Halogen In Acid Moiety Patents (Class 560/219)
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Patent number: 5025003Abstract: Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthetis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents, are provided which have the structure ##STR1## wherein R.sup.2 is a metal ion, lower alkyl or H; R.sup.3 is a metal ion or lower alkyl;R is R.sup.1 --(CH.sub.2).sub.n --, R.sup.1 --(CH.sub.2).sub.m --O-- orR.sup.1 --(CH.sub.2).sub.m --OCH.sub.2 --, wherein n is 1 to 4 and m is 0 to 3, andR.sup.1 is R.sup.5 --Q.sup.1 --Q.sup.2 --Q.sup.3 -- wherein R.sup.5, Q.sup.1, Q.sup.2 and Q.sup.3 are as defined herein.New intermediates, new methods of preparation and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.Type: GrantFiled: September 18, 1989Date of Patent: June 18, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Scott A. Biller
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Patent number: 5023380Abstract: Compounds have a structure represented by Formula I:CF.sub.2 =CF-X-R-(X-CF=CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF=CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH).sub.m ;wherein X, R and m are as defined for Formula I;(b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z-CF.sub.2 CF.sub.2 -X-R-(X-CF.sub.2 CF.sub.2 - Z).sub.Type: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: The Dow Chemical CompanyInventors: David A. Babb, Bobby R. Ezzell, Katherine S. Clement
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Patent number: 4980501Abstract: A process for the production of secondary-butyl perfluoroester is provided by reacting ethylene with a perfluorocarboxylic acid in the presence of oxygen.Type: GrantFiled: March 19, 1990Date of Patent: December 25, 1990Assignee: National Distillers and Chemical CorporationInventor: John A. Scheben
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Patent number: 4943653Abstract: A novel fluorine-containing acrylic acid derivative of the invention is represented by the formula:(CH.sub.2 .dbd.CF--CO).sub.p--A (I)wherein A is a residue derived from an organic compound having at least two active hydrogen atoms derived by removing at least two active hydrogen atoms, and p is an integer corresponding to the valency of the residue A, which is easily cured.Type: GrantFiled: February 26, 1987Date of Patent: July 24, 1990Assignee: Daikin Industries Ltd.Inventors: Shigeru Morita, Masahiko Oka
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Patent number: 4940813Abstract: A process is described for the preparation of an optically active carboxylic acid or ester derivative thereof from a ketene and an optically active .alpha.-hydroxyester or an .alpha.-hydroxy amide.Type: GrantFiled: March 31, 1989Date of Patent: July 10, 1990Assignee: Merck & Co., Inc.Inventors: Edward G. Corley, Robert D. Larsen, Edward J. J. Grabowski, Paul Reider
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Patent number: 4910330Abstract: Hydroxy sulfonic acids in general and isethionic acid (2-hydroxy ethyl sulfonic acid) in particular can be prepared at 99+% purity and good yields by the selective oxidation of a precursor hydroxy mercaptan with hydrogen peroxide. The resulting product is pure enough to be used directly in the synthesis of sulfo-acrylic esters which are finding considerable use as stabilizers in producing vinylidene chloride copolymers used for FDA approved packaging films.Type: GrantFiled: September 25, 1987Date of Patent: March 20, 1990Assignee: Union Oil Company of CaliforniaInventors: Dennis E. McGee, Ted S. Hallen
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Patent number: 4902835Abstract: New chemical reactions of 1,1,2-trifluoro-1,3-butadiene provide simple access to a series of new fluorinated alkene derivatives. These derivatives provide a simple, general methodology for the stereocontrolled preparation of 2-fluoro-2-alkenoate esters and related monofluoroalkene derivatives which include fluoro analogs of known insecticides, pheromones or pharmaceuticals. A new method for the preparation of 1,1,2-trifluoro-1,3-butadiene is also provided.Type: GrantFiled: January 11, 1988Date of Patent: February 20, 1990Assignee: The University of RochesterInventors: Andrew S. Kende, Noritada Matsuo
