The Nitro Or Nitroso Is In A Compound Which Contains Hydroxy, Bonded Directly To Carbon, Or Ether Patents (Class 564/495)
  • Patent number: 8722936
    Abstract: A compound having formula (I) wherein R1, R2, R3, R4, R5 and R6 independently are hydrogen, C1-C10 alkyl, C5-C10 cycloalkyl, C6-C10 aryl or C7-C20 aralkyl; X is a difunctional group selected from the group consisting of C2-C20 alkyl, C5-C20 cycloalkyl, C6-C10 aryl, C8-C20 aryl alkyl, C4-C20 heteroalkyl or C10-C20 aryl heteroalkyl.
    Type: Grant
    Filed: October 8, 2010
    Date of Patent: May 13, 2014
    Assignee: ANGUS Chemical Company
    Inventor: Raymond John Swedo
  • Patent number: 8697915
    Abstract: A new class of compounds, namely diamino alcohols, is described, along with a process for their production and their use as dispersing additives for coating formulations.
    Type: Grant
    Filed: December 15, 2010
    Date of Patent: April 15, 2014
    Inventors: Asghar A. Peera, Ian A. Tomlinson
  • 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: 8674139
    Abstract: Provided is a process for making a tertiary aminoalcohol compound. The process comprises using an excess amount of a carbonyl compound in a condensation step between the carbonyl compound and a nitroalkane, and conducting a hydrogenation/alkylation step to produce the tertiary aminoalcohol. The process uses fewer steps than conventional processes.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: March 18, 2014
    Inventors: David W. Moore, Raymond J. Swedo, Asghar A. Peera
  • Patent number: 8480800
    Abstract: Provided are aminoalcohol compounds for use as neutralizing agents for paints and coatings. The compounds are of the formula (I): or salt thereof, wherein R1, R2, R3, R4, R5, and n are as defined herein. Also provided are precursors of the aminoalcohol compounds and processes for making and using them.
    Type: Grant
    Filed: December 1, 2010
    Date of Patent: July 9, 2013
    Inventors: Ian A. Tomlinson, Asghar A. Peera, George David Green
  • Publication number: 20130172622
    Abstract: Provided is a process for making a tertiary aminoalcohol compound. The process comprises using an excess amount of a carbonyl compound in a condensation step between the carbonyl compound and a nitroalkane, and conducting a hydrogenation/alkylation step to produce the tertiary aminoalcohol. The process uses fewer steps than conventional processes.
    Type: Application
    Filed: September 21, 2011
    Publication date: July 4, 2013
    Applicant: ANGUS CHEMICAL COMPANY
    Inventors: David W. Moore, Raymond J. Swedo, Asghar A. Peera
  • Publication number: 20120202934
    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: Application
    Filed: October 8, 2010
    Publication date: August 9, 2012
    Inventors: Ian Anthony Tomlinson, Glenn Nelson Robinson, Asghar Akber Peera
  • Publication number: 20120165521
    Abstract: A method for producing a polyamino-polyalcohol. The method comprises steps of: (a) combining an aminoalcohol of formula (I) with a nitro-diol of formula (II) to produce a nitro amino diol; and (b) contacting the nitro amino diol with a reducing agent capable of reducing aliphatic nitro groups.
    Type: Application
    Filed: December 12, 2011
    Publication date: June 28, 2012
    Inventors: Ian A. Tomlinson, Asghar A. Peera
  • Publication number: 20110152574
    Abstract: A new class of compounds, namely diamino alcohols, is described, along with a process for their production and their use as dispersing additives for coating formulations.
    Type: Application
    Filed: December 15, 2010
    Publication date: June 23, 2011
    Inventors: Asghar A. Peera, Ian A. Tomlinson
  • Publication number: 20110146536
    Abstract: Provided are aminoalcohol compounds for use as neutralizing agents for paints and coatings. The compounds are of the formula (I): or salt thereof, wherein R1, R2, R3, R4, R5, and n are as defined herein. Also provided are precursors of the aminoalcohol compounds and processes for making and using them.
    Type: Application
    Filed: December 1, 2010
    Publication date: June 23, 2011
    Inventors: Ian A. Tomlinson, Asghar A. Peera, George D. Green
  • 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
  • Patent number: 7453012
    Abstract: A process for the hydrogenation of compounds comprising nitrile or nitro functional groups to amine, aminonitrile or aminonitro compounds is provided. The process can be a continuous process conducted in the presence of a heterogeneous hydrogenation catalyst in divided form and a basic compound. The reaction can be conducted in a stirred reactor comprising an external loop for circulating the reaction mixture, allowing one portion of the hydrogenated products to be separated without withdrawing the catalyst, by using tangential filtration. The process may be especially useful in the hydrogenation of adiponitrile to an aminocapronitrile/hexamethylenediamine mixture.
    Type: Grant
    Filed: January 20, 2003
    Date of Patent: November 18, 2008
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Gérald Bocquenet, André Chesnais, Jean-Michel Desire, Philippe Leconte, Lionel Sever
  • Patent number: 7250534
    Abstract: A compound consists of a fractal-like, plain or organometallic array useful for energy storage devices. A dendrimer useful in the synthesis of the fractal-like compound includes a single ligating moiety bound to a surface of each quadrant of the dendrimer. A method of making metallo-based (macro) molecules includes the steps of combining monomers selected from the group consisting of bipyridal- and terpyridal-based ligands with connecting metals and self assembling macrocycles wherein the monomes are interconnected by the metals.
    Type: Grant
    Filed: July 20, 2000
    Date of Patent: July 31, 2007
    Assignee: University of South Florida
    Inventor: George R. Newkome
  • Patent number: 6509504
    Abstract: Disclosed is a method for preparing serinol (2-amino-1,3-proanediol). From nitromethane, para-formaldehyde and sodium hydroxide, 1-nitro-1,3-propanediol sodium salt is prepared as a medical intermediate. In a fixed bed, this intermediate is allowed to undergo the continuous hydrogenation of 2-nitro-1,3-propanediol sodium salt and methanol as shown in reaction (1). In addition to being simple, the method is economically favorable and affords the high yield and high purity of serinol.
    Type: Grant
    Filed: December 12, 2001
    Date of Patent: January 21, 2003
    Assignee: SK Corporation
    Inventors: Byong-Sung Kwak, Ki-Nam Chung, Choon-Gil Kim, Ki-Ho Koh
  • Patent number: 6262307
    Abstract: A shaped, activated metal, fixed-bed catalyst with a pore volume of 0.05 to 1 ml/g and an outer activated layer consisting of a sintered, finely-divided, catalyst alloy and optionally promoters. The catalyst alloy has metallurgical phase domains, resulting from the method of preparation of the alloy, in which the largest phase by volume has a specific interface density of more than 0.5 &mgr;m−1.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: July 17, 2001
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Andreas Freund, Monika Berweiler, Barbara Bender, Bernd Kempf
  • Patent number: 6140539
    Abstract: In a process for preparing amines, in which at least one compound containing at least one nitro group is reacted with hydrogen in the presence of a supported catalyst comprising, as catalytically active metal, nickel, if desired together with at least one metal of transition group I, V, VI and/or VIII, the reduced and stabilized supported catalyst comprises nickel crystallites having a bimodal nickel crystallite size distribution having maxima at 30-80 Angstrom and 81-150 Angstrom on a support comprising ZrO.sub.2, ZrO.sub.2 --HfO.sub.2 and/or SiO.sub.2 --ZrO.sub.2 and/or SiO.sub.2 --ZrO.sub.2 --HfO.sub.2 and in the reduced and passivated state has a nickel content of 60-80 percent by mass, an SiO.sub.2 content of 0-20 percent by mass, a ZrO.sub.2 content of 0-40 percent by mass, an HfO.sub.2 content of 0-4 percent by mass and after further reduction for one hour at 100.degree. C. has a degree of reduction of at least 70%.
    Type: Grant
    Filed: March 3, 2000
    Date of Patent: October 31, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Sander, Dietmar Peisker, Klaus Werner, Holger Braunsberg, Gunter Georgi, Ulrich Penzel
  • Patent number: 6069281
    Abstract: The invention relates to the preparation of organic nitrogen compounds, in particular of aminoalkanes, alkyloximes, alkylnitrones or mixtures thereof, which have only one nitrogen-functional group and no alcoholic hydroxyl groups in the molecule, from nitro-containing reaction products of polymers of C.sub.2 -C.sub.6 -olefins with an average degree of polymerization P=5-100 with nitrogen oxides or mixtures of nitrogen oxides and oxygen by hydrogenation of these reaction products. The invention also relates to particular mixtures of such aminoalkanes, alkyloximes and/or alkylnitrones and to individual compounds of these types themselves. The designated products are suitable as additives to fuels and lubricants.
