Preparing Esters By Esterification Or Carbonylation Patents (Class 560/204)
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Patent number: 5436365Abstract: A method is provided for the preparation of a pimelic ester of the formula: ##STR1## wherein R.sup.1 and R.sup.2 may be identical or different, and are linear or branched saturated alkyl substituents having from 1 to 10 carbons or araliphatic radicals having 7 to 10 carbon atoms; R.sup.3 is H or a hydrocarbon radical of one to six carbon atoms, and n is an integer of from 0 to 3; wherein the method entails:reacting a salt, formed from reaction of a 2-oxocyclohexanecarboxylic ester with a strong base, with an alcohol at a temperature of 50.degree.-250.degree. C., to cause ring opening.Type: GrantFiled: September 12, 1994Date of Patent: July 25, 1995Assignee: Huels AktiengesellschaftInventor: Gunther Kohler
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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: 5420336Abstract: Copper and vanadium catalyst components are recovered and dialkyl esters of dicarboxylic acids are synthesized by precipitating the catalyst metals with an alcohol selected from the group consisting of methanol, ethanol, and isopropanol removal of the precipitate, and then heating the mixture.Type: GrantFiled: November 2, 1994Date of Patent: May 30, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Howard W. Anderson, James E. Matush, Brent G. Sparks, Eugene D. Wilhoit
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Patent number: 5397488Abstract: The invention provides a composition comprising Formula I as shown below and at least one selected from the group consisting of Formulae II, III, IV, and V as shown below: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different, and comprise alkyl groups containing no tertiary carbon and having from about 4 to about 15 carbon atoms. The composition of the invention is useful as a lubricant stock. A method for synthesizing the composition is also disclosed.Type: GrantFiled: December 9, 1993Date of Patent: March 14, 1995Assignee: Mobil Oil CorporationInventors: Catherine S. H. Chen, Suzanne E. Schramm, Steven E. Wentzek
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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: 5304674Abstract: The invention relates to a direct process for the preparation of alkanedioic derivatives, for example alkanedioic diesters, by reaction of an aliphatic conjugated diene such as butadiene with carbon monoxide and a hydroxyl group-containing compound such as a C.sub.1-6 alkanol in the presence of a catalyst system containinga) a source of cationic palladium,b) a first bidentate diphosphine ligand having electron-withdrawing substituents on the phosphorus atoms,c) a second bidentate diphosphine ligand having electron-releasing substituents on the phosphorus atoms, andd) a source of an anion.Type: GrantFiled: June 24, 1993Date of Patent: April 19, 1994Assignee: Shell Oil CompanyInventor: Eit Drent
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Fatty alkoxylate esters of aliphatic and aromatic dicarboxylic and tricarboxylic acids as emollients
Patent number: 5302377Abstract: Fatty alkoxylate esters which are diesters or triesters of an aliphatic or aromatic dicarboxylic or tricarboxylic acid formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols. Compositions for topical application are also disclosed including one or more active ingredients, water and an emollient agent of the fatty alkoxylate esters of the present invention.Type: GrantFiled: April 2, 1992Date of Patent: April 12, 1994Assignee: Croda, Inc.Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr. -
Patent number: 5254722Abstract: A process for the production of triglycerides of C.sub.1 -C.sub.4 alkyl esters of C.sub.6 -C.sub.22 fatty acids:a) where dry sodium carbonate catalyst is dissolved in glycerol and mixed with a molar excess of preferably the methyl ester of C.sub.6 -C.sub.22 fatty acid at a temperature between about 150.degree. C. and 250.degree. C. at less than atmospheric pressure and under substantially anhydrous conditions to produce an initial reaction mixture containing the corresponding triglycerides of said fatty acids, and partially reacted glycerol with unreacted hydroxyl groups (OH values 10-40),b) thereafter, a portion of the initial reaction mixture is reacted with additional C.sub.1 -C.sub.4 alkyl ester of C.sub.6 -C.sub.22 fatty acid under conditions to achieve substantially full conversion of said unreacted hydroxyl groups (OH values of 5 or less), andc) a product containing the corresponding triglycerides of said fatty acids is separated from unreacted alkyl ester and from the sodium carbonate catalyst.Type: GrantFiled: May 19, 1988Date of Patent: October 19, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Eberhard Peukert, Horst Rutzen, Gerhard Wollmann
