Halogen In Acid Moiety Patents (Class 560/192)
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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: 4282373Abstract: Compounds of the formula (II): ##STR1## wherein X is halogen, hydroxyl or functionalized hydroxyl; Y is halogen, hydroxyl or alkoxy; R.sup.1 is a carboxylic acid group and ester thereof and amide derivative thereof or cyano; and R.sup.2 is hydrogen, a hydrocarbon, a heterocycle, a carboxylic acid group, a carboxylic acid ester, a carboxylic acid amide derivative, acyl, cyano, isocyano or an optionally substituted imine of the formula --CH.dbd.NZ or --N.dbd.CH.sub.2 wherein Z is hydrogen, alkyl, aryl, sulphonyl, --SR.sup.a, sulphoxide --SR.sup.a, or sulphonate --SR.sup.a wherein R.sup.a is alkyl of 1 to 6 carbon atoms or aryl, are useful as intermediates for the ultimate production of penicillins or cephalosporins.Type: GrantFiled: May 7, 1979Date of Patent: August 4, 1981Assignee: Beecham Group LimitedInventors: Angela W. Guest, Andrew W. Taylor, Robert Ramage
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Chlorinated derivatives of butyric acid as useful lubricant additives and lubricants containing same
Patent number: 4263157Abstract: Compounds of the general formula I ##STR1## in which R.sub.1 is chlorine or --CH.sub.2 --CCl.sub.3, andR.sub.2 is --N(R.sub.3)R.sub.4, --OH.N(R.sub.3)(R.sub.4)R.sub.5 or --OR.sub.6,R.sub.3 is C.sub.1 -C.sub.24 alkyl which can be interrupted once or several times by oxygen,R.sub.4 and R.sub.5 independently of one another are hydrogen or C.sub.1 -C.sub.24 alkyl, with R.sub.3 and R.sub.4 together having at least 8 C atoms,R.sub.6 is C.sub.8 -C.sub.20 alkyl, phenyl or C.sub.7 -C.sub.15 alkylphenyl, a group of the formula --(A)R.sub.7 or --CH.sub.2 CH.sub.2 --N(R.sub.10)--CH.sub.2 CH.sub.2 --O--C(O)--CH(R.sub.1)CH.sub.2 CCl.sub.3, whereinR.sub.7 is a radical of the formula --(R.sub.8)C(R.sub.9)--O--C(O)--CH(R.sub.1)--CH.sub.2 --CCl.sub.3, whereinR.sub.8 and R.sub.9 independently of one another are hydrogen, methyl or ethyl, and R.sub.1 has the meaning defined above,A is a C.sub.1 -C.sub.7 alkylene group which is unsubstituted or substituted by one or two radicals R.sub.Type: GrantFiled: April 18, 1979Date of Patent: April 21, 1981Assignee: Ciba-Geigy CorporationInventors: Eginhard Steiner, Andreas Schmidt -
Patent number: 4257975Abstract: A compound of the formula: ##STR1## wherein X and Y are independently selected from cyano and alkoxycarbonyl containing from 1 to 4 carbon atoms in the alkoxy group, and Q, R and Z are independently selected from chlorine and bromine provided that Q is always bromine when either Z or R is bromine. The compounds are useful as chemical intermediates.Type: GrantFiled: September 25, 1979Date of Patent: March 24, 1981Assignee: Imperial Chemical Industries LimitedInventor: Nazim Punja
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Patent number: 4258202Abstract: Cyclopropanecarboxylic acids and esters are disclosed, having the formula: ##STR1## wherein A=CF.sub.3 --C.tbd.C--; ##STR2## X=H, F, Cl, Br; Y=Cl, Br; R=H, alkyl C.sub.1 -C.sub.4Compounds of formula I are intermediates for the preparation of insecticide compounds of the pyrethroid type.Type: GrantFiled: February 26, 1979Date of Patent: March 24, 1981Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Francesco Corda, Franco Gozzo, Augusto Menconi
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Patent number: 4252976Abstract: A process for the preparation of 3-substituted thiophenes which involves cyclization of a novel intermediate, avoids the use of previously employed expensive starting materials. The thiophenes are useful for the preparation of penicillins and cephalosporins.The process is for the preparation of a thiophene of formula (I): ##STR1## where R.sup.1 represents a carboxylic acid group, or an ester or amide thereof or a nitrile group; R.sup.2 represents a group suitable for use as an .alpha.-substituent in the side-chain of a penicillin or cephalosporin; which comprises treating a compound of formula (II): ##STR2## wherein X represents halogen or optionally functionalized hydroxyl, Y represents halogen, hydroxyl, or alkoxy; with a source of nucleophilic sulphur under basic conditions.Type: GrantFiled: July 21, 1978Date of Patent: February 24, 1981Assignee: Beecham Group LimitedInventors: Angela W. Guest, Andrew W. Taylor, Robert Ramage
