Preparing From Compound Containing -coo- Group Patents (Class 549/326)
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Patent number: 4853473Abstract: 2(5H)-furanones I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.7 -C.sub.12 -aralkyl or aryl, are prepared by heating a 3-formylcarboxylate or 3-formylcarboxylic acid II ##STR2## where R.sup.3 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.7 -C.sub.12 -aralkyl or aryl, to 100.degree.-450.degree. C. in the presence of an acidic catalyst.Type: GrantFiled: June 1, 1988Date of Patent: August 1, 1989Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Juergen Frank, Franz Merger, Michael Roeper, Uwe Vagt
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Patent number: 4831166Abstract: .gamma.-butyrolactones of the general formula I ##STR1## where R.sup.1 is hydrogen or alkyl of 1 to 4 carbon atoms which may be substituted by lower alkoxy or acyloxy and R.sup.2 is hydrogen or straight-chain or branched alkyl which is unsubstituted or substituted by a functional group or is aryl, are prepared by reacting an alkylene oxide of the general formula II ##STR2## with an acylacetate of the general formla III ##STR3## where R.sup.1 and R.sup.2 have the above meanings and R.sup.3 and R.sup.4 are each alkyl of 1 to 6 carbon atoms or aryl, and R.sup.4 may furthermore be hydrogen, in the presence of a catalyst at elevated temperatures, by a process in which the reaction is carried out in the presence of an alkali metal halide, of an ammonium halide, preferably a quaternary ammonium halide, of a phosphonium halide, of an alkali metal phosphate or of an alkali metal carbonate at from 20.degree. to 200.degree. C. and under from 1 to 50 bar.Type: GrantFiled: May 8, 1987Date of Patent: May 16, 1989Assignee: BASF AktiengesellschaftInventors: Heinz Eckhardt, Walter Gramlich, Walter Best, Klaus Halbritter
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Patent number: 4827001Abstract: Disclosed is the hydrogenation of maleic acid in the presence of a solid iron-containing ruthenium catalyst containing the elements and the ratios indicated by the empirical formula,RuFe.sub.a M.sub.b O.sub.xwhereM is one or more of Pd and Rh,a is 0.1-5,b is zero-3, andx is a number sufficient to satisfy the valency requirements of the cations present in the catalyst,said process being effected by contacting in a reaction zone an excess of hydrogen with an aqueous solution of maleic acid in admixture with said catalyst.Type: GrantFiled: November 2, 1987Date of Patent: May 2, 1989Assignee: The Standard Oil CompanyInventors: Thomas G. Attig, Anne M. Graham
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Patent number: 4782167Abstract: A process is disclosed for preparing butyrolactones, butanediols, and mixtures thereof comprising hydrogenating a hydrogenatable precursor in the presence of an aqueous reaction medium and a catalyst comprising palladium or combinations thereof with rhenium and at least one support selected from the oxides of titanium, zirconium, and hafnium.Type: GrantFiled: January 23, 1987Date of Patent: November 1, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Velliyur N. M. Rao
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Patent number: 4772729Abstract: A process is disclosed for preparing 3-substituted tetrahydrofuran, 3- and 4-substituted butyrolactones and mixtures thereof comprising hydrogenating a hydrogenatable precursor in the presence of an aqueous reaction medium and a catalyst comprising palladium and rhenium and at least one support selected from the group consisting of titanium oxide, zirconium oxide, and carbon.Type: GrantFiled: January 23, 1987Date of Patent: September 20, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Velliyur N. M. Rao
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Patent number: 4751334Abstract: Butane-1,4-diol is produced by vapor phase hydrogenolysis of an alkyl ester of a C.sub.4 dicarboxylic acid, e.g. diethyl maleate, over a reduced Cu-Cr or Cu-Zn mixed oxide catalyst. Two adiabatic hydrogenolysis zones are used. The mixture exiting the first of these zones is cooled (by, for example, 5.degree. C.) and the resulting cooled mixture is fed to the second zone in which is reequilibriates at a lower temperature to increase the butane-1,4-diol yield at the expense of gamma-butyrolactone. Typical reaction conditions include use of temperatures of 150.degree. C. to 200.degree. C., pressures of 25 to 70 bar, and a H.sub.2 :ester molar ratio of 100:1 to 800:1. When using a maleate ester it is often advantageous to hydrogenate this to the corresponding succinate ester in an upstream hydrogenation zone prior to entry to the first hyrogenolysis zone.Type: GrantFiled: July 21, 1986Date of Patent: June 14, 1988Assignee: Davy McKee (London) LimitedInventors: Keith Turner, Mohammad Sharif, Colin Rathmell, John W. Kippax, Anthony B. Carter, John Scarlett, Arthur J. Reason, Norman Harris
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Patent number: 4740272Abstract: A method of producing substantially pure dialkyl maleate by separating monoalkyl maleate from dialkyl maleate in a short residence time distillation zone while minimizing reversion of the monoalkyl maleate to alkanol and maleic anhydride and without having to neutralize the monoalkyl maleate.Type: GrantFiled: March 31, 1987Date of Patent: April 26, 1988Assignee: Davy McKee (London) LimitedInventors: Ernesto Vera-Castaneda, Diane A. Montevideo, David J. Miller, John E. Logsdon, David R. Bryant
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Patent number: 4673759Abstract: A process for the preparation of 2-alkyl cyclopent-2-enones having the formula: ##STR1## wherein R is as defined hereinafter. An .alpha.-olefin having the formula CH.sub.2 .dbd.CH--CH.sub.2 R is oxidized to the corresponding epoxide. The epoxide is reacted with an alkylating agent having the formula Na.sup.+ [CH(COOR").sub.2 ].sup.-, wherein R" is an ethyl, an isopropyl, or an isobutyl radical. An .alpha.-carbalkoxy-.gamma.-alkyl lactone is obtained, which, through saponification and decarboxylation, yields a .gamma.-alkyl lactone having the formula: ##STR2## which is reacted with a protic acid, thereby obtaining, by cyclization, the desired 2-alkylcyclopent-2-enone. The obtained products are intermediates for the production of pharmaceutical products and of drugs for veterinary use, in particular prostaglandin.Type: GrantFiled: March 3, 1986Date of Patent: June 16, 1987Assignee: Montedison S.p.A.Inventor: Enrico Dalcanale
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Patent number: 4611069Abstract: A process for preparing gamma-caprolactone comprising isomerizing epsilon-caprolactone in an aqueous medium in the presence of catalytically effective amounts of hydriodic acid or hydrobromic acid wherein the catalyst is optionally promoted with a Group VIII metal. The temperature for the reaction is in the range of about 175.degree. C. to about 250.degree. C. and the ratio of water to epsilon-caprolactone is at least about 1:1.Type: GrantFiled: June 25, 1984Date of Patent: September 9, 1986Assignee: National Distillers and Chemical CorporationInventors: Jawad H. Murib, John H. Kahn
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Patent number: 4584419Abstract: A process for the production of butane-1,4-diol comprises hydrogenating a di(C.sub.1 to C.sub.3 alkyl) ester of a C.sub.4 dicarboxylic acid, e.g. an ester of a but-2-en-1,4-dioic acid, such as diethyl maleate, in the vapor phase at a temperature of from about 150.degree. C. to about 240.degree. C. and at a pressure in the range of from about 25 bar to about 75 bar in the presence of a reduced copper chromite catalyst, and recovering resulting butane-1,4-diol containing reaction product. The catalyst contains, before reduction, from about 25 to about 45% by weight of copper and from about 20 to about 35% by weight of chromium and preferably has an internal surface area of at least about 30 sq. m. per gram. The process is preferably conducted in two or more reaction zones, which are preferably operated adiabatically, the feed temperature to the first zone being higher than that to at least one subsequent reaction zone.Type: GrantFiled: November 21, 1984Date of Patent: April 22, 1986Assignee: Davy McKee Ltd.Inventors: Mohammad Sharif, Keith Turner
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Patent number: 4564689Abstract: In processes for reacting acetic acid with butadiene in solvent to prepare acetoxyhexenoic acid and .gamma.-vinyl-.gamma.-butyrolactone, involving electrolytic regeneration of a metal ion oxidant such as trivalent manganese, the product separation is facilitated by using low melting electrolyte salts and separating product from salts maintained in a molten state.Type: GrantFiled: June 13, 1983Date of Patent: January 14, 1986Assignee: Monsanto CompanyInventors: James P. Coleman, Dudley E. McMackins