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Patent number: 5248727Abstract: Thermoplastic molding compositions of a vinyl chloride polymer and one or more emulsion polymers made with special emulsifiers have improved properties for technical application, such as reduced fogging. They are used for the production of molded articles, sheet products and films.Type: GrantFiled: May 18, 1992Date of Patent: September 28, 1993Assignee: Bayer AktiengesellschaftInventors: Christian Lindner, Adolf Schmidt, Herbert Eichenauer, Karl-Erwin Piejko, Karl-Heinz Ott
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Patent number: 5245072Abstract: This invention relates to processes for making biodegradable surfactant. The process comprises several steps including an optional step. The first step is directed to reacting olefins with ZSM-23 catalyst to form oligomers having the formula -(C.sub.3).sub.x, (C.sub.4).sub.x or mixtures thereof. Second, the oligomer is hydroformylated to form a saturated alcohol, for example, tridecanol. Next, the saturated alcohol is ethoxylated. Thereafter a nonionic biodegradable surfactant is recovered. This surfactant can be used in detergent formulations. A process is also taught for making esters which can be used as lubricants or plasticizers. A specific hydroformylation process is taught which utilizes modified cobalt carbonyl catalyst. Also, a specific ethoxylation process is taught. Products formed according to the latter two processes as well as their uses are also taught.Type: GrantFiled: February 24, 1992Date of Patent: September 14, 1993Assignee: Mobil Oil CorporationInventors: Thomas J. Giacobbe, George A. Ksenic
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Patent number: 5235087Abstract: Dialkyl carbonates can be prepared by reacting carbon monoxide with alkyl nitrites over a modified platinum metal supported catalyst at an elevated temperature in a continuous gas phase reaction, the reaction being carried out with the exclusion of additional oxidizing substances and, if appropriate, the presence of a lower alcohol.Type: GrantFiled: June 20, 1991Date of Patent: August 10, 1993Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Heinz Landscheidt, Heinz U. Blank, Walter Kipshagen
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Patent number: 5233078Abstract: The invention relates to a process for preparing dialkyl malonates by ozonolysis of diketene, subsequent catalytic hydrogenation and esterification of the reaction products, the by-products being alkyl formates and dialkyl acetals.Type: GrantFiled: June 4, 1992Date of Patent: August 3, 1993Assignee: BASF AktiengesellschaftInventors: Ludwig Schuster, Klaus Halbritter
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Patent number: 5225429Abstract: Fluorinated arachidonic derivatives are 5-lipoxygenase inhibitors which have the useful pharmacologic activity as antiallergy and anti-inflammatory agents and are useful for treating, for example, asthma, anaphylaxis, allergy, rheumatoid arthritis, and psoriasis and cardiovascular diseases.Type: GrantFiled: June 24, 1991Date of Patent: July 6, 1993Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Jean-Bernard Ducep, Jean-Francois Nave, Detlef Jacobi
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Patent number: 5218140Abstract: A process and novel catalyst for the carbonylation of one or more of alcohols, ethers and ether alcohols to esters and, optionally, to carboxylic acids. The reaction is effected in the vapor state over a solid catalyst comprising a polyoxometalate anion in which the metal is at least one taken from Group V and VI of the Periodic Chart of the Elements complexed with a cation from a member of Group VIIIA of the Periodic Chart of the Elements. Preferably, the catalyst is deposited on a support that is inert to the reaction. The preferred support is silica.Type: GrantFiled: August 2, 1988Date of Patent: June 8, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Richard W. Wegman
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Patent number: 5216072Abstract: A process comprising the direct addition of a halogenated carboxylic acid to an olefin-containing compound is disclosed, as well as the resulting adduct and saponified adduct.Type: GrantFiled: April 17, 1990Date of Patent: June 1, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Young H. Kim
