Halogen Containing Patents (Class 568/655)
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5105021
    Abstract: A higher yield of the difluorohalomethoxybenzene produced by the reaction of a metal phenolate with dibromodifluoromethane or bromochlorodifluoromethane can be obtained by conducting the addition of a metal alcoholate or a metal hydride as a reaction initiator to a solution or a suspension of an aprotic polar solvent containing the metal phenolate and dibromodifluoromethane or bromochlorodifluoromethane.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: April 14, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
  • Patent number: 5093526
    Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetra-alkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; reacting the 2-phenoxy ethyl chloride with n-propylamine at a temperature of from 50.degree. C. to 150.degree. C. optionally in the presence of a solvent to form N-n-propyl-N-2-phenoxy-ethyl amine; selectively chlorinating N-n-propyl-N-2-phenoxyethyl amine with chlorine in the presence of a solvent; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine formed.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: March 3, 1992
    Assignee: Makhteshim Chemical Works Ltd.
    Inventors: Joseph Sharvit, Abraham A. Pereferkovich
  • Patent number: 5091577
    Abstract: N-n-propyl-N-(2,4,6-trichlorophenoxy)-ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; selectively chlorinating the 2-phenoxy ethyl chloride with chlorine at a temperature from 0.degree. C. to 60.degree. C. in the presence of a catalytic amount if urea to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride; reacting the 2-(2,4,6-trichlorophenoxy)-ethyl chloride with n-propyl amine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethyl amine formed.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: February 25, 1992
    Assignee: Makhteshim Chemical Works Ltd.
    Inventors: Joseph Sharvit, Abraham A. Pereferkovich
  • Patent number: 5091578
    Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethylamine is prepared by selectively chlorinating 2-phenoxy ethanol by reacting it with chlorine either in the presence of hydrogen chloride at a temperature of from -10.degree. C. to 50.degree. C. or in the presence of urea at a temperature of from 20.degree. C. to 55.degree. C. in a water/carbon tetrachloride solvent mixture to form 2-(2,4,6-trichlorophenoxy)ethanol; reacting the 2-(2,4,6-trichlorophenoxy)ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium chloride, optionally in the presence of a solvent to form 2-(2,4,6-trichlorophenoxy)ethyl chloride; and reacting the 2-(2,4,6-trichlorophenoxy) ethyl chloride with n-propylamine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water to form N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: February 25, 1992
    Assignee: Makhteshim Chemical Works Ltd.
    Inventors: Joseph Sharvit, Abraham A. Pereferkovich, Daniel Shohat
  • Patent number: 5068461
    Abstract: The invention provides insecticidally active compounds of formula I: ##STR1## wherein A is selected from oxygen and a group of formula S(O).sub.n, where n represents 0, 1 or 2; W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms, selected from alkylene and alkylenedioxy; Y represents a substituted aryl group where each substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; Z represents a fluoroalkyl group of up to two carbon atoms; and either X' represents hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and acyloxy, or X and X' together represent a second bond between the adjacent carbon atoms.The invention also provides processes and intermediates useful for the preparation of the compounds of formula I, insecticidal compositions comprising the compounds of formula I, and methods of combating and controlling pests therewith.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: November 26, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 5068465
    Abstract: This invention relates to novel 3-aryl-2-fluoro-1-olefins and their pharmacological use as dopamine beta-hydroxylase DBH inhibitors in the treatment of DBH mediated conditions such as hypertension.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: November 26, 1991
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: James R. McCarthy, Charlotte L. Barney, Donald P. Matthews
  • Patent number: 5012004
    Abstract: An insecticidal and/or acaricidal composition which comprises as an active ingredient an insecticidally and/or acaricidally effective amount of at least one ether compound of the formula: ##STR1## wherein X.sub.1 is a hydrogen atom, a halogen atom, a lower alkyl group, a halo(lower)alkyl group, a phenoxyphenoxy(lower)alkyl group, a lower alkoxy group, a halo(lower)alkoxy group, a phenyl group, a halo(lower)alkoxyphenyl group, a methylenedioxy group or a group of the formula: ##STR2## (in which ##STR3## is a 6-membered unsaturated ring, X.sub.2 is a hydrogen atom, a halogen atom or a halo(lower)alkoxy group, Y.sub.2 is a hydrogen atom or combined with Y.sub.1 to form a direct single bond, n is an integer of 1 or 2 and X is an oxygen atom, a sulfur atom, a carbonyl group or a group of the formula: --C(R.sub.3)(R.sub.4)-- (in which R.sub.3 and R.sub.4 are each a hydrogen atom or a lower alkyl group));Y.sub.1 is a hydrogen atom or combined with Y.sub.2 to form a direct single bond;R.sub.1 and R.sub.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: April 30, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Sumio Nishida, Izumi Fujimoto, Yoshinori Shono, Hiroaki Fujimoto
  • Patent number: 4999429
    Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4996371
    Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine group in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and alkoxy-substituted halogenated aliphatic groups, wherein the method comprises the steps of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: February 26, 1991
    Assignee: BOC, Inc.
