12, 1993Date of Patent: March 21, 1995Assignee: Texaco Chemical Inc.Inventor: John R. Sanderson
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Patent number: 5371305Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.Type: GrantFiled: December 31, 1992Date of Patent: December 6, 1994Assignee: Hercules IncorporatedInventor: Horace E. Hood
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Patent number: 5364988Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina having chromium deposited thereon and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.Type: GrantFiled: November 12, 1993Date of Patent: November 15, 1994Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Roger G. Duranleau
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Patent number: 5359130Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina having palladium and platinum deposited thereon and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.Type: GrantFiled: November 12, 1993Date of Patent: October 25, 1994Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Roger G. Duranleau, John F. Knifton
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Patent number: 5354925Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of lead oxide supported on alumina and is brought into contact with the catalyst in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.Type: GrantFiled: November 12, 1993Date of Patent: October 11, 1994Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Roger G. Duranleau
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Patent number: 5354917Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina or carbon having rhodium deposited thereon and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.Type: GrantFiled: November 12, 1993Date of Patent: October 11, 1994Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Roger G. Duranleau, John F. Knifton
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Patent number: 5304684Abstract: sec-Butylbenzene hydroperoxide obtained by oxidizing sec-butylbenzene is decomposed into phenol and methyl ethyl ketone, a resulting liquid comprising a methyl ethyl ketone as the main component is washed with an aqueous alkali solution to remove carboxylic acids, carboxylic acid esters, unsaturated ketones, and aldehydes, and the washed liquid is further subjected to neutralization, dehydration, and distillation.A methyl ethyl ketone can be obtained which has a high quality with regard to purity and potassium permanganate fading.Type: GrantFiled: July 7, 1993Date of Patent: April 19, 1994Assignee: Sumitomo Chemical Company, Ltd.Inventors: Hiroshi Nishida, Kazuo Kimura, Shouji Hamada, Masaaki Toma, Hirooki Nagaoka
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Patent number: 5298667Abstract: Any one material selected from (A) sec-butylbenzene substantially free from ethyl hydroperoxide, carboxylic acids and phenol, (B) sec-butylbenzene substantially free from styrenes and (C) sec-butylbenzene substantially free from methylbenzyl alcohol is oxidized to obtain sec-butylbenzene hydroperoxide, which is then decomposed to obtain phenol and methyl ethyl ketone.Type: GrantFiled: December 23, 1992Date of Patent: March 29, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Kiyoshi Iwanaga, Mitsuhisa Tamura, Toshio Nakayama, Masahiro Usui, Hiroyuki Umida, Hirooki Nagaoka
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Patent number: 5298665Abstract: The invention relates to a process for preparing an alkanone and/or alkanol by oxidizing an alkane with 3-30 C-atoms, using oxygen, to form an alkyl hydroperoxide, followed by a decomposition of the resulting alkyl hydroperoxide in the presence of a metal compound immobilized on a carrier, which carrier carries aliphatic or aromatic amine groups or sulphide groups. The process is preferably applied to cycloalkanes.Type: GrantFiled: March 15, 1993Date of Patent: March 29, 1994Assignee: DSM N.V.Inventors: Ludovicus H. W. Janssen, Peter Hoogendoorn, Ubaldus F. Kragten, Henricus A. C. Baur
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Patent number: 5274139Abstract: A method of effecting a reaction between oxygen and an organic substance comprising the stages of:a. forming a reaction mixture comprising an N-alkylpyrrolidinone, at least one organic substance capable of reaction with oxygen and a hydroperoxide decomposition catalytically effective amount of a transition metal oxidation catalyst under a partial pressure of oxygen of at least about 16 psig, the molar ratio of organic substance to N-alkylpyrrolidinone being at least about 1:100;b. subjecting the reaction mixture to conditions such that an oxidation reaction occurs, whereby:(1) at least a portion of the N-alkylpyrrolidinone is oxidized, in situ, to the corresponding hydroperoxide;(2) the hydroperoxide is subsequently decomposed by the catalytic action of the transition metal oxidation catalyst to the corresponding N-alkylsuccinimide, the decomposition resulting in the production of active oxygen which reacts with the organic substance;c.Type: GrantFiled: February 26, 1993Date of Patent: December 28, 1993Assignee: University of FloridaInventors: Russell S. Drago, Douglas E. Patton
