Nitromethane Patents (Class 568/948)
  • Patent number: 9187436
    Abstract: Provided is a process for the formation of nitrated compounds by the nitration of hydrocarbon compounds with dilute nitric acid. Also provided are processes for preparing industrially useful downstream derivatives of the nitrated compounds, as well as novel nitrated compounds and derivatives, and methods of using the derivatives in various applications.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: November 17, 2015
    Assignee: ANGUS CHEMICAL COMPANY
    Inventors: Daniel M. Trauth, George D Green, Raymond J. Swedo, Richard L. James, Ian A. Tomlinson
  • Patent number: 9133094
    Abstract: Disclosed are processes and apparatuses for concentrating at least one organic acid using an alkyl acetate as an entrainer. The processes and apparatuses may use the same alkyl acetate as an entrainer to concentrate a mixture of organic acids.
    Type: Grant
    Filed: April 5, 2012
    Date of Patent: September 15, 2015
    Assignee: ANGUS CHEMICAL COMPANY
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast, Jr.
  • Patent number: 8558039
    Abstract: Disclosed is an apparatus for synthesizing nitroalkanes by reaction of a hydrocarbon feedstock with aqueous nitric acid. The apparatus may be designed such that it can synthesize more than one nitroalkane using the same equipment.
    Type: Grant
    Filed: November 22, 2010
    Date of Patent: October 15, 2013
    Assignees: Dow Global Technologies LLC, ANGUS Chemical Company
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast, Jr., Ravindra S. Dixit
  • Publication number: 20130245340
    Abstract: Disclosed are a process and an apparatus for concentrating an organic acid by using a nitroalkane as an entrainer for the azeotropic removal of water from an aqueous organic acid solution. The nitroalkane may be the same as a nitroalkane that is the product of a high pressure nitration process that produces nitroalkanes and aqueous organic acid.
    Type: Application
    Filed: December 7, 2011
    Publication date: September 19, 2013
    Applicants: ANGUS CHEMICAL COMPANY, DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Mahesh Ratnakar Sawant, Daniel M. Trauth, John G. Pendergast
  • Patent number: 8431754
    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: Grant
    Filed: September 10, 2010
    Date of Patent: April 30, 2013
    Assignees: Dow Global Technologies LLC, ANGUS Chemical Company
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast, Jr.
  • Patent number: 8410323
    Abstract: Disclosed are a process and apparatus for synthesizing nitroalkanes by reaction of a hydrocarbon feedstock with aqueous nitric acid. Energy and capital costs may be reduced by using a dividing wall column.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: April 2, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast, Jr.
  • Patent number: 8088686
    Abstract: The present invention provides a method of remedying deterioration of an insulating film which, during the remedial treatment of an insulating film deteriorated by plasma treatment, does not leave residual remedial agent on the wiring material such as the copper wiring layer, can be conducted using a dry process, and exhibits excellent applicability to mass production. The insulating film that has been deteriorated by plasma treatment is brought into contact with a remedial agent composed of a compound with a molecular structure having at least one of a nitro group and a carbonyl group, and at least one of a hydrocarbon group and a hydrogen group.
    Type: Grant
    Filed: April 18, 2007
    Date of Patent: January 3, 2012
    Assignee: Taiyo Nippon Sanso Corporation
    Inventors: Shuji Nagano, Satoshi Hasaka, Minoru Inoue, Toshinori Shibata
  • Publication number: 20110105806
    Abstract: A method for stabilizing nitro compounds against discoloration. The method comprises reacting nitro compounds containing color-forming impurities with nitric acid, neutralizing and washing the product, and distilling therefrom purified nitro compounds.
    Type: Application
    Filed: April 8, 2009
    Publication date: May 5, 2011
    Inventors: Daniel M. Trauth, Edward L. Little, Richard L. James, John D. Gummere, Morteza Mokhtarzadeh, Li Wang
  • Publication number: 20110092749
    Abstract: Disclosed are a process and apparatus for synthesizing nitroalkanes by reaction of a hydrocarbon feedstock with aqueous nitric acid. Energy and capital costs may be reduced by using a dividing wall column.
    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: 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: 20110092750
    Abstract: Provided is a process for making nitrated hydrocarbons by reacting aqueous nitric acid with a hydrocarbon feedstock and a carboxylic acid under specific reaction conditions.
    Type: Application
    Filed: October 6, 2010
    Publication date: April 21, 2011
    Inventors: Daniel M. Trauth, George D. Green, Raymond J. Swedo
  • Publication number: 20090099384
    Abstract: The present invention provides a method of remedying deterioration of an insulating film which, during the remedial treatment of an insulating film deteriorated by plasma treatment, does not leave residual remedial agent on the wiring material such as the copper wiring layer, can be conducted using a dry process, and exhibits excellent applicability to mass production. The insulating film that has been deteriorated by plasma treatment is brought into contact with a remedial agent composed of a compound with a molecular structure having at least one of a nitro group and a carbonyl group, and at least one of a hydrocarbon group and a hydrogen group.
    Type: Application
    Filed: April 18, 2007
    Publication date: April 16, 2009
    Inventors: Shuji Nagano, Satoshi Hasaka, Minoru Inoue, Toshinori Shibata
  • Patent number: 6007648
    Abstract: An improved, liquid, explosive composition comprising nitromethane, a nitethane sensitizer and an energetic compound. The energetic compound is selected from the group consisting of 4,5-dihyro-3-nitroisoxazole, 1,3-dinitropropane, trans1,2-dinitrocyclopropane and 1,1-dinitroethane.
    Type: Grant
    Filed: February 23, 1998
    Date of Patent: December 28, 1999
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: John D. Sullivan, Jr., Peter A. Wade, Abraham L. Turetsky
  • 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: 4992603
    Abstract: Nitromethane is preparaed from a nitriding agent comprising an oxygenated nitrogen compound and a carbon compound containing two carbon atoms and at least one atom other than carbon and hydrogen.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: February 12, 1991
    Assignee: S.E.P.P.I.C. Societe d'Exploitation de Produits pour les Industries Chimiques
    Inventors: Roger Mari, Jacques Quibel
  • Patent number: 4820881
    Abstract: A process to decolorize and stabilize nitro compounds by contacting the nitro compound with an alkaline earth metal hypochlorite particulate material.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: April 11, 1989
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Robert J. Kupper
  • Patent number: 4766257
    Abstract: A process for selectively forming nitrohydrocarbon compounds by contacting, at elevated temperature and pressure and in a homogeneous gas phase, an olefinic unsaturated compound having at least three carbon atoms with NO.sub.2 alone or in the presence of oxygen and/or water.
    Type: Grant
    Filed: September 12, 1984
    Date of Patent: August 23, 1988
    Assignee: W. R. Grace & Co.
    Inventor: Shu-Chieh P. Wang
  • 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: 4626607
    Abstract: The invention concerns the manufacture of nitromethane by nitration of mene in a homogeneous gaseous phase, the nitrating agent being nitric acid, nitrogen peroxide or mixtures thereof. According to the disclosed process, the molar ratio methane/nitrating agent is between 0.1 and 5; the reaction contact time between 0.1 and 120 seconds; the reaction pressure between 1 and 35 bars; the temperature between 270.degree. and 600.degree. C. The nitration is carried out in the presence of an active agent of the halogen or derivative type introduced in a molar ratio at the most equal to 3. An installation is disclosed for industrially manufacturing nitromethane.
    Type: Grant
    Filed: January 25, 1985
    Date of Patent: December 2, 1986
    Assignee: Societe Chimique de la Grande Pariosse, Azote et Produits Chimiques
    Inventors: Bernard Jacquinot, Jacques Quibel, Roger Mari
  • Patent number: 4583991
    Abstract: The tendency of nitromethane to detonate when used as a fuel in an internal combustion engine surprisingly has been found to be reduced by adding to the fuel a detonation reducing amount of an additive selected from the group consisting of nitroethane, 2-nitropropane, and mixtures thereof. Nitromethane fuel compositions having a reduced tendency to detonate are also provided.
    Type: Grant
    Filed: July 17, 1985
    Date of Patent: April 22, 1986
    Assignee: Angus Chemical Company
    Inventors: Geoff J. Germane, Gary L. Hess
  • Patent number: 4518811
    Abstract: A reactor for nitration of saturated hydrocarbons having less than five con atoms, alone or in admixture, in the gaseous phase under pressure is made up of a reaction enclosure, in which a tube or pipe bank is in contact with a heated fluid of high heat-exchange capacity. The inside perimeter of the tubes does not exceed 800 mm, and if circular not in excess of 250 mm, and the ratio of the surface of the tube bank, in contact with the reaction medium, to the volume of the reaction enclosure is 1:1 to 3:1.The reactor apparatus further includes a mechanical means to uniformly distribute the delivery of reaction medium gases to the various tubes of the bank so that the load difference between the most loaded tube and that of the least loaded tube is equal to 10% at the most.The reactor also includes a tube bank injector which feeds the tube bank to assure homogeneous mixing of all the reaction fluids in the tube bank.
    Type: Grant
    Filed: September 15, 1983
    Date of Patent: May 21, 1985
    Assignee: Societe Chimique de la Grande Paroisse - Azote et Products Chimiques
    Inventors: Pierre Lhonore, Jacques Quibel, Bernard Jacquinot, Yvon Jestin, Robert Pelletier
  • Patent number: 4517393
    Abstract: A process for selectively forming nitro compounds by contacting, at elevated temperature and pressure and in a homogeneous gas phase, a ketone having from three to ten carbon atoms with nitrogen dioxide alone or in the presence of oxygen and/or water.
    Type: Grant
    Filed: December 19, 1983
    Date of Patent: May 14, 1985
    Assignee: W. R. Grace & Co.
    Inventors: Shu-Shieh P. Wang, Martin B. Sherwin
  • Patent number: 4517394
    Abstract: A process for selectively forming nitroalkanes and nitroaromatics by contacting, at elevated temperature and pressure and in a homogeneous gas phase, an organic carboxylic acid having from two to ten carbon atoms with NO.sub.2 alone or in the presence of oxygen and/or water.
    Type: Grant
    Filed: December 19, 1983
    Date of Patent: May 14, 1985
    Assignee: W. R. Grace & Co.
    Inventors: Shu-Chieh P. Wang, Martin B. Sherwin
  • Patent number: 4517392
    Abstract: A process for selectively forming nitro compounds by contacting, at elevated temperature and pressure and in a homogeneous gas phase, an alcohol having from two to ten carbon atoms with nitrogen dioxide alone or in the presence of oxygen and/or water.
    Type: Grant
    Filed: December 19, 1983
    Date of Patent: May 14, 1985
    Assignee: W. R. Grace & Co.
    Inventors: Shu-Chieh P. Wang, Martin B. Sherwin
  • Patent number: 4469904
    Abstract: A process for selectively forming nitro compounds by contacting, at elevated temperature and pressure and in a homogeneous gas phase, an organic carboxylic acid having from two to ten carbon atoms with NO.sub.2 or HNO.sub.3 alone or in the presence of oxygen and/or water.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: September 4, 1984
    Assignee: W. R. Grace & Co.
    Inventors: Shu-Chieh P. Wang, Martin B. Sherwin
  • Patent number: 4458094
    Abstract: An improved process for forming nitroparaffins by gaseous phase nitration of hydrocarbons higher than methane. The improvement comprises carrying out the nitration in the presence of a small amount of oxygenated hydrocarbons selected from aldehydes, ketones, alcohols, ethers and mixtures thereof.
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: July 3, 1984
    Assignee: W. R. Grace & Co.
    Inventor: Martin B. Sherwin
  • Patent number: 4431842
    Abstract: A process of making nitroalkanes which comprises reacting a lower alkanol, e.g. methanol, and nitric acid (HNO.sub.3) in the vapor phase in the presence of a catalyst which is an oxide or a salt of a metal of Group II of the periodic table, e.g. calcium chloride.
    Type: Grant
    Filed: December 1, 1982
    Date of Patent: February 14, 1984
    Assignee: The Dow Chemical Company
    Inventor: William V. Hayes
  • Patent number: 4424385
    Abstract: An improved process for forming nitromethane by contacting liquid methyl halide with an alkali or alkaline earth metal nitrite in the presence of an excess of the liquid methyl halide.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: January 3, 1984
    Assignee: W. R. Grace & Co.
    Inventor: Sheldon B. Markofsky
  • Patent number: 4421940
    Abstract: An improved process for the vapor phase nitration of alkanes comprising feeding the alkane with an inert diluent gas and vaporizing the nitric acid on the surface of a catalyst bed which is the salt or oxide of a group II metal of the periodic chart.
    Type: Grant
    Filed: February 25, 1982
    Date of Patent: December 20, 1983
    Assignee: The Dow Chemical Company
    Inventor: William V. Hayes
  • Patent number: 4329523
    Abstract: An improved process for the vapor phase nitration of methane comprising delivering preheated (1000.degree.-1250.degree. F.) methane at a flow rate of not less than 20,000 SCFH into a reaction chamber of 3.334 inches in diameter maintained at about 950.degree. F., delivering nitric acid into the reaction chamber through a plurality of orifices perpendicularly mounted with respect to the methane flow, whereat the nitric acid vaporizes, mixes with the methane and reacts therewith, and exiting the reaction mixture after a reaction time of 30 to 250 milliseconds and recovering nitromethane from the reaction mixture.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: May 11, 1982
    Assignee: International Minerals & Chemical Corp.
    Inventors: Richard L. James, Richard S. Egly
  • Patent number: 4319059
    Abstract: A process for making nitroalkanes in which an alpha-bromoalkanoic acid is reacted with an alkali metal nitrite, e.g. NaNO.sub.2, in the presence of the magnesium ion (Mg.sup.++) in an aprotic solvent to form a chelate. Neutralization of the chelate with a mineral acid produces a nitroalkane having one less carbon atom than the reactant bromoalkanoic acid.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: March 9, 1982
    Assignee: The Dow Chemical Company
    Inventor: Nobuyuki Ishibe
  • Patent number: 4313010
    Abstract: Nitroparaffins are made in the homogeneous gaseous phase by nitration of ethane, performed in the presence of an active agent carrying an NO or NO.sub.2 group that is easily transferable. The process is applicable particularly to making nitromethane with high yields.
    Type: Grant
    Filed: November 14, 1979
    Date of Patent: January 26, 1982
    Assignee: Societe Chimique de la Grande Paroisse, Azote et Produits Chimiques
    Inventors: Pierre Lhonore, Bernard Jacquinot, Jacques Quibel, Roger Mari
  • Patent number: 4313009
    Abstract: A process making nitroparaffins comprises a nitration reaction in the gass phase, under pressure, in a closed loop with recycling of the products that have not reacted, with continuous deconcentration purge and continuous input of hydrocarbon and nitrating agent. The process is applicable to nitration of saturated hydrocarbon less than C.sub.5, above or in mixture.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: January 26, 1982
    Assignee: Societe Chimique de la Grande Paroisse, Azote et Produits Chimiques
    Inventors: Pierre Lhonore, Jacques Quibel, Bernard Jacquinot
  • Patent number: H1223
    Abstract: A method of producing FDNE using readily available fluoroolefins as a fluorine source.
    Type: Grant
    Filed: May 17, 1991
    Date of Patent: August 3, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Thomas G. Archibald, Nghi Van Nguyen, Kurt Baum