Aldehyde Group In Acid Moiety Patents (Class 560/177)
-
Patent number: 5217582Abstract: A process is provided for separating high purity alkyl glycolate from a gaseous reaction mixture resulting from the catalyzed gas phase oxidation of alkyl glycolate. A hot solvent which is immiscible with water but selectively dissolves alkyl glycolate and alkyl glyoxylate is brought in contact with the gaseous reaction mixture, and water and alcohol vapors are removed from the hot solvent. The alkyl glyoxylate is removed from the solution by a first distillation and the alkyl glycolate and solvent are then separated in a second distillation.Type: GrantFiled: February 7, 1992Date of Patent: June 8, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: George E. Heinsohn, John F. Kook, John R. Kosak, Rudolf E. Svadlenak
-
Patent number: 5206389Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.Type: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: AtochemInventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
-
Patent number: 5206419Abstract: Process for the preparation of acetoacetates and other .beta.ketoesters is provided, involving reaction of nitrogen, oxygen or sulfur nucleophiles with a tertiaryalkyl acetoacetate or tertiaryalkyl .beta.-ketoester.Type: GrantFiled: February 25, 1992Date of Patent: April 27, 1993Assignee: Eastman Kodak CompanyInventors: J. Stewart Witzeman, W. Dell Nottingham
-
Patent number: 5202461Abstract: A 3-substituted 2-hydroxy3-formylpropionic ester of the formula I ##STR1## where R.sup.1 is lower alkyl, and R.sup.2 is straight-chain or branched alkyl of 1 to 10 carbon atoms, is obtained by adding an alkanal of the formula II ##STR2## and an alkyl glyoxylate of the formula III ##STR3## simultaneously to a catalyst system composed of a salt or a mixture of a secondary amine and a carboxylic acid in such a way that the temperature does not exceed 90.degree. C., preferably 80.degree. C., or else adding one of the reactants of the formula II or III to a mixture of the catalyst system described above and the other reactant in such a way that the temperature does not exceed 90.degree. C. The 2-hydroxy-3-formylpropionic ester of the formula I can be converted by treatment with dehydrating agents, especially acetic anhydride, into good yields of the corresponding 3-substituted 3-formylacrylic ester.Type: GrantFiled: October 5, 1990Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Juergen Frank
-
Patent number: 5187307Abstract: In the catalyzed gas phase oxidative dehydrogenation of alkyl glycolate with an oxygen source in the presence of a metallic silver catalyst, the selectivity of from 500 to about 5000 ppm the reaction is increased at high conversion rates by the addition of methylene chloride to the reactants.Type: GrantFiled: October 23, 1990Date of Patent: February 16, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: George E. Heinsohn
-
Patent number: 5126478Abstract: The process in which alkyl glyoxylates are prepared by the catalytic oxidative dehydrogenation of the corresponding alkyl glycolates is improved by carrying out the process in at least two adiabatic reaction stages in series, in which no more than about 60 percent of the stoichiometric amount of oxygen is used in the first stage.Type: GrantFiled: October 4, 1989Date of Patent: June 30, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: George E. Heinsohn
-
Patent number: 5107015Abstract: The preparation of 2-formyl-2-methyl succinates by reacting itaconates with carbon monoxide and hydrogen in contact with a catalyst system comprising rhodium and a tertiary phosphorus compound, wherein the reaction is carried out under a pressure of from 90 to 325 bar.Type: GrantFiled: October 24, 1990Date of Patent: April 21, 1992Assignee: BASF AktiengesellschaftInventors: Werner Bertleff, Gerhard Butz
-
