Triple-bond Product Patents (Class 585/534)
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Patent number: 9034100Abstract: 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: GrantFiled: May 4, 2010Date of Patent: May 19, 2015Assignee: GEOSILEX TRENZA METAL, S.L.Inventors: Miguel Angel Bermejo Sotillo, Carlos Rodriguez Navarro, Encarnación Ruiz Agudo, Kerstin Elert
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Publication number: 20140275682Abstract: 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: ApplicationFiled: March 14, 2014Publication date: September 18, 2014Inventors: Stewart W. Robinson, Gregory M. Brasel, Craig Franklyn Dauphinee, David Wilson Carter
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Patent number: 8748686Abstract: 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: GrantFiled: November 25, 2008Date of Patent: June 10, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Paul F. Keusenkothen, Frank Hershkowitz
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Patent number: 8742194Abstract: 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: GrantFiled: May 21, 2012Date of Patent: June 3, 2014Assignee: CM Global Systems, LLCInventors: Douglas O. Mapp, Sr., Douglas O. Mapp, II
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Patent number: 8728425Abstract: 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 containingType: GrantFiled: April 17, 2012Date of Patent: May 20, 2014Assignee: Siemens AktiengesellschaftInventors: Günter Schmid, Dan Taroata, Manfred Baldauf, Elena Arvanitis, Frank Walachowicz
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Publication number: 20130144102Abstract: Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.Type: ApplicationFiled: March 31, 2011Publication date: June 6, 2013Applicant: STUDIENGESELLSCHAFT KOHLE MBHInventors: Alois Fuerstner, Johannes Heppekausen, Volker Hickmann, Robert Stade
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Patent number: 8445739Abstract: 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: GrantFiled: August 27, 2009Date of Patent: May 21, 2013Assignee: Synfuels International, Inc.Inventor: Edward R. Peterson
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Patent number: 8080697Abstract: 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: GrantFiled: January 18, 2007Date of Patent: December 20, 2011Assignee: Saudi Basic Industries CorporationInventors: Yungyi Lin, Mohamed Abdelghani
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Patent number: 7956228Abstract: 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: GrantFiled: April 21, 2006Date of Patent: June 7, 2011Assignee: BASF AktiengesellschaftInventors: Bernd Bartenbach, Kai Rainer Ehrhardt, Arne Hoffmann, Frank Kleine Jaeger
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Patent number: 7928275Abstract: 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: GrantFiled: February 13, 2007Date of Patent: April 19, 2011Assignee: BASF SEInventors: Michael Bachtler, Kai Rainer Ehrhardt, Christopher P Witte, Michael L. Hayes
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Publication number: 20080188698Abstract: 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: ApplicationFiled: April 21, 2006Publication date: August 7, 2008Applicant: BASF AktiengesellschaftInventors: Bernd Bartenbach, Kai Rainer Ehrhardt, Arne Hoffmann, Frank Kleine Jager
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Publication number: 20080045766Abstract: 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: ApplicationFiled: February 24, 2005Publication date: February 21, 2008Inventors: Markus Schubert, Jurgen Stephan, Volker Bohn, Andreas Brodhagen, Frank Poplow
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Patent number: 7217851Abstract: 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: GrantFiled: March 31, 2004Date of Patent: May 15, 2007Assignee: United States of America as represented by the Secretary of the Air ForceInventors: Suresh C. Suri, Michael G. Tinnirello
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Patent number: 7119240Abstract: 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: GrantFiled: July 1, 2003Date of Patent: October 10, 2006Assignee: The Texas A&M University SystemInventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
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Patent number: 6967256Abstract: 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: GrantFiled: September 19, 2003Date of Patent: November 22, 2005Assignee: Massachusetts Institute of TechnologyInventors: Christopher C. Cummins, James M. Blackwell
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Patent number: 6849664Abstract: 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: GrantFiled: October 18, 2001Date of Patent: February 1, 2005Assignee: Chevron U.S.A. Inc.Inventors: Kirk T. O'Reilly, Michael E. Moir, Dennis J. O'Rear, Richard O. Moore, Jr.
