Halogen Containing Patents (Class 585/359)
  • Patent number: 10160707
    Abstract: The present invention describes a novel process for preparing 3-chloro-2-vinylphenol which, owing to the chemoselectivity achieved, also allows direct conversion into (3-chloro-2-vinylphenyl)methane-sulphonate.
    Type: Grant
    Filed: June 8, 2015
    Date of Patent: December 25, 2018
    Assignee: Bayer CropScience Aktiengesellschaft
    Inventors: Florian Erver, Mark James Ford
  • Patent number: 8802908
    Abstract: Process and systems for alkane bromination and, in one or more embodiments, to separate, parallel methane and higher alkanes bromination in a bromine-based process. An embodiment discloses a bromine-based process for converting alkanes to liquid hydrocarbons that includes alkanes bromination, the process comprising: brominating a methane stream comprising methane and having less than about 2 mol % of ethane to form methane bromination products comprising brominated methane and a first fraction of hydrogen bromide; separately brominating a C2+ alkane stream comprising an alkane having 2 or more carbon atoms to form C2+ methane bromination products comprising brominated alkanes having 2 or more carbon atoms and a second fraction of hydrogen bromide; and catalytically reacting at least a portion of the brominated methane and the brominated alkanes to form higher molecular hydrocarbons.
    Type: Grant
    Filed: October 8, 2012
    Date of Patent: August 12, 2014
    Assignee: Marathon GTF Technology, Ltd.
    Inventors: John J. Waycullis, Sagar B. Gadewar, Raphael Thomas
  • Patent number: 8692042
    Abstract: This invention relates to methods for producing cycloheptatriene from at least 7,7-dichloronorcarane and a liquid component comprising a C8 to C30 succinic anhydride, a carboxylic acid, or a C8 to C30 alkyldimethylamine at about 205 deg. C. to about 230 deg. C.
    Type: Grant
    Filed: February 22, 2011
    Date of Patent: April 8, 2014
    Assignee: Albemarle Corporation
    Inventors: Richmond M. Starrett, Christopher D. Claeboe, Anthony F. Skufca, Joseph H. Miller
  • Patent number: 8642822
    Abstract: A process for converting gaseous alkanes to olefins, higher molecular weight hydrocarbons or mixtures thereof wherein a gaseous feed containing alkanes may be thermally or catalytically reacted with a dry bromine vapor to form alkyl bromides and hydrogen bromide. Poly-brominated alkanes present in the alkyl bromides may be further reacted with methane over a suitable catalyst to form mono-brominated species. The mixture of alkyl bromides and hydrogen bromide may then be reacted over a suitable catalyst at a temperature sufficient to form olefins, higher molecular weight hydrocarbons or mixtures thereof and hydrogen bromide. Various methods and reactions are disclosed to remove the hydrogen bromide from the higher molecular weight hydrocarbons, to generate bromine from the hydrogen bromide for use in the process, to store and subsequently release bromine for use in the process, and to selectively form mono-brominated alkanes in the bromination step.
    Type: Grant
    Filed: May 27, 2011
    Date of Patent: February 4, 2014
    Assignee: Marathon GTF Technology, Ltd.
    Inventors: Raymond T. Brickey, Greg A. Lisewsky, John J. Waycuilis, Stephen D. York
  • Patent number: 8536393
    Abstract: The present invention provides an integrated process for producing aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons from low molecular weight alkanes, which includes contacting the low molecular weight alkanes with a halogen and coupling the monohaloalkanes to form aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons.
    Type: Grant
    Filed: May 11, 2010
    Date of Patent: September 17, 2013
    Assignee: Shell Oil Company
    Inventors: Wayne Errol Evans, Glenn Charles Komplin, Duraisamy Muthusamy
  • Patent number: 8367884
    Abstract: Processes and systems for synthesizing hydrocarbon products, such as high molecular weight hydrocarbons, olefins or mixtures thereof, from alkyl bromides wherein one or more streams of alkyl bromides may be reacted in sequential or concurrent stages at different temperatures. The catalyst used in the synthesis stages may be the same or different and at least in one instance is chosen to form hydrocarbon products having a significant C6+ paraffin content. The stages may be conducted in one or more reactors and the catalyst may be deployed in fixed beds or fluidized beds.
