Halogen Containing Reactant Patents (Class 568/393)
  • Patent number: 8552222
    Abstract: 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: Grant
    Filed: March 2, 2010
    Date of Patent: October 8, 2013
    Assignee: Syngenta Crop Protection LLC
    Inventors: David Anthony Jackson, Florian Schleth, Devender Singh Negi, Werner Pfaff
  • Publication number: 20120095265
    Abstract: 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: Application
    Filed: March 2, 2010
    Publication date: April 19, 2012
    Applicant: SYNGENTA CROP PROTECTION, LLC
    Inventors: David Anthony Jackson, Florian Schleth, Devender Singh Negi, Werner Pfaff
  • Patent number: 7795474
    Abstract: 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: Grant
    Filed: April 3, 2008
    Date of Patent: September 14, 2010
    Assignee: T. Hasegawa Co., Ltd.
    Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Norio Miyazawa, Tomoko Maeda
  • Publication number: 20100137648
    Abstract: 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: Application
    Filed: April 3, 2008
    Publication date: June 3, 2010
    Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Norio Miyazawa, Tomoko Maeda
  • Patent number: 7456322
    Abstract: 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: Grant
    Filed: May 17, 2005
    Date of Patent: November 25, 2008
    Assignee: Dow Global Technologies Inc.
    Inventor: Clark S. Davis
  • Patent number: 7060859
    Abstract: 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: Grant
    Filed: June 6, 2005
    Date of Patent: June 13, 2006
    Assignee: Council of Scientific and Industrial Research
    Inventors: Francois Figueras, Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Vattipally Neeraja, Kottapalli Koteswara Rao
  • Patent number: 7030280
    Abstract: 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: Grant
    Filed: August 24, 2004
    Date of Patent: April 18, 2006
    Assignee: Central Glass Company, Limited
    Inventors: Kazumasa Funabiki, Hitoshi Yamamoto, Masashi Nagamori, Masaki Matsui
  • Patent number: 7005551
    Abstract: 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: Grant
    Filed: March 8, 2005
    Date of Patent: February 28, 2006
    Inventor: John Stauffer
  • Patent number: 6969776
    Abstract: 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: Grant
    Filed: June 17, 2004
    Date of Patent: November 29, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6933413
    Abstract: 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: Grant
    Filed: July 2, 2002
    Date of Patent: August 23, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
  • Patent number: 6933414
    Abstract: 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: Grant
    Filed: June 21, 2004
    Date of Patent: August 23, 2005
    Inventor: John E. Stauffer
  • Patent number: 6803488
    Abstract: 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: Grant
    Filed: February 26, 2003
    Date of Patent: October 12, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Publication number: 20040186322
    Abstract: 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: Application
    Filed: January 9, 2004
    Publication date: September 23, 2004
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
  • Publication number: 20040024256
    Abstract: The present invention provides a process and apparatus for selectively halogenating a ketone of the formula (I) 1
    Type: Application
    Filed: July 1, 2002
    Publication date: February 5, 2004
    Inventor: Dennis E. Jackman
  • Patent number: 6455728
    Abstract: 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: Grant
    Filed: November 1, 1999
    Date of Patent: September 24, 2002
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William Jack Casteel, Jr., Wade H. Bailey, III
  • Publication number: 20020010372
    Abstract: 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: Application
    Filed: July 17, 2001
    Publication date: January 24, 2002
    Inventors: Ryo Nadano, Yoshihiko Goto
  • Patent number: 6307105
    Abstract: 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: Grant
    Filed: July 19, 2000
    Date of Patent: October 23, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William Jack Casteel, Jr., Robert George Syvret, Wade Hampton Bailey, III
  • Patent number: 6300522
    Abstract: 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: Grant
    Filed: November 29, 2000
    Date of Patent: October 9, 2001
    Assignee: Avecia Limited
    Inventors: John Crosby, Kevin Douglas Bailey, Michael John Monteith
  • Patent number: 6288281
    Abstract: 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: Grant
    Filed: November 16, 2000
    Date of Patent: September 11, 2001
    Assignee: UOP LLC
    Inventors: Laszlo T. Nemeth, Jeffery C. Bricker, Jennifer S. Holmgren, Lyle E. Monson
  • Patent number: 6252120
    Abstract: 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: Grant
    Filed: October 9, 1996
    Date of Patent: June 26, 2001
    Assignee: Haarmann & Reimer GmbH
    Inventors: Erich Dilk, Peter Wörner
  • Patent number: 6225506
    Abstract: 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: Grant
    Filed: December 13, 1999
    Date of Patent: May 1, 2001
    Assignee: Boulder Scientific Company
    Inventor: Jeffrey M. Sullivan
  • Patent number: 6121500
    Abstract: 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: Grant
    Filed: March 4, 1999
    Date of Patent: September 19, 2000
    Assignee: Albemarle Corporation
    Inventor: Mahmood Sabahi
  • Patent number: 6020502
    Abstract: A method for the fluorination of 1,3-diketones and 1,3-ketoesters is disclosed.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: February 1, 2000
    Assignee: BNFL Fluorochemicals Ltd.
    Inventors: Richard D. Chambers, John Hutchinson, Martin P. Greenhall, John S. Moilliet, Julie Thomson
  • Patent number: 5786515
    Abstract: 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: Grant
    Filed: August 30, 1996
    Date of Patent: July 28, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Ulf H. Dolling, Lisa F. Frey, Richard D. Tillyer, David M. Tschaen
  • Patent number: 5736274
    Abstract: 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: Grant
    Filed: April 18, 1997
    Date of Patent: April 7, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Teruo Umemoto, Kenji Adachi, Ginjiro Tomizawa, Sumi Ishihara, Masayuki Nagayoshi
  • Patent number: 5703248
    Abstract: The present invention concerns a novel process for the selective trihalogenation of ketones employing organic halogen salts.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: December 30, 1997
    Inventors: Jeffrey S. Rommel, James T. Traxler, Richard R. Boettcher
  • Patent number: 5569778
    Abstract: 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: Grant
    Filed: April 28, 1995
    Date of Patent: October 29, 1996
    Assignee: Daikin Industries Ltd.
    Inventors: Teruo Umemoto, Ginjiro Tomizawa
  • Patent number: 5449801
    Abstract: 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: Grant
    Filed: July 14, 1993
    Date of Patent: September 12, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Chris S. Barnum, Charles T. Blaisdell
  • Patent number: 5391811
    Abstract: .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: Grant
    Filed: November 3, 1993
    Date of Patent: February 21, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Bohm, Albrecht Marhold
  • Patent number: 5231205
    Abstract: 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: Grant
    Filed: September 23, 1991
    Date of Patent: July 27, 1993
    Assignee: Board of Regents of the University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5231232
    Abstract: 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: Grant
    Filed: December 18, 1991
    Date of Patent: July 27, 1993
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 5124486
    Abstract: 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: Grant
    Filed: April 19, 1991
    Date of Patent: June 23, 1992
    Assignee: Shell Research Limited
    Inventor: Paul H. Briner
  • Patent number: 4992577
    Abstract: 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: Grant
    Filed: May 22, 1989
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4740612
    Abstract: 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: Grant
    Filed: February 5, 1986
    Date of Patent: April 26, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Matsuo, Nobushige Itaya, Osamu Magara
  • Patent number: 4734524
    Abstract: 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: Grant
    Filed: August 16, 1982
    Date of Patent: March 29, 1988
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Paul L. Guss, James H. Tumlinson, III, Philip E. Sonnet, Adron T. Proveaux
  • Patent number: 4705650
    Abstract: 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: Grant
    Filed: July 10, 1985
    Date of Patent: November 10, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4686291
    Abstract: 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: Grant
    Filed: November 26, 1985
    Date of Patent: August 11, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hans-Ludwig Elbe
  • Patent number: 4642385
    Abstract: 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: Grant
    Filed: November 19, 1985
    Date of Patent: February 10, 1987
    Assignee: Mobay Corporation
    Inventor: Dennis E. Jackman
  • Patent number: 4634778
    Abstract: 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: Grant
    Filed: November 16, 1984
    Date of Patent: January 6, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel, Pierre Chabardes
  • Patent number: 4602117
    Abstract: 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: Grant
    Filed: November 6, 1985
    Date of Patent: July 22, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 4579974
    Abstract: 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: Grant
    Filed: December 7, 1984
    Date of Patent: April 1, 1986
    Assignee: ATOCHEM
    Inventors: Bernard Cheminal, Henri Mathais
  • Patent number: 4524221
    Abstract: 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: Grant
    Filed: February 22, 1983
    Date of Patent: June 18, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
  • Patent number: 4465863
    Abstract: 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: Grant
    Filed: November 12, 1982
    Date of Patent: August 14, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz, Marie R. Hanna
  • Patent number: 4460793
    Abstract: 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: Grant
    Filed: December 11, 1981
    Date of Patent: July 17, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
  • Patent number: 4439623
    Abstract: 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: Grant
    Filed: October 5, 1981
    Date of Patent: March 27, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Kenneth H. Krieger, Lawrence J. Naldi, Carlos B. Rosas, Vijay Samant
  • Patent number: 4426321
    Abstract: 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: Grant
    Filed: July 24, 1981
    Date of Patent: January 17, 1984
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4423243
    Abstract: 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: Grant
    Filed: December 16, 1981
    Date of Patent: December 27, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt
  • Patent number: 4385185
    Abstract: 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: Grant
    Filed: March 20, 1981
    Date of Patent: May 24, 1983
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Walter Hafner
  • Patent number: 4328363
    Abstract: 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: Grant
    Filed: November 8, 1978
    Date of Patent: May 4, 1982
    Assignee: Mobil Oil Corporation
    Inventors: El-Ahmadi I. Heiba, Ralph M. Dessau
  • Patent number: 4310702
    Abstract: 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: Grant
    Filed: July 28, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic