Halogen Bonded Directly To The Benzene Ring Patents (Class 568/656)
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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: 4828764Abstract: 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: GrantFiled: June 18, 1987Date of Patent: May 9, 1989Assignee: Research CorporationInventor: Darryl D. DesMarteau
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Patent number: 4822927Abstract: Disclosed is a process for continuous preparation of aromatic fluorides wherein aromatic diazonium fluorides are continuously decomposed at low concentration in a reaction system of one or more continuous agitated reactors.Type: GrantFiled: November 24, 1987Date of Patent: April 18, 1989Assignee: Mallinckrodt, Inc.Inventors: Nickolas J. Stepaniuk, Bruce J. Lamb
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Patent number: 4816596Abstract: 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: GrantFiled: March 28, 1986Date of Patent: March 28, 1989Assignee: Rhone-Polenc Specialites ChimouesInventor: Bernard Langlois
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Patent number: 4783285Abstract: The nucleophilic substitution upon unactivated monocyclic or polycyclic aromatic or heteroaromatic substrates bearing suitable leaving groups can be achieved by catalyzing the substitution of said leaving groups by an anionic nucleophile with a cyclic or acyclic polydentate chelating ligand. Specific products of this reaction can be used in preparing sulfonylurea herbicides.Type: GrantFiled: February 3, 1987Date of Patent: November 8, 1988Assignee: E. I. DuPont de Nemours and CompanyInventor: Alden D. Josey
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Patent number: 4766243Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.Type: GrantFiled: August 10, 1984Date of Patent: August 23, 1988Assignee: Occidental Chemical CorporationInventor: Michael J. Fifolt
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Patent number: 4740630Abstract: A chiral phenylether compound having the formula ##STR1## wherein X is a halogen atom; m is an integer from 3 to 5, n is an integer from 3 to 12 and * designates an asymmetric carbon is disclosed. The chiral phenylether compounds are useful to prepare chiral smectic phase pyrimidine phenylether liquid crystal compounds of the formula. ##STR2## The reaction is carried by reacting (I) with butylithium, dissolving in ether and reacting with a 1-bromoalkane to yield (IV). Compounds (IV) are particularly well suited to broaden the useful temperature range of ferroelectric liquid crystal materials.Type: GrantFiled: December 19, 1986Date of Patent: April 26, 1988Assignee: Seiko Epson CorporationInventors: Yoshio Shionozaki, Toshihiro Shibata
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Patent number: 4739057Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.Type: GrantFiled: June 30, 1986Date of Patent: April 19, 1988Assignee: Stauffer Chemical Co.Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
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Patent number: 4730046Abstract: A process for selectively substituting an aromatic nitro group with a halo group which comprises contacting the nitroaromatic compound with a phosphorushalide of formula: R.sub.n PX.sub.5-n wherein n is selected from 0, 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of: straight and branched chain alkyl, alkoxy, and haloalkyl; halogen, sulfonate and mixtures thereof; and X is a halogen in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphosphorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture to maintain a temperature of from about 100.degree. C. to about 175.degree. C.Type: GrantFiled: April 14, 1986Date of Patent: March 8, 1988Assignee: Stauffer Chemical CompanyInventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
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Patent number: 4727187Abstract: 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: GrantFiled: June 5, 1985Date of Patent: February 23, 1988Assignee: Ciba-Geigy CorporationInventors: Urs Siegrist, Jean Indermuhle, Peter Baumeister
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Patent number: 4724269Abstract: A process for producing a p-chlorobenzene having the formula: ##STR1## wherein R is a lower alkyl group, a lower alkoxy group or a halogen atom, which comprises chlorinating a benzene having the formula: ##STR2## wherein R is as defined above, in a liquid phase in the presence of a catalyst, characterized in that the catalyst is a combination of an aliphatic alcohol having the formula:R'OH (III)wherein R' is a lower alkyl group or a lower haloalkyl group, and a zeolite having a SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 3 to 8 and a pore size of from 6 to 10 .ANG..Type: GrantFiled: June 18, 1986Date of Patent: February 9, 1988Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Toshihiro Suzuki, Chizu Komatsu
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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: 4683091Abstract: The nucleophilic substitution upon unactivated monocyclic or polycyclic aromatic or heteroaromatic substrates bearing suitable leaving groups can be achieved by catalyzing the substitution of said leaving groups by an anionic nucleophile with a cyclic or acyclic polydentate chelating ligand. Specific products of this reaction can be used in preparing sulfonylurea herbicides.Type: GrantFiled: September 9, 1985Date of Patent: July 28, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Alden D. Josey
