Preparing Esters From Ethers Patents (Class 560/240)
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Patent number: 4691048Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.Type: GrantFiled: May 10, 1985Date of Patent: September 1, 1987Assignee: Institut Francais du PetroleInventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
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Patent number: 4677181Abstract: The present invention is directed to polyhydroxyl compounds containing both ether and ester groups, having an average hydroxyl functionality of 2 to 6 and an average hydroxyl number of about 100 to 600, based on the esterification product of (i) polyether polyols having an average hydroxyl functionality of 3 to 8 and an average hydroxyl number of about 200 to 1000 with (ii) about 5 to 70 equivalent %, based on the hydroxyl group of component (i) and the carboxyl group of component (ii), of organic monocarboxylic acids. The present invention is also directed to the use of the polyhydroxyl compounds as synthesis components in the production of polyurethane plastics materials by the isocyanate-polyaddition process, particularly their use as the polyol component in two-component polyurethane coating agents and/or polyurethane casting systems which are solvent-free or have a low solvent content.Type: GrantFiled: July 21, 1986Date of Patent: June 30, 1987Assignee: Bayer AktiengesellschaftInventors: Peter Hohlein, Alois Fehlbier, Hermann Gruber
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Patent number: 4665236Abstract: Alkylene oxide adducts of organic compounds having an active hydrogen are prepared by a process in which an active hydrogen reactant and an alkylene oxide reactant are reacted in the presence of a catalytically effective amount of one or more bimetallic oxo compounds of the formula (RO).sub.n M--O--M'--O--M(OR).sub.n, wherein each R is (independently) an optionally-substituted organic moiety, M' is a divalent metal selected from the elements of Groups VIII, Ib, IIb, IIIb, and IVb of the Periodic Table, each M is (independently) a trivalent or tetravalent metal, and each n is 2 if the adjacent M is trivalent of 3 if the adjacent M is tetravalent. The products are useful, for instance, as nonionic surfactants in detergent formulations. In certain preferred embodiments, the process yields a product having a very desirable distribution of alkylene oxide adducts.Type: GrantFiled: April 3, 1986Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 4665094Abstract: Hydroxyalkyl-phenoxy-propan-2-olamines and novel esters thereof are oculoselective .beta.-blockers useful in the treatment of elevated intraocular pressure with little or no effect on the pulmonary or cardiovascular system.Type: GrantFiled: August 29, 1985Date of Patent: May 12, 1987Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Gerald S. Ponticello
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Patent number: 4659865Abstract: A process for producing ethylidenediacetate which comprises reacting methyl acetate or dimethyl ether, carbon monoxide and hydrogen in the presence of catalyst comprising as a secondary-component at least one material selected from the group consisting of, iodides and bromides and as a main component combination of (1) at least one material selected from the group consisting of nickel and nickel compounds, at least one material selected from the group consisting of cobalt and cobalt compounds under substantially anhydrous conditions is disclosed. According to the present invention synthesis of ethylidenediacetate is achieved by using a cheaper catalyst than the prior catalyst.Type: GrantFiled: July 30, 1984Date of Patent: April 21, 1987Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi, Takayuki Yasunaga
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Patent number: 4654174Abstract: The invention disclosed herein is a process for preparing aliphatic anhydrides comprising contacting a divinyl ether with carboxylic acid in the presence of a catalytic amount of a strong acid. The invention is further a process for preparing alkylidene dicarboxylates, which are intermediates in the above preparation of aliphatic anhydride.Type: GrantFiled: May 28, 1982Date of Patent: March 31, 1987Assignee: The Dow Chemical CompanyInventors: James A. Kaufman, Suzanne V. McKinley
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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: 4603219Abstract: The compounds 9-(1,3-dihydroxy-2-propoxymethyl)guanine and the pharmaceutically acceptable salts thereof are useful as antiviral agents. The compound 1,3-dibenzyloxy-2-acetyloxy-methoxypropane is useful as an intermediate for the preparation of 9-(1,3-dihydroxy-2-propoxymethyl)guanine.Type: GrantFiled: October 29, 1984Date of Patent: July 29, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Julien P. H. Verheyden, John C. Martin
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Patent number: 4590294Abstract: The invention relates to the use of hydrogen ion-exchanged layered clays in organic reactions which are catalyzed by protons. Such organic reactions include the production of ethers by the reaction of an alcohol with an olefin or an olefin oxide, the production of an ether by the reaction of a primary or secondary aliphatic alcohol or an olefin oxide, the production of an alkyl aromatic compound by the reaction of an aromatic hydrocarbon with an olefin or a C.sub.2 or higher alcohol and the production of an alcohol by the hydration of an olefin.Type: GrantFiled: August 12, 1985Date of Patent: May 20, 1986Assignee: The British Petroleum Company LimitedInventors: James A. Ballantine, Reginald Gregory, John H. Purnell, John M. Thomas, David J. Westlake
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Patent number: 4585592Abstract: In polyoxybutylene polyoxyalkylene glycols obtained by copolymerization of tetrahydrofuran with a 1,2-alkylene oxide in the presence of a compound containing reactive hydrogen and under the catalytic action of a bleaching earth, the content of oligomeric cyclic ethers is reduced by distillation under reduced pressure at above 200.degree. C. after first treating the copolymer with oxygen or an oxygen-containing gas (air) at a temperature of from 20.degree. to 110.degree. C.Type: GrantFiled: February 28, 1985Date of Patent: April 29, 1986Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4568774Abstract: Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF.sub.3 and metal alkyls or metal alkoxides, SiF.sub.4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.Type: GrantFiled: October 1, 1984Date of Patent: February 4, 1986Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4564671Abstract: Polyoxybutylene polyoxyalkylene glycols are prepared by copolymerization of tetrahydrofuran with a 1,2-alkylene oxide in the presence of a compound containing reactive hydrogen, by a continuous process in which the polymerization is carried out in a reactor over a fixed-bed clay catalyst and with recycling of the reaction mixture, and less than 30% by weight, based on the reaction mixture to be recycled, of a mixture of tetrahydrofuran, 1,2-alkylene oxide and a compound containing reactive hydrogen is added to the reaction mixture, which is recycled to the reactor after flowing through the latter.Type: GrantFiled: December 14, 1984Date of Patent: January 14, 1986Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4559177Abstract: A compound of the formula: ##STR1## wherein m is an integer of 11 to 22; R.sub.1 is alkyl having 1 to 4 carbon atoms; R.sub.2 is hydrogen, alkyl having 1 to 4 carbon atoms or carboxylic acyl having 1 to 8 carbon atoms. Such compounds have pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory and lysosomal membrane stabilizing activity, and inhibit SRS-A production, and are useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.Type: GrantFiled: June 30, 1980Date of Patent: December 17, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Tetsuya Okutani, Giichi Goto
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Patent number: 4544453Abstract: An improved method of stripping unreacted alkylene glycol monoalkyl ethers and unreacted monocarboxylic or halogenated monocarboxylic acids from a mixture containing the monocarboxylic acid ester prepared therefrom by acid catalyzed esterification without any significant loss of the product ester. The method involves the injection of water into the distillate during the stripping and is particularly suitable for the recovery of propylene glycol monomethyl ether and acetic acid from esterification reaction mixtures containing a predominate amount of product propylene glycol monomethyl ether acetate. The process allows for removal and recovery or recycle of the ether and acid and the preparation of a higher purity product ester.Type: GrantFiled: May 31, 1984Date of Patent: October 1, 1985Assignee: Atlantic Richfield CompanyInventor: Vijai P. Gupta
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Patent number: 4518797Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: May 21, 1985Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4499298Abstract: A process is described for the preparation of aryl esters such as benzyl acetate by reacting an aryl alkyl compound such as toluene with a carboxylic acid such as acetic acid and oxygen in the presence of a catalytically effective amount of a catalyst comprising palladium metal, gold metal and a metal of Group VA of the Periodic Table of the Elements such as bismuth.Type: GrantFiled: December 20, 1979Date of Patent: February 12, 1985Assignee: National Distillers and Chemical CorporationInventors: John A. Scheben, James A. Hinnenkamp
