Halogen Containing Patents (Class 568/933)
  • Patent number: 8183418
    Abstract: An improved process is provided for the preparation of 2,6-dihalo-3,5-dinitrotoluene by the nitration of 2,6-dihalotoluene. The direct isolation of highly pure 2,6-dihalo-3,5-dinitrotoluene is accomplished without a water or ice quench, by providing at least one equivalent of SO3 during the reaction, slow crystallization, and isolation of product from a cold crystal slurry.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: May 22, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Joachim C. Ritter
  • Patent number: 8003831
    Abstract: A process is provided for the preparation of 1,3-dihalo-4,6-dinitrobenzene by the nitration of 1,3-dihalobenzene. The direct isolation of highly pure 1,3-dihalo-4,6-dinitrobenzene is accomplished without a water or ice quench, and involves the use of at least one equivalent of SO3 during the reaction, slow crystallization, and isolation of product from a cold crystal slurry.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: August 23, 2011
    Assignee: E.I. duPont de Nemours and Company
    Inventor: Joachim C. Ritter
  • Publication number: 20100160695
    Abstract: An improved process is provided for the preparation of 2,6-dihalo-3,5-dinitrotoluene by the nitration of 2,6-dihalotoluene. The direct isolation of highly pure 2,6-dihalo-3,5-dinitrotoluene is accomplished without a water or ice quench, by providing at least one equivalent of SO3 during the reaction, slow crystallization, and isolation of product from a cold crystal slurry.
    Type: Application
    Filed: December 10, 2009
    Publication date: June 24, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventor: JOACHIM C. RITTER
  • Patent number: 7709684
    Abstract: A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of: a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) i
    Type: Grant
    Filed: May 31, 2007
    Date of Patent: May 4, 2010
    Assignee: BASF SE
    Inventors: Sebastian Peer Smidt, Jochen Dietz, Michael Keil, Thomas Grote
  • Patent number: 6943257
    Abstract: The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon or nitrogen; R1, R2, R3, R4 and R5 which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8 alkyl, a C1-C10 alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10 alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from R1, R2, R3, R4 and R5 may combine to form a ring.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: September 13, 2005
    Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
  • Patent number: 6696613
    Abstract: A process for preparing compounds of the formula: wherein R2 is lower alkyl; or phenyl optionally substituted by from one to five groups, the same or different, which are lower alkyl, lower haloalkyl, halogen or —SR4; R3 is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, —S-alkyl, cycloalkyl having from 3 to 7 carbon atoms in the ring, alkenyl or alkynyl having from 3 to 7 carbon atoms, or —(CR5R6)—SR2 wherein q is one or two; R4 is lower alkyl; R5 and R6 independently represent hydrogen, lower alkyl or lower haloalkyl; and n is zero or an integer from one to three; intermediate compounds of the formula: and processes for preparing them.
    Type: Grant
    Filed: December 31, 2002
    Date of Patent: February 24, 2004
    Assignee: Rhone Poulenc Agrochimie
    Inventors: Virginie Pevere, Alain Gadras, Susan Mary Cramp, Charles Walter Ellwood
  • Publication number: 20030072825
    Abstract: Dinitrohalogenated compounds may be utilized by injection in certain clinical situations to provide a possibility of long term control of human malignancy. In some of those settings no other treatment offers such potential. Preparation methods may include acetone, olive oil, microsomes, liposomes, or combinations thereof. Optimum pretreatment management, dosing and injection techniques are described.
    Type: Application
    Filed: October 17, 2001
    Publication date: April 17, 2003
    Inventor: Max Harry Cohen
  • Patent number: 6362380
    Abstract: A process for preparing nitrobiphenyls of the formula I where m is 1 or 2, R is halogen R′ or OR′, where R′ is a C-organic radical which may carry groups inert under the reaction conditions, n is 0, 1, 2 or 3, and, in the case of n being 2 or 3, the radicals R are the same or different, by reacting a chloronitrobenzene of the formula II in the presence of a palladium catalyst and a base in a solvent with a phenylboronic acid (IIIa) or an alkyl ester thereof of the formula IIIb where R1 is C1-C6-alkyl, or an anhydride thereof. The compounds I are useful as precursors for biphenylamines, which in turn are intermediates for fungicidal crop protection agents.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: March 26, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Eicken, Joachim Gebhardt, Harald Rang, Michael Rack, Peter Schäfer
  • Patent number: 6329529
    Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.
    Type: Grant
    Filed: July 31, 1998
    Date of Patent: December 11, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
  • Patent number: 6284894
    Abstract: A process for the preparation of an allylic aromatic compound in which an aromatic amine is reacted first with a nitrite and then with an allylic olefin having an eliminatable terminal substituent. Novel allylic derivatives of disubstituted benzene compounds are also described.
    Type: Grant
    Filed: December 17, 1999
    Date of Patent: September 4, 2001
    Assignee: Nycomed Imaging AS
    Inventors: Fredrik Ek, Lars Goran Wistrand
  • Patent number: 5600035
    Abstract: Photoreactive compounds are synthesized from 2,5- or 2,6-dintrobenzyl groups. Also disclosed are methods of synthesizing reactive monomers containing 2,5- or 2,6-dintrobenzyl groups.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: February 4, 1997
    Assignee: PPG Industries, Inc.
    Inventors: Charles F. Kahle, II, Neil D. McMurdie, Raphael O. Kollah, Daniel E. Rardon, Gregory J. McCollum
  • Patent number: 5576455
    Abstract: A process for the preparation of 2-chloro-4,5-difluorobenzoic acid and 2,4,5-trifluorobenzoic acid as well as synthetic intermediates useful in and prepared according thereto, comprising reacting a nitrobenzene having the formula ##STR1## wherein X is chloro or fluoro, with an appropriate carbanion to form a compound having the formula ##STR2## wherein one of Y and Z is chloro and the other is nitro, and R is a radical selected from the group consisting of --CCl.sub.3, --CH.sub.2 NO.sub.2, --CH(NO.sub.2)R.sup.1, --CH(CO.sub.2 R.sup.1).sub.2, --CH(C(O)R.sup.2).sub.2, --CH(CN)CO.sub.2 R.sup.1, --CH(CO.sub.2 R.sup.1)COR.sup.2 and --COR.sup.2 where R.sup.1 is alkyl or arylalkyl and R.sup.2 is alkyl, aryl or arylalkyl and, where appearing more than once in such a radical, R.sup.1 and R.sup.2 may be the same or different at each occurrence.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: November 19, 1996
    Assignee: Abbott Laboratories
    Inventors: Xiu C. Wang, Panos Kalaritis, Michelle L. Chang
  • Patent number: 5574188
    Abstract: 4,6-diaminoresorcinol can be prepared in a plurality of steps in such a way thata) 1,3-dichlorobenzene is nitrated with a mixed acid of HNO.sub.3, H.sub.2 SO.sub.4 and SO.sub.3 at 0 to 40.degree. C. in anhydrous H.sub.2 SO.sub.4,b) the resulting 1,3-dichloro-4,6/2,4-dinitrobenzene isomeric mixture is first reacted with benzyl alcohol in the presence of a strong base at -15.degree. C. to +15.degree. C. and then at 20.degree. to 40.degree. C. to give the dibenzyloxy compound andc) the 1,3-dibenzyloxy-4,6-dinitrobenzene isomer arising in pure form in b) is converted to the 4,6-diaminoresorcinol by catalytic hydrogenation.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: November 12, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Behre, Helmut Fiege, Heinz-Ulrich Blank, Uwe Heinz, Wolfgang Eymann
  • Patent number: 5451463
    Abstract: A trifunctional reagent possessing a primary hydroxyl, a secondary hydroxyl, and a primary amino group. This reagent is useful in solid phase oligonucleotide synthesis for the convenient labeling of the 3'-terminus. The secondary hydroxyl may be an phosphoramidite derivative permitting the attachment to the solid phase support. The reporter molecule may be attached to the trifunctional molecule prior to the completion of the oligonucleotide synthesis or after the oligonucleotide is cleaved from the support. A preferred species of this trifunctional molecule is shown below.
    Type: Grant
    Filed: June 3, 1993
    Date of Patent: September 19, 1995
    Assignee: Clontech Laboratories, Inc.