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Patent number: 4678811Abstract: 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: GrantFiled: October 17, 1985Date of Patent: July 7, 1987Assignee: Schering AktiengesellschaftInventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
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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: 4654446Abstract: Alkylarylethers are produced according to the invention using phenols and ethers of aliphatic alcohols as the starting materials, in the presence of BPO.sub.4.Type: GrantFiled: February 27, 1986Date of Patent: March 31, 1987Assignee: Eniricerche S.p.A.Inventors: Maurizio Brunelli, Pierferdinando Ferrari, Fabrizio Stroppa, Giuseppe Bellussi
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Patent number: 4650910Abstract: 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: GrantFiled: March 4, 1986Date of Patent: March 17, 1987Assignee: Bayer AktiengesellschaftInventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
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Patent number: 4642349Abstract: Aromatic ethers or polyethers are prepared by reacting an organic halide such as a hydrocarbon halide with an aryl lower alkyl carbonate in the presence of an initiator.Type: GrantFiled: May 24, 1982Date of Patent: February 10, 1987Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4629814Abstract: This process relates to the preparation of unsubstituted or substituted bis-bromoalkyl ethers by reacting unsubstituted or substituted 1,3-dioxolane or unsubstituted or substituted 1,3-dioxane with thionyl bromide. The bis-bromoalkyl ethers made by this process can be used in preparing biologically active compounds.Type: GrantFiled: August 27, 1985Date of Patent: December 16, 1986Assignee: Rohm and Haas CompanyInventor: Michael P. James
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Patent number: 4621095Abstract: The invention relates to bis-azolyl-substituted t-butanol derivatives defined herein under formula (I) and their use as antimycotic agents. Included in the invention are compositions containing said t-butanol derivatives and methods for using said derivatives and compositions containing them for their antimycotic activity.Type: GrantFiled: August 11, 1983Date of Patent: November 4, 1986Assignee: Bayer AktiengesellschaftInventors: Erik Regel, Karl H. Buchel, Manfred Plempel
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Patent number: 4621160Abstract: A process for the chlorination of aromatic derivatives. The aromatic derivative is reacted with chlorine gas 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: November 4, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Michel Desbois, Camille Disdier
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Patent number: 4620040Abstract: 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: GrantFiled: March 18, 1985Date of Patent: October 28, 1986Assignee: Occidental Chemical CorporationInventor: Derek J. Alsop
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Patent number: 4607128Abstract: 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: GrantFiled: January 8, 1986Date of Patent: August 19, 1986Assignee: Shell Oil CompanyInventors: Paul H. Briner, Ronald F. Mason
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Patent number: 4598085Abstract: Novel compounds of the class of 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles having fungicidal and plant-growth regulating properties.Type: GrantFiled: January 21, 1982Date of Patent: July 1, 1986Assignee: Janssen Pharmaceutica N.V.Inventors: Jan Heeres, Leo J. J. Backx, Joseph A. Mostmans
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Patent number: 4582948Abstract: Chloro-aromatic compounds of the formula ##STR1## wherein R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0, 1 or 2; n is 0, 1 or 2; q is 1 or 2; q+m+n is less than 6; and when q is 1, m is 2; are prepared by the vapor phase chloro-denitration reaction of a chlorinating agent with a nitro-aromatic compound of the formula ##STR2## where R, m, n and q are as defined above.Type: GrantFiled: April 27, 1984Date of Patent: April 15, 1986Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Fredrick J. Goetz
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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: 4567280Abstract: In a process for producing an iodo-aromatic compound which comprises iodinating an aromatic compound having an electron-donating substituent bonded to the benzene ring with iodine in the presence of a solvent, the improvement wherein about 1/2 to about 10 moles, per mole of iodine added to the reaction system, of nitrogen dioxide (NO.sub.2) is added in the form of NO.sub.2 to the reaction system, and the reaction is carried out in the presence of nitrogen dioxide.Type: GrantFiled: September 4, 1984Date of Patent: January 28, 1986Assignee: UBE Industries, Ltd.Inventors: Hiroshi Itatani, Mikito Kashima, Yasutaka Tasaki
