Carbon Double Bonded To The Nitrogen Patents (Class 44/420)
  • Patent number: 9447341
    Abstract: A process and apparatus provides for blending a heavy naphtha stream with a diesel stream to increase the yield of diesel. The diesel stream is recovered separately from a kerosene stream to leave the kerosene stream undiminished. The blended diesel provides a valuable composition.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: September 20, 2016
    Assignee: UOP LLC
    Inventors: Jeffrey M. Bray, Douglas G. Stewart, James P. Glavin, Xin X. Zhu
  • Patent number: 8852297
    Abstract: A method cleaning up internal components of a fuel injector for a diesel engine. The method includes operating a fuel injected diesel engine on a fuel composition that includes a major amount of diesel fuel and from about 5 to about 500 ppm by weight of a reaction product derived from (a) a hydrocarbyl substituted dicarboxylic acid, anhydride, or ester and (b) an amine compound or salt thereof of the formula wherein R is selected from the group consisting of hydrogen and a hydrocarbyl group containing from about 1 to about 15 carbon atoms, and R1 is selected from the group consisting of hydrogen and a hydrocarbyl group containing from about 1 to about 20 carbon atoms. The reaction product is characterized by a particular FTIR spectrum.
    Type: Grant
    Filed: April 24, 2012
    Date of Patent: October 7, 2014
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Scott D. Schwab, Julienne M. Galante-Fox
  • Patent number: 8758456
    Abstract: A diesel fuel, diesel fuel additive concentrate and method for improving the performance of fuel injectors for a diesel engine are provided. The diesel fuel includes a major amount of middle distillate fuel having a sulfur content of 15 ppm by weight or less; and a reaction product of (a) a hydrocarbyl substituted dicarboxylic acid or anhydride, and (b) an amine compound or salt thereof of the formula wherein R is selected from hydrogen and a hydrocarbyl group containing from about 1 to about 15 carbon atoms, and R1 is selected from hydrogen and a hydrocarbyl group containing from about 1 to about 20 carbon atoms, wherein the reaction product contains less than one equivalent of an amino triazole group per molecule of reaction product, and wherein the reaction product is present in an amount sufficient to improve the performance of diesel direct and/or indirect fuel injectors.
    Type: Grant
    Filed: September 22, 2011
    Date of Patent: June 24, 2014
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Julienne M. Galante-Fox
  • Publication number: 20130247450
    Abstract: A gasoline deposit control additive composition for use in a fuel comprising from about 70 to about 95 volume percent of hydrocarbons in the gasoline boiling range and from about 5 to about 30 volume percent of at least one alcohol, comprising the imine or tertiary amine product of the reaction between (a) at least one aldehyde or ketone or mixture thereof having the formula R16CHO, R16CH2CHO, R17(C=0)R18 or R17CH2(C=0)R18, wherein R16, R17, and R18 are the same or different and are each independently a straight or branched chain hydrocarbyl or aryl group that contains from 1 to 18 carbon atoms, and (b) a primary or secondary amine functionality.
    Type: Application
    Filed: May 16, 2013
    Publication date: September 26, 2013
    Applicant: BUTAMAX ADVANCED BIOFUELS LLC
    Inventor: Leslie R. Wolf
  • Patent number: 8465560
    Abstract: A gasoline deposit control additive composition for use in a fuel comprising from about 70 to about 95 volume percent of hydrocarbons in the gasoline boiling range and from about 5 to about 30 volume percent of at least one alcohol, comprising the imine or tertiary amine product of the reaction between (a) at least one aldehyde or ketone or mixture thereof having the formula R16 CHO, R16 CH2 CHO, R17 (C=0) R18 or R17 CH2 (C=0) R18, wherein R16, R17, and R18 are the same or different and are each independently a straight or branched chain hydrocarbyl or aryl group that contains from 1 to 18 carbon atoms, and (b) a primary or secondary amine functionality.
    Type: Grant
    Filed: February 1, 2010
    Date of Patent: June 18, 2013
    Assignee: Butamax Advanced Biofuels LLC
    Inventor: Leslie R. Wolf
  • Patent number: 8466319
    Abstract: A method for producing a nitrone of formula (I) wherein R is a branched alkyl group having from four to thirty carbon atoms; R1, R2, R3 and R4 independently are hydrogen or alkyl groups having from one to six carbon atoms from an imine having formula (II)
    Type: Grant
    Filed: November 9, 2012
    Date of Patent: June 18, 2013
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Manohar Banavali, Bharati Dinkar Chheda, Barry Weinstein
  • Patent number: 8461387
    Abstract: A method for producing a nitrone of formula (I) wherein R is a branched alkyl group having from four to thirty carbon atoms; R1, R2, R3 and R4 independently are hydrogen or alkyl groups having from one to six carbon atoms from an imine having formula (II)
    Type: Grant
    Filed: November 9, 2012
    Date of Patent: June 11, 2013
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Manohar Banavali, Bharati Dinkar Chheda, Barry Weinstein
  • Publication number: 20130065806
    Abstract: A method for producing a nitrone of formula (I) wherein R is a branched alkyl group having from four to thirty carbon atoms; R1, R2, R3 and R4 independently are hydrogen or alkyl groups having from one to six carbon atoms from an imine having formula (II)
    Type: Application
    Filed: November 9, 2012
    Publication date: March 14, 2013
    Applicant: ROHM AND HAAS COMPANY
    Inventor: Rohm and Haas Company
  • Patent number: 8329949
    Abstract: A method for producing a nitrone of formula (I) wherein R is a branched alkyl group having from four to thirty carbon atoms; R1, R2, R3 and R4 independently are hydrogen or alkyl groups having from one to six carbon atoms from an imine having formula (II)
    Type: Grant
    Filed: November 12, 2008
    Date of Patent: December 11, 2012
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Manohar Banavali, Bharati Dinkar Chheda, Barry Weinstein
  • Publication number: 20120102826
    Abstract: A diesel fuel additive composition, a fuel containing the fuel additive, a method for improving diesel engine performance using the additive. The diesel fuel additive includes a reaction product of (a) a hydrocarbyl-substituted acylating agent and (b) a reactant selected from the group consisting of a nitrogen-containing compound, a hydroxyl-containing compound, and water that provides a reaction product selected from the group consisting (1) a mono-amide/mono-acid or metal free mono-acid salt thereof, (2) a diacid or metal free diacid salt thereof, and (3) mono-ester/mono-acid or metal free mono-acid salt thereof. The reaction product includes at least about 10 molar percent acid groups based on total moles of the reaction product.
    Type: Application
    Filed: November 3, 2010
    Publication date: May 3, 2012
    Applicant: AFTON CHEMICAL CORPORATION
    Inventor: Xinggao FANG
  • Publication number: 20100236139
    Abstract: A fuel oil composition comprising a major amount of a fuel oil and a minor amount of a compound being the product of the 1,4-addition reaction of (i) ammonia, a primary or secondary hydrocarbyl-substituted amine or a mixture thereof to (ii) a species containing one or more ?,?-unsaturated carbonyl groups, wherein the compound includes at least one hydrocarbyl group containing at least 10 carbon atoms. The fuel oil composition has improved low temperature properties.
    Type: Application
    Filed: December 10, 2009
    Publication date: September 23, 2010
    Inventor: Graham Jackson
  • Patent number: 7582126
    Abstract: Compositions containing unsaturated fatty esters may be stabilized against atmospheric oxidation by the addition of an antioxidant package containing a phenolic oxidant and a nonphenolic oxygen scavenger, which may be a hydroxylamine, an amine N-oxide, an oxime, or a nitrone. If an amine N-oxide is used, it may be used with or without a phenolic antioxidant. Compositions treated in this manner show good resistance to atmospheric oxidation and resultant viscosity increase.
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: September 1, 2009
    Assignee: Arkema France
    Inventors: Nicholas Martyak, Michael Gernon, Conor Dowling, Daniel Alford
  • Publication number: 20090126263
    Abstract: A method for producing a nitrone of formula (I) wherein R is a branched alkyl group having from four to thirty carbon atoms; R1, R2, R3 and R4 independently are hydrogen or alkyl groups having from one to six carbon atoms from an imine having formula (II)
    Type: Application
    Filed: November 12, 2008
    Publication date: May 21, 2009
    Inventors: Rajiv Manohar Banavali, Bharati Dinkar Chheda, Barry Weinstein
  • Patent number: 7374588
    Abstract: A stable, substantially clear and homogeneous fuel composition contains an additive comprising a nitrogen donor and carrier, the nitrogen donor being present in an amount sufficient to reduce the NOx emissions of the fuel when subject to combustion and the carrier being selected to render the nitrogen donor soluble and to give the additive a molecular weight compatible with the energy properties of the fuel.
