Aldehyde Or Ketone Group In Acid Moiety Patents (Class 560/174)
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Patent number: 4465863Abstract: Described are compounds defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl with the provisos that:(i) the sum total of carbon atoms in R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is three;(ii) when R.sub.7 is methyl, then R.sub.5 and R.sub.6 are both methyl, and(iii) when either R.sub.3 or R.sub.4 is methyl, then R.sub.7 is hydrogenand wherein R.sub.8 represents hydrogen, acetyl, alkoxyacyl, hydroxyacyl, or alkali metal carboxylate; and R.sub.9 is hydrogen or allyl with the additional proviso that R.sub.8 and R.sub.9 are not both hydrogen.Also described is the use of the subgenus of such compounds defined according to the structure: ##STR2## in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid nonionic, cationic, anionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations and the like.Type: GrantFiled: November 12, 1982Date of Patent: August 14, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz, Marie R. Hanna
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Patent number: 4460786Abstract: The selective addition of a compound having an activated carbon atom onto the carbon atom in the 4-position of a buta-1,3-diene carrying a hydrocarbon substituent on the carbon atom in the 2-position is achieved by reacting the compound having the activated carbon atom with the buta-1,3-diene carrying the hydrocarbon substituent in water or in an aqueous-alcoholic mixture in the presence of a catalyst which consists of at least one water-soluble phosphine and at least one rhodium compound, the catalyst being in solution in the water or aqueous alcoholic mixture. The products obtained are useful as precursors of intermediates for the synthesis of vitamins and perfumes.Type: GrantFiled: June 7, 1983Date of Patent: July 17, 1984Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4460793Abstract: A process for the production of a monochloromethyl ketone of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 each independently is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkinyl or aryl radical, orR.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted carbocyclic ring,comprising reacting a 1,1-dichloroalkene of the formula ##STR2## with a phenolate of the formula ##STR3## in which R.sup.4 each independently is a halogen atom, a nitro group, or an optionally substituted alkyl, alkoxy or aryl radical,n is 0, 1, 2 or 3, andM is one equivalent of an alkali metal ion or alkaline earth metal ion,thereby to obtain a phenyl ether intermediate, and then subjecting the phenyl ether intermediate to an acid hydrolysis. The products are useful as intermediates in the synthesis of fungicides.Type: GrantFiled: December 11, 1981Date of Patent: July 17, 1984Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4442302Abstract: It has been found that excellent quality photopolymer printing plates having resistance to alcohol-based inks can be prepared from photopolymer compositions comprising a chain extended, liquid, terminally olefinically unsaturated polymer; from about 1% to about 50% by weight based on the weight of the polymer of at least one ethylenically unsaturated monomer; from about 0.1% to about 10% by weight based on the weight of the polymer of photoinitiator; and from about 0.01% to about 2% by weight based on the weight of the polymer of a stabilizer.Type: GrantFiled: July 2, 1982Date of Patent: April 10, 1984Assignee: Hercules IncorporatedInventor: Rudolph L. Pohl
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Patent number: 4442303Abstract: In one of its embodiments this invention provides a process for recovering C.sub.4 -C.sub.6 dicarboxylic acid components contained in a waste byproduct stream derived from a reaction system in which adipic acid is produced by nitric acid oxidation of cyclohexanone/cyclohexanol.An important aspect of the process is the esterification and extraction of the C.sub.4 -C.sub.6 dicarboxylic acids in the aqueous byproduct stream with a mixture of C.sub.1 -C.sub.3 alkanol and C.sub.6 -C.sub.20 alkanol, and the subsequent recovery of di(C.sub.6 -C.sub.20 alkyl) esters of succinic acid, glutaric acid and adipic acid.In a broader aspect this invention provides a process for recovery of water miscible organic acid components contained in an aqueous solution as C.sub.6 -C.sub.20 alkyl esters of the organic acids.Type: GrantFiled: December 9, 1980Date of Patent: April 10, 1984Assignee: El Paso Products CompanyInventor: Samuel S. Mims
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Patent number: 4438278Abstract: Compounds useful in making crosslinkable polymers having the formula (I): ##STR1## wherein R is hydrogen or methyl; R.sup.1 is cyano or ##STR2## wherein R.sup.2 is alkyl; Z is --X--R.sup.3 --X--or ##STR3## wherein each --X-- is --O-- or --NR.sup.4 --, provided at least one --X-- is --NR.sup.4 -- wherein R.sup.4 is hydrogen or alkyl, R.sup.3 is divalent hydrocarbon and D.sub.1 and D.sub.2 together are the carbon atoms necessary to complete a 5 to 7 membered ring. These compounds can be homopolymerized or copolymerized with each other or with other polymerizable ethylenically unsaturated monomers to give crosslinkable polymers. Such polymers can be purified by conventional purification techniques such as dialysis, diafiltration, ultrafiltration without losing their capability of crosslinking. The resulting purified polymers are particularly useful in photographic materials as gelatin extenders, binders or polymeric color couplers.Type: GrantFiled: April 19, 1982Date of Patent: March 20, 1984Assignee: Eastman Kodak CompanyInventors: Ignazio S. Ponticello, Kenneth R. Hollister, Richard C. Tuites
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Patent number: 4426321Abstract: This invention discloses a number of novel odorant alkadienyl ketones, alcohols and oximes having from 9 to 15 carbon atoms, processes for making same and odorant compositions containing same.Type: GrantFiled: July 24, 1981Date of Patent: January 17, 1984Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4421915Abstract: Compounds useful in making crosslinkable polymers having the formula (I): ##STR1## wherein R is hydrogen or methyl; R.sup.1 is cyano or ##STR2## wherein R.sup.2 is alkyl; Z is --X--R.sup.3 --X-- or ##STR3## wherein each --X-- is --O-- or --NR.sup.4 --, provided at least one --X-- is --NR.sup.4 -- wherein R.sup.4 is hydrogen or alkyl R.sup.3 is divalent hydrocarbon and D.sub.1 and D.sub.2 together are the carbon atoms necessary to complete a 5 to 7 membered ring. These compounds can be homopolymerized or copolymerized with each other or with other polymerizable ethylenically unsaturated monomers to give crosslinkable polymers. Such polymers can be purified by conventional purification techniques such as dialysis, diafiltration, ultrafiltration without losing their capability of crosslinking. The resulting purified polymers are particularly useful in photographic materials as gelatin extenders, binders or polymeric color couplers.Type: GrantFiled: April 19, 1982Date of Patent: December 20, 1983Assignee: Eastman Kodak CompanyInventors: Ignazio S. Ponticello, Kenneth R. Hollister, Richard C. Tuites
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Patent number: 4414418Abstract: Process for the production of dimedone from isophorone. The isophorone is converted in the presence of a solvent with ozone into an ozone-addition product. An alcohol corresponding to the ester radical is added at the latest after the formation of the ozone-addition product for the formation of the intermediate product, 3,3-dimethyl-5-oxo-hexanoic acid ester. The ozone addition product is heated in the presence of acids to a temperature of 20.degree. to 150.degree. C. The 3,3-dimethyl-5-oxo-hexanoic acid ester is isolated thereby. The ester is then converted in a further step into dimedone by treatment of the ester with an alkali alcoholate in an anhydrous milieu.Type: GrantFiled: May 19, 1982Date of Patent: November 8, 1983Assignee: Lonza Ltd.Inventor: Pavel Lehky
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Patent number: 4414400Abstract: Process for the production of tetronic acid from 4-haloacetoacetic ester. The 4-haloacetoacetic ester is transformed into the corresponding 4-tertiary-butoxyacetoacetic ester and the latter is converted by cyclizing ether cleavage into tetronic acid. Preferably the cyclizing ether cleavage is carried out thermolytically at a temperature above 100.degree. C. or is carried out by treatment with an acid at a temperature of 0.degree. to 30.degree. C. Tertiary-butoxyacetoacetic acid ethyl ester is a new compound.Type: GrantFiled: June 14, 1982Date of Patent: November 8, 1983Assignee: Lonza Ltd.Inventors: Raimund Miller, Leander Tenud
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Patent number: 4401827Abstract: Novel acyl-derivatives of the .beta.-hydroxy-.gamma.-butyrobetaine are disclosed (typically pyruvyl carnitine hydrochloride) which are useful therapeutic agents in the treatment of cardiac disorders, hyperlipidoemias and hyperlipoproteinemias.Type: GrantFiled: December 28, 1981Date of Patent: August 30, 1983Assignee: Sigma-TauInventor: Paolo de Witt
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Patent number: 4390702Abstract: A 3-substituted-3-fluoropyruvic acid and its ester and salt of the formula: ##STR1## wherein R is a lower alkyl group, a lower alkanoyl group, a fluorinated lower alkanoyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group and R' is a hydrogen atom, an ester-forming residue or a salt-forming residue, and their production.Type: GrantFiled: December 29, 1980Date of Patent: June 28, 1983Assignees: Daikan Kogyo Co., Ltd., Shionogi and Co., Ltd.Inventors: Susumu Misaki, Masahiro Suefuji, Tadahiko Tsushima, Hiroshi Tanida
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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.
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Patent number: 4346231Abstract: Compounds useful in making crosslinkable polymers having the formula (I): ##STR1## wherein R is hydrogen or methyl; R.sup.1 is cyano or ##STR2## wherein R.sup.2 is alkyl; Z is --X--R.sup.3 --X-- or ##STR3## wherein each --X-- is --O-- or --NR.sup.4 --, provided at least one --X-- is --NR.sup.4 -- wherein R.sup.4 is hydrogen or alkyl, R.sup.3 is divalent hydrocarbon and D.sub.1 and D.sub.2 together are the carbon atoms necessary to complete a 5 to 7 membered ring. These compounds can be homopolymerized or copolymerized with each other or with other polymerizable ethylenically unsaturated monomers to give crosslinkable polymers. Such polymers can be purified by conventional purification techniques such as dialysis, diafiltration, ultrafiltration without losing their capability of crosslinking. The resulting purified polymers are particularly useful in photographic materials as gelatin extenders, binders or polymeric color couplers.Type: GrantFiled: June 9, 1980Date of Patent: August 24, 1982Inventors: Ignazio S. Ponticello, Kenneth R. Hollister, Richard C. Tuites
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Patent number: 4339383Abstract: The invention relates to alkanolamido-.beta.-carboxylic acid esters of the formula I ##STR1## A full definition of the above formula will be found in claim 1 of the specification. These compounds are useful stabilizers for chlorinated thermoplastics.Type: GrantFiled: July 2, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wehner, Klaus-Peter Michaelis, Rainer Schneider
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Patent number: 4338253Abstract: Compounds represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.Type: GrantFiled: June 25, 1981Date of Patent: July 6, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4337350Abstract: The novel stereoselective and regioselective alkali metal borohydride reduction of 2,5-diketogluconic acid, alkyl esters or salts thereof to form 2-ketogulonic acid together with lesser amounts of 2-ketogluconic acid is disclosed. The 2-ketogulonic acid is readily converted to ascorbic acid.Type: GrantFiled: April 25, 1980Date of Patent: June 29, 1982Assignee: Pfizer Inc.Inventor: Glenn C. Andrews
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Patent number: 4335255Abstract: Ketoester of the formula ##STR1## .alpha.-carboxylate-.omega.-acyl fluoride of the formula ##STR2## vinyl ether of the formula ##STR3## divinyl ether of the formula ##STR4## allyl ether of the formula ##STR5## and film-forming copolymers, useful as molding resins, of the vinyl ether and/or the divinyl ether or the allyl ether and a fluorinated vinyl monomer, for example, tetrafluoroethylene, wherein, in the above formulas, n is 0 to 6, p is 0 to 7, X is CO.sub.2 M, CO.sub.2 R, CO.sub.2 H, CONH.sub.2, COF, COCl or CN, M is alkali metal, ammonium or quaternary ammonium and R is C.sub.1-8 alkyl, selected copolymers, after hydrolysis, being water-wettable and dyeable, exhibiting ion-exchange properties and being useful in curable fluoroelastomer compositions and, in film form, as the membrane in a chloroalkali electrolysis cell.Type: GrantFiled: April 3, 1980Date of Patent: June 15, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4329491Abstract: The present invention relates to crop culture and is particularly concerned with practices for conserving soil nitrogen and for supplying the soil nitrogen requirements for plant nutrition. These practices involve the employment, as active agent, of a novel butane compound having the formula ##STR1## wherein each Y is independently hydrogen, chloro-, bromo-, fluoro- or methyl; Z is a straight or branched chain alkyl of 1-4 carbon atoms; R is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo and n is an integer from 0 to 2.Type: GrantFiled: May 19, 1980Date of Patent: May 11, 1982Assignee: The Dow Chemical CompanyInventor: R. Garth Pews
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Patent number: 4327000Abstract: Stabilizer mixtures consisting of(a) a thioether of the formula I ##STR1## and (b) a stabilizer containing a metal selected from the group consisting of zinc, calcium, cadmium, barium, magnesium, tin or antimony, or also zinc in combination with at least one of the metals just referred to. The definitions of the substituents and symbols in formula I will be found in claim 1.These stabilizer mixtures ensure an excellent heat-stabilizing action in chlorinated thermoplastics.Type: GrantFiled: March 24, 1980Date of Patent: April 27, 1982Assignee: Ciba-Geigy CorporationInventors: Horst Muller, Hermann O. Wirth
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Patent number: 4325877Abstract: 5-Amino-4-oxo-pentanoic acids of the formula ##STR1## wherein R is CF.sub.3, CHF.sub.2 or CH.sub.2 F; R.sub.1 is H or akyl of 1-4 carbon atoms; and R.sub.2 is H or alkyl or 1-4 carbon atoms or benzyl, which are intermediates to ACE inhibitors or elastase inhibitors, are produced by reacting a 1-(methylthio)-1-methylsulfinyl)-2-R.sub.1 -ethylmetal with an ester of a 3-R-acrylic acid; optionally R.sub.2 -alkylating the thus-produced ester enolate anion of 4-(methylsulfinyl)-4-(methylthio)-5-R.sub.1 R-pentanoic acid followed by splitting off of methylsulfinic acid; reacting the thus-produced 2-R.sub.2 -5-R.sub.1 -4-(methylthio)-3-R-4-pentenoic acid ester with a source of Br.sup.+ to produce a 5-bromo-substituted acid or ester thereof otherwise corresponding to the desired 5-amino-4-oxo-pentanoic acid; and replacing the bromine atom with an amino group, e.g., via the corresponding 5-azido- and 5-N-acylamino- compounds, with hydrolysis of the ester group, if still remaining.Type: GrantFiled: June 16, 1980Date of Patent: April 20, 1982Assignee: Richardson-Merrell Inc.Inventors: Brian W. Metcalf, Jerry L. Adams
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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
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Patent number: 4305876Abstract: A process for asymmetrically hydrogenating through the use of microorganisms a double bond connected to tertiary carbon atom in an olefinic aliphatic compound to produce a tertiary, optically active aliphatic compound useful as an intermediate for optically active Vitamins E and K.Type: GrantFiled: November 24, 1978Date of Patent: December 15, 1981Assignee: Hoffmann-La Roche, Inc.Inventors: Richard Barner, Walter Boguth, Hans G. W. Leuenberger, Max Schmid, Reinhard Zell
