Halogen Containing Patents (Class 568/639)
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Patent number: 5117002Abstract: 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: GrantFiled: January 14, 1991Date of Patent: May 26, 1992Assignee: Occidental Chemical CorporationInventors: Robert A. Buchanan, Jeffrey S. Stults
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Patent number: 5110983Abstract: 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: GrantFiled: March 22, 1990Date of Patent: May 5, 1992Assignee: Hoechst AktiengesellschaftInventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
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Patent number: 5081316Abstract: 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: GrantFiled: December 27, 1989Date of Patent: January 14, 1992Assignee: Ethyl CorporationInventor: Saadat Hussain
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Patent number: 5081273Abstract: This invention relates to a process for the preparation of insecticidally active compounds and to novel styrene derivatives useful as intermediates therein.Type: GrantFiled: November 30, 1989Date of Patent: January 14, 1992Assignee: Imperial Chemical Industries plcInventors: Michael J. Bushell, Ralph A. Raphael
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Patent number: 5077440Abstract: 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: GrantFiled: October 23, 1989Date of Patent: December 31, 1991Assignee: Bromine Compounds Ltd.Inventors: Michael Zviely, Aaron R. McMurray, Joshua Hermolin
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Patent number: 5055235Abstract: 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: GrantFiled: December 12, 1990Date of Patent: October 8, 1991Assignee: Ethyl CorporationInventors: David R. Brackenridge, William T. Murray
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Patent number: 5000879Abstract: 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: GrantFiled: August 1, 1989Date of Patent: March 19, 1991Assignee: Ethyl CorporationInventors: Robert M. Moore, Jr., David R. Brackenridge
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Patent number: 4992593Abstract: 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: GrantFiled: November 23, 1988Date of Patent: February 12, 1991Assignee: Hoechst AktiengesellschaftInventor: Gunter Siegemund
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Patent number: 4990621Abstract: 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: GrantFiled: May 30, 1989Date of Patent: February 5, 1991Assignee: Hoechst AktiengesellschaftInventors: Hans H. Schubert, Gerhard Salbeck, Walter Luders, Werner Knauf, Anna Waltersdorfer
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Patent number: 4939172Abstract: 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: GrantFiled: February 8, 1988Date of Patent: July 3, 1990Assignee: Roussel UclafInventors: Joseph Cadiergue, Jacques Demassey, Jean-Pierre Demoute, Jean Tessier
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Patent number: 4918242Abstract: 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: GrantFiled: June 12, 1989Date of Patent: April 17, 1990Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4911754Abstract: 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: GrantFiled: July 16, 1987Date of Patent: March 27, 1990Assignee: American Cyanamid CompanyInventors: David A. Hunt, James A. Schwindeman
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Patent number: 4900758Abstract: 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: GrantFiled: May 11, 1989Date of Patent: February 13, 1990Assignee: ICI Americas Inc.Inventor: Karl J. Fisher
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Patent number: 4892975Abstract: 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: GrantFiled: September 28, 1987Date of Patent: January 9, 1990Assignee: President and Fellows of Harvard CollegeInventors: Thomas X. Neenan, George M. Whitesides
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Optically active compound, process for producing same and liquid crystal composition containing same
Patent number: 4873018Abstract: 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: GrantFiled: October 27, 1987Date of Patent: October 10, 1989Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri -
Patent number: 4871882Abstract: 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: GrantFiled: October 13, 1987Date of Patent: October 3, 1989Assignee: Bromine Compounds LimitedInventors: Hyman Stollar, Khaim Khariton, Mark Grinberg, Eva Ellmann
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Patent number: 4864027Abstract: 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: GrantFiled: June 22, 1988Date of Patent: September 5, 1989Assignee: Hoechst AktiengesellschaftInventors: Hans H. Shubert, Gerhard Salbeck, Walter Luders, Werner Knauf
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Patent number: 4859747Abstract: 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: GrantFiled: May 24, 1988Date of Patent: August 22, 1989Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
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Patent number: 4849547Abstract: 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: GrantFiled: October 13, 1987Date of Patent: July 18, 1989Assignee: Bromine Compounds LimitedInventors: Hyman Stollar, Khaim Khariton, Mark Grinberg, Eva Ellmann
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Patent number: 4847428Abstract: 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: GrantFiled: November 18, 1987Date of Patent: July 11, 1989Assignee: China Technical Consultants, Inc.Inventor: Jen-Tau Gu
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Patent number: 4835322Abstract: 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: GrantFiled: October 19, 1987Date of Patent: May 30, 1989Assignee: Great Lakes Chemical CorporationInventors: Rastko I. Mamuzic, Bhabatosh Bhattacharya
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Patent number: 4814340Abstract: 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: GrantFiled: November 6, 1986Date of Patent: March 21, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Nakatani Kiyoshi, Satoshi Numata, Kenji Kodaka, Kengo Oda, Shiro Shiraishi, Takatoshi Udagawa
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Patent number: 4808762Abstract: 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: GrantFiled: September 9, 1987Date of Patent: February 28, 1989Assignee: FMC CorporationInventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
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Patent number: 4791139Abstract: 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: GrantFiled: February 25, 1987Date of Patent: December 13, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4788349Abstract: Compounds of the Formula: ##STR1## wherein X is selected from bromine and chlorine useful as intermediates in the preparation of insecticidal compounds.Type: GrantFiled: May 22, 1987Date of Patent: November 29, 1988Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4778933Abstract: 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: GrantFiled: July 15, 1987Date of Patent: October 18, 1988Assignee: Ethyl CorporationInventors: Bonnie G. McKinnie, Meng-Sheng Ao
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Patent number: 4772633Abstract: 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: GrantFiled: February 20, 1986Date of Patent: September 20, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
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Patent number: 4766253Abstract: 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: GrantFiled: May 4, 1987Date of Patent: August 23, 1988Assignee: Ciba-Geigy CorporationInventor: Peter Rauber
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Patent number: 4755567Abstract: 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: GrantFiled: October 27, 1986Date of Patent: July 5, 1988Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
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Patent number: 4744812Abstract: 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: GrantFiled: March 4, 1985Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Bruno Wuerzer, Gerhard Hamprecht
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Patent number: 4743622Abstract: 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: GrantFiled: February 11, 1986Date of Patent: May 10, 1988Assignee: Schering AktiengesellschaftInventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
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Patent number: 4740629Abstract: 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: GrantFiled: July 6, 1987Date of Patent: April 26, 1988Assignee: Ethyl CorporationInventors: David R. Brackenridge, Bonnie G. McKinnie
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Patent number: 4731450Abstract: 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: GrantFiled: May 21, 1986Date of Patent: March 15, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Claude Wakselman, Marc Tordeux
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Patent number: 4717776Abstract: 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: GrantFiled: April 21, 1986Date of Patent: January 5, 1988Assignee: Ethyl CorporationInventors: David R. Brackenridge, Bonnie G. McKinnie
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Patent number: 4716251Abstract: 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: GrantFiled: February 7, 1986Date of Patent: December 29, 1987Assignee: Ethyl CorporationInventors: Gerald L. Scymanski, Amgad S. Mossaad, Saadat Hussain
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Patent number: 4709100Abstract: 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: GrantFiled: March 10, 1986Date of Patent: November 24, 1987Assignee: Bromine Compounds Ltd.Inventors: Joshua Hermolin, Arieh Kampf
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Patent number: 4701564Abstract: 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: GrantFiled: July 3, 1986Date of Patent: October 20, 1987Assignee: AtochemInventors: Robert Decaudin, Bernard Gurtner, Andre Gagnieur
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Patent number: 4701563Abstract: 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: GrantFiled: March 20, 1986Date of Patent: October 20, 1987Assignee: Schering AktiengesellschaftInventors: Heinrich Franke, Hartmut Joppien, Helga Franke
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Patent number: 4695657Abstract: 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: GrantFiled: December 17, 1985Date of Patent: September 22, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4668830Abstract: 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: GrantFiled: December 17, 1985Date of Patent: May 26, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4659021Abstract: 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: GrantFiled: October 25, 1985Date of Patent: April 21, 1987Assignee: Ethyl CorporationInventors: Wendell G. Bark, John C. Parks
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Patent number: 4638099Abstract: 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: GrantFiled: January 23, 1986Date of Patent: January 20, 1987Assignee: Rohm GmbHInventors: Achim Riemann, Werner Ude
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Patent number: 4575571Abstract: 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: GrantFiled: June 22, 1984Date of Patent: March 11, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Michel Desbois, Camille Disdier
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Patent number: 4564712Abstract: 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: GrantFiled: November 23, 1983Date of Patent: January 14, 1986Assignee: Hoechst AktiengesellschaftInventors: Herbert Kuckertz, Georg Schaeffer
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Patent number: 4533777Abstract: 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: GrantFiled: August 13, 1979Date of Patent: August 6, 1985Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Erich Klauke
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Patent number: 4526711Abstract: 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: GrantFiled: September 9, 1983Date of Patent: July 2, 1985Assignee: R. P. Cargille Laboratories, Inc.Inventors: Robert L. Sacher, William J. Sacher
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Patent number: 4521633Abstract: 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: GrantFiled: May 19, 1983Date of Patent: June 4, 1985Assignee: The Dow Chemical CompanyInventor: Joseph J. Pedjac
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Patent number: 4502973Abstract: 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: GrantFiled: February 3, 1983Date of Patent: March 5, 1985Assignee: National Research Development CorporationInventor: James E. Stangroom
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Patent number: 4484008Abstract: 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: GrantFiled: September 30, 1982Date of Patent: November 20, 1984Assignee: PPG Industries, Inc.Inventors: James A. Cook, Jr., James A. Manner
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Patent number: 4476328Abstract: 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: GrantFiled: November 12, 1981Date of Patent: October 9, 1984Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Masaaki Takahashi, Takashi Yamauchi