Halogen Containing Patents (Class 568/946)
  • Patent number: 8729314
    Abstract: The invention provides a process for preparing bronopol, which process comprises charging a reaction vessel with water, bromopicrin, nitromethane and paraformaldehyde, gradually feeding a base into said reaction vessel under stirring, bringing the reaction to completion and separating bronopol from the aqueous reaction mixture.
    Type: Grant
    Filed: August 28, 2013
    Date of Patent: May 20, 2014
    Assignee: Bromine Compounds Ltd.
    Inventor: Jacob Oren
  • Patent number: 8546619
    Abstract: The invention provides a process for preparing bronopol, which process comprises charging a reaction vessel with water, bromopicrin, nitromethane and paraformaldehyde, gradually feeding a base into said reaction vessel under stirring, bringing the reaction to completion and separating bronopol from the aqueous reaction mixture.
    Type: Grant
    Filed: February 26, 2009
    Date of Patent: October 1, 2013
    Assignee: Bromine Compounds Ltd.
    Inventor: Jacob Oren
  • Patent number: 8415513
    Abstract: A continuous process of preparing bromopicrin is disclosed. The process is effected by transferring a continuous flow of a first mixture and a continuous flow of a second mixture into a first reactor, the first mixture containing nitromethane and bromine and the second mixture containing an aqueous solution of an alkaline substance, to thereby obtain a reaction mixture which comprises bromopicrin in said first reactor; and collecting the bromopicrin from the reaction mixture. Highly pure bromopicrin obtained by this process is also disclosed.
    Type: Grant
    Filed: May 26, 2008
    Date of Patent: April 9, 2013
    Assignee: Bromine Compounds Ltd.
    Inventors: Jakob Oren, Nasif Yassin, Ron Frim
  • Publication number: 20120168663
    Abstract: Disclosed are heat transfer fluids which possess a highly desirable and unexpectedly superior combination of properties, and heat transfer systems and methods based on these fluids. The heat transfer fluid comprise from about 30 to about 70 percent, on a molar basis, of carbon dioxide (CO2) and from about 30 to about 70 percent, on a molar basis, of hydrofluorocarbon (HFC), preferably HFC having one to two carbon atoms, and even more preferably trans-1,1,1,3-tetrafluoropropene (HFC-32). The preferred fluids of the present invention have a vapor pressure of at least about 100 psia at 40?F and are also preferably not azeotropic.
    Type: Application
    Filed: June 15, 2010
    Publication date: July 5, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Rajiv R. Singh, Michael Van Der Puy, Andrew J. Poss, Ian R. Shankland
  • Patent number: 7943806
    Abstract: Process of preparing high purity bromopicrin, and high purity bromopicrin produced therefrom. Providing a mixture of nitromethane and bromine, and preferably water, and absent of organic solvent. Adding an aqueous solution of an alkaline substance to the mixture, thereby providing a reaction mixture containing bromopicrin, the adding performed such that no excess of the alkaline substance occurs in the reaction mixture during the adding. Collecting the organic phase (containing the bromopicrin) from the reaction mixture. No need for subjecting the organic phase of the reaction mixture to distillation or extraction, for obtaining near quantitative yield of bromopicrin having purity of at least equal to or greater than 96 weight percent. Process parameters controlling selectivity of reaction forming bromopicrin are molar ratio of bromine and nitromethane in the mixture; reaction temperature while bromopicrin is formed; concentration of the alkaline substance in the aqueous solution; and reaction time.
    Type: Grant
    Filed: August 22, 2006
    Date of Patent: May 17, 2011
    Assignee: Bromine Compounds Ltd.
    Inventors: Jakob Oren, Leah Golan, Ron Frim
  • Publication number: 20100204528
    Abstract: A continuous process of preparing bromopicrin is disclosed. The process is effected by transferring a continuous flow of a first mixture and a continuous flow of a second mixture into a first reactor, the first mixture containing nitromethane and bromine and the second mixture containing an aqueous solution of an alkaline substance, to thereby obtain a reaction mixture which comprises bromopicrin in said first reactor; and collecting the bromopicrin from the reaction mixture. Highly pure bromopicrin obtained by this process is also disclosed.
    Type: Application
    Filed: May 26, 2008
    Publication date: August 12, 2010
    Applicant: Bromine Compounds Ltd.
    Inventors: Jakob Oren, Nasif Yassin, Ron Frim
  • Publication number: 20100152501
    Abstract: Process of preparing high purity bromopicrin, and high purity bromopicrin produced therefrom. Providing a mixture of nitromethane and bromine, and preferably water, and absent of organic solvent. Adding an aqueous solution of an alkaline substance to the mixture, thereby providing a reaction mixture containing bromopicrin, the adding performed such that no excess of the alkaline substance occurs in the reaction mixture during the adding. Collecting the organic phase (containing the bromopicrin) from the reaction mixture. No need for subjecting the organic phase of the reaction mixture to distillation or extraction, for obtaining near quantitative yield of bromopicrin having purity of at least equal to or greater than 96 weight percent. Process parameters controlling selectivity of reaction forming bromopicrin are molar ratio of bromine and nitromethane in the mixture; reaction temperature while bromopicrin is formed; concentration of the alkaline substance in the aqueous solution; and reaction time.
    Type: Application
    Filed: August 22, 2006
    Publication date: June 17, 2010
    Applicant: Bromine Compounds Ltd.
    Inventors: Jakob Oren, Leah Golan, Ron Frim
  • Patent number: 5631406
    Abstract: Dichloroformals of the formula(RCH.sub.2 O).sub.2 CCl.sub.2wherein R is --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.su), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, or --CF.sub.2 CF.sub.3. These dichloroformals are prepared by reacting the corresponding thionocarbonate of the formula(RCH.sub.2 O).sub.2 C.dbd.S,wherein R is as defined above, with sulfuryl chloride in the presence of a Friedel-Craft catalyst (e.g., AlCl.sub.3 or TiCl.sub.4). Another method is to react the thionocarbonate with chlorine gas in the presence of a polar additive such as 2,2,2-trifluoroethanol or acetonitrile. These energetic dichloroformals are useful as explosive and propellant ingredients and as intermediates in the synthesis of other energetic explosive and propellant ingredients.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: May 20, 1997
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: William H. Gilligan
  • Patent number: 5364989
    Abstract: Methods for the production of 1,1,1-trihalogeno-2-nitroethanes from 1,1-dihalogenoethylene by using nitric acid or its salt and hydrogen chloride or hydrogen bromide or its salt, and for the production of .alpha.-unsaturated amines from the 1,1,1-trihalogeno-2-nitroethanes which are useful as insecticides.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: November 15, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Isao Aoki, Takanori Tabuchi, Isao Minamida
  • Patent number: 5180859
    Abstract: A process for the preparation of halonitroalkanes, e.g. bromonitromethane, is disclosed in which a nitroalkane is reacted with an alkali metal base or an alkaline earth metal base, and the resulting nitroalkane salt is halogenated to form the halonitroalkane in a reaction mixture. The process is improved by acidifying the reaction mixture, preferably to pH=0-4, and thereafter recovering the halonitroalkane by azeotropic distillation of the reaction mixture. The acidification step increases the amount of halonitroalkane recovered, as compared to prior art processes in which the reaction mixture is distilled without prior acidification.
    Type: Grant
    Filed: July 7, 1992
    Date of Patent: January 19, 1993
    Assignee: Great Lakes Chemical Corporation
    Inventors: Larry D. Timberlake, James L. Brennan
  • Patent number: 5124476
    Abstract: .alpha.-Fluoroacryloyl derivatives are prepared by reacting a dihalogenopropene with an anhydrous mixture of nitric acid and hydrofluoric acid to give a 1-nitro-2,2-fluorohalogeno-3-halogenopropane, converting this in the presence of a strong acid and a little water at elevated temperature to a 2,2-fluorohalogeno-3-halogenopropanoic acid, converting this into an ester or an amide and finally treating this with a dehalogenating agent.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: June 23, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Albrecht Marhold
  • Patent number: 5043489
    Abstract: A method of preparing a monohalogenated nitroalkane which comprises reacting equal molar quantities of an alkali metal hydroxide and a nitroalkane in a suitable medium to form a nitronate salt therein, promptly mixing the medium containing the nitronate salt with an equal molar quantity of a halogen to form a monohalogenated nitroalkane in the medium, promptly adding a material to the medium containing the monohalogenated nitroalkane to terminate any further halogenation therein, and recovering the monohalogenated nitroalkane from the medium.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: August 27, 1991
    Assignee: Angus Chemical Company
    Inventors: Vincent Nocito, Louis J. Bedell, Mathew I. Levinson
  • Patent number: 4806280
    Abstract: Compounds of formula ##STR1## in which n denotes an integer from 1 to 10 and X and Y, which are identical or different, each denote an electron-attracting group, are made by reacting a halogenating agent with a compound of formula ##STR2## in which R, X and Y are as hereinbefore defined, anionized by a base.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: February 21, 1989
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4705650
    Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: November 10, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4533776
    Abstract: In the preparation of an .alpha.-fluorinated nitroalkane of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and individually represent hydrogen, fluorine, chlorine, bromine, alkyl, halogenoalkyl or cycloalkyl, orR.sup.1 and R.sup.3 have the meaning indicated andR.sup.2 and R.sup.4 together represent an alkylene group having 3-6 carbon atoms,by conjugated nitrofluorination of the corresponding olefin of the formula ##STR2## the improvement which comprises employing about 1.1 mols of hydrogen fluoride and 1 to 2 mols of nitric acid per mol of olefin and carrying out the reaction in the presence of an agent which binds water, e.g. chlorosulphonic acid, fluorosulphonic acid, sulphur trioxide, sulphur dioxide, thionyl chloride, thionyl fluoride, sulfuryl chloride or sulfuryl fluoride. The end products, some of which are known, are useful as intermediates in synthesizing herbicides.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: August 6, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Hermann Hagemann, Erich Klauke
  • Patent number: 4518812
    Abstract: In the conjugated nitrofluorination of an olefin by reacting an olefin of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently is hydrogen, fluorine, chlorine, bromine, alkyl, halogenoalkyl or cycloalkyl, orR.sup.2 and R.sup.4 together are an alkylene radical of 3 to 6 carbon atoms,with hydrogen fluoride and nitric acid to produce an .alpha.-fluorinated nitroalkane of the formula ##STR2## the improvement which comprises effecting the reaction in a vessel protected against corrosion employing about 1 to 1.1 mols of hydrogen fluoride and about 1 to 2 mols of nitric acid per mol of olefin. The process uses much less HF than heretofore and the products are useful intermediates in making herbicides. Some of the products are new.
    Type: Grant
    Filed: January 31, 1984
    Date of Patent: May 21, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Hermann Hagemann, Erich Klauke
  • Patent number: 4219660
    Abstract: There are disclosed herein derivatives of bisfunctionalized compounds, wherein said compounds have been formed by the introduction of a nitro group and a hydroxyl group in the form of an ester into a conjugated diene molecule by treatment of said conjugated dienes with nitric acid in the presence of a carboxylic acid anhydride. The novel compounds produced by this process are useful as bactericides, fungicides and valuable organic synthesis intermediates.
    Type: Grant
    Filed: June 24, 1977
    Date of Patent: August 26, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Pius A. Wehrli