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Patent number: 4558166Abstract: 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: GrantFiled: March 21, 1984Date of Patent: December 10, 1985Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Erich Klauke
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Patent number: 4542243Abstract: 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: GrantFiled: October 7, 1983Date of Patent: September 17, 1985Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Mitsumasa Umemoto, Tamotsu Asano, Teruyuki Nagata, Satoshi Numata
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Patent number: 4538003Abstract: Process for the monoalkylation/monoarylation of dihaloaromatic compounds by treating the latter with selected magnesium or zinc organometallic reagents in the presence of a nickel/bidentate or tridentate phosphorus ligand. The products are intermediates to agricultural and pharmaceutical compounds.Type: GrantFiled: February 24, 1984Date of Patent: August 27, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Wilson Tam
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Patent number: 4524032Abstract: A process for direct fluorination of etherified or unetherified hydroxy group-bearing aromatic compounds, which comprises reacting an etherified or unetherified hydroxy group-bearing aromatic compound with fluorine gas to give the corresponding etherified or unetherified hydroxy group and at least one fluorine atom-bearing aromatic compound.Type: GrantFiled: January 14, 1983Date of Patent: June 18, 1985Assignee: Daikin Kogyo Co., Ltd.Inventors: Susumu Misaki, Sadamu Ishii, Masahiro Suefuji
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Patent number: 4518808Abstract: Disclosed is a process for the preparation of certain dichloro-hydroxy and alkoxy aromatic compounds by reacting the corresponding unchlorinated compound with sulfuryl chloride in the presence of acetic acid, propionic acid or lower alkyl esters thereof.Type: GrantFiled: September 29, 1983Date of Patent: May 21, 1985Assignee: Eastman Kodak CompanyInventors: Richard H. S. Wang, Garry L. Myers
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Patent number: 4507492Abstract: Allyl derivatives of phenols, thiophenols and arylamines are prepared by contacting such aromatic reactant with an allyl lower alkyl carbonate in the presence of a molybdenum, tungsten or Group VIII metal.Type: GrantFiled: May 6, 1983Date of Patent: March 26, 1985Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4495353Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.Type: GrantFiled: June 13, 1983Date of Patent: January 22, 1985Assignee: Sterling Drug Inc.Inventor: Robert J. Bryant
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Patent number: 4470930Abstract: Chloro-aromatic compounds of the formula ##STR1## wherein R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0 or 1, and n is 0 or 1 are prepared by the vapor phase chloro-denitration reaction of a chlorinating agent with a nitro-aromatic compound of the formula ##STR2## where R, m, and n are as defined above.Type: GrantFiled: February 9, 1982Date of Patent: September 11, 1984Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
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Patent number: 4447660Abstract: Process for the isomerization of ortho- and para-bromophenols or the ethers thereof into corresponding meta-brominated derivatives by isomerizing ortho- and para-bromophenols in the corresponding ethers in the presence of a liquid superacid at a temperature in the region of ambient temperature.Type: GrantFiled: September 30, 1982Date of Patent: May 8, 1984Assignee: PCUK Produits Chimiques Ugine KuhlmannInventors: Marie-Paule Jouannetaud, Jean-Pierre Gesson, Jean-Claude Jacquessy
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Patent number: 4429153Abstract: This invention relates to novel cyclopropane derivatives useful as insecticides, to processes for their preparation, to compositions comprising them and to methods of combatting insect and similar invertebrate pests using them.Type: GrantFiled: January 15, 1982Date of Patent: January 31, 1984Assignee: Imperial Chemical Industries PLCInventor: Nazim Punja
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Patent number: 4424393Abstract: This invention relates to a process for preparing herbicidally active substituted diphenylethers. Also, this invention provides novel intermediates useful in the production of said diphenylethers.Type: GrantFiled: August 24, 1981Date of Patent: January 3, 1984Assignee: PPG Industries, Inc.Inventors: Frederick F. Guzik, Steven E. Pamer, Sidney B. Richter
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9-Deoxy-9-methylene derivatives of (dl)-16-phenoxy and 16-phenoxy substituted prostatriene compounds
Patent number: 4418206Abstract: Novel compounds of the formula: ##STR1## wherein A is CHOH, CHO or COOR; R is hydrogen or a lower alkyl group of 1 to 4 carbon atoms; and the pharmaceutically acceptable, non-toxic salts of compounds in which R is hydrogen; and X is hydrogen, o-, m- or p-halo(fluoro, chloro or bromo), o-, m- or p-methyl or o-, m- or p-methoxy. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretions and as agents for the control of asthmatic attack, because of their bronchodilating activity.Type: GrantFiled: March 22, 1982Date of Patent: November 29, 1983Assignee: Syntex (U.S.A.) Inc.Inventor: Douglas L. Wren -
Patent number: 4407760Abstract: A method for the preparation of difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent mixture.Type: GrantFiled: September 20, 1982Date of Patent: October 4, 1983Assignee: American Cyanamid CompanyInventor: Jack K. Siddens
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Patent number: 4405529Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.Type: GrantFiled: September 20, 1982Date of Patent: September 20, 1983Assignee: American Cyanamid CompanyInventors: Jack K. Siddens, Sivaraman Raghu
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Patent number: 4404148Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.Type: GrantFiled: September 20, 1982Date of Patent: September 13, 1983Assignee: American Cyanamid CompanyInventor: Jack K. Siddens
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Patent number: 4380546Abstract: Azole compounds of the formula ##STR1## where X is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl or phenyl and m is an integer from 1 to 5, and, if m is greater than 1, the X's can be identical or different, n is an integer from 2 to 5, Z is N or CH and Y is CO or CR.sup.1 OR.sup.2, where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or C.sub.1 -C.sub.4 -alkanoyl, and their crop-tolerated addition salts with acids, and metal complexes.The compounds act as fungicides and growth regulators.Type: GrantFiled: April 29, 1981Date of Patent: April 19, 1983Assignee: BASF AktiengesellschaftInventors: Hubert Sauter, Eberhard Ammermann, Costin Rentzea, Bernd Zeeh, Johann Jung, Ernst-Heinrich Pommer
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Patent number: 4377711Abstract: Disclosed are aromatic bromopolyfluoroalkyl ethers of the formula: ##STR1## where n is equal to 1 or 2 and R represents at least one moiety selected from the group consisting of hydrogen, the alkyl radicals having from 1 to 12 carbon atoms, the phenyl radical, the alkoxy radicals having from 1 to 12 carbon atoms, the phenyloxy radical, and the radicals NO.sub.2, CN, Cl, F, Br, I, CF.sub.3, and CONR.sub.1 R.sub.2 and NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are identical or different and represent each a hydrogen or an alkyl radical having from 1 to 6 carbon atoms. Also disclosed is a method for preparation of these ethers. These compounds are useful as intermediates in producing products exhibiting phytosanitary or pharmaceutical activity.Type: GrantFiled: November 4, 1981Date of Patent: March 22, 1983Assignee: Rhone-Poulenc IndustriesInventors: Isabelle Rico, Claude Wakselman
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Patent number: 4368135Abstract: Anisotropic compounds with negative or positive DCA and .DELTA.n.ltoreq.0.2 have the formula (1) ##STR1## in which R.sup.1 and R.sup.2 l are independently hydrogen, alkyl, alkoxy having 1 to 12 carbon atoms respectively, or one of R.sup.1 and R.sup.2 can represent cyclical fragment of formulae (1a) or (1b); ##STR2## the bridges Z.sup.1, Z.sup.2 and Z.sup.3 are identical or different and means covalent bonds or carboxyl or oxycarbonyl groups; R.sup.3 is hydrogen, alkyl or alkoxy group having 1 to 12 carbon atoms, respectively; X.sup.1 and X.sup.4 are independently hydrogen, halogen, nitrile or nitro, wherein at least one of X.sup.1 and X.sup.4 is not hydrogen when R.sup.2 represents a cyclical fragment of formula (1a) or (1b) and Z.sup.2 is a carboxyl group or Z.sup.3 is an oxycarbonyl group, respectively. Liquid crystal compositions are also disclosed.Type: GrantFiled: June 30, 1980Date of Patent: January 11, 1983Assignee: BBC, Brown, Boveri & Company, Ltd.Inventor: Maged A. Osman
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Patent number: 4346244Abstract: Chloroalkoxybenzenes are prepared by reacting a polychlorobenzene with at least one alkali metal hydroxide and an alcohol, ROH, in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O).sub.n R.sub.5 ].sub.3.Type: GrantFiled: March 11, 1981Date of Patent: August 24, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Louis Linguenheld
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Patent number: 4341905Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of an alkali metal halide catalyst.Type: GrantFiled: August 18, 1980Date of Patent: July 27, 1982Assignee: The Dow Chemical CompanyInventor: Paul E. Strege
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Patent number: 4338316Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.Type: GrantFiled: September 26, 1979Date of Patent: July 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Peter R. Marsham
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Patent number: 4336270Abstract: Novel o-benzylphenols as well as a process for their production, a method for combating harmful microorganisms and compositions comprising said o-benzylphenols are provided.Type: GrantFiled: October 5, 1979Date of Patent: June 22, 1982Assignee: Ciba-Geigy CorporationInventor: Rene Muntwyler
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Patent number: 4327036Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.Type: GrantFiled: May 8, 1980Date of Patent: April 27, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank D. Marsh