    Inventors: Paul S. Nelson, Mark A. Kent
  • Patent number: 5367108
    Abstract: Dinitro-polyalkylbenzenes can be prepared by nitration of polyalkylbenzenes using HNO.sub.3 in the presence of H.sub.2 SO.sub.4 in such a manner that at least 50% of the H.sub.2 SO.sub.4 is present as reaction medium and HNO.sub.3 and the polyalkylbenzene and any remaining H.sub.2 SO.sub.4 are added simultaneously in such a manner that the added substances polyalkylbenzene and HNO.sub.3 are in the molar ratio of 1:2-10. H.sub.2 SO.sub.4 is used at a concentration from 81 to 96% by weight and HNO.sub.3 at a concentration from 95 to 100% by weight. For the work-up, the dinitro-polyalkylbenzenes are first freed from the majority of the acids and then treated with a highly dilute aqueous solution of a dispersant for separating off residual acid.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: November 22, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz-Ulrich Blank, Bernd-Michael Konig
  • Patent number: 5237077
    Abstract: The present invention relates to a process for producing an aromatic nitro compound by introducing a nitrogen oxide gas and ozone-containing oxygen or air into a halogenated organic solvent dissolving or suspending therein an aromatic compound, thereby subjecting the aromatic compound to nitration. By the use of a system comprising the nitrogen oxide and ozone-containing oxygen or air as the nitrating agent, the aromatic nitro compound can be produced under mild conditions without using any mineral acid. In addition, the various disadvantages due to the use of mineral acid in the conventional process can be avoided by the process of the present invention.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: August 17, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hitomi Suzuki, Takashi Murashima, Kenkichi Tsukamoto
  • Patent number: 5113013
    Abstract: A method for the preparation of a fluorine-containing organic compound which comprises reacting a sulphonyl halide of the formula:RfSO.sub.2 Xwhere Rf represents a fluorinated organic radical and X represents a halogen atom, with a reactive organic halide in the presence of a metal known to complex with fluorinated organic radicals.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: May 12, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Richard L. Powell, Charles A. Heaton
  • Patent number: 4990699
    Abstract: Despite the instabity of perfluoralkyl anions, it is possible to perfluoroalkylate aromatic compounds if appropriately substituted by suitable electronegative substituents (e.g., nitro, trifluoromethylsulfonyl, etc.). Thus a novel Meisenheimer complex is formed by thermally decomposing a salt of a perfluoroalkanoic acid in the presence of an aromatic compound such as 1,3,5-trinitrobenzene. Oxidation with organic hypochlorite yields the corresponding perfluoroalkylated aromatic compound.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: February 5, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4978790
    Abstract: Compounds of the formula ##STR1## in which A represents the radicals ##STR2## in which R.sup.1 and R.sup.2 are different from one another and denote hydrogen, --NO.sub.2 or --NH.sub.2, R.sup.3 is hydrogen or halogen, X represents --NO.sub.2 or --NH.sub.2, with the proviso that R.sup.1 is hydrogen, if R.sup.2 is --NO.sub.2 or --NH.sub.2 and R.sup.2 is hydrogen, if R.sup.1 is --NO.sub.2 or --NH.sub.2.The compounds are prepared from 4,4'-bis[2-(4-hydroxyphenyl)hexafluoroisopropyl]diphenyl ether by nitration or reaction with nitrobenzenes followed by reduction of the nitro groups. They are used for the preparation of high-temperature-resistant polycondensates.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: December 18, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Lau, Gunter Siegemund
  • Patent number: 4956123
    Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: September 11, 1990
    Assignee: Nippon Oils & Fats Company, Ltd.
    Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
  • Patent number: 4952733
    Abstract: Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole. Nitration of 3,5-dichloroanisole under relatively mild conditions gave 3,5-dichloro-2,4,6-trinitroanisole in high yield and purity. Ammonolysis of this latter compound gave the desired TATB. Another route to TATB was through the treatment of the 3,5-dichloro-2,4,6-trinitroanisole with thionyl chloride and dimethylformamide to yield 1,3,5-trichloro-2,4,6-trinitrobenzene. Ammonolysis of this product produced TATB.
