Halogen Containing Reactant Patents (Class 568/348)
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Patent number: 4691052Abstract: Pyrethroid acids are prepared by conducting a cycloaddition reaction of a conjugated diene and a dihaloketene to form a dihalo-vinylcyclobutanone product; reducing the dihalo-vinylcyclobutanone product to a monohalo-vinylcyclobutanone product and then conducting a ring contraction with a base to form the desired acid product.Type: GrantFiled: May 30, 1986Date of Patent: September 1, 1987Assignee: S.C. Johnson & Son, Inc.Inventors: William T. Brady, Scott J. Norton, Jinrea Ko
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Patent number: 4686291Abstract: A process for the preparation of a methyl ketone of the formula ##STR1## in which R.sup.1 is alkyl, alkenyl, alkinyl, optionally substituted aryl or optionally substituted heteroaryl,R.sup.2 is alkyl,R.sup.3 is alkyl orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, from a cycloalkyl ring,comprising reacting a methyl sec.-alkyl ketone of the formula ##STR2## with a halide of the formulaR.sup.1 --CH.sub.2 --Xin whichX is halogen,in the presence of a base, a diluent, and a phase-transfer catalyst.Type: GrantFiled: November 26, 1985Date of Patent: August 11, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hans-Ludwig Elbe
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Patent number: 4681952Abstract: A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C.Type: GrantFiled: November 7, 1984Date of Patent: July 21, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4576741Abstract: Described in an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: November 14, 1984Date of Patent: March 18, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4499306Abstract: A 2,2-dihalo-6-halo-6-(1-haloisobutyl)cyclohexanone represented by the general formula ##STR1## where each of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 is a halogen atom.Type: GrantFiled: March 16, 1983Date of Patent: February 12, 1985Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Naoshi Imaki, Takemi Nakanome
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Patent number: 4492800Abstract: A process for the preparation of a 1,1-dichloro-alkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or together are alkanediyl,in the presence of at least an equimolar amount of magnesium. Advantageously,R.sup.1 is hydrogen,R.sup.2 is a C.sub.2 to C.sub.5 alkenyl radical or a radical of the formula ##STR4## Z is a cyano, acetal, carboxyl or C.sub.1 to C.sub.4 alkoxycarbonyl radical, or a radical of the formula COOM, andM is sodium or potassium,R.sup.3 each individually is a C.sub.1 to C.Type: GrantFiled: February 22, 1983Date of Patent: January 8, 1985Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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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: 4479901Abstract: Process for fluorinating an organic carbanion, which process comprises contacting and reacting, in a dry inert atmosphere, the compound of the formula selected from ##STR1## wherein ##STR2## is the carbanion, M is a counter ion, and X is a halide and a selected N-flouro-N-alkylsulfonamide.Type: GrantFiled: August 15, 1983Date of Patent: October 30, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: William E. Barnette
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Patent number: 4452813Abstract: A sulfonate derivative represented by the formula ##STR1## wherein R.sub.1 is lower alkyl, lower alkoxy or halogen, l is an integer of from 0 to 3, n is 0 or 1, A is straight-chain or branched-chain alkylene having 1 to 4 carbon atoms, and R.sub.2 is hydrogen or lower alkyl but, when n is 0 or 1 and A is straight-chain alkylene with 1 to 4 carbon atoms, is not hydrogen and the method for preparing the same.Type: GrantFiled: May 11, 1982Date of Patent: June 5, 1984Assignee: Taiho Pharmaceutical Company LimitedInventors: Setsuro Fujii, Toshihiro Hamakawa, Kazuo Ogawa, Yoshiyuki Muranaka, Sadao Hashimoto
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Patent number: 4449007Abstract: A process comprising the steps of reacting 1-acetyl-3,3-dimethylcyclohexane with an alkyl acetate, thereby forming a diketone having the structure: ##STR1## reacting the said diketone with an allyl halide to form a substituted diketone having the structure: ##STR2## which is transformed into the compound having the structure: ##STR3## by means of a retro-Claisen reaction.Type: GrantFiled: November 12, 1982Date of Patent: May 15, 1984Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker
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Patent number: 4385185Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.Type: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4371711Abstract: A method of producing a 4-hydroxycyclopentenone represented by the formula, ##STR1## wherein R.sub.1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R.sub.2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atoms, which comprises reacting a furylcarbinol compound of the formula, ##STR2## wherein R.sub.1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, ##STR3## wherein R.sub.1 is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, ##STR4## wherein R.sub.1 is a defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula,R.sub.2 MgXwherein R.sub.2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, ##STR5## wherein R.sub.1 and R.sub.Type: GrantFiled: May 20, 1980Date of Patent: February 1, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika
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Patent number: 4350824Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or the two radicals R.sup.3 together are alkanediyl,in the presence of at least an equimolar amount of a phosphorous acid triamide of the formulaP(NR.sup.4.sub.2).sub.3in whichR.sup.4 each independently is an alkyl radical, or the two radicals R.sup.4 together are alkanediyl.Advantageously,R.sup.1 is hydrogen,R.sup.2 a C.sub.2 to C.sub.Type: GrantFiled: February 23, 1981Date of Patent: September 21, 1982Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz
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Patent number: 4342704Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, aralkyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkynyl, aralkyl, aralkenyl or aryl radical, or cycloalkyl which is optionally substituted by halogen, alkyl, alkanoyl, carbamoyl, cyano or phenyl, orR.sup.1 and R.sup.2 together form a hydrocarbon chain which is optionally branched and/or optionally contains a fused benzene ring,comprising reacting an aldehyde or ketone of the formula ##STR2## with a dichloromethane-phosphonic acid ester of the formula ##STR3## in which R.sup.3 each independently is alkyl or phenyl or the two radicals R.sup.3 together are alkanediyl,in the presence of a base at a temperature between about -50.degree. and +50.degree. C.Type: GrantFiled: July 2, 1980Date of Patent: August 3, 1982Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4338466Abstract: Prostaglandin analogs and process for the preparation thereof as precursors or the synthesis of oligomeric mixtures exhibiting biological activity for protection of oxidative phosphorylation of degraded mitochondria. The analogs have the general formula: ##STR1## synthesized by O-alkylating a 2-alkylcyclopentane-1,3-dione to form an enol ether, reacting the ether with CH.sub.2 .dbd.CHMgBr to form a vinyl, oxidizing the vinyl with OsO.sub.4 and NaIO.sub.4 to form an aldehyde, and reacting the aldehyde with a sodium salt of dimethyl (2-oxoalkyl)phosphonate.Type: GrantFiled: April 2, 1981Date of Patent: July 6, 1982Assignee: The United States of America as represented by the Secretary of the NavyInventor: George L. Nelson
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Patent number: 4310702Abstract: Sulfuryl chloride is reacted in the liquid phase with an organic reactant which is a ketone or aromatic alcohol unsubstituted on both ortho carbons in the presence of a moderator selected from the group consisting of aliphatic alcohols of 1-3 carbons and aliphatic ethers of 2-6 carbons, with sufficient moderator being present to selectively produce a product substantially free of compounds with more than one chlorine atom per carbonyl or aromatic hydroxy. The products, such as monochloroacetone, monochlorocyclohexanone, monochlorophenol and 2,2-bis(3-chloro-4-hydroxyphenyl)propane, are useful as chemical intermediates and as monomers for flame retardant polymers.Type: GrantFiled: July 28, 1980Date of Patent: January 12, 1982Assignee: Allied CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4288613Abstract: A method of synthesis of cyclopentanones comprising cyclizing a 4-pentenal, preferably under an ethylene atmosphere, in the presence of a catalytically effective amount of a cyclizing, rhodium(I) para-substituted triarylphosphine catalyst.Type: GrantFiled: December 3, 1979Date of Patent: September 8, 1981Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4255351Abstract: Compounds of the formulae Ia, Ib, IIa and IIb ##STR1## are described, wherein R represents alkyl, haloalkyl, benzyl, naphthyl or substituted or unsubstituted phenyl and one of R.sub.1 and R.sub.2 represents methyl and the other represents hydrogen or methyl, or R.sub.1 and R.sub.2 together represent alkylene of 2 or 3 carbon atoms. The compound of the formulae Ia, Ib, IIa and IIb are valuable intermediates for the manufacture of pyrethroid pesticides or precursors thereof.Type: GrantFiled: March 5, 1979Date of Patent: March 10, 1981Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Hans Greuter, Daniel Bellus
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Patent number: 4252739Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.Type: GrantFiled: August 20, 1979Date of Patent: February 24, 1981Assignee: Emery Industries, Inc.Inventors: Richard G. Fayter, Jr., John F. White, Eugene G. Harris
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Patent number: 4240983Abstract: A process for the preparation of monohalogenated ketone is described wherein the ketone is vaporized in a collection vessel, and the vapors are caused to pass upwardly through a defined reaction zone into a condensation zone where they are condensed and caused to flow downwardly into the reaction zone. In the reaction zone their flow toward the collection zone is retarded, and while retarded, halogen is directed thereagainst. The halogenated ketone so formed is removed into the collection zone such as by directing condensed non-halogenated ketone thereagainst.Type: GrantFiled: October 2, 1979Date of Patent: December 23, 1980Assignee: Bayer AktiengesellschaftInventor: Rudiger Schubart
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Patent number: 4219505Abstract: 2,2,6,6-Tetrachloro(or tetrabromo)cyclohexanone is prepared by reacting in the liquid phase chlorine or bromine with a cyclohexanone compound of formula ##STR1## where Y is hydrogen or chlorine (to produce the tetrachloro compound) or hydrogen or bromine (to produce the tetrabromo compound) in the presence as catalyst of an organophosphorus compound of formula ##STR2## where Z is chlorine or bromine; n is 0 or 1; and when n is 0, m is 0 or 2, R.sup.1 is alkyl or phenyl, and R.sup.2 and R.sup.3 are hydrogen, alkyl or phenyl; and when n is 1, m is 0, and R.sup.1, R.sup.2 and R.sup.3 are the same and each is ##STR3## alkyl or phenyl, or R.sup.1 is hydrogen and R.sup.2 and R.sup.3 are alkyl or phenyl;or a salt thereof.Each alkyl is of 1-10 carbon atoms.Type: GrantFiled: May 1, 1978Date of Patent: August 26, 1980Assignee: Fisons LimitedInventors: Brian J. Needham, John Miller
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Patent number: 4217251Abstract: Novel cyclopentanone derivatives are found to be useful as flavor and odor modifying ingredients. The new compounds are particularly useful in the preparation of perfumes and perfumed products as well as for the aromatization of foodstuffs and beverages.Type: GrantFiled: May 11, 1979Date of Patent: August 12, 1980Assignee: Firmenich SAInventor: Khurshid P. Dastur
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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: 4212827Abstract: Process for the manufacture of canthaxanthin by oxidizing .beta.-carotene, retro-dehydro-carotene or echinenone with a salt of chloric or bromic acid in the presence of a catalyst and of an inert diluent or solvent.Type: GrantFiled: October 13, 1977Date of Patent: July 15, 1980Assignee: BASF AktiengesellschaftInventors: Joachim Paust, Joachim Schneider, Hagen Jaedicke
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Patent number: 4209450Abstract: A process for introducing an allyl-positioned carbonyl group into a 2,6,6-trimethylcyclohexene ring which carries a polyenyl radical in the 1-position, by oxidizing the ring with a halogen(V)-oxyacid or a salt of such an acid, and the new oxo compounds obtainable by the said process, which may be used as dyes for foodstuffs or cosmetics. The oxidation is carried out in the presence of a catalyst and of an inert diluent or solvent, in an acid medium. Suitable catalysts are bromine and iodine and the oxides of elements of groups Va, VIa, VIIa and VIII of the periodic table.Type: GrantFiled: January 10, 1978Date of Patent: June 24, 1980Assignee: BASK AktiengesellschaftInventors: Hagen Jaedicke, Joachim Paust
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Patent number: 4201717Abstract: 14.beta.-Hydroxyandrostanes and processes for the preparation thereof in which the 14.beta.-hydroxy group is fabricated internally by means of a novel cyclization of 8,14-seco-4,6,9(11)-androstatrien-3,14,17-triones is disclosed.The 14.beta.-hydroxyandrostanes are useful as precursors for the synthesis of cardenolides and related products.Type: GrantFiled: October 12, 1978Date of Patent: May 6, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Zdenek Valenta