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Patent number: 4560775Abstract: Butadiene and acetic acid are reacted with a metal salt oxidant in molten salt medium to form .gamma.-vinyl-.gamma.-butyrolactone. The process includes electrolytic regeneration of the oxidant and provides a simple reaction system which permits product recovery and reactant recycle without extensive solvent handling. A high surface area reactor can be employed.Type: GrantFiled: June 13, 1983Date of Patent: December 24, 1985Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins, Charles R. Penquite, Steven R. Auvil
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Patent number: 4550181Abstract: A process for preparing gamma-caprolactone comprising heating polycaprolactone in the presence of catalytically effective amounts of an acid comprised of hydrogen halides in a water solution to a temperature in the range of about 175.degree. C. to about 275.degree. C. and the ratio of water to polycaprolactone is in the range of about 1:1 to about 10:1.Type: GrantFiled: June 25, 1984Date of Patent: October 29, 1985Assignee: National Distillers and Chemical CorporationInventors: Jawad H. Murib, John H. Kahn
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Patent number: 4526990Abstract: In the process of preparing acetoxyhexenoic acids from butadiene, acetic acid and acetic anhydride, selectivity is improved by converting the acetoxyhexenoic acids to .gamma.-vinyl-.gamma.-butyrolactone before isolation. Copper and platinum are useful catalysts in the conversion.Type: GrantFiled: June 13, 1983Date of Patent: July 2, 1985Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Thomas E. Rogers, Dudley E. McMackins
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2 Or 3-tetradecenyl and poly isobutenyl substituted n-alkyl and n polyamino alkylene pyrrolid-2-ones
Patent number: 4473700Abstract: Disclosed are isomeric polyisobutenyl butyrolactones and lactams thereof useful as dispersants in lubricant oils and having the formulas: ##STR1## wherein R is a hydrocarbyl group having from 12 to 300 carbon atoms; X is O or >N--R', where R' is an alkyl or alkylamino group having from 1 to 20 carbon atoms and from 0 to 10 nitrogen atoms. The butyrolactones are made by mild reduction of the corresponding cyclic anhydrides and the lactams are prepared by reacting the intermediate butyrolactones with at least a molar equivalent of a primary amine, optionally, in the presence of a base or an acid.Type: GrantFiled: July 6, 1982Date of Patent: September 25, 1984Assignee: Texaco Inc.Inventor: Gary T. Babic -
Patent number: 4460787Abstract: The acid conversion of certain precursors, e.g. .gamma.-vinyl-.gamma.-butyrolactone, to sorbic acid is improved by presence of copper or silver ions along with the acid.Type: GrantFiled: December 21, 1981Date of Patent: July 17, 1984Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher
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Patent number: 4420622Abstract: The preparation of 5-alkyl-butyrolactones is described using C.sub.8 hydrocarbon levulinate esters, with side-chain alkyl substituents of up to 4 carbon atoms as starting material, with the reaction being conducted with hydrogen at a temperature of from 150.degree. to 325.degree. C., in the gas phase, and in the presence of a hydrogenation catalyst composed of metals of Group VIII or Group Ib of the Periodic Table. The process provides extremely high conversion rates and lactone yields, the prolonged catalyst activity.Type: GrantFiled: May 21, 1982Date of Patent: December 13, 1983Assignee: Stamicarbon B.V.Inventors: Cornelis G. M. van de Moesdijk, Petrus H. J. Janssen
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Patent number: 4380650Abstract: Acyloxyhexenoic acids are converted to .gamma.-vinyl-.gamma.-butyrolactone.Type: GrantFiled: January 2, 1981Date of Patent: April 19, 1983Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
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Patent number: 4356317Abstract: Acyloxyhexenoic acids are produced by reaction of butadiene and acetic acid with metal salt oxidants in a process involving electrolytic regeneration of the metal oxidants during the reaction.Type: GrantFiled: January 2, 1981Date of Patent: October 26, 1982Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins