Triple-bond Product Patents (Class 585/505)
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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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Publication number: 20130305597Abstract: 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: ApplicationFiled: May 21, 2012Publication date: November 21, 2013Applicant: CM Global Systems, LLCInventors: DOUGLAS O. MAPP, SR., Douglas O. Mapp, II
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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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Publication number: 20040002612Abstract: A fluorine-containing styrene monomer of the formula (2) is produced by a first, second or third process. The first process includes (a) reacting a compound of the formula (1) with a compound of the formula (3), in the presence of a metal catalyst; (b) reacting the product of the step (a) with a base; and (c) reacting the product of the step (b) with hydrogen, in the presence of a metal catalyst and a phosphine or amine, thereby producing the target styrene monomer. The second process includes reacting a compound of the formula (1) with a compound of the formula (12), in the presence of a metal catalyst, thereby producing the target styrene monomer. The third process includes reacting a compound of the formula (13) with a compound of the formula (14) or (15), in the presence of a base, thereby producing the target styrene monomer.Type: ApplicationFiled: June 23, 2003Publication date: January 1, 2004Applicant: Central Glass Company, LimitedInventors: Shinichi Sumida, Takashi Kume, Sunao Koga, Haruhiko Komoriya
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Patent number: 6528605Abstract: A diyne-containing (co)polymer which is soluble in organic solvents, has excellent processability, and gives a cured coating film excellent in heat resistance, solvent resistance, and low-dielectric characteristics, and mechanical strength; processes for producing the same; and a cured film. The diyne-containing (co)polymer contains at least 10 mol % repeating units represented by the following formula (1) and has a weight-average molecular weight of from 500 to 1,000,000: &Brketopenst;C≡C&Parenopenst;Y&Parenclosest;nC≡C—Ar&Brketclosest; (1) wherein Y represents a specific bivalent organic group; Ar represents a bivalent organic group; and n represents 1.Type: GrantFiled: November 8, 2000Date of Patent: March 4, 2003Assignee: JSR CorporationInventors: Toshiyuki Akiike, Matthias Patz, Masayuki Takahashi, Kohei Goto, Michinori Nishikawa, Takashi Okada, Kinji Yamada
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Patent number: 6399842Abstract: 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 characteristic optical and other properties of polyacetylenes.Type: GrantFiled: August 23, 2000Date of Patent: June 4, 2002Assignee: Board of Trustees of Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang
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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: 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: 5728917Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.Type: GrantFiled: October 30, 1995Date of Patent: March 17, 1998Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, SonBinh T. Nguyen
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Patent number: 5436361Abstract: A process for synthesizing enediynes is provided. Specifically, the formed enediynes contain a hex-3-ene-1,5-diynyl group. Production of the enediynes involves adding a base to a propargylic halide in the presence of a chelating agent, which causes a carbenoid coupling-elimination sequence of the propargylic halides. A carbenoid destabilizing agent can also be added to the reaction mixture in order to enhance yield. Acyclic and cyclic enediynes can be synthesized according to this process. The enediynes are useful compounds that can be used in a variety of applications including use in the production of anti-tumor agents.Type: GrantFiled: April 22, 1994Date of Patent: July 25, 1995Assignee: Clemson UniversityInventors: Graham B. Jones, Robert S. Huber
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Patent number: 5264511Abstract: Monomers, B-stage polymers, C-stage polymers, cured polymers and electricy conducting polymers of acetylene-terminated aromatic monomers containing three benzene rings separated by ethylene groups are disclosed. These new polymers can withstand aggressive environments and are particularly adapted for use in high temperature composites in addition to the utilization of their electrical conducting properties. Preparation of these materials is accomplished by melt polymerization and heat treatment at high temperatures.Type: GrantFiled: June 30, 1992Date of Patent: November 23, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Theordore R. Walton
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Patent number: 5162562Abstract: A process is provided for making metallated and substituted alkynes from feedstocks which include alkadienes containing allenic unsaturation or such alkadienes in a mixture with alkynes having either internal or terminal unsaturation, such as a mixture of propadiene and propyne. This reaction involves an initial step in which the allenic hydrocarbon and any internal alkyne is isomerized and simultaneously the resultant terminal alkynes are metallated with an alkali metal. The reaction is carried out at relatively low temperatures in a suitable inert solvent such as diethylether. When metallation is complete the reaction mixture can be contacted directly with any suitable electrophile, such as a halo silane, for example, chlorotrimethylsilane, and the alkali metal on the terminal alkyne is replaced with the desired substituent. The products thus formed are useful as monomers for preparing polymers having a variety of properties, for example, as asymmetric membranes for gas separation.Type: GrantFiled: May 9, 1991Date of Patent: November 10, 1992Assignee: Air Products and Chemicals, Inc.Inventors: Frederick L. Herman, Ann C. L. Savoca, Mark L. Listemann
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Patent number: 5082961Abstract: A novel and efficient method is proposed for the synthetic preparation of a long-chain alkynyl compound in a one-pot reaction without isolating the intermediate from the reaction mixture. The inventive method comprises the steps of: (a) a Grignard coupling reaction of an .omega.-halogeno-1-alkynyl magnesium halide compound of the general formula X.sup.1 MgC.tbd.C(CH.sub.2).sub.n X.sup.2, in which X.sup.1 is a halogen atom, X.sup.2 is an atom of Br or I and n is 3 to 10, and a Grignard reagent of the general formula RMgX.sup.1, in which R is a group selected from the class consisting of alkyl groups, alkenyl groups, alkynyl groups, alkapolyenyl groups, aryl groups and hydrocarbon groups having protected hydroxy group to give an intermediate compound of the general formula X.sup.1 MgC.tbd.C(CH.sub.2).sub.n R; (b) subjecting the intermediate compound to a reaction with a reactant selected from the class consisting of C.sub.2 -synthons, C.sub.Type: GrantFiled: September 11, 1990Date of Patent: January 21, 1992Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Akira Yamamoto
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Patent number: 5053580Abstract: Metal oxide powders comprised of Cr(III) oxide, Ti(IV) oxide, V(V) oxide, or mixtures of these, or metal mixed oxides comprised of Cr(III) oxide and Ti(IV) oxide and V(V) oxide, or their mixtures. They have BET surfaces of 5-50m.sup.2 /g and mean particle diameters of 25-350 nm and are useful to increase conversion and selectivity in the manufacture of mono-olefins by catalytic dehydrogenation of saturated hydrocarbons. The metal oxide powders are produced from mixtures of the vaporized metal compounds chromyl chloride, titanium tetrachloride, and vanadyl chloride, in the presence of certain gases by laser pyrolysis.Type: GrantFiled: May 7, 1990Date of Patent: October 1, 1991Assignee: Veba Oel AktiengesellschaftInventors: Bernhard Schramm, Jurgen Kern, Harald Schwahn, August-Wilhelm Preuss, Klaus Gottlieb, Hartmut Bruderreck
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Patent number: 4871868Abstract: A method of producing substituted acetylenic compounds which comprises: reacting an organic compound having the general formula ofA--X (I)wherein A represents a saturated or unsaturated aliphatic hydrocarbon residue of 1-20 carbon atoms which may have one or more substituents inactive in the reaction, and X represents a halogen atom or an arylsulfonyloxy group, with a metal acetylide having the general formula ofM--C.tbd.C--B (II)wherein M represents an alkali metal, and B represents (a) a hydrogen, (b) a saturated or unsaturated hydrocarbon residue which may have one or more substituents inactive in the reaction, or (c) a saturated or unsaturated hydrocarbon residue which has a substituent having the general formula of--C.tbd.C--M (III)wherein M represents an alkali metal, in the presence of an alkyl-2-imidazolidinone having the general formula of ##STR1## wherein R.sup.1 and R.sup.2 independently represent a lower alkyl, and R.sup.3 represents a hydrogen or a lower alkyl.Type: GrantFiled: March 3, 1988Date of Patent: October 3, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Yuzuru Saito, Kokichi Yoshida
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Patent number: 4835272Abstract: A process for formation of a base, which comprises reacting an acetylide compound with a salt. The acetylide compound has the following formula:(R--C.tbd.C--).sub.n Mwherein R is a monovalent group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heterocyclic group, each of which may have one or more substituent groups; M is an n-valent transition metal atom; and n is 1, 2 or 3. The salt is composed of an anion having an affinity for the transition metal (M) (the affinity of the anion for the transition metal is more than that of the acetylide anion (R--C.tbd.C.crclbar.)), and a cation derived from one selected from the group consisting of an alkali metal, an alkaline earth metal, ammonia and an organic base. A light-sensitive material containing the acetylide compound and the salt is also disclosed.Type: GrantFiled: July 16, 1987Date of Patent: May 30, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Shunichi Ishikawa, Ken Kawata