Patent number: 5093518Abstract: Glycerol derivatives of general formula (I)CH.sub.2 --ORCH--OR.sub.1 (I)CH.sub.2 --OR.sub.2in which R=allyl, methylallyl, acryloyl or methacryloyl, R.sub.1 =R.sub.2 =glyoxyloyl, R.sub.1, R.sub.2 =H, glyoxyloyl; their preparation process, their use as cross-linking agents and cross-linking or cross-linkable compositions containing them.Application in the textile or paper industry.Type: GrantFiled: January 10, 1990Date of Patent: March 3, 1992Assignee: Societe Francaise HoechstInventors: Didier Wilheim, Fernand Cuirassier, Alain Blanc
-
Patent number: 5010200Abstract: This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;R.sup.2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy;R.sup.3 is selected from hydrogen and halogen;R.sup.4 is the residue of an alcohol of formula R.sup.4 -OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; andX is selected from oxygen and sulphur.Type: GrantFiled: February 16, 1990Date of Patent: April 23, 1991Assignee: Imperial Chemical Industries PLCInventors: Edward McDonald, Roger Salmon, Alan J. Whittle, Michael G. Hutchings
-
Patent number: 5003102Abstract: 5-Formylvaleric esters are prepared by a process which comprises the following steps:(a) Hydroformylation of a pentenoic ester by reaction with carbon monoxide and hydrogen at elevated temperatures and under superatmospheric pressure in the presence of a carbonyl complex of a metal of group 8 of the Periodic Table with formation of a mixture of 5-, 4- and 3-formylvaleric esters,(b) Isolation of the 5-formylvaleric ester from the resulting mixture of 5-, 4- and 3-formylvaleric esters, a mixture essentially consisting of 4- and 3-formylvaleric esters remaining,(c) Cleavage of the mixture essentially consisting of 4- and 3-formylvaleric esters at from 50.degree. to 400.degree. C. in the presence of a catalyst to give pentenoic esters and(d) Recycling of the pentenoic esters to stage (a).Type: GrantFiled: June 15, 1988Date of Patent: March 26, 1991Assignee: BASF AktiensellschaftInventors: Werner Bertleff, Rolf Fischer, Rudolf Kummer, Franz Merger, Heinz-Walter Schneider
-
Patent number: 4968833Abstract: The invention relates to a process for the preparation of a glyoxylic acid ester by oxydehydrogenation of the corresponding glycolic acid ester in the gas phase over a supported catalyst in a tubular reactor. The catalyst support consists of at least one cylindrical monolith which essentially has the same diameter as the reactor tube and contains channels with a diameter of 1 to 10 mm leading from the inlet to the outlet of the reactor tube. 60 to 90% of the monolith volume is formed by hollow spaces.Type: GrantFiled: January 11, 1985Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Robert K. Driscoll, Ernst I. Leupold, Wolfgang Ebertz, Friedrich Wunder
-
Patent number: 4931590Abstract: Adipic acid is prepared by a process which comprises the following steps:(a) Hydroformylation of a pentenoic ester by reaction with carbon monoxide and hydrogen at elevated temperatures and under superatmospheric pressure in the presence of a cobalt carbonyl or rhodium carbonyl complex with formation of a mixture of 5-, 4- and 3-formylvaleric esters,(b) isolation of the 5-formylvaleric ester from the resulting mixture of 5-, 4- and 3-formylvaleric esters, a mixture essentially consisting of 4- and 3-formylvaleric esters remaining,(c) dehydrocarbonylation of the mixture consisting essentially of 4- and 3-formylvaleric esters in the presence of one or more elements of subgroup 8 of the Periodic Table at from 50.degree. to 400.degree. C.Type: GrantFiled: June 10, 1988Date of Patent: June 5, 1990Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Franz Merger, Werner Bertleff, Rolf Fischer
-
