Triple-bond Product Patents (Class 585/534)
  • Patent number: 9034100
    Abstract: The invention relates to CO2 capturing binder with an amortized environmental cost, the method of manufacture thereof by means of selecting, purifying and optimizing the carbide lime paste for use as a cementing material, and aggregates for the manufacture of lime paints and slurries, stuccos, mortars and concretes having multiple applications in the construction industry, in architectural restoration, in public works and land conditioning, object of the present invention. It is basically characterized in that the raw material is the residue in the form of sludge generated in the industrial manufacture of acetylene (C2H2) from calcium carbide (CaC2) the fundamental component of which is calcium hydroxide (Ca(OH)2) in highly reactive nanometric formations treated in a specific manner according to the invention.
    Type: Grant
    Filed: May 4, 2010
    Date of Patent: May 19, 2015
    Assignee: GEOSILEX TRENZA METAL, S.L.
    Inventors: Miguel Angel Bermejo Sotillo, Carlos Rodriguez Navarro, Encarnación Ruiz Agudo, Kerstin Elert
  • Publication number: 20140275682
    Abstract: A method for generating acetylene from calcium carbide and recovering acetylene that would normally be lost during the process. The method includes putting calcium carbide into the purge bin of an acetylene generator; purging the purge bin with purge gas; transferring the calcium carbide to a hot aqueous bath in an acetylene generation chamber to generate acetylene; allowing a portion of the acetylene to move back into the purge bin where it mixes with the purge gas; passing the acetylene and purge gases through cold absorption water and allowing the absorption water to absorb some of the acetylene gas; transferring the absorption water back to the aqueous bath and allowing at least some of the acetylene to be released from the water as the temperature increases; recovering released acetylene; and using the aqueous bath to hydrolyze a subsequent batch of calcium carbide.
    Type: Application
    Filed: March 14, 2014
    Publication date: September 18, 2014
    Inventors: Stewart W. Robinson, Gregory M. Brasel, Craig Franklyn Dauphinee, David Wilson Carter
  • Patent number: 8748686
    Abstract: A process and apparatus are provided to produce acetylene from a feed stream of low hydrogen content hydrocarbons such as coal by: (a) blending the hydrocarbons with methane to provide a blended mixture containing at least about 12.5 wt % atomic hydrogen; (b) partially combusting the blended mixture in a reactor in the presence of a source of oxygen to provide a partially combusted mixture at or above a temperature sufficient to produce methyl radicals; (c) maintaining the partially combusted mixture at or above the temperature for a residence time sufficient to produce a product stream containing enhanced yields of acetylene without significant formation of coke or coke precursors; (d) cooling the product stream to reduce the temperature of the product stream within a time sufficiently brief to substantially arrest any cracking reactions and provide a cooled product stream; and (e) recovering acetylene from the cooled product stream.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: June 10, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Paul F. Keusenkothen, Frank Hershkowitz
  • Patent number: 8742194
    Abstract: A hydrocarbon-containing mixture including acetylene and butenyne is disclosed. The hydrocarbon-containing mixture can include 10% to 89% acetylene, 10% to 89% butenyne, and at least 0.25% dimethyl butadiyne. A method and system for producing the hydrocarbon-containing mixture is also disclosed. The system can include an acetylene production subsystem comprising at least one vessel and an acetylene output for delivering acetylene to a finishing vessel via a finishing vessel inlet. The finishing vessel can include a diffuser in fluid communication with the finishing vessel inlet, and gas exiting the diffuser can pass through a reaction chamber filled with solid calcium carbide before passing through a finishing vessel outlet.
    Type: Grant
    Filed: May 21, 2012
    Date of Patent: June 3, 2014
    Assignee: CM Global Systems, LLC
    Inventors: Douglas O. Mapp, Sr., Douglas O. Mapp, II
  • Patent number: 8728425
    Abstract: A method for performing an energy efficient desulphurization and decarbonization of a flue gas comprising sulphur oxides and carbon dioxide includes (a) starting a reaction between an electropositive metal and the sulphur oxides and the carbon dioxide of said flue gas; (b) reducing the sulphur oxides and the carbon dioxide of said flue gas simultaneously in an exothermic reaction with an electropositive metal and thereby generating reduced gaseous carbon products and solid reaction products while cooling; (c) extracting the solid reaction products of the reducing step (a) in a solvent to generate a first suspension comprising suspended carbon containing reaction products and sulphur containing reaction products; (d) oxidizing the first suspension obtained in step (b) to generate a second suspension comprising suspended carbon containing reaction products and oxidized sulphur containing reaction products; and (e) separating the oxidized sulphur containing reaction products from the suspended carbon containing
    Type: Grant
    Filed: April 17, 2012
    Date of Patent: May 20, 2014
    Assignee: Siemens Aktiengesellschaft
    Inventors: Günter Schmid, Dan Taroata, Manfred Baldauf, Elena Arvanitis, Frank Walachowicz
  • Publication number: 20130144102
    Abstract: Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.
    Type: Application
    Filed: March 31, 2011
    Publication date: June 6, 2013
    Applicant: STUDIENGESELLSCHAFT KOHLE MBH
    Inventors: Alois Fuerstner, Johannes Heppekausen, Volker Hickmann, Robert Stade
  • Patent number: 8445739
    Abstract: A process for converting natural gas from which contaminants have been sufficiently removed to acetylene includes heating the purified gas through a selected range of temperature for adequate time or combustion of the purified gas at adequate temperature within a suitable environment during an adequate reaction time to convert a fraction of the gas stream to acetylene, wherein the acetylene is directed for other processes, reactions, and uses. A process for converting natural gas to liquid hydrocarbons by combusting externally derived hydrogen for heating natural gas to a selected range of temperature. A process for converting natural gas to liquid hydrocarbons by reacting conversion products with externally derived hydrogen to form olefins comprising ethylene, and catalytically forming liquid hydrocarbons from the olefins comprising ethylene.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: May 21, 2013
    Assignee: Synfuels International, Inc.
    Inventor: Edward R. Peterson
  • Patent number: 8080697
    Abstract: The present invention relates to a process for the production of ethylene, comprising the following steps of: (a) thermally converting a feed charge containing methane into acetylene as an intermediate, (b) in-situ hydrogenation of the acetylene produced in step (a) into ethylene by a non-catalytic hydrogen transfer mechanism, characterized by (c) recovering heat from hot effluents obtained in step (b) which may be utilized for different purposes.
    Type: Grant
    Filed: January 18, 2007
    Date of Patent: December 20, 2011
    Assignee: Saudi Basic Industries Corporation
    Inventors: Yungyi Lin, Mohamed Abdelghani
  • Patent number: 7956228
    Abstract: A process for the preparation of acetylene and synthesis gas by partial thermal oxidation in a reactor which has a burner having passages, wherein the starting materials to be reacted are rapidly and completely mixed only immediately before the flame reaction zone in the passages of the burner, a mean flow rate which exceeds the flame propagation velocities under the given reaction conditions being established in the mixing zone within the passages.
    Type: Grant
    Filed: April 21, 2006
    Date of Patent: June 7, 2011
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bartenbach, Kai Rainer Ehrhardt, Arne Hoffmann, Frank Kleine Jaeger
  • Patent number: 7928275
    Abstract: Process for the preparation of acetylene from hydrocarbons by partial oxidation, arc cleavage or pyrolysis, the material stream comprising the acetylene and soot obtained being fed to a compressor, wherein a liquid which takes up the major part of the soot present in the material stream is sprayed into the compressor.
    Type: Grant
    Filed: February 13, 2007
    Date of Patent: April 19, 2011
    Assignee: BASF SE
    Inventors: Michael Bachtler, Kai Rainer Ehrhardt, Christopher P Witte, Michael L. Hayes
  • Publication number: 20080188698
    Abstract: A process for the preparation of acetylene and synthesis gas by partial thermal oxidation in a reactor which has a burner having passages, wherein the starting materials to be reacted are rapidly and completely mixed only immediately before the flame reaction zone in the passages of the burner, a mean flow rate which exceeds the flame propagation velocities under the given reaction conditions being established in the mixing zone within the passages.
    Type: Application
    Filed: April 21, 2006
    Publication date: August 7, 2008
    Applicant: BASF Aktiengesellschaft
    Inventors: Bernd Bartenbach, Kai Rainer Ehrhardt, Arne Hoffmann, Frank Kleine Jager
  • Publication number: 20080045766
    Abstract: Process for producing a supported catalyst which comprises at least 75% by weight of Al2O3, whose proportion of Al2O3 in the delta or theta modification is, based on the proportion of Al2O3, at least 1% and which comprises a rhenium compound and, if appropriate, a promoter as active component (A), which comprises a) converting a customary support (S) which comprises at least 75% by weight of Al2O3 and to which a promoter may, if appropriate, have been applied is converted into a modified support (S) whose proportion of Al2O3 in the delta or theta modification is, based on the proportion of Al2O3, at least 1% by calcining the customary support (S) at a temperature of from 750 to 1100°C., b) producing a supported catalyst precursor from the modified support (S) by applying the active component (A) comprising the rhenium compound to the modified support (S) and c) calcining the supported catalyst precursor at a temperature of from 500 to 750° C.
    Type: Application
    Filed: February 24, 2005
    Publication date: February 21, 2008
    Inventors: Markus Schubert, Jurgen Stephan, Volker Bohn, Andreas Brodhagen, Frank Poplow
  • Patent number: 7217851
    Abstract: Provided is a method for the synthesis of 1,4-dicyclopropyl-1,3-butadiyne from CPA. Such butadiyne is prepared by oxidative coupling of cyclopropyl acetylene (CPA) using catalytic amounts each of copper (I)chloride and tetrametylethylenediamine (TMEDA) in isopropanol under aerobic conditions. The resulting butadiyne can serve as a fuel or a fuel additive for combustion in engines propelling motor vehicles, marine vessels, aircraft, rockets and other vehicles.
    Type: Grant
    Filed: March 31, 2004
    Date of Patent: May 15, 2007
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Suresh C. Suri, Michael G. Tinnirello
  • Patent number: 7119240
    Abstract: A process for converting natural gas to an olefin includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily ethylene or acetylene, and reacting with hydrogen in the presence of a catalyst to produce the olefin, usually ethylene. A portion of the incoming natural gas may be used to heat the remainder of the natural gas to the selected range of temperature. Hydrogen resulting from the reactions may be used to make electricity in a fuel cell. Alternatively, hydrogen may be burned to heat the natural gas to the selected range of temperature.
    Type: Grant
    Filed: July 1, 2003
    Date of Patent: October 10, 2006
    Assignee: The Texas A&M University System
    Inventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
  • Patent number: 6967256
    Abstract: One aspect of the present invention relates to methods of preparing enedialkylidyne complexes, enediynes, and alkyne metathesis catalysts, as well as methods of catalyzing alkyne metathesis reactions. The present invention also relates to methods of activating enedialkylidyne complexes for metathesis. The present invention also relates to enedialkylidyne complexes.
    Type: Grant
    Filed: September 19, 2003
    Date of Patent: November 22, 2005
    Assignee: Massachusetts Institute of Technology
    Inventors: Christopher C. Cummins, James M. Blackwell
  • Patent number: 6849664
    Abstract: The present invention relates to the use of deactivatable biocides in cooling water systems of industrial processes that require dissipation of heat. The present invention relates to methods of inhibiting growth and reproduction of microorganisms in the cooling water comprising adding the deactivatable biocides to the cooling water and irreversibly deactivating the deactivatable biocides before or upon disposal of the cooling water.
    Type: Grant
    Filed: October 18, 2001
    Date of Patent: February 1, 2005
    Assignee: Chevron U.S.A. Inc.
    Inventors: Kirk T. O'Reilly, Michael E. Moir, Dennis J. O'Rear, Richard O. Moore, Jr.
  • Publication number: 20040102647
    Abstract: A process to produce ethyne comprising passing acetaldehyde in the gas phase through a reaction zone containing a dehydrating metal oxide catalyst such as aluminum oxide or magnesium oxide at a temperature of approximately 375 C. to produce ethyne and water and a cooling zone following the reaction zone.
    Type: Application
    Filed: September 30, 2003
    Publication date: May 27, 2004
    Inventor: Christian Everett
  • Patent number: 6632484
    Abstract: Described are dialkyne compounds of the formula I in which n, m, R1, R2, X1, X2, X3, X4, Z1, Z2, A1, A2, Q, Y1 and Y2 are as defined herein and the use of such compounds in liquid-crystal media.
    Type: Grant
    Filed: July 19, 2001
    Date of Patent: October 14, 2003
    Assignee: Merck Patent Gesellschaft mit beschränkter Haftung
    Inventors: Volker Reiffenrath, Georg Lüssem
  • Patent number: 6602920
    Abstract: A process for converting natural gas to a liquid includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily ethylene or acetylene, and reacting methane and the reactive hydrocarbons in the presence of an acidic catalyst to produce a liquid, predominantly naphtha or gasoline. A portion of the incoming natural gas may be used to heat the remainder of the natural gas to the selected range of temperature. Hydrogen resulting from the reactions may be used to make electricity in a fuel cell. Alternatively, hydrogen may be burned to heat the natural gas to the selected range of temperature.
    Type: Grant
    Filed: March 9, 2001
    Date of Patent: August 5, 2003
    Assignee: The Texas A&M University System
    Inventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
  • Patent number: 6570046
    Abstract: The use of a settling aid in the reactor during acetylene production results in the by-product lime slurry being easier to handle and allows the acetylene producers to use different sources of calcium carbide as well as the calcium carbide manufacturers to use different sources of raw materials to make calcium carbide.
    Type: Grant
    Filed: August 16, 2001
    Date of Patent: May 27, 2003
    Assignee: Elkem Limited
    Inventors: G. Wayne Linn, Nancy H. Davis, Michael D. Simons, Mark F. Nilsen
  • Publication number: 20030040654
    Abstract: The use of a settling aid in the reactor during acetylene production results in the by-product lime slurry being easier to handle and allows the acetylene producers to use different sources of calcium carbide as well as the calcium carbide manufacturers to use different sources of raw materials to make calcium carbide.
    Type: Application
    Filed: August 16, 2001
    Publication date: February 27, 2003
    Inventors: G. Wayne Linn, Nancy H. Davis, Michael D. Simons, Mark F. Nilsen
  • Patent number: 6392112
    Abstract: Polyacetylene compounds and process for the preparation thereof from a chiral dihydroxy amide are described. The compounds preferably have diacyl groups attached to the amide. The compounds are useful for making films which are electrically conductive, near infrared absorbing, polarizing, and have the optical characteristic and other properties of polyacetylenes.
    Type: Grant
    Filed: August 23, 2000
    Date of Patent: May 21, 2002
    Assignee: Board of Trustees of Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6392110
    Abstract: Polyacetylene compounds and process for the preparation thereof from a chiral dihydroxy amide are described. The compounds preferably have diacyl groups attached to the amide. The compounds are useful for making films which are electrically conductive, near infrared absorbing, polarizing, and have the optical characteristic and other properties of polyacetylenes.
    Type: Grant
    Filed: August 23, 2000
    Date of Patent: May 21, 2002
    Assignee: Board of Trustees of Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6365792
    Abstract: The invention relates to a process for the preparation of acetylene and synthesis gas by thermal treatment of a starting mixture containing one or more hydrocarbons and in addition molecular oxygen and/or one or more compounds containing the element oxygen, in which the starting mixture is heated, brought to reaction in a reactor and subsequently cooled. The process has the special feature that the starting mixture is heated to a maximum of 1400° C. It is then possible to carry out the process with comparatively little expenditure of energy.
    Type: Grant
    Filed: March 20, 2000
    Date of Patent: April 2, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Stapf, Peter Pässler, Michael Bachtler, Olaf Scheidsteger, Bernd Bartenbach
  • 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: 20020000085
    Abstract: A process for converting natural gas to a liquid includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily ethylene or acetylene, and reacting methane and the reactive hydrocarbons in the presence of an acidic catalyst to produce a liquid, predominantly naphtha or gasoline. A portion of the incoming natural gas may be used to heat the remainder of the natural gas to the selected range of temperature. Hydrogen resulting from the reactions may be used to make electricity in a fuel cell. Alternatively, hydrogen may be burned to heat the natural gas to the selected range of temperature.
    Type: Application
    Filed: March 9, 2001
    Publication date: January 3, 2002
    Inventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
  • Patent number: 6333443
    Abstract: A process for producing methylacetylene and propadiene in a reaction zone which is elongate in one direction (one axis) comprises a heating zone and a cooling zone following said heating zone, in which a gas mixture comprising at least one hydrocarbon containing at least three carbon atoms e.g. propane and/or propylene from stream cracking, and at least one diluent is circulated in the heating zone, under super-atmospheric pressure, in a flow direction substantially parallel to the direction (to the axis) of the heating zone, wherein the heating zone comprises at least one preheating zone in which the temperature of said gas mixture increases by about 50° C. to 120° C. per {fraction (1/10)} of the length of the heating zone, at least one pyrolysis zone for the feed in which the temperature rises by about 20° C. to 50° C. per {fraction (1/10)} of the length of the heating zone and at least one methylacetylene-propadiene formation zone in which the temperature climbs by about 70° C.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: December 25, 2001
    Assignee: Institut Francais du Petrole
    Inventor: Christian Busson
  • Patent number: 6313364
    Abstract: The present invention relates to a process for the preparation of cyclopropaneacetylene by the two step process: (1) an alkylation of propiolic acid with a 1,3-disubstituted propane followed by a cycloalkylation to give a 3-cyclopropaneacetylene carboxylic acid; and (2) decarboxylation of 3-cyclopropaneacetylene carboxylic acid in the presence of copper catalyst.
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: November 6, 2001
    Assignee: Merck & Co., Inc.
    Inventor: Karel M. J. Brands
  • 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: 6235957
    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.
    Type: Grant
    Filed: June 28, 1999
    Date of Patent: May 22, 2001
    Assignee: DuPont Pharmaceuticals Company
    Inventor: Anusuya Choudhury
  • 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: 6203724
    Abstract: The invention relates to cyclohexane derivatives of the formula I in which R, R1, R2, R3, A, A1, A2, A3, Z, Z1, Z2, Z3, B, B1, X, p, m, n, r and s are as defined above.
    Type: Grant
    Filed: December 3, 1999
    Date of Patent: March 20, 2001
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Michael Heckmeier, Matthias Bremer
  • Patent number: 6180835
    Abstract: A cyclopropylacetylene derivative of the formula (V): is prepared by reacting a propynol derivative of the formula (I): with a propane derivative of the formula (VI): in the presence of a base in an amount of 2 or more equivalents relative to the propynol derivative to give a cyclopropane derivative of the formula (III): deprotecting the protecting group for the hydroxyl group of the cyclopropane derivative to give a cyclopropylpropynol derivative of the formula (IV): and subjecting the cyclopropylpropynol derivative to retro-ethynylation. In the above formulas R1, R2, R3, R4 and R5 represent hydrogen; or an alkyl, alkenyl, aryl or aralkyl group, each of which may have a substituent, R6 and R7 is hydrogen; or an alkyl, alkenyl, aryl or aralkyl group, each of which may have a substituent, or R6 and R7 taken together form a ring, R8 is a protecting group for the hydroxyl group and X and Y are each a leaving group.
    Type: Grant
    Filed: February 5, 1999
    Date of Patent: January 30, 2001
    Assignee: Kuraray Co., Ltd.
    Inventors: Goro Asanuma, Kazuya Takaki, Shigeo Ohzono, Manzo Shiono
  • Patent number: 6130260
    Abstract: A process for converting natural gas to a liquid includes heating the gas to a selected range of temperature to convert a fraction of the gas stream to reactive hydrocarbons, primarily acetylene, and reacting methane and the reactive hydrocarbons in the presence of an acidic catalyst to produce a liquid, predominantly pentane. Hydrogen resulting from the reactions is used to heat the incoming natural gas, either with a hydrogen furnace or by electrical energy generated from the hydrogen. Little or no use of methane is required to supply energy for the process.
    Type: Grant
    Filed: November 25, 1998
    Date of Patent: October 10, 2000
    Assignee: The Texas A&M University Systems
    Inventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
  • Patent number: 6127583
    Abstract: A preparation process of an acetylene derivative comprising reacting a compound having a skeleton represented by the formula (1): ##STR1## in the molecular formula with a compound represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 R.sup.3 and R.sup.4 are individually an alkyl group having 1 to 6 carbon atoms and can be the same or different, R.sup.1 and R.sup.3 can bond each other to form a ring, and R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 can be bond each other to form one or two heterocyclic rings: or with a compound represented by the formula (3): wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as in the formula (2), and X.sub.1 is a ##STR3## chlorine, bromine or iodine atom.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: October 3, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroshi Sonoda, Kazunari Okada, Kenichi Goto, Kouki Fukumura, Junko Naruse, Hidetoshi Hayashi, Teruyuki Nagata, Akira Takahashi
  • 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: 6042799
    Abstract: In the process for preparing acetylene and hydrocyanic acid by pyrolyzing acrylonitrile in a reactor, the gaseous reaction products of the pyrolysis are quenched down to less than 100.degree. C. immediately, advantageously within seconds, preferably within .ltoreq.1 s, of leaving the pyrolysis zone.
    Type: Grant
    Filed: March 4, 1998
    Date of Patent: March 28, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Halbritter, Michael Henningsen, Manfred Julius, Wolf Stegmaier
  • 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: 6002062
    Abstract: Ethynylcyclopropane is prepared from (1,1-dimethoxyethyl)cyclopropane by a two-stage elimination of methanol. Ethynylcyclopropane is an intermediate in the synthesis of pharmaceutically active ingredients, for example, antiviral agents.
    Type: Grant
    Filed: December 4, 1998
    Date of Patent: December 14, 1999
    Assignee: Lonza AG
    Inventors: Dominique Michel, Paul Hanselmann
  • Patent number: 5990368
    Abstract: Providing an isomerization process which can isomerize allenes to alkynes less expensively and stably is an assignment to be solved by the present invention and given thereto. The present invention is an isomerization process including the step of reacting an allene-lype hydrocarbon compound (R.sub.1 R.sub.2 C.dbd.C.dbd.CR.sub.3 R.sub.4) in the presence of alkaline-earth metal hydride working as an isomerization catalyst, thereby isomerizing the allene-type hydrocarbon compound to an alkyne-type hydrocarbon compound (R.sub.1 C.ident.C--CR.sub.2 R.sub.3 R.sub.4).
    Type: Grant
    Filed: July 7, 1998
    Date of Patent: November 23, 1999
    Assignee: Kabushiki Kaisha Toyota Chuo Kenkyusho
    Inventors: Mitsuru Nakano, Bruce M. Novak
  • 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: 5948945
    Abstract: A process for vinylation of an organic acidic-hydrogen compound, which entails reacting an organic acidic-hydrogen compound with acetylene or an acetylene-containing gas under elevated pressure and at elevated temperature in the presence of a base, wherein reactor regions initiating decomposition of acetylene are treated with an effective amount of a chemically inert oil of medium viscosity.
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: September 7, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Erich Lorenz, Herbert Helfert, Martin Schmidt-Radde, Hans-Peter Schildberg, Gunter Saladin
  • Patent number: 5942652
    Abstract: The invention relates to the process for preparing ethyne by the pyrolysis of ethane by heating the same for a period of time that is less than 0.5 sec in a pyrolysis reactor at a temperature in the range of 950 to 1500.degree. C., using steam as diluent gas in a steam/ethane molar ratio of at most 3.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: August 24, 1999
    Assignee: Institut Fran.cedilla.ais du Petrole
    Inventors: Emile Maria Joseph Duijsens, Pieter Oldenhove
  • Patent number: 5879585
    Abstract: A liquid crystalline compound having a remarkably high .DELTA.n and good miscibility with other liquid crystalline compounds, and expressed by the general formula (1) ##STR1## wherein R.sub.1 represents, for example, a halogen atom, cyano group, or an alkyl or alkenyl group of 1 to 15 carbon atoms in which alkyl or alkenyl group hydrogen atom may be replaced, for example, by fluorine atom, and one or not-adjacent two or more methylene groups may be replaced by oxygen atom, --CH.dbd.CH-- or --C.tbd.C--; R.sub.2 represents an alkyl group of 1 to 10 carbon atoms or hydrogen atom; rings A.sub.1, A.sub.2, A.sub.3, and A.sub.4 independently represent, for example, 1,4-cyclohexylene or 1,4-phenylene in which hydrogen atom may be replaced by a halogen atom or cyano group; Z.sub.1, Z.sub.2, and Z.sub.3 independently represent, for example, a covalent bond or --CH.sub.2 CH.sub.2 --; s and t are 0 or 1; u is an integer of 1 to 5; and each of the elements in the general formula may be its isotope.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: March 9, 1999
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
  • Patent number: 5789644
    Abstract: In the preparation of acetylene and synthesis gas by partial oxidation of hydrocarbons with oxygen, the feedstock gases are first separately preheated, then intensively mixed in a mixing zone, reacted after flowing through a burner block and then rapidly cooled.The burner block has a number of continuous ducts. According to the invention the ducts of the burner block are covered on the inlet side by plates furnished with perforations.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 4, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Passler, Rainer Feser, Hans-Gunter Thelen
  • Patent number: 5744666
    Abstract: A process for preparing an alkynyl fulvene group containing compound and said compound is provided. Said process comprises reacting an alkynyl ketone compound with a cyclopentadienyl-type compound.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: April 28, 1998
    Assignee: Phillips Petroleum Company
    Inventors: M. Bruce Welch, Bernd Peifer, Helmut G. Alt
  • Patent number: 5728908
    Abstract: A process for preparing a bridged ligand, where said bridged ligand has an alkynyl group, and said bridged ligand is provided. Said process comprises reacting an alkynyl fulvene containing compound with an alkali metal salt of a cyclopentadienyl-type compound.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: March 17, 1998
    Assignee: Phillips Petroleum Company
    Inventors: M. Bruce Welch, Bernd Peifer, Helmut G. Alt
  • Patent number: RE37947
    Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: December 31, 2002
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Phillippe Nedoncelle