Acyclic Monohydric Alcohol Moiety Patents (Class 560/265)
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Patent number: 4416868Abstract: A cosmetic excipient comprises a compound or mixture thereof having the formula ##STR1## wherein R is alkyl having 7-20 carbon atoms, a mixture of said alkyl radicals, the hydrocarbon residue of lanolin when X is oxygen or the hydrocarbon residue of lanolic acid when X is ##STR2## one of Z.sub.1 and Z.sub.2 represents --CH.sub.2 --Y--R' and the other represents hydrogen; X represents oxygen or carbonyloxy of the formula ##STR3## linked to R through the free bond of the carbon atom of the carbonyloxy group; Y represents --CH.sub.2 --, oxygen and carbonyloxy of the formula ##STR4## linked to R' through the free bond of the carbon atom of the carbonyloxy group R' represents alkyl having 3-30 carbon atoms or a mixture of said alkyl radicals, or a portion of the --Y--R' groups can represent --OH; A is hydrogen or when Y is carbonyloxy a mixture of hydrogen and ##STR5## wherein R' has the meaning given above; and n is a decimal or whole number greater than 1 and lower than or equal to 10.Type: GrantFiled: August 8, 1975Date of Patent: November 22, 1983Assignee: Societe Anonyme dite: L'OrealInventors: Guy Vanlerberghe, Henri Sebag
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Patent number: 4414410Abstract: Alkyl esters, such as ethyl acetate, are prepared by contacting the corresponding next lower carbon number alkyl ester, such as methyl acetate, with carbon monoxide and hydrogen in the presence of an iodine or iodide-free catalyst composition comprising a ruthenium-containing compound, a cobalt containing compound and a quaternary phosphonium salt or base, and heating the mixture to an elevated temperature and pressure for sufficient time to produce the desired higher alkyl ester, and then recovering the same from the reaction mixture.Type: GrantFiled: January 13, 1982Date of Patent: November 8, 1983Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton
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Patent number: 4408067Abstract: In a process for preparing a carboxylic acid ester from a nitrile, water and an alcohol in the vapor phase, wherein the vapor is brought into contact with a catalyst, the improvement which comprises said catalyst being a titanium containing oxide catalyst which is obtained by hydrolyzing or neutralizing a water soluble titanium salt and subsequently calcining the resulting precipitate at a temperature in a range of about 300.degree. to 750.degree. C. and having the empirical formula Ti.sub.a Me.sub.b X.sub.c O.sub.d, wherein Me represents at least one element selected from the group consisting of Cu, Ag, Au, Mg, Zn, Sn, Pb, Zr, V, Bi, Cr, W, Mo, Mn, Fe, Co and Ni and X represents at least one element selected from the group consisting of Si and Sb and the subscripts a, b, c and d designate the atomic ratio and when a is 1, b is 0.01 to 12, c is 0 to 12 and b+c is 0.01 to 12 and d is the oxygen content of the catalyst formed by the combination of the above components.Type: GrantFiled: July 28, 1981Date of Patent: October 4, 1983Assignee: Nitto Chemical Industries, Ltd.Inventors: Tomio Nakamura, Shunichi Doi
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Patent number: 4398039Abstract: A process is provided for the vapor phase hydrogenation of carboxylic acids to yield their corresponding alcohols in the presence of steam and a catalyst comprising the mixed oxides of ruthenium, at least one of cobalt, nickel, and optionally one of cadmium, zinc, copper, iron, rhodium, palladium, osmium, iridium and platinum. A process is further provided for the preparation of carboxylic acid esters from carboxylic acids in the absence of steam utilizing the above-identified catalysts.Type: GrantFiled: May 18, 1981Date of Patent: August 9, 1983Assignee: The Standard Oil CompanyInventors: Frederick A. Pesa, Anne M. Graham, Wayne R. Kliewer
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Patent number: 4374263Abstract: The invention relates to an esterification process employing as a heterogeneous catalyst an inorganic oxide, e.g. silica, to which there is bonded by reaction with surface hydroxyl groups a sulphonic acid-functionalized silane.Type: GrantFiled: October 24, 1980Date of Patent: February 15, 1983Assignee: The British Petroleum Company LimitedInventors: Ronald D. Hancock, Robert Mackison
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Patent number: 4374265Abstract: Process for the preparation of ethylidene diacetate by hydrogenating acetic anhydride in the presence of a heterogeneous palladium catalyst and a silica-alumina material.Type: GrantFiled: July 31, 1981Date of Patent: February 15, 1983Assignee: Eastman Kodak CompanyInventor: Thomas H. Larkins, Jr.
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Patent number: 4355173Abstract: A commercially acceptable and advantageous process for the preparation of an alkyl carboxylate having the formula R.sup.1 COOCH.sub.2 R.sup.2 by reacting an alkyl carboxylate having the formula R.sup.1 COOR.sup.2, carbon monoxide and hydrogen is disclosed (R.sup.1 is hydrogen, alkyl group or aromatic group and R.sup.2 is alkyl group). The reaction is conducted by the concurrent use of manganese and ruthenium as catalyst in the presence of iodine or bromine as the promoter. The reaction proceeds smoothly under milder condition in high yield and high selectivity.Type: GrantFiled: June 2, 1981Date of Patent: October 19, 1982Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Nobuo Isogai, Takashi Okawa, Motoyuki Hosokawa, Natsuko Wakui, Toshiyasu Watanabe
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Patent number: 4353835Abstract: A process for hydrogenating unsaturated carboxylic acids and esters of unsaturated carboxylic acids such as fatty acids which comprises reacting the unsaturated composition with hydrogen in contact with a catalyst prepared from a layered complex nickel silicate which has been prepared in a multi-stage procedure comprising reduction in a hydrogen atmosphere, oxidation in an atmosphere containing molecular oxygen and then again reduction in a hydrogen atmosphere.Type: GrantFiled: April 2, 1981Date of Patent: October 12, 1982Assignee: Gulf Research & Development CompanyInventor: Harold E. Swift
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Patent number: 4337351Abstract: Process for the preparation of ethylidene diacetate by hydrogenating acetic anhydride in the presence of a ruthenium on alumina catalyst and methyl iodide.Type: GrantFiled: January 30, 1981Date of Patent: June 29, 1982Assignee: Eastman Kodak CompanyInventor: Thomas H. Larkins, Jr.
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Patent number: 4334093Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more nickel-containing catalysts in combination with a Group VB tertiary donor ligand and in the presence of an iodide or bromide promoter.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Texaco, Inc.Inventor: John F. Knifton
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Patent number: 4334094Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more palladium-containing catalysts in combination with a Group VB tertiary donor ligand and in the presence of an iodide or bromide promoter.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4334092Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more rhodium-containing catalysts and an iodide or bromide promoter.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4332738Abstract: The esterification of neo acids catalyzed by the presence of a macro-reticular structured sulfonic acid cation exchange resin proceeds under mild conditions with a wide variety of alcohols to give readily recoverable esters in high yields and high purity and an easily recoverable and reusable catalyst.Type: GrantFiled: November 24, 1980Date of Patent: June 1, 1982Assignee: Exxon Research & Engineering Co.Inventors: Francisco M. Benitez, Michael F. English
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Patent number: 4328362Abstract: Acetic anhydride is reacted with hydrogen to produce ethylidene diacetate by carrying out the reaction in the presence of a catalyst comprising a molybdenum-nickel or a tungsten-nickel co-catalyst component and in the presence of an iodide and a promoter comprising an organo-phosphorus compound or an organo-nitrogen compound wherein the phosphorus and the nitrogen are trivalent.Type: GrantFiled: December 24, 1980Date of Patent: May 4, 1982Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla
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Patent number: 4327235Abstract: In an organic compound having a methlene group attached to a tertiary carbon atom thereof, preferential hydrogenation of the methylene group of the compound is effected by bringing hydrogen into contact with the compound in the presence of a nickel boride colloid.Type: GrantFiled: December 16, 1980Date of Patent: April 27, 1982Assignees: Agency of Industrial Science & Technology, Ministry of Inernational Trade & IndustryInventors: Yukimichi Nakao, Shoei Fujishige
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Patent number: 4326070Abstract: Beta deuterated 2-ethylhexanol and derivatives thereof, particularly esters of 2-d-2-ethylhexanol and mono- or dicarboxylic acids which are useful as lubricants, are provided. Improved resistance to oxidation is obtained with the deuterated ester products.Type: GrantFiled: February 17, 1981Date of Patent: April 20, 1982Assignee: Emery Industries, Inc.Inventors: Bruce J. Beimesch, Clarence E. Clark, Jr.
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Patent number: 4323513Abstract: This invention is concerned with improving ethylene glycol ester production from the reaction of carbon monoxide and hydrogen in a homogeneous liquid phase mixture containing a ruthenium carbonyl complex catalyst and acyl compound by maintaining the combined concentration of methyl ester, ethylene glycol ester and water in the reaction medium at less than about 30 volume percent. In a preferred embodiment, a continuous process is operated in such a manner that the methyl ester, ethylene glycol ester and water products are removed from the reactor so as to maintain their total volume concentration in the reaction medium at less than about 30 percent.Type: GrantFiled: November 4, 1980Date of Patent: April 6, 1982Assignee: Union Carbide CorporationInventor: Bernard D. Dombek
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Patent number: 4320230Abstract: A homogeneous catalytic process for the selective conversion of methanol to ethanol or acetaldehyde. The process comprises contacting CO and H.sub.2 with a catalytically effective amount of an iron-cobalt carbonyl complex of the formula M[FeCo.sub.3 (CO).sub.12 ] where M is hydrogen or a cation and an iodide promoter; heating the resulting mixture at temperatures of from 100.degree. to 250.degree. C. at pressures of from 5 to 100 MPa. By controlling the reaction parameters of H.sub.2 :CO ratio, temperature and reaction time, acetaldehyde or ethanol can be selectively produced.Type: GrantFiled: August 25, 1980Date of Patent: March 16, 1982Assignee: Exxon Research & Engineering Co.Inventor: Gerald Doyle
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Patent number: 4314947Abstract: A process for completing the esterification of aliphatic carboxylic acids of 1 to 8 carbon atoms with aliphatic or cycloaliphatic alcohols of 3 to 10 carbon atoms at the boiling point of the alcohol in a column operated with bottom heating, the lower space of the column being free from fitments, the middle space being provided with a packing and the upper space being provided with a packing or other fitments, in which process the water of esterification is driven off at the top of the column by azeotropic distillation, the starting mixture is fed into the side of the column from 5 to 10 m above the liquid level, the ester formed is taken off as liquid from the column bottom, and the column is operated with flooding such that the liquid level is from 6 to 10 m, with the liquid mixture filling the lower column space, which is free from fitments, and the lower part of the packed layer above the said space.Type: GrantFiled: December 21, 1978Date of Patent: February 9, 1982Assignee: BASF AktiengesellschaftInventors: Heinz Hohenschutz, Josef Gnad, Guenter Dinkhauser, Eberhard Schaefer
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Patent number: 4301084Abstract: In a process for the preparation of a carboxylic acid ester of .beta.-formyl-crotyl alcohol by rearrangement of the corresponding carboxylic acid ester of 2-formyl-2-hydroxy-but-3-ene or of an acetal or acylate thereof in the presence of copper or a copper compound, followed, where relevant, by hydrolytic cleavage of the acetal or acylate, more especially in the preparation of 4,4-dimethoxy-3-methyl-crotyl acetate, the yield is improved by carrying out the rearrangement in the presence of copper (I) chloride as the catalyst and ensuring that low-boiling by-products formed during the rearrangement are removed.The products are of great importance as starting materials for an industrial synthesis of vitamin A and its derivatives.Type: GrantFiled: August 31, 1979Date of Patent: November 17, 1981Assignee: BASF AktiengesellschaftInventors: Harald Laas, Axel Nissen, Bernd Meissner
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Patent number: 4276225Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.Type: GrantFiled: August 8, 1977Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hellmut Hoffmann
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Patent number: 4270015Abstract: This invention concerns a two-step process for the preparation of ethylene from mixture of carbon monoxide and hydrogen (commonly known as synthesis gas) by reaction of said carbon monoxide/hydrogen mixtures with a carboxylic acid in the presence of one or more ruthenium catalyst complexes to form an ethyl ester of said carboxylic acid coreactant, followed by pyrolysis of said ethyl ester intermediate to ethylene.Type: GrantFiled: July 14, 1980Date of Patent: May 26, 1981Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4268689Abstract: This invention concerns the improved preparation of glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a ruthenium or osmium-containing catalyst and a liquid phase medium containing a carboxylic acid co-reactant. The improvement which comprises the invention here also involves use of a co-catalyst species selected from the group consisting of one or more alkali metal salts, alkaline earth metal salts, quaternary ammonium salts, iminium salts and quaternary aliphatic phosphonium salts.Type: GrantFiled: December 14, 1979Date of Patent: May 19, 1981Assignee: Texaco Development Corp.Inventor: John F. Knifton
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Patent number: 4260820Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more ruthenium catalyst components and an iodide or bromide promoter.Type: GrantFiled: September 24, 1979Date of Patent: April 7, 1981Assignee: Texaco Development Corp.Inventor: John F. Knifton