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Patent number: 4303795Abstract: A process is provided for preparing pyrazolo-[1,5-c]quinazoline derivatives of the structure ##STR1## wherein X is O or S; R.sup.1 is hydrogen, lower alkyl, hydroxymethyl, phenyl-lower alkyl, phenyl or phenyl substituted with halogen, lower alkyl, lower alkoxy, or trifluoromethyl; R.sup.2 is lower alkoxy, phenyl-lower alkoxy, phenoxy, or phenoxy substituted with lower alkyl or lower alkoxy; and R.sup.3 and R.sup.4 are the same or different and are selected from the group consisting of hydrogen, alkyl of 1 to 4 carbons, alkoxy of 1 to 4 carbons, lower alkanoyloxy of 1 to 4 carbons, nitro, benzyloxy, benzyloxy having a single mono-lower alkoxy substituent, halogen, hydroxy, and trifluoromethyl, wherein quinolone compounds of the structure ##STR2## which are new intermediates, are reacted with a hydrazine compound to form a 5-(2-aminophenyl)-pyrazole which is then cyclized to the product.In addition, the above product may be reacted with a halogen acid to form the corresponding hydroxymethyl compound.Type: GrantFiled: July 23, 1980Date of Patent: December 1, 1981Assignee: E. R. Squibb & Sons, Inc.Inventors: Richard A. Conley, Margaret M. Lam, Leroy B. High
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Patent number: 4299973Abstract: A novel cyclopropene-carboxylate of the formula ##STR1## wherein R is alkyl of 1 to 6 carbon atoms and their preparation and a process using the compounds of formula I to obtain cis compounds of the formula ##STR2##Type: GrantFiled: August 28, 1980Date of Patent: November 10, 1981Assignee: Roussel UclafInventors: Michel Franck-Neumann, Michel Miesch
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Patent number: 4291170Abstract: Delta-keto-esters such as 4-oxopentane-1-carboxylic acid methyl ester and the like, are prepared in the presence of a primary amine, a Schiff base, or both, by reacting a ketone having at least one hydrogen atom in the alpha position and an alpha-beta unsaturated carboxylic acid ester in the presence of an acid according to the disclosed invention.Type: GrantFiled: May 20, 1977Date of Patent: September 22, 1981Assignee: Stamicarbon, B.V.Inventors: Sijbrandus E. Schaafsma, Johannes H. A. Hofman, Johannes E. L. Claassens
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Patent number: 4289917Abstract: Alkali metal oxides of cis- and trans-2,6,6-trimethylbicyclo(3.1.1)-heptan-2-ol are surprisingly effective bases in organic reactions calling for the use of a strong base, especially those reactions wherein abstraction of a proton from attachment to a carbon atom is postulated to occur in the mechanism.Type: GrantFiled: August 17, 1979Date of Patent: September 15, 1981Assignee: SCM CorporationInventors: Bernard J. Kane, Sean G. Traynor
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Patent number: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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Patent number: 4277418Abstract: An improvement in the alkoxylation of a compound having a reactive methylene group by contacting said compound with an orthoformic acid trialkyl ester in the presence of a catalyst, the improvement residing in employing at least 1.6 moles of orthoformic acid ester per mole of compound having a reactive methylene group and carrying out the process in the presence of a catalyst of the group of aliphatic carboxylic acids, anhydrides of aliphatic carboxylic acids, aromatic sulphonic acids, alkali metal alcoholates and alkanolamines.Type: GrantFiled: February 26, 1979Date of Patent: July 7, 1981Assignee: Dynamit Nobel AktiengesellschaftInventors: Otto Ackermann, Dieter Bretzinger, Herbert Schneidewind, Rudolf Stephan
