Halogen Containing Reactant Patents (Class 568/393)
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Patent number: 8552222Abstract: The present invention relates to a continuous process for producing a haloalkenone ether of the Formula (I) wherein R1 is C1-C6 haloalkyl, R2 is a C1-C6 alkyl or phenyl, the process comprising:—(i) reacting, in a first continuous stirred tank reactor comprising a solvent, a halide of Formula (II) wherein R1 is as previously defined and R3 is halogen, with a vinyl ether of Formula (III) wherein R2 is as previously defined, to form an intermediate compound of Formula (IV), wherein the concentration of the vinyl ether of Formula (III) in the reaction mass is 15% or less w/w; and (ii) transferring the reaction mass from the first continuous stirred tank reactor into a subsequent continuous stirred tank reactor, wherein the conditions within the subsequent reactor permit the elimination of hydrogen halide (HR3) from the intermediate compound of Formula (IV) to provide the haloalkenone ether of Formula (I).Type: GrantFiled: March 2, 2010Date of Patent: October 8, 2013Assignee: Syngenta Crop Protection LLCInventors: David Anthony Jackson, Florian Schleth, Devender Singh Negi, Werner Pfaff
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Publication number: 20120095265Abstract: The present invention relates to a continuous process for producing a haloalkenone ether of the Formula (I) wherein R1 is C1-C6 haloalkyl, R2 is a C1-C6 alkyl or phenyl, the process comprising:—(i) reacting, in a first continuous stirred tank reactor comprising a solvent, a halide of Formula (II) wherein R1 is as previously defined and R3 is halogen, with a vinyl ether of Formula (III) wherein R2 is as previously defined, to form an intermediate compound of Formula (IV), wherein the concentration of the vinyl ether of Formula (III) in the reaction mass is 15% or less w/w; and (ii) transferring the reaction mass from the first continuous stirred tank reactor into a subsequent continuous stirred tank reactor, wherein the conditions within the subsequent reactor permit the elimination of hydrogen halide (HR3) from the intermediate compound of Formula (IV) to provide the haloalkenone ether of Formula (I).Type: ApplicationFiled: March 2, 2010Publication date: April 19, 2012Applicant: SYNGENTA CROP PROTECTION, LLCInventors: David Anthony Jackson, Florian Schleth, Devender Singh Negi, Werner Pfaff
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Patent number: 7795474Abstract: This invention offers 6,8,10-undecatrien-3-one or 6,8,10-undecatrien-4-one which are represented by the following formula (1) [in the formula, either one of A and B stands for carbonyl group and the other stands for methylene group, and the wavy line signifies cis-form, trans-form, or a mixture of cis- and trans-form at an optional ratio] and which can reproduce an odor rich in naturality and freshness.Type: GrantFiled: April 3, 2008Date of Patent: September 14, 2010Assignee: T. Hasegawa Co., Ltd.Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Norio Miyazawa, Tomoko Maeda
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Publication number: 20100137648Abstract: This invention offers 6,8,10-undecatrien-3-one or 6,8,10-undecatrien-4-one which are represented by the following formula (1) [in the formula, either one of A and B stands for carbonyl group and the other stands for methylene group, and the wavy line signifies cis-form, trans-form, or a mixture of cis- and trans-form at an optional ratio] and which can reproduce an odor rich in naturality and freshness.Type: ApplicationFiled: April 3, 2008Publication date: June 3, 2010Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Norio Miyazawa, Tomoko Maeda
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Patent number: 7456322Abstract: A process for preparing 1,3-dibromoacetone, 1-3-dichloroacetone and epichlorohydrin which comprises: (a) re-acting acetone with 2 moles of bromine to make a mixture of brominated acetone derivatives and byproduct hydrogen bromide; (b) equilibrating the mixture of brominated acetone derivatives and hydrogen bromide to produce 1,3-dibromoacetone as the major product; (c) crystallizing the 1,3-dibromoacetone; and (d) isolating the 1,3-dibromoacetone. The process may further include the steps of (e) reacting the 1,3-dibromoacetone with a chloride source to produce 1,3-dichloroacetone; (f) hydrogenating the isolated 1,3-dichloroacetone to produce 1,3-dichlorohydrin; and (g) cyclizing the 1,3-dichlorohydrin with a base to produce epichlorohydrin.Type: GrantFiled: May 17, 2005Date of Patent: November 25, 2008Assignee: Dow Global Technologies Inc.Inventor: Clark S. Davis
