Of Aldehyde Or Ketone Patents (Class 562/518)
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Patent number: 11053186Abstract: A process for the production of glycolic acid or a derivative thereof comprises: reacting formaldehyde with carbon monoxide and water in a carbonylation reactor in the presence of a sulfur catalyst, said reactor operating under suitable conditions, such that glycolic acid is formed; recovering a first product stream comprising glycolic acid, impurities and a sulfur species in the carbonylation reactor; passing the first product stream to an esterification reactor where it is subjected to esterification to form an alkylglycolate and wherein the esterification is catalysed by the sulfur species recovered in the first product stream; recovering a second product stream comprising the alkylglycolate, sulfur species and impurities from the esterification reactor; separating the sulfur species from the second product stream and recycling it to the carbonylation reactor in step (a) to form a sulphur depleted second product stream; separating the alkylglycolate from the sulphur depleted second product stream in a distType: GrantFiled: April 3, 2020Date of Patent: July 6, 2021Assignee: Johnson Matthey Davy Technologies LimitedInventors: Dena Roberts, David John Watson, John Swinney
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Patent number: 10335774Abstract: A catalyst system for a liquid phase carbonylation reaction comprising a homogeneous acid catalyst component and a porous solid component, in particular for use in the formation of glycolic acid by carbonylation of formaldehyde. The homogeneous acid catalyst component is, for instance, sulphuric acid while the solid component can be unfunctionalized silica. A process for the carbonylation of an aldehyde to form a carboxylic? acid or derivative thereof is also described. The process comprises the steps of contacting the catalyst with carbon monoxide, water and the aldehyde.Type: GrantFiled: March 24, 2016Date of Patent: July 2, 2019Assignee: Johnson Matthey Davy Technologies LimitedInventors: Simon Wayne Jackson, Adam Armour Snaith, Michael William Marshall Tuck, David John Watson
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Patent number: 9040748Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of aqueous formaldehyde. The water in the hydrocarboxylation zone is reduced via reaction with the ester bonds in a recycle stream comprising glycolic acid oligomers and/or methyl glycolate oligomers.Type: GrantFiled: June 8, 2012Date of Patent: May 26, 2015Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Scott Donald Barnicki, Robert Thomas Hembre, Kelley Margaret Moran, Stephen Neal Falling
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Patent number: 8927766Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of methylene dipropionate in the presence of a homogeneous acid catalyst and propionic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations. The homogeneous acid catalyst is readily separated from the hydrocarboxylation reaction effluent and recycled and the propionic acid is readily removed from the glycolic acid and the propionic acid is recycled.Type: GrantFiled: March 27, 2012Date of Patent: January 6, 2015Assignee: Eastman Chemical CompanyInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling
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Publication number: 20140343305Abstract: A process is provided for carrying out an oxidation on a feed including levulinic acid and/or a levulinic acid oxidation precursor to succinic acid, one or more furanic oxidation precursors of 2,5-furandicarboxylic acid and a catalytically effective combination of cobalt, manganese, and bromide components for catalyzing the oxidation of the levulinic acid component and of the one or more furanic oxidation precursors to produce both succinic acid and 2,5-furandicarboxylic acid products, which process comprises supplying the feed to a reactor vessel, supplying an oxidant, reacting the levulinic acid component and the one or more furanic oxidation precursors with the oxidant to produce both succinic acid and 2,5-furandicarboxylic acid (FDCA) and then recovering the succinic acid and FDCA products. A crude dehydration product from the dehydration of fructose, glucose or both, including 5-hydroxymethylfurfural, can be directly oxidized by the process to produce 2,5-furandicarboxylic acid and succinic acid.Type: ApplicationFiled: August 28, 2012Publication date: November 20, 2014Applicant: The University of KansasInventors: Bala Subramaniam, Xiaobin Zuo, Daryle H. Busch, Padmesh Venkitasubramaniam
