Triple-bond Product Patents (Class 585/534)
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Patent number: 5705167Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): ##STR1## 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: April 26, 1995Date of Patent: January 6, 1998Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 5663467Abstract: An improved synthesis of cyclopropylacetylene involving cyclization of 5-halo-1-pentyne in strong base is disclosed, and is useful for preparing compounds with a cyclopropylethynyl substituent, such as an intermediate for a highly potent HIV reverse transcriptase inhibitor or other pharmaceutically active compounds.Type: GrantFiled: January 23, 1995Date of Patent: September 2, 1997Assignee: Merck & Co., Inc.Inventors: Andrew S. Thompson, Edward G. Corley, Martha Huntington
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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: 5185454Abstract: Symmetrical diaryl-acetylenes can be prepared by reacting an aryl halide with acetylene in the presence of a palladium catalyst and a base. If the acetylene is introduced into the liquid reaction mixture using a high intensity gas dispersion means, the aryl halide used can be an aryl bromide.Type: GrantFiled: October 2, 1990Date of Patent: February 9, 1993Assignee: Bayer AktiengesellschaftInventors: Axel Bader, Dieter Arlt
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Patent number: 5162596Abstract: Disclosed is a novel ene-yne compound Z-12-heptadecen-1-yne expressed by the structural formula CH.sub.3 (CH.sub.2).sub.3 CH.sup.(Z) =CH(CH.sub.2).sub.9 C=CH, which is useful as an intermediate in the synthetic preparation of several diene compounds having activity as a sex pheromone of the insects belonging to the lepidopteran order, such as E,Z-2,13-octadecadienyl acetate and E,Z-2,13-octadecadienal, having two double bonds at the 2- and 13-positions. The inventive compound can be synthesized by the reaction of 1-bromo-Z-10-pentadecene with sodium acetylide dispersed in an organic solvent in the presence of liquid ammonia.Type: GrantFiled: February 14, 1992Date of Patent: November 10, 1992Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Akira Yamamoto, Mitsuyoshi Oshima
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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: 5062998Abstract: 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: April 23, 1990Date of Patent: November 5, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Frederick L. Herman, Ann C. L. Savoca, Mark L. Listemann
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Patent number: 4952742Abstract: Polyunsaturated hydrocarbons of the formula ##STR1## are prepared from unsaturated alcohols of the formula ##STR2## in the presence of zeolite catalysts, in particular zeolites of the pentasil type.Type: GrantFiled: May 10, 1989Date of Patent: August 28, 1990Assignee: BASF AktiengsellschaftInventors: Michael Hesse, Rainer Becker
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Patent number: 4795835Abstract: The process relates to the removal of copper contaminants from crude polyacetylenes containing up to 30 wt. % copper impurity by contacting a melt of the polyacetylene with aqueous hydrogen chloride to form an oil phase and an aqueous acid phase, separating said phases, treating the separated oil phase with from about 1 to about 10 volumes of water until subsequent oil and water phases are formed, agitating the separated oil phase while cooling to form a particulate product and drying said particles to recover purified polyacetylene.Type: GrantFiled: March 3, 1988Date of Patent: January 3, 1989Assignee: GAF CorporationInventor: Robert Schenfele
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Patent number: 4795850Abstract: A composition for use after reductive activation as a catalyst in the conversion of synthesis gas to hydrocarbons of carbon number greater than one, which composition before reductive activation has the formula:Ru.sub.a.A.sub.b.XO.sub.x (I)whereinA is an alkali metal,X is a rare earth metal,a is greater than zero and up to 5% w/w, based on the total weight of the composition,b is in the range from zero to 5% w/w, based on the total weight of the composition,x is a number such that the valence requirements of the other elements for oxygen is satisfied, and subject to the requirements of x, X constitutes the remainder of the composition,is produced by the steps of:(A) bringing together at a temperature below 50.degree. C.Type: GrantFiled: November 24, 1987Date of Patent: January 3, 1989Assignee: The British Petroleum Company p.l.c.Inventor: Andrew F. Dyke