Patent number: 4910328Abstract: .omega.-Formylalkanecarboxylic esters are prepared by hydroformylation of an alkenecarboxylic ester with carbon monoxide and hydrogen at elevated tempertures and under superatmospheric pressure in the presence of a cobalt carbonyl complex by a process in which an .alpha.,.beta.-unsaturated alkenecarboxylic ester is hydroformylated in the presence of from 0.01 to 1 mol %, calculated as cobalt, of a cobalt carbonyl complex, while maintaining a conversion of from 10 to 70% of .alpha.,.beta.-unsaturated alkenecarboxylic esters.Type: GrantFiled: June 15, 1988Date of Patent: March 20, 1990Assignee: BASF AkteingesellschaftInventors: Werner Bertleff, Robert Maerkl, Michael Roeper
-
Patent number: 4900864Abstract: A process of this invention for producing glyoxylate esters is carried out by contacting a with a catalyst comprising ferric phosphate on an alumina supportfeed composition comprising an oxygen containing gas and a vaporized lower alkyl ester of glycolic acid. The process of the invention can be carried out as either a fixed bed or a fluid bed operation.Type: GrantFiled: August 9, 1988Date of Patent: February 13, 1990Inventors: Prakasa R. Anantaneni, Tao P. Li
-
Patent number: 4873362Abstract: 2-Substituted 4-acyloxy-2-butenals of the general formula I ##STR1## where R.sup.1 is alkyl of 1 to 12 carbon atoms which may be substituted by cycloalphatic, aromatic or heterocyclic radicals, by alkenyl or alkynyl or by hydroxyl, ether, thioether, acetoxy acyl, alkylamino, carboxyl or carbalkoxy, and R.sup.2 is acyloxy, are prepared by reacting a monosubstituted acetaldehyde of the general formula II ##STR2## where R.sup.2 has the abovementioned meaning, with an aldehyde of the general formula III ##STR3## where R.sup.1 has the abovementioned meaning, in the presence of a linear or cyclic secondary amine and of an organic acid at from 20.degree. to 100.degree. C.Type: GrantFiled: November 2, 1987Date of Patent: October 10, 1989Assignee: BASF AktiengesellschaftInventors: Franz Merger, Rolf Fischer, Hans Horler
-
Patent number: 4870199Abstract: Process for the synthesis of compounds of the formula ##STR1## in R[R*,S*] enantiomeric form, wherein each P.sub.1 is independently an hydroxy group-protecting group, andR.sub.2z is C.sub.1-4 alkyl, benzyl or allyl,comprising, as a key step when R.sub.2z is R.sub.2x, the reaction of the compound of the formula ##STR2## in (S) enantiomeric form with a compound of the formulaMg.sup. .circle.+2 (.sup..crclbar. OOC--CH.sub.2 --COOR.sub.2x).sub.2to obtain a compound of the formula ##STR3## in (S) enantiomeric form, and, as a key step when R.sub.2z is R.sub.2y, the reaction of a compound of the formula ##STR4## in (S) enantioimeric form with a compound of the formulaLi.sup..sym..crclbar. CH.sub.2 --COOR.sub.2yto obtain a compound of the formula ##STR5## in (S) enantiomeric form, wherein R.sub.2x is primary or secondary C.sub.1-4 alkyl, benzyl or allyl,R.sub.2y is C.sub.1-4 alkyl not containing an asymmetric carbon atom, andR.sub.Type: GrantFiled: March 10, 1988Date of Patent: September 26, 1989Assignee: Sandoz Pharm. Corp.Inventors: Kau-Ming Chen, Goetz E. Hardtmann, Prasad K. Kapa, George T. Lee, Jerome Linder, Sompong Wattanasin
-
Patent number: 4867849Abstract: There is disclosed an improved process for the manufacture of glyoxylic acid obtained by oxidation of glycolic acid. For processing purposes alkyl esters of these acids are employed. Increased efficiency is obtained by recovering glycolate rich streams from one or more distillation operations and after treatment to remove acetic acid by-product the streams are recycled to the oxidation reaction.Type: GrantFiled: July 25, 1988Date of Patent: September 19, 1989Inventors: Dario R. Cova, John M. Thorman
-
Patent number: 4849543Abstract: This invention concerns a process for the production of diesters by hydroformylation/Michael addition of alkyl acrylates, which comprises contacting the alkyl acrylate with carbon monoxide and hydrogen in the presence of a catalyst system comprising a rhodium-containing compound, excess phosphine-containing ligand, a nitrogen-containing compound and a solvent at a temperature of 70.degree.-150.degree. C. and a pressure of 500-4000 psi.Type: GrantFiled: November 15, 1985Date of Patent: July 18, 1989Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