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Publication number: 20140309399Abstract: The methods of the present invention comprise the steps of: providing a feedstock stream comprising an epoxide and carbon monoxide; contacting the feedstock stream with a metal carbonyl in a first reaction zone to effect conversion of at least a portion of the provided epoxide to a beta lactone; directing the effluent from the first reaction zone to a second reaction zone where the beta lactone is subjected to conditions that convert it to a compound selected from the group consisting of: an alpha beta unsaturated acid, an alpha beta unsaturated ester, an alpha beta unsaturated amide, and an optionally substituted polypropiolactone polymer; and isolating a final product comprising the alpha-beta unsaturated carboxylic acid, the alpha-beta unsaturated ester, the alpha-beta unsaturated amide or the polypropiolactone.Type: ApplicationFiled: October 25, 2012Publication date: October 16, 2014Applicant: Novomer, Inc.Inventors: Richard V. Porcelli, Jay J. Farmer, Robert E. Lapointe
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Patent number: 8765999Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of formaldehyde in the presence of a homogeneous acid catalyst and a carboxylic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations. The homogeneous acid catalyst is readily separated from the hydrocarboxylation reaction effluent and recycled and the carboxylic acid is readily removed from the glycolic acid and the carboxylic acid is recycled.Type: GrantFiled: March 27, 2012Date of Patent: July 1, 2014Assignee: Eastman Chemical CompanyInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Andrew James Vetter
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Removal of amine compounds from carbonylation process stream containing corrosion metal contaminants
Patent number: 8697908Abstract: A process for removing amine compounds from a process stream derived from a carbonylation process. The amine compounds may be present as iodide salts. The process stream also contains corrosion metal contaminants. The amine compounds are removed by mixing a portion of the process stream a slipstream to form an aqueous stream having a water concentration of greater than 50 wt. %. The aqueous stream is contacted with an exchange resin to remove amine compounds, as well as corrosion metal contaminants.Type: GrantFiled: May 5, 2011Date of Patent: April 15, 2014Assignee: Celanese International CorporationInventors: G. Paull Torrence, Brian Hokkanen, Yaw-Hwa Liu -
Publication number: 20130261333Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of formaldehyde in the presence of a solid acid catalyst and a carboxylic acid. This invention discloses hydrocarboxylations and corresponding glycolic acid separations wherein the glycolic acid stream is readily removed from the carboxylic acid and the carboxylic acid is recycled.Type: ApplicationFiled: March 27, 2012Publication date: October 3, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Mesfin Ejerssa Janka, Kelley Margaret Moran
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Publication number: 20130261328Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of formaldehyde in the presence of a homogeneous acid catalyst and a carboxylic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations. The homogeneous acid catalyst is readily separated from the hydrocarboxylation reaction effluent and recycled and the carboxylic acid is readily removed from the glycolic acid and the carboxylic acid is recycled.Type: ApplicationFiled: March 27, 2012Publication date: October 3, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Andrew James Vetter
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Patent number: 8501987Abstract: Process for producing glycolic acid by contacting carbon monoxide and formaldehyde, optionally in the presence of a solvent, with a catalyst including a solid acid. The solid acid is an acidic polyoxometalate compound insoluble in formaldehyde, glycolic acid and the optional solvent, and has a concentration of acid sites of greater than 60 ?mol g?1 on the external surface and/or a Hammett Acidity value of less than ?12.8.Type: GrantFiled: March 16, 2009Date of Patent: August 6, 2013Assignees: Dalian Institute of Chemical Physics, Chinese Academy of Sciences BP P.L.C.Inventors: Ying Sun, Hua Wang, Zhongmin Liu, Martin Philip Atkins
