Of Aldehyde Or Ketone Patents (Class 562/518)
  • Patent number: 11053186
    Abstract: 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 dist
    Type: Grant
    Filed: April 3, 2020
    Date of Patent: July 6, 2021
    Assignee: Johnson Matthey Davy Technologies Limited
    Inventors: Dena Roberts, David John Watson, John Swinney
  • Patent number: 10335774
    Abstract: 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: Grant
    Filed: March 24, 2016
    Date of Patent: July 2, 2019
    Assignee: Johnson Matthey Davy Technologies Limited
    Inventors: Simon Wayne Jackson, Adam Armour Snaith, Michael William Marshall Tuck, David John Watson
  • Patent number: 9040748
    Abstract: 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: Grant
    Filed: June 8, 2012
    Date of Patent: May 26, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Scott Donald Barnicki, Robert Thomas Hembre, Kelley Margaret Moran, Stephen Neal Falling
  • Patent number: 8927766
    Abstract: 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: Grant
    Filed: March 27, 2012
    Date of Patent: January 6, 2015
    Assignee: Eastman Chemical Company
    Inventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling
  • Publication number: 20140343305
    Abstract: 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: Application
    Filed: August 28, 2012
    Publication date: November 20, 2014
    Applicant: The University of Kansas
    Inventors: Bala Subramaniam, Xiaobin Zuo, Daryle H. Busch, Padmesh Venkitasubramaniam
  • Publication number: 20140309399
    Abstract: 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: Application
    Filed: October 25, 2012
    Publication date: October 16, 2014
    Applicant: Novomer, Inc.
    Inventors: Richard V. Porcelli, Jay J. Farmer, Robert E. Lapointe
  • Patent number: 8765999
    Abstract: 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: Grant
    Filed: March 27, 2012
    Date of Patent: July 1, 2014
    Assignee: Eastman Chemical Company
    Inventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Andrew James Vetter
  • Patent number: 8697908
    Abstract: 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: Grant
    Filed: May 5, 2011
    Date of Patent: April 15, 2014
    Assignee: Celanese International Corporation
    Inventors: G. Paull Torrence, Brian Hokkanen, Yaw-Hwa Liu
  • Publication number: 20130261328
    Abstract: 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: Application
    Filed: March 27, 2012
    Publication date: October 3, 2013
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Andrew James Vetter
  • Publication number: 20130261333
    Abstract: 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: Application
    Filed: March 27, 2012
    Publication date: October 3, 2013
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Mesfin Ejerssa Janka, Kelley Margaret Moran
  • Patent number: 8501987
    Abstract: 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: Grant
    Filed: March 16, 2009
    Date of Patent: August 6, 2013
    Assignees: Dalian Institute of Chemical Physics, Chinese Academy of Sciences BP P.L.C.
    Inventors: Ying Sun, Hua Wang, Zhongmin Liu, Martin Philip Atkins
  • Publication number: 20130116469
    Abstract: 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: Application
    Filed: November 2, 2012
    Publication date: May 9, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Sumitomo Chemical Company, Limited
  • Patent number: 8299297
    Abstract: 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: Grant
    Filed: May 20, 2008
    Date of Patent: October 30, 2012
    Assignees: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, BP P.L.C.
    Inventors: Ying Sun, Hua Wang, Zhongmin Liu
  • Publication number: 20120245381
    Abstract: 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: Application
    Filed: March 20, 2012
    Publication date: September 27, 2012
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Toshiaki SUZUKI
  • Publication number: 20120215027
    Abstract: 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: Application
    Filed: March 27, 2012
    Publication date: August 23, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Scott Donald Barnicki, Stephen Neal Falling, Jeffrey Scott Kanel, Robert Sterling Kline, Peter Borden Mackenzie, Andrew James Vetter
  • Publication number: 20120078010
    Abstract: 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: Application
    Filed: September 23, 2010
    Publication date: March 29, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Scott Donald Barnicki, Stephen Neal Falling, Jeffrey Scott Kanel, Robert Sterling Kline, Peter Borden Mackenzie
  • Publication number: 20120078011
    Abstract: 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: Application
    Filed: September 24, 2010
    Publication date: March 29, 2012
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventor: Raymond J. Zinobile
  • Patent number: 8076506
    Abstract: 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: Grant
    Filed: April 3, 2007
    Date of Patent: December 13, 2011
    Assignee: Celanese International Corporation
    Inventors: Barbara F. M. Kimmich, Jeremy J. Patt, Mark O. Scates, Ronald D. Shaver, James H. Zink
  • Publication number: 20110166383
    Abstract: 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: Application
    Filed: May 20, 2008
    Publication date: July 7, 2011
    Inventors: Ying Sun, Hua Wang, Zhongmin Liu
  • Publication number: 20100087679
    Abstract: 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: Application
    Filed: October 16, 2007
    Publication date: April 8, 2010
    Inventors: Torgrim Engell, Christian Glogard
  • Patent number: 7304187
    Abstract: 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: Grant
    Filed: October 7, 2005
    Date of Patent: December 4, 2007
    Assignee: Groupe Conseil ProCD Inc.
    Inventors: Stéphane Chabot, Martin Beaulieu, Yves Charest, Dominique Le Bel
  • Patent number: 7161044
    Abstract: 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: Grant
    Filed: October 4, 2004
    Date of Patent: January 9, 2007
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Daisuke Nakamura, Michio Tanimoto
  • Patent number: 7002010
    Abstract: 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: Grant
    Filed: December 4, 2001
    Date of Patent: February 21, 2006
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Dario Lazzari, Mirko Rossi, Giuseppe Veronesi, Nazzareno Ruggeri, Katharina Fritzsche, Adalbert Braig
  • Publication number: 20040249196
    Abstract: 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: Application
    Filed: March 19, 2004
    Publication date: December 9, 2004
    Applicant: BASF Aktiengesellschaft
    Inventors: Martin Dieterle, Jochen Petzoldt, Heiko Arnold, Wilhelm Ruppel, Klaus Joachim Muller-Engel
  • Patent number: 6812366
    Abstract: 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: Grant
    Filed: September 2, 2003
    Date of Patent: November 2, 2004
    Assignee: Rohm and Haas Company
    Inventor: Manhua Lin
  • Patent number: 6664416
    Abstract: 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: Grant
    Filed: April 6, 2002
    Date of Patent: December 16, 2003
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Michio Tanimoto, Hiroto Kasuga
  • Publication number: 20030212295
    Abstract: 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: Application
    Filed: May 9, 2003
    Publication date: November 13, 2003
    Inventors: Gerald Charles, Regina Michelle
  • Patent number: 6623665
    Abstract: 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: Grant
    Filed: February 22, 2000
    Date of Patent: September 23, 2003
    Assignee: Lockheed Martin Corporation
    Inventor: Susan P. Ermer
  • Patent number: 6583312
    Abstract: 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: Grant
    Filed: May 24, 2001
    Date of Patent: June 24, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Sirges, Claus Dreisbach
  • Patent number: 6566551
    Abstract: 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: Grant
    Filed: November 29, 2000
    Date of Patent: May 20, 2003
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Takeshi Nishimura, Yukihiro Matsumoto, Sei Nakahara, Misao Inada, Harunori Hirao, Mamoru Takamura
  • Patent number: 6525217
    Abstract: 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: Grant
    Filed: August 30, 2001
    Date of Patent: February 25, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Signe Unverricht, Heiko Arnold, Andreas Tenten, Ulrich Hammon, Hans-Peter Neumann, Klaus Harth
  • Patent number: 6452043
    Abstract: 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: Grant
    Filed: April 5, 2000
    Date of Patent: September 17, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6420304
    Abstract: 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: Grant
    Filed: April 20, 2000
    Date of Patent: July 16, 2002
    Assignee: China Petrochemical Development Corporation
    Inventors: Chia-Jung Tsai, Yao-Lung Liu, Hsi-Chin Tsai
  • Patent number: 6403829
    Abstract: 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: Grant
    Filed: September 10, 2001
    Date of Patent: June 11, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Signe Unverricht, Heiko Arnold, Andreas Tenten, Ulrich Hammon
  • Patent number: 6395927
    Abstract: 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: Grant
    Filed: September 23, 1998
    Date of Patent: May 28, 2002
    Assignee: Acetex Chimie
    Inventors: Carl Patois, Robert Perron, Daniel Thiebaut
  • Patent number: 6326455
    Abstract: 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: Grant
    Filed: April 5, 2001
    Date of Patent: December 4, 2001
    Assignee: RPC Inc.
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Publication number: 20010023285
    Abstract: 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: Application
    Filed: April 5, 2001
    Publication date: September 20, 2001
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Publication number: 20010007911
    Abstract: The invention relates to a process for preparing N-acylglycine derivatives of the formula (III) 1
    Type: Application
    Filed: July 7, 1999
    Publication date: July 12, 2001
    Inventors: HOLGER GEISSLER, SANDRA BOGDANOVIC, MATTHIAS BELLER, MARKUS ECKERT, FRANK VOLLMULLER
  • Patent number: 6084124
    Abstract: 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: Grant
    Filed: February 4, 1999
    Date of Patent: July 4, 2000
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Thomas Clayton Forschner
  • Patent number: 5808143
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Karrer, Hans-Peter Neumann, Hans-Dieter Eichhorn, Robin Stuart Jarret
  • Patent number: 5650537
    Abstract: 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: Grant
    Filed: May 2, 1995
    Date of Patent: July 22, 1997
    Assignee: Hoechst AG
    Inventors: Matthias Beller, Hartmut Fischer, Thomas Gerdau, Peter Gross
  • Patent number: 5312969
    Abstract: 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: Grant
    Filed: May 18, 1992
    Date of Patent: May 17, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Huser, Sylvain Mutez, Robert Perron
  • Patent number: 5003104
    Abstract: 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: Grant
    Filed: October 31, 1988
    Date of Patent: March 26, 1991
    Assignee: BP Chemicals Limited
    Inventors: Frank E. Paulik, Arnold Hershman, Walter R. Knox, Robert G. Schultz, James F. Roth
  • Patent number: 4954466
    Abstract: 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: Grant
    Filed: November 30, 1989
    Date of Patent: September 4, 1990
    Assignee: Monsanto Company
    Inventor: Robert B. Weisenfeld
  • Patent number: 4918222
    Abstract: 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: Grant
    Filed: August 10, 1987
    Date of Patent: April 17, 1990
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton, Ernest L. Yeakey
  • Patent number: 4892687
    Abstract: 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: Grant
    Filed: October 8, 1986
    Date of Patent: January 9, 1990
    Assignee: Texaco Inc.
    Inventor: Jiang-Jen Lin
  • Patent number: 4824997
    Abstract: 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: Grant
    Filed: January 25, 1988
    Date of Patent: April 25, 1989
    Assignee: Monsanto Company
    Inventors: Alistair MacFarlane, David R. Dyroff, Robert V. Brill
  • Patent number: 4705867
    Abstract: 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: Grant
    Filed: April 4, 1986
    Date of Patent: November 10, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
  • Patent number: 4694108
    Abstract: 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: Grant
    Filed: August 1, 1986
    Date of Patent: September 15, 1987
    Assignee: Phillips Petroleum Company
    Inventor: David J. Elliott
  • Patent number: 4533500
    Abstract: 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: Grant
    Filed: March 17, 1983
    Date of Patent: August 6, 1985
    Assignees: Institut Francais du Petrole, Societe Nationale Elf-Aquitaine (Production)
    Inventors: Yves Chauvin, Dominique Commereuc, Andre Hirschauer, Dominique Reffet, Robert Stern