Halogen Containing Patents (Class 568/639)
  • Patent number: 5117002
    Abstract: A process for the production of diaryl ethers which comprises heating, to a temperature of 80.degree. C. to 220.degree. C., a compound of the formula ##STR1## wherein X and Y are selected from the group consisting of H, CN, CO.sub.2 H, CHO, NO.sub.2, and CF.sub.3, provided that both X and Y may not simultaneously be H, in a solvent, in the presence of an inorganic base selected from the group consisting of the alkali metal carbonates, bicarbonates, and hydroxides, and in the presence of a catalyst selected from the group consisting of benzoic acid, substituted benzoic acids, C2-C4 aliphatic carboxylic acids, and alkali metal salts of said acids.
    Type: Grant
    Filed: January 14, 1991
    Date of Patent: May 26, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Robert A. Buchanan, Jeffrey S. Stults
  • Patent number: 5110983
    Abstract: Compounds of the formula I ##STR1## can be prepared by various process steps from 2-(4-methylphenyl)-2-hexafluoroisopropanol.Hexafluoroisopropyl-containing monomers are important starting compounds in the preparation of linear polycarboxamides and polycarboximides.
    Type: Grant
    Filed: March 22, 1990
    Date of Patent: May 5, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
  • Patent number: 5081316
    Abstract: This invention relates to a process for increasing the melting point of partially brominated diphenyl oxide mixtures having an average bromine content of 7.0 to 8.5. The process comprises: forming a slurry comprised of alkyl halide and the mixture; and evaporating essentially all of the allyl halide from the slurry.
    Type: Grant
    Filed: December 27, 1989
    Date of Patent: January 14, 1992
    Assignee: Ethyl Corporation
    Inventor: Saadat Hussain
  • Patent number: 5081273
    Abstract: This invention relates to a process for the preparation of insecticidally active compounds and to novel styrene derivatives useful as intermediates therein.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: January 14, 1992
    Assignee: Imperial Chemical Industries plc
    Inventors: Michael J. Bushell, Ralph A. Raphael
  • Patent number: 5077440
    Abstract: In a process for the preparation of 3-phenoxybenzylalcohol, 3-phenoxytoluene is reacted with dibromodimethylhydantoin in a non-polar solvent, followed by hydrolysis of the products of the first reaction step.The process provides highly pure 3-phenoxybenzylalcohol with high yields.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: December 31, 1991
    Assignee: Bromine Compounds Ltd.
    Inventors: Michael Zviely, Aaron R. McMurray, Joshua Hermolin
  • Patent number: 5055235
    Abstract: A process is disclosed for preparing a mixture of brominated, non-condensed ring polyaromatics, which process features multiple bromination temperatures and multiple catalyst additions for brominating the precursor non-condensed ring polyaromatic. The mixture has an average bromine number of about 6 to about 8 bromine atoms per molecule, a low melting point range, and a low amount of light end impurities.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: October 8, 1991
    Assignee: Ethyl Corporation
    Inventors: David R. Brackenridge, William T. Murray
  • Patent number: 5000879
    Abstract: This invention relates to a process for increasing the melting point of partially brominated diphenyl oxide mixtures having an average bromine content of 7.2 to 7.7. The process comprises: forming a slurry comprised of C.sub.1 -C.sub.4 alkanol and the mixture; maintaining the slurry until the melting point increase which is sought is obtained; and separating the so-treated mixture from the slurry.