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Patent number: 7060859Abstract: The invention concerns the use of a solid basic catalyst comprising a hydrotalcite structure wherein part at least of the compensating anions are fluoride anions F? for producing Knoevenagel of Michael condensation reactions. The invention also concerns novel solid basic catalysts comprising a hydrotalcite structure characterized by a Mg/Al molar ratio ranging between 2.5 and 3.8 wherein at least part of the compensating anions are fluoride anions F?, and methods for preparing said novel catalysts.Type: GrantFiled: June 6, 2005Date of Patent: June 13, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Francois Figueras, Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Vattipally Neeraja, Kottapalli Koteswara Rao
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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: 7005551Abstract: A process is provided for the production of acetaldehyde from formaldehyde and methyl chloride. In the process formaldehyde is reacted in the vapor phase with methyl chloride to produce acetaldehyde and hydrogen chloride. The byproduct hydrogen chloride may be recovered from the process to produce additional methyl chloride from methyl alcohol.Type: GrantFiled: March 8, 2005Date of Patent: February 28, 2006Inventor: John Stauffer
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Patent number: 6969776Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.Type: GrantFiled: June 17, 2004Date of Patent: November 29, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
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Patent number: 6933414Abstract: A process is provided for the production of acetone from formaldehyde and methyl chloride. In the process formaldehyde is reacted in the vapor phase with methyl chloride to produce acetone and hydrogen chloride. Acetaldehyde may be formed as an intermediate in the reaction. The byproduct hydrogen chloride may be recovered from the process to produce additional methyl chloride from methyl alcohol.Type: GrantFiled: June 21, 2004Date of Patent: August 23, 2005Inventor: John E. Stauffer
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Patent number: 6933413Abstract: The present invention provides a process for the preparation of hexafluoroacetone characterized by bringing hexafluoro-1,2-epoxypropane into contact with at least one catalyst selected from the group consisting of titanium oxide catalysts and fluorinated titanium oxide catalysts to isomerize hexafluoro-1,2-epoxypropane; and a process for the preparation of hexafluoroacetone hydrate characterized by absorbing the hexafluoroacetone prepared by the above process into water to produce crude hexafluoroacetone hydrate, neutralizing the crude hexafluoroacetone hydrate with an alkali, and distilling the resulting mixture. According to the invention, high-purity hexafluoroacetone can be obtained by isomerization of hexafluoro-1,2-epoxypropane with little formation of by-products, and substantially acid-free high-purity hexafluoroacetone hydrate can also be obtained.Type: GrantFiled: July 2, 2002Date of Patent: August 23, 2005Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
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Patent number: 6803488Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.Type: GrantFiled: February 26, 2003Date of Patent: October 12, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
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Publication number: 20040186322Abstract: The present invention provides a process for the preparation of hexafluoroacetone characterized by bringing hexafluoro-1,2-epoxypropane into contact with at least one catalyst selected from the group consisting of titanium oxide catalysts and fluorinated titanium oxide catalysts to isomerize hexafluoro-1,2-epoxypropane; and a process for the preparation of hexafluoroacetone hydrate characterized by absorbing the hexafluoroacetone prepared by the above process into water to produce crude hexafluoroacetone hydrate, neutralizing the crude hexafluoroacetone hydrate with an alkali, and distilling the resulting mixture. According to the invention, high-purity hexafluoroacetone can be obtained by isomerization of hexafluoro-1,2-epoxypropane with little formation of by-products, and substantially acid-free high-purity hexafluoroacetone hydrate can also be obtained.Type: ApplicationFiled: January 9, 2004Publication date: September 23, 2004Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
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Publication number: 20040024256Abstract: The present invention provides a process and apparatus for selectively halogenating a ketone of the formula (I) 1Type: ApplicationFiled: July 1, 2002Publication date: February 5, 2004Inventor: Dennis E. Jackman
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Patent number: 6455728Abstract: A process for fluorinating &bgr;-dicarbonyls to form the corresponding &agr;-fluorinated-&bgr;-dicarbonyl compounds is provided. The process is represented by the following reaction scheme: where R1 is H, alkyl or alkoxy, R2 is H, alkyl or perfluoroalkyl, and R3 is H, Cl, Br, I or alkyl. Use of oxygen in the fluorine stream yields a product which is 90-96% pure and contains radical fluorination impurity levels which are 10-20% lower than when oxygen is not used.Type: GrantFiled: November 1, 1999Date of Patent: September 24, 2002Assignee: Air Products and Chemicals, Inc.Inventors: William Jack Casteel, Jr., Wade H. Bailey, III
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Publication number: 20020010372Abstract: 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: ApplicationFiled: July 17, 2001Publication date: January 24, 2002Inventors: Ryo Nadano, Yoshihiko Goto
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Patent number: 6307105Abstract: A process for providing an &agr;-fluorinated-&bgr;-dicarbonyl includes electrophilically fluorinating a &bgr;-dicarbonyl with bis-fluoroxydifluoromethane in the presence of an acid to provide the &agr;-monofluorinated-&bgr;-dicarbonyl. The acid is preferably hydrofluoric acid. Preferred &bgr;-dicarbonyls include methyl-3-oxopentanoate and ethyl-4,4,4-trifluoroacetoacetate. The process can limit radical impurity byproducts to no more than 4% in some cases, and less than 0.5% in other cases. Theoretical yields of 95% &agr;-monofluorinated-&bgr;-dicarbonyl are possible in some cases.Type: GrantFiled: July 19, 2000Date of Patent: October 23, 2001Assignee: Air Products and Chemicals, Inc.Inventors: William Jack Casteel, Jr., Robert George Syvret, Wade Hampton Bailey, III
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Patent number: 6300522Abstract: A process is provided for the preparation of compounds of Formula (1): wherein X1 and X2 are each independently H, Cl or F, provided that at least one of X1 and X2 is Cl or F; one of R1 and R2 is H and the other is OH; and R5 is an unsubstituted alkyl, preferably a C1-6 alkyl, group.Type: GrantFiled: November 29, 2000Date of Patent: October 9, 2001Assignee: Avecia LimitedInventors: John Crosby, Kevin Douglas Bailey, Michael John Monteith
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Patent number: 6288281Abstract: A process for the carbonylation of saturated hydrocarbons to give an oxygenated saturated hydrocarbon is disclosed and claimed. The process involves using an acidic ionic liquid catalyst to catalyze the carbon monoxide addition to the saturated hydrocarbon at reaction conditions to form an oxygenate. The acidic ionic liquid comprises a Lewis or Bronsted acid in combination with a quaternary nitrogen-containing compound. A specific example is a mixture of aluminum chloride and n-butylpyridinium chloride.Type: GrantFiled: November 16, 2000Date of Patent: September 11, 2001Assignee: UOP LLCInventors: Laszlo T. Nemeth, Jeffery C. Bricker, Jennifer S. Holmgren, Lyle E. Monson
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Patent number: 6252120Abstract: 2,4,4,7-Tetramethyl-oct-6-en-3-one, as a perfume component, imparts new smell facets to perfume compositions. It can be prepared in a good yield by prenylation of 1-chloro-3-methyl-2-butene in a 2-phase process.Type: GrantFiled: October 9, 1996Date of Patent: June 26, 2001Assignee: Haarmann & Reimer GmbHInventors: Erich Dilk, Peter Wörner
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Patent number: 6225506Abstract: A method for synthesizing an alkyl-2-one by reacting a 2-alkene halide with a 2,4-alkanedione in an alkylene glycol medium having a boiling point higher than said alkene-2-one is described.Type: GrantFiled: December 13, 1999Date of Patent: May 1, 2001Assignee: Boulder Scientific CompanyInventor: Jeffrey M. Sullivan
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Patent number: 6121500Abstract: A mixture of water and a glycol, such as ethylene glycol, is employed as the solvent for the reaction between 1,6-dibromo-2-naphthol and an alkali metal sulfite in the preparation of 6-bromo-2-naphthol and its derivatives to effect a substantial reduction in reaction time. The glycol/water mol ratio is ordinarily in the range of 0.1-0.5/1, preferably 0.3/0.5/1.Type: GrantFiled: March 4, 1999Date of Patent: September 19, 2000Assignee: Albemarle CorporationInventor: Mahmood Sabahi
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Patent number: 6020502Abstract: A method for the fluorination of 1,3-diketones and 1,3-ketoesters is disclosed.Type: GrantFiled: February 21, 1997Date of Patent: February 1, 2000Assignee: BNFL Fluorochemicals Ltd.Inventors: Richard D. Chambers, John Hutchinson, Martin P. Greenhall, John S. Moilliet, Julie Thomson
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Patent number: 5786515Abstract: A simple, high yielding synthesis of a-chloro ketones is described, involving acylation of Grignard and organolithium reagents with N-methoxy-N-methylchloroacetamide. The efficiency of the process is further enhanced by recycling N,O-dimethylhydroxylamine.Type: GrantFiled: August 30, 1996Date of Patent: July 28, 1998Assignee: Merck & Co., Inc.Inventors: Ulf H. Dolling, Lisa F. Frey, Richard D. Tillyer, David M. Tschaen
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Patent number: 5736274Abstract: A polymer containing a recurring unit of a conjugated N-fluoropyridinium salt and an active material for a positive electrode, an electrolyte, a battery material for the positive electrode and a battery which use such a polymer. That polymer provides a battery material and a primary battery or a secondary battery which have high electromotive force, high energy density, high environmental acceptability, a low internal resistance in charging and discharging and strong recoverability of the electromotive force, and can be useful as a fluorinating agent.Type: GrantFiled: April 18, 1997Date of Patent: April 7, 1998Assignee: Daikin Industries, Ltd.Inventors: Teruo Umemoto, Kenji Adachi, Ginjiro Tomizawa, Sumi Ishihara, Masayuki Nagayoshi
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Patent number: 5703248Abstract: The present invention concerns a novel process for the selective trihalogenation of ketones employing organic halogen salts.Type: GrantFiled: May 26, 1995Date of Patent: December 30, 1997Inventors: Jeffrey S. Rommel, James T. Traxler, Richard R. Boettcher
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Patent number: 5569778Abstract: A process for preparing a fluorine-containing dicarbonyl compound of the formula: R.sup.1 COCFR.sup.2 COR.sup.3 in which R.sup.1 is a hydrogen atom, or a substituted or unsubstituted alkyl or aryl group; R.sup.2 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl or aryl group; and R.sup.3 is a hydrogen atom, or a substituted or unsubstituted alkyl, aryl, alkoxy or aryloxy group, provided that at least two of R.sup.1, R.sup.2 and R.sup.3 may together form a part of a cyclic structure with or without a hetero atom, by reacting a dicarbonyl compound of the formula: R.sup.1 COCHR.sup.2 COR.sup.3 in which R.sup.1, R.sup.2 and R.sup.3 are the same as defined above with fluorine (F.sub.2) in at least one solvent selected from the group consisting of halogenated hydrocarbons having 1 to 5 carbon atoms and nitrile compounds, or in a solvent in the presence of a salt, or an acid having pKa of 6 or less.Type: GrantFiled: April 28, 1995Date of Patent: October 29, 1996Assignee: Daikin Industries Ltd.Inventors: Teruo Umemoto, Ginjiro Tomizawa
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Patent number: 5449801Abstract: A process for the selective high yield halogenation R--CH.sub.3 wherein R is ##STR1## Si(Cl).sub.m (CH.sub.3).sub.n, wherein m is 1 to 3, n is 1 to 3 and m+n is 3; phenyl; or phenyl substituted with Cl, Br, F, OR.sup.1, SR.sup.1 or NO.sub.2 ; R.sup.1 is C.sub.1 -C.sub.3 alkyl; and X is chlorine or bromine; under reactive distillation conditions which continuously and selectively separate the mono, di, or trihalogenated product from the reaction zone and which does not require recycling of the starting materials is disclosed.Type: GrantFiled: July 14, 1993Date of Patent: September 12, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Chris S. Barnum, Charles T. Blaisdell
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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: 5231205Abstract: The magnesium complexes of cyclic hydrocarbons, such as 1,2-dimethylenecycloalkanes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, or bromoalkylnitriles serve as a convenient method for synthesizing spirocyclic systems. Significantly, spirocarbocycles prepared by thisThe present invention was made with Government support under Contract No. GM35153 awarded by the National Institute of Health. The Government has certain rights in the invention.Type: GrantFiled: September 23, 1991Date of Patent: July 27, 1993Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5231232Abstract: Methods of forming unsaturated C-18 ketones which can be used in the synthesis of Vitamins E and K.sub.1 are disclosed. One procedure involves coupling a C-9 primary allylic halide to a carbonyl-group-containing C-9 terminal alkyne. A second, two-step procedure employs a C-4 bis allylic halide (molar excess) and a carbonyl-group-containing C-9 terminal alkyne to form a C-13 primary allylic halide. The C-13 primary allylic halide can then be converted to the desired C-18 ketone by reaction with 2-methyl-3-butyn-2-ol. Novel C-18 ketones (e.g., 14-hydroxy-6,14-dimethyl-10-methylene-5-pentadecen-7,12-diyn-2-one), C-13 allylic halides (e.g., 10-chloromethyl-6-methyl-5,10-undecadien-7-yn-2-one) and C-9 allylic halides (e.g., 6-chloromethyl-2-methyl-6-hepten-3-yn-2-ol) are formed in the process.Type: GrantFiled: December 18, 1991Date of Patent: July 27, 1993Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 5124486Abstract: The invention provides a process for the preparation of cyclic ketones of the general formula ##STR1## in which R represents an optionally substituted alkyl or cycloalkyl group and R.sup.1 and R.sup.2 independently represent an optionally substituted alkyl, cycloalkyl or aryl group, which comprises heating a compound of the general formula ##STR2## in which X represents a chlorine or bromine atom and R is as defined above, with a compound of the general formula ##STR3## in which R.sup.1 and R.sup.2 are as defined above, in the presence of an organic acid.Certain cyclic ketones of formula (I) are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: April 19, 1991Date of Patent: June 23, 1992Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4740612Abstract: A novel process for producing a .beta.-dihalogenoethenylcyclopropane derivative of the formula, ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl group, R.sub.3 is a hydrogen atom, lower alkyl, acyl, carboxyl or alkoxycarbonyl group and R is a hydrogen atom or a lower alkyl group and each of Y.sub.1 and Y.sub.2 is a fluorine, chlorine or bromine atom respectively, which is an acidic moiety of the useful synthetic insecticides of the pyrethrin type, which process comprises a combination of a series of sequential steps starting from alkyl 3-butenyl ketone derivative of the formula (I), which may be shown according to the following reaction scheme: ##STR2## According to this process, objective compound of the formula (VI) having any cis/trans ratio can be produced by selecting the reaction condition of the Stages II-1, II-2, and IV-2.Type: GrantFiled: February 5, 1986Date of Patent: April 26, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Matsuo, Nobushige Itaya, Osamu Magara
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Patent number: 4734524Abstract: A pheromonal compound produced by the western corn rootworm has been identified as 8-methyl-2-decanol propanoate (8-M-2-DP) having the structural formula: ##STR1## A synthesis has been devised for racemic 8-M-2-DP which demonstrates activity toward the western corn rootworm comparable to its natural counterpart. Other diabroticites including the Mexican corn rootworm and the northern corn rootworm also respond to the synthetic compound. By attracting rootworms to field traps, 8-M-2-DP is a useful tool for the monitoring and control of these major agricultural pests.Type: GrantFiled: August 16, 1982Date of Patent: March 29, 1988Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Paul L. Guss, James H. Tumlinson, III, Philip E. Sonnet, Adron T. Proveaux
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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: 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: 4642385Abstract: In the reaction of pinacolone with chlorine in a solvent to produce monochloropinacolone, the improvement which comprises employing a solvent such as an alcohol which contains HCl at the outset of the reaction whereby the amount of by-product dichloropinacolone produced is reduced.Type: GrantFiled: November 19, 1985Date of Patent: February 10, 1987Assignee: Mobay CorporationInventor: Dennis E. Jackman
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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: 4602117Abstract: A process for the preparation of halogenated 3,3-dimethyl-5-hexen-2-ones of the formula ##STR1## wherein an acetic acid ester of the formula ##STR2## is reacted with 2-methylbutan-3-one of the formula ##STR3##Type: GrantFiled: November 6, 1985Date of Patent: July 22, 1986Assignee: Bayer AktiengesellschaftInventor: Reinhard Lantzsch
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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: 4524221Abstract: Process for the production of an acyloin comprising the steps of:A. reacting a Grignard reagent with silylated cyanohydrin,B. treating the reaction product of step A with aqueous acid, andC. recovering the resulting acyloin.Acyloins thus formed are useful as photoinitiators for initiation of free radical polymerization reactions.Type: GrantFiled: February 22, 1983Date of Patent: June 18, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventors: Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
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Patent number: 4465863Abstract: Described are compounds defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl with the provisos that:(i) the sum total of carbon atoms in R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is three;(ii) when R.sub.7 is methyl, then R.sub.5 and R.sub.6 are both methyl, and(iii) when either R.sub.3 or R.sub.4 is methyl, then R.sub.7 is hydrogenand wherein R.sub.8 represents hydrogen, acetyl, alkoxyacyl, hydroxyacyl, or alkali metal carboxylate; and R.sub.9 is hydrogen or allyl with the additional proviso that R.sub.8 and R.sub.9 are not both hydrogen.Also described is the use of the subgenus of such compounds defined according to the structure: ##STR2## in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid nonionic, cationic, anionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations and the like.Type: GrantFiled: November 12, 1982Date of Patent: August 14, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz, Marie R. Hanna