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Publication number: 20130116469Abstract: An object of the present invention is to provide a process for producing an N-acyl amino acid (1) in a good yield. The present invention provides a process for producing an N-acyl amino acid (1) by reacting an aldehyde compound (2), an amide compound (3), and carbon monoxide in the solvent in a reactor in the presence of a cobalt compound and hydrogen, characterized in the aldehyde compound (2), the amide compound (3) and the solvent are supplied to the reactor in which the solvent, the cobalt compound, hydrogen and carbon monoxide have been placed in advance.Type: ApplicationFiled: November 2, 2012Publication date: May 9, 2013Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Sumitomo Chemical Company, Limited
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Patent number: 8299297Abstract: Process for the production of glycolic acid by contacting carbon monoxide and formaldehyde with a catalyst containing an acidic polyoxometalate compound encapsulated within the pores of a zeolite. The zeolite has cages larger than the acidic polyoxometalate compound, and has pores with a diameter smaller than the diameter of the acidic polyoxometalate compound.Type: GrantFiled: May 20, 2008Date of Patent: October 30, 2012Assignees: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, BP P.L.C.Inventors: Ying Sun, Hua Wang, Zhongmin Liu
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Publication number: 20120245381Abstract: There is provided a method for producing N-acylamino acid of formula (I): wherein R1, R2 and R3 are the same or different and each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted heterocyclic group, which comprises supplying an aldehyde compound of formula (II): wherein R1 is as defined above, an amide compound of formula (III): wherein R2 and R3 are as defined above, and a solvent to a reactor in which a solvent, a palladium compound, a halide compound, and carbon monoxide had been charged.Type: ApplicationFiled: March 20, 2012Publication date: September 27, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Toshiaki SUZUKI
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Publication number: 20120215027Abstract: Disclosed is a process for the extractive recovery of an acid catalyst from an aqueous mixture of glycolic acid with an extraction solvent comprising a tertiary amine or an onium carboxylate compound, a modifier, and a diluent. The acid catalyst, which can comprise strong acids such as sulfuric acid, alkyl sulfonic acids, and fluoroalkyl sulfonic acids, can be recovered by back extraction with aqueous formaldehyde and recycled to a process for the preparation of glycolic acid by the acid-catalyzed carbonylation of formaldehyde. Also disclosed is a process for the preparation of glycolic acid by the acid-catalyzed hydrocarboxylation of formaldehyde.Type: ApplicationFiled: March 27, 2012Publication date: August 23, 2012Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Stephen Neal Falling, Jeffrey Scott Kanel, Robert Sterling Kline, Peter Borden Mackenzie, Andrew James Vetter
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Publication number: 20120078011Abstract: The present invention relates to improved processes for the manufacture of acetic acid. A pump around reactor is used to produce additional heat for the production of steam. The pump around reactor receives a portion of the reaction solution produced by the carbonylation reactor and further reacts that portion with additional carbon monoxide and/or reactants.Type: ApplicationFiled: September 24, 2010Publication date: March 29, 2012Applicant: CELANESE INTERNATIONAL CORPORATIONInventor: Raymond J. Zinobile
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Publication number: 20120078010Abstract: Disclosed is a process for the extractive recovery of an acid catalyst from an aqueous mixture of glycolic acid with an extraction solvent comprising a tertiary amine or an onium carboxylate compound, a modifier, and a diluent. The acid catalyst, which can comprise strong acids such as sulfuric acid, alkyl sulfonic acids, and fluoroalkyl sulfonic acids, can be recovered by back extraction with aqueous formaldehyde and recycled to a process for the preparation of glycolic acid by the acid-catalyzed carbonylation of formaldehyde.Type: ApplicationFiled: September 23, 2010Publication date: March 29, 2012Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Stephen Neal Falling, Jeffrey Scott Kanel, Robert Sterling Kline, Peter Borden Mackenzie
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Patent number: 8076506Abstract: A process for reducing the aldehyde concentration in a target stream of a carbonylation process is disclosed. More specifically, a process for reducing the aldehyde concentration in an internal process stream or feed stream of a carbonylation process is disclosed. In particular, a process in which a target stream comprising a carbonylatable reactant and a first aldehyde concentration is subjected to a reaction comprising a supported catalyst that comprises at least one Group 8 to Group 11 metal at conditions sufficient to reduce the first aldehyde concentration to a second aldehyde concentration is disclosed.Type: GrantFiled: April 3, 2007Date of Patent: December 13, 2011Assignee: Celanese International CorporationInventors: Barbara F. M. Kimmich, Jeremy J. Patt, Mark O. Scates, Ronald D. Shaver, James H. Zink
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Publication number: 20110166383Abstract: A process for producing glycolic acid from carbon monoxide and formaldehyde using a catalyst comprising an acidic polyoxometalate compound encapsulated within the pores of a zeolite, wherein the zeolite has cages larger than the acidic polyoxometalate compound, the zeolite also having pores with a diameter smaller than that of the acidic polyoxometalate compound.Type: ApplicationFiled: May 20, 2008Publication date: July 7, 2011Inventors: Ying Sun, Hua Wang, Zhongmin Liu
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Publication number: 20100087679Abstract: The invention relates to a method for the production of a-keto acids and esters thereof, in particular to a method of producing 13C1-?-keto acids and esters thereof i.e. ?-keto acids and esters thereof which are 13C-enriched at the C1-atom (carboxyl atom). More particularly, the invention relates to a method of producing pyruvic acid and esters thereof, in particular 13 C1-pyruvic acid and esters thereof.Type: ApplicationFiled: October 16, 2007Publication date: April 8, 2010Inventors: Torgrim Engell, Christian Glogard
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Patent number: 7304187Abstract: There is provided a process for reducing formaldehyde content of a gas comprising the step of contacting the gas with an aqueous oxidizing solution comprising at least one cation, a base, and H2O2 so as to oxidize at least a part of the formaldehyde contained in the gas into formic acid. Thus, a gas having a reduced content in formaldehyde as compared to the gas before the process and a solution comprising formic acid, are so-obtained. Such a process can be particularly useful for treating various types of gases containing formaldehyde.Type: GrantFiled: October 7, 2005Date of Patent: December 4, 2007Assignee: Groupe Conseil ProCD Inc.Inventors: Stéphane Chabot, Martin Beaulieu, Yves Charest, Dominique Le Bel
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Patent number: 7161044Abstract: An object of the present invention is to provide a catalytic gas phase oxidation reaction in which: even under reaction conditions of a higher gas pressure, a higher concentration of the raw material gas and a larger space velocity of a reaction gas, the thermal accumulation at the hot spot portion can be sufficiently suppressed with ease and at low costs, so that the reaction can be continued for a long time while a high yield is maintained.Type: GrantFiled: October 4, 2004Date of Patent: January 9, 2007Assignee: Nippon Shokubai Co., Ltd.Inventors: Daisuke Nakamura, Michio Tanimoto
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Patent number: 7002010Abstract: The instant invention discloses a process for the preparation of compounds of the formula I: wherein the general symbols are as defined in claim 1, which process comprises reacting a compound of formula II: wherein the general symbols are as defined in claim 1, with a compound of the formula III: wherein R5 is as defined in claim 1. The compounds of the formula II are new and useful as stabilizers for protecting organic materials, in particular synthetic polymers, reprographic materials or coating materials against oxidative, thermal or light-induced degradation.Type: GrantFiled: December 4, 2001Date of Patent: February 21, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Dario Lazzari, Mirko Rossi, Giuseppe Veronesi, Nazzareno Ruggeri, Katharina Fritzsche, Adalbert Braig
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Publication number: 20040249196Abstract: In a process for heterogeneously catalyzed partial gas phase oxidation of acrolein to acrylic acid, the starting reaction gas mixture is oxidized over a fixed catalyst bed 1 which consists of at least two fixed catalyst bed zones and is accommodated in two successive temperature zones A, B, and the transition from temperature zone A to temperature zone B does not coincide with a transition from one fixed catalyst bed zone to another fixed catalyst bed zone.Type: ApplicationFiled: March 19, 2004Publication date: December 9, 2004Applicant: BASF AktiengesellschaftInventors: Martin Dieterle, Jochen Petzoldt, Heiko Arnold, Wilhelm Ruppel, Klaus Joachim Muller-Engel