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Patent number: 5254751Abstract: A method for the enhanced decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone which comprises decomposing cumene hydroperoxide in a non-isothermal manner in the presence of excess acetone whereby the molar ratio of acetone to phenol in a decomposition reactor is from about 1.1: 1 to 1.5:1.A method for the selectivity of the decomposition of dicumyl peroxide to alpha methylstyrene also phenol and acetone in the presence of an acidic catalyst which comprises carrying out the decomposition at a temperature of from about 80.degree. to 110.degree. C.A method for carrying out the decomposition of dicumyl peroxide with an acidic catalyst system which comprises performing such decomposition in the presence of the reaction product of (1) an amine with (2) an acidic material which can catalyze the decomposition of CHP.Type: GrantFiled: September 14, 1992Date of Patent: October 19, 1993Assignee: General Electric CompanyInventor: Vladimir M. Zakoshansky
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Patent number: 5252758Abstract: Process for oxidizing organic compounds with hydrogen peroxide in the presence of titanium-silicalite and of a water-alcohol solvent which, after the preliminary separation of the oxidation product and of the water formed during the reaction, is used again in order to extract hydrogen peroxide produced in a redox process with alkyl-anthraquinone and is fed again to the oxidation reaction.Type: GrantFiled: November 25, 1992Date of Patent: October 12, 1993Inventors: Mario G. Clerici, Patrizia Ingallina
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Patent number: 5245090Abstract: This invention is an improved two-stage method for producing phenol and acetone from cumene hydroperoxide (CHP) comprising decomposing cumene hydroperoxide in a first stage, and subjecting the product of the first stage to hydrogenation in a second stage; residual cumene hydroperoxide may be decomposed in the second stage, with or without recycling of acetone and/or part of the effluent of the second stage back to the first stage; cumene is also desirably recycled.Type: GrantFiled: September 11, 1992Date of Patent: September 14, 1993Assignee: Aristech Chemical CorporationInventors: Anthony J. DeCaria, Alain A. Schutz
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Patent number: 5210315Abstract: A process for producing an .alpha.-hydroxyketone represented by formula (I): ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or an alkoxycarbonyl group; and R.sup.2 and R.sup.3 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group, provided that they do not simultaneously represent a hydrogen atom; or a pair of R.sup.1 and R.sup.2, a pair of R.sup.1 and R.sup.3, or a pair of R.sup.2 and R.sup.3 is taken together to form a ring; and the pair of R.sup.1 and R.sup.2 and the pair of R.sup.2 and R.sup.3 may form a ring simultaneously, is disclosed, comprising reacting a compound represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, with an oxidizing agent in the presence of a ruthenium compound and water. .alpha.-Hydroxyketones useful as physiologically active substances are produced with good selectivity and in high yield.Type: GrantFiled: October 18, 1991Date of Patent: May 11, 1993Assignee: Takasago International CorporationInventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi
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Patent number: 5149880Abstract: Nitrogen-containing aromatic heterocyclic ligand-metal complexes and their use for the activation of hydrogen peroxide and dioxgen are disclosed. Processes whereby activated hydrogen peroxide or dioxygen are used to transform various organic substrates are also disclosed. In particular, processes for the conversion of methylenic carbons to carbonyls, for the dioxygenation of aryl olefins, acetylenes and aryl-.alpha.-diols, for the oxidation of alcohols and aldehydes and for the removal of mercaptans from gaseous streams and for the removal of hydrogen sulfide and/or mercaptans from liquid streams are disclosed.Type: GrantFiled: August 24, 1990Date of Patent: September 22, 1992Assignee: The Texas A & M University SystemInventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