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Patent number: 4250328Abstract: An improved method for separating an ester formed in a reaction mixture is disclosed. The method comprises controlling the ratio of organic acid and alcohol utilized and the removal of unreacted alcohol as an alcohol-ester azeotrope.Type: GrantFiled: February 6, 1979Date of Patent: February 10, 1981Assignee: Kyowa Yuka Co., Ltd.Inventors: Kiyoshi Fujita, Yukiyoshi Ito, Shigeru Kamimori
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Patent number: 4249015Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.Type: GrantFiled: January 26, 1979Date of Patent: February 3, 1981Assignee: Shell Oil CompanyInventors: John A. Schofield, John E. Hawes
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Patent number: 4239924Abstract: A process for selectively producing ethanol which comprises introducing into a reaction zone (1) methanol, (2) hydrogen, (3) carbon monoxide, (4) a cobalt tricarbonyl complex, (5) an iodine compound and (6) a ruthenium compound and then subjecting the contents of said reaction zone to an elevated temperature and an elevated pressure for a time sufficient to convert methanol to ethanol.Type: GrantFiled: May 25, 1979Date of Patent: December 16, 1980Assignee: Gulf Research & Development CompanyInventors: Wayne R. Pretzer, Thaddeus P. Kobylinski, John E. Bozik
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Patent number: 4239925Abstract: A process for selectively producing ethanol which comprises introducing into a reaction zone methanol, hydrogen, carbon monoxide, a cobalt tricarbonyl complex and an iodine promoter and then subjecting the contents of said reaction zone to an elevated temperature and an elevated pressure for a time period sufficient to convert methanol to ethanol.Type: GrantFiled: May 25, 1979Date of Patent: December 16, 1980Assignee: Gulf Research & Development CompanyInventors: Wayne R. Pretzer, Thaddeus P. Kobylinski, John E. Bozik
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Patent number: 4206310Abstract: An improved process for producing an ester from a carboxylic acid and an alcohol which comprises reacting said carboxylic acid with said alcohol by the use of a 1-substituted-2-halopyridinium salt or a 1-substituted-2-haloquinolinium salt as a condensing agent in the presence of a hydrogen halide captor. According to this process, various esters, even if they have some steric hindrances, may be obtained in good yields.Type: GrantFiled: September 8, 1978Date of Patent: June 3, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Masahiro Usui, Kazuhiko Saigo, Eiichiro Shimada
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Patent number: 4189441Abstract: A process is disclosed for preparing esters having the general formulae:RCOOCH.sub.2 R'andR'COOCH.sub.2 Rwherein R and R' are linear or branched alkyl radicals either like or unlike each other, and containing from 1 to 16 carbon atoms, or considered together, forming a cycloaliphatic ring having up to 7 carbon atoms, wherein carbon monoxide and hydrogen are reacted, at temperatures ranging from 150.degree. to 350.degree. C. and at pressures ranging from 50 to 1000 atmospheres, with an ether of formula R O R' or esters of formula RCOOR' and R'COOR, in which R and R' have the same meanings as specified hereinabove, and in the presence of a catalyst system comprising a ruthenium carbonyl and a promoter selected from the class consisting of hydroiodic acid, carboxylic acid solutions of inorganic or tetraalkylammonium bromides and iodides, and mixtures of these promoters.Type: GrantFiled: July 25, 1977Date of Patent: February 19, 1980Assignee: Montedison S.p.A.Inventors: Giuseppe Braca, Glauco Sbrana, Guglielmo Gregorio
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Patent number: 4177198Abstract: A process for preparing alkaline earth metal mercaptides, useful as synergists for organotin stabilizers in halogen containing resins such as polyvinyl chloride, the process comprising preparing an alkaline earth metal alkoxide by reacting the metal oxide or hydroxide with an alcohol and then reacting the alkoxide with a mercaptan to provide the corresponding alkaline earth metal mercaptide, preferably while removing water from the reaction mixtures throughout the process.Type: GrantFiled: January 3, 1978Date of Patent: December 4, 1979Assignee: Pennwalt CorporationInventor: Joseph M. Bohen
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Patent number: 4133966Abstract: A process for the selective formation of ethanol which comprises contacting methanol, hydrogen and carbon monoxide with a catalyst system comprising cobalt acetylacetonate, a tertiary organo Group V A compound of the periodic Table, a first promoter comprising an iodine compound and a second promoter comprising a ruthenium compound.Type: GrantFiled: December 23, 1977Date of Patent: January 9, 1979Assignee: Gulf Research & Development CompanyInventors: Wayne R. Pretzer, Thaddeus P. Kobylinski, John E. Bozik
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Patent number: 4131642Abstract: Isobutylene, hydrogen cyanide and sulfuric acid are reacted to produce tertiary butyl formamide, which is hydrolyzed by sodium hydroxide to produce tertiary butyl amine. The tertiary butyl amine is removed by vaporization and the residue is treated with sulphuric acid and methanol and is distilled to recover formate values as methyl formate or sodium formate. There is additionally recovered crystalline sodium sulfate and a water immiscible yellow organic phase.Type: GrantFiled: August 12, 1977Date of Patent: December 26, 1978Assignee: Ciba-Geigy CorporationInventors: Ralph Miller, Harry D. Gregg, Jr.