    Type: Grant
    Filed: February 17, 2011
    Date of Patent: February 5, 2013
    Assignee: Marathon GTF Technology, Ltd.
    Inventor: John J Waycuilis
  • Patent number: 8278493
    Abstract: A method of synthesizing hydrocarbons from smaller hydrocarbons includes the steps of hydrocarbon halogenation, simultaneous oligomerization and hydrogen halide neutralization, and product recovery, with a metal-oxygen cataloreactant used to facilitate carbon-carbon coupling. Treatment with air or oxygen liberates halogen and regenerates the cataloreactant.
    Type: Grant
    Filed: May 13, 2011
    Date of Patent: October 2, 2012
    Assignee: GRT, Inc.
    Inventor: Ivan M. Lorkovic
  • Patent number: 8232441
    Abstract: A process for converting gaseous alkanes to liquid hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as a ZSM-5 zeolite, at a temperature of from about 150° C. to about 450° C. so as to form higher molecular weight hydrocarbons and hydrobromic acid vapor. Propane and butane which comprise a portion of the products may be recovered or recycled back through the process to form additional C5+ hydrocarbons. Various methods are disclosed to remove the hydrobromic acid vapor from the higher molecular weight hydrocarbons and to generate bromine from the hydrobromic acid for use in the process.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: July 31, 2012
    Assignee: Marathon GTF Technology, Ltd.
    Inventor: John J. Waycuilis
  • Patent number: 8198495
    Abstract: Processes and systems for synthesizing alkyl bromides to hydrocarbon products, such as high molecular weight hydrocarbons, olefins or mixtures thereof, wherein one or more streams of alkyl bromides may be synthesized in sequential or concurrent stages at different temperatures. The catalyst used in the synthesis stages may be the same or different and at least in one instance is chosen to form hydrocarbon products having a significant C6+ paraffin content. The stages may be conducted in one or more reactors and the catalyst may be deployed in fixed beds or fluidized beds.
    Type: Grant
    Filed: March 2, 2010
    Date of Patent: June 12, 2012
    Assignee: Marathon GTF Technology, Ltd.
    Inventors: John J. Waycuilis, William J. Turner
  • Patent number: 8173851
    Abstract: A process for converting gaseous alkanes to olefins, higher molecular weight hydrocarbons or mixtures thereof wherein a gaseous feed containing alkanes is thermally reacted with a dry bromine vapor to form alkyl bromides and hydrogen bromide. Poly-brominated alkanes present in the alkyl bromides are further reacted with methane over a suitable catalyst to form mono-brominated species. The mixture of alkyl bromides and hydrogen bromide is then reacted over a suitable catalyst at a temperature sufficient to form olefins, higher molecular weight hydrocarbons or mixtures thereof and hydrogen bromide. Various methods are disclosed to remove the hydrogen bromide from the higher molecular weight hydrocarbons, to generate bromine from the hydrogen bromide for use in the process, and to selectively form mono-brominated alkanes in the bromination step.
    Type: Grant
    Filed: June 3, 2009
    Date of Patent: May 8, 2012
    Assignee: Marathon GTF Technology, Ltd.
    Inventors: John J. Waycuilis, William J. Turner, Raphael Thomas
  • Patent number: 8008535
    Abstract: A process for converting gaseous alkanes to olefins and higher molecular weight hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as an X or Y type zeolite, at a temperature of from about 250° C. to about 500° C. so as to form olefins, higher molecular weight hydrocarbons and hydrobromic acid vapor. Various methods are disclosed to remove the hydrobromic acid vapor from the olefins and higher molecular weight hydrocarbons and to generate bromine from the hydrobromic acid for use in the process.
    Type: Grant
    Filed: April 30, 2008
    Date of Patent: August 30, 2011
    Assignee: Marathon GTF Technology, Ltd.
    Inventor: John J. Waycuilis
  • Patent number: 7964764
    Abstract: A method of synthesizing hydrocarbons from smaller hydrocarbons includes the steps of hydrocarbon halogenation, simultaneous oligomerization and hydrogen halide neutralization, and product recovery, with a metal-oxygen cataloreactant used to facilitate carbon-carbon coupling. Treatment with air or oxygen liberates halogen and regenerates the cataloreactant.
    Type: Grant
    Filed: January 7, 2010
    Date of Patent: June 21, 2011
    Assignee: GRT, Inc.
    Inventor: Ivan M. Lorkovic
  • Patent number: 7847139
    Abstract: A method of synthesizing hydrocarbons from smaller hydrocarbons includes the steps of hydrocarbon halogenation, simultaneous oligomerization and hydrogen halide neutralization, and product recovery, with a metal-oxygen cataloreactant used to facilitate carbon-carbon coupling. Treatment with air or oxygen liberates halogen and regenerates the cataloreactant.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: December 7, 2010
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Ivan M. Lorkovic, Maria Noy, Jeffrey H. Sherman, Michael J. Weiss, Galen D. Stucky
  • Patent number: 7834228
    Abstract: Synthesis of mono-substituted alkylcyclopentadienes by mixing alkyl iodides with cyclopentadienyl magnesium chloride in tetrahydrofuran is described.
    Type: Grant
    Filed: June 16, 2006
    Date of Patent: November 16, 2010
    Assignee: Boulder Scientific Company
    Inventors: Karin A. Voll Barclay, Richard D. Crawford, Dawn A. Arkin, Daniel A. Gately
  • Patent number: 7674941
    Abstract: A process for converting gaseous alkanes to olefins, higher molecular weight hydrocarbons or mixtures thereof wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid is then reacted over a suitable catalyst at a temperature sufficient to form olefins, higher molecular weight hydrocarbons or mixtures thereof and hydrobromic acid vapor. Various methods are disclosed to remove the hydrobromic acid vapor from the higher molecular weight hydrocarbons, to generate bromine from the hydrobromic acid for use in the process, and to selectively form monobrominated alkanes in the bromination step.
    Type: Grant
    Filed: June 13, 2008
    Date of Patent: March 9, 2010
    Assignee: Marathon GTF Technology, Ltd.
    Inventors: John J. Waycuilis, William J. Turner
  • Patent number: 7560607
    Abstract: A process for converting gaseous alkanes to liquid hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as a ZSM-5 zeolite, at a temperature of from about 150° C. to about 450° C. so as to form higher molecular weight hydrocarbons and hydrobromic acid vapor. Propane and butane which comprise a portion of the products may be recovered or recycled back through the process to form additional C5+ hydrocarbons. Various methods are disclosed to remove the hydrobromic acid vapor from the higher molecular weight hydrocarbons and to generate bromine from the hydrobromic acid for use in the process.
    Type: Grant
    Filed: December 14, 2007
    Date of Patent: July 14, 2009
    Assignee: Marathon GTF Technology, Ltd.
    Inventor: John J. Waycuilis
  • Publication number: 20080275279
    Abstract: An oxidative halogenation process involving contacting methane, a C1 halogenated hydrocarbon, or a mixture thereof with a source of halogen and a source of oxygen, at a molar ratio of reactant hydrocarbon to source of halogen in a feed to the reactor greater than 23/1, and/or at a molar ratio of reactant hydrocarbon to source of oxygen in a feed to the reactor greater than about 46/1; in the presence of a rare earth halide or rare earth oxyhalide catalyst, to produce a halogenated C1 product having at least one more halogen as compared with the C1 reactant hydrocarbon, preferably, methyl chloride. The process can be advantageously conducted to total conversion of source of halogen and source of oxygen. The process can be advantageously conducted with essentially no halogen in the feed to the reactor, by employing a separate catalyst halogenation step in a pulse, swing or circulating bed mode.
    Type: Application
    Filed: April 25, 2006
    Publication date: November 6, 2008
    Inventors: Simon G. Podkolzin, Eric E. Stangland, Albert E. Schweizer, Mark E. Jones
  • Patent number: 7420097
    Abstract: The present invention provides a method of making fulvenes, particularly 6-aryl-6-alkylfulvenes, 6-aryl-6-alkenylfulvenes, and related compounds, by combining alkyl- or alkenyl-arylketones with magnesium cyclopentadienyl reagents in nonprotic, including ethereal, solvents. The use of these compounds in preparing bis(cyclopentadienyl)methanes and related compounds, and ansa-metallocenes, is disclosed.
    Type: Grant
    Filed: June 25, 2004
    Date of Patent: September 2, 2008
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Matthew G. Thorn, Michael D. Jensen, Joel L. Martin, Qing Yang, James L. Smith
  • Patent number: 7348464
    Abstract: A process for converting gaseous alkanes to liquid hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as a ZSM-5 zeolite, at a temperature of from about 150° C. to about 450° C. so as to form higher molecular weight hydrocarbons and hydrobromic acid vapor. Propane and butane which comprise a portion of the products may be recovered or recycled back through the process to form additional C5+ hydrocarbons. Various methods are disclosed to remove the hydrobromic acid vapor from the higher molecular weight hydrocarbons and to generate bromine from the hydrobromic acid for use in the process.
    Type: Grant
    Filed: April 8, 2005
    Date of Patent: March 25, 2008
    Assignee: Marathon Oil Company
    Inventor: John J. Waycuilis
  • Patent number: 7244867
    Abstract: A process for converting gaseous alkanes to liquid hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as a ZSM-5 zeolite, at a temperature of from about 150° C. to about 400° C. so as to form higher molecular weight hydrocarbons and hydrobromic acid vapor. Hydrobromic acid vapor is removed from the higher molecular weight hydrocarbons. A portion of the propane and butane is removed from the higher molecular weight hydrocarbons and reacted with the mixture of alkyl bromides and hydrobromic acid over the synthetic crystalline alumino-silicate catalyst to form C5+ hydrocarbons.
    Type: Grant
    Filed: April 16, 2004
    Date of Patent: July 17, 2007
    Assignee: Marathon Oil Company
    Inventor: John J. Waycuilis
  • Patent number: 6552239
    Abstract: The present invention relates to a process for the preparation of cyclopropaneacetylene by reacting a ketophosphonate with a diazo-transfer reagent in the presence of non-nucleophilic base in an aprotic solvent to generate a reaction mixture containing a ketodiazophosphonate compound and then reacting the reaction mixture with cyclopropanecarboxaldehyde in a non-nucleophilic base and a protic solvent to yield cyclopropaneacetylene.
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: April 22, 2003
    Assignee: Merck & Co., Inc.
    Inventor: Karel M. J. Brands
  • Patent number: 6528693
    Abstract: 1-chloropropylethyne is prepared by dehydrochlorination with a base of 1-chloro-1-cyclopropylethene, which is itself prepared by treating 1-cyclopropylethanone with dichlorotriarylphosphorane or dichlorotrialkylphosphorane in the presence of a base.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: March 4, 2003
    Assignee: Great Lakes (UK) Limited
    Inventors: Robert Gandy, Peter John Cremins, Allan Williams Timms
  • Patent number: 6414206
    Abstract: The present invention relates to a process for preparing bisindenylalkanes of formula I: wherein R1, R2, R3, and R4 independently represent H or a C1-C6 hydrocarbon group or R1 and R2 or R1 and R3 or R3 and R4 together with the carbon atoms to which they are attached form a saturated or unsaturated 5- or 6-membered ring, said ring being optionally substituted with a C1-C4 hydrocarbon group, and R5 represents a C1-C6 hydrocarbon group, comprising reacting, at a temperature which does not exceed about 5° C., a metallated indene of formula II with a disubstituted hydrocarbon of formula III: wherein R1, R2, R3, R4, and R5 have the same meaning as defined above, M represents a metal ion, and X independently represents a suitable leaving group, in a suitable reaction medium wherein the molar ratio of II to III is 2.05 or higher. The process is particularly suitable for preparing bisindenylethane, i.e., R1-R4 represent H and R5 represents an ethylene group.
    Type: Grant
    Filed: February 22, 2001
    Date of Patent: July 2, 2002
    Assignee: Akzo Nobel NV
    Inventors: Richard Herman Woudenberg, Faysal Kalmoua
  • Patent number: 6388151
    Abstract: A method for synthesizing tetramethylcyclopentadiene from 2,3-dibromobutane is described. A 2-bromo-2-butene Grignard is reacted with an ethyl formate to produce a 3,5-dimethyl-2,5-heptadiene-4-ol magnesium bromide which is then quenched with acetic acid to produce 3,5-dimethyl-2,5-hepadiene-4-ol.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: May 14, 2002
    Assignee: Boulder Scientific Company
    Inventors: Jeffrey M. Sullivan, Richard D. Crawford
  • Patent number: 6359164
    Abstract: The present invention relates generally to novel methods for the preparation of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor with superior anti-retroviral activity. In the process, for example, cyclopropane carboxaldehyde is alkylated to form 1,1,1-trichloro-2-cyclopropyl-ethanol; which in turn undergoes elimination to form 1,1-dichloro-2-cyclopropyl-ethene; which in turn undergoes elimination to form cyclopropyl acetylene.
    Type: Grant
    Filed: September 30, 1999
    Date of Patent: March 19, 2002
    Inventors: Zhe Wang, Joseph M. Fortunak
  • Publication number: 20010051756
    Abstract: The present invention relates to a method to prepare cyclopropenes.
    Type: Application
    Filed: April 4, 2001
    Publication date: December 13, 2001
    Inventor: Richard Martin Jacobson
  • Patent number: 6297410
    Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor. In the process, cyclopropane carboxaldehyde is condensed with malonic acid to form 3-cyclopropylacrylic acid; 3-cyclopropylacrylic acid is halogenated to form (E,Z)-1-halo-2-cyclopropylethylene; and (E,Z)-1-halo-2-cyclopropylethylene is dehydrohalogenated to form cyclopropyl acetylene. This improvement provides for high conversion of inexpensive, readily available starting materials into cyclopropylacetylene, high overall yields and can be conducted on an industrial scale.
    Type: Grant
    Filed: January 12, 2000
    Date of Patent: October 2, 2001
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Joseph M. Fortunak, Zhe Wang, Jianguo Yin
  • Patent number: 6288297
    Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor. In the process, for example, cyclopropane carboxaldehyde is alkylated to form 1,1,1-trichloro-2-cyclopropyl-ethanol; which in turn is hydroxy protected to form 1,1,1-trichloro-2-cyclopropylethyltosylate; which in turn undergoes elimination to form cyclopropyl acetylene. This improvement provides for high conversion of inexpensive, readily available starting materials into cyclopropylacetylene, high overall yields and can be conducted on an industrial scale.
    Type: Grant
    Filed: September 30, 1999
    Date of Patent: September 11, 2001
    Assignee: Dupont Pharmaceuticals Company
    Inventors: Zhe Wang, Jianguo Yin, Joseph M. Fortunak, Silvio Campagna
  • Patent number: 6232516
    Abstract: The process for the preparation of a selectively substituted cyclopentadiene compound which includes reacting a halide of a substituting compound in a mixture of the cyclopentadiene compound and an aqueous solution of a base in the presence of a phase transfer catalyst, wherein during the reaction the quantity of base relative to the cyclopentadiene compound may at any moment be between 5 and 30 mol/mol.
    Type: Grant
    Filed: May 2, 1997
    Date of Patent: May 15, 2001
    Assignee: DSM N.V.
    Inventors: Johannes A. M. van Beek, Gerardus J. M. Gruter, Richard Green
  • Patent number: 6207864
    Abstract: The invention relates to a process for the halogenation of cyclopropylmethyl ketone with at least one dihalo-triorganophosphorane of the general formula I R3PHal2   (I), in which the radicals R can be the same or different and denote a saturated or unsaturated aliphatic C1-C20 hydrocarbon radical, a phenyl or (C1-C4 alkyl)phenyl radical, which may be optionally substituted by one or two fluorine, chlorine and/or nitro groups, P stands for phosphorus and Hal denotes chlorine, bromine, or iodine, at a temperature of from 800° to 130° C.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: March 27, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Henningsen, Armin Stamm, Martin Fischer, Wolfgang Siegel
  • Patent number: 6072094
    Abstract: An efficient and facile process for the preparation of cyclopropylacetylene from thioanisole and cyclopropyl substituted ketones or aldehydes is disclosed.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: June 6, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Sandor Karady, Benjamin Marcune
  • Patent number: 6049019
    Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor. In the process, cyclopropane carboxaldehyde is condensed with malonic acid to form 3-cyclopropylacrylic acid; 3-cyclopropylacrylic acid is halogenated to form (E,Z)-1-halo-2-cyclopropylethylene; and (E,Z)-1-halo-2-cyclopropylethylene is dehydrohalogenated to form cyclopropyl acetylene. This improvement provides for high conversion of inexpensive, readily available starting materials into cyclopropylacetylene, high overall yields and can be conducted on an industrial scale.
    Type: Grant
    Filed: July 30, 1998
    Date of Patent: April 11, 2000
    Assignee: DuPont Pharmaceuticals
    Inventors: Joseph M. Fortunak, Zhe Wang, Jianguo Yin
  • Patent number: 6028237
    Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is a reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one which is a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
    Type: Grant
    Filed: December 15, 1997
    Date of Patent: February 22, 2000
    Assignee: DuPont Pharmaceuticals Company
    Inventor: Rodney Lawrence Parsons, Jr.
  • Patent number: 5973092
    Abstract: A thermosetting resin is formed from cyclopentadiene and a propargyl halide. The resin can be used with carbon fibers to form a carbon-carbon composite.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: October 26, 1999
    Assignee: The University of Southern Mississippi
    Inventors: Lon J. Mathias, Gregory J. Tregre
  • Patent number: 5952537
    Abstract: The process of invention reacts an alkynyl halide with a mixture that includes a dialkylaminomagnesium halide or a bis(dialkylamino)magnesium compound to produce a cycloalkylacetylene compound. Preferably, the dialkylaminomagnesium halide compound is of the general formula R.sub.2 NMgX (where R is a linear, branched, or cyclic alkyl substituent or R.sub.2 N represents a heterocyclic alkyl amine and X is Cl, Br, or I) and the bis(dialkylamino)magnesium compound is of the general formula (R.sub.2 N).sub.2 Mg (where R is a linear, branched, or cyclic alkyl substituent or R.sub.2 N represents a heterocyclic alkylamine). In a preferred method of the invention, the reaction is conducted at moderate temperatures for a period of about 12 to 24 hours. The reaction mixture preferably includes tetrahydrofuran (THF), or a hydrocarbon, or a hydrocarbonether mixture.
    Type: Grant
    Filed: March 13, 1998
    Date of Patent: September 14, 1999
    Assignee: Wiley Organics, Inc.
    Inventors: Kurt R. Stickley, David B. Wiley
  • Patent number: 5773549
    Abstract: The invention provides a process for hydrotreating an organic feedstock containing a halogenated component and contaminated with distillable oxygen compounds, and/or distillable nitrogen compounds having boiling points lower than the halogenated compounds by means of removing the distillable oxygen compounds and distillable nitrogen compounds with a fractionation zone and then contacting the resulting organic feedstock having a reduced concentration of distillable oxygen and nitrogen compounds and a gaseous recycle stream containing hydrogen with a hydrogenation catalyst in a hydrogenation reaction zone to produce an anhydrous liquid stream comprising hydrogenated hydrocarbonaceous compounds having a reduced concentration of organic halide and a hydrogen halide compound. The resulting effluent from the hydrogenation zone is optionally separated to produce a hydrogenated hydrocarbonaceous stream having a reduced level of halogen and an anhydrous stream comprising a hydrogen halide compound.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: June 30, 1998
    Assignee: UOP LLC
    Inventors: Mark D. Moser, Tom N. Kalnes, Chwu-Ching Jan
  • Patent number: 5663467
    Abstract: An improved synthesis of cyclopropylacetylene involving cyclization of 5-halo-1-pentyne in strong base is disclosed, and is useful for preparing compounds with a cyclopropylethynyl substituent, such as an intermediate for a highly potent HIV reverse transcriptase inhibitor or other pharmaceutically active compounds.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: September 2, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Andrew S. Thompson, Edward G. Corley, Martha Huntington
  • Patent number: 5616752
