Nitroalkanes Patents (Class 568/947)
  • Patent number: 9504933
    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: August 22, 2013
    Date of Patent: November 29, 2016
    Assignee: ANGUS CHEMICAL COMPANY
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast, Jr., Ravindra S. Dixit
  • Patent number: 9464029
    Abstract: The invention relates to a process for preparing nitroalkanes by reaction of at least one alkane with at least one nitrating agent in the gas phase, wherein the nitration is carried out in a microstructured reaction zone having parallel channels having hydraulic diameters of less than 2.5 mm and a total specific internal surface area of more than 1600 m2/m3 and the alkane and the nitrating agent are conveyed under a pressure of from 1 bar to 20 bar through the reaction zone and reacted at a temperature of from 150° C. to 650° C. and the reaction products are cooled downstream of the reaction zone and discharged and the at least one nitrating agent is introduced over from two to ten introduction points along the reaction zone.
    Type: Grant
    Filed: April 25, 2014
    Date of Patent: October 11, 2016
    Assignee: BASF SE
    Inventors: Ralf Boehling, Michael Hayer, Alwin Rehfinger, Michael Schelper, Johann-Peter Melder, Martin Ernst, Joaquim Henrique Teles
  • Patent number: 9340486
    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: April 1, 2013
    Date of Patent: May 17, 2016
    Assignee: ANGUS CHEMICAL COMPANY
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast, Jr.
  • Publication number: 20150094501
    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: July 23, 2013
    Publication date: April 2, 2015
    Inventors: Daniel M. Trauth, Richard L. James
  • Publication number: 20140031594
    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: Application
    Filed: April 5, 2012
    Publication date: January 30, 2014
    Applicants: ANGUS CHEMICAL COMPANY, DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Mahesh Sawant, Daniel M. Trauth, John G. Pendergast
  • 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: 8415514
    Abstract: Disclosed are a process and an apparatus for synthesizing nitroalkanes by reaction of a hydrocarbon feedstock with aqueous nitric acid. By using an isothermal reactor with multiple input ports for aqueous nitric acid, a hydrocarbon feedstock may be sequentially exposed to a plurality of flows of aqueous nitric acid as it flows through the reactor.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: April 9, 2013
    Assignee: ANGUS Chemical Company
    Inventor: Daniel M. Trauth
  • Patent number: 8338620
    Abstract: The invention related to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, especially renin inhibitors, such as Aliskiren, the invention relates to a process for the manufacture of a compound of the formula I, or a salt thereof, wherein R1 as well as Act are as defined in the specification, and processes of manufacturing this compound as well as intermediates in this process.
    Type: Grant
    Filed: April 1, 2008
    Date of Patent: December 25, 2012
    Assignee: Novartis AG
    Inventor: Gottfried Sedelmeier
  • Patent number: 8324435
    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: Grant
    Filed: October 6, 2010
    Date of Patent: December 4, 2012
    Inventors: Daniel M. Trauth, George D. Green, Raymond J. Swedo
  • Patent number: 8207382
    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: Grant
    Filed: April 8, 2009
    Date of Patent: June 26, 2012
    Inventors: Daniel M. Trauth, Edward L. Little, Richard L. James, John D. Gummere, Morteza Mokhtarzadeh, Li Wang
  • Publication number: 20110160496
    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: Application
    Filed: November 22, 2010
    Publication date: June 30, 2011
    Applicants: DOW GLOBAL TECHNOLOGIES INC., ANGUS CHEMICAL COMPANY
    Inventors: Mahesh SAWANT, Daniel M. Trauth, John G. Pendergast, JR., Ravindra S. Dixit
  • 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: 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: 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: 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: 20110040092
    Abstract: The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.
    Type: Application
    Filed: September 5, 2008
    Publication date: February 17, 2011
    Applicant: THE SECRETARY OF STATE FOR DEFENSE
    Inventors: Christopher Murray, Graham Sandford
  • Publication number: 20110028732
    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: Application
    Filed: April 8, 2009
    Publication date: February 3, 2011
    Applicants: ANGUS CHEMICAL COMPANY, GLOBAL TECHNOLOGIES INC.
    Inventors: Daniel M. Trauth, George D. Green, Raymond J. Swedo, Richard L. James, Ian A. Tomlinson
  • Patent number: 7678948
    Abstract: This application discloses provides a process for the introduction of nitro-group functionality into a compound which contains also a site of unsaturation and/or oxygen functionality by direct (one step) oxidation of an oxime functional group mediated by a molybdenum VI/VII peroxo complex, the process comprising: (a) providing a substrate of Formula I containing an oxime functional group; wherein R1 and R2 are selected independently from linear, branched or cyclic alkyl and linear, branched or cyclic alkenyl groups, optionally substituted, with the proviso that at least one of R1 or R2 contains a carbon/carbon double bond; and (b) contacting said substrate of Formula I with a molybdenum oxidation complex, thereby oxidizing said oxime functional group to a nitro functional group to yield the structure of Formula III. Where R1 and R2 are as defined above.
    Type: Grant
    Filed: November 19, 2008
    Date of Patent: March 16, 2010
    Assignee: Schering Corporation
    Inventors: Tiruvettipuram K. Thiruvengadam, Tao Wang, John S. Chiu, Jing Liao
  • 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: 5956657
    Abstract: The method provides nitro compounds at a high conversion and selectivity by nitrating substrates under comparatively mild conditions in the absence of catalysts. Organic substrates are nitrated using no catalysts or ozone, but using (1) at least one nitrogen compound selected from N.sub.2 O or NO and oxygen. It is advantageous for the nitration reaction to employ a nitrogen compound obtained by a reaction of the nitrogen compound with oxygen, particularly a nitrogen oxide comprising N.sub.2 O.sub.3 as a main component. Additionally, organic substrates are nitrated using (2) NO.sub.2. The substrates include a compound having a methine-carbon atom, and a compound having a methyl group or methylene group in an adjacent position to an aromatic ring.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: September 21, 1999
    Assignees: Daicel Chemical Industies, Ltd., Yasutaka Ishii
    Inventors: Tatsuya Nakano, Satoshi Sakaguchi, Yasutaka Ishii
  • Patent number: 5442095
    Abstract: Catalysts based on rhodium and water-soluble phosphine obtained by using rhodium perchlorate as the precursor rhodim salt. Also, processes for the preparation of these catalysts and to their use are provided.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: August 15, 1995
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Patrick Auvray
  • 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: 4908110
    Abstract: Infrared laser-induced production of nitrated products is achieved by irradiating compounds selected from propane, n-butane, isobutane, n-pentane, and cyclopropane in the gas phase while in a stainless steel cell 5.times.5.times.10 cm equipped with zinc selenide windows to admit the infrared laser radiation in the range of 10.4 or 9.4 micrometers provided by a continuous wave CO.sub.2 laser. KC1 windows on the short path are to monitor infrared spectra of reactants and products. Nitrogen dioxide or nitric acid is present as the second reactant and the nitrating agent. The infrared laser-induced method far exceeds the yield of nitrated products found in the argon-ion laser-induced nitration of isobutane reported in the literature. Applicants' method at least equals the yield from thermally activated systems with a minimum formation of undesirable side products. A representative sample, 220 torr of gaseous butane, and 20 torr NO.sub.2 is irradiated in one experiment for 30 seconds with 75 W/cm.sup.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: March 13, 1990
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Ann E. Stanley, Susan E. Godbey
  • 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: 4709107
    Abstract: A method for preparing nitrones from mixtures of arylhydroxylamines and alkylhydroxylamines containing zinc oxide solids is provided which does not require filtration of the mixture prior to reaction. This is accomplished by introducing a dilute acid solution to the mixture so as to solubilize the zinc oxide powder. The hydroxylamines within solution may be reacted with an aldehyde to produce a nitrone where the dilute acid dissolves the zinc oxide.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: November 24, 1987
    Assignee: General Electric Company
    Inventors: Paul R. West, Gary C. Davis
  • 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: 4524226
    Abstract: A process for selectively forming nitro compounds by contacting, at elevated temperature and pressure and in a homogeneous gas phase, an aldehyde 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: June 18, 1985
    Assignee: W. R. Grace & Co.
    Inventors: Shu-Chieh P. Wang, Martin B. Sherwin
  • 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: 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: 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: 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: 4496783
    Abstract: Nitration of organic compounds and organic nitrogen compounds produced.Organic nitrogen compounds are formed in the vapor phase by organic radical formation by reaction of an organic compound with hydroxyl radicals derived from the reaction between hydrogen peroxide and nitrogen dioxide and the nitration of the organic radicals, suitably with nitrogen dioxide. The process may be conducted as a single stage process using an excess of nitrogen dioxide over that required for hydroxyl radical formation. The production of hydroxyl radicals is maximized by the use of a catalytic solid surface such as a solid acid or an acidic oxide or mixed oxide. The product may be a mixture of some or all of the nitrite, nitrate and nitro-derivative which may be used as such, e.g. as a fuel additive, as a source of the individual compounds or as a feedstock for a further synthesis.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: January 29, 1985
    Assignee: Interox Chemicals Limited
    Inventors: Ian M. Campbell, Donald L. Baulch, Gary J. Audley
  • Patent number: 4487988
    Abstract: Organic nitrogen compounds are formed in the vapor phase by organic radical formation by reaction of an organic compound, suitably an alkane, with hydroxyl radicals derived from the reaction between hydrogen peroxide and nitrogen dioxide and the nitration of the organic radicals, suitably with nitrogen dioxide. The process is conducted using a molecular oxygen additive which directs the reaction towards the formation of the nitrate corresponding to the organic compound which may predominate in the organic reaction products.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: December 11, 1984
    Assignee: Interox Chemicals Limited
    Inventors: Ian M. Campbell, Donald L. Baulch, Jonathan M. Chappel
  • Patent number: 4476336
    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 at least one carboxylic acid, preferably acetic acid.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: October 9, 1984
    Assignee: W. R. Grace & Co.
    Inventor: 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: 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: 4394220
    Abstract: It is the discovery of the present invention to provide an improved method of rectifying the crude production stream obtained by the vapor phase nitration of hydrocarbons by subjecting the absorber bottom mixture to extractive distillation with water.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: July 19, 1983
    Assignee: Angus Chemical Company
    Inventors: Richard S. Egly, Cecil E. Turnquist
  • 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: 4262157
    Abstract: Decarboxylation of carboxylic acids using diazabicycloalkenes and, if desired, also a simple copper salt, as the means for decarboxylation.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: April 14, 1981
    Assignee: Abbott Laboratories
    Inventors: Yuji Hori, Yoshiaki Nagano, Hiroshi Taniguchi
  • Patent number: 4260838
    Abstract: Nitroparaffins are made by nitration in the gaseous phase under pressure, ssibly in the presence of a gas containing oxygen. The reagent to be nitrated is a mixture containing a substantial amount of propane, the reaction temperature and pressure, the contact time and the quantitative ratios between the nitrating agent, the mixture to be nitrated and the oxygenated gas being selected so that the nitration reaction is conducted in a homogeneous gaseous phase. The process makes it possible to obtain a percentage of different nitroparaffins in response to industrial demand and further to use the cheapest raw materials at a given moment.
    Type: Grant
    Filed: March 30, 1979
    Date of Patent: April 7, 1981
    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