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Patent number: 4788379Abstract: The process relates to the recovering of essentially pure acetylene from the gaseous out-put stream from a coal to acetylene conversion process. A plasma arc generator or other high energy type reactor can be used for the conversion to coal. The gaseous out-put stream is initially treated in an acid gas removal stage by absorbing HCN and H.sub.2 S in an organic solvent such as N-methyl pyrrolidone and scrubbing with a caustic agent such as NaOH to remove CO.sub.2. In a second stage, the gaseous out-put stream is scrubbed with the organic solvent to provide a sweet gas treatment and remove essentially pure acetylene as a product. In a third stage, the second stage gases are first hydrogenated, then desulfurized and then methanated. The out-put from the third stage is recycled to the coal to acetylene conversion process. In a fourth stage, the organic solvent from said second stage is refined and recycled to the first stage and/or second stage.Type: GrantFiled: October 1, 1982Date of Patent: November 29, 1988Assignee: GAF CorporationInventors: Michael Katz, Frank Carluccio, Gil Mallari, Kevin FitzPatrick, Ashok Desai, Robert Casciano, Jane Tsai
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Patent number: 4754097Abstract: Described are novel bimetallic complexes particularly useful as homogeneous catalysts for the metathesis of alkynes and metathesizable functionally substituted alkynes, and methods for the preparation of such complexes. The complexes are formed from (i) a Group VI-B metal compound having (a) quadruple metal to metal bonds between a pair of Group VI-B metal atoms at least one of which has an atomic number above 24, and (b) four monovalent anions with a k.sub.A greater than 10.sup.-14, and (ii) a Group III-A phenoxide, a Group III-A alkoxide or a Group IV-B metal alkoxide. Displacement of two of the anions appears to occur during formation of the complex. Usually the complexes can be produced very easily and quickly. All that is required is to establish intimate contact between components (i) and (ii), preferably in an innocuous liquid organic solvent. Addition of a small amount of a nitrile gives a faster and cleaner reaction. In some cases use of slightly elevated temperatures is desirable.Type: GrantFiled: May 27, 1987Date of Patent: June 28, 1988Assignee: Ethyl CorporationInventor: Steven P. Diefenbach
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Patent number: 4704377Abstract: Described are novel bimetallic complexes particularly useful as homogeneous catalysts for the metathesis of alkynes and metathesizable functionally substituted alkynes, and methods for the preparation of such complexes. The complexes are formed from (i) a Group VI-B metal compound having (a) quadruple metal to metal bonds between a pair of Group VI-B metal atoms at least one of which has an atomic number above 24, and (b) four monovalent anions with a k.sub.A greater than 10.sup.-14, and (ii) a Group III-A phenoxide, a Group III-A alkoxide or a Group IV-B metal alkoxide. Displacement of two of the anions appears to occur during formation of the complex. Usually the complexes can be produced very easily and quickly. All that is required is to establish intimate contact between components (i) and (ii), preferably in an innocuous liquid organic solvent. Addition of a small amount of a nitrile gives a faster and cleaner reaction. In some cases use of slightly elevated temperatures is desirable.Type: GrantFiled: May 19, 1986Date of Patent: November 3, 1987Assignee: Ethyl CorporationInventor: Steven P. Diefenbach
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Patent number: 4698451Abstract: Described are novel bimetallic complexes particularly useful as homogeneous catalysts for the metathesis of alkynes, and methods for the preparation of such complexes. The complexes are formed from (i) a dirhenium halide having (a) a double or triple bond between a pair of rhenium atoms, and (b) a bis(dihydrocarbylphosphino)alkane coordinated therewith, and (ii) a Group III-A alkoxide in which the alkoxy groups are perfluorinated or are substantially perfluorinated. The complexes can be produced very easily and quickly. All that is required is to establish intimate contact between components (i) and (ii), preferably in an innocuous liquid organic solvent. 3-Heptyne was metathesized in good yields by means of the complex formed from Re.sub.2 Cl.sub.4 (dppm).sub.2 and Al(OCH(CH.sub.3).sub.2).sub.3, and the complex formed from Re.sub.2 Cl.sub.6 (dppm).sub.2 and Al(OCH(CF.sub.3).sub.2).sub.3 (dppm=bis(diphenylphosphino))methane).Type: GrantFiled: June 17, 1986Date of Patent: October 6, 1987Assignee: Ethyl CorporationInventor: Steven P. Diefenbach
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Patent number: 4604480Abstract: A method for the preparation of a first sulfone compound of the formula: ##STR1## wherein R.sub.a is ##STR2## where R.sub.b is Br and R.sub.c is H except that R.sub.b and R.sub.c together may be an electron pair when R.sub.6 is a radical of the formula: ##STR3## wherein X.sub.1 is independently chlorine, bromine or iodine and R.sub.1 and R.sub.2 are independently at each occurrence hydrogen or, substituted or unsubstituted, phenyl or alkyl where the substituents are halogen or alkoxy or additional --SO.sub.2 Br groups; provided that, each carbon atom of R.sub.1 or R.sub.2 which contains --SO.sub.2 Br also contains an X.sub.1 group and wherein R.sub.3 through R.sub.9 are independently --OZ,--C.sub.6 M.sub.5,--Z,--SiZ.sub.3 or --X.sub.2, where Z is hydrogen or substituted or unsubstituted phenyl, alkyl, alkenyl or alkynyl; X.sub.2 is chlorine, bromine, iodine or fluorine; M is independently at each occurrence Z or X.sub.2 ; R.sub.3 and R.sub.4 may together be an electron pair; two or more of R.sub.3, R.sub.Type: GrantFiled: August 15, 1983Date of Patent: August 5, 1986Assignee: The Research Foundation of State University of New YorkInventors: Eric Block, Mohammad Aslam
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Patent number: 4567005Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of an iron, cobalt, nickel, ruthenium, rhodium, osmium, iridium or platinum catalyst.Type: GrantFiled: April 22, 1983Date of Patent: January 28, 1986Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4536603Abstract: A process wherein coal is reacted with a hot gas stream to produce acetylene. The process comprises the sequential steps of reacting a fuel, oxygen and steam under controlled conditions of temperature to produce a hot gas stream principally comprising hydrogen, carbon monoxide and steam along with minor amounts of carbon dioxide, and essentially free of O, OH and O.sub.2. The hot gas stream is accelerated to a high velocity and impinged upon a stream of particulate bituminous or subbituminous coal and thereafter the mixture of hot gas and coal is decelerated to a velocity of from about 150 to 300 feet per second. The amounts of the streams of particulate coal and hot gas are controlled to produce in the reaction zone a pressure in the range of from about 10 to 100 psia and a temperature of from about 1800.degree. to 3000.degree. F.Type: GrantFiled: December 22, 1983Date of Patent: August 20, 1985Assignee: Rockwell International CorporationInventors: Kenneth M. Sprouse, Merlin D. Schuman, L. Paul Combs
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Patent number: 4467118Abstract: There is disclosed a novel process for converting allylic amines, having a hydrogen bonded to a carbon .delta. to the amino group, to a diene in the presence of a zero valent palladium phosphine complex and a weak acid. The process has been used to make novel compositions containing 7-methoxy-3,7-dimethyloctadienes which are useful as odorants and flavorants.Type: GrantFiled: March 3, 1982Date of Patent: August 21, 1984Assignee: Givaudan CorporationInventors: Alan J. Chalk, Steven A. Magennis, Vasile S. Wertheimer, Richard E. Naipawer
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Patent number: 4441923Abstract: Disclosed is a combinative integrated chemical process using inorganic reactants and yielding, if desired, organic products. The process involves first the production of elemental potassium by the thermal or thermal-reduced pressure decomposition of potassium oxide or potassium sulfide and distillation of the potassium. This elemental potassium is then used to reduce ores or ore concentrates of copper, zinc, lead, magnesium, cadmium, iron, arsenic, antimony or silver to yield one or more of these less active metals in elemental form. Process potassium can also be used to produce hydrogen by reaction with water or potassium hydroxide. This hydrogen is reacted with potassium to produce potassium hydride. Heating the latter with carbon produces potassium acetylide which forms acetylene when treated with water. Acetylene is hydrogenated to ethene or ethane with process hydrogen. Using Wurtz-Fittig reaction conditions, the ethane can be upgraded to a mixture of hydrocarbons boiling in the fuel range.Type: GrantFiled: January 29, 1982Date of Patent: April 10, 1984Inventor: Rollan Swanson
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Patent number: 4427595Abstract: Tungsten compounds of the formula:[L.sub.Y X.sub.n+3 W.tbd.CR.sup.3 ].sup.n- (M.sup.+).sup.nwhereinR.sup.3 is an alkyl or aryl;L is a moiety of the formula ZR.sup.4 R.sup.5 R.sup.6, (O)ZR.sup.4 R.sup.5 R.sup.6, ZR.sup.4 R.sup.5 (OR.sup.6), ZR.sup.4 (OR.sup.5) (OR.sup.6) or Z(OR.sup.4) (OR.sup.5) (OR.sup.6); wherein Z is a group 5 element including N, P or As and R.sup.4, R.sup.5 and R.sup.6 can be the same or different and are alkyl, aralkyl or aryl;X is F, Cl, Br, I, OR.sup.4, NR.sup.4 R.sup.5 or SR.sup.4 ;M.sup.+ is a metallic or organic cation; alkyl has 1-10 carbons, aralkyl has 7-10 carbons and aryl has 6-10 carbons;n is 0 or 1, and y is 0, 1 or 2, with the proviso that:y is 0 when X is OR.sup.4, NR.sup.4 R.sup.5 or SR.sup.4, and n=0;y is 0 when X is OR.sup.4, F, Cl, Br or I, and n=1.These compounds will transform unsymmetric acetylenes into a mixture containing the unsymmetric acetylene and the two possible symmetric acetylenes in their thermodynamically determined relative amounts at equilibrium.Type: GrantFiled: July 16, 1981Date of Patent: January 24, 1984Assignee: Massachusetts Institute of TechnologyInventor: Richard R. Schrock
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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: 4374290Abstract: A process for preparing vitamins of the vitamin K.sub.1 and K.sub.2 series in their E-isomeric form through the reaction of a phenylcarbene metal complex with an enyne and intermediates in this synthesis.Type: GrantFiled: November 9, 1981Date of Patent: February 15, 1983Assignee: Hoffmann-La Roche Inc.Inventor: Karl H. Dotz
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Patent number: 4367363Abstract: The process relates to the recovering of essentially pure acetylene from the gaseous out-put stream from a coal to acetylene conversion process. A plasma arc generator or other high energy type reactor can be used for the conversion to coal. The gaseous out-put stream is initially treated in an acid gas removal stage by absorbing HCN and H.sub.2 S in an organic solvent such as N-methyl pyrrolidone and scrubbing with a caustic agent such as NaOH to remove CO.sub.2. In a second stage, the gaseous out-put stream is scrubbed with the organic solvent to provide a sweet gas treatment and remove essentially pure acetylene as a product. In a third stage, the second stage gases are first hydrogenated, then desulferized and then methanated. The out-put from the third stage is recycled to the coal to acetylene conversion process. In a fourth stage, the organic solvent from said second stage is refined and recycled to the first stage and/or second stage.Type: GrantFiled: December 23, 1980Date of Patent: January 4, 1983Assignee: GAF CorporationInventors: Michael Katz, Frank Carluccio, Gil Mallari, Kevin FitzPatrick, Ashok Desai, Robert Casciano, Jane Tsai
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Patent number: 4362670Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of a palladium catalyst.Type: GrantFiled: September 3, 1981Date of Patent: December 7, 1982Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4320065Abstract: A process for preparing vitamins of the vitamin K.sub.1 and K.sub.2 series in their E-isomeric form through the reaction of a phenylcarbene metal complex with an enyne and intermediates in this synthesis.Type: GrantFiled: March 4, 1980Date of Patent: March 16, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Karl H. Dotz
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Production of hydrogen, acetylene and ammonia gases from lithium reaction with hydrocarbon materials
Patent number: 4317659Abstract: A method of producing H.sub.2 and C.sub.2 H.sub.2 gases comprises the steps of drying a hydrocarbon biomass material to remove water without carbonization, reacting the dried hydrocarbon biomass with a stoichiometric excess of molten lithium metal to produce lithium salts comprising LiH and Li.sub.2 C.sub.2 and then hydrolyzing the lithium salts to produce a gaseous mixture comprising H.sub.2 and C.sub.2 H.sub.2.Type: GrantFiled: January 24, 1980Date of Patent: March 2, 1982Assignee: Westinghouse Electric Corp.Inventor: Michael G. Down -
Patent number: 4317905Abstract: A process is disclosed for preparing aliphatic compounds containing two conjugated double bonds cis-cis or cis-trans, characterized in that a compound of the general formula ##STR1## (in which R is H, alkyl from C.sub.1 to C.sub.10, or OY in which Y is a protective group selected from the class consisting of tetrahydropyranyl and 1-ethoxyethyl; X is an ester function selected from the class consisting of the acetates) is reacted with an alkyl-magnesium halide of the general formula:Z--Mg--R.sup.1 (II)(in which Z is chlorine, bromine or iodine, and R.sup.1 is a C.sub.1 -C.sub.10 alkyl group, or a group (CH.sub.2).sub.n OY in which Y has the same meaning as in formula (I), and n is a number from 3 to 10) in the presence of Li.sub.2 CuCl.sub.4, CuCl, CuBr, or CuI at temperatures ranging from about -30.degree. to +10.degree. C. in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula:R--CH.sub.2 --C.tbd.C--CH.dbd.CH--CH.sub.2 R.sup.Type: GrantFiled: May 21, 1979Date of Patent: March 2, 1982Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi