Polynitro Patents (Class 568/944)
  • Patent number: 11926911
    Abstract: A process for the microfluidic electrochemical synthesis of geminal dipseudohalide or halide-pseudohalide compounds comprising the steps of pumping a solution comprising a compound of Formula I into a microfluidic electrochemical reactor in the presence of a base, one of a halide or pseudohalide salt (MY), and a mediator; applying an electrical current through the microfluidic electrochemical reactor; and performing oxidative addition to create a geminal dipseudohalide or halide-pseudohalide compound of the general Formula II
    Type: Grant
    Filed: January 12, 2023
    Date of Patent: March 12, 2024
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Thorsten G. Schroer, Gregory E. LeCroy, Miguel Aguila, Mayra R. Rodriguez, Tyler J. Downard, Brianna L. MacLeod
  • Publication number: 20140179936
    Abstract: A method producing a surfactant from glycerol by converting glycerol, in a first step, to glycidol, polymerizing glycidol to an aliphatic alcohol and finally substituting a hydroxyl group with a substitute anion.
    Type: Application
    Filed: October 15, 2013
    Publication date: June 26, 2014
    Inventors: Andre Pienaar, Laurence Justin Pienaar Wilson, Michael Stockenhuber
  • Patent number: 8704004
    Abstract: Disclosed is an energetic reactive plasticizer for a plastic bonded explosive (PBX), and specifically an energetic reactive plasticizer for PBX which has high performance and insensitiveness without a plasticizer leak by being bonded with a polymer binder for a plastic bonded explosive.
    Type: Grant
    Filed: February 7, 2013
    Date of Patent: April 22, 2014
    Assignee: Agency for Defense Development
    Inventors: Young Hwan Kwon, Jin Seuk Kim, Bum Jae Lee, In Joo Bae
  • Patent number: 8692036
    Abstract: The present invention relates to a method for preparing 2,3-dimethyl-2,3-dinitrobutane (DMNB), which includes the following steps: (1) making titanium-silicate molecular sieve catalyst, acetone, hydrogen peroxide and ammonia contact and react at 65-80° C. to obtain a modified titanium-silicate molecular sieve catalyst; and (2-1) making acetone oxime and hydrogen peroxide contact and react in the presence of the modified titanium-silicate molecular sieve catalyst and water under the conditions of temperature of 60-90° C. and pH of 8-10, and separating DMNB from the reaction products thereof; or (2-2) making acetone, ammonia and hydrogen peroxide contact and react in the presence of the modified titanium-silicate molecular sieve catalyst and water under the conditions of temperature of 60-90° C. and pH of 8-10, and separating DMNB from the reaction products thereof.
    Type: Grant
    Filed: September 5, 2011
    Date of Patent: April 8, 2014
    Assignee: Ningbo Institute of Technology, Zhejiang University, Zhejiang
    Inventors: Shengjian Zhang, Yingxian Zhao, Hong Zhang
  • Patent number: 8692031
    Abstract: A method for preparing a compound having formula (II) wherein R1 and R2 independently are methyl or ethyl, or R1 and R2 combine to form a C5 or C6 cycloalkyl or cycloalkenyl group. The method includes a step of combining R1R2CHNO2, glutaraldehyde and an amine. The compound is useful in coating compositions and other applications for pH adjustment.
    Type: Grant
    Filed: October 8, 2010
    Date of Patent: April 8, 2014
    Assignees: Dow Global Technologies LLC, ANGUS Chemical Company
    Inventors: Ian Anthony Tomlinson, Glenn Nelson Robinson, Asghar Akber Peera
  • Patent number: 8558038
    Abstract: A method producing a surfactant from glycerol by converting glycerol, in a first step, to glycidol, polymerizing glycidol to an aliphatic alcohol and finally substituting a hydroxyl group with a substitute anion.
    Type: Grant
    Filed: June 21, 2011
    Date of Patent: October 15, 2013
    Assignee: AEL Mining Services Limited
    Inventors: Andre Pienaar, Laurence Justin Pienaar Wilson, Michael Stockenhuber
  • Patent number: 8519199
    Abstract: Provided is a process for the formation of 2-nitropropane and/or 2,2-dinitropropane by the nitration of propane with dilute nitric acid.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: August 27, 2013
    Inventors: Daniel M Trauth, Richard L James
  • Publication number: 20130184504
    Abstract: The present invention relates to a method for preparing 2,3-dimethyl-2,3-dinitrobutane (DMNB), which includes the following steps: (1) making titanium-silicate molecular sieve catalyst, acetone, hydrogen peroxide and ammonia contact and react at 65-80° C. to obtain a modified titanium-silicate molecular sieve catalyst; and (2-1) making acetone oxime and hydrogen peroxide contact and react in the presence of the modified titanium-silicate molecular sieve catalyst and water under the conditions of temperature of 60-90° C. and pH of 8-10, and separating DMNB from the reaction products thereof; or (2-2) making acetone, ammonia and hydrogen peroxide contact and react in the presence of the modified titanium-silicate molecular sieve catalyst and water under the conditions of temperature of 60-90° C. and pH of 8-10, and separating DMNB from the reaction products thereof.
    Type: Application
    Filed: September 5, 2011
    Publication date: July 18, 2013
    Applicant: NINGBO INSTITUE OF TECHNOLOGY ZHEJIANG ZHEJIAND
    Inventors: Shengjian Zhang, Yingxian Zhao, Hong Zhang
  • Publication number: 20130090497
    Abstract: A method producing a surfactant from glycerol by converting glycerol, in a first step, to glycidol, polymerizing glycidol to an aliphatic alcohol and finally substituting a hydroxyl group with a substitute anion.
    Type: Application
    Filed: June 21, 2011
    Publication date: April 11, 2013
    Applicant: AEL MINING SERVICES LIMITED
    Inventors: Andre Pienaar, Laurence Justin Pienaar Wilson, Michael Stockenhuber
  • Publication number: 20110092748
    Abstract: Disclosed are a process and an apparatus for synthesizing nitroalkanes by reaction of a hydrocarbon feedstock with aqueous nitric acid. Energy and capital costs may be reduced by recycling a majority of the aqueous phase back to the reactor.
    Type: Application
    Filed: September 10, 2010
    Publication date: April 21, 2011
    Applicants: DOW GLOBAL TECHNOLOGIES INC., ANGUS CHEMICAL COMPANY
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast, JR.
  • Publication number: 20110028731
    Abstract: Provided is a process for the formation of 2-nitropropane and/or 2,2-dinitropropane by the nitration of propane with dilute nitric acid.
    Type: Application
    Filed: April 8, 2009
    Publication date: February 3, 2011
    Inventors: Daniel M. Trauth, Richard L. James
  • Publication number: 20090299106
    Abstract: A highly energy-producing compound which can be used, for example, as an explosive, propellant, oxidant and the like, and which includes an alkyne unit in which at least one hydrogen atom has been replaced by a trinitromethyl —C(NO2)3 group.
    Type: Application
    Filed: September 22, 2006
    Publication date: December 3, 2009
    Applicant: Diehl BGT Defence GmbH & Co., KG
    Inventor: Ernst-Christian Koch
  • Publication number: 20090038953
    Abstract: A method for the electrochemical synthesis of dinitro compounds is disclosed. The method comprises using an anode to oxidize an inactive chemical mediator, such as a ferrocyanide (Fe(CN)6?4) ion, to an active chemical mediator or oxidizing agent, such as a ferricyanide (Fe(CN)6?3) ion, in the presence of a differential voltage. The oxidizing agent reacts with a nitro compound and a nitrite ion to form a geminal dinitro compound. The anode may continuously oxidize ferrocyanide to regenerate active ferricyanide, thus keeping sufficient amounts of ferricyanide available for reaction.
    Type: Application
    Filed: August 8, 2007
    Publication date: February 12, 2009
    Inventors: Tedd Edward Lister, Robert Vincent Fox
  • Patent number: 7208637
    Abstract: Disclosed are novel compounds that can be used as an energetic binder used for improving the performance and the properties of a high explosive, and a preparation method thereof.
    Type: Grant
    Filed: April 22, 2004
    Date of Patent: April 24, 2007
    Assignee: Agency for Defence a Korean Non-Profit Org.
    Inventors: Jin Seuk Kim, Jin Rai Cho, Keun Deuk Lee, Jae Kyoung Kim
  • Patent number: 6911328
    Abstract: The present invention includes a method for producing 2,3-dimethyl-2,3-dinitrobutane, particularly in high yields, using a peroxidase enzyme site and reacting propane-2-nitronate at the enzyme under appropriate conditions. Peroxidases such as chloroperoxidase, soybean peroxidase and horseradish peroxidase are used. High yields include those amounts that increasingly aid in the manufacture of commercial quantities of 2,3-dimethyl-2,3-dinitrobutane.
    Type: Grant
    Filed: September 4, 2002
    Date of Patent: June 28, 2005
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Angel A. Fitzgerald, Alfredo N. Rayms-Keller
  • Patent number: 6888030
    Abstract: Inclusion of a branched alcohol in the catalytic hydrogenation reaction involving an aliphatic nitro compound dramatically increases the efficiency of the conversion of nitro groups into amino groups. This discovery is of particular value in the production of polyalkyleneamines via nitration of a polyalkene, such as a polybutene, and its subsequent reduction. The polyalkyleneamines so produced are useful as dispersant additives for motor oils and fuels.
    Type: Grant
    Filed: October 22, 2002
    Date of Patent: May 3, 2005
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Wei-Yang Su, Wheeler C. Crawford, John M. Larkin
  • Patent number: 6670506
    Abstract: A method of synthesis of dinitro-diaza-alkanes and intermediate products thereto from alkylamines and esters, whereby a dialkyl ester of a dicarboxylic acid is reacted with an alkylamine in an aqueous medium to form the corresponding dialkyldiamide of the dicarboxylic acid; the resulting dialkyldiamide is nitrated by means of conventional nitration agents to form the corresponding dialkyldinitroamide of the dicarboxylic acid and; the resulting dialkyldinitroamide is reacted with methylamine and/or ethylamine in an aquous medium to yield a corresponding alkylnitroamine and the dimethyldiamide and/or diethyldiamide of the dicarboxylic acid, and the alkylnitroamine is isolated from that, and the isolated alkylnitroamine is condensed in a known manner to form the dinitro-diaza-alkanes.
    Type: Grant
    Filed: November 1, 2001
    Date of Patent: December 30, 2003
    Assignee: Nitrochemie Achau GmbH
    Inventor: Thomas Knott
  • Patent number: 6572717
    Abstract: The invention relates to crystalline hydrazinium nitroformate having a length to diameter ratio of at most 2.5 and a sensitivity to friction and shock not below 20 N and 2 J, respectively, as well as to a method for the preparation thereof.
    Type: Grant
    Filed: March 16, 2001
    Date of Patent: June 3, 2003
    Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno
    Inventors: Jeroen Louwers, Antonius Eduard Dominicus Maria Van Der Heijden
  • Patent number: 6340780
    Abstract: A method of preparing dinitromethane salts usable as intermediate products add starting material for production of explosives and propellants. Substituted 1,2-diazoles, 1,2,4 -triazoles or 1,3-diazines, such as barbituric acid, are nitrated to obtain a gem-dinitro group on a carbon atom in the heterocyclic ring. The product is hydrolysed to split off dinitromethane which is neutralised with a neutralising agent to obtain a corresponding salt of dinitromethane.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: January 22, 2002
    Assignee: Totalfürsvarets Forskningsinstitut
    Inventors: Nikolai Latypov, Ulf Wellmar, Abraham Langlet
  • Patent number: 5879420
    Abstract: Reaction products of polyisobutenes having an average degree of polymerization P of from 10 to 100 and a content E of from 60 to 90% of double bonds which can react with maleic anhydride, E=100% corresponding to the theoretical value for the case where each molecule of the polyisobutene has such a reactive double bond, with oxides of nitrogen or mixtures of oxides of nitrogen and oxygen, are suitable as additives for fuels, in particular for gasoline engines, and for lubricants.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: March 9, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kropp, Eckhard Hickmann, Klaus Ebel, Wolfgang Gunther, Hans Peter Rath, Harald Schwahn
  • 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: 5557015
    Abstract: The invention relates to a method of preparing hydrazine nitroform (HNF) by dissolving nitroform of a purity of more than 98.5 wt % in a solvent and reacting it with hydrazine in the presence of a small amount of proton-transferring medium.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: September 17, 1996
    Assignee: Aerospace Propulsion Products B.V.
    Inventors: Fransiscus W. M. Zee, Johannes M. Mul, Arie C. Hordijk
  • Patent number: 5235119
    Abstract: An efficient direct functionalization of nitrocubanes has been achieved by irradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: August 10, 1993
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Abdollah Bashir-Hashemi
  • Patent number: 5214222
    Abstract: An efficient direct functionalization of nitrocubanes has been achieved by rradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: May 25, 1993
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Abdollah Bashir-Hashemi
  • Patent number: 5214221
    Abstract: An efficient direct functionalization of nitrocubanes has been achieved by rradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: May 25, 1993
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Abdollah Bashir-Hashemi
  • Patent number: 4713232
    Abstract: A process for the management of by-product tetranitromethane (TNM) which avoids the hazards of the prior art isolation or extraction procedures. A selected in-plant liquid or vapor stream, or a reactor off-gas stream from nitration or nitric acid oxidation plant, which contains TNM, is heated to effectively pyrolyze the TNM without undue losses of nitric acid values.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: December 15, 1987
    Assignee: C-I-L Inc.
    Inventors: Chang-Hwa Chin, Anthony C. F. Edmonds, Colin M. Evans
  • Patent number: 4594430
    Abstract: Geminal dinitro compounds are prepared by reacting an organic nitro compound having a replaceable hydrogen on the carbon to which the nitro group is attached with a source of nitrite ions in the presence of an oxidizing agent and a catalytic amount of an alkali metal ferricyanide.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: June 10, 1986
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Vytautas Grakauskas, Lee C. Garver, Kurt Baum
  • Patent number: 4567004
    Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.
    Type: Grant
    Filed: July 18, 1984
    Date of Patent: January 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters
  • Patent number: H350
    Abstract: An energetic plasticizer which is a mixture of bis(2,2,2-trinitroethyl)fol, bis(2,2-dinitropropyl)formal, and a new compound 2,2-dinitropropyl 2,2,2-trinitroethyl formal.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: October 6, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst D. Adolph, Kyung E. Kim
  • Patent number: H351
    Abstract: 4,4,10,10-tetranitro-6,8-dioxatridecane-1,13-diol polyformal, HO(CH.sub.2ub.3 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 (CH.sub.2).sub.3 O[CH.sub.2 O(CH.sub.2).sub.3 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 (CH.sub.2).sub.3 O].sub.n H, which has high energy, high thermal stability, and which is useful as a prepolymer for plastic-bonded explosive compositions.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: October 6, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Kyung E. Kim, Horst G. Adolph