    Abstract: A method is provided for forming a supported cyclopentadiene-type compound comprising contacting a cyclopentadiene-type compound containing an active halogen with an inorganic support having surface hydroxyl group. Also there is provided a method of preparing a supported metallocene comprising reacting the supported cyclopentadiene-type compound with a transition metal compound under suitable conditions. There is also provided a process for producing bridged cyclopentadiene-type ligands having a bridge having branch that has a terminal vinyl group. Also metallocenes of these ligands are provided. Still further there is provided a process for producing bridged cyclopentadiene-type ligands having a bridge having a branch that has a terminal active halogen. The resulting new ligands and supported metallocenes produced therefrom are also provided.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 1, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Konstantinos Patsidis, Bernd Peifer, Helmut G. Alt, Rolf L. Geerts, Darryl R. Fahey, M. Bruce Welch, Syriac J. Palackal, Harold R. Deck
  • Patent number: 5446225
    Abstract: An alkylative cycloaddition method is provided that is particularly useful for the synthesis of many of the Vitamin D analogues with differing side chains. Thus, a preferred synthesis is of Vitamin D analogues having a side chain R.sub.1 where a first precursor having the structure ##STR1## with X being a halide or a pseudo halide, and a second precursor are provided, the second precursor being a 1,7 enyne. These precursors are reacted in the presence of a palladium catalyst to form compounds having the structure ##STR2## where R.sub.2 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group, and R.sub.3 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: August 29, 1995
    Assignee: Board of Trustees of the Leland Stanford Junior Univ.
    Inventors: Barry M. Trost, Jacques Dumas
  • Patent number: 5401894
    Abstract: A process for the conversion of a halogenated organic feedstock to produce a stream of hydrocarbonaceous compounds having an exceedingly low concentration of halogenated organic compounds and an aqueous stream containing hydrogen halide.
    Type: Grant
    Filed: June 7, 1994
    Date of Patent: March 28, 1995
    Assignee: UOP
    Inventors: Robert S. Brasier, Robert B. James, Jr.
  • Patent number: 5396006
    Abstract: Preparation of alkenes as well as of cyclopentane and cyclohexane from the corresponding vicinal dichloro and dibromo alkanes and from .alpha.,.omega.-Dichloropentane and .alpha.,.omega.-dibromopentane and .alpha.,.omega.-dichlorohexane and .alpha.,.omega.-dibromohexane respectively, in which these starting compounds are caused to react with with silicon.
    Type: Grant
    Filed: October 18, 1993
    Date of Patent: March 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Wettling, Jochem Henkelmann
  • Patent number: 5292977
    Abstract: An alkylative cycloaddition method is provided that is particularly useful for the synthesis of many of the Vitamin D analogues with differing side chains. Thus, a preferred synthesis is of Vitamin D analogues having a side chain R.sub.1 where a substantially geometrically pure first precursor having the structure ##STR1## and a second precursor are provided, the second precursor being a 1,7 enyne. These precursors are reacted in the presence of a palladium catalyst to form compounds having the structure ##STR2## where R.sub.2 hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group, and R.sub.3 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group.
    Type: Grant
    Filed: April 20, 1993
    Date of Patent: March 8, 1994
    Assignee: Board of Trustees of Leland Stanford Junior University
    Inventors: Barry M. Trost, Jacques Dumas
  • Patent number: 5245064
    Abstract: The present invention provides a compound of the formula: ##STR1## wherein R.sup.1 is (C.sub.1 -C.sub.5)perfluoroalkyl, R.sup.2 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.3 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.4 is (C.sub.1 -C.sub.5)alkyl and R.sup.5 is (C.sub.1 -C.sub.5)alkyl, with the proviso that no more than two of R.sup.1, R.sup.2 and R.sup.3 can be (C.sub.1 -C.sub.5)perfluoroalkyl; and transition metal complexes thereof.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: September 14, 1993
    Inventors: Paul G. Gassman, John R. Sowa, John W. Mickelson
  • Patent number: 5012023
    Abstract: Hydrocarbyl substituted cyclopentadienes, cyclopentenes, and cyclopentanes are synthetic lubricating compositions. The preferred structures contain 1 to 6 alkyl groups which have 4 to 36 carbon atoms and may have different and varying carbon chain structures. The cyclopentenes and cyclopentanes are prepared by hydrogenation from the corresponding cyclopentadiene intermediates. The cyclopentadienes are prepared by reaction with hydrocarylating agents or alcohols. Mixtures are also disclosed.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: April 30, 1991