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Patent number: 4870188Abstract: Vinyl radiohalogenated small molecules as shown in formulas I and II: ##STR1## wherein *X is a radiohalogen, C.dbd.C is a double bonded set of sp.sup.2 hybridized carbon atoms, and substituents R.sub.1, R.sub.2, and Y are as defined below. R.sub.1 and R.sub.2 are substituents independently selected from among hydrogen; alkyl or substituted alkyl, provided that any sp.sup.2 or sp carbon atom substituted on the alkyl is separated from C.dbd.C by at least one fully substituted sp.sup.3 carbon atom; aryl or substituted aryl, provided that the aryl is bonded directly to C.dbd.C; heteroalkyl, provided, first, that no heteroatom of the heteroalkyl bonds directly to C.dbd.C and, second, that any sp.sup.2 or sp hybridized carbon bonded to a heteroatom of the heteroalkyl is not bonded directly to or otherwise conjugated with C.dbd.C and, third, that where a single sp.sup.3 carbon intervenes between C.dbd.C and an sp.sup.2 or sp carbon bonded to a heteroatom that intervening sp.sup.Type: GrantFiled: April 16, 1987Date of Patent: September 26, 1989Assignee: NeoRx CorporationInventors: Daniel S. Wilbur, Stephen W. Hadley
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Patent number: 4847401Abstract: The large scale preparation of ethyl 2,2-difluoro-4- pentenoate and 2-fluorinated methyl aminoacetonitriles by reaction of 2-H-perfluoroethyl allyl ether and n-butyl lithium and fluoromethylacetonitrile and a Grignard reagent, respectively, is largly unsuccessful because of side reactions which convert intermediate products and reactants to undesired products. Applicants have overcome these problems by performing the reactions with cooling in a continuous manner in a flow reactor with short residence time.Type: GrantFiled: January 15, 1988Date of Patent: July 11, 1989Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Michael Kolb
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Patent number: 4841005Abstract: A tricyclodecane derivative represented by formula (I): ##STR1## wherein R.sup.1 represents a group X.sup.1 O-- or a hydrogen atom;R.sup.2 represents a hydrogen atom when R.sup.1 represents a group X.sup.1 O--, or R.sup.2 represents a group X.sup.1 O-- when R.sup.1 represents a hydrogen atom;wherein X.sup.1 represents a group ##STR2## or a hydrogen atom, wherein X.sup.2 represents a hydrogen atom, a methyl group, or a trifluoromethyl group;R.sup.3 represents a fluoroalkyl group containing from 1 to 21 carbon atoms, an iodine atom, or a hydrogen atom; andR.sup.4 represents an iodine atom or a hydrogen atom when R.sup.3 represents a fluoroalkyl group containing from 1 to 21 carbon atoms, or R.sup.4 represents a fluoroalkyl group containing from 1 to 21 carbon atoms when R.sup.3 represents an iodine atom or a hydrogen atom.Type: GrantFiled: February 12, 1988Date of Patent: June 20, 1989Assignee: Daikin Industries, Ltd.Inventors: Sinji Tamaru, Motonobu Kubo
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Patent number: 4837357Abstract: 2,2-Disubstituted 3-chloropropionic esters I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl, aryl or C.sub.7 -C.sub.12 -aralkyl or R.sup.1 -C-R.sup.2 is 5-, 6- or 7-membered ring, R.sup.3 is C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl or C.sub.7 -C.sub.12 -aralkyl, are prepared by converting 2,2-disubstituted 3-hydroxypropanals II ##STR2## into the esterdiol III ##STR3## reacting this esterdiol III in the presence of a transesterification catalyst with an alcohol R.sup.3 OH to give the 3-hydroxyester IV ##STR4## reacting the hydroxyester IV with a stoichiometric or greater than stoichiometric amount of the thionyl chloride and thermally decomposing the product to give the chloropropionic ester I.Type: GrantFiled: October 21, 1987Date of Patent: June 6, 1989Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger
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Patent number: 4835305Abstract: A trifluoroacrylate has been prepared by reacting hexafluoropropene with halogen fluorosulfate (halogen X:Cl, Br or I), eliminating the fluorosulfate CF.sub.3 --CFX--CF.sub.2 --OSO.sub.2 F to give the acid fluoride CF.sub.3 --CFX--COF, esterifying the acid fluoride and dehalogenating the product using a metal component.Type: GrantFiled: April 13, 1988Date of Patent: May 30, 1989Assignee: Hoechst AktiengelselschaftInventors: Peter Blickle, Klaus Hintzer, Werner Schwertfeger, Dieter Ulmschneider
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Patent number: 4727181Abstract: Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.Type: GrantFiled: April 21, 1986Date of Patent: February 23, 1988Assignee: The Dow Chemical CompanyInventor: William J. Kruper, Jr.