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Patent number: 4480124Abstract: The subject invention relates to a process for purifying polytetramethylene ether glycol or the corresponding diester prepared by cationic polymerization of tetrahydrofuran comprising treating said glycol or diester with hydrogen in the presence of a hydrogen catalyst. The resulting products have a low color number.Type: GrantFiled: March 11, 1982Date of Patent: October 30, 1984Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4472294Abstract: A fluorine-containing compound of the formula: ##STR1## wherein Rf is a C.sub.3 -C.sub.21 fluorine-containing group; R is a hydrogen atom or a C.sub.1 -C.sub.4 acyl group; Q is an aliphatic or aromatic hydrocarbon group having not more than twenty-one carbon atoms; and n is an integer of 1 to 10 lowers the surface tensions of water and/or organic liquids and the interfacial tensions between them.Type: GrantFiled: January 29, 1982Date of Patent: September 18, 1984Assignee: Daikin Kogyo Co., Ltd.Inventors: Iwao Hisamoto, Chiaki Maeda, Mitsuhiro Nishiwaki
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Patent number: 4466922Abstract: 3-Alkyl-3-acyloxy-4-hydroxybut-1-enes are prepared by a process in which a 3-alkyl-3,4-epoxybut-1-ene is treated with a carboxylic acid and a copper salt of a carboxylic acid.Type: GrantFiled: September 13, 1982Date of Patent: August 21, 1984Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Fischer
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Patent number: 4310465Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.Type: GrantFiled: December 17, 1979Date of Patent: January 12, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Gabriel Saucy
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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: 4298758Abstract: Propylene glycol and dipropylene glycol diesters are prepared by reacting dichloropropyl ethers with a carboxylic acid salt, e.g., sodium acetate, and the corresponding carboxlyic acid, e.g., acetic acid. The by-product sodium chloride is insoluble in the acetic acid and easily separated from the reaction mixture. The diesters can be hydrolyzed to their respective glycols.Type: GrantFiled: February 11, 1980Date of Patent: November 3, 1981Assignee: The Dow Chemical CompanyInventors: Frank T. Cook, Donald G. Prier
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Patent number: 4296042Abstract: This process relates to the synthesis of unsaturated aliphatic esters useful as insect sex attractants, including gossyplure, the insect sex pheromone of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor. The process utilizes a cyclic phosphonium (Wittig) reagent.Type: GrantFiled: June 18, 1980Date of Patent: October 20, 1981Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Michael C. Venuti
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Patent number: 4288614Abstract: A novel process for the preparation of esters of 5-formyl-3-methyl-2,4-pentadien-1-ol which employs as starting materials 2-substituted-3-methyl-6-alkoxy-3,6-dihydro-2H-pyrans. Novel intermediates are also disclosed.Type: GrantFiled: February 6, 1980Date of Patent: September 8, 1981Assignee: Hoffmann-La Roche Inc.Inventor: Gary L. Olson
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Patent number: 4273934Abstract: 3-Hydroxy-2,2,4-trimethylpentyl isobutyrate is prepared by reaction of isobutyraldehyde in the presence of an alkaline earth metal hydroxide and of carboxylic acids or the corresponding salts, under specific conditions in respect of reaction time and proportion and concentration of the hydroxide suspension. The product is a starting material for the preparation of dyes, pesticides, adhesives and surface coatings.Type: GrantFiled: April 17, 1979Date of Patent: June 16, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Hans-Juergen Foerster
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Patent number: 4267363Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the yellow scale.Type: GrantFiled: June 26, 1978Date of Patent: May 12, 1981Assignee: Zoecon CorporationInventors: Richard J. Anderson, Clive A. Henrick
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Patent number: 4263443Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.Type: GrantFiled: November 22, 1978Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: John F. White
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Patent number: 4259531Abstract: Polytetramethylene ether glycols with molecular weights of from 300 to 4500 are produced by polymerizing tetrahydrofuran with an adduct of antimony pentachloride with carboxylic acids or carboxylic acid esters as the catalyst in the presence of a carboxylic acid anhydride, e.g., acetic anhydride, as the promoter. Esterified, e.g., acetylated, polytetramethylene ether glycols produced are subsequently converted to polytetramethylene ether glycols by saponification or transesterification. The process causes substantially less environmental pollution than do prior art methods, yet it is both economical and flexible.Type: GrantFiled: December 15, 1978Date of Patent: March 31, 1981Assignee: BASF AktiengesellschaftInventors: Otto H. Huchler, Walter Mesch, Siegfried Winderl, Herbert Mueller, Herwig Hoffmann