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Patent number: 4126627Abstract: A process for preparing alkaline earth metal mercaptides in a two-step process, useful as synergists for organotin stabilizers in halogen containing resins such as polyvinyl chloride, comprising: (1) reacting a metallic oxide or hydroxide of the metal desired in the final mercaptide; a magnesium, aluminum or calcium alkoxide; and an alcohol to provide an alkoxide of the metal of the final mercaptide; and then (2) reacting the final alkoxide of (1) with a mercaptan to provide the desired metal mercaptide.Type: GrantFiled: February 6, 1978Date of Patent: November 21, 1978Assignee: Pennwalt CorporationInventor: Gerald H. Reifenberg
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Patent number: 4126585Abstract: 2-Methyl-2-alkyl-alkanoic acid esters of the formula ##STR1## wherein R.sub.1 is a saturated or unsaturated, straight- or branched-chain aliphatic hydrocarbon radical having 1 to 5 carbon atoms, and R.sub.2 and R.sub.3 are independently an alkyl radical having 1 to 4 carbon atoms, which compounds have a wide variety of pleasing and persistent fragrances, and perfume compositions containing them.Type: GrantFiled: June 2, 1977Date of Patent: November 21, 1978Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Jens Conrad, Ulf-Armin Schaper, Klaus Bruns
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Patent number: 4100189Abstract: Acetic acid is recovered from its dilute aqueous solutions by extracting same with an organic solvent, neutralizing the acidic extract with aqueous ammonia, whereby there are separated an organic phase and an ammonium acetate containing aqueous phase, and thence thermally decomposing said ammonium acetate.Type: GrantFiled: January 21, 1976Date of Patent: July 11, 1978Assignee: Rhone-Poulenc IndustriesInventor: Jules Mercier
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Patent number: 4082788Abstract: Organic acids contained in aqueous solution are separated and/or recovered by a process comprising adding an alcohol to the aqueous solution to esterify the acids present, while preferably simultaneously contacting the alcoholic mixture with a water-immiscible solvent and separating layers into an aqueous phase and an organic phase, whereby extraction with the water-immiscible solvent shifts the equilibrium toward the formation of more esters. The esters of the acids may than be recovered as by distillation.Type: GrantFiled: August 19, 1969Date of Patent: April 4, 1978Assignee: El Paso Products CompanyInventor: Samuel S. Mims
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Patent number: 4068082Abstract: Esters are prepared by reaction of acyl halides and alcohols or hydroxyalkyl esters and acid halides in the presence of a tertiary amine and polar aprotonic solvents. Bis(2-methacrylatoethyl) phthalate is prepared by the reaction of phthaloyl chloride with 2-hydroxyethyl methacrylate in pyridine and acetone. Bis-phenol-A-bis(2-methacrylatoethyl)ether is prepared from 2,2-bis[4-(2-hydroxyethoxy)phenyl]-propane and methacryl chloride in acetone.Type: GrantFiled: September 19, 1973Date of Patent: January 10, 1978Assignee: Lee PharmaceuticalsInventors: Donald G. Stoffey, Jan Alexander Orlowski
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Patent number: 4055590Abstract: In a method for making a carboxylic acid ester by the reaction of the corresponding carboxylic acid amide with a primary alcohol in the presence of a catalyst at elevated temperature, the improvement wherein said catalyst is an at least partially dissolved metal carboxylate or a compound forming a metal carboxylate by reaction in situ with a carboxylic acid, the anion of which metal carboxylate is the anion of said carboxylic acid.Type: GrantFiled: June 22, 1976Date of Patent: October 25, 1977Assignee: Rohm GmbHInventors: Wilhelm Gruber, Guenter Schroeder