-
Patent number: 4820385Abstract: An improved process for separating high purity alkyl glyoxylate from complex mixtures containing alkyl glyoxylate, alkyl glycolate, water, alcohol and miscellaneous impurities by an azeotropic distillation operation using an azeotroping agent selected from the group consisting of methylene dichloride, 1,1,1--trichloroethane, and benzene.Type: GrantFiled: February 18, 1988Date of Patent: April 11, 1989Assignee: Monsanto CompanyInventors: Dario R. Cova, John M. Thorman
-
Patent number: 4801738Abstract: .delta.-Formylvalerates are prepared by a process wherein a 3-pentenoate is treated with an isomerization catalyst at elevated temperatures and a 4-pentenoate is distilled off, and the resulting 4-pentenoate is reacted with carbon monoxide and hydrogen at from 80 to 160.degree. C. under from 1 to 30 bar in the presence of a rhodium carbonyl complex which has been modified with tertiary organic phosphines or phosphites.Type: GrantFiled: May 9, 1984Date of Patent: January 31, 1989Assignee: BASF AktiengesellschaftInventors: Heinz-Walter Schneider, Rudolf Kummer, Volker Taglieber
-
Patent number: 4709097Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.Type: GrantFiled: April 14, 1986Date of Patent: November 24, 1987Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
-
Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
-
Patent number: 4650890Abstract: 7-Substituted lower alkyl hept-6-enoates and 4-hydroxy-tetrahydropyran-2-ones bearing 6-olefinic substituents (E), (Z), ethyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enates are prepared by a multi-step process involving lower alkyl 3,5-dihydroxy-hept-6-enates. The final products are useful as anti hypercholesteremic agents.Type: GrantFiled: July 26, 1985Date of Patent: March 17, 1987Assignee: Sandoz Corp.Inventors: Charles F. Jewell, Jr., James R. Wareing
-
Patent number: 4647688Abstract: Fatty ethers are provided which are lower alkyl ethers cyano-substituted lower alkyl ethers, ester ethers or amide ethers of fatty alcohols substituted with at least one of the following substituents: formyl, methylol, or acryloxymethyl. The substituted fatty ethers are useful as monomers in a wide variety of polymer systems.Type: GrantFiled: February 28, 1985Date of Patent: March 3, 1987Assignee: Henkel CorporationInventors: Michael J. Virnig, James P. Clark, Kenneth D. MacKay
-
Patent number: 4638000Abstract: Novel condensed seven-membered ring compounds of the formula: ##STR1## [wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, trifluoromethyl, lower alkyl or lower alkoxy, or both jointly form tri- or tetramethylene; R.sup.3 and R.sup.5 are independently hydrogen, lower alkyl or aralkyl; R.sup.4 is hydrogen or lower alkyl; R.sup.6 is a condensed or non-condensed hetero-alicyclic containing at least one atom of N, O and S as a ring-forming atom which may be substituted; A is an alkylene chain; n is 1 or 2] and salts thereof.These compounds exhibit inhibitory activity on angiotensin converting enzyme and so forth, and are of value as an agent for diagnosis, prevention and treatment of circulatory diseases, such as hypertension, cardiopathy and cerebral apoploxy.Type: GrantFiled: January 14, 1985Date of Patent: January 20, 1987Assignee: Takeda Chemical Industries, Ltd.Inventors: Hirosada Sugihara, Kohei Nishikawa, Katsumi Ito
-
Patent number: 4616092Abstract: An optically active or inactive .beta.-formyl-.beta.-hydroxy ester of the formula (1), ##STR1## wherein R.sup.1 represents a C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.14 aralkyl group, R.sup.2 represents a C.sub.1 -C.sub.4 alkyl group and R.sup.3 represents a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group, and a method for producing the same which comprises reacting an optically active or inactive compound of the formula (2), ##STR2## wherein A represents a C.sub.6 -C.sub.14 aryl group and R.sup.1 is as defined above, with an .alpha.-halo ester of the formula (3), ##STR3## wherein X represents a halogen atom and R.sup.2 and R.sup.3 are as defined above, in the presence of zinc, followed by hydrolysis, or reacting an ester of the formula (4),R.sup.3 CH.sub.2 COOR.sup.2 (4)wherein R.sup.2 and R.sup.Type: GrantFiled: February 18, 1981Date of Patent: October 7, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