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Patent number: 4247713Abstract: Alkyl perfluoro-.omega.-fluoroformyl esters are provided which have the formula: ##STR1## wherein R is alkyl of 1-6 carbon atoms, andn is 0-6 (preferably 0).compounds where n is 0 are prepared by contacting SO.sub.3 with a compound of the formula ROOC--CF.sub.2 --CF.sub.2 --OR.sup.1. Compounds where n is 1-6 are prepared by contacting a compound where n is 0 with hexafluoropropylene oxide.Type: GrantFiled: August 17, 1978Date of Patent: January 27, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: David C. England
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Patent number: 4221916Abstract: Saturated vicinal esters produced by reacting olefins with carboxylic acid and anhydrides thereof in the presence of oxygen and a vanadium- or ruthenium-containing catalyst.Type: GrantFiled: August 25, 1978Date of Patent: September 9, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4221917Abstract: Monoolefins and diolefins are converted to corresponding esters in a process by contacting together at least one monoolefin, diolefin or mixture thereof, oxygen, at least one iodosoaryl dicarboxylate and at least one carboxylic acid, carboxylic acid anhydride or mixture thereof.Type: GrantFiled: March 3, 1978Date of Patent: September 9, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4215044Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.Type: GrantFiled: April 23, 1979Date of Patent: July 29, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: William J. Middleton
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Patent number: 4214096Abstract: Novel isothiouronium salts are herein described which correspond to the formula ##STR1## wherein R and R' are each independently hydrocarbyl or inertly-substituted hydrocarbyl of at least 4 carbon atoms; R.sub.1 -R.sub.4 are each independently alkyl or hydroxyalkyl of 1 to 4 carbon atoms, or R.sub.1 and R.sub.3 are joined to form a 5- or 6-membered heterocyclic ring; n is 0 or 1; and A.sup..crclbar. is an inert neutralizing anion. The isothiouronium salts are surprisingly effective dispersing agents and are used in forming electrodepositable latexes.Type: GrantFiled: June 15, 1979Date of Patent: July 22, 1980Assignee: The Dow Chemical CompanyInventors: Thomas C. Klingler, Ritchie A. Wessling, Dale S. Gibbs
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Patent number: 4201876Abstract: A fluorinated polyether is synthesized by (1) reacting perfluoroglutryl chloride and 1,5-hexafluoropentane diol to provide a fluorinated polyester and (2) converting ester groups of the polyester to ether groups by SF.sub.4 reduction. The product obtained is a thermally stable polyether which is particularly useful in providing an elastomeric material for aircraft fuel tank sealants, tire valves, O-rings, hose, gaskets, and the like.Type: GrantFiled: December 8, 1976Date of Patent: May 6, 1980Assignee: The United States of America as represented by the Secretary of the Air ForceInventor: Warren R. Griffin
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Patent number: 4180676Abstract: A catalyst comprising a uranium compound, an alkali metal ion, and a halide, is effective to convert conjugated dienes in carboxylic acid media to diacyloxy olefins.Type: GrantFiled: August 25, 1977Date of Patent: December 25, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4172208Abstract: The compound of the formula: ##STR1## is useful as an intermediate to prepare a compound having the generic formula ##STR2## wherein X is selected from groups to provide tetrahydropyran type compounds, 1,4 dioxane type compounds or tetrahydrofuran type compounds, and R is selected from the group consisting of alkali metal, NH.sub.4.sup.+, NH(CH.sub.2 CH.sub.2 OH).sub.3.sup.+, and lower alkyl, branched or straight chain, with up to about C.sub.20 in the chain, useful as a detergent builder.Type: GrantFiled: July 27, 1978Date of Patent: October 23, 1979Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Kent P. Lannert
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Patent number: 4164615Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.Type: GrantFiled: August 25, 1977Date of Patent: August 14, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4162363Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.Type: GrantFiled: August 25, 1977Date of Patent: July 24, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4159388Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion sequestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.Type: GrantFiled: May 15, 1978Date of Patent: June 26, 1979Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4154753Abstract: Surface-active products containing a highly fluorinated aliphatic substituent are prepared by nucleophilic attack of an oligomer of tetrafluoroethylene with an organic hydroxy compound in association with a proton acceptor.Type: GrantFiled: January 3, 1972Date of Patent: May 15, 1979Assignee: Imperial Chemical Industries LimitedInventor: Harold C. Fielding
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Patent number: 4127731Abstract: A fluorinated acyl fluoride having an ester group which has the formulaFOC(CF.sub.2).sub.n-1 CO.sub.2 Rwherein n is 2 to 4 and R represents an alcohol residual group is produced by reacting a perfluorolactone having the formula ##STR1## wherein n represents an integer of 2 to 4, with an alcohol having the formulaROHwherein R represents an alcohol residual group.Type: GrantFiled: November 8, 1976Date of Patent: November 28, 1978Assignee: Asahi Glass Company Ltd.Inventors: Masaaki Yamabe, Seiji Munekata, Yoshio Sugaya, Yukio Jitsugiri
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Patent number: 4123459Abstract: Novel methods for preparing polycarboxylic compounds which are useful as metal sequestrants and food acidulants are disclosed. These compounds are aconitic and a mixture of aconitic acid, and the lactones of isocitric acid and alloisocitric acid. The compounds can be neutralized to the corresponding salts which, in turn, are metal sequestering agents. The novel methods include chlorination of propane-1,1,2,3-tetracarboxyalic tetraesters.Type: GrantFiled: December 22, 1975Date of Patent: October 31, 1978Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4123458Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion seqestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.Type: GrantFiled: December 22, 1975Date of Patent: October 31, 1978Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4103025Abstract: Pharmaceutically active compounds of the formula ##STR1## wherein --OR.sub.1, --OR.sub.2, --OR.sub.3 and --OR.sub.4, which may be the same or different, each represents a free or esterified hydroxyl group and --COOR.sub.5 represents a free or esterified carboxyl group, are provided together with processes for their production and pharmaceutical compositions containing them. Compounds of formula II and III possess valuable cicatrizing and anti-inflammatory properties.Type: GrantFiled: March 17, 1977Date of Patent: July 25, 1978Assignee: Inverni Della Beffa S.p.A.Inventor: Giuseppe Mustich
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Patent number: 4097678Abstract: 3.alpha.-Hydroxy and 3.alpha.-acyloxy- .DELTA..sup.9(11) -5.alpha.-D-homo-20-ketopregnenes of the formula ##STR1## wherein R is hydrogen or acyl, R.sub.1 is hydrogen or methyl and R.sub.2 is methyl or ethyl, are produced by esterifying a corresponding 3.beta.-hydroxy-5.alpha.-20-keto pregnane of the formula ##STR2## wherein R.sub.1 and R.sub.2 have the values given above, with m-iodo-benzoic acid with inversion of the 3.beta.-oxy group to a 3.alpha.-oxy group; chlorinating the thus-produced 3.alpha.-m-iodobenzoyl ester with dichloroiodobenzene under irradiation; and treating the reaction product with a dehydrohalogenating silver salt. Optionally thereafter, the 3.alpha.-iodobenzoyl group is split off in a conventional manner to produce the corresponding 3.alpha.-hydroxy steroid and optionally the thus-produced 3.alpha.-hydroxy steroid is esterified to produce a desired 3-ester thereof.Type: GrantFiled: June 8, 1976Date of Patent: June 27, 1978Assignee: Schering AktiengesellschaftInventors: Ulrich Kerb, Rudolf Wiechert, Otto Engelfried
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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: 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: 4064185Abstract: Compositions are provided as well as methods for preparing the compositions which serve as cyclization precursors for the preparation of C-11 alkenyl substituted steroids and nor-steroids. The alkenyl group may be converted after cyclization to a variety of heterosubstituents to provide heterofunctionalized C-11 steroids and nor-steroids. The compounds are provided having an initiator group, which has a chalcoxy atom in juxtaposition to a double bond, an olefinically unsaturated linking group and a terminating group which acts to from a carbocation which reacts with a nucleophile to provide a stable product. The C-11 substituent is found to provide upon cyclization the alpha-configuration, so that the subject compounds provide a direct route to the difficultly accessible alpha-C-11 substituted steroids, or, if desired, the alpha-configuration can be inverted to the beta-configuration.Type: GrantFiled: April 28, 1975Date of Patent: December 20, 1977Assignee: The Board of Trustees of Leland Stanford Junior UniversityInventors: William S. Johnson, Grant E. Dubois
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Patent number: 4057578Abstract: Adducts of trichloromethane phosphonic dichloride and olefinically unsaturated compounds having the general ##STR1## WHEREIN Q designates: A. (C R"R'" -- C R R').sub.nwherein R and R', which may be the same or different, each designatesH, alkyl or flourine;R" designates H, alkyl, aryl, substituted aryl, fluorine, chlorine, bromine, cyano, carbalkoxy, carboxy, acyloxy-methylene, acyloxy propylene, acetoxy, alkoxy, sulfonyl-alkyl or sulfonyl-aryl and R'" designates H, alkyl, fluorine, chlorine or bromine, or R and R" form together a ring system, and n is an integer of from 1 to about 500;B. (CH.sub.2 CR.sup.IV .dbd. CR.sup.V CH.sub.2).sub.mwherein R.sup.IV and R.sup.V, which may be the same or different, each designates hydrogen, methyl or chlorine, and m is an integer of from 1 to about 200.Type: GrantFiled: April 12, 1976Date of Patent: November 8, 1977Assignee: Rhone-ProgilInventors: Meir Asscher, Hadassa Rosin
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Patent number: 4057579Abstract: Adducts of trichloromethane phosphonic dichloride and olefinically unsaturated compounds having the general formula ##STR1## WHEREIN Q designates: A. (C R"R'"--C R R').sub.nwherein R and R', which may be the same or different, each designatesH, alkyl or flourine;R" designates H, alkyl, aryl, substituted aryl, fluorine, chlorine, bromine, cyano, carbalkoxy, carboxy, acyloxy-methylene, acyloxy propylene, acetoxy, alkoxy, sulfonyl-alkyl or sulfonyl-aryl and R'" designates H, alkyl, fluorine, chlorine or bromine, or R and R" form together a ring system, and n is an integer of from 1 to about 500;B. (CH.sub.2 CR.sup.IV .dbd. CR.sup.V CH.sub.2).sub.mwherein R.sup.IV and R.sup.V, which may be the same or different, each designates hydrogen, methyl or chlorine, and m is an integer of from 1 to about 200.Type: GrantFiled: December 4, 1974Date of Patent: November 8, 1977Assignee: Rhone-ProgilInventors: Meir Asscher, Hadassa Rosin