    Type: Grant
    Filed: May 2, 2001
    Date of Patent: May 20, 2008
    Assignee: Interfacial Technologies (UK) Limited
    Inventors: Ian Vernon Williamson, Clifford James Hazel
  • Publication number: 20040068922
    Abstract: A fuel additive composition includes a reaction product of a succinic acylating agent and a polyamine having at least one condensable primary amine group where the reaction product has a ratio of the imide to amide infrared carbonyl absorption peak areas of about 1:0.0-0.6 and a water content of about 0.3% or less by weight. The succinic acylating agent is prepared by thermal condensation of a highly reactive polyolefin with maleic anhydride or a reactive equivalent thereof. This fuel additive composition has a low chlorine content and is very effective in fuel compositions that include a normally liquid fuel in reducing deposits in the fuel intake system of an internal combustion engine.
    Type: Application
    Filed: July 28, 2003
    Publication date: April 15, 2004
    Inventors: Robert H. Barbour, David A. Duncan, David J. Moreton
  • Patent number: 6514298
    Abstract: Fuel additives comprise a compound having a group represented by the formula >C═=N—  (1). Also disclosed are fuel compositions containing such additives. The additives have a superior detergent effect to conventional gasoline detergents and an excellent detergency of the injection nozzles of a diesel engine and is free from being sludge.
    Type: Grant
    Filed: December 26, 2000
    Date of Patent: February 4, 2003
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Katsuhiko Haji, Masaki Nagao, Tadahide Sone
  • Publication number: 20010005957
    Abstract: Fuel additives comprise a compound having a group represented by the formula
    Type: Application
    Filed: December 26, 2000
    Publication date: July 5, 2001
    Applicant: Nippon Mitsubishi Oil Corporation
    Inventors: Katsuhiko Haji, Masaki Nagao, Tadahide Sone
  • Patent number: 5752990
    Abstract: Combustion chamber deposits and intake valve deposits in a spark ignition internal combustion engine which uses a liquid hydrocarbon or liquid hydrocarbon-oxygenate fuel, by using an unleaded fuel to which has been added an additive selected from the group consisting of low boiling alkyl pyridines, 4-vinylpyridine, DMF, N-formylpiperidine, sulfolane, polyolefin, polyether or polyether amine derivatives of DMF, amidene, or N-substituted-2 pyrrolidones, polyolefin in an amount of at least about 1,000 wppm and mixtures thereof. Functionalized polymer detergents can be used alone and added to the fuels in amounts in of about at least 3,000 wppm.
    Type: Grant
    Filed: March 29, 1996
    Date of Patent: May 19, 1998
    Assignee: Exxon Research and Engineering Company
    Inventors: Michael Siskin, Simon Robert Kelemen
  • Patent number: 5567212
    Abstract: A method for scavenging sulfur species from a petroleum-derived medium is disclosed. The method comprises contacting the medium with sulfur species scavenging amount of an imine of the formula ##STR1## wherein x is an integer from 1 to 10, R' is an organic moiety having a number of valences equal to x, R.sub.1 is hydrogen or a mono-valent organic moieties and R is a mono-valent olefin moiety, provided that R and R.sub.1 contain a total of from about four to about forty carbon atoms. In an alternative embodiment, the imine is produced by a condensation reaction between an amine having at least one primary amino group and a carbonyl of the formula ##STR2## wherein R.sub.1 is hydrogen or a mono-valent organic moieties and R is a mono-valent olefin moiety, provided that R and R.sub.1 contain a total of from about four to about forty carbon atoms.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: October 22, 1996
    Assignee: Petrolite Corporation
    Inventors: David R. Gentry, Gerald T. Pancio, Jerry J. Weers
  • Patent number: 5567213
    Abstract: A method for scavenging sulfur species from a petroleum-derived medium is disclosed. The method comprises contacting the medium with sulfur species scavenging amount of an imine of the formula ##STR1## wherein x is an integer from 1 to 10, R' is an organic moiety having a number of valences equal to x, R.sub.1 is hydrogen or a mono-valent organic moieties and R is a mono-valent olefin moiety, provided that R and R.sub.1 contain a total of from about four to about forty carbon atoms. In an alternative embodiment, the imine is produced by a condensation reactionic between an amine having at least one primary amino group and a carbonyl of the formula ##STR2## wherein R.sub.1 is hydrogen or a mono-valent organic moieties and R is a mono-valent olefin moiety, provided that R and R.sub.1 contain a total of from about four to about forty carbon atoms.
    Type: Grant
    Filed: April 25, 1996
    Date of Patent: October 22, 1996
    Assignee: Petrolite Corporation
    Inventors: David R. Gentry, Gerald T. Pancio, Jerry J. Weers
  • Patent number: 5372614
    Abstract: A sludge dispersing agent for fuel oils includes a polymer having at least one >C.dbd.N.sup.+ < bond in its molecule and at least one compound selected from the group consisting of long-chain alkyl phosphates and alkyl sulfosuccinates and salts thereof.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: December 13, 1994
    Assignees: Nippon Zeon Co., Ltd., Nippon Oil Company
    Inventors: Shizuo Kitahara, Kazuhisa Kanefuji, Akio Oda, Hiromoto Inoura, Shigeru Kinomoto
  • Patent number: 5266080
    Abstract: The flame luminosity of a methanol fuel is appreciably enhanced by the addition thereto of at least one flame luminosity enhancing agent selected from the group consisting of azine dye, triarylmethane dye, fluorescein dye, imine dye and anthraquinone dye, said dye excluding any metal component whose combustion product(s) tend to cause excessive wear in an engine operated with the fuel composition or tend to significantly interfere with normal operation of such engine or any of its associated systems, the flame luminosity of the fuel composition during burning being appreciably enhanced relative to the flame luminosity of the same burning fuel composition but to which no flame luminosity enhancing agent has been added.
    Type: Grant
    Filed: October 11, 1989
    Date of Patent: November 30, 1993
    Assignee: The Standard Oil Company
    Inventors: Thomas E. Kiovsky, Wendy L. Clark
  • Patent number: 5169411
    Abstract: Hydrogen sulfide gas evolution during storage or transport of petroleum residua is suppressed by the incorporation of an effective amount of certain imines.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: December 8, 1992
    Assignee: Petrolite Corporation
    Inventor: Jerry J. Weers
  • Patent number: 5162049
    Abstract: This invention relates to stabilizer additives for hydrocarbonaceous fuels comprising at least one or a mixture of hexahydrotriazine compounds and at least one or a mixture of imine compounds.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: November 10, 1992
    Assignee: Ethyl Petroleum Additives
    Inventors: John G. Bostick, Lawrence J. Cunningham
  • Patent number: 5152807
    Abstract: Sediment and color formation in diesel and heating fuel oils, especially those comprising a cracked fraction, may be reduced by incorporating in the fuel oil a guanidinium or substituted guanidinium salt.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: October 6, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Michael D. Sexton, Rosalind H. Strange
  • Patent number: 5100532
    Abstract: 2'-hydroxy-4' or 5'-alkylacetophenone oximes and 2-hydroxy-4 or 5-alkylbenzaldehyde oximes are used to deactivate iron species contained in hydrocarbon fluids. Left untreated, iron leads to decomposition of the hydrocarbon, resulting in the formation of gummy, polymer masses in the hydrocarbon liquid.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: March 31, 1992
    Assignee: Betz Laboratories, Inc.
    Inventors: Paul V. Roling, John E. Martin
  • Patent number: 5032144
    Abstract: The octane value of fuels such as gasoline is increased by adding thereto an organic compound containing a tert-butyl group bonded to a carbon or nitrogen atom, which, in turn, is bonded to yet another atom by double or triple bonds.
    Type: Grant
    Filed: August 4, 1988
    Date of Patent: July 16, 1991
    Assignee: Union Oil Company of California
    Inventors: Peter J. Jessup, Stephen G. Brass, Michael C. Croudace