The Halogen And The Aldehyde Or Ketone Are In The Same Reactant Patents (Class 568/394)
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Patent number: 9745241Abstract: The present invention relates to a production method of hexachloroacetone, including performing a reaction between at least one kind of compound (A) selected from the group consisting of acetone and chloroacetones having a chlorine atom number of from 1 to 5, and a chlorine molecule (B) in a solvent in the presence of an activated carbon, to obtain the hexachloroacetone.Type: GrantFiled: June 30, 2016Date of Patent: August 29, 2017Assignee: ASAHI GLASS COMPANY, LIMITEDInventors: Hidekazu Okamoto, Kouhei Tajima, Tsutomu Naganuma, Tomoyuki Fujita, Shingo Nomura
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Patent number: 9017638Abstract: Disclosed is a method for producing graphene functionalized at its edge positions of graphite. Organic material having one or more functional groups is reacted with graphite in reaction medium comprising methanesulfonic acid and phosphorus pentoxide, or in reaction medium comprising trifluoromethanesulfonic acid, to produce graphene having organic material fuctionalized at edges. And then, high purity and large scaled graphene and film can be obtained by dispersing, centrifugal separating the functionalized graphene in a solvent and reducing, in particular heat treating the graphene. According to the present invention graphene can be produced inexpensively in a large amount with a minimum loss of graphite. (FIG.Type: GrantFiled: February 24, 2012Date of Patent: April 28, 2015Assignee: Unist Academy-Industry Research CorpInventors: Jong Beom Baek, Eun Kyoung Choi, In Yup Jeon, Seo Yun Bae
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Patent number: 8957254Abstract: Process for synthesizing a chemical, in particular an agriculturally or pharmaceutically active compound, including: a first step comprising reacting a carboxylic acid halide with a vinyl ether to prepare a halogenated precursor of an alkenone; a second step comprising eliminating hydrogen halide from such precursor to form an alkenone, preferably by thermolysis under specific conditions; and a third step which uses the formed alkenone as a building block to synthesize the chemical. First step may be done in a liquid reaction medium comprising an alkenone or a halogenated alkenone precursor, or in a liquid reaction medium in turbulent state, specifically by creation of gas bubbles of the carboxylic acid halide herein. Second step may include a flash thermolysis, vacuum thermolysis, thermolysis under stripping with inert gas, and/or a thermolysis at a temperature from >90° C. to 120° C. Third step preferably comprises reacting the alkenone with a nitrogen-containing compound.Type: GrantFiled: October 4, 2013Date of Patent: February 17, 2015Assignee: Solvay SAInventors: Max Braun, Stefan Palsherm, Uta Claassen, Alain Lambert
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Patent number: 7919657Abstract: To provide a process for producing anhydrous hexafluoroacetone from hexafluoroacetone hydrate. To provide a process taking environment into consideration, that does not require a treatment of wastes, such as waste sulfuric acid, containing organic substances, which is inevitable in processes conducted hitherto using concentrated sulfuric acid, fuming sulfuric acid, and the like. A process for dehydrating a hexafluoroacetone hydrate, comprising introducing a hexafluoroacetone hydrate and hydrogen fluoride either as a mixture or separately into a distillation column, obtaining a composition containing hexafluoroacetone or a hexafluoroacetone-hydrogen fluoride adduct and hydrogen fluoride as a low boiling component, and obtaining a composition containing water and hydrogen fluoride as a high boiling component.Type: GrantFiled: August 28, 2008Date of Patent: April 5, 2011Assignee: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Tatsuya Hayasaka, Yoshiaki Miyamoto
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Publication number: 20100217049Abstract: [Task] To provide a process for producing anhydrous hexafluoroacetone from hexafluoroacetone hydrate. To provide a process taking environment into consideration, that does not require a treatment of wastes, such as waste sulfuric acid, containing organic substances, which is inevitable in processes conducted hitherto using concentrated sulfuric acid, fuming sulfuric acid, and the like. [Solving Means] A process for dehydrating a hexafluoroacetone hydrate, comprising introducing a hexafluoroacetone hydrate and hydrogen fluoride either as a mixture or separately into a distillation column, obtaining a composition containing hexafluoroacetone or a hexafluoroacetone-hydrogen fluoride adduct and hydrogen fluoride as a low boiling component, and obtaining a composition containing water and hydrogen fluoride as a high boiling component.Type: ApplicationFiled: August 28, 2008Publication date: August 26, 2010Applicant: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Tatsuya Hayasaka, Yoshiaki Miyamoto