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Patent number: 5214199Abstract: A malonic monoester is prepared in a good yield by a single step reaction by reacting malonic acid with an alcohol in the presence of a base and an activator of malonic acid selected from the group consisting of an acyl halide or halocarbonate and an acid anhydride or dicarbonate.Type: GrantFiled: August 30, 1991Date of Patent: May 25, 1993Assignee: Kanegafuchi Chemical Industries Co., Ltd.Inventors: Teruyoshi Koga, Noboru Ueyama, Kenji Inoue, Satomi Takahashi
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Patent number: 5210280Abstract: A process for the preparation of alkanedioic acid derivatives comprising reacting an alkenoic acid derivative with carbon monoxide and a nucleophilic compound having a mobile hydrogen atom in the presence of a catalyst system comprising a source of a Group VIII metal, a source of a bidentate diphosphine liquid, a source of an anion and a source of a quinone promoter.Type: GrantFiled: February 19, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5210222Abstract: A process, which is harmless with respect to safety, for the production of malonic acid anhydride. For this purpose, diketene is ozonized in the presence of a suitable carbonyl compound. Malonic acid anhydride is a highly reactive intermediate product for the synthesis of numerous active ingredients for, e.g., pharmaceutical agents, pesticides or dyes.Type: GrantFiled: January 21, 1992Date of Patent: May 11, 1993Assignee: Lonza Ltd.Inventor: Colm O'Murchu
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Patent number: 5198573Abstract: Diesters of hexene-1,6-dioic acids are prepared by reacting at least one 1,2-dialkoxy-3-butene with carbon monoxide in the presence of a catalytically effective amount of a palladium-based catalyst and a halogen compound, in liquid phase, at elevated temperature and at superatmospheric pressure.Type: GrantFiled: September 19, 1991Date of Patent: March 30, 1993Assignee: Rhone-Poulenc ChimieInventors: Helene Deweerdt, Jean Jenck, Philippe Kalck, Sylvain Mutez, Robert Perron
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Patent number: 5189198Abstract: A process for efficiently preparing an unsaturated dicarboxylic acid diester, which comprises reacting a conjugated diene, carbon monoxide, an alcohol and oxygen in the presence of a catalyst comprising (a) a platinum metal, a salt thereof or a complex compound of a platinum metal, (b) at least one metal salt selected from the group consisting of a copper salt, an iron salt and a manganese salt and (C) at least one compound selected from the group consisting of (1) an alkali metal compound or an alkaline earth metal compound, (2) a rare earth metal compound, (3) a metal compound of the groups IIIA, IVA, IVB, VA, VB or VIA, and (4) a metal carbonyl complex. The unsaturated dicarboxylic acid diester is useful as an intermediate material in industrial chemical processes and can be efficiently prepared without the use of a dehydrating agent.Type: GrantFiled: May 6, 1991Date of Patent: February 23, 1993Assignee: Idemitsu Petrochemical Co., Ltd.Inventors: Takashi Kumazawa, Tetsuo Ishibashi, Mitsugu Kanzawa
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Patent number: 5187308Abstract: The present invention relates to a novel process for the production of low viscosity copolymers of maleic acid monoalkyl ester and vinyl alkyl ethers characterized in that the copolymerization of alkyl vinyl ether is performed with a mixture composed of maleic acid anhydride and maleic acid monoalkyl ester. The specific viscosity is controlled by the setting of a certain maleic acid anhydride to maleic acid monoalkyl ester ratio.Type: GrantFiled: November 14, 1990Date of Patent: February 16, 1993Assignee: Giulini Chemie GmbHInventors: Zvi Pelah, Istvan Potencsik, Werner Kopp, Ernst Urmann
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Patent number: 5159107Abstract: A process for the continuous preparation of alkyl pentenoates comprises the following steps:a) reaction of a butadiene-containing C.sub.4 cut with an alkanol and carbon monoxide in the presence of a cobalt carbonyl catalyst and heterocyclic aromatic tertiary nitrogen base at from 100.degree. to 160.degree. C. and under from 100 to 1,200 bar andb) treatment of the resulting reaction mixture, at the rate at which it is obtained, in a treatment zone, at from 100.degree. to 160.degree. C. under from 250 to 1,200 bar with a residence time of from 5 to 60 minutes, substantially without back-mixing.Type: GrantFiled: October 29, 1991Date of Patent: October 27, 1992Assignee: BASF AktiengesellschaftInventors: Paul Panitz, Heinrich Reitz, Gunter Schuch, Wilfried Seyfert
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Patent number: 5145861Abstract: Fluorinated arachidonic derivatives are 5-lipoxygenase inhibitors which have the useful pharmacologic activity as antiallergy and anti-imflammatory agents and are useful for treating, for example, asthma, anaphylaxis, allergy, rheumatoid arthritis, and psoriasis.Type: GrantFiled: August 5, 1991Date of Patent: September 8, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Jean B. Ducep, Jean-Francois Nave
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Patent number: 5130470Abstract: A process for polymerizing tetrahydrofuran using a fluorinated resin containing sulfonic acid groups a trifluoromethane sulfonic acid as catalyst and a mixture of maleic acid and maleic anhydride as weight control agent. The product has the formula ##STR1## which can be hydrogenated to produce polytetramethylene ether glycol. The preferred molecular weight range of the polytetramethylene ether glycol is 600 to 4,000.Type: GrantFiled: March 27, 1991Date of Patent: July 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Willard L. Quon, Kirk M. Schall, Gary A. Hida
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Patent number: 5112507Abstract: Novel copolymers of unsaturated acidic reactants and high molecular weight olefins wherein at least 20 percent of the total high molecular weight olefin comprises the alkylvinylidene isomer are useful as dispersants in lubricating oils and fuels and also may be used to prepare polysuccinimides and other post-treated additives useful in lubricating oils and fuels.Type: GrantFiled: September 29, 1989Date of Patent: May 12, 1992Assignee: Chevron Research and Technology CompanyInventor: James J. Harrison
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Patent number: 5087730Abstract: A method for producing an ester, which comprises reacting an organic acid or its anhydride with an alcohol in the presence of a catalyst of an organometallic compound, wherein an esterification reaction product containing the catalyst, is treated with a polyhydric alcohol.Type: GrantFiled: June 15, 1990Date of Patent: February 11, 1992Assignee: Mitsubishi Kasei Vinyl CompanyInventor: Yasunori Matsushita
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Patent number: 5087735Abstract: Hexenedioic acid diesters, e.g., a hex-3-ene-1,6-dioic acid diester, are prepared by reacting carbon monoxide and an alcohol with at least one diacyloxylated butene in a polar, aprotic, basic solvent, in the presence of a catalytically effective amount of palladium values and at least one inorganic halide, the cation of which halide being an alkali or alkaline earth metal and the anion thereof being a chloride or bromide.Type: GrantFiled: December 13, 1990Date of Patent: February 11, 1992Assignee: Rhone-Poulenc ChimieInventor: Philippe Denis
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Patent number: 5081292Abstract: .beta., .gamma.-Unsaturated carboxylic acids, e.g., 3-hexene-1,6-dioic acid, are selectively prepared by carbonylating (with carbon monoxide) an allyl alcohol, e.g., a butenediol, at an elevated temperature and under superatmospheric pressure, in the presence of a catalytically effective amount of a palladium-based catalyst and at least one quaternary onium chloride of one of the Group VB elements nitrogen or phosphorus, such element being tetracoordinated via carbon atoms and with the proviso that such nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: April 30, 1990Date of Patent: January 14, 1992Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Jean Jenck, Robert Perron
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Patent number: 5077425Abstract: A process for the hydrocarboxylation of alkenes and non-conjugated olefinically unsaturated nitriles and esters using a rhodium catalyst, a bromide or iodide promoter, and a nitrile accelerator.Type: GrantFiled: April 2, 1990Date of Patent: December 31, 1991Assignee: E. I. du Pont de Nemours and CompanyInventor: Patrick M. Burke
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Patent number: 5077433Abstract: The hexene-1,6-dioic acids, e.g., hex-3-ene-1,6-dioic acid, are prepared by reacting carbon monoxide and water with at least one diacyloxylated butene, in the presence of a catalytically effective amount of palladium and at least one quaternary onium chloride of one of the Group VB elements nitrogen or phosphorus, such element being tetracoordinated via carbon atoms and with the proviso that such nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: April 30, 1990Date of Patent: December 31, 1991Assignee: Rhone-Poulenc ChimieInventors: Jean Jenck, Philippe Denis, Philippe Kalck, Helene Deweerdt
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Patent number: 5073570Abstract: The new compositions of matter of the present invention comprise compounds having one of the following formulas: ##STR1## wherein: R is hydrogen or methyl;n is 1 to 16;R.sub.1 and R.sub.2 are defined as R.sub.3 and R.sub.4 below or are joined to form a cycloalkyl, cycloalkenyl, aromatic or a heterocyclic ring containing an oxygen, nitrogen or sulfur atom or an alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl substituted derivative thereof;R.sub.3 and R.sub.4 are independently selected from (A) hydrogen, alkyl, cycloalkyo, alkenyl, cycloalkenyl, aryl, a heterocyclic ring containing an oxygen, nitrogen or sulfur atom, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl and (B) substituted derivatives of the alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl and the heterocyclic ring wherein the substitutions are alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl;W may be a single bond, oxygen, NR.sub.5, or (CR.sub.6 R.sub.7).Type: GrantFiled: February 16, 1989Date of Patent: December 17, 1991Assignee: Lonza Inc.Inventor: Chuen-Ing J. Tseng
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Patent number: 5055609Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction tests results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: April 6, 1990Date of Patent: October 8, 1991Assignee: Morflex, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 5028734Abstract: A process for the selective carbonylation of a conjugated diene by contacting with carbon monoxide in the presence of a hydroxyl-group-containing compound such as water, alcohol, phenol or carboxylic acid in liquid phase using a catalyst system formed by the combination of:(a) a palladium compound and(b) at least one organic bidentate phosphine.Type: GrantFiled: January 27, 1989Date of Patent: July 2, 1991Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5026900Abstract: A process for the preparation of alkyl malonates by carbonylation of chloroacetate in the presence of a carbonyl source, a carbonylation catalyst, such as chromium carbonyl and an aliphatic alcohol, this reaction being carried out in a two-phase liquid medium.A process for recycling the catalyst also forms part of the invention.Type: GrantFiled: May 18, 1989Date of Patent: June 25, 1991Assignee: Rhone-PoulencInventors: Philippe Coste, Philippe Leconte, Robert Perron, Michel Baudoin
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Patent number: 5023368Abstract: Aminophosphonate-containing polymers of the formula:--B].sub.m [A].sub.nwhereinA represents repeating units from one or more ethylenically unsaturated comonomers;B is ##STR1## wherein R is hydrogen or methyl,X is hydrogen or an alkali metal,Z is CH.sub.2 --P(O)(OX).sub.2 or C.sub.1 -C.sub.6 alkyl, aryl, cyclohexyl or alkaryl, m/n is 0.01 to 0.5.The novel polymers of the present invention may be used as dispersants for concentrated aqueous particulate slurries, and as corrosion inhibitors and scale inhibitors in water treatment.Type: GrantFiled: June 8, 1989Date of Patent: June 11, 1991Assignee: National Starch and Chemical Investment Holding CorporationInventors: John C. Leighton, Carmine P. Iovine
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Patent number: 5015759Abstract: A process for increasing the direct esterification reaction rate between a diacid and 1,4-butanediol and for directly esterifying greater than 95% of the acid ends of the diacid by mixing in any order the diacid, the 1,4-butanediol and a catalyst compound selected from organo-titanium, organo-tin, and organo-zirconium compounds, to form a reaction mixture wherein the ratio of diol:diacid is at least 2:1 and then reacting the reaction mixture at an average temperature ranging between 190.degree. C. to 200.degree. C. for a period of time no longer than sixty minutes. The same process may be followed substituting ethylene glycol for 1,4-butanediol, provided the catalyst compound is added neat, further provided that the average reaction temperature ranges from 190.degree. C. to 200.degree. C., and also provided that the reaction mixture be reacted for a period of time no longer than seventy minutes.Type: GrantFiled: December 8, 1989Date of Patent: May 14, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: David J. Lowe
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Patent number: 5004569Abstract: The invention relates to a process for the production of carboxylic acid esters from carboxylic acids and alcohols which is characterized in that neutral phosphites containing oxetane groups are used as esterification catalysts.Type: GrantFiled: December 6, 1988Date of Patent: April 2, 1991Assignee: Bayer AktiengesellschaftInventors: Helmut-Martin Meier, Klaus Kircher, Klaus Berg
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Patent number: 4990652Abstract: The reaction products of the alpha-halogenated half esters or amides of succinic acid and thiadiazole dimercaptides as new compositions of matter and their use as lubricant additives possessing multifunctional properties such as extreme pressure, antiwear, antioxidant and anticorrosion.Type: GrantFiled: November 21, 1989Date of Patent: February 5, 1991Assignee: Atochem North America, Inc.Inventors: James P. King, Sameeh S. Toukan
