Preparing Esters By Carbonylation Patents (Class 560/206)
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Patent number: 4450285Abstract: .beta.,.gamma.-Unsaturated esters are prepared by the reaction of the corresponding .beta.,.gamma.-unsaturated carbonate with carbon monoxide in the presence of a group VIII metal catalyst.Type: GrantFiled: February 22, 1982Date of Patent: May 22, 1984Assignee: The Dow Chemical CompanyInventors: Edmund P. Woo, Daniel J. Murray
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Patent number: 4435575Abstract: A process is herein described for preparing carboxylated organic compounds (acids, esters, alkaline salts) of formula ##STR1## wherein R is a hydrocarbyl group having up to 11 carbon atoms (an aliphatic, alicyclic, aryl- or heteroarylalkyl group), also substituted, in its turn, by groups inert under the reaction conditions (alkyl, aryl, etheric, thioetheric, halogen, nitrile, ester, amide, ketonic groups), and R' is a hydrogen atom or an alkyl C.sub.1 -C.sub.8 group, by reaction of carbon monoxide with the corresponding hydrocarbyl halides, having the halogen bound to a non-tertiary carbon atom, in the presence of catalysts which are salts of cobalt hydrocarbonyl, or precursors thereof, in a hydro-alcoholic or alcoholic solvent and in the presence of bases.The process is characterized in that the catalytic system composed by the salt of cobalt hydrocarbonyl is supported on an anion exchange resin.Type: GrantFiled: June 30, 1981Date of Patent: March 6, 1984Assignee: Montedison S.p.A.Inventors: Gianfranco Cainelli, Marco Foa', Achille U. Ronchi, Andrea Gardano
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Patent number: 4404394Abstract: A process for producing adipic acid diester which comprises the first step of reacting butadiene, carbon monoxide and an alcohol in the present of cobalt carbonyl catalyst at a temperature of from 80.degree. to 160.degree. C. to form a 3-pentenoic acid ester, andthe second step of reacting the 3-pentenoic acid ester in the reaction mixture, carbon monoxide and an alcohol at a temperature of from 160.degree. to 220.degree. C., characterized in that the first and second reactions are carried out in an amine solvent is disclosed.Type: GrantFiled: November 6, 1981Date of Patent: September 13, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Nobuo Isogai, Motoyuki Hosokawa, Takashi Okawa, Natsuko Wakui, Toshiyasu Watanabe
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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: 4350668Abstract: In a process for producing a 3-pentenoic ester which comprises reacting butadiene, carbon monoxide and an alcohol in the presence of a solvent and a catalyst selected from cobalt carbonyl or cobalt carbonyl complex, the improvement which comprises distilling the reaction mixture to remove organic volatile components comprised of the 3-pentenoic ester and the unreacted raw materials and the solvent and contacting the distillation residue with an organic solvent to dissolve and/or disperse the residue in the solvent and contacting the resulting organic solution with an aqueous acid solution to extract any cobalt component from the organic solution with the aqueous acid solution, and separating the aqueous acid solution containing the cobalt component from the organic solution, and neutralizing the aqueous acid solution with an alkaline solution to precipitate a cobalt component is disclosed.Type: GrantFiled: March 20, 1981Date of Patent: September 21, 1982Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Nobuo Isogai, Takashi Okawa, Motoyuki Hosokawa, Toshiyasu Watanabe, Natsuko Wakui
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Patent number: 4332966Abstract: A process is disclosed for producing a 3-pentenoic ester which comprises reacting butadiene, carbon monoxide and an alcohol in the presence of cobalt carbonyl catalyst, characterized in that the reaction is carried out in a reaction medium composed of at least two solvents selected from the group consisting of pyridine, quinoline, isoquinoline and substituted pyridine, substituted quinoline and substituted isoquinoline in which substituent or substituents are selected from the group consisting of alkyl having 1-6 carbon atoms, alkenyl having 1-6 carbon atoms, aryl, alkylaryl having 7-10 carbon atoms and aralkyl having 7-10 carbon atoms.Type: GrantFiled: October 21, 1980Date of Patent: June 1, 1982Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Nobuo Isogai, Motoyuki Hosokawa, Takashi Okawa, Natuko Wakui, Toshiyasu Watanabe
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Patent number: 4316047Abstract: A process for the preparation of C.sub.1 -C.sub.4 -alkyl pent-3-enoates, wherein butadiene, or a hydrocarbon mixture containing butadiene, either of which contains not more than 0.1% by weight of butynes, is reacted with carbon monoxide and an alkanol of 1 to 4 carbon atoms in the presence of a cobalt carbonyl catalyst and a tertiary nitrogen base, having a pK.sub.A of 3-11, at from 100.degree. to 140.degree. C. under a pressure of from 300 to 1,000 bar.Type: GrantFiled: July 7, 1980Date of Patent: February 16, 1982Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Franz-Josef Weiss, Heinz-Walter Schneider, Volker Taglieber
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Patent number: 4259519Abstract: Conjugated diolefins (e.g., 1,3-butadiene) are carbonylated by the palladium-catalyzed addition of carbon monoxide and an alcohol of the formula ROH (e.g., benzyl alcohol) whereby polycarboxylic esters are formed in which the pair of double bonds of the conjugated diolefin has been transformed into a moiety having the formula: ##STR1## In the process, the olefin, carbon monoxide, and alcohol are reacted in the presence of a palladium(II) salt, a copper(II) salt, and a base, at certain concentrations and at a pressure and temperature sufficient to effect the carbonylation. The resulting unsaturated diester can be hydrolyzed and hydrogenated or vice versa to obtain the corresponding linear diacid (e.g., adipic acid).Type: GrantFiled: July 19, 1978Date of Patent: March 31, 1981Assignee: Polymer Sciences CorporationInventor: John K. Stille
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Patent number: 4257973Abstract: Water, primary alcohols or secondary alcohols together with carbon monoxide can be added across ethylenic or acetylenic bonds in a wide variety of organic compounds to form acids or esters. The reaction is conducted in the presence of a catalyst system consisting of an organophosphorus palladium halide compound and certain metal halide compounds.Type: GrantFiled: November 5, 1971Date of Patent: March 24, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joseph J. Mrowca
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Patent number: 4171451Abstract: A process for the manufacture of butanedicarboxylic acid esters, wherein(a) an aqueous cobalt salt solution is treated, at from 50.degree. to 200.degree. C. and under a pressure of from 50 to 500 bars, with excess carbon monoxide and hydrogen in the presence of active charcoal laden with cobalt carbonyl,(b) the resulting aqueous solution of cobalt carbonyl hydride is extracted with butadiene or with a hydrocarbon mixture containing butadiene and the aqueous phase is separated off,(c) the butadiene, or butadiene-hydrocarbon mixture, containing cobalt carbonyl hydride, cobalt carbonyl and butenyl-cobalt tricarbonyl is reacted with carbon monoxide and an excess of an alkanol of 1 to 4 carbon atoms in the presence of from 0.5 to 2 moles, per mole of butadiene, of a tertiary nitrogen base having a pK.sub.a of from 3 to 11, at from 80.degree. to 150.degree. C.Type: GrantFiled: March 3, 1978Date of Patent: October 16, 1979Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Heinz-Walter Schneider, Rolf Platz, Peter Magnussen, Franz-Josef Weiss
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Patent number: 4169956Abstract: A process for the manufacture of butanedicarboxylic acid esters, wherein(a) an aqueous cobalt salt solution is treated with carbon monoxide and hydrogen in the presence of active charcoal,(b) the resulting aqueous solution is extracted with butadiene or with a hydrocarbon mixture containing butadiene,(c) the butadiene, or butadiene/hydrocarbon mixture, containing cobalt carbonyl hydride, cobalt carbonyl and butenyl-cobalt tricarbonyl, is reacted with carbon monoxide and an excess of an alkanol of 1 to 4 carbon atoms in the presence of a tertiary nitrogen base,(d) the tertiary nitrogen bases contained in the resulting reaction mixture are removed from the latter to the extent of leaving from 0.1 to 0.Type: GrantFiled: September 8, 1978Date of Patent: October 2, 1979Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Heinz-Walter Schneider, Franz-Josef Weiss
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Patent number: 4156785Abstract: Process of preparing an .alpha.,.beta.-unsaturated carboxylic acid ester, comprising contacting an .alpha.,.beta.-unsaturated halogen compound with carbon monoxide, an alkali alcoholate in the presence of a metal carbonyl as catalyst, in an alcohol that is the basis of the alkali alcoholate, at a pH of 8.5-11.5. Thereby, for example, crotonic acid methyl ester can be produced from allyl chloride.Type: GrantFiled: July 28, 1975Date of Patent: May 29, 1979Assignee: Dynamit Nobel AktiengesellschaftInventors: Uwe Prange, Hermann Richtzenhain, Wilhelm Vogt
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Patent number: 4140865Abstract: Vinylacetic acid and optionally .gamma.-butyrolactone are prepared by reacting an allyl compound substituted by oxygen functions with carbon monoxide in the presence of a heavy metal catalyst. When the reaction is carried out with an allyl ether or a carboxylic acid allyl ester, water is added. Vinylacetic acid is obtained in a very good yield in simple and economic manner.Type: GrantFiled: March 12, 1976Date of Patent: February 20, 1979Assignee: Hoechst AktiengesellschaftInventors: Hans Fernholz, Dieter Freudenberger