    Type: Grant
    Filed: January 13, 1998
    Date of Patent: May 30, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kropp, Wolfgang Siegel, Boris Breitscheidel, Wolfgang Harder, Harald Schwahn, Wolfgang Reif
  • 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: 5618966
    Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: April 8, 1997
    Assignee: Pharm-Eco Laboratories, Incorporated
    Inventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
  • Patent number: 5220020
    Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5210309
    Abstract: The bis-homotris compounds 4-amino-4-[1-(3-hydroxy-propyl)]-1,7-heptanediol and 4-[1-(3-aminopropyl)]-4-[1-(3-hydroxypropyl)]-1, 7-heptanediol, and organic synthetic methods for their preparation are described. Unique multifunctional aminotriols, as well as their percursors, quaternary nitroalkanes are disclosed as building blocks for unimolecular micelles, as well as new series of cascade polymers. The quaternary nitro compounds which are disclosed allow the synthesis of a new aminotriol containing a quaternary carbon.
    Type: Grant
    Filed: March 9, 1992
    Date of Patent: May 11, 1993
    Assignee: University of South Florida
    Inventors: George R. Newkome, Charles N. Moorefield
  • Patent number: 5099067
    Abstract: The present invention relates to a method of converting .beta.-nitro compounds, specifically alcohols, into the corresponding hydroxy amines with retention of configuration by the use of ammonium formate.
    Type: Grant
    Filed: August 15, 1991
    Date of Patent: March 24, 1992
    Assignee: Northwestern University
    Inventors: Anthony G. M. Barrett, Christopher D. Spilling
  • Patent number: 5053545
    Abstract: A method of preparing an amino alcohol of the formula ##STR1## where R.sub.1 is H, lower alkyl or R.sub.2, R.sub.2 is R.sub.3 CHOH in which R.sub.3 is H, alkyl or aryl. R.sub.3 preferably is hydrogen, lower alkyl or monocyclic aryl such as phenyl. The inventive method involves the reaction of halonitroalcohol with hydrogen in the presence of methanol, a suitable buffering agent such as ammonia, and a hydrogenation catalyst to form amino alcohol salt, neutralizing the amino alcohol salt, and recovering the resultant amino alcohol.
    Type: Grant
    Filed: August 7, 1990
    Date of Patent: October 1, 1991
    Assignee: Angus Chemical Company
    Inventors: Thomas H. Marman, Vincent Nocito
  • Patent number: 4924029
    Abstract: A homogeneous catalytic hydrogenation of nitroalcohols to amino alcohols is described in which a solution of nitroalcohol is contacted with hydrogen under low temperatures and in the presence of a soluble complex of an organometallic compound of Rh, Ir, Pt or Pd and an organophosphine.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: May 8, 1990
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Stephen G. Harsy
  • Patent number: 4902831
    Abstract: Described is a process for preparing 1,2-diaminoethane having the formula ##STR1## where R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.7 -C.sub.15 aralkyl, unsubstituted or substituted aryl or heteroaryl or alternatively, R.sub.1 and R.sub.2 together with the carbon atom form a 3 to 12 member cycloalkyl group, or with a heteroatom form a 3 to 12 member heterocyclic group and R.sub.3 and R.sub.4 together with the nitrogen atom form a 3 to 12 member heterocyclic group, optionally including oxygen, sulfur or phosphorus as a second heteroatom, the process comprising: reacting a preformed Schiff base with a nitroalkane as a neat mixture in the presence of a catalytic amount of an inorganic base to form the 1-nitro-2-aminoethane intermediate, which was then hydrogenated to give 1,2-diaminoethane.
    Type: Grant
    Filed: November 9, 1987
    Date of Patent: February 20, 1990
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventors: Khuong H. X. Mai, Ghanshyam Patil
  • Patent number: 4448999
    Abstract: 2-Aminopropanediol-1,3 (serinol) can be prepared by hydrogenation of the alkali salt of 2-nitro-1,3-propanediol with assuredly high yields by maintaining a narrow range of temperatures of extending from 50.degree.-80.degree. C. by use of a cooling device.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: May 15, 1984
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Klaus Thewalt, Gunter Bison, Heinz Egger
  • Patent number: 4362856
    Abstract: Poly-(2-aminoalkyl)polyamine compounds are provided having the following formula: ##STR1## wherein: n is an integer of from 2 to about 12;R.sub.1 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms;R.sub.2 and R.sub.3 are each independently selected from H and a lower alkyl group containing from 1 to about 6 carbon atoms;R.sub.4 is selected from H and ##STR2## and R.sub.5 is selected from an amine terminated polyol moiety having a molecular weight of from about 150 to about 5,000, from about 2 to about 80 ether linkages, and a valence of from about 2 to about 12.
    Type: Grant
    Filed: September 16, 1981
    Date of Patent: December 7, 1982
    Assignee: Milliken Research Corporation
    Inventor: Edward W. Kluger