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Patent number: 4990458Abstract: A process for forming derivatives of organic compounds as a step during their analysis. A macroreticular resin is used as both an adsorbent for the analyte and the derivatizing reagent and also as a catalyst for the derivatization reaction. Subsequent serial elution of the absorbed compounds leads to simple separation of the derivatized analyte from the starting materials. Further, the resin impregnated with derivatizing reagent can be used to combine the extraction and derivatization of the analyte. As macroreticular resins are relatively inexpensive, they result in reduced costs compared with conventional catalysts, and their ease of separation from liquid systems makes them easy to use and makes it possible to automate the procedure.Type: GrantFiled: September 22, 1987Date of Patent: February 5, 1991Assignee: McMaster UniversityInventor: Jack M. Rosenfeld
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Patent number: 4960926Abstract: Process for the carbonylation of olefinically unsaturated compounds with carbon monoxide in the presence of a hydroxyl-group-containing compound, a palladium catalyst, an organic phosphine, an acid with a pKa value <2, with the exception of halogen acids and carboxylic acids as promoter, and a catlayst stabilizer selected from the group consisting of compounds of the general formula; ##STR1## wherein X represents an element of group Va with a valency greater than 3, selected from P. As or Sb, where Y represents an element of group VIa, selected from O, S or Se, and where either a, b and c are 0 or 1, where R.sub.4, R.sub.5 and R.sub.6 are the same or different and represent hydrocarbon groups, or a and b=0 and c=0 or 1 and R.sub.4 and R.sub.5 together with X form a heterocyclic group, or a, b and c=0 and R.sub.4, R.sub.5 R.sub.6 together with X form a heterocyclic group, compounds of the general formula: ##STR2## wherein R.sub.7 is a hydrocarbon group and where R.sub.8 and R.sub.Type: GrantFiled: July 27, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4960925Abstract: A number of novel peracid precursors each have the general structure: ##STR1## wherein: Z is a leaving group, the conjugate acid of the leaving group being in the range of from about 4 to 15; R is a substituted or unsubstituted alkyl or alkenyl group having from about 1 to 18 carbon atoms; and M is hydrogen or an alkali or alkaline earth metal. A method is also disclosed for synthesizing a product as represented above wherein succinic anhydride, including an R constituent as defined above is dissolved in a water-miscible, non-nucleophilic solvent and an acid including a Z constituent as defined above is neutralized and deprotonated to form a nucleophile, the substituted anhydride and the nucleophile being combined to form the product. The product is a component in a dry bleach product, optionally including other adjuncts.Type: GrantFiled: October 24, 1988Date of Patent: October 2, 1990Assignee: The Clorox CompanyInventors: Dale S. Steichen, Hao Ku, Sheldon N. Lewis
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Patent number: 4946029Abstract: Carboxylic esters obtained by reacting olefinically unsaturated compounds with carbon monoxide and alcohols and containing aldehydes, acetals and/or unsaturated compounds are purified by(a) treating the carboxylic ester which contains an aldehyde, acetal or unsaturated compound in a first stage at from 20.degree. to 200.degree. C. with a strongly acidic agent and(b) hydrogenating the mixture thus treated in a second stage at from 50.degree. to 200.degree. C. under a pressure of from 1 to 50 bar in the presence of one or more metals of subgroup VIII of the periodic table and(c) removing low and high boilers from the hydrogenated mixture obtained in stage b by distillation and obtaining a pure carboxylic ester.Type: GrantFiled: February 24, 1989Date of Patent: August 7, 1990Assignee: BASF AktiengesellschaftInventors: Gerhard Frank, Hubert Lendle, Wilfried Seyfert, Peter Stops
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Patent number: 4935488Abstract: Novel trimethylolheptanes having three highly reactive hydroxyl groups are provided. They are useful as raw materials for the production of polyesters for use in or as raw materials or modifiers for paints, inks, adhesives, coating compositions and molding resins. Uses for the trimethylolheptanes are also provided.Type: GrantFiled: April 20, 1989Date of Patent: June 19, 1990Assignee: Kurary Company, Ltd.Inventors: Toshihiro Omatsu, Yasuo Tokitoh, Noriaki Yoshimura, Masao Ishida, Makoto Yano, Koji Hirai, Yoichi Matsumoto, Keiji Kubo