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Patent number: 5126491Abstract: Process for oxidating paraffinic compounds in order to yield the corresponding alcoholic and/or ketonic compounds, which process consists of reacting said paraffins with an aqueous solution of hydrogen peroxide, possibly dissolved in a solvent, by operating at a temperature comprised within the range of from 0.degree. C. to 100.degree. C., in the presence of a titanium-silicalite of formulapHMO.sub.2.qTiO.sub.2.SiO.sub.2whereinM is a metal selected from among aluminum, gallium and iron,p is comprised within the range of from 0 to 0.05 andq is comprised within the range of from 0.0001 to 0.04, and the H.sup.+ of HMO.sub.2 can be least partially replaceable or replaced by cations.Type: GrantFiled: August 3, 1990Date of Patent: June 30, 1992Assignee: Eniricerche S.p.A.Inventors: Mario G. Clerici, Bartolomeo Anfossi, Giuseppe Bellussi
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Patent number: 5021607Abstract: Saturated hydrocarbon chains are oxidized using a titanium containing silicalite catalyst having an infra red absorption band around 950 cm.sup.-1 preferably in solutions, the chains may be alkanes or alkyl groups of alkyl cyclic compounds.Type: GrantFiled: September 10, 1990Date of Patent: June 4, 1991Assignee: Exxon Chemical Patents Inc.Inventor: Diana R. Huybrechts
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Patent number: 5017729Abstract: Phenol is produced in a recycle manner by (a) reacting benzene with propylene to synthesize cumene, (b) oxidizing the cumene of step (a) into cumene hydroperoxide, (c) acid cleaving cumene hydroperoxide into phenol and acetone, (d) hydrogenating the acetone of step (c) into isopropanol, (e) dehydrating the isopropanol of step (d) into propylene, and (f) recycling the propylene of step (e) to step (a). It is also possible to take propylene from step (e). The acetone by-product produced upon preparation of phenol is converted into propylene which is useful by itself for any other uses or recycled to the phenol producing process.Type: GrantFiled: September 5, 1989Date of Patent: May 21, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hiroshi Fukuhara, Fujihisa Matsunaga
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Patent number: 5015786Abstract: In a first form, a process is provided for preparing phenol by converting acetone by-produced by the cumene process into isopropanol, and alkylating benzene with the isopropanol and optional propylene, thereby forming phenol without acetone by-product. And cumene is prepared by alkylating benzene in the presence of a zeolite catalyst using isopropanol or a mixture of isopropanol and propylene as an alkylating agent. Further provided is the continuous alkylation of benzene with isopropanol wherein a reaction mixture is divided into first and second portions, with the first portion being recycled to the reactor and the second portion being taken out as a reaction product.Type: GrantFiled: November 27, 1989Date of Patent: May 14, 1991Assignee: Mitsui Petrochemical Industries Inc.Inventors: Shintaro Araki, Fujihisa Matsunaga, Hiroshi Fukuhara
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Patent number: 5003109Abstract: The acetone peroxides contained in oxidate reaction mixtures thereof, e.g., those resulting from phenol syntheses, are hazardous and explosive compounds when present in the solid state, and are consumed by (a) adjusting the pH of such reaction mixture to a value ranging from 4 to 8; (b) adding a copper compound to such reaction mixture; and (c) maintaining such reaction mixture at a temperature ranging from 50.degree. C. to 150.degree. C.Type: GrantFiled: October 16, 1989Date of Patent: March 26, 1991Assignee: Rhone-Poulenc ChimieInventor: Michel Costantini
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Patent number: 4980514Abstract: Diketones useful as intermediates for reaction with carboxylic acids to provide surfactants and for reaction with amine adducts to provide fuel additives are prepared from polyoxyalkylene glycols having a molecular weight of about 200 to about 2,000 and having the formula: ##STR1## wherein R is hydrogen or methyl and wherein n is a positive number having a value of 1 to about 50,The polyoxyalkylene polyol is oxidized in the presence of a halogenated alkane solvent and a ruthenium catalyst with an alkali metal or alkaline earth metal hypochlorite at a temperature of about 10.degree. to about 50.degree. C. and a pressure of about 0 to 1,000 psig. over a period of about 10 to about 20 hours to provide the corresponding diketone having the formula: ##STR2## wherein R and n have the meaning given