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Patent number: 6812366Abstract: A catalyst useful for oxidation reactions is disclosed. The catalyst is useful for the gas phase oxidation of alkanes, propylene, acrolein, or isopropanol to unsaturated aldehydes or carboxylic acids.Type: GrantFiled: September 2, 2003Date of Patent: November 2, 2004Assignee: Rohm and Haas CompanyInventor: Manhua Lin
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Patent number: 6664416Abstract: The present invention produces (meth)acrylic acid in a high yield in a process for producing (meth)acrylic acid by subjecting at least one member selected from the group consisting of (meth)acrolein, propane, and isobutane to catalytic gas phase oxidation with molecular oxygen or a molecular-oxygen-containing gas. In addition, the present invention makes it possible to produce (meth)acrylic acid in a high yield and stably for a long time. The present invention provides a process for producing (meth)acrylic acid by catalytic gas phase oxidation reaction, which is characterized by allowing a reaction gas to contain a reducible compound.Type: GrantFiled: April 6, 2002Date of Patent: December 16, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Michio Tanimoto, Hiroto Kasuga
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Publication number: 20030212295Abstract: Disclosed is a continuous process wherein carbon monoxide, a carbonylatable reactant, and a halide in the gas phase are contacted with a non-volatile catalyst solution comprising an ionic liquid and a Group VIII metal to produce a carbonylation product in the gas phase. The process is useful for the continuous preparation of acetic acid by the carbonylation of methanol.Type: ApplicationFiled: May 9, 2003Publication date: November 13, 2003Inventors: Gerald Charles, Regina Michelle
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Patent number: 6623665Abstract: The present invention relates to nonlinear optical (NLO) materials, compositions thereof and NLO devices using polymeric matrices supporting a second order NLO material defined by the formula ED—B—EW (I) where ED is an electron donating moiety, B is a bridging moiety, and EW is the electron withdrawing moiety (terminal acceptor group) defined by formula II, where C1 is a carbon atom linked through a double bond to a cyclic or an acylic carbon atom in the bridging moiety, and A1, A2, A3 or A4are the same or different from one another, each of which is an electron withdrawing group such as CN, COR, COOR, COOH or CH═C(R)2 where R is a C1-6 alkyl.Type: GrantFiled: February 22, 2000Date of Patent: September 23, 2003Assignee: Lockheed Martin CorporationInventor: Susan P. Ermer
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Patent number: 6583312Abstract: The invention relates to a novel process for preparing optically active trimethyllactic acid and/or its esters by catalytic hydrogenation of trimethylpyruvic acid and/or its esters in the presence of noble metal complex catalysts containing phosphorus ligands.Type: GrantFiled: May 24, 2001Date of Patent: June 24, 2003Assignee: Bayer AktiengesellschaftInventors: Wolfram Sirges, Claus Dreisbach
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Patent number: 6566551Abstract: For use in a process for the production of (meth)acrylic acid comprising at least a step for the reaction of (meth)acrylic acid by catalytic gas phase oxidation and a step for the absorption thereof, a method for preventing an effluent gas pipe from blocking is disclosed, which method is characterized by causing part or the whole of the gas discharged from the step for absorption, while being circulated via the effluent gas pipe to the step for the reaction or being discarded, to be subjected to temperature elevation and application of pressure and/or mist separation. Particularly by setting the temperature of the waste gas from the absorption column at a level in the range of 30-70° C.Type: GrantFiled: November 29, 2000Date of Patent: May 20, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Takeshi Nishimura, Yukihiro Matsumoto, Sei Nakahara, Misao Inada, Harunori Hirao, Mamoru Takamura
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Patent number: 6525217Abstract: A process for the catalytic gas-phase oxidation of propene to acrylic acid, in which the reaction gas starting mixture is oxidized, with an increased propene loading, in a first reaction stage, over a first fixed-bed catalyst and then the acrolein-containing product gas mixture of the first reaction stage is oxidized, in a second reaction stage, with an increased acrolein loading, over a second fixed-bed catalyst, the catalyst moldings in both reaction stages having an annular geometry.Type: GrantFiled: August 30, 2001Date of Patent: February 25, 2003Assignee: BASF AktiengesellschaftInventors: Signe Unverricht, Heiko Arnold, Andreas Tenten, Ulrich Hammon, Hans-Peter Neumann, Klaus Harth
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Patent number: 6452043Abstract: A method for producing esters, carboxylic acids and mixtures thereof includes contacting, under carbonylation conditions, lower alkyl alcohols, ethers, lower alkyl alcohol derivatives and mixtures thereof and carbon monoxide with a catalyst having a catalytically effective amount a metal selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, tin and mixtures thereof associated with a carbonized polysulfonated divinylbenzene-styrene copolymer matrix. In a preferred aspect of the invention the method is called out under vapor-phase conditions.Type: GrantFiled: April 5, 2000Date of Patent: September 17, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6420304Abstract: The invention relates to a polymer-supported carbonylation catalyst and its use in a process for preparing organic carboxylic acid or anhydride having n+1 carbon atoms. The invention relates also to a process for preparing organic carboxylic acid or anhydride having n+1 carbon atoms by carbonylating with monoxide, in the presence of the above-mentioned carbonylation catalyst, on alcohols having n carbon atoms, ethers having 2n carbon atoms or esters formed from said alcohols and acids. In particular, the invention relates to a process for preparing acetic acid by carbonylating methanol with carbon monooxide in the presence of said carbonylation catalyst. By using said carbonylation catalyst, the temperature for carbonylation can be lowered to about 160° C. with a reaction rate better than that of a traditional process, while the tendency of catalyst precipitation in the course of carbonylation can be improved also.Type: GrantFiled: April 20, 2000Date of Patent: July 16, 2002Assignee: China Petrochemical Development CorporationInventors: Chia-Jung Tsai, Yao-Lung Liu, Hsi-Chin Tsai
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Patent number: 6403829Abstract: In a process for the catalytic gas-phase oxidation of acrolein to acrylic acid, the reaction gas starting mixture is passed, with an acrolein loading of ≧150 l (s.t.p.)/l.h, over a fixed-bed catalyst which is housed in two spatially successive reaction zones A, B, the reaction zone B being kept at a higher temperature than the reaction zone A.Type: GrantFiled: September 10, 2001Date of Patent: June 11, 2002Assignee: BASF AktiengesellschaftInventors: Signe Unverricht, Heiko Arnold, Andreas Tenten, Ulrich Hammon
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Patent number: 6395927Abstract: A method for preparing acetic acid and/or methyl acetate by simultaneous isomerization and carbonylation reactions. A reaction mixture is provided containing at least one reagent which provides formyl radicals and at least one further reagent which provides methyl radicals, together with water in an amount of at most 5% by weight, carbon monoxide at a partial pressure between 0.1·105 Pa and 25·105 Pa, a solvent and a catalytic system which contains at least one halogenated promoter and at least one iridium-based compound. In a typical reaction mixture, methyl formate is isomerized to form acetic acid according to the reaction: HCOOCH3CH3COOH while methanol undergoes carbonylation to form acetic acid according to the reaction: CH3OH+COCH3COOH The reagent which provides the formyl radicals is kept at or below 20% by weight of the reaction mixture, while the molar ratio of methyl radicals to formyl radicals in the mixture is greater than 1.Type: GrantFiled: September 23, 1998Date of Patent: May 28, 2002Assignee: Acetex ChimieInventors: Carl Patois, Robert Perron, Daniel Thiebaut
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Patent number: 6326455Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.Type: GrantFiled: April 5, 2001Date of Patent: December 4, 2001Assignee: RPC Inc.Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
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Publication number: 20010023285Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.Type: ApplicationFiled: April 5, 2001Publication date: September 20, 2001Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
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Publication number: 20010007911Abstract: The invention relates to a process for preparing N-acylglycine derivatives of the formula (III) 1Type: ApplicationFiled: July 7, 1999Publication date: July 12, 2001Inventors: HOLGER GEISSLER, SANDRA BOGDANOVIC, MATTHIAS BELLER, MARKUS ECKERT, FRANK VOLLMULLER
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Patent number: 6084124Abstract: The present invention is a method to produce an unsaturated carboxylic acid which includes the steps of: providing an epoxy compound; contacting the epoxy compound with carbon monoxide in the presence of a catalytically effective amount of a catalyst system comprising tin and cobalt under conditions effective for carbonylation of the epoxy; and recovering a .alpha.-.beta. unsaturated carboxylic acid product. The preferred epoxy is ethylene oxide which is reacted to acrylic acid by the method of the present invention.Type: GrantFiled: February 4, 1999Date of Patent: July 4, 2000Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Thomas Clayton Forschner
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Patent number: 5808143Abstract: Catalysts of the formula I?A.sub.a B.sub.b O.sub.x !.sub.p ?C.sub.c D.sub.d Fe.sub.e Co.sub.f E.sub.i F.sub.j O.sub.y !.sub.q I,whereA is bismuth, tellurium, antimony, tin and/or copper,B is molybdenum and/or tungsten,C is an alkali metal, thallium and/or samarium,D is an alkaline earth metal, nickel, copper, cobalt, manganese, zinc, tin, cerium, chromium, cadmium, molybdenum, bismuth and/or mercury,E is phosphorus, arsenic, boron and/or antimony,F is a rare-earth metal, vanadium and/or uranium,a is from 0.01 to 8,b is from 0.1 to 30,c is from 0 to 4,d is from 0 to 20,e is from 0 to 20,f is from 0 to 20,i is from 0 to 6,j is from 0 to 15,x and y are numbers determined by the valency and frequency of the elements other than oxygen in I, and p and q are numbers whose ratio p/q is in the range from 0.001 to 0.Type: GrantFiled: March 22, 1996Date of Patent: September 15, 1998Assignee: BASF AktiengesellschaftInventors: Lothar Karrer, Hans-Peter Neumann, Hans-Dieter Eichhorn, Robin Stuart Jarret
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Patent number: 5650537Abstract: A process for the preparation of N-acylglycine derivatives of the formula (I) ##STR1## which comprises reacting a carboxylic acid amide with an aldehyde in the presence of a solvent and an acid to give an acylaminomethylol and then carbonylating the acylaminomethylol in the presence of a cobalt carbonyl catalyst.Type: GrantFiled: May 2, 1995Date of Patent: July 22, 1997Assignee: Hoechst AGInventors: Matthias Beller, Hartmut Fischer, Thomas Gerdau, Peter Gross
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Patent number: 5312969Abstract: Difunctional butenes are linearly dicarbonylated into 3-hexene-1,6-dioic acid or alkyl diesters thereof, well suited for the ultimate production of, e.g., adipic acid, by reacting such difunctional butene with carbon monoxide and, if appropriate, an alcohol, at an elevated temperature under superatmospheric pressure, in the presence of at least one source of hydrogen chloride and a catalytically effective amount of palladium, at least a portion of which palladium being in the zero oxidation state, as well as a quaternary onium chloride of nitrogen or phosphorus, the nitrogen or phosphorus atom being tetracoordinated to carbon atoms, with the proviso that the nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: May 18, 1992Date of Patent: May 17, 1994Assignee: Rhone-Poulenc ChimieInventors: Marc Huser, Sylvain Mutez, Robert Perron
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Patent number: 5003104Abstract: This invention involves a process for the carbonylation of a carbonylatable reactant, e.g., an alkyl ester, a dialkyl ether or mixtures thereof by reacting the same with carbon monoxide. The process comprises effecting the carbonylation in the presence of a solution of a catalyst system containing a rhodium compound, an iodide and a lithium component at a temperature of from 50.degree. C. to 400.degree. C. at a carbon monoxide partial pressure of 1 psig to 15,000 psig. Hydrogen may also be present. The invention also concerns a carbonylation catalyst system effective for the addition of carbon monoxide to a carbonylatable reactant which comprises a solution containing as essential components a rhodium containing active component, an iodide and a lithium component.Type: GrantFiled: October 31, 1988Date of Patent: March 26, 1991Assignee: BP Chemicals LimitedInventors: Frank E. Paulik, Arnold Hershman, Walter R. Knox, Robert G. Schultz, James F. Roth