    Inventors: Donald F. Halpern, Mark L. Robin
  • Patent number: 4968836
    Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ruedi Kanel, John G. Dingwall
  • Patent number: 4960884
    Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: October 2, 1990
    Assignee: FMC Corporation
    Inventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
  • Patent number: 4956123
    Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: September 11, 1990
    Assignee: Nippon Oils & Fats Company, Ltd.
    Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
  • Patent number: 4950802
    Abstract: A novel method for the preparation of aryl trifluoromethyl ethers which comprises reacting a phenol, a perhalomethane, and an antimony pentahalide. For example, 4-nitrophenol may be reacted with an excess over stoichiometry of both carbon tetrachloride and antimony trifluoride with a catalytic amount of antimony pentachloride to form 4-nitrophenyl trifluoromethyl ether.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: August 21, 1990
    Assignee: The Dow Chemical Company
    Inventor: Bassam S. Nader
  • Patent number: 4940822
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, halo, halo-substituted alkyl, alkyl, cycloalkyl, aralkyl, aryl, heterocyclic, alkoxy, alkaryl, aryloxy, thioalkoxy, nitro, or N,N-dialkylamino are prepared by reacting 1-bromo-4-(trifluoromethyl)benzene with n-butyl lithium; reacting the product with a benzaldehyde of the formula: ##STR2## to produce a novel intermediate such as lithium 4-(trifluoromethyl)-.alpha.-]4-(trifluoromethyl)phenyl]benzenemethanol, and then reacting the lithium product with an acid or acid salt.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: July 10, 1990
    Assignee: Warner-Lambert Company
    Inventors: James G. Davidson, III, Brian S. Swierenga
  • Patent number: 4917817
    Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.
    Type: Grant
    Filed: July 21, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
  • Patent number: 4914244
    Abstract: Difluorochloromethoxybenzenes are prepared by reacting phenols with trichloromethyl chloroformate (=di-phosgene) in the presence of hydrogen fluoride.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: April 3, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Albrecht Marhold
  • Patent number: 4891450
    Abstract: The invention provides novel arylalkene compounds of formula I, a process for their preparation and their use as intermediates for insecticidal compounds, comprising, ##STR1## wherein W represents 1 to 4 substituents selected from halo, alkyl, alkoxy, haloalkyl, haloalkoxy and alkoxyalkyl, or W represents a bidentate alkylene or alkylenedioxy group linking adjacent carbon atoms, X represents fluoroalkyl, and Y is selected from chlorine, bromine and alkoxy; and a process for preparing said ethers. The compounds of formula I are prepared by reacting a ketone of formula: ##STR2## with a phosphonium salt of formula Hal.sup.- (Q).sub.3 P.sup.+ -CH.sub.2 -Y, where Hal.sup.- represents a halide ion and Q represents alkyl or aryl.