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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: 4275225Abstract: The reaction of a polyfluorocarbonyl compound such as a polyfluoroketone or polyfluorocarboxylic acid fluoride with fluoride ion and a polyfluoroallyl chloride, bromide or fluorosulfate produces a polyfluoroallyloxy carboxylic acid or ester, e.g., CF.sub.2 .dbd.CFCF.sub.2 OCF.sub.2 CF.sub.2 COOH. The polyfluoroallyloxy compounds copolymerize with ethylenically unsaturated monomers such as tetrafluoroethylene, chlorotrifluoroethylene or vinylidene fluoride to form polymers which are moldable, and in some cases electrically conducting or are water-wettable and dyeable.Type: GrantFiled: May 1, 1980Date of Patent: June 23, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4267362Abstract: A process is described for the preparation of delta keto-acids wherein there is used as a catalyst the condensation adduct of a cyclic secondary amine with an .alpha.-.beta.-acrylic-type unsaturated compound, providing high selectivity and conversion results.Type: GrantFiled: August 17, 1979Date of Patent: May 12, 1981Assignee: Stamicarbon, B.V.Inventors: Peter J. N. Meyer, Josef M. Penders
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Patent number: 4254282Abstract: Lactones of the formula ##STR1## wherein R is hydrogen or a CX.sub.3 group, and each X is a chlorine or bromine atom, are converted to the known cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids or lower alkyl esters, from which pyrethroid insecticides are obtained.Type: GrantFiled: June 18, 1979Date of Patent: March 3, 1981Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Daiei Tunemoto
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Patent number: 4245122Abstract: A process is described for the preparation of allyl acetone (5-hexen-2-one) according to the reaction: ##STR1## wherein R is methyl or ethyl; X is chloro or bromo; M is sodium or potassium; and Q is sodium or potassium, the reaction being carried out (i) using a phase transfer agent and (ii) in a two phase system.Type: GrantFiled: December 5, 1979Date of Patent: January 13, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, Denis E. Hruza, Sr., John B. Hall
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Patent number: 4236021Abstract: An improved process for the manufacture of levulinic acid which comprises esterification of furfuryl alcohol in the presence of a different alcohol selected from unsubstituted primary and secondary carbon-chain or carbon-ring alcohols containing 1 to 10 carbon atoms in the presence of a small amount of acid as a catalyst, purification of the resulting levulinate ester by vacuum distillation of a mixture of the levulinate ester and a high boiling solvent and hydrolysis of the purified levulinate ester in the presence of water and a small amount of strong acid catalyst to yield levulinic acid-water mixture. The improvement resides in the purification being carried out prior to hydrolysis and in using a high boiling solvent in the purification step to prevent the formation of a solid resin.Type: GrantFiled: May 7, 1979Date of Patent: November 25, 1980Assignee: The B. F. Goodrich CompanyInventors: Chin C. Hsu, Dwight W. Chasar
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Patent number: 4234739Abstract: Glyoxylic acids or derivatives thereof are prepared by reacting an acyl nitrile compound with concentrated sulfuric acid in the presence of halide anion to form a first reaction product and then further reacting the first reaction product with a compound of the general formula ROH to form the desired glyoxylic acid or glyoxylic acid derivative.Type: GrantFiled: December 5, 1978Date of Patent: November 18, 1980Assignee: Stauffer Chemical CompanyInventors: James M. Photis, Fred S. Eiseman, Sidney M. Gister
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Patent number: 4232169Abstract: An operationally simple and economical process for preparing alpha-oxoesters is provided by reacting an acetylenic compound of formulaR--C.tbd.C--OR'with an oxidizing mixture composed of osmium tetroxide and an alkaline or alkaline earth chlorate and recovering the osmium tetroxide at the end of the reaction.Type: GrantFiled: April 24, 1979Date of Patent: November 4, 1980Assignee: Snamprogetti S.p.A.Inventors: Luciano Re, Alberto Brandt, Luciano Bassignani
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Patent number: 4232168Abstract: 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: June 13, 1977Date of Patent: November 4, 1980Assignee: Pfizer Inc.Inventor: Thomas C. Crawford