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Patent number: 4258207Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4258205Abstract: New 2,2-dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives of the formula ##STR1## wherein X is --CH.sub.2 OC(O)CH.sub.3, --CH.sub.2 OH, or --CHO are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.Type: GrantFiled: December 4, 1978Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventors: Johannes Van Berkel, Hendrik C. Kelderman
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Patent number: 4252738Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.Type: GrantFiled: March 17, 1978Date of Patent: February 24, 1981Assignee: Bayer AktiengesellschaftInventors: Willy Hartmann, Hans-Georg Heine
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Patent number: 4252935Abstract: Esters of glycidyl polyethers of saturated phenols are especially useful in coating compositions having a low organic solvent content. The esters are the reaction products of from about 0.5 to about 1.5 equivalents of a saturated monocarboxylic acid with each epoxy group in a diglycidyl polyether of phenols where the aromatic rings of the phenols are saturated.Type: GrantFiled: July 31, 1979Date of Patent: February 24, 1981Assignee: PPG Industries, Inc.Inventors: Carl C. Anderson, William J. Birkmeyer, Roger M. Christenson, Rostyslaw Dowbenko, Ronald J. Lewarchik
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Patent number: 4243799Abstract: A process for the preparation of polybutylene glycol carboxylic acid diesters of the formulaR--CO--O--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --O).sub.n CO--R.sup.1by polymerizing pretreated tetrahydrofuran in the presence of one or more carboxylic acids and/or carboxylic acid anhydrides and of a polymerization catalyst, especially antimony pentachloride or a bleaching earth containing less than 3% by weight of water, wherein the tetrahydrofuran is treated with a strong mineral acid, an organic sulfonic acid, silica gel and/or a bleaching earth prior to the polymerization.Type: GrantFiled: May 18, 1979Date of Patent: January 6, 1981Assignee: BASF AktiengesellschaftInventors: Herbert Mueller, Otto H. Huchler, Herwig Hoffmann
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Patent number: 4229592Abstract: The compound of the formula ##STR1## has been found to be an important and practical intermediate with the proper stereo-isomerism for the preparation of numerous prostaglandin derivatives. It can easily be converted to 4.alpha.-acetoxy-2-cyclopentenone by a variety of processes.Type: GrantFiled: February 6, 1978Date of Patent: October 21, 1980Assignee: Kansas University Endowment AssociationInventors: Lester A. Mitscher, George W. Clark, III, Paul B. Hudson
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Patent number: 4223160Abstract: Niobium and ruthenium salts are employed as catalyst in the reaction of oxirane compounds with carboxylic acids. The acrylate esters produced can be used in photocurable compositions.Type: GrantFiled: March 26, 1979Date of Patent: September 16, 1980Assignee: Union Carbide CorporationInventor: Lawrence G. Hess
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Patent number: 4214099Abstract: A new synthesis of key prostaglandin precursors and intermediates employed in their preparation. The novel synthetic sequence of this invention is shorter and more efficient than those previously employed to prepare to key intermediate.Type: GrantFiled: June 22, 1978Date of Patent: July 22, 1980Assignee: Pfizer Inc.Inventors: Elias J. Corey, Jasjit S. Bindra, Thomas K. Schaaf
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Patent number: 4175204Abstract: E-4-acetoxy-2-methyl-2-butenal is prepared by: (1) preparation of an intermediate allylic halide from isoprene; and (2) reaction of the allylic halide with dimethyl sulfoxide in the presence of a non-nucleophilic base to form the desired product.Type: GrantFiled: January 8, 1979Date of Patent: November 20, 1979Inventor: James H. Babler
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Patent number: 4171375Abstract: Cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a carboxylic acyl group, R.sup.2 represents hydrogen or alkyl of 1 through 12 carbon atoms, and n represents an integer from 4 through 8, are new compounds possessing pharmacological properties, more particularly the production of hypertension and inhibition of gastric acid secretion. They are also useful in the preparation of 10-hydroxyprostaglandins.Type: GrantFiled: January 12, 1977Date of Patent: October 16, 1979Assignee: May & Baker LimitedInventors: Michael P. L. Caton, Trevor Parker, Gordon L. Watkins