    Type: Grant
    Filed: January 25, 1988
    Date of Patent: January 2, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robin A. E. Carr, Lyn Powell
  • Patent number: 4876396
    Abstract: Phenolic compounds and mixtures thereof, e.g., admixture of 2,4-dichlorophenol and 2,6-dichlorophenol, are selectively chlorinated at a position ortho to a hydroxyl function thereof, by reacting such phenolic compound with gaseous chlorine, in a molten reaction medium, in the presence of a catalytically effective amount of a primary, secondary or tertiary amine.
    Type: Grant
    Filed: July 28, 1987
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Jean-Claude LeBlanc, Serge Ratton
  • Patent number: 4873018
    Abstract: An optically active 2-fluoro-1-alkanol compound represented by the formula (Ia): ##STR1## wherein R is an alkyl group having 1-16 carbon atoms, and C* is an asymmetric carbon atom; and an optically active compound derived from the fluoroalkanol and represented by the formula (Ib): ##STR2## wherein R and C* are the same as above, m is 1 or 2, n is 0 or 1, and A is a releasable substitutent. Because of the fluorine atom directly attached to an asymmetric carbon atom, these compounds are particularly effective in increasing a spontaneous polarization, improving a electric field responsive characteristic of a liquid crystal composition, and controlling the liquid crystal state.
    Type: Grant
    Filed: October 27, 1987
    Date of Patent: October 10, 1989
    Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri
  • Patent number: 4867903
    Abstract: A fluoroalkane derivative represented by the formula: ##STR1## wherein R denotes an alkyl group having 1-16 carbon atoms, C* denotes an asymmetric carbon atom, R.sup.1 denotes an alkyl or alkoxy group having 1-16 carbon atoms; ##STR2## respectively denote a phenylene group ##STR3## a cyclohexylene group ##STR4## or a pyrimidinylene group ##STR5## p is 0 or 1, q is 0 or 1 when p is 1, r is 0 or 1; and l, m and n are respectively 0 or a positive integer satisfying the relationship of l+m+n.gtoreq.1. The fluoroalkane derivative has a fluorine atom providing a large dipole moment and directly connected to an asymmetric carbon atom, so that it provides a high speed responsive characteristic through an increased spontaneous polarization when contained in a liquid crystal composition, especially a ferroelectric liquid crystal composition.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: September 19, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri
  • Patent number: 4831183
    Abstract: A process for the telomerization of a conjugated alkadiene with an organic hydroxy compound to produce an organo-oxyalkadiene is disclosed. A palladium catalyst having an ionic ligand is employed in a substantially oxygen-free environment in the presence of an aprotic polar solvent so that the reaction products may be separated from the catalyst by solvent extraction with a hydrocarbon solvent.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: May 16, 1989
    Assignee: National Distillers and Chemical Corporation
    Inventor: Ronnie M. Hanes
  • Patent number: 4828764
    Abstract: N-fluoro-N-perfluoromethyl sulfonamide compounds are provided as fluorinating agents for the fluorination of organic compounds by either the direct electrophilic fluorination of organic compounds or by the fluorination of organic compound carbanions.
    Type: Grant
    Filed: June 18, 1987
    Date of Patent: May 9, 1989
    Assignee: Research Corporation
    Inventor: Darryl D. DesMarteau
  • Patent number: 4816596
    Abstract: A process for preparing substituted or unsubstituted trifluoroethoxy- or trifluoroethylthiobenzenes by reaction of a phenol or thiophenol, both of which may be substituted or unsubstituted, with a compound of the formula CF.sub.3 --CH.sub.2 --O--R', where R' is a moiety selected from the group consisting of trifluoroacetyl, methanesulfonyl, paratoluenesulfonyl, trichloromethanesulfonyl and chlorosulfonyl, in the presence of a strong alkaline base and a complexing agent of the formula:N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (II)wherein n is an integer from 0 to 10 (0 is less than or equal to n is less than or equal to 10), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are selected from the group consisting of a hydrogen atom and an alkyl moiety having from 1 to 4 carbon atoms, and R.sub.5 denotes an alkyl or cycloalkyl moiety having from 1 to 12 carbon atoms, a phenyl moiety or a moiety of the formula: --C.sub.m H.sub.2m --C.sub.6 H.sub.
    Type: Grant
    Filed: March 28, 1986
    Date of Patent: March 28, 1989
    Assignee: Rhone-Polenc Specialites Chimoues
    Inventor: Bernard Langlois
  • Patent number: 4731450
    Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: March 15, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Claude Wakselman, Marc Tordeux
  • Patent number: 4727187
    Abstract: The present invention relates to a novel process for the preparation of an .alpha.,.alpha.-difluoroalkyl phenyl ether of formula I ##STR1## wherein R.sup.1 is hydrogen, halogen, amino, nitro, --SO.sub.2 --R.sup.4, --S--R.sup.5, --SO--R.sup.6 or --S--S--R.sup.7,R.sup.2 is hydrogen, halogen, nitro, hydroxy or --SO.sub.2 --R.sup.8,R.sup.3 is C.sub.1 -C.sub.5 haloalkyl,X is oxygen, sulfur, --SO-- or --SO.sub.2 --,R.sup.4 is hydroxy, halogen, amino, --N.dbd.C.dbd.O, --NH--CO--Cl, --NH--CO--Br, --NR.sup.9 R.sup.10, benzyl, phenyl, C.sub.1 -C.sub.4 alkyl or --NH'CO--NR.sup.11 R.sup.12,R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl, phenyl or benzyl,R.sup.7 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl,R.sup.8 is hydroxy or halogen,R.sup.9 and R.sup.10 are each independently of the other C.sub.1 -C.sub.4 alkyl or benzyl andR.sup.11 and R.sup.12 are each independently of the other hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: June 5, 1985
    Date of Patent: February 23, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Siegrist, Jean Indermuhle, Peter Baumeister
  • Patent number: 4714785
    Abstract: Organic haloformate, e.g., chloroformate, compounds are converted to their corresponding halides, e.g., chlorides, by heating the haloformate, e.g., between 90.degree. C. and 150.degree. C., in the presence of a catalytic amount of a carbon catalyst for a time sufficient to convert the haloformate to the corresponding halide.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: December 22, 1987
    Assignee: PPG Industries, Inc.
    Inventor: James A. Manner
  • Patent number: 4695657
    Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: September 22, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4690948
    Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: September 1, 1987
    Assignee: International Minerals & Chemical Corp.
    Inventor: Jing-Jong Lu
  • Patent number: 4678811
    Abstract: New substituted benzyl-type ethers of formula I ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkyl, phenyl-C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, halo-C.sub.2-4 -alkynyl, phenyl-C.sub.2-4 -alkynyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, phenyl-C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyloxy, halo-C.sub.2-4 -alkenyloxy, phenyl-C.sub.2-4 -alkenyloxy, C.sub.2-4 -alkynyloxy, halo-C.sub.2-4 -alkynyloxy, phenyl-C.sub.2-4 -alkynyloxy, alkylsulfonyloxy, haloalkylsulfonyloxy, arylsulfonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 -alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or one of these groups substituted by one or more of C.sub.1-6 -alkyl, halo-C.sub.1-6 -alkyl, phenyl-C.sub.1-6 -alkyl, C.sub.1-6 -alkyl interrupted by an O--, N-- or S-- atom, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: July 7, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
  • Patent number: 4668830
    Abstract: A process for the preparation of compounds containing a difluoromethylene or trifluoromethyl group. A compound containing a carbonyl group, preferbly an acid, acid halide, amide, ketone or any compound containing a perhaloalkylcarbonyl moiety is placed, in anhydrous liquid hydrofluoric acid, in contact with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group to a difluormethylene or trifluoromethyl group.The compounds obtained are useful as synthesis intermediates in the pharmaceutical, plant-protection and dye industries, as anesthetics or as heat-transfer and lubricating fluids.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: May 26, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4650910
    Abstract: Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.
    Type: Grant
    Filed: March 4, 1986
    Date of Patent: March 17, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
  • Patent number: 4631151
    Abstract: A fluorine-containing aromatic derivative is produced by causing a di(haloacyl)peroxide to react upon benzene, a mono-substituted benzene, naphthalene, or a mono-substituted naphthalene thereby introducing an X(CF.sub.2).sub.n -group into the benzene ring or the naphthalene ring.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: December 23, 1986
    Assignee: Nippon Oil & Fars Co., Ltd.
    Inventors: Michio Kobayashi, Masato Yoshida, Hideo Sawada, Hidehiko Hagii, Kazuyoshi Aoshima
  • Patent number: 4627933
    Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.
    Type: Grant
    Filed: July 7, 1983
    Date of Patent: December 9, 1986
    Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
  • Patent number: 4622431
    Abstract: Organic chloroformate compounds are decomposed to their corresponding chlorides by heating the chloroformate, e.g., between 100.degree. and 175.degree. C., in the presence of a catalytic amount of solid poly(vinylpyridine), e.g., poly(4-vinylpyridine), for a time sufficient to convert the chloroformate to the corresponding chloride.
    Type: Grant
    Filed: April 4, 1985
    Date of Patent: November 11, 1986
    Assignee: PPG Industries, Inc.
    Inventors: Robert G. Briody, Henry C. Stevens
  • Patent number: 4620040
    Abstract: Trifluoroanisoles of the formula ##STR1## where m is 1 or 2 and n is 0 to 3, are prepared by reacting hydrogen fluoride with trichloroanisoles of the formula ##STR2## in the vapor phase, in the presence of a fluorinated alumina catalyst whereinX is halogen other than fluorine;R is aryl, preferably 1 to 14 carbon atoms, halogen substituted aryl, halogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms;m is 1 or 2;n is 0 to 3;w is 0 to 2;p is 1 to 3;q is 0 to 2;w+p+q is 3;w' is 1 to 3 and is greater than w;p' is 0 to 2 and is less than p;q' is 0 to 2 and is equal to q; andw'+p'+q' is 3.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: October 28, 1986
    Assignee: Occidental Chemical Corporation
    Inventor: Derek J. Alsop
  • Patent number: 4607128
    Abstract: Novel compounds of the general formula ##STR1## in which X is hydrogen or chlorine, and each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently is hydrogen, methyl or ethyl, are useful intermediates in the preparation of the corresponding phenols. They may be prepared by treating a compound of the formula ##STR2## in which Hal is chlorine or fluorine, with a compound of the formulaHO--CHR.sup.1 --CR.sup.2 .dbd.CR.sup.3 R.sup.4in the presence of a base.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: August 19, 1986
    Assignee: Shell Oil Company
    Inventors: Paul H. Briner, Ronald F. Mason
  • Patent number: 4605784
    Abstract: Disclosed is a process for the preparation of ether-containing chlorides by reacting an ether-alcohol, ether-glycol or ether-polyglycol with a chlorinating agent such as thionyl chloride in the presence of a catalytic amount of a quaternary ammonium salt, the reaction being conducted at a temperature of about 25.degree. C. to about 90.degree. C.
    Type: Grant
    Filed: July 18, 1985
    Date of Patent: August 12, 1986
    Assignee: Eastman Kodak Company
    Inventors: Robert J. I. Eubanks, James G. Pacifici
  • Patent number: 4604243
    Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4600787
    Abstract: Aromatic compounds which contain perfluorinated side-chains bonded via a heteroatom are prepared by treating aromatic compounds, which contain side-chains which are perhalogenated, but only partially fluorinated, and bonded via heteroatom, with a catalyst capable of transferring halogen atoms.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: July 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Erich Klauke
  • Patent number: 4595763
    Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: June 17, 1986
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4582905
    Abstract: Convenient intermediates for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers, a reaction to the intermediates of the following formula and a conversion to obtain the said .beta.-blockers are disclosed. ##STR1## (wherein X is hydrogen or halogen; Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino;one of P and R combined together with Q represents lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy; hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen;and the remaining R or P is hydrogen or halogen;and dotted line represents the presence of one or two double bonds).
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: April 15, 1986
    Assignee: Shionogi & Co., Ltd.