    Assignee: Pennzoil Products Company
    Inventors: Clifford G. Venier, Edward W. Casserly
  • Patent number: 5012022
    Abstract: Hydrocarbyl substituted cyclopentadienes, cyclopentenes, and cyclopentanes and synthetic lubricating compositions. The preferred structures contain 1 to 6 alkyl groups which have 4 to 36 carbon atoms and may have different and varying carbon chain structures. The cyclopentenes and cyclopentanes are prepared by hydrogenation from the corresponding cyclopentadiene intermediates. The cyclopentadienes are prepared by reaction with hydrocarbylating agents or alcohols. Mixtures are also disclosed.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: April 30, 1991
    Assignee: Pennzoil Products Company
    Inventors: Clifford G. Venier, Edward W. Casserly
  • Patent number: 4849566
    Abstract: Hydrocarbyl substituted cyclopentadienes, cyclopentenes, and cyclopentanes are synthetic lubricating compositions. The preferred structures contain 1 to 6 alkyl groups which have 4 to 36 carbon atoms and may have different and varying carbon chain structures. The cyclopentenes and cyclopentanes are prepared by hydrogenation from the corresponding cyclopentadiene intermediates. The cyclopentadienes are prepared by reaction with hydrocarbylating agents or alcohols. Mixtures are also disclosed.
    Type: Grant
    Filed: October 22, 1987
    Date of Patent: July 18, 1989
    Assignee: Pennzoil Products Company
    Inventors: Clifford G. Venier, Edward W. Casserly
  • Patent number: 4795843
    Abstract: Organic hydrocarbons which comprise useful compounds may be obtained in a two-step process utilizing methane as a feedstock. The desired compounds are prepared by treating said methane with a halogenating agent such as chlorine, followed by contacting the methyl halide with a conversion catalyst comprising a silicalite. The silicalite which is employed is a silica polymorph consisting of crystalline silica which, after calcination in air at a temperature of 600.degree. C. for 1 hour, has a mean refractory index of 1.39.+-.0.01 and a specific gravity at 25.degree. C. of 1.70.+-.0.05 g/cc.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: January 3, 1989
    Assignee: UOP Inc.
    Inventors: Tamotsu Imai, Paul T. Barger, Anthony H. Eck
  • Patent number: 4721823
    Abstract: Hydrocarbyl substituted cyclopentadienes, cyclopentenes, and cyclopentanes are sythetic lubricating compositions. The preferred structures contain 1 to 6 alkyl groups which have 4 to 36 carbon atoms and may have different and varying carbon chain structures. The cyclopentenes and cyclopentanes are prepared by hydrogenation from the corresponding cyclopentadiene intermediates. The cyclopentadienes are prepared by reaction with hydrocarbylating agents or alcohols. Mixtures are also disclosed.
    Type: Grant
    Filed: September 19, 1986
    Date of Patent: January 26, 1988
    Assignee: Pennzoil Products Company
    Inventors: Clifford G. Venier, Edward W. Casserly
  • Patent number: 4675462
    Abstract: A process for the preparation of (2,2)-paracyclophane by conversion of p.methylbenzyltrimethylammonium halide to the corresponding hydroxide and by Hofmann elimination from p.methylbenzyltrimethylammonium hydroxide, wherein both reactions are carried out in the same aqueous solution of an alkaline hydroxide and in the presence of a copper or iron compound.
    Type: Grant
    Filed: October 29, 1986
    Date of Patent: June 23, 1987
    Assignee: Montedison S.p.A.
    Inventors: Raffaele Ungarelli, Maurizio A. Beretta, Loris Sogli
  • Patent number: 4431853
    Abstract: A 1,2-di[trans(equatorial-equatorial)cyclohexyl]-ethane derivative of the following general formula ##STR1## wherein R and R', independently from each other, represent a linear alkyl group having 1 to 10 carbon atoms.
    Type: Grant
    Filed: January 6, 1982
    Date of Patent: February 14, 1984
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hisato Sato, Haruyoshi Takatsu, Kiyofumi Takeuchi, Yutaka Fujita, Masayuki Tazume, Hiroyuki Ohnishi