above.Type: GrantFiled: December 1, 1989Date of Patent: December 25, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4978799Abstract: A process for the production of detergent range alcohols and ketones by reacting an alkane with a hydroperoxide in the presence of a transition metal porphyrin catalyst is described. Preferred hydroperoxides include cumene hydroperoxide and tertiary butyl hydroperoxide. The transition metal porphyrin catalyst may be transition metal phthalocyanines, transition metalloporphines and the like. The transition metal itself may be iron, manganese, cobalt and mixtures thereof. Suitable ligands include, but are not limited to imidazoles and lithium borate. Other useful additives include alkali metal perchlorates, such as sodium perchlorate, iodosylbenzene and alkali metal superoxides, such as potassium superoxide, and phase transfer catalysts such as tetrabutyl ammonium bromide.Type: GrantFiled: October 30, 1989Date of Patent: December 18, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis, Howard F. Payton
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Patent number: 4978800Abstract: A process for the production of detergent range alcohols and ketones by reacting an alkane with a hydroperoxide in the presence of a transition metal acetylacetonate catalyst is described. Preferred hydroperoxides include cumene hydroperoxide and tertiary butyl hydroperoxide. The transition metal itself may be iron, ruthenium, chromium and mixtures thereof. If iron acetylacetonate is used as a catalyst, copper (II) acetate may be usefully employed as a co-catalyst.Type: GrantFiled: October 30, 1989Date of Patent: December 18, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis, John F. Knifton
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Patent number: 4970346Abstract: A process for the production of detergent range alcohols and ketones by reacting an alkane with a hydroperoxide in the presence of dicyano bis-(1,10-phenanthrolene)iron(II) is described. Preferred hydroperoxides include cumene hydroperoxide and tertiary butyl hydroperoxide.Type: GrantFiled: October 30, 1989Date of Patent: November 13, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4918238Abstract: Mixtures of alcohols and ketones are selectively and actively produced by catalytically oxidizing at least one alkane with an organic hydroperoxide, in the presence of a catalytically effective amount of osmium or an osmium compound, notably osmium tetroxide.Type: GrantFiled: March 3, 1989Date of Patent: April 17, 1990Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Jean-Pierre Lecomte
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Patent number: 4898987Abstract: A method is disclosed for the synthesis of phenol and acetone by acid-catalyzed decomposition over a catalyst comprising an acidic montmorillonite silica alumina clay, modified with a compound from the group consisting of a heteropoly acid, or the inorganic salt of zirconium, titanium and aluminum. The method allows for a 6-fold improvement in rate using heteropoly acid modified montmorillonite clays and a six to 10-food improvement is observed using zirconium or titanium, respectively.Type: GrantFiled: March 17, 1989Date of Patent: February 6, 1990Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 4868337Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.Type: GrantFiled: December 17, 1987Date of Patent: September 19, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4859799Abstract: Process for the production of aldehydes or ketones by oxidative cleavage of olefinic double bonds by means of a coordination complex of a ligand and a peroxo derivative of a metal of group 6b.Aldehydes and ketones obtained by said process are used among others as intermediates in the synthesis of organic products.Type: GrantFiled: May 20, 1988Date of Patent: August 22, 1989Assignee: Interox (Societe Anonyme)Inventors: Sandro Campestrini, Fulvio Di Furia, Giorgio Modena, Lucia Pasquato
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Patent number: 4849387Abstract: The present invention relates to a catalyst for the selective decomposition of cumene hydroperoxide, composed of zeolite crystals wherein a portion of the silicon atoms in the crystal lattice of silica is replaced by Al and B. The zeolite crystals are bonded to each other by a siliceous bonding agent which allows the catalyst to assume the shape of mechanically stable microspheres.The invention relates also to a process in which the catalyst is used, and to the related operating conditions.Type: GrantFiled: October 26, 1987Date of Patent: July 18, 1989Assignee: Enichem Sintesi S.p.A.Inventors: Ugo Romano, Mario G. Clerici, Giuseppe Bellussi, Franco Buonomo