Preparing Esters By Carbonylation Patents (Class 560/175)
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Patent number: 11773048Abstract: A process is provided for the preparation of value added chemicals such as ethyl levulinate from a glucose or other sugars, catalyzed by a mixture of a Lewis acid catalyst and a Bronsted acid catalyst.Type: GrantFiled: January 15, 2020Date of Patent: October 3, 2023Assignee: Council of Scientific & Industrial ResearchInventors: Vijay Bokade, Prashant Niphadkar
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Patent number: 10315979Abstract: Preparation of 2,5,6-trihydroxy-3-hexenoic acid and 2,5-dihydroxy-3-pentenoic acid and esters thereof from C6 and C5 sugars in the presence of a Lewis Acid material, wherein the yield of the 2,5,6-trihydroxy-3-hexenoic acid or 2,5-dihydroxy-3-pentenoic acid or esters thereof exceeds 15%.Type: GrantFiled: June 20, 2016Date of Patent: June 11, 2019Assignee: HALDOR TOPSØE A/SInventors: Esben Taarning, Irantzu Sadaba Zubiri, Sebastian Meier
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Patent number: 9073966Abstract: The present invention relates to a method for screening compounds having the ability to prevent, suppress or reduce malodor development on body surfaces. In particular, the method allows to efficiently screen for compound having the ability of preventing sweat malodor development caused by volatile sulfur compounds (VSCs). The present invention is based on the finding of the direct precursor of naturally VSCs, which is present in human sweat and which will be metabolized by Staphylococci to VSCs.Type: GrantFiled: May 30, 2012Date of Patent: July 7, 2015Assignee: Firmenich SAInventors: Christian Starkenmann, Anthony Clark, Myriam Troccaz, Yvan Niclass
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Publication number: 20150126765Abstract: Compounds of the formula (I) wherein R2, A are certain substituents, Y is an ester group, a nitrile group or an amido group and Z is O, S or N?R2, and which compounds are, for example, useful as intermediates for pyrazole fungicides, can be prepared by the reaction of a compound of formula R2—C(O)—CH2Y, with an orthoformate HC—(OR3)3 in the presence of a base, especially in the presence of an amine, e.g.Type: ApplicationFiled: May 7, 2013Publication date: May 7, 2015Inventor: Janis Jaunzems
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Publication number: 20150045576Abstract: Unique methods have been developed to convert saccharides into value-added products such as alkyl lactates, lactic acid, alkyl levulinates, levulinic acid, and optionally alkyl formate esters and/or hydroxymethylfurfural (HMF). Useful catalysts include Lewis acid catalysts and Brønsted acid catalysts including mineral acids, metal halides, immobilized heterogeneous catalysts functionalized with a Brønsted acid group or a Lewis acid group, or combinations thereof. The saccharides are contacted with the catalyst in the presence of various alcohols.Type: ApplicationFiled: August 6, 2014Publication date: February 12, 2015Inventors: Herman P. Benecke, Daniel Garbark
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Patent number: 8299293Abstract: A method for preparing ?-keto acids, especially ?-ketomethionine, and/or derivatives thereof, whereby an aldehyde is reacted with thiols to give a corresponding dithioacetal, the dithioacetal formed, is reacted with an electrophile in the presence of a strong base, and the resulting ?,?-(dithio)carboxylic acid is solvolyzed with acid-catalysis to release thiol and give the ?-keto acid or a derivative thereof. Umpolung of aliphatic or aromatic aldehydes is effected by reaction with thiols.Type: GrantFiled: July 9, 2008Date of Patent: October 30, 2012Assignee: Evonik Degussa GmbHInventors: Christoph Kobler, Martin Hateley, Philipp Roth, Barbara Jaeger, Christoph Weckbecker, Klaus Huthmacher
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Patent number: 7566782Abstract: The present invention relates to a process for the preparation of rosuvastatin calcium, a promising new HMG-CoA reductase inhibitor.Type: GrantFiled: December 10, 2002Date of Patent: July 28, 2009Assignee: Ranbaxy Laboratories LimitedInventors: Yatendra Kumar, Hashim Nizar Poovanathil Nagoor Meeran, Shantanu De, Mohammad Rafeeq, Swargam Sathyanarayana
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Patent number: 7268250Abstract: A highly efficient process is provided for producing an optically active compound having high optical purity by an asymmetric reaction using as a catalyst a transition metal complex having an optically active nitrogen-containing compound as an asymmetric ligand.Type: GrantFiled: December 31, 2003Date of Patent: September 11, 2007Assignee: Kanto Kagaku Kabushiki KaishaInventors: Masahito Watanabe, Kunihiko Murata, Takao Ikariya
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Patent number: 7265240Abstract: A process for the carbonylation of ethylenically unsaturated compounds is described. The process comprises reacting an ethylenically unsaturated compound with carbon monoxide in the presence of a source of hydroxyl groups and a catalyst system. The catalyst system is obtained by combining: (a) metal of Group VIII or a compound thereof; and (b) a bidentate phosphine of general formula (I) The carbonylation reaction is carried out at a temperature of between ?30° C. to 49° C. and under a CO partial pressure of less than 30×105 N.Type: GrantFiled: August 4, 2003Date of Patent: September 4, 2007Assignee: Lucite International UK LimitedInventors: Graham R. Eastham, Cristina Jimenez, David Cole-Hamilton
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Patent number: 6946582Abstract: The present invention provides a process for producing a fluoroalkyl iodide represented by the general formula (II): Rf-CH2CH2I??(II) wherein Rf is a perfluoroalkyl or polyfluoroalkyl group comprising 1 to 20 carbons, the process comprising reacting hydrogen iodide gas with a fluoroalkene in the presence of a catalyst. The present invention also provides a process for producing a fluoroester by reacting the fluoroalkyl iodide with a carboxylate.Type: GrantFiled: November 20, 2002Date of Patent: September 20, 2005Assignee: Daikin Industries, Ltd.Inventors: Toshiyuki Katsube, Kouzou Noda, Jun Miki
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Patent number: 6541660Abstract: A process is proposed for preparing C5 acetate for Vitamin A synthesis by hydroformylation of 3,4-diacetoxybut-1-ene (3,4-DABE), according to which a 3,4-DABE is used which is obtained by acetoxylation of 1,3-butadiene with acetic acid and air in the presence of a catalyst and removing by distillation the 3,4-DABE formed in this case as by-product.Type: GrantFiled: March 27, 2002Date of Patent: April 1, 2003Assignee: BASF AktiengesellschaftInventors: Udo Rheude, Maximilian Vicari, Werner Aquila, Günter Wegner, Jörg Niekerken
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Patent number: 6515161Abstract: A hydroformylation process is disclosed which employs multidentate phosphite ligands in a catalyst composition. In particular, the ligands have heteroatom-containing substituents on the carbon attached to the ortho position of the terminal phenol group.Type: GrantFiled: August 30, 2000Date of Patent: February 4, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Kristina Ann Kreutzer, Wilson Tam, John Ronald Boyles, J Michael Garner
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Patent number: 6465680Abstract: A process for preparing a malonic acid monoester or &bgr;-ketoester from an epoxide includes the steps of reacting an epoxide with carbon monoxide and an alcohol in the presence of a catalytic amount of a cobalt compound and at least one promoter to produce a &bgr;-hydroxyester, separating the &bgr;-hydroxyester from the cobalt compound and the promoter, and oxidizing the &bgr;-hydroxyester to produce a malonic acid monoester or &bgr;-ketoester.Type: GrantFiled: June 20, 2001Date of Patent: October 15, 2002Assignee: Samsung Electronics Co., Ltd.Inventors: Byeong No Lee, In-Sun Jung, Eun Joo Jang
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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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Publication number: 20020052531Abstract: Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).Type: ApplicationFiled: February 16, 2001Publication date: May 2, 2002Inventors: Emilio E. Bunel, Patrick M. Burke, Joy D. Druliner, Leo E. Manzer, Kenneth G. Moloy, Manxue Wang
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Publication number: 20020035290Abstract: A process for preparing a malonic acid monoester or &bgr;-ketoester from an epoxide includes the steps of reacting an epoxide with carbon monoxide and an alcohol in the presence of a catalytic amount of a cobalt compound and at least one promoter to produce a &bgr;-hydroxyester, separating the &bgr;-hydroxyester from the cobalt compound and the promoter, and oxidizing the &bgr;-hydroxyester to produce a malonic acid monoester or &bgr;-ketoester.Type: ApplicationFiled: June 20, 2001Publication date: March 21, 2002Applicant: Samsung Electronics Co., Ltd.Inventors: Byeong No Lee, In-Sun Jung, Eun Joo Jang
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Patent number: 5932761Abstract: It is provided a process for industrially advantageously producing a branched aldehyde represented by the formula; ##STR1## ?wherein Y represents an acyl group of two or more carbon atoms; and X represents an acyloxymethyl group represented by --CH.sub.2 OY' (where Y' represents an acyl group of two or more carbon atoms), cyano group or an alkoxycarbonyl group! which is useful as an intermediate for pharmaceuticals and agricultural chemicals, comprising subjecting an olefinic compound represented by the following formula; ##STR2## (wherein Y and X are the same as defined above), to the reaction with hydrogen and carbon monoxide in the presence of a rhodium compound and a tertiary organic phosphorus compound with an electronic parameter (.upsilon.-value) of 2080 to 2090 cm.sup.-1 or with a steric parameter (.theta.-value) of 150 to 180.degree..Type: GrantFiled: March 23, 1998Date of Patent: August 3, 1999Assignee: Kuraray Co., Ltd.Inventors: Toshihiro Omatsu, Masahiko Kitayama, Takashi Onishi
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Patent number: 5670700Abstract: A hydroformylation process for the production of 5-formylvaleric acid from 2-, or 3-pentenoic acid, or 5-formylvaleric acid ester from 2-, or 3-pentenoic acid ester, or 5-formylvaleronitrile from 2-, or 3-pentenenitrile by reaction with hydrogen and carbon monoxide in a solvent containing a catalyst having a platinum component, a bidentate diaryl phosphine component, an acid promoter component.Type: GrantFiled: August 25, 1995Date of Patent: September 23, 1997Assignees: E. I. Du Pont de Nemours and Company, DSM, N.V.Inventors: Patrick Michael Burke, Onko Jan Gelling, Henk Oevering, Imre Toth
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Patent number: 5585524Abstract: Method for the preparation of an aldehyde in a process in which cobalt is being recycled by:(a) hydroformylating of an ethylenically unsaturated compound with carbon monoxide and hydrogen at a pressure higher than 5 MPa and a temperature higher than 80.degree. C. in the presence of a cobalt carbonyl compound in an organic phase, following which(b) removing cobalt from the organic phase by contacting the organic phase with a polar mixture, which mixture is substantially immiscible with the organic phase, first the pressure being reduced to a pressure lower than 5 MPa and simultaneously or afterwards cooling being applied down to a temperature below 80.degree. C.Type: GrantFiled: June 23, 1995Date of Patent: December 17, 1996Assignee: DSM N.V.Inventors: Otto E. Sielcken, Nicolaas F. Haasen
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Patent number: 5527950Abstract: The invention relates to a process for the preparation of a 5-formylvalerate ester by hydroformylating a mixture of pentenoate esters in the presence of a catalyst system which catalyst system comprises a metal from group 8-10 of the Periodic Table of Elements and a mono- or multidentate organic phosphorous ligand, wherein the mixture of pentenoate esters contains less than 500 ppm hydroperoxide compounds.Type: GrantFiled: December 28, 1994Date of Patent: June 18, 1996Assignees: DSM N.V., E.I. Du Pont de Nemours & Co.Inventors: Carolina B. Hansen, Antonius J. J. M. Teunissen
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Patent number: 5436356Abstract: A process for the carbonylation of ethylenically unsaturated compounds by reaction with carbon monoxide and a co-reactant in the presence of a substantially non-acidic catalyst system based on a palladium compound and a bidentate ligand of the formulaR.sub.1 R.sub.2 M.sub.1 RM.sub.2 R.sub.3 R.sub.4in which M.sub.1 and M.sub.2 may be phosphorus, arsenic or antimony atom, R is a bivalent organic bridging group, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently substituted or non-substituted aliphatic groups, with the proviso that R.sub.1 together with R.sub.2, and/or R.sub.3 together with R.sub.4 form a bivalent cyclic group with at least 5 ring atoms whereby the two free valencies are linked to M.sub.1 or M.sub.2, respectively.Catalytic compositions employing the bidentate ligands used in this method in which M.sub.1 and M.sub.2 are phosphorous are also presented.Type: GrantFiled: January 14, 1994Date of Patent: July 25, 1995Assignee: Shell Oil CompanyInventors: Eit Drent, Dennis H. L. Pello, Melis Hasselaar
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Patent number: 5264616Abstract: .omega.-Formyl-C.sub.4 -C.sub.20 -alkanecarboxylic esters are prepared by reacting C.sub.4 -C.sub.20 -alkenecarboxylic esters with carbon monoxide and hydrogen at from 30.degree. to 150.degree. C. and under from 0.01 to 30 bar in the presence of rhodium carbonyl complexes which are modified with polyphosphites.Type: GrantFiled: February 17, 1993Date of Patent: November 23, 1993Assignee: BASF AktiengesellschaftInventors: Michael Roeper, Peter M. Lorz, Dieter Koeffer
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Patent number: 5237097Abstract: A process is disclosed for the carbonylation of an organic compound selected from the group consisting of an olefin, an alcohol, an acid and an ester. In this process the organic compound is reacted with carbon monoxide in the presence of a Group VIII metal-containing catalyst. The liquid carbonylation product solution of this reaction is conveyed to a separation zone maintained at a lower total pressure than is the pressure in the reaction zone. Simultaneously with the conveyance of the liquid product solution to the separation zone is the introduction therein of a carbon monoxide-containing gaseous stream, the carbon monoxide therein contributing a partial pressure of up to 30 psia of the total pressure in said separation zone. A portion of the liquid carbonylation product solution is flashed and removed from the separation zone. The unflashed liquid carbonylation product solution is recycled back into the reaction zone.Type: GrantFiled: December 22, 1992Date of Patent: August 17, 1993Assignee: Quantum Chemical CorporationInventors: David W. Smith, Ronnie M. Hanes
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Patent number: 5107015Abstract: The preparation of 2-formyl-2-methyl succinates by reacting itaconates with carbon monoxide and hydrogen in contact with a catalyst system comprising rhodium and a tertiary phosphorus compound, wherein the reaction is carried out under a pressure of from 90 to 325 bar.Type: GrantFiled: October 24, 1990Date of Patent: April 21, 1992Assignee: BASF AktiengesellschaftInventors: Werner Bertleff, Gerhard Butz
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Patent number: 5091559Abstract: A process is disclosed for forming alkyl 4-oxobutyrates and its acetals which comprises reacting under anhydrous conditions acrolein or its acetals with carbon monoxide and an alcohol of the formula R OH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier and a promoting effective amount of hydrogen halide. An intermediate in the process, i.e., .beta.-halopropionaldehyde or acetal thereof can also be used in forming alkyl 4-oxobutyrates and acetals thereof by reacting under anhydrous conditions said .beta.-halopropionaldehyde or its acetals with carbon monoxide and an alcohol of the formula ROH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier.Type: GrantFiled: February 8, 1988Date of Patent: February 25, 1992Assignee: Quantum Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5072005Abstract: Methyl 4-oxobutyrate and its methanol addition products, methyl 4,4-dimethoxybutyrate and gamma-methoxy-gamma-butyrolactone, which are useful as intermediates in the preparation of such industrially important compounds as gamma-butyrolactone, 1,4-butanediol and glutamic acid, are produced from the reaction of acrolein, carbon monoxide and methanol in the presence of a catalyst system which consists of (a) a Group VIII metal component selected from palladium metal or a palladium-containing composition which generates palladium metal under reaction conditions, (b) a hydrogen halide and (c) an arylarsine catalyst copromoter.Type: GrantFiled: July 9, 1987Date of Patent: December 10, 1991Assignee: National Distillers and Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 4950429Abstract: 6-Aminocaproic acid is prepared by(a) reacting a 5-formylvaleric acid ester with water in the presence of an acid agent at 30.degree.-200.degree. C. and(b) reacting the 5-formylvaleric acid thus obtained with excess ammonia and hydrogen in the presence of a hydrogenation catalyst and of a solvent which is inert under the reaction conditions at 50.degree.-150.degree. C. under superatmospheric pressure.Type: GrantFiled: March 23, 1989Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Uwe Vagt, Rolf Fischer, Franz Merger, Hans-Martin Hutmacher
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Patent number: 4945179Abstract: Process for the preparation of esters of carboxylic acids by contacting an olefinically unsaturated compound with CO and an alcohol, in the presence of (a) a ruthenium compound and (b) an iodide salt, LiBr and/or an onium bromide, with a molar ratio of CO to olefinically unsaturated compound.ltoreq.2.0 being applied when "b" is an iodide salt.Type: GrantFiled: August 15, 1988Date of Patent: July 31, 1990Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4849542Abstract: A process for the preparation of oxo-alkanedioic acids or diesters thereof by reacting an alkenoic acid or an ester thereof, at least one of the C atoms of the carbon carbon double bond carrying a H atom, with CO and H.sub.2 in the presence of a catalytic system prepared by combining:a. Pd and/or a Pd compound,b. a compound containing an anion of an acid having a pKa of less than 2, except hydrohalogenic acid and carboxylic acids, andc. a bidentate ligandR.sup.1 R.sup.2 --M--R--M--R.sup.3 R.sup.4wherein M is P, As or Sb, R is a divalent organic bridging group having at least two C atoms in the bridge, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are optionally substituted hydrocarbon groups.Type: GrantFiled: October 28, 1986Date of Patent: July 18, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4849543Abstract: This invention concerns a process for the production of diesters by hydroformylation/Michael addition of alkyl acrylates, which comprises contacting the alkyl acrylate with carbon monoxide and hydrogen in the presence of a catalyst system comprising a rhodium-containing compound, excess phosphine-containing ligand, a nitrogen-containing compound and a solvent at a temperature of 70.degree.-150.degree. C. and a pressure of 500-4000 psi.Type: GrantFiled: November 15, 1985Date of Patent: July 18, 1989Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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Patent number: 4837356Abstract: Methyl-4-ketohexanoate is prepared by reacting methyl acrylate, ethylene, carbon monoxide and a secondary alcohol, e.g. a secondary alcohol having 3 to 20 carbon atoms, in the presence of a catalyst comprising a complex combination of rhodium, carbon monoxide and triorganophosphorus.Type: GrantFiled: October 23, 1987Date of Patent: June 6, 1989Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
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Patent number: 4664851Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transistion metal or Group II metal iodides or bromides, and containing a trivalent nitrogen compound containing a group ##STR1## (X=O or S), such as an amide, a carbamate, a urea or a derivative thereof.Type: GrantFiled: July 19, 1982Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4647691Abstract: Ethyl and n-propyl esters of carboxylic acids are prepared in good yield from methanol, syngas and a carboxylic acid by contacting a mixture of the carboxylic acid, carbon monoxide, hydrogen and methanol with a catalyst composition comprising a ruthenium-containing compound, a cobalt-containing compound and a quaternary onium salt or base, and heating the resulting mixture at an elevated temperature and pressure for sufficient time to produce the desired ethyl and propyl esters, and then recovering the same from the reaction mixture.Type: GrantFiled: January 13, 1982Date of Patent: March 3, 1987Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton
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Patent number: 4640802Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, a phosphine oxide and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transition metal or Group II metal iodides or bromides, and containing a tertiary phosphine oxide.Type: GrantFiled: July 7, 1982Date of Patent: February 3, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4545934Abstract: Process for the production of 4-substituted acetoacetic acid derivatives. An acetoacetic acid derivative having the formula: ##STR1## wherein R is alkoxy having 1 to 6 C atoms, phenoxy, --NR'.sub.2, wherein R' is alkyl having 1 to 6 C atoms or aryl, or NR'.sub.2, which is azetidine, pyrrolidine or piperidine, is treated with a secondary amine at an elevated temperature and in the presence of an organic solvent. The water formed is separated. The intermediate is converted into the corresponding 3-enamine carboxylic acid derivative. The derivative is converted by treatment with sodium amide in liquid ammonia into the corresponding sodium salt. The sodium salt is converted by treatment with a halogen compound having the formula R.sub.1 CH.sub.2 X or R.sub.1 R.sub.2 CHX, wherein R.sub.1 and R.sub.2 each are alkyl, alkenyl, alkinyl or aryl and X is chlorine, bromine or iodide, into the corresponding 4-substituted enamino derivative. The derivative is hydrolyzed into the 4-substituted acetoacetic acid derivative.Type: GrantFiled: March 21, 1984Date of Patent: October 8, 1985Assignee: Lonza Ltd.Inventors: Felix Previdoli, Leander Tenud
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Patent number: 4518793Abstract: Disclosed is a process for preparing an acetone dicarboxylic acid diester, which comprises allowing diketene, carbon monoxide and a nitrous acid ester to react in the presence of a palladium halide or a complex thereof.Type: GrantFiled: October 17, 1983Date of Patent: May 21, 1985Assignee: UBE Industries, Ltd.Inventors: Shinichiro Uchiumi, Kikuo Ataka
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Patent number: 4360692Abstract: An improved process for the preparation of alkyl formylvalerates, wherein butadiene or a butadiene-containing hydrocarbon mixture is reacted, in a first stage, with carbon monoxide and alkanols in the presence of cobalt carbonyl complexes and, per mole of butadiene, from 0.5 to 2 moles of tertiary nitrogen bases having a pK.sub.a of from 3 to 11, at from 80.degree. to 150.degree. C. and from 300 to 2,000 bar, and, in a second stage, the resulting alkyl pentenoate is reacted with carbon monoxide and hydrogen in the presence of cobalt carbonyl complexes at from 100.degree. to 160.degree. C.Type: GrantFiled: November 10, 1980Date of Patent: November 23, 1982Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Heinz-Walter Schneider
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Patent number: 4334042Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.Type: GrantFiled: July 23, 1979Date of Patent: June 8, 1982Assignee: Kuraray Co. Ltd.Inventors: Mitsuo Matsumoto, Masuhiko Tamura
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Patent number: 4255591Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.Type: GrantFiled: November 20, 1978Date of Patent: March 10, 1981Assignee: Monsanto CompanyInventors: Earle C. Makin, Jerry L. Price, Yu W. Wei
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Patent number: 4209467Abstract: A hydroformylation process in which the catalyst is the reaction product of a cobalt carbonyl compound with a nitrogen-containing heterocyclic compound having an enolic hydroxyl group on the carbon atom adjacent to the ring-forming nitrogen atom or the catalyst is the reaction product of a .beta.-dioxo cobalt compound and a nitrogen-containing base having a double bonded carbon atom at the .alpha.-position, with carbon monoxide and hydrogen.Type: GrantFiled: January 2, 1979Date of Patent: June 24, 1980Assignee: Daicel Ltd.Inventors: Hidetaka Kojima, Shingo Oda, Takushi Yokoyama, Yasukazu Murakami
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Patent number: 4052461Abstract: The invention relates to a process for the preparation of aldehydes by the hydroformylation of olefinically unsaturated compounds using a rhodium catalyst which catalyst is provided by (1) introducing rhodium into the reaction solution in the form of an ionic rhodium compound, the said ionic compound consisting of (a) a rhodium-containing cation having rhodium complexed with ligands other than halide, and (b) a non-coordinating anion; and (2) furnishing to the reaction solution at least two moles of a modifying ligand per mole of ionic rhodium compound where the modifying ligand is furnished either pre-coordinated in the said ionic rhodium compound or as a free compound, and where the modifying ligand is a tertiary organo phosphorous compound having from 3 to 90 carbon atoms, or a tertiary organo arsenic compound having from 3 to 90 carbon atoms, or a tertiary organo antimony compound having from 3 to 90 carbon atoms.Type: GrantFiled: April 4, 1975Date of Patent: October 4, 1977Assignee: Monsanto CompanyInventors: Harold Burnham Tinker, Donald E. Morris