Patents Examined by Lorraine A. Weinberger
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Patent number: 4001319Abstract: Compounds containing carboxylic acid fluoride or chloride groups react with sulfur trioxide at temperatures between -30.degree. to about 100.degree. C to give carbonyl fluoro- or chlorosulfates. Preferred reactants are polyfluoroalkyl or polyfluoroalkenyl carbacyl acid fluorides. The carbacyl halosulfates are useful as cationic polymerization catalysts and as chemical intermediates.FIELD OF THE INVENTIONThis invention relates to a method of making carbacyl halosulfates.THE PRIOR ARTCertain perhalocarbacyl fluorosulfates, ##EQU1## are known, as shown in the following tabulation.______________________________________ Reference R.sub.f ______________________________________ 1. Des Marteau and Cady, Inorg. Trifluoromethyl Chem. 5, 169 (1966); Chem. Chlorodifluoromethyl Abs. 64, 8020 (1966) Pentafluoroethyl Heptafluoropropyl 2-(Fluorosulfonyloxy)- tetrafluoroethyl 2. Delfino and Shreeve, Inorg. Trifluoromethyl Chem. 5, 308 (1966); Chem. Abs. 64, 12544 (1966) 3. Fox & Franz, Inorg. Chem. Fluoro 5, 946 (1966); Chem.Type: GrantFiled: May 7, 1973Date of Patent: January 4, 1977Assignee: E. I. Du Pont de Nemours and CompanyInventors: David C. England, Carl G. Krespan
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Patent number: 4001229Abstract: Triphenylethylenes having an N-(dialkylaminoalkyl)alkanesulfonamide substituent in the one of the phenyl rings may be prepared from similarly substituted benzophenones by reaction thereof with a benzyl Grignard reagent followed by dehydration of the resulting triphenylethanol intermediate and if desired chlorination or nitration of the resulting product. The triphenylethylenes have estrogenic and post-coital antifertility action and are useful as intermediates for the preparation of other triphenylethylene compounds.Type: GrantFiled: April 4, 1974Date of Patent: January 4, 1977Assignee: Mead Johnson & CompanyInventor: William E. Kreighbaum
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Patent number: 3998868Abstract: A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy or phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH=CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.Type: GrantFiled: August 14, 1975Date of Patent: December 21, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Mizutani, Nobushige Itaya, Nobuo Ohno, Takashi Matsuo, Shigeyoshi Kitamura, Yositosi Okuno
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Patent number: 3996272Abstract: This invention relates to a chemical process for preparing pentachloro-2-propanone (pentachloroacetone) and dichloroacetic acid from isopropyl ethers which may be partially chlorinated. The pentachloroacetone process is carried out by reacting the isopropyl ethers with chlorine in the presence of water to produce pentachloroacetone which can then be recovered. Alternatively, if dichloroacetic acid is desired, the pentachloroacetone process may be carried further by reacting the pentachloroacetone with a base-acting material to produce a salt of dichloroacetic acid and then reacting this salt with acid to produce dichloroacetic acid of about 95% purity.Type: GrantFiled: October 3, 1974Date of Patent: December 7, 1976Assignee: The Dow Chemical CompanyInventors: Joanne D. Burger, William L. Howard
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Patent number: 3994925Abstract: Salts of polyhydroxyphenylchromanones, e.g., silymarin or one or more members of the silymarin group, are reacted with a monoaminopolyhydroxy alcohol of the formula ##EQU1## wherein X IS AN INTEGER FROM 3 TO 5; ANDR.sub.1 and R.sub.2 are hydrogen, lower alkyl or hydroxyalkylTo give chemotherapeutic salt compounds which are water soluble while retaining a high degree of medical effectiveness. The salt compounds can be administered to mammals to antagonize or mitigate liver damage and inflammation.Type: GrantFiled: January 21, 1974Date of Patent: November 30, 1976Assignee: Dr. Madaus & Co.Inventors: Rolf Hermann Heinrich Madaus, Gunter Halbach, Wilfried Trost
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Patent number: 3994953Abstract: The present invention is concerned with a method for preparing grandisol, the major component of the boll weevil sex pheromone. This method involves the conversion of 4-chloro-2-butanone to 5-chloro-3-methyl-1-penten-3-ol, acid-catalyzed isomerization of the latter compound to E- and Z-5-chloro-3-methyl-2-penten-1-ol, followed by conversion to ethyl 3-[2-chloroethyl]-3-methyl-4-pentenoate by treatment with triethyl orthoacetate, cyclization of ethyl 3-[2-chloroethyl]-3-methyl-4-pentenoate to ethyl Z- and E-2-vinyl-2-methylcyclobutanecarboxylate by reaction with base, conversion of ethyl Z- and E-2-vinyl-2-methylcyclobutanecarboxylate to Z- and E-2-[2-methyl-2-vinylcyclobutyl]-2-propanol by reaction with methyllithium, and the conversion of the latter compound to grandisol by reaction with diborane and basic hydrogen peroxide followed by dehydration.Type: GrantFiled: October 25, 1974Date of Patent: November 30, 1976Inventor: James H. Babler
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Patent number: 3993684Abstract: Photosensitive homopolymers and substantially non-crosslinked copolymers containing the recurring unit: ##EQU1## R.sub.1 may be substituted or unsubstituted alkylene, aralkylene, alkoxyalkylene or aryloxyalkylene. R.sub.2 is a substituted or unsubstituted aryl group or heterocyclic group having aromatic character. R.sub.3, R.sub.4, and R.sub.5 are hydrogen, halogen or lower alkyl. R.sub.6 and R.sub.7 may be hydrogen, halogen, nitro, lower alkyl, phenyl, substituted phenyl, phenoxy and lower alkoxy. Lithographic plates bearing these photosensitive polymers can be stored without deterioration for extended periods prior to exposure, and produce highly abrasion resistant plates on being exposed. The photosensitive polymers of the invention are preferably produced by homopolymerization of novel monomers having the general formula ##EQU2## where R.sub.1 .sub.' is alkylene, haloalkylene, alkoxyalkylene, aminoalkylene, cycloalkylene, aralkylene, cycloalkylalkylene, cyanoalkylene, and aryloxyalkylene, and R.sub.2, R.Type: GrantFiled: August 3, 1973Date of Patent: November 23, 1976Assignee: Western Litho Plate & Supply Co.Inventors: William R. Dunnavant, Edward M. Harris, Philip F. Kurz, Richard A. Markle, Edward H. Parker
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Patent number: 3989742Abstract: The copper and palladium ethylene-oxidation catalyst used in the preparation of vinyl acetate is regenerated in a process including deposition of the metals from solution in a Daniell-type galvanic cell and subsequent reconversion to the halides.Type: GrantFiled: October 1, 1969Date of Patent: November 2, 1976Assignee: Societa' Italiana Resine S.I.R. S.p.A.Inventors: Benedetto Calcagno, Claudio Divo, Marcello Ghirga
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Patent number: 3988328Abstract: The present invention concerns novel 2-dialkylamino propane derivatives of the formula: ##EQU1## wherein either, R.sub.1 and R.sub.2 are each alkyl; R.sub.3 is hydrogen or alkyl; Q is --OM, wherein M is hydrogen or a cation, --OR.sub.4, wherein R.sub.4 is alkyl or unsubstituted or substituted phenyl or --NR.sub.5 R.sub.6, wherein R.sub.5 is hydrogen, alkyl or unsubstituted or substituted phenyl and R.sub.6, independently has one of the significances of R.sub.5 or is --NHR.sub.7, wherein R.sub.7 is hydrogen and n is an integer 1, 2 or 3, in free base or acid addition salt form.The compounds possess plant growth regulating and herbicidal properties and are accordingly useful in agriculture.Type: GrantFiled: August 20, 1974Date of Patent: October 26, 1976Assignee: Sandoz Ltd.Inventor: Rupert Schneider
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Patent number: 3988373Abstract: A quaternary ammonium salt of the formula: ##SPC1## ##EQU1## wherein A is a lower alkylene, a lower alkenylene or a lower alkadienylene; R.sub.1 and R.sub.2 are each lower alkyl which may be linked together directly or by an oxygen atom to form a saturated heterocyclic group; R.sub.3 is a lower alkyl, a halo (lower) alkyl, a lower alkynyl, phenyl (lower) alkyl which may have one or more halogen atoms as substituents on the phenyl ring, a lower alkenyl, a hydroxy (lower) alkyl, a carboxy (lower) alkyl or a lower alkenyloxycarbonyl (lower) alkyl; R.sub.4, R.sub.5 and R.sub.6 are each lower alkyl having 1 to 3 carbon atoms; X is an acid residue; and wherein the cyclohexyl ring may have one double bond, with the proviso that when the cyclohexyl ring has one double bond in the 1,2 position, A may not be ##EQU2## when X.sup.- is iodide, R.sub.4, R.sub.5 and R.sub.6 are all methyl; R.sub.1, R.sub.2 and R.sub.3 are all methyl or all ethyl, or R.sub.1 is methyl, R.sub.2 is ethyl and R.sub.Type: GrantFiled: September 16, 1974Date of Patent: October 26, 1976Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Kazuo Nakanishi, Takashi Iwata, Hisae Haruta, Kazuhiko Yoshida, Hideo Yagi, Akira Hashimoto nee Matui