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Patent number: 7361790Abstract: Epichlorohydrin is produced from acetone by (1) chlorinating acetone to form monochloroacetone; (2) disproportionating the monochloroacetone in the presence of a platinum catalyst, a strong acid and preferably a chloride source (for example, added as a salt or from hydrolysis of monochloroacetone) and some water to produce acetone and 1,3-dichloroacetone; (3) hydrogenating the 1,3-dichloroacetone in the presence of a catalyst to produce 1,3-dichlorohydrin; and (4) cyclizing the 1,3-dichlorohydrin with a base to produce epichlorohydrin.Type: GrantFiled: March 24, 2005Date of Patent: April 22, 2008Assignee: Dow Global Technologies Inc.Inventors: Marvin L. Dettloff, Marty J. Null
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Patent number: 7067702Abstract: A process for preparing vinyl substituted beta-diketones includes reacting a halogen-containing beta-diketone with an olefin in a reaction zone under Heck coupling reaction conditions in the presence of a catalyst, a base, and an organic phosphine to provide a vinyl substituted beta-diketone product.Type: GrantFiled: May 12, 2005Date of Patent: June 27, 2006Assignee: The Johns Hopkins UniversityInventors: Glen E. Southard, George M. Murray
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Patent number: 7030280Abstract: The present invention provides a process for producing an optically active ?-trifluoromethyl-?-hydroxycarbonyl compound represented by formula (3): comprising a step of reacting a fluoral equivalent represented by formula (1): with a carbonyl compound represented by formula (2): in the presence of an optically active amino acid or a derivative thereof.Type: GrantFiled: August 24, 2004Date of Patent: April 18, 2006Assignee: Central Glass Company, LimitedInventors: Kazumasa Funabiki, Hitoshi Yamamoto, Masashi Nagamori, Masaki Matsui
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Patent number: 7002043Abstract: The invention relates to a process for producing 1,1,1-trifluoroacetone, which is useful as an intermediate of pharmaceuticals and agricultural chemicals, or as a reagent for introducing fluorine-containing groups. This process includes the step of conducting a hydrogenolysis of a halogenated trifluoroacetone, which is represented by the formula [1], by a hydrogen gas, in a liquid phase containing water, in the presence of a catalyst containing a transition metal, where X represents a chlorine, bromine or iodine, and n represents an integer from 1 to 3. It is possible by the process to easily produce 1,1,1-trifluoroacetone with high purity.Type: GrantFiled: May 30, 2003Date of Patent: February 21, 2006Assignee: Central Glass Company, LimitedInventors: Masanori Tsukamoto, Fumiyoshi Yoshikawa, Masataka Fujimoto, Naoto Takada, Yoshikazu Sugimori, Junji Negishi
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Patent number: 6774266Abstract: A process for producing 1,1,1-trifluoroacetone includes the step of conducting in a gas phase a hydrogenolysis of a tetrafluoroacetone, which is represented by the general formula [1], by a hydrogen gas in the presence of a catalyst containing a transition metal, where X represents a chlorine, bromine or iodine, and n represents an integer from 0 to 2.Type: GrantFiled: November 20, 2002Date of Patent: August 10, 2004Assignee: Central Glass Company, LimitedInventors: Masanori Tsukamoto, Takashi Sakaya, Takayuki Nishimiya, Junji Negishi
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Publication number: 20030144557Abstract: The present invention provides a process for producing a linear perfluoroalkanone or a perfluorocycloalkanone, which comprises using as a starting material a combination of the same or different kinds of compounds that are selected from perfluoroalkanoyl halides represented by the formula: F(CF2)nCOX wherein X is F, Cl, Br or I and n is an integer of 1 to 8, or a perfluoroalkanedioyl dihalide represented by the formula: XOC(CF2)nCOX wherein X is F, Cl, Br or I and n is an integer of 3 to 8, and reacting the starting material with a metal carbonate or metal carbonates. According to the present invention, perfluoroalkanones can be produced with a good yield from relatively easily available starting materials by a simple synthesis method.Type: ApplicationFiled: October 18, 2002Publication date: July 31, 2003Inventors: Kouzou Noda, Hirokazu Aoyama
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Patent number: 6548712Abstract: The invention relates to a process for producing 1,1,1,5,5,5-hexafluoroacetylacetone. This process includes (a) hydrolyzing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone into a 1,1,1,5,5,5-hexafluoroacetylacetone hydrate; and (b) dehydrating the hydrate into the 1,1,1,5,5,5-hexafluoroacetylacetone with high purity from a material containing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone.Type: GrantFiled: March 15, 2001Date of Patent: April 15, 2003Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Nariaki II
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Patent number: 6342640Abstract: The invention relates to a process for producing 1,1,3,3-tetrachloro-1,3-difluoroacetone. This process includes fluorinating hexachloroacetone in a liquid phase by hydrogen fluoride in the presence of a catalyst containing a metal compound. This metal compound can be selected from tin halides, titanium halides, molybdenum halides, tungsten halides, niobium halides, tantalum halides, and iron halides. This process is suitable for producing 1,1,3,3-tetrachloro-1,3-difluoroacetone in an industrial scale.Type: GrantFiled: July 17, 2001Date of Patent: January 29, 2002Assignee: Central Glass Company, LimitedInventors: Ryo Nadano, Yoshihiko Goto
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Patent number: 6340776Abstract: A process for producing 1,1,1-trifluoroacetone includes the step of conducting a hydrogenolysis of a halogenated trifluoroacetone, which is represented by the general formula (1), by a hydrogen gas in the presence of a catalyst containing a transition metal, where X represents a chlorine, bromine or iodine, and n represents an integer from 1 to 3. It is possible to obtain 1,1,1-trifluoroacetone with a high yield by using the special catalyst.Type: GrantFiled: February 21, 2001Date of Patent: January 22, 2002Assignee: Central Glass Company, LimitedInventors: Yoshihiko Goto, Ryo Nadano, Takashi Sakaya, Takayuki Nishimiya
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Publication number: 20010037041Abstract: A process for producing 1,1,1-trifluoroacetone includes the step of conducting a hydrogenolysis of a halogenated trifluoroacetone, which is represented by the general formula (1), by a hydrogen gas in the presence of a catalyst containing a transition metal, 1Type: ApplicationFiled: February 21, 2001Publication date: November 1, 2001Inventors: Yoshihiko Goto, Ryo Nadano, Takashi Sakaya, Takayuki Nishimiya
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Patent number: 6262312Abstract: The invention relates to a process for producing 1,1,1-trifluoroacetone. This process includes reacting a halogenated acetone with a metal in the presence of a proton donor. This halogenated acetone is represented by the general formula (1): where X represents a chlorine atom, bromine atom or iodine atom, and n represents an integer from 1 to 3. It is possible to easily obtain 1,1,1-trifluoracetone from the halogenated acetone, which is easily available.Type: GrantFiled: May 26, 2000Date of Patent: July 17, 2001Assignee: Central Glass Company, LimitedInventor: Yoshihiko Goto
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Patent number: 6177595Abstract: A process of producing chlorofluoroacetones represented by a general formula where X represents independently chlorine atom or fluorine atom. The production process comprises fluorinating in a liquid phase pentachloroacetone by hydrogen fluoride in the presence of a catalyst comprising tin tetrahalide.Type: GrantFiled: September 10, 1999Date of Patent: January 23, 2001Assignee: Central Glass Company, LimitedInventors: Ryo Nadano, Takashi Sakaya, Mineo Watanabe, Yoshihiko Goto, Toshihiro Nakamichi, Shigeru Suenaga
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Patent number: 5481029Abstract: A process for preparing ketones, for example CF.sub.3 C(O)CH.sub.3, CF.sub.3 C(O)CH.sub.2 C(O)CF.sub.3 and CF.sub.3 C(O)CF.sub.2 H, in which .beta.-ketoesters are transesterified and decarboxylated using a carboxylic acid, for example trifluoroacetic acid, in the presence of a catalyst, particularly an "onium" salt of a carboxylic acid or an effective amount of a proton-donating acid, preferably a sulfonic acid such as alkyl- or arylsulfonic acids, or a mineral acid. The process is advantageously carried out in the absence of water, so that no formation of acetals or hydrates occurs, and no dehydrating step is needed. The process is simple to carry out, and if transesterification is carried out with a sufficiently active carboxylic acid, for example with trifluoroacetic acid, the presence of an additional catalyst is unnecessary.Type: GrantFiled: April 26, 1994Date of Patent: January 2, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Johannes Eicher, Werner Rudolph, Kerstin Eichholz
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Patent number: 5434289Abstract: A process for producing an optically active .beta.-hydroxyketone represented by formula (I): ##STR1## by catalytic asymmetrical aldol reaction is disclosed, comprising reacting a silyl-enol ether represented by formula (II): ##STR2## with a substituted aldehyde represented by formula (III):R.sup.5 CHO (III)in the presence of a binaphthol-titanium complex represented by formula (IV): ##STR3## An optically active .beta.-hydroxyketone is efficiently produced with diastereo-specificity and enantio-specificity.Type: GrantFiled: March 10, 1994Date of Patent: July 18, 1995Assignee: Takasago International CorporationInventors: Koichi Mikami, Satoru Matsukawa, Masaki Shimizu, Masahiro Terada, Noboru Sayo