-
Patent number: 4614816Abstract: A carboxylic acid or an ester thereof having at least two carbon atoms more than formic acid is prepared by reacting at elevated temperature e.g. 100.degree. to 250.degree. C. formic acid or a formate ester with an olefin e.g. ethylene in the presence of, as catalyst, a Group VIII noble metal e.g. iridium, preferably promoted by iodide, to cause addition of the formic acid or ester to the olefin and form the a higher acid e.g. propionic acid or ester thereof.A strong acid such as a sulphonic acid may be used as a copromoter. The catalyst is employed in solution.Type: GrantFiled: October 13, 1983Date of Patent: September 30, 1986Assignee: BP Chemicals LimitedInventors: David J. Drury, Peter S. Williams
-
Patent number: 4558153Abstract: Carboxylic acids having two or more carbon atoms than formic acid, or esters of such carboxylic acids are prepared by reacting either formic acid or an ester of formic acid with an olefin at elevated temperature in the presence of a Group VIB metal catalyst. The Group VIB metal which is chromium, molybdenum or tungsten is suitably added as a carbonyl or carbonyl halide. In addition to the catalyst a halide promoter and a phosphorus containing copromoter may optionally be added. The process can be used, for example to prepare propionic acid or a propionic acid ester from ethylene and either formic acid of an ester of formic acid.Type: GrantFiled: October 23, 1984Date of Patent: December 10, 1985Assignee: BP Chemicals LimitedInventor: John Cook
-
Patent number: 4515984Abstract: A process is described for the preparation of an alkali metal formyl acetic acid alkyl ester by reaction of acetic acid alkyl ester, an alkali-metal alcoholate and carbon monoxide at elevated pressure and elevated temperature, the improvement wherein an excess of acetic acid alkyl ester referred to the alkali-metal alcoholate is employed and the reaction is carried out in the absence of a solvent.Type: GrantFiled: September 20, 1982Date of Patent: May 7, 1985Assignee: Dynamit Nobel AktiengesellschaftInventor: Moustafa El-Chahawi
-
Patent number: 4502923Abstract: High purity alkyl glyoxylate is produced from complex mixtures containing alkyl glyoxylate, alkyl glycolate, water, alcohol and miscellaneous impurities. High purity alkyl glyoxylate is useful in the synthesis of alkyl glyoxylate polymers.Type: GrantFiled: October 6, 1983Date of Patent: March 5, 1985Assignee: Monsanto CompanyInventors: David R. Dyroff, Yueting Chou, Dario R. Cova
-
Patent number: 4487957Abstract: A novel alkyl 4-methyl-3-formyl-penten-1-oate of the formula ##STR1## wherein R is alkyl of 1 to 5 carbon atoms and the dotted lines represent a double bond in the 3,4 or 4,5-position and their preparation and novel intermediates therefore and a novel process for the preparation of 4-methyl-3-formyl-pent-3-en-1-oic acid which is an intermediate for the preparation of compounds of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of hydrogen and the residue of an alcohol R.sub.3 OH by the process of European Patent Application Ser. No. 0023849 published Feb. 11, 1981, which are used to prepare very active insecticidal esters.Type: GrantFiled: April 21, 1983Date of Patent: December 11, 1984Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
-
Patent number: 4421928Abstract: Novel 4-methyl-3-formyl-pentanoic acid derivative of the formula ##STR1## wherein Hal is a halogen, R.sub.1 is alkyl of 1 to 12 carbon atoms and A and B are .dbd.0 or A is halogen and B is --OR.sub.2 and R.sub.2 is alkyl of 1 to 12 carbon atoms, their preparation and their use as intermediates.Type: GrantFiled: February 25, 1982Date of Patent: December 20, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
-
Patent number: 4421924Abstract: A synthetic route to ascorbic acid is provided in which a 3,5:4,6-protected derivative of gulonic acid is prepared from gulono-1,4-lactone. Oxidation of the derivative and hydrolysis of the resulting product affords 2-ketogulonic acid or ester thereof which can be readily converted to ascorbic acid by known methods.Type: GrantFiled: April 24, 1981Date of Patent: December 20, 1983Assignee: Pfizer Inc.Inventor: Thomas C. Crawford
-
Patent number: 4357282Abstract: Fluorinated carbonyl compounds are prepared by contacting a fluorinated methyl or ethyl ether containing at least one methoxylated carbon atom-containing group selected from: --CF.sub.2 OR.sup.3, .dbd.CFOR.sup.3, ##STR1## wherein R.sup.3 is CH.sub.3 or C.sub.2 H.sub.5, with a catalyst selected from:SbX.sub.5, TaX.sub.5, NbX.sub.5, AsX.sub.5, BiX.sub.5, TiX.sub.4, ZrX.sub.4, HfX.sub.4, FeX.sub.3,mixtures of SbX.sub.3 and SbX.sub.5, ZM'X'.sub.6, and mixtures of ZM'X'.sub.6 and M'X.sub.5 where X, independently, is F, Cl, Br or I, X' is F or Cl; and Z is H, NO, O.sub.2, alkali metal or NY.sub.4 where Y, independently, is H or alkyl of 1 to 6 carbon atoms, and M' is Sb or As at a temperature of -20.degree. to 200.degree. C.Type: GrantFiled: April 3, 1981Date of Patent: November 2, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: Daniel G. Anderson, David C. England, Alwin S. Milian, Jr.
-
Patent number: 4342694Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified. The halomethyl bicyclic lactone is a useful intermediate for the preparation of insecticidal cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates or cis-3-(2-halo-2-trihalomethylethenyl)-2,2-dimethylcyclopropanecarboxylates .Type: GrantFiled: June 23, 1980Date of Patent: August 3, 1982Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
-
Patent number: 4340748Abstract: The invention relates to a process for the manufacture of glyoxylic acid esters by catalytic dehydrogenation of glycolic acid esters in the gaseous phase.Type: GrantFiled: February 6, 1980Date of Patent: July 20, 1982Assignee: Hoechst AktiengesellschaftInventors: Herbert Baltes, Ernst I. Leupold, Friedrich Wunder
-
Patent number: 4334042Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.Type: GrantFiled: July 23, 1979Date of Patent: June 8, 1982Assignee: Kuraray Co. Ltd.Inventors: Mitsuo Matsumoto, Masuhiko Tamura
-
Patent number: 4314071Abstract: Monoesters of symmetrical dicarboxylic acids and symmetrical diols are prepared in high yield by reacting a diacid or a diol with a monohydric alcohol or monocarboxylic acid, respectively, in an aqueous solution. The resultant monoester is removed from the aqueous solution immediately after its formation by continuous extraction with a nonpolar solvent.Type: GrantFiled: May 12, 1980Date of Patent: February 2, 1982Inventor: James H. Babler
-
Patent number: 4311706Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.Type: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
-
Patent number: 4268688Abstract: This invention relates to a process for the preparation of optically active aldehydes by the asymmetric catalytic hydroformylation of olefins. The process comprises the hydroformylation of olefinically unsaturated prochiral compounds in the presence of an optically active coordination compound containing a metal which is selected from the group consisting of rhodium, iridium, and cobalt.This invention describes a generalized process for the asymmetric hydroformylation of a wide variety of olefins in which a preponderance of one optical isomer is produced. It is especially useful for the preparation of natural products which may require the presence of only one optical isomer for their utilization, for example, as flavors, fragrances, and medications.The catalyst systems for the process of this invention are formed in the presence of carbon monoxide and hydrogen, from coordination compounds consisting of a central metal atom, rhodium, iridium, or cobalt, and at least one optically active ligand, e.g.Type: GrantFiled: February 16, 1973Date of Patent: May 19, 1981Assignee: Monsanto CompanyInventors: Harold B. Tinker, Arthur J. Solodar