    Type: Grant
    Filed: December 21, 1988
    Date of Patent: August 28, 1990
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Donald G. Ott, Theodore M. Benziger
  • Patent number: 4876376
    Abstract: A process for the halogenation (bromination or chlorination)/nitration/fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with a halogen and a nitrating agent 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: December 15, 1987
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Specialistes Chimiques
    Inventors: Michael Desbois, Camille Disdier
  • Patent number: 4780559
    Abstract: A method for the preparation of organic fluorides which comprises reacting a quaternary phosphonium fluoride or bifluoride with an organic substrate having at least one atom or group capable of being replaced by a fluorine atom.
    Type: Grant
    Filed: January 1, 1986
    Date of Patent: October 25, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Stephen J. Brown, James H. Clark
  • Patent number: 4684734
    Abstract: Organic fluorine compounds such as pentafluorobenzonitrile, tetrafluorophthalonitriles, and pentafluoropyridine are produced by a method which comprises causing a chloro- or bromo-organic compound to react with a fluorinating agent such as an alkali metal fluoride in benzonitrile as a solvent at temperatures in the range of 190.degree. to 400.degree. C. under at least spontaneously generated pressure.
    Type: Grant
    Filed: September 13, 1985
    Date of Patent: August 4, 1987
    Assignee: Nippon Shokubai KK Co., Ltd.
    Inventors: Osamu Kaieda, Masaru Awashima, Isao Okitaka, Toshiaki Nakamura
  • Patent number: 4621157
    Abstract: The present invention relates to improvements in processes of preparing dinitrated aromatic compounds, particularly dinitrated aniline and dinitrated substituted aniline compounds, employing relatively dilute and then more concentrated nitric acid as the nitrating agent.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: November 4, 1986
    Assignee: Jerome A. Gross
    Inventor: Larry A. McDaniel
  • Patent number: 4600702
    Abstract: Catalysts compositions useful to catalyze the nitration of aromatic compounds in the vapor phase to produce nitroaromatic compounds are represented by the empirical formula:(M.sup.1.sub.a M.sup.2.sub.b O.sub.c).sub.x (NO.sub.2).sub.ywherein M.sup.1 is at least one element selected from Group 4b of the Periodic Table of the Elements, M.sup.2 is at least one element selected from Group 3b of the Periodic Table of the Elements, a is 1, b is 0.050 to 20, c is a number taken to satisfy the average valences of M.sup.1 and M.sup.2 in the oxidation states in which they exist in the composition, x is 1, and y is 0 to c. The compositions are particularly effective to catalyze the vapor phase nitration of chlorobenzene and are characterized in such reaction by providing a para/ortho isomer distribution ratio of at least about 1.9/l.
    Type: Grant
    Filed: November 14, 1984
    Date of Patent: July 15, 1986
    Assignee: Monsanto Company
    Inventor: Ignatius Schumacher
  • Patent number: 4568781
    Abstract: Fluorine-substituted aromatic compounds are obtained by reacting the corresponding nitro compound with a salt of hydrofluoric acid in the presence of an acid halide.
    Type: Grant
    Filed: January 7, 1985
    Date of Patent: February 4, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Effenberger, Willi Streicher
  • Patent number: 4558166
    Abstract: Process for the preparation of benzal chlorides from benzotrichlorides, according to which benzotrichlorides are reacted with thiols in the presence of metal salts at elevated temperatures.
    Type: Grant
    Filed: March 21, 1984
    Date of Patent: December 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Erich Klauke
  • Patent number: 4440962
    Abstract: To obtain technical TRIFLURALIN with a nitrosoamine content not exceeding 1 ppm, for use as a herbicide, 1-chloro-2,6-dinitro-4-(trifluoromethyl) benzene (DINITRO-PCBT) is freed from nitrosating agents by a process in which DINITRO-PCBT is treated with an aqueous bisulphite solution having an SO.sub.2 concentration of between 1% and 5% at a pH of between 1 and 3, at a temperature of between 50.degree. and 100.degree. C. for a time of between 1 and 3 hours. The organic layer is then separated from the aqueous layer, and the acidity and last traces of the bisulphite solution are eliminated from the organic layer by means of an aqueous alkaline solution.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: April 3, 1984
    Assignee: Oxon Italia S.P.A.