    Type: Grant
    Filed: August 1, 1989
    Date of Patent: March 19, 1991
    Assignee: Ethyl Corporation
    Inventors: Robert M. Moore, Jr., David R. Brackenridge
  • Patent number: 4992593
    Abstract: A compound of the formula ##STR1## in which independently of one another R is equal to OH or lower alkyl having 1 to 4 carbon atoms, R' is equal to hydrogen or lower alkyl having 1 to 4 carbon atoms, processes for their preparation and their use as starting material in the preparation of partially fluorinated polycondensates.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: February 12, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Gunter Siegemund
  • Patent number: 4990621
    Abstract: New propene derivatives as intermediates for the preparation of pesticidal silane derivatives. Compounds of the formula ##STR1## wherein R.sup.4 is H, R.sup.5 is a radical of the formula ##STR2## and R.sup.17 is H or halogen are useful intermediates for the preparation of pesticidal silane derivatives.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: February 5, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans H. Schubert, Gerhard Salbeck, Walter Luders, Werner Knauf, Anna Waltersdorfer
  • Patent number: 4939172
    Abstract: Novel cyclopropane carboxylic acid esters of all possible stereoisomeric forms and mixtures thereof of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, fluorine, chlorine and bromine, R is selected from the group consisting of optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted, optionally unsaturated cycloalkyl of 3 to 8 carbon atoms optionally substituted, optionally substituted aryl of 6 to 14 carbon atoms and optionally substituted heterocycle, Z is selected from the group consisting of hydrogen, --CH.sub.3, --CN and --C.tbd.CH and Y is selected from the group consisting of hydrogen, --OH, optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted, --CN, --(CH.sub.2).sub.m --OAlk, --(CH.sub.2).sub.m --S--Alk, ##STR2## m is 0,1,2,3 or 4, Alk is alkyl of 1 to 12 carbon atoms, --Si(Alk').sub.3, Alk' is optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted, --O--Ar and --(CH.sub.2).sub.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: July 3, 1990
    Assignee: Roussel Uclaf
    Inventors: Joseph Cadiergue, Jacques Demassey, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4918242
    Abstract: A process for producing the optically pure (+)- or (-)-isomer of a phenyl- or substituted-phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4911754
    Abstract: This invention relates to aryloxy dihydrobenzofuran, oxoindole or benzofuranone derivatives having herbicidal activity and to the use of such compounds to control the growth of noxious plants, i.e., weeds.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: March 27, 1990
    Assignee: American Cyanamid Company
    Inventors: David A. Hunt, James A. Schwindeman
  • Patent number: 4900758
    Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, fluoro or trifluoromethyl;R.sub.2 is(a) halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 haloalkoxy if R.sub.1 is hydrogen or fluoro; or(b) hydrogen if R.sub.1 is trifluoromethyl;R.sub.3 is hydrogen or halogen; andR.sub.4 is hydrogen or mono- or poly-halogen.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 13, 1990
    Assignee: ICI Americas Inc.
    Inventor: Karl J. Fisher
  • Patent number: 4892975
    Abstract: The compound 1,3-diethynyl tetrafluorobenzene, and compounds having the structure ##STR1## represents a perfluorinated benzene ring and X represents oxygen or sulfur, as well as homopolymers and copolymers thereof.
    Type: Grant
    Filed: September 28, 1987
    Date of Patent: January 9, 1990
    Assignee: President and Fellows of Harvard College
    Inventors: Thomas X. Neenan, George M. Whitesides
  • 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: 4871882
    Abstract: A process for the preparation of Decabromodiphenyl ether is disclosed, which employs dibromomethane as the reaction medium, at temperatures not exceeding 80.degree. C.The product obtained by the process of the invention possesses improved thermal stability.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: October 3, 1989
    Assignee: Bromine Compounds Limited
    Inventors: Hyman Stollar, Khaim Khariton, Mark Grinberg, Eva Ellmann
  • Patent number: 4864027
    Abstract: The compounds of the formula (I) ##STR1## in which X denotes CH.sub.2, O, S or NR.sup.6,R.sup.1 denotes alkyl, cycloalkyl, alkenyl, (substituted) phenyl, or (substituted) naphthyl,R.sup.2 and R.sup.3 denote alkyl, alkenyl or phenyl, or R.sup.2 and R.sup.3 together denote an alkylene chain,R.sup.4 denotes --H, --CN, --CCl.sub.3, --C.tbd.CH, alkyl, F, or --C(S)--NH.sub.2,R.sup.5 denotes pyridyl, furyl, thienyl, phthalimidyl, di(C.sub.1 -C.sub.4)alkylmaleinimidyl, thiophthalimidyl, dihydrophthalimidyl or tetrahydrophthalimidyl, which may all be substituted, or substituted phenyl, orR.sup.4 and R.sup.5 --together with the carbon atom bridging them--denote an optionally substituted indanyl, cyclopentenoyl or cyclopentenyl radical,with the proviso that compounds of the formula I in whichR.sup.1 denotes phenyl which is substituted in the para-position by (C.sub.1 -C.sub.4)alkoxy, halogen or (C.sub.1 -C.sub.4)alkyl;R.sup.2 and R.sup.3 denote CH.sub.3 ;X denotes O;R.sup.4 denotes H andR.sup.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: September 5, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans H. Shubert, Gerhard Salbeck, Walter Luders, Werner Knauf
  • Patent number: 4859747
    Abstract: The direct fluorination of ethers in the presence of hydrogen fluoride (HF) scavengers such as sodium fluoride and potassium fluoride is disclosed. Ethers (liquid or solid) are either mixed with the HF scavenger, coated onto the HF scavenger or placed separately with the HF scavenger into a fluorination reactor and fluorinated by exposure to elemental fluorine. The HF scavenger permits use of more severe fluorination conditions than would be possible in the absence of the scavenger, i.e. higher initial fluorine, less gradual increases in fluorine gas concentrations and greater fluorine gas flow rates.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: August 22, 1989
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
  • Patent number: 4849547
    Abstract: A process for the preparation of decabromodiphenyl ether by the reaction of diphenyl ether or of a partially brominated derivative thereof, in a mixture of halogenated organic solvents is described.The process of the invention provides a product having improved thermal stability. The process can be carried out in a quasi-steady state manner, thereby producing a product with constant quality.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: July 18, 1989
    Assignee: Bromine Compounds Limited
    Inventors: Hyman Stollar, Khaim Khariton, Mark Grinberg, Eva Ellmann
  • Patent number: 4847428
    Abstract: A process for recrystallization of a brominated aromatic compound under pressure for purifying it from the contamination by bromine and hydrogen bromide, comprising the steps of: placing the brominated aromatic compound in a solvent or a combination of solvents selected from toluene, 1,dibromoethane, m-xylene, benzene, dichloromethane, chloroform, and 1,2-dichloroethane; adding into the resultant mixture a base or a combination of bases selected from pyridine, ethylene diamine, n-butylamine, tert-butylamaine, triethylamine, sodium ethoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, and sodium bicarbonate; and heating the resultant mixture to a temperature above the atmospheric boiling point and at a pressure above the vapor pressure of the resultant material at that temperature.
    Type: Grant
    Filed: November 18, 1987
    Date of Patent: July 11, 1989
    Assignee: China Technical Consultants, Inc.
    Inventor: Jen-Tau Gu
  • Patent number: 4835322
    Abstract: 4,4'-dibromodiphenyl ether may be obtained in high yield and purity by the uncatalyzed "neat" bromination of diphenyl oxide, followed by methanol digestion.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: May 30, 1989
    Assignee: Great Lakes Chemical Corporation
    Inventors: Rastko I. Mamuzic, Bhabatosh Bhattacharya
  • Patent number: 4814340
    Abstract: The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphtyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group, and R.sup.3 stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to processes for the preparation of these compounds and the uses of these compounds.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.
    Type: Grant
    Filed: November 6, 1986
    Date of Patent: March 21, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Nakatani Kiyoshi, Satoshi Numata, Kenji Kodaka, Kengo Oda, Shiro Shiraishi, Takatoshi Udagawa
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
  • Patent number: 4791139
    Abstract: A compound of formula: ##STR1## wherein W represents one or more 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 is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: December 13, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 4788349
    Abstract: Compounds of the Formula: ##STR1## wherein X is selected from bromine and chlorine useful as intermediates in the preparation of insecticidal compounds.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: November 29, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Alan J. Whittle
  • Patent number: 4778933
    Abstract: The process comprises: (a) initiating a feed of molten diphenyl oxide to a substantially anhydrous mixture of methylene dibromide solvent, elemental bromine (Br.sub.2) and an aluminum trihalide catalyst at a temperature between about 10.degree. and about 30.degree. C.; (b) heating the reaction mixture to about 50.degree.-60.degree. C., and while maintaining the temperature at about 50.degree.-60.degree. C., continuing the feed of molten diphenyl oxide until the total amount fed is equivalent to (i) about 0.064 to about 0.077 mole per mole of elemental bromine (Br.sub.2) employed in the reaction, and (ii) about 0.2 to about 10 parts by weight per part by weight of methylene dibromide employed in the reaction; (c) steam distilling the methylene dibromide solvent and the residual bromine from the reaction mixture; (d) recovering decabromodiphenyl oxide from the distilland; and (e) drying the methylene dibromide and bromine distillate to render them suitable for reuse in the process.