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Patent number: 5391811Abstract: .alpha.-fluoro-.beta.-dicarbonyl compounds are prepared by reacting a halogenated dicarbonyl compound at temperatures of 20.degree. to 100.degree. C. with an addition product of hydrogen fluoride and a trialkylamine. This process is easy to carry out in technical terms and can also be carried out on a large scale.Type: GrantFiled: November 3, 1993Date of Patent: February 21, 1995Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5349107Abstract: Disclosed herein is a process for producing a .gamma.-hydroxyketone (2), which comprises asymmetrically hydrogenating a .gamma.-diketone (1) in the presence of a ruthenium-optically active phosphine complex as a catalyst ##STR1## wherein R.sup.1 and R.sup.2 mean individually an alkyl or phenyl group which may have a substituent group. According to the invention, optically active .gamma.-hydroxyketones useful in synthesizing optically active moiety in, biodegradable polymers, perfumes, intermediates for synthesizing medicines and the like can be efficiently prepared.Type: GrantFiled: October 1, 1993Date of Patent: September 20, 1994Assignee: Takasago International CorporationInventors: Seiji Watanabe, Shigeru Mitsuhashi, Hidenori Kumobayashi
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Patent number: 5288915Abstract: Ketones are prepared by admixing at least one gem-dichloro compound with at least one acid such that the ketone wherein the keto-oxygen replaces the gem-dichloro group is formed. The reaction is exemplified by the reaction of 9,9-dichlorofluorene with an acid such that fluorenone is formed. This process has the advantage that no oxidizing agent is used.Type: GrantFiled: December 17, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventor: Marlin E. Walters
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Patent number: 5250740Abstract: A method for forming a layer of a Group II or III fluoride on a semiconductor substrate (e.g. as epitaxial insulating layer) comprising vaporising a precursor (I), where M is Be, Ca, Sr, Ba or lanthanide, b and d are 0 or 1. A, B, C and D are independently (IIA) or (IIB), X being O, S, NR, PR where R is H, alkyl, perfluoroalkyl; Y is perfluoroalkyl, fluoroalkenyl, fluoroalkylamine or fluoroalkenylamine; Z is H, F, alkyl, perfluoroalkyl or perfluoroalkenyl; and then decomposing the precursor vapor to form M fluoride. A preferred precursor for CaF.sub.2 is a calcium 1,1,1,5,5,5-hexafluor-2,4-pentanedione complex where b and d are 0.Type: GrantFiled: January 9, 1992Date of Patent: October 5, 1993Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Kevin J. Mackey, Anthony W. Vere, Donald C. Bradley, Daro M. Frigo, Marc M. Faktor, deceased
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Patent number: 5164517Abstract: This invention relates to a process for preparing fluoropolyethers and perfluoropolyethers having neutral and/or functional end groups and a lower molecular weight by a selective catalytic cleavage of the corresponding higher molecular weight fluoropolyethers and perfluoropolyethers, characterized in that said cleavage is carried out by operating in the presence of a catalyst system consisting of a combination of silicon dioxide with at least an oxide, a fluoride or an oxyfluoride of a metal selected from Al, Ti, V, Cr, Co. Fe, Ni, Mo, Zn, Cu, Cd, Mn, Sb, Sn, Zr, Sc, Y, La and homologs thereof, Pb, Mg, W.Type: GrantFiled: January 29, 1991Date of Patent: November 17, 1992Assignee: Ausimont S.p.A.Inventors: Giuseppe Marchionni, Guglielmo Gregorio, Ugo De Patto, Mario Padovan
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Patent number: 4906414Abstract: New chlorinated .beta.-ketoesters of the formula: ##STR1## wherein R represents alkyl of 1 through 6 carbon atoms or alkenyl of 2 through 6 carbon atoms, and R.sub.1 represents alkyl of 1 through 4 carbon atoms, their preparation and their use for the preparation of ethylenic ketones of the formula: ##STR2## wherein R is as hereinbefore defined.Type: GrantFiled: January 25, 1989Date of Patent: March 6, 1990Assignee: Rhone-Poulenc SanteInventor: Didier Morel
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Patent number: 4845301Abstract: A process for the preparation of .alpha.-hydroxyketones ##STR1## having a high purity in a good yield from a compound ##STR2## by rearrangement reaction in aqueous alkaline solution, where R.sub.1 and R.sub.3 each represent an alkyl, alkenyl or aryl group, R.sub.2 represents a hydrogen atom or an alkyl, alkenyl or aryl group, and X represents hydroxyl group or a halogen atom.Type: GrantFiled: September 8, 1987Date of Patent: July 4, 1989Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuo Sato, Noritsugu Yamasaki, Ichirou Takase
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Patent number: 4837365Abstract: New chlorinated .beta.-ketoesters of the formula: ##STR1## wherein R represents alkyl of 1 through 6 carbon atoms or alkenyl of 2 through 6 carbon atoms, and R.sub.1 represents alkyl of 1 through 4 carbon atoms, their preparation and their use for the preparation of ethylenic ketones of the formula: ##STR2## wherein R is as hereinbefore defined.Type: GrantFiled: August 13, 1984Date of Patent: June 6, 1989Assignee: Rhone-Poulenc SanteInventor: Didier Morel
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Patent number: 4579974Abstract: Disclosed is a continuous catalytic process for the preparation of hexafluoroacetone comprising reacting in a first fluorination step a mixture of hydrofluoric acid and a chlorofluoroacetones recyclate, then in a second fluorination step, a mixture containing the effluent issuing from the first step and fresh hexachlorofluoroacetone, on a catalyst comprising gamma alumina impregnated with chromium sesquioxide Cr.sub.2 O.sub.3 in an amount of 1.5 to 4 atoms of chromium per liter of alumina and activated between 300.degree. C. and 400.degree. C. by means of a mixture of hydrofluoric acid and 1,1,2-trichloro-1,2,2-trifluoro-ethane.Type: GrantFiled: December 7, 1984Date of Patent: April 1, 1986Assignee: ATOCHEMInventors: Bernard Cheminal, Henri Mathais
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Patent number: 4464530Abstract: A process is disclosed for production of a sugar ketal, which comprises reacting a sugar with a ketone in the presence of hydrogen iodide. The formation of unfavorable by-products can be reduced to a trace amount. The process offers the objective ketal in improved yields, and an industrially advantageous process.Type: GrantFiled: March 23, 1983Date of Patent: August 7, 1984Assignee: Takeda Chemical Industries, Ltd.Inventors: Koichi Matsumura, Tetsuya Aono
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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: 4267381Abstract: A fluorine derivative of 3,3-dimethyl-butan-2-one, of the formula ##STR1## in which X is hydrogen or fluorine,is produced by reacting a metal fluoride in a diluent and at elevated temperature with a sulphonic acid ester of the formula ##STR2## in which R is optionally substituted alkyl or optionally substituted aryl, andY is hydrogen or O--SO.sub.2 --R.The product is useful in the synthesis of fungicides.Type: GrantFiled: September 20, 1979Date of Patent: May 12, 1981Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Jorg Stetter, Dieter Arlt, Wolfgang Kramer
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Patent number: 4254132Abstract: A 2-acyloxy-1-azolyl-3,3-dimethyl-2-phenoxy-butane of the formula ##STR1## in which A represents a nitrogen atom or the CH group,R represents alkyl, alkenyl, alkynyl, alkoxy, alkoxyalkyl, cycloalkyl, halogenoalkyl, optionally substituted phenyl, optionally substituted phenylalkyl, optionally substituted phenoxyalkyl, alkylamino, dialkylamino, optionally substituted phenylamino, halogenalkylamino, alkoxycarbonylamino, or alkoxyalkylamino,X represents hydrogen, halogen or alkylcarbonyloxy,Y represents halogen or alkylcarbonyloxy,Z represents halogen, alkyl, cycloalkyl, alkoxy, halogenoalkyl, alkylthio, alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylalkyl, cyano or nitro, andn represents 0, 1, 2, 3, 4 or 5, the substituents Z being selected independently of one another when n is 2 or more,and salts and complexes thereof which possess fungicidal properties.Type: GrantFiled: February 22, 1979Date of Patent: March 3, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Karl H. Buchel, Paul-Ernst Frohberger, Wilhelm Brandes
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Patent number: 4251467Abstract: Symmetrical 1,3-dichloroacetone is prepared by contacting chlorine with an aqueous mixture of acetone, monochloroacetone, or mixtures thereof and an iodine-containing promoter.Type: GrantFiled: September 2, 1976Date of Patent: February 17, 1981Assignee: Chevron Research CompanyInventor: Victor P. Kurkov
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Patent number: 4229470Abstract: Compounds are disclosed which have a juvenile hormone action on insects and also exhibit acaricide action. Said compounds are unsaturated aliphatic compounds having a trichloromethyl end group and the other end group of which is a phenol group which may be substituted and/or condensed, and which are capable of hindering the growth of insects from the larval to the adult stage and also exhibit an acaricide action on both adult acari and their eggs.Type: GrantFiled: January 17, 1979Date of Patent: October 21, 1980Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Angelo Longoni