    Inventor: Edoardo Pallucca
  • Patent number: 4391992
    Abstract: A method for the N-denitration of secondary N,2,6-trinitroanilines with phase transfer catalysts.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: July 5, 1983
    Assignee: American Cyanamid Company
    Inventors: William A. Daniels, Rainer K. Zawadzki
  • Patent number: 4350824
    Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or the two radicals R.sup.3 together are alkanediyl,in the presence of at least an equimolar amount of a phosphorous acid triamide of the formulaP(NR.sup.4.sub.2).sub.3in whichR.sup.4 each independently is an alkyl radical, or the two radicals R.sup.4 together are alkanediyl.Advantageously,R.sup.1 is hydrogen,R.sup.2 a C.sub.2 to C.sub.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: September 21, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz
  • Patent number: 4338473
    Abstract: Nitrosation agent(s), contained as by-products in nitrated aromatic compounds after nitration with nitric acid or nitration acid, are removed by a water treatment, wherein the water is distilled off at least partially in vapor form, advantageously under reduced pressure. In the further reaction of the nitrocompounds treated in this manner undesired nitrosamines are practically not formed. The process is especially suitable for the manufacture of 4-di-n-propylamino-3,5-dinitrobenzotrifluoride (Trifluralin), a valuable herbicide, substantially free from nitrosamine(s).
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: July 6, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Kurt Habig, Konrad Baessler, Lothar Schulz, Heinz Schutte
  • Patent number: 4334111
    Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.
    Type: Grant
    Filed: February 17, 1978
    Date of Patent: June 8, 1982
    Assignee: The Dow Chemical Company
    Inventors: Ralph A. Davis, R. Garth Pews
  • Patent number: 4287374
    Abstract: A fluoronitrobenzene is prepared by heating a mono chloronitrobenzene with an alkali metal fluoride and a phase transfer catalyst at a temperature of no more than 200.degree. C.
    Type: Grant
    Filed: October 1, 1979
    Date of Patent: September 1, 1981
    Assignee: The Boots Company
    Inventor: Robert A. North
  • Patent number: 4261908
    Abstract: A process has been developed for isolating aromatic dinitro compounds by using nitric acid in specified concentrations in different portions of a rectifying column and separating off the mixture of aromatic dinitro compounds from the sump of the rectifying column.
    Type: Grant
    Filed: June 21, 1979
    Date of Patent: April 14, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Schroeder, Bernd Thelen, Wolfgang Auge, Karl-Werner Thiem
  • Patent number: RE33168
    Abstract: The present invention relates to improvements in processes of preparing dinitrated .[.aromatic compounds, particularly dinitrated aniline and dinitrated substituted aniline compounds, employing relatively dilute and then more concentrated nitric acid as the nitrating agent.]. .Iadd.aniline and substituted phenol compounds in a two-step process, employing, in the first or mononitration step the spent nitric acid from the second of dinitration step. .Iaddend.
    Type: Grant
    Filed: July 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Jerome A. Gross
    Inventor: Larry A. McDaniel
  • Patent number: H973
    Abstract: 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (DATBA), ##STR1## which is prepared by reacting 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene with cyanotrimethylsilane to form 5-cyano-1,3-diamino-2,4,6-trinitrobenzene which is then hydrolyzed with a strong acid to form the DATBA.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: October 1, 1991
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael Chaykovsky, Horst G. Adolph
  • Patent number: RE34745
    Abstract: High purity 4,6-dinitro-1,3-benzenediol is prepared by (a) contacting a 1,2,3-trihalobenzene with a nitrating agent and an acid under reaction conditions such that a 1,2,3-trihalo-4,6-dinitrobenzene is produced, (b) contacting the 1,2,3-trihalo-4,6-dinitrobenzene prepared in (a) with an alkanol and a base under reaction conditions such that as 4,6-dinitro-2-halo-1,3-benzendiol is produced, and (c) contacting the 4,6-dinitro-2-halo-1,3-benzenediol prepared in (b) with a hydrogenating agent in the presence of a solvent and a catalyst under reaction conditions such that a 4,6-diamino-1,3-benzendiol is produced. This 4,6-diamino-1,3-benzene diol is useful in the preparation of high molecular weight polybenzoxazoles.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: September 27, 1994
    Assignee: The Dow Chemical Company
    Inventor: Zenon Lysenko