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Publication number: 20040102647Abstract: 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: ApplicationFiled: September 30, 2003Publication date: May 27, 2004Inventor: Christian Everett
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Patent number: 6632484Abstract: 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: GrantFiled: July 19, 2001Date of Patent: October 14, 2003Assignee: Merck Patent Gesellschaft mit beschränkter HaftungInventors: Volker Reiffenrath, Georg Lüssem
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Patent number: 6602920Abstract: 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: GrantFiled: March 9, 2001Date of Patent: August 5, 2003Assignee: The Texas A&M University SystemInventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
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Patent number: 6570046Abstract: 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: GrantFiled: August 16, 2001Date of Patent: May 27, 2003Assignee: Elkem LimitedInventors: G. Wayne Linn, Nancy H. Davis, Michael D. Simons, Mark F. Nilsen
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Publication number: 20030040654Abstract: 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: ApplicationFiled: August 16, 2001Publication date: February 27, 2003Inventors: G. Wayne Linn, Nancy H. Davis, Michael D. Simons, Mark F. Nilsen
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Patent number: 6392110Abstract: 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: GrantFiled: August 23, 2000Date of Patent: May 21, 2002Assignee: Board of Trustees of Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang
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Patent number: 6392112Abstract: 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: GrantFiled: August 23, 2000Date of Patent: May 21, 2002Assignee: Board of Trustees of Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang
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Patent number: 6365792Abstract: 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: GrantFiled: March 20, 2000Date of Patent: April 2, 2002Assignee: BASF AktiengesellschaftInventors: Dieter Stapf, Peter Pässler, Michael Bachtler, Olaf Scheidsteger, Bernd Bartenbach
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Patent number: 6359164Abstract: 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: GrantFiled: September 30, 1999Date of Patent: March 19, 2002Inventors: Zhe Wang, Joseph M. Fortunak
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Publication number: 20020000085Abstract: 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: ApplicationFiled: March 9, 2001Publication date: January 3, 2002Inventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
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Patent number: 6333443Abstract: 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: GrantFiled: March 31, 2000Date of Patent: December 25, 2001Assignee: Institut Francais du PetroleInventor: Christian Busson
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Patent number: 6313364Abstract: 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: GrantFiled: October 27, 2000Date of Patent: November 6, 2001Assignee: Merck & Co., Inc.Inventor: Karel M. J. Brands
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Patent number: 6297410Abstract: 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: GrantFiled: January 12, 2000Date of Patent: October 2, 2001Assignee: DuPont Pharmaceuticals CompanyInventors: Joseph M. Fortunak, Zhe Wang, Jianguo Yin
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Patent number: 6235957Abstract: 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: GrantFiled: June 28, 1999Date of Patent: May 22, 2001Assignee: DuPont Pharmaceuticals CompanyInventor: Anusuya Choudhury
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Patent number: 6207864Abstract: 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: GrantFiled: September 1, 1999Date of Patent: March 27, 2001Assignee: BASF AktiengesellschaftInventors: Michael Henningsen, Armin Stamm, Martin Fischer, Wolfgang Siegel
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Patent number: 6203724Abstract: 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: GrantFiled: December 3, 1999Date of Patent: March 20, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Michael Heckmeier, Matthias Bremer
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Patent number: 6180835Abstract: 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: GrantFiled: February 5, 1999Date of Patent: January 30, 2001Assignee: Kuraray Co., Ltd.Inventors: Goro Asanuma, Kazuya Takaki, Shigeo Ohzono, Manzo Shiono
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Patent number: 6130260Abstract: 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: GrantFiled: November 25, 1998Date of Patent: October 10, 2000Assignee: The Texas A&M University SystemsInventors: Kenneth R. Hall, Jerry A. Bullin, Philip T. Eubank, Aydin Akgerman, Rayford G. Anthony
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Patent number: 6127583Abstract: 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: GrantFiled: March 31, 1999Date of Patent: October 3, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Kenichi Goto, Kouki Fukumura, Junko Naruse, Hidetoshi Hayashi, Teruyuki Nagata, Akira Takahashi
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Patent number: 6072094Abstract: An efficient and facile process for the preparation of cyclopropylacetylene from thioanisole and cyclopropyl substituted ketones or aldehydes is disclosed.Type: GrantFiled: July 28, 1998Date of Patent: June 6, 2000Assignee: Merck & Co., Inc.Inventors: Sandor Karady, Benjamin Marcune
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Patent number: 6049019Abstract: 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: GrantFiled: July 30, 1998Date of Patent: April 11, 2000Assignee: DuPont PharmaceuticalsInventors: Joseph M. Fortunak, Zhe Wang, Jianguo Yin
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Patent number: 6042799Abstract: 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: GrantFiled: March 4, 1998Date of Patent: March 28, 2000Assignee: BASF AktiengesellschaftInventors: Klaus Halbritter, Michael Henningsen, Manfred Julius, Wolf Stegmaier
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Patent number: 6028237Abstract: 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: GrantFiled: December 15, 1997Date of Patent: February 22, 2000Assignee: DuPont Pharmaceuticals CompanyInventor: Rodney Lawrence Parsons, Jr.
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Patent number: 6002062Abstract: 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: GrantFiled: December 4, 1998Date of Patent: December 14, 1999Assignee: Lonza AGInventors: Dominique Michel, Paul Hanselmann
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Patent number: 5990368Abstract: 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: GrantFiled: July 7, 1998Date of Patent: November 23, 1999Assignee: Kabushiki Kaisha Toyota Chuo KenkyushoInventors: Mitsuru Nakano, Bruce M. Novak
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Patent number: 5973092Abstract: 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: GrantFiled: April 8, 1997Date of Patent: October 26, 1999Assignee: The University of Southern MississippiInventors: Lon J. Mathias, Gregory J. Tregre
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Patent number: 5952537Abstract: 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: GrantFiled: March 13, 1998Date of Patent: September 14, 1999Assignee: Wiley Organics, Inc.Inventors: Kurt R. Stickley, David B. Wiley
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Patent number: 5948945Abstract: 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: GrantFiled: March 23, 1998Date of Patent: September 7, 1999Assignee: BASF AktiengesellschaftInventors: Rudolf Erich Lorenz, Herbert Helfert, Martin Schmidt-Radde, Hans-Peter Schildberg, Gunter Saladin
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Patent number: 5942652Abstract: 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: GrantFiled: September 23, 1997Date of Patent: August 24, 1999Assignee: Institut Fran.cedilla.ais du PetroleInventors: Emile Maria Joseph Duijsens, Pieter Oldenhove
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Patent number: 5879585Abstract: 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: GrantFiled: October 10, 1997Date of Patent: March 9, 1999Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 5789644Abstract: 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: GrantFiled: June 6, 1995Date of Patent: August 4, 1998Assignee: BASF AktiengesellschaftInventors: Peter Passler, Rainer Feser, Hans-Gunter Thelen
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Patent number: 5744666Abstract: 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: GrantFiled: December 6, 1996Date of Patent: April 28, 1998Assignee: Phillips Petroleum CompanyInventors: M. Bruce Welch, Bernd Peifer, Helmut G. Alt
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Patent number: 5728908Abstract: 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: GrantFiled: December 6, 1996Date of Patent: March 17, 1998Assignee: Phillips Petroleum CompanyInventors: M. Bruce Welch, Bernd Peifer, Helmut G. Alt
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Patent number: RE37947Abstract: 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: GrantFiled: January 5, 2000Date of Patent: December 31, 2002Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Phillippe Nedoncelle