-
Patent number: 4237054Abstract: A method for the total synthesis of (1RS,4SR,5RS)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyc lo [3.2.1] octane-1-acetic acid is described. The compound is active as a utero-evacuant agent.Type: GrantFiled: May 18, 1979Date of Patent: December 2, 1980Assignee: Ortho Pharmaceutical CorporationInventor: Robert H. K. Chen
-
Patent number: 4235780Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified.Type: GrantFiled: November 1, 1979Date of Patent: November 25, 1980Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
-
Patent number: 4217290Abstract: This invention consists of a process for preparing bifunctional aliphatic organic compounds of at least 6 carbon atoms, wherein a cycloaliphatic oxyhydroperoxide is reacted with an alpha-olefine having its double bond activated by a conjugate electron-attracting group, in the presence of a bivalent Cr salt, a bivalent V salt or a trivalent Ti salt.Type: GrantFiled: June 20, 1979Date of Patent: August 12, 1980Assignee: Brichima S.p.A.Inventors: Paolo Maggioni, Francesco Mauri, Attilio Citterio
-
Patent number: 4119648Abstract: The present specification provides novel intermediates and novel processes for the synthesis of various side chain and skeletal analogs of Thromboxane B.sub.2 (11.beta.-homo-11.alpha.-oxa-PGF.sub..alpha.). These analogs are particularly and especially useful as reproductive cycle control agents.Type: GrantFiled: September 6, 1977Date of Patent: October 10, 1978Assignee: The Upjohn CompanyInventor: William P. Schneider
-
Patent number: 4107427Abstract: The present specification provides novel intermediates and novel processes for the synthesis of various side chain and skeletal analogs of Thromboxane B.sub.2 (11.beta.-homo-11a-oxa-PGF.sub.2.alpha.). These analogs are particularly and especially useful as reproductive cycle control agents.Type: GrantFiled: August 20, 1976Date of Patent: August 15, 1978Assignee: The Upjohn CompanyInventor: Robert C. Kelly
-
Patent number: 4100350Abstract: The invention provides 3-(2-formyl-3-hydroxy-5-oxocyclopent-1-enyl)-p ropanoic acid and derivatives thereof having anti-thrombotic activity coupled with low toxicity. Also provided is a method for preparing such compounds by subjecting a 3-[3-hydroxy-5-oxo-2-(.beta.-styryl)cyclopent-1-enyl]-propanoic acid or derivative thereof to oxidative cleavage.Type: GrantFiled: March 2, 1977Date of Patent: July 11, 1978Assignee: Lilly Industries Ltd.Inventors: William Dawson, Michael John Foulis, Norman James Albert Gutteridge, Colin William Smith
-
Patent number: 4092356Abstract: This invention relates to 11,12-secoprostaglandins and processes for their manufacture. These compounds have prostaglandin-like biological activity and are particularly useful as renal vasodilators, for the treatment of hypertension, for the prevention of thrombus formation, in preventing gastric secretion, and as regulators of the immune response.Type: GrantFiled: December 17, 1976Date of Patent: May 30, 1978Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., John B. Bicking, Robert L. Smith
-
Patent number: 4073919Abstract: Novel 5-thiazole alkanols of the formula ##STR1## wherein R is alkyl of 1 to 5 carbon atoms, n is an integer from 2 to 7 and R.sub.1 is selected from the group consisting of hydrogen and acyl of an alkanoic acid of 2 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having a marked antilipolytic activity and useful as intermediates and their preparation.Type: GrantFiled: February 2, 1976Date of Patent: February 14, 1978Assignee: Roussel UclafInventors: Andre Poittevin, Vesperto Torelli