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Patent number: 4163115Abstract: Esters of poly(tetramethylene ether) glycol are prepared by polymerizing tetrahydrofuran in a reaction mixture which contains, in addition to the tetrahydrofuran, and acylium ion precursor such as acetic anhydride, a polymeric catalyst which contains sulfonic acid groups and, optionally, a carboxylic acid such as acetic acid.Type: GrantFiled: January 13, 1978Date of Patent: July 31, 1979Assignee: E. I. Du Pont de Nemours and CompanyInventors: George E. Heinsohn, Ivan M. Robinson, Gerfried Pruckmayr, Walter W. Gilbert
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Patent number: 4153805Abstract: A total synthesis of canthaxanthin or dinor-canthaxanthin, known food coloring agents, from pentols.Type: GrantFiled: September 29, 1977Date of Patent: May 8, 1979Assignee: Hoffmann-La Roche Inc.Inventor: Michael Rosenberger
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Patent number: 4131739Abstract: Cyclic acetals are rearranged to form isomeric carboxylic acid esters according to the following formula: ##STR1## wherein R is an alkyl, alkenyl, or aromatic moiety containing 1 to 12 carbon atoms;AndR' is an alkyl or alkenyl moiety containing 1 to 12 carbon atoms;In the presence of a catalyst consisting of a metal selected from the group Ru, Rh, Pd, Os, Ir or Pt supported on carbon.Type: GrantFiled: July 11, 1977Date of Patent: December 26, 1978Assignee: Eastman Kodak CompanyInventor: Don L. Morris
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Patent number: 4110539Abstract: This invention describes a process for the synthesis of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate by the acid catalyzed cleavage and esterification of 2,4-diisopropyl-5,5-dimethylmetadioxane.Type: GrantFiled: July 13, 1977Date of Patent: August 29, 1978Assignee: Eastman Kodak CompanyInventors: Kenneth H. Albers, Howard N. Wright, Jr.
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Patent number: 4092339Abstract: Homopolymers and copolymers of glycidyl esters are made by reacting the acids to be esterified with the corresponding polymer of tert.-alkyl glycidyl ether under substantially anhydrous conditions and in the presence of a strong acid catalyst, preferably a sulfonic acid. The reaction proceeds satisfactorily at about 100.degree.14 150.degree. C with displacement of the tert.-alkyl group by the acyl group of the acid and evolution of tert.-olefin. By use of the appropriate proportion of reactant acid and/or appropriate reaction time, any desired proportion of the glycidyl groups can be esterified.Type: GrantFiled: November 19, 1975Date of Patent: May 30, 1978Assignee: The Dow Chemical CompanyInventors: Violete L. Stevens, Arthur R. Sexton, Frederick P. Corson
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Patent number: 4087453Abstract: A process for recovering monomeric glycols and glycerine from polyoxyalkylene glycols and polyglycerines which comprises heating the polymeric compounds together with a lower saturated mono-carboxylic acid, containing from 2 to 4 carbon atoms such as acetic acid, in the presence of a strong acid, e.g. sulfuric acid, or a strong acid cation exchange resin. The product, which is the diester of the monomeric glycol or the triester of glycerine, is recovered and subsequently hydrolyzed to obtain the desired monoglycol or glycerine product. If it is desired to obtain the ester itself, the latter step of hydrolyzing can be omitted.Type: GrantFiled: June 18, 1976Date of Patent: May 2, 1978Assignee: The Dow Chemical CompanyInventors: Fred A. Sherrod, William L. Howard, Joanne D. Burger
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Patent number: 4069242Abstract: A synergistic catalytic effect is realized in the esterification reaction between an organic carboxylic acid and a vicinal epoxide by using a catalyst system comprising: (a) a compound containing an amino and/or ammonium nitrogen atom, in combination with (b) a soluble compound containing an ionizable atom of iron or chromium.Type: GrantFiled: September 9, 1971Date of Patent: January 17, 1978Assignee: The Dow Chemical CompanyInventor: Arthur E. Gurgiolo
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Patent number: 4069385Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.Type: GrantFiled: June 3, 1976Date of Patent: January 17, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Araki, Tsuneyuki Nagase
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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: 4052424Abstract: This invention provides a process for producing carboxylic esters in high yield by contacting alkanol in vapor phase with a novel silver-cadmium alloy catalyst.Type: GrantFiled: September 1, 1976Date of Patent: October 4, 1977Assignee: Celanese CorporationInventor: Thomas H. Vanderspurt