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Patent number: 4931583Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction test results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: June 15, 1989Date of Patent: June 5, 1990Assignee: Morflex Chemical Compay, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 4927959Abstract: Novel alprenolol derivatives represented by the formula: ##STR1## wherein R is ##STR2## and hydrochlorides thereof are disclosed.Type: GrantFiled: September 2, 1988Date of Patent: May 22, 1990Assignee: Snow Brand Milk Products Co., Ltd.Inventors: Shinichi Shimada, Noboru Kawaguchi, Tadayoshi Koyama, Akinori Wakaiki, Keiji Hayashi, Yasuyoshi Takeshita, Masamichi Nakakoshi, Gosei Kawanishi
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Patent number: 4925972Abstract: Alkyl pentenoates are prepared by(a) reacting butadiene or a butadiene-containing hydrocarbon mixture with carbon monoxide and an alkanol in the presence of a tertiary aromatic heterocyclic nitrogen base and a cobalt carbonyl catalyst at from 80.degree. to 160.degree. C. under from 100 to 1,000 bar to obtain a reaction mixture which contains alkyl pentenoate, C.sub.6 -diester, tertiary nitrogen base, alkanol, butadiene, hydrocarbon and by-product,(b) substantially removing from the reaction mixture obtained any excess hydrocarbon, nitrogen base, alkanol and alkyl pentenoate by distillation to obtain a residue which contains cobalt carbonyl catalyst,(c) bringing the residue which contains cobalt carbonyl catalyst into contact with a mixture of carbon monoxide and hydrogen at elevated temperature and elevated pressure, and(d) recycling the residue which contains cobalt carbonyl catalyst into alkyl pentenoate synthesis stage (a).Type: GrantFiled: July 12, 1989Date of Patent: May 15, 1990Assignee: BASF AktiengesellschaftInventors: Robert Maerkl, Wolfgang Harder
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Patent number: 4925973Abstract: Diesters of hexene-1,6-dioic acid are efficiently and selectively prepared by reacting carbon monoxide and an alcohol with at least one diacyloxylated butene compound, in the presence of (a) a catalytically effective amount of a palladium-based catalyst and (b) a quaternary onium chloride or bromide of nitrogen or phosphorus.Type: GrantFiled: June 13, 1989Date of Patent: May 15, 1990Assignee: Rhone-Poulenc ChimieInventors: Helene Deweerdt, Jean Jenck, Philippe Kalck
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Patent number: 4922002Abstract: This invention relates to certain linear, low-molecular-weight polyester-based polyols having at least two hydroxyl groups, low viscosity, high solids content and having the structural formula: ##STR1## wherein R is a moiety derived from a saturated aliphatic polyhydric alcohol; n is 1 or 2, and at least about 50% by weight, of n is n=1; p is 0 to 4 inclusive and m is 2 to 10 inclusive; said polyol being substantially free of any unreacted polyhydric alcohol.Type: GrantFiled: May 22, 1989Date of Patent: May 1, 1990Assignee: King Industries, Inc.Inventors: Leonard J. Calbo, Jr., Lawrence V. Gallacher
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Patent number: 4908400Abstract: A plasticizer for chloroprene rubber represented by the following general formula (I):R.sub.1 (O--R).sub.m S(R--O).sub.n R.sub.2 (I)wherein R.sub.1 and R.sub.2 independently represent each a saturated or unsaturated aliphatic monoacyl group having 4 to 24 carbon atoms;R represents an alkylene group having two to four carbon atoms; andm and n represent each an integer of 1 to 4:is disclosed.Type: GrantFiled: May 23, 1988Date of Patent: March 13, 1990Assignees: Du Pont-Showa Denko Co., Ltd., Adeka Argus Chemical Co., Ltd.Inventors: Yasushi Hirose, Kenji Iijima, Humihiro Kashima, Naoyasu Kurita, Koji Tajima, Hiroshi Hondou
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Patent number: 4904814Abstract: Process for the preparation of tert-alkyl esters of the formula I ##STR1## in which m is 1 or 2, R is C.sub.4 -C.sub.12 tert-alkyl and X, if m=1, is unsubstituted or halogen-substituted alkyl, cycloalkyl, unsubstituted or substituted aryl or aralkyl, or an aromatic heterocyclic radical and, if m=2, is a direct bond, --CH.sub.2).sub.n, in which n can be an integer from 1 to 8, or 1,2-, 1,3- or 1,4-phenylene, by reaction of an ester of the formula II ##STR2## in which R.sub.1 is methyl or ethyl, with an alcohol ROH in the presence of a catalyst customary for transesterifications.Type: GrantFiled: February 8, 1988Date of Patent: February 27, 1990Assignee: Ciba-Geigy CorporationInventors: Urs Frei, Rudolf Kirchmayr