    Type: Grant
    Filed: July 15, 1987
    Date of Patent: October 18, 1988
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Meng-Sheng Ao
  • Patent number: 4772633
    Abstract: This invention relates to a novel compound represented by the following general formula (I), its production, and an insecticidal and acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: September 20, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
  • Patent number: 4766253
    Abstract: The invention relates to a novel process for preparing chlorodiphenyl ethers of the formula I ##STR1## in which R is hydrogen or chlorine, which comprises heating a material of the formula III ##STR2## in which X is one equivalent of an alkali metal or alkaline earth metal ion and R is as defined above, in an excess of a dichlorobenzene of the formula II ##STR3## in the presence of a copper catalyst and of an aprotic solvent as cocatalyst at temperatures of 120.degree.-220.degree. C.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: August 23, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Rauber
  • Patent number: 4755567
    Abstract: The direct fluorination of ethers in the presence of hydrogen fluoride (HF) scavengers such as sodium fluoride and potassium fluoride is disclosed. Ethers (liquid or solid) are either mixed with the HF scavenger, coated onto the HF scavenger or placed separately with the HF scavenger into a fluorination reactor and fluorinated by exposure to gradually increasing concentrations of fluorine gas. The HF scavenger permits use of more severe fluorination conditions i.e. higher initial fluorine, less gradual increases in fluorine gas concentrations and greater fluorine gas flow rates.
    Type: Grant
    Filed: October 27, 1986
    Date of Patent: July 5, 1988
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
  • Patent number: 4744812
    Abstract: Substituted diphenyl ethers of the formula ##STR1## where Z.sub.1, Z.sub.2 and Z.sub.3 are hydrogen, halogen, nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto, haloalkylmercapto, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl, Z.sub.4 is hydrogen, cyano, alkyl, alkoxy, acetoxy or alkylmercapto, Y is hydrogen, halogen, cyano or nitro, X is oxygen, sulfur, sulfinyl or sulfonyl, and A is hydrogen, unsubstituted or substituted alkyl ##STR2## and can also be sulfonyl ##STR3## when X is oxygen, and, when Z.sub.4 is alkoxy or alkylmercapto, can also be a methylene chain --(CH.sub.2).sub.m -- by which the radicals Z.sub.4 --CH--X-- are bonded to form a ring, R.sub.1 is hydrogen, methyl, ethyl or n-propyl, R.sub.2 is cyano, methoxy, ethoxy or ##STR4## where B is OH, ONa, O--alkyl, unsubstituted or substituted phenoxy, --NH.sub.2, --NH--alkyl or --N(alkyl).sub.2, n is 1, 2 or 3, R.sub.3 and R.sub.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Adolf Parg, Bruno Wuerzer, Gerhard Hamprecht
  • Patent number: 4743622
    Abstract: The invention relates to new aromatic alkane derivatives of the general formula ##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, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, 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 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: February 11, 1986
    Date of Patent: May 10, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
  • Patent number: 4740629
    Abstract: A process for partially brominating non-condensing ring aromatics (e.g. diphenyl ether) in the absence of a solvent by adding the polyaromatic to a stoichiometric excess of liquid bromine containing a zirconium halide catalyst. Product containing three bromine atoms per benzene ring (e.g., hexabromodiphenyl ether) is formed in high selectivity by keeping the reaction mixture below a threshold temperature at which higher bromine substitution occurs.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: April 26, 1988
    Assignee: Ethyl Corporation
    Inventors: David R. Brackenridge, Bonnie G. McKinnie
  • 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: 4717776
    Abstract: A process for partially brominating polyphenylene ether (e.g. diphenly ether) in the absence of a solvent by adding the polyphenylene ether to a stoichiometric excess of liquid bromine containing a zirconium halide catalyst.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: January 5, 1988
    Assignee: Ethyl Corporation
    Inventors: David R. Brackenridge, Bonnie G. McKinnie
  • Patent number: 4716251
    Abstract: Diaryloxyalkanes such as diphenoxyethane are brominated to give a product containing an average of about 5-7 bromine atoms per molecule by commingling a solution of the diaryloxyalkane in a haloalkane solvent with an excess of liquid bromine in the absence of a bromination catalyst.
    Type: Grant
    Filed: February 7, 1986
    Date of Patent: December 29, 1987
    Assignee: Ethyl Corporation
    Inventors: Gerald L. Scymanski, Amgad S. Mossaad, Saadat Hussain
  • Patent number: 4709100
    Abstract: The present invention relates to a process for the manufacture of mixtures of 3-phenoxybenzyl bromide and 3-pnenoxybenzal bromide using dibromodimethylhydantoin as brominating agent. According to the process, the reaction between the m-phenoxytoluene and the brominating agent is carried out in a non-polar solvent at temperatures above 65 degrees C. The molar ratio between the reactants is selected in the range of between 0.5:1 to 1.25:1 of the brominating agent towards the 3-phenoxytoluene. In a preferred embodiment, a radical initiator is incorporated being selected from the group consisting of ultraviolet rays and compounds containing azo-groups, peroxides or mixtures thereof. According to a most preferred embodiment the addition of the free radical and of the brominating agent is carried out gradually. The process is characterized by its very high yield, the products obtained being of a very high quality.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: November 24, 1987
    Assignee: Bromine Compounds Ltd.
    Inventors: Joshua Hermolin, Arieh Kampf
  • Patent number: 4701564
    Abstract: The invention relates to the preparation of brominated derivatives of diphenyl ether. This process includes preparing an underbrominated product and perbrominating the by-products of this reaction. This process is particularly suitable for the preparation of octabromodiphenyl ether and decabromodiphenyl ether.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: October 20, 1987
    Assignee: Atochem
    Inventors: Robert Decaudin, Bernard Gurtner, Andre Gagnieur
  • Patent number: 4701563
    Abstract: Difluorocyclopropane derivatives of the general formula I ##STR1## in which R.sub.1 is halogen, C.sub.1-4 -alkoxy, fluoro-substituted alkoxy, C.sub.1-4 -alkyl or trifluoromethyl,R.sub.2 is hydrogen or fluorine andn is 0, 1 or 2,are described, which have valuable insecticidal and acaricidal properties.
    Type: Grant
    Filed: March 20, 1986
    Date of Patent: October 20, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinrich Franke, Hartmut Joppien, Helga Franke
  • 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: 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: 4659021
    Abstract: A process for purifying crude brominated aromatic compounds such as decabromodiphenyl oxide containing impurities. The crude brominated aromatic compound undergoes a single processing step of grinding in the presence of heated air. The temperature is sufficient to effect substantial removal of impurities and yet remains below the melting point of the brominated aromatic compound.
    Type: Grant
    Filed: October 25, 1985
    Date of Patent: April 21, 1987
    Assignee: Ethyl Corporation
    Inventors: Wendell G. Bark, John C. Parks
  • Patent number: 4638099
    Abstract: A method for making 4,4'-dihydroxydiphenyl ether from diphenyl ether by oxidatively iodinating diphenyl ether to 4,4'-diiododiphenyl ether and/or 4-hydroxy-4'-iododiphenyl ether, hydrolyzing this product with a base, recovering iodine from the solution containing iodide, and recycling the iodine to the iodination step.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: January 20, 1987
    Assignee: Rohm GmbH
    Inventors: Achim Riemann, Werner Ude
  • Patent number: 4575571
    Abstract: A process for the stimulaneous halogenation and fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with the halogen in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: March 11, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4564712
    Abstract: Diphenyl ethers are prepared by Ullmann reaction of alkali metal phenolates with halobenzenes in the presence of basic copper carbonate and/or copper salts of lower aliphatic carboxylic acids as catalysts. These special catalysts have a better catalytic activity than other copper catalysts known for the Ullmann reaction.The diphenyl ethers prepared or obtainable according to the invention are mainly intermediates in diverse fields such as pharmaceuticals or plant protecting agents.