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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
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Patent number: 4681953Abstract: Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a .gamma.-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.Type: GrantFiled: August 22, 1975Date of Patent: July 21, 1987Assignee: Sagami Chemical Research CenterInventors: Kiyoshi Kondo, Kiyohide Matsui, Akira Negishi, Yuriko Takahatake
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Patent number: 4634778Abstract: Process for preparing chlorinated ethylenic derivatives of the formula ##STR1## in which R.sub.1 represents acetyl, formyl optionally in the form of an acetal, hydroxy optionally as an ether or ester, alkyloxycarbonyl, alkyl of 1 to 12 carbon atoms substituted by one or more acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, alkenyl of 2 to 12 carbon atoms containing one or more double bonds optionally substituted by one or more of acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, or R.sub.1 represents 3-sulpholenyl or a radical of formula ##STR2## in which R.sub.2 denotes a hydrogen or acetyl, by reacting chlorine in a nonpolar aprotic solvent with a compound of general formula ##STR3## in which R.sub.1 is defined as above. The products of formula I, some of which are new, are useful as intermediates in the synthesis of terpene products such as vitamin E.Type: GrantFiled: November 16, 1984Date of Patent: January 6, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel, Pierre Chabardes
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Patent number: 4618703Abstract: Production of a reaction mixture comprising the multifunctional acrylates, methacrylates or halogenated derivatives thereof of oxyalkylated allyl alcohol characterized as being free of odor typical of allyl compounds, not lachrimatory and substantially reduced skin irritation as compared with acrylates and methacrylates of allyl alcohol. The acrylate and methacrylate compositions of the invention are useful as radiation-crosslinkable diluents for radiation-hardenable compositions (binders).Type: GrantFiled: September 13, 1985Date of Patent: October 21, 1986Assignee: Atlantic Richfield CompanyInventors: Chandrakant B. Thanawalla, David C. Dehm
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Patent number: 4599443Abstract: A compound of the formula ##STR1## where R.sub.1 is hydrogen, lower alkyl, alkaline earth metal or alkali metal; or magnesium halide salts thereof, useful as intermediates for unsaturated eicosanoic acids and derivatives thereof which inhibit the synthesis of SRS-A.Type: GrantFiled: October 31, 1984Date of Patent: July 8, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, George W. Holland, Perry Rosen
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Patent number: 4570018Abstract: A novel chemical, fluorochlorocyclopropane (I) of the following formula: ##STR1## is prepared by the addition of fluorochlorocarbene to the corresponding olefin (II) of the following formula:CH.sub.2 .dbd.CR.sup.1 -R.sup.2The compound is a useful intermediate for synthesizing some chemicals, e.g., some cephalosporins.(wherein R.sup.1 is hydrogen, halogen, 1 to 8C alkylamino, alkoxy, or alkylthio andR.sup.2 is halogen, 1 to 8C alkylamino, alkoxy, or alkylthio).Type: GrantFiled: May 16, 1984Date of Patent: February 11, 1986Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
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Patent number: 4558152Abstract: A copolymer of an acrylic acid derivative and an other copolymerizable monomer, the acrylic acid derivative being a compound represented by the formula (1) ##STR1## wherein Rf and Rf' are respectively perfluoroalkyl group having 3 to 21 carbon atoms, a is an integer of 2 to 10, b is an integer of 1 to 10. The said copolymers are useful as water repellent, oil repellent and stain proofing agents.Type: GrantFiled: April 24, 1985Date of Patent: December 10, 1985Assignee: Daikin Kogyo Company LimitedInventor: Shouji Iwatsuki
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Patent number: 4490560Abstract: Water-clear liquid polymers of epihalohydrin are obtained by passing said polymers or their solutions, that are yellow to dark brown, through a column of amorphous silica.Type: GrantFiled: September 29, 1982Date of Patent: December 25, 1984Assignee: The B. F. Goodrich CompanyInventors: Simon H. Yu, Daniel A. Versace
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Patent number: 4489210Abstract: The invention relates to a process for the halogenation of organic compounds in the liquid phase using gaseous halogenating agents, the gaseous halogenating agents being metered into the reaction vessel at such an entry velocity that a gas jet is formed in the reaction mixture at the point of entry of the halogenating agent and the formation of individual gas bubbles at the point of entry is prevented.Type: GrantFiled: July 30, 1982Date of Patent: December 18, 1984Assignee: Bayer AktiengesellschaftInventors: Helmut Judat, Ulrich Schnegg, Karlfried Wedemeyer
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Patent number: 4474806Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.Type: GrantFiled: May 10, 1982Date of Patent: October 2, 1984Assignee: Merck & Co., Inc.Inventors: Thomas R. Beattie, Shu S. Yang
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Patent number: 4468521Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: February 22, 1982Date of Patent: August 28, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Toshiaki, Nishida Takashi, Itoi Kazuo
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Patent number: 4458090Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: October 15, 1981Date of Patent: July 3, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Yoshiaki, Nishida Takashi, Itoi Kazuo
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Patent number: 4409238Abstract: Novel insecticidal compositions are comprised of an active isovalerate having the structural formula: ##STR1## wherein Z.sup.1 is hydrogen, ##STR2## Z.sup.2 is either ##STR3## when Z.sup.1 is hydrogen, or hydrogen when Z.sup.1 is either ##STR4## A, when Z.sup.1 is ##STR5## is cyano or ethynyl or, when Z.sup.1 is other than ##STR6## is hydrogen, cyano or ethynyl; X and Y which may be the same or different are chlorine or bromine.Type: GrantFiled: December 26, 1979Date of Patent: October 11, 1983Assignee: Kuraray Co., Ltd.Inventors: Fumio Mori, Yoshiaki Omura
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Patent number: 4400517Abstract: 1,2,4-triazol-(5)-yl-[thio] phosphates are disclosed having the formula ##STR1## wherein R.sup.1 =alkyl with from 1 to 5 carbon atoms;R.sup.2 =OR.sup.1, R.sup.1, C.sub.6 H.sub.5, NHR.sup.1, N(R.sup.1).sub.2 ;X=O, SR.sup.3 =H, alkyl with from 1 to 5 carbon atoms, C.sub.6 H.sub.5, benzyl, alkenyl with from 2 to 6 carbon atoms, alkynyl with from 2 to 6 carbon atoms; andR.sup.4 =vinyl, halovinyl, polyhalovinyl, vinyl substituted with aryl groups, alkyl groups with from 1 to 4 carbon atoms, O-alkyl groups with from 1 to 4 carbon atoms, S-alkyl groups with from 1 to 4 carbon atoms; haloalkyl, acetyl, cyclohexenyl, benzoyl ##STR2## Also disclosed are 1,2,4-triazole intermediates having the formula ##STR3## wherein: X, R.sup.3 and R.sup.4 have the same meanings as indicated above. The phosphate esters are useful in combatting infestations of pests such as orthoptera, aphides, diptera, lepidoptera, coleoptera, acari, nematodes.Type: GrantFiled: January 29, 1980Date of Patent: August 23, 1983Assignee: Montedison S.p.A.Inventors: Franco Gozzo, Pier M. Boschi, Angelo Longoni
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4356296Abstract: A diacrylate monomer represented by the formula: ##STR1## wherein R represent CF.sub.3 or C.sub.2 F.sub.5, R' represents --H or --sub.3, R" represents H or --(CF.sub.2).sub.n F, and n is an integer from 1 to 10, and polymer therefrom.Type: GrantFiled: February 25, 1981Date of Patent: October 26, 1982Assignee: The United States of America as represented by the Secretary of the NavyInventors: James R. Griffith, Jacques G. O'Rear
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Patent number: 4346235Abstract: A novel fluorine-containing compound of the formulaR.sub.1 --A--R.sub.2whereinA is ##STR1## R.sub.1 and R.sub.2 are each hydrogen or R.sub.3 OOC--CH.sub.2).sub.n, while R.sub.1 and R.sub.2 may not be hydrogen at the same time; X is hydrogen or halogen; R.sub.3 is hydrogen or a lower alkyl group; m is an integer of 1 to 5; and n is an integer of 4 to 11, and a process for preparing the same.Type: GrantFiled: June 10, 1980Date of Patent: August 24, 1982Assignees: Okamura Oil Mill Limited, Daikin Kogyo Co., Ltd.Inventors: Noboru Sonoda, Shinji Murai, Kazuhisa Takii
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Patent number: 4345084Abstract: Unsaturated eicosanoic acids and derivatives thereof which inhibit the synthesis of SRS-A are useful for treating and preventing asthma and allergic responses caused by SRS-A as well as useful in inhibiting inflammation.Type: GrantFiled: June 29, 1981Date of Patent: August 17, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, George W. Holland, Perry Rosen
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Patent number: 4345090Abstract: A substantially pure compound selected from the group consisting of the d-menthyl esters of 1RS-cis-, 1RS-cis/trans-, 1R-cis-, 1S-cis-, 1R-trans- and 1S-trans-3-(2,2-dichloro- and dibromo-vinyl)-2,2-dimethylcyclopropanecarboxylic acid, the 1-menthyl esters of 1RS-cis-, 1RS-trans-, 1RS-cis/trans-, 1R-cis-, 1S-cis-, 1R-trans- and 1S-trans-3-(2,2-dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid and the 1-menthyl esters of 1R-trans- and 1S-trans-3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid. The esters are produced by reacting enantiomers of the acids with d- or 1-menthol are selectively crystallizing.Type: GrantFiled: June 26, 1980Date of Patent: August 17, 1982Assignee: Bayer AktiengesellschaftInventors: Klaus Naumann, Rudolf Rauchschwalbe
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Patent number: 4316044Abstract: Isovaleric acid derivatives having the formula ##STR1## wherein typical representations of X is halophenyl, R.sub.1 is hydrogen or cyano, R.sub.2 is hydrogen or lower alkyl, and Y is halophenyl. These derivatives possess insecticidal and acaricidal properties. The process for their preparation is described.Type: GrantFiled: August 29, 1980Date of Patent: February 16, 1982Assignee: Nippon Soda Company LimitedInventors: Keiichi Ishimitsu, Isamu Kasahara, Tomio Yamada, Michihiko Matsuda, Hidemitsu Takahashi, Shuichi Soma
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Patent number: 4297505Abstract: A process for preparing a pentachloro-3-butenoic acid alkyl ester comprises reacting the corresponding 1-alkoxyheptachloro-3-butene with an aqueous solution of an alkali metal carbonate. In a preferred embodiment, the starting material 1-alkoxyheptachloro-3-butene is the solution obtained as the reaction product of the reaction of the corresponding 1-alkoxypentachloro-1,3-butadiene with chlorine.Type: GrantFiled: June 20, 1980Date of Patent: October 27, 1981Assignee: Chemische Werke Huels, AktiengesellschaftInventors: Gunther Maahs, Konrad Rombusch
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Patent number: 4293499Abstract: This invention provides a process for producing a carboxylate ester from a monoolefin and a carboxylic acid, in the presence of a solid catalyst comprising a composite of 5-sulfoisophthalic acid and a carrier substrate having a surface area between about 1-1000 m.sup.2 /gram.A carboxylate ester such as ethyl propionate is produced with a STY efficiency of at least 100 grams/liter hour.Type: GrantFiled: February 8, 1980Date of Patent: October 6, 1981Assignee: Celanese CorporationInventor: O. Richard Hughes
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Patent number: 4291057Abstract: Novel esters of halo-4-alkenoic acid compounds having pesticidal activity and methods of their preparation.Type: GrantFiled: July 2, 1979Date of Patent: September 22, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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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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Patent number: 4281176Abstract: Carboxylic acids are esterified with ethylene gas, to effect the formation of ethyl esters, by acid catalysis in the presence of at least one dissociating, inert and stable solvent which increases the acidity of the reaction medium.Type: GrantFiled: January 16, 1979Date of Patent: July 28, 1981Assignee: Rhone-Poulenc IndustriesInventors: Max Gruffaz, Odile Micaelli
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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: 4265819Abstract: A process for the preparation of a dihalogenovinylcyclopropanecarboxylic acid or an ester thereof, of the formula ##STR1## in which Hal each independently is fluorine, chlorine or bromine,R.sup.1 and R.sup.2 each independently is hydrogen or C.sub.1-4 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent carbon atom form a cycloaliphatic ring with up to 7 carbon atoms, andR.sup.3 is hydrogen, C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,which comprises reacting a 3-chloro-2-(2',2'-dihalovinyl)propanecarboxylic acid ester of the formula ##STR2## in which R.sup.4 is C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,with a base. The propane carboxylic acid esters are new and may be formed in situ by reacting a 3-(2',2'-dihalovinyl)-.gamma.-butyrolactone of the formula ##STR3## with a chlorinating agent and then with an alcohol of the formula R.sup.4 --OH.Type: GrantFiled: September 13, 1979Date of Patent: May 5, 1981Assignee: Bayer AktiengesellschaftInventor: Reinhard Lantzsch