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Patent number: 3987061Abstract: Macrocyclic polyether "crown" compounds of the formula ##EQU1## WHEREIN T is a C.sub.2 -C.sub.3 alkylene, A is ##EQU2## R being H or C.sub.1 -C.sub.18 alkyl, R.sup.2 and R.sup.3 being independently C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.4 alkenyl, or C.sub.6 -C.sub.14 aryl; Q and Z are independently 1,2-arylene (or saturated derivatives thereof) or substituted 1,2-arylene (or saturated derivatives thereof); a is 0, 1, 2, or 3; b is an integer from 3 to 20; y is 1 or zero; x.sub.1, x.sub.2, x.sub.3, and x.sub.4 are integers independently selected to give a 15-60 atom ring. Such crown compounds are generally useful in the formation of complexes with ionic metal compounds, thus making it possible to use certain chemical reagents in media wherein they are normally insoluble.Type: GrantFiled: February 15, 1974Date of Patent: October 19, 1976Assignee: E. I. Du Pont de Nemours and CompanyInventor: Charles J. Pedersen
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Patent number: 3987094Abstract: Process for preparing carboxylic acids by (1) reacting a glycidonitrile with a carboxylic acid halide in the presence of a catalytic amount of a tertiary amine or acid salt thereof to form a 2-acyloxy-3-halo-propionitrile, (2) dehydrohalogenating the halogenated acylate from step (1) to form the acyloxy acrylonitrile intermediate (enol-acylate) (3) hydrolyzing the enol-acylate from step (2) with aqueous base to form the carboxylic acid salt, and (4) acidifying the carboxylic acid salt with acid to form the carboxylic acid. Salts of persulfate and hypochlorite ions can be added to destroy cyanide ion. The process can be used to prepare a wide variety of carboxylic acids, e.g., 2-(4'-isobutylphenyl)propionic acid, now known generally as ibuprofen, a highly active anti-inflammatory drug.Type: GrantFiled: December 10, 1974Date of Patent: October 19, 1976Assignee: The Upjohn CompanyInventor: David R. White
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Patent number: 3985800Abstract: Production of acrylic acid by reacting acrolein with molecular oxygen in the presence of steam and, if desired, inert gases at elevated temperature in contact with a fixed bed of cobalt molybdate catalyst prepared by precipitating cobalt molybdate from the combined aqueous solutions of a cobalt salt, of a molybdenum compound and of ammonia at a temperature of about 60.degree.C and at a pH of at most 7; filtering off, washing and drying the precipitate at a temperature of at least 100.degree.C; heating the dry cobalt molybdate for several hours at elevated temperatures, grinding and transforming it into shapes; and sintering the cobalt molybdate shapes for several hours. The acrylic acid is more particularly produced in contact with a catalyst prepared by combining the aqueous solution of the cobalt salt with that of the molybdenum compound in the atomic ratio of Co:Mo of about 1.05:1; establishing in the combined solutions a pH between 3.8 and 6.0; drying the precipitate at 110.degree.-170.degree.Type: GrantFiled: August 31, 1973Date of Patent: October 12, 1976Assignee: Hoechst AktiengesellschaftInventors: Heinz Erpenbach, Klaus Gehrmann, Winfried Lork, Peter Prinz
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Patent number: 3985743Abstract: Thiocarbamylsulfenamides are prepared by the reaction of an amine and monohaloamine with carbon disulfide in the presence of a base. The compounds have particular utility as accelerators in the vulcanization of unsaturated polymers.Type: GrantFiled: November 25, 1974Date of Patent: October 12, 1976Assignee: The B. F. Goodrich CompanyInventor: Ray D. Taylor
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Patent number: 3985795Abstract: Glycol esters of an olefin are prepared by contacting an olefin and a molecular oxygen containing gas in a carboxylic acid medium in the presence of a catalyst. Selectivities to the desired glycol esters are improved by treating the viscous residue and the precursor light components separated from the oxidation effluent by contacting them with water. In a preferred embodiment both residue and precursor light components streams are fed to the same zone wherein they are converted to additional glycol.Type: GrantFiled: December 30, 1974Date of Patent: October 12, 1976Assignee: Halcon International, Inc.Inventor: John Kollar
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Patent number: 3985794Abstract: Palladium and copper ethylene-oxidation catalysts, used in production of vinyl acetate, are regenerated by a process including electrolytic deposition of the metals and subsequent reconversion to halides.Type: GrantFiled: October 1, 1969Date of Patent: October 12, 1976Assignee: Societa' Italiana Resine S.I.R. S.p.A.Inventors: Benedetto Calcagno, Claudio Divo, Marcello Ghirga
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Patent number: 3984409Abstract: Compounds of the formulae: ##SPC1##And ##SPC2##And the salts thereof with pharmaceutically acceptable cations wherein n and m are each two or three; X is oxygen or sulphur; R.sup.2 and R.sup.3, when taken separately, are each hydrogen or alkyl having 1 to 4 carbon atoms; R.sup.2 and R.sup.3, when taken together, are alkylene having 2 to 4 carbon atoms; Y is methylene or a single bond; R.sup.4 and R.sup.5, when taken separately, are each hydrogen, hydroxy or alkoxy having 1 to 5 carbon atoms, and R.sup.4 and R.sup.5, when taken together, are oxo or alkylene dioxy having 2 to 4 carbon atoms, each oxygen atom in R.sup.4 and R.sup.5, when taken separately, and in R.sup.4 and R.sup.5, when taken together, being separated from the nitrogen atom of the heterocyclic ring by two or more carbon atoms, said compounds being cerebral vasodilators.Type: GrantFiled: October 4, 1974Date of Patent: October 5, 1976Assignee: Pfizer Inc.Inventor: Gerald F. Holland
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Patent number: 3984462Abstract: A process for producing dodecanedioic acid dimethyl ester comprising the steps of reacting cyclohexanone with methanol and hydrogen peroxide in the presence of an acid catalyst and water at a temperature below the boiling point of the methanol to produce methoxycyclohexyl peroxide, said methanol and hydrogen peroxide being used in an amount of about 15 to about 36 moles and in an amount of about 0.5 to about 1.5 moles per mole of the cyclohexanone respectively, dimerizing the resulting methoxycyclohexyl peroxide as it is contained in the reaction mixture in the presence of a ferrous salt and at least about 25 moles of methanol per mole of the starting cyclohexanone to produce dodecanedioic acid dimethyl ester, and separating the resulting dodecanedioic acid dimethyl ester from the reaction mixture.Type: GrantFiled: December 20, 1974Date of Patent: October 5, 1976Assignee: Okamura Oil Mill LimitedInventors: Shigeru Tsutsumi, Yoshishige Kida
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Patent number: 3983159Abstract: The oxidative coupling of benzenecarboxylic acid esters to form the corresponding biphenylpolycarboxylic acid esters, comprising contacting a benzenecarboxylic acid ester having at least one hydrogen atom bonded to the nuclear carbon atom of the benzene ring, such as methyl benzeate, with molecular oxygen in a liquid phase using a catalyst comprising at least one compound selected from organic carboxylates of palladium, such as palladium acetate and .beta.-dikete complexes of palladium, such as acetylacetone-palladium complex. Use of at least one zirconium compound, such as zirconium oxystearate in conjunction with the catalyst gives rise to an increased catalytic activity.Type: GrantFiled: August 16, 1974Date of Patent: September 28, 1976Assignee: Teijin LimitedInventors: Yataro Ichikawa, Teizo Yamaji
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Patent number: 3981908Abstract: An improved process for preparing glycol esters by reacting an olefin with oxygen in the presence of a carboxylic acid or an inert medium containing a carboxylic acid is described in which the improvement comprises carrying out the reaction in the presence of a composite catalyst composed of or containing A. a compound of boron, aluminum, silicon, phosphorus or a combination thereof, and B. a compound of iron, copper or a combination thereof.Type: GrantFiled: September 30, 1974Date of Patent: September 21, 1976Assignee: Rohm GmbHInventors: Wolfgang Ganzler, Klaus Kabs, Gunter Schroeder