    Type: Grant
    Filed: November 23, 1983
    Date of Patent: January 14, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Kuckertz, Georg Schaeffer
  • Patent number: 4533777
    Abstract: A process for the preparation of an aromatic trifluoromethyl compound which comprises contacting an aromatic compound of the formula ##STR1## wherein R.sup.1 denotes hydrogen, alkyl, aryl, aralkyl, aryloxy, arylthio, polyhalogenoalkoxy or polyhalogenoalkylthio and the aromatic substituents R.sup.1 can in turn be substituted by halogen, alkyl, polyhalogenoalkyl, polyhalogenoalkoxy, polyhalogenoalkylthio, nitro, chlorocarbonyl or chlorosulfonyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, halogen or alkyl and two adjacent radicals of the group R.sup.1 to R.sup.5 can conjointly form a three-membered to five-membered alkylene radical, with carbon tetrachloride and hydrogen fluoride at a temperature in the range of 50.degree. C. to 140.degree. C. Certain new aromatic trifluoromethyl compounds which can prepared by such a process are also disclosed.
    Type: Grant
    Filed: August 13, 1979
    Date of Patent: August 6, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Erich Klauke
  • Patent number: 4526711
    Abstract: Formulations for use as mounting media in microscopy and also useful as optical coupling materials for fibers and lens systems having a wide range of refractive index between 1.58 to 1.73 and exhibiting a range in viscosity from a very viscous fluid to a semi-solid resin or melt. The material is selected from brominated diphenyl oxides and modified or unmodified alpha-methylstyrene polymers. These materials can be employed individually or blended together with a stabilizer to provide a host of materials having different refractive indexes within said range and useful in various optical systems.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: July 2, 1985
    Assignee: R. P. Cargille Laboratories, Inc.
    Inventors: Robert L. Sacher, William J. Sacher
  • Patent number: 4521633
    Abstract: Prepare high purity perbrominated aromatic compounds, especially decabromodiphenyl oxide, by adding an aromatic compound to a mixture comprising an organic solvent, a catalyst, and a slight stoichiometric excess of bromine, at a low initial reaction temperature.
    Type: Grant
    Filed: May 19, 1983
    Date of Patent: June 4, 1985
    Assignee: The Dow Chemical Company
    Inventor: Joseph J. Pedjac
  • Patent number: 4502973
    Abstract: Electroviscous (EV) fluids consisting of solid hydrophilic particles dispersed in hydrophobic liquids, where the liquid contains a diaryl derivative component of general formula I ##STR1## in which R is CY.sub.2,O,S,SO,SO.sub.2,SiF.sub.2, or O--SiY.sub.2 --O,X.sup.1 and X.sup.2 are halogens, (m+n) is between 1 and 3 on average, and (p+q) is between 0 and 1 on average. EV fluids containing these novel components possess generally improved properties in terms of lower viscosities, electrical conductivities, toxicities and freezing points. In a preferred embodiment, the component is a mixture of brominated diphenyl methanes in which R is CH.sub.2,n=O,X.sup.1 =Br,(m+n) is approximately one, and (p+q)=0.
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: March 5, 1985
    Assignee: National Research Development Corporation
    Inventor: James E. Stangroom
  • Patent number: 4484008
    Abstract: This invention relates to an improvement in the process of isolating certain diphenyl ethers from an aprotic organic solvent by the addition of a diphenyl ether phase forming amount of water to a reaction mixture comprising a liquid phase of the diphenyl ether dissolved in the solvent.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: November 20, 1984
    Assignee: PPG Industries, Inc.
    Inventors: James A. Cook, Jr., James A. Manner
  • Patent number: 4476328
    Abstract: A novel trifluoropropyl derivative of mono-substituted benzene represented by the general formula: ##STR1## wherein R is halogen atom, hydroxy, trifluoromethyl, n-octyl, n-dodecyl, or phenoxy group not substituted or mono-substituted by 3,3,3-trifluoropropyl group, and n is an integer of 1, 2 or 3, with the proviso that the total number of 3,3,3-trifluoropropyl group of the derivative of mono-substituted benzene is at most 3, and a process for producing the derivative of mono-substituted benzene.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: October 9, 1984
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Masaaki Takahashi, Takashi Yamauchi