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Patent number: 4460793Abstract: A process for the production of a monochloromethyl ketone of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 each independently is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkinyl or aryl radical, orR.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted carbocyclic ring,comprising reacting a 1,1-dichloroalkene of the formula ##STR2## with a phenolate of the formula ##STR3## in which R.sup.4 each independently is a halogen atom, a nitro group, or an optionally substituted alkyl, alkoxy or aryl radical,n is 0, 1, 2 or 3, andM is one equivalent of an alkali metal ion or alkaline earth metal ion,thereby to obtain a phenyl ether intermediate, and then subjecting the phenyl ether intermediate to an acid hydrolysis. The products are useful as intermediates in the synthesis of fungicides.Type: GrantFiled: December 11, 1981Date of Patent: July 17, 1984Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4439623Abstract: There is disclosed an improved process for the preparation of monochloroacetone by reacting acetone and chlorine in a vapor-liquid phase reactor and passing the reactor effluent through a fractionator to remove the liquid phase consisting mainly of monochloroacetone (MCA). The fractionator vapor phase effluent is consisting of acetone, hydrogen chloride, some monochloroacetone, and some reaction by-products sequentially fractionated in a series of condensers of varying temperatures such that the hydrogen chloride is isolated free of impurities and the remaining reaction materials, consisting mainly of acetone with some dissolved hydrogen chloride are available for recycling back into the reactor. The hydrogen chloride, isolated in the vapor phase, may be quenched with water to produce concentrated aqueous hydrochloric acid which may be used in other chemical procedures or it may be compressed into anhydrous hydrogen chloride.Type: GrantFiled: October 5, 1981Date of Patent: March 27, 1984Assignee: Merck & Co., Inc.Inventors: Kenneth H. Krieger, Lawrence J. Naldi, Carlos B. Rosas, Vijay Samant
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Patent number: 4426321Abstract: This invention discloses a number of novel odorant alkadienyl ketones, alcohols and oximes having from 9 to 15 carbon atoms, processes for making same and odorant compositions containing same.Type: GrantFiled: July 24, 1981Date of Patent: January 17, 1984Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4423243Abstract: A process for the production of 2,2-dimethyl-3-vinyl-cyclopropanecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 is a hydrogen atom, an alkyl group or a radical of an alcohol which can be used in pyrethroids, andX.sup.1 and X.sup.2 each independently is a halogen atomor a fluorine-substituted alkyl radical, comprising adding (a) a polyhalogenoalkene of the formula ##STR2## in which X.sup.3 and X.sup.4 each independently is a halogen atom, to 1-chloro-3,3-dimethyl-pent-4-en-2-one of the formula ##STR3## in the presence of a catalyst which yields free radicals, or in the presence of a metal salt of the VIII main group or of the sub-group IVa, VIIa or Ib of the periodic system, thereby to obtain a mixture of compounds of the formula ##STR4## and (b) reacting either or both of such compounds with a base of a formula(R.sup.1 --O.sup..crclbar.).sub.n M.sup.n+in whichM is an alkali metal or alkaline earth metal, andn is 1 or 2.Type: GrantFiled: December 16, 1981Date of Patent: December 27, 1983Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt
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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: 4328363Abstract: Halogen-substituted olefin addition compounds that contain a carbonyl group are formed by oxidatively adducting an olefin and a carbonyl compound such as a ketone, aldehyde, or ester. The method consists of reacting the olefin and the carbonyl component, in solution, with an oxidizing ion of manganese, cerium or vanadium in the presence of fluoride, chloride or bromide ion. This ionic component is incorporated in the adduct and appears on the olefin-derived carbon atom gamma to the carbonyl group. The gamma halogen substituted adducts are readily converted to cyclopropane derivatives, including pyrethroid intermediate compounds.Type: GrantFiled: November 8, 1978Date of Patent: May 4, 1982Assignee: Mobil Oil CorporationInventors: El-Ahmadi I. Heiba, Ralph M. Dessau
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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