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Patent number: 4230880Abstract: The novel stereoselective and regioselective alkali metal borohydride reduction of 2,5-diketogluconic acid, alkyl esters or salts thereof to form 2-ketogluconic acid together with lesser amounts of 2-ketogluconic acid is disclosed. The 2-ketogluconic acid is readily converted to ascorbic acid.Type: GrantFiled: February 16, 1979Date of Patent: October 28, 1980Assignee: Pfizer Inc.Inventor: Glenn C. Andrews
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Patent number: 4229590Abstract: Alkyl pyruvates are prepared by oxidizing alkyl lactates in the presence of a silver catalyst of a defined particle size, at from 450.degree. to 700.degree. C. The products are starting materials for the preparation of drugs, synthetic resins and plastics.Type: GrantFiled: February 8, 1979Date of Patent: October 21, 1980Assignee: BASF AktiengesellschaftInventors: Christian Dudeck, Gunter Lehmann, Bernd Meissner, Hans Diem, Werner Fliege, Norbert Petri, Karl-Heinz Ross
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Patent number: 4221918Abstract: Carboxylic acid anhydrides are contacted with hydrogen in the presence of an insoluble metal hydrogenation catalyst and strong protonic acid to produce 1,1-diesters.Type: GrantFiled: October 30, 1978Date of Patent: September 9, 1980Assignee: Chevron Research CompanyInventor: Shigeto Suzuki
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Patent number: 4220604Abstract: An isoolefin is converted to a ketone, e.g., isobutylene to methyl ethyl ketone, by an oxidative rearrangement in a two-phase diluent system in the presence of free oxygen, a suitable surfactant, and a catalyst system comprising palladium, copper, and an alkali or alkaline earth metal chloride.Type: GrantFiled: July 14, 1978Date of Patent: September 2, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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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
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Patent number: 4212988Abstract: 2,5-Diketogluconic acid, alkyl esters or salts thereof, are reduced by an amine-borane to 2-ketogulonic acid, an intermediate for the preparation of ascorbic acid.Type: GrantFiled: March 26, 1979Date of Patent: July 15, 1980Assignee: Pfizer Inc.Inventor: Glenn C. Andrews
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4197245Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4182727Abstract: Sulfo- and aminosulfonyl-substituted aryloxyalkyl diketones, useful as anti-viral agents, are prepared, respectively, by reacting a phenoxyalkyl diketone with sulfuric acid; or by reacting a haloalkyl diketone with an alkali metal salt of a hydroxybenzenesulfonamide.Type: GrantFiled: June 7, 1978Date of Patent: January 8, 1980Assignee: Sterling Drug Inc.Inventors: Joseph C. Collins, Guy D. Diana
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Patent number: 4172839Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 30, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4159990Abstract: The novel stereoselective and regioselective alkali metal borohydride reduction of 2,5-diketogluconic acid, alkyl esters or salts thereof to form 2-ketogulonic acid together with lesser amounts of 2-ketogluconic acid is disclosed. The 2-ketogulonic acid is readily converted to ascorbic acid.Type: GrantFiled: October 20, 1977Date of Patent: July 3, 1979Assignee: Pfizer Inc.Inventor: Glenn C. Andrews
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Patent number: RE30530Abstract: Novel polymerizable monomers which are ethylenically unsaturated esters of the formula: ##STR1## wherein R.sub.4 comprises a polymerizable ethylenic double bond. Homopolymers and copolymers of the monomers are disclosed and in one embodiment provide water-dispersible film-forming polymer which may be electrophoretically deposited on a conducting substrate.Type: GrantFiled: August 25, 1978Date of Patent: February 24, 1981Assignee: Dulux Australia Ltd.Inventor: John J. Hopwood