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Patent number: 4822940Abstract: The present invention provides for a process for converting a feedstock comprising ethylene and/or acetylene to a product comprising liquid hydrocarbons. The process comprises maintaining said feedstock at a temperature in the range of about 700.degree. C. to about 1000.degree. C. for about 100 to about 1000 milliseconds to provide for said conversion. In one embodiment, the feedstock further comprises hydrogen. In another embodiment the feedstock comprises the product made by the process comprising heating a gaseous mixture comprising (i) hydrogen and (ii) natural gas and/or at least one light hydrocarbon at a temperature of at least about 1250.degree. C. for an effective period of time to provide said feedstock. In still another embodiment, the feedstock further comprises natural gas and/or at least one light hydrocarbon in addition to said ethylene and/or acetylene.Type: GrantFiled: August 17, 1987Date of Patent: April 18, 1989Assignee: The Standard Oil CompanyInventors: Alan A. Leff, Joseph E. Metcalfe, Louis J. Velenyi, Christos Paparizos
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Patent number: 4672144Abstract: Methane is converted to higher, more reactive, hydrocarbon products by a diffusion flame. Methane is converted to C.sub.2 + products by pyrolysis in the interior of the flame with oxidizing gas flowing outside of the flame. More reactive products are withdrawn from the center of the flame by a probe tube and cooled by the flowing oxidizing gas to stop the reaction.Type: GrantFiled: November 8, 1985Date of Patent: June 9, 1987Assignee: Mobil Oil CorporationInventor: Gary J. Green
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Patent number: 4672143Abstract: A diffusion flame reactor for cracking hydrocarbon gas has an oxygen-deficient zone in the center of the flame or in the center of an array of flames. Propane, n-octane, iso-octane and decalin are cracked to ethylene, acetylene, propylene, butenes, and butadienes which are withdrawn from the flame.Type: GrantFiled: November 8, 1985Date of Patent: June 9, 1987Assignee: Mobil Oil CorporationInventors: Gary J. Green, Tsoung-Y Yan
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Patent number: 4644085Abstract: The invention relates to a new anti-cancer chemical compound which has been called rooperol and certain derivatives thereof of the general formula ##STR1## in which A is chosen from the group including a phenyl group, a substituted phenyl group and --CH.sub.2 --O--R.sup.5 where R.sup.5 =H, an alkyl (C.sub.1 -C.sub.5), aralkyl or acyl substituent; R.sup.1 and R.sup.2 are chosen from substituents including H for both or singly if one of them is --OH, --NH.sub.2, --SH, ##STR2## or taken together R.sup.1 and R.sup.2 are =0; R.sup.3 is H or ##STR3## where R.sup.6 is an alkyl group (C.sub.1 -C.sub.7); either of R.sup.4 or B are chosen from substituents including H, ##STR4## a phenyl group, substituted phenyl group or a furyl group.Type: GrantFiled: June 4, 1985Date of Patent: February 17, 1987Assignee: Rooperol (NA) NVInventors: Siegfried Drewes, Roelof W. Liebenberg
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Patent number: 4503205Abstract: A soluble polyene polymer and a method of making the same are disclosed. The polymer is of the class suitable for doping to produce an electrically conductive polymer. The method is generally applicable to acetylenic and aromatic monomers, proven examples of which include acetylene, benzene, anthracene and napthalene. In accordance with the method, the monomer is dissolved in arsenic trifluoride. Arsenic pentafluoride is then introduced into the solution to induce polymerization by what is speculated to be an ionic polymerization reaction. The resulting polymer differs from other polyene polymers in that it is soluble in common organic solvents, and further in that it can be melted without undergoing decomposition, thereby rendering it particularly suitable for processing to form various polymeric articles.Type: GrantFiled: December 16, 1983Date of Patent: March 5, 1985Assignee: The United States of America as represented by the United States Department of EnergyInventors: Mahmoud Aldissi, Raimond Liepins
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Patent number: 4384158Abstract: The invention provides a novel synthetic method for the preparation of an alkyne-1 compound of the general formula R(CH.sub.2).sub.n C.tbd.CH, in which R is a monovalent hydrocarbon group and n is an integer of 4, 5 or 6, which compound is useful as an intermediate of various organic compounds or, in particular, of several sexual pheromone of noxious insects expected to give a promising means for the extermination of the insects. The method comprises reacting an .omega.-bromo-1-alkyne compound of the formula Br(CH.sub.2).sub.n C.tbd.CH, e.g. 8-bromo-1-octyne, with a Grignard reagent of the formula RMgX, e.g. cis-3-octenylmagnesium chloride, in tetrahydrofuran, preferably, in the presence of a catalyst which is dilithium copper tetrachloride or lithium copper dichloride.Type: GrantFiled: July 14, 1981Date of Patent: May 17, 1983Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshinobu Ishihara, Akira Yamamoto, Kenichi Taguchi
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Patent number: 4177220Abstract: Vinyl acetylene is coupled with butadiene to selectively produce 1-octen-7-yne by reacting the vinyl acetylene with butadiene in the presence of formic acid or a salt thereof, optionally a solvent and a catalyst comprising palladium complexed with tertiary organophosphorus ligand.Type: GrantFiled: November 6, 1978Date of Patent: December 4, 1979Assignee: Shell Oil CompanyInventor: Kenzie Nozaki