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Patent number: 4954466Abstract: A process is provided for recovering cobalt values from a cobalt-N-acetyliminodiacetic acid complex by dissolving the complex in an aqueous solution of a strong acidic solution, extracting the acid solution with a hydrocarbon solvent containing a trialkylamine to transfer the cobalt from the aqueous solution into the hydrocarbon solvent, stripping the cobalt from the hydrocarbon solvent with water, and precipitating the cobalt from the stripping water by using a strong alkali.Type: GrantFiled: November 30, 1989Date of Patent: September 4, 1990Assignee: Monsanto CompanyInventor: Robert B. Weisenfeld
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Patent number: 4918222Abstract: An N-acetylglycine is manufactured by reacting paraformaldehyde with an acetamide and carbon monoxide in the present of a cobalt-containing catalyst promoted by a sulfoxide or dinitride compounds. The presence of sulfoxide or dinitrile ligands are essential for the high yield synthesis of N-acetylglycine and good cobalt recovery.Type: GrantFiled: August 10, 1987Date of Patent: April 17, 1990Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton, Ernest L. Yeakey
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Patent number: 4892687Abstract: A process is disclosed for producing N-acetyl-aminoacid which comprises reacting a feedstock from the group consisting of simple olefins, acetamide and synthesis gas with a catalyst comprising a cobalt-containing compound promoted by a bidental-phosphine ligand in a solvent at a pressure of 500 psi or greater and a temperature of 50.degree. C. or greater. The presence of the ligand increases both reaction rate and cobalt catalyst stability.Type: GrantFiled: October 8, 1986Date of Patent: January 9, 1990Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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Patent number: 4824997Abstract: A method of carbonylation of formaldehyde is disclosed. In the method, an aqueous formaldehyde concentrate comprising between about 60% by weight and about 85% by weight formaldehyde, carbon monoxide and sulfuric acid are brought together in the absence of an effective amount of added Group IB cocatalyst in a reaction zone under a carbon monoxide partial pressure in the reaction zone of not greater than about 1.72.times.10.sup.7 N/M.sup.2. A carbonylation reaction is thereby effected in which a carbonylation product is produced comprising at least about 2% by weight sulfuric acid and a mixture of compounds of the formula:HO(CH.sub.2 COO).sub.n Hwherein n is a positive integer of at least 1. Also disclosed is a method for preparation of an alkyl glycolate by esterification of the carbonylation reaction mixture.Type: GrantFiled: January 25, 1988Date of Patent: April 25, 1989Assignee: Monsanto CompanyInventors: Alistair MacFarlane, David R. Dyroff, Robert V. Brill
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Patent number: 4705867Abstract: 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at a temperature between -60.degree. C. and -10.degree. C.Type: GrantFiled: April 4, 1986Date of Patent: November 10, 1987Assignee: Degussa AktiengesellschaftInventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
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Patent number: 4694108Abstract: A process of producing higher ketones comprises the step of contacting under suitable conditions a feed comprising (a) at least one C.sub.3 -C.sub.6 aliphatic ketone, (b) at least one C.sub.2 -C.sub.6 aliphatic aldehyde and, preferably, also (c) carbon monoxide with a catalyst composition comprising (i) copper or an oxide thereof and (ii) zinc oxide. Preferably, the feed ketone is methyl ethyl ketone, the feed aldehyde is propanal, and the product comprises at least one C.sub.7 ketone.Type: GrantFiled: August 1, 1986Date of Patent: September 15, 1987Assignee: Phillips Petroleum CompanyInventor: David J. Elliott
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Patent number: 4533500Abstract: N-acyliminodiacetic acids are manufactured by reacting formaldehyde or a formaldehyde generator compound with a N-unsubstituted amide or a generator thereof and with carbon monoxide in contact with a carbonylation catalyst, for example, a cobalt compound, the ratio of the aldehyde groups to the amide groups being at least 2:1. The formaldehyde generator can be a polymeric form of formaldehyde and the amide generator can be a carboxylic ester, acid or anhydride.Type: GrantFiled: March 17, 1983Date of Patent: August 6, 1985Assignees: Institut Francais du Petrole, Societe Nationale Elf-Aquitaine (Production)Inventors: Yves Chauvin, Dominique Commereuc, Andre Hirschauer, Dominique Reffet, Robert Stern