    Inventor: Makiko Sakai
  • Patent number: 4575565
    Abstract: The invention herein pertains to a novel process for making substituted benzotrifluorides.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: March 11, 1986
    Assignee: Monsanto Company
    Inventor: William F. Goure
  • Patent number: 4558166
    Abstract: Process for the preparation of benzal chlorides from benzotrichlorides, according to which benzotrichlorides are reacted with thiols in the presence of metal salts at elevated temperatures.
    Type: Grant
    Filed: March 21, 1984
    Date of Patent: December 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Erich Klauke
  • Patent number: 4542243
    Abstract: The present invention relates to a process for producing 3-phenoxybenzyl 2-(4-alkoxyphenyl)-2-methylpropyl ethers having excellent insecticidal and acaricidal activities which are represented by formula (IV): ##STR1## wherein R is a lower alkyl group and X.sub.1 and X.sub.2 are each a hydrogen or fluorine atom, which comprises reacting a 3-halogeno-4-alkoxyneophyl halide represented by the formula (I): ##STR2## wherein Y.sub.1 and Y.sub.2 are each a hydrogen, chlorine or bromine atom, at least one of them being a chlorine or bromine atom, R has the same meaning as above and X is a halogen atom, with a 3-phenoxybenzyl alcohol represented by the formula (II): ##STR3## wherein X.sub.1 and X.sub.2 have the same meaning as above, in the presence of a base to obtain a 3-phenoxybenzyl 2-(4-alkoxy-3-halogenophenyl)-2-methylpropyl ether represented by the formula (III): ##STR4## wherein Y.sub.1, Y.sub.2, R, X.sub.1 and X.sub.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Mitsumasa Umemoto, Tamotsu Asano, Teruyuki Nagata, Satoshi Numata
  • Patent number: 4540522
    Abstract: This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: September 10, 1985
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Terry M. Balthazor
  • Patent number: 4495370
    Abstract: A process for the preparation of a 5-aryloxy-1-chloro-3,3-dimethyl-2-pentanone of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is halogen, alkyl having 1 to 4 carbon atoms, alkoxy or alkylthio each having 1 to 2 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each having 1 to 2 carbon atoms and 1 to 5 halogen atoms, cyclohexyl, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, nitro, cyano, alkoxy-carbonyl having 1 to 4 carbon atoms in the alkyl moiety, phenyl or halophenyl, m and n each independently is an integer from 0 to 5, and m+n.ltoreq.5,comprising reacting 1,1,5-trichloro-3,3-dimethyl-1-pentene of the formula ##STR2## with a phenol of the formula ##STR3## in the presence of a base in a diluent, to produce a compound of the formula ##STR4## and subjecting such reaction product to acid hydrolysis.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: January 22, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
  • Patent number: 4487960
    Abstract: Novel compounds of the following formula: ##STR1##
    Type: Grant
    Filed: April 19, 1982
    Date of Patent: December 11, 1984
    Assignee: The Upjohn Company
    Inventor: Chiu-Hong Lin
  • Patent number: 4476320
    Abstract: Ortho-substituted fluoroaromatic compounds are prepared by reaction of corresponding anilines, which are substituted in the o-position, with alkyl nitrites in the presence of alcohols and/or ethers and in the presence of boron trifluoride or boric acid esters and hydrogen fluoride, and by isolation and decomposition of the diazonium tetrafluoborate produced.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: October 9, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Diehl, Heinrich Pelster, Hubert Habetz
  • Patent number: H214
    Abstract: Substituted 1,1-difluoro(mono- or dihalo)ethoxybenzeneamines prepared by the reaction of a 1,1-difluoro(mono- or dihalo)ethylene and a substituted hydroxybenzeneamine in the presence of an alkali or alkaline earth metal hydroxide and a polar, aprotic solvent are isolated from the reaction mixture by a two stage distillation without prior dilution with water or other means of removal or neutralization of the alkali or alkaline earth metal hydroxides present. The products are useful intermediates in the preparation of insecticides and herbicides.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: February 3, 1987
    Inventor: John C. Little