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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: 4245113Abstract: A process for preparing a 2,3,4,4-tetrachloro-3-butenoic acid ester comprises reacting tetrachlorocyclobutenone in the presence of hexachloro-1,3-butadiene with an alcohol at a temperature of 125.degree.-200.degree. C.Type: GrantFiled: March 9, 1979Date of Patent: January 13, 1981Assignee: Chemische Werke Huels, A.G.Inventors: Gunther Maahs, Konrad Rombusch
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Patent number: 4217300Abstract: A process for the preparation of a dihalogenovinylcyclopropanecarboxylic acid or an ester thereof, of the formula ##STR1## in which Hal each independently is fluorine, chlorine or bromine,R.sup.1 and R.sup.2 each independently is hydrogen or C.sub.1-4 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent carbon atoms form a cycloaliphatic ring with up to 7 carbon atoms, andR.sup.3 is hydrogen, C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,which comprises reacting a 3-chloro-2-(2',2'-dihalovinyl)-propanecarboxylic acid ester of the formula ##STR2## in which R.sup.4 is C.sub.1-4 -alkyl or optionally substituted arylmethylor hetero-arylmethyl,with a base. The propane carboxylic acid esters are new and may be formed in situ by reacting a 3-(2',2'-dihalovinyl)-.gamma.-butyrolactone of the formula ##STR3## with a chlorinating agent and then with an alcohol of the formula R.sup.4 --OH.Type: GrantFiled: February 21, 1978Date of Patent: August 12, 1980Assignee: Bayer AktiengesellschaftInventor: Reinhard Lantzsch
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Patent number: 4214097Abstract: Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a .gamma.-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.Type: GrantFiled: January 20, 1978Date of Patent: July 22, 1980Assignee: Sagami Chemical Research CenterInventors: Kiyoshi Kondo, Kiyohide Matsui, Akira Negishi, Yuriko Takahatake
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Patent number: 4209604Abstract: Polymerizable acrylic monomers, and anaerobic adhesives which contain such monomers, wherein the acrylic monomers contain internal chain unsaturation in addition to terminal acrylic unsaturation.Type: GrantFiled: January 7, 1976Date of Patent: June 24, 1980Assignee: Estech Specialty Chemicals CorporationInventor: Gerhardt P. Werber
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Patent number: 4204073Abstract: A process for producing trimethyl oxo or hydroxy substituted cycopentenone food coloring agents including intermediates in this process.Type: GrantFiled: April 6, 1979Date of Patent: May 20, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Frank Kienzle
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Patent number: 4201787Abstract: Isovaleric acid ester derivatives, process for producing thereof, and insecticides containing said derivatives of the general formula I: ##STR1## wherein A represents O, NH, or CH.sub.2,R.sub.1 represents, if A is O or NH, an alkyl, an alkenyl, a haloalkyl and a haloalkenyl radical with 2-6 carbon atoms, and a radical selected from those of the general formulae II, III, IV and V: ##STR2## in which n is an integer of 1-3, R.sub.3 represents hydrogen, methyl group or chlorine atom; andif A is CH.sub.2, R.sub.1 represents an alkyl, an alkenyl, a haloalkyl and a haloalkenyl radical with 1-5 carbon atoms, whileR.sub.1 --A represents a naphthyl group bonding to the main chain at the .beta.-position, andR.sub.2 represents hydrogen or a cyano group.Type: GrantFiled: November 30, 1977Date of Patent: May 6, 1980Assignee: Dainippon Jochugiku Kabushiki KaishaInventors: Yoshio Katsuda, Yoshihiro Minamite
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Patent number: 4194052Abstract: A sulfonic acid salt of an acyloxyalkylamine is prepared by reaction of an organic acid or amino-acid with a sulfonic acid salt of an alkanolamine. Isocyanates are prepared therefrom by reaction with phosgene.Type: GrantFiled: May 1, 1969Date of Patent: March 18, 1980Assignee: Rohm and Haas CompanyInventors: Sheldon N. Lewis, Jerome F. Levy
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Patent number: 4161536Abstract: Aliphatic carboxylic acid esters of the formula ##STR1## wherein R.sub.1 represents hydrogen or methyl,X.sub.1 represents halogen,Y represents halogen or methyl, andZ represents cyano or ethynyl, processes for producing them and their use in combating pests.Type: GrantFiled: November 7, 1977Date of Patent: July 17, 1979Assignee: Ciba-Geigy CorporationInventors: Jozef Drabek, Saleem Farooq, Laurenz Gsell, Odd Kristiansen, Willy Meyer