Triple-bond Product Patents (Class 585/534)
  • Patent number: 5705167
    Abstract: 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: Grant
    Filed: April 26, 1995
    Date of Patent: January 6, 1998
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5663467
    Abstract: An improved synthesis of cyclopropylacetylene involving cyclization of 5-halo-1-pentyne in strong base is disclosed, and is useful for preparing compounds with a cyclopropylethynyl substituent, such as an intermediate for a highly potent HIV reverse transcriptase inhibitor or other pharmaceutically active compounds.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: September 2, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Andrew S. Thompson, Edward G. Corley, Martha Huntington
  • Patent number: 5436361
    Abstract: 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: Grant
    Filed: April 22, 1994
    Date of Patent: July 25, 1995
    Assignee: Clemson University
    Inventors: Graham B. Jones, Robert S. Huber
  • Patent number: 5185454
    Abstract: 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: Grant
    Filed: October 2, 1990
    Date of Patent: February 9, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Axel Bader, Dieter Arlt
  • Patent number: 5162596
    Abstract: 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: Grant
    Filed: February 14, 1992
    Date of Patent: November 10, 1992
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Akira Yamamoto, Mitsuyoshi Oshima
  • Patent number: 5082961
    Abstract: 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: Grant
    Filed: September 11, 1990
    Date of Patent: January 21, 1992
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Akira Yamamoto
  • Patent number: 5062998
    Abstract: 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: Grant
    Filed: April 23, 1990
    Date of Patent: November 5, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Frederick L. Herman, Ann C. L. Savoca, Mark L. Listemann
  • Patent number: 4952742
    Abstract: 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: Grant
    Filed: May 10, 1989
    Date of Patent: August 28, 1990
    Assignee: BASF Aktiengsellschaft
    Inventors: Michael Hesse, Rainer Becker
  • Patent number: 4795835
    Abstract: 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: Grant
    Filed: March 3, 1988
    Date of Patent: January 3, 1989
    Assignee: GAF Corporation
    Inventor: Robert Schenfele
  • Patent number: 4795850
    Abstract: 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: Grant
    Filed: November 24, 1987
    Date of Patent: January 3, 1989
    Assignee: The British Petroleum Company p.l.c.
    Inventor: Andrew F. Dyke
  • Patent number: 4788379
    Abstract: 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: Grant
    Filed: October 1, 1982
    Date of Patent: November 29, 1988
    Assignee: GAF Corporation
    Inventors: Michael Katz, Frank Carluccio, Gil Mallari, Kevin FitzPatrick, Ashok Desai, Robert Casciano, Jane Tsai
  • Patent number: 4754097
    Abstract: 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: Grant
    Filed: May 27, 1987
    Date of Patent: June 28, 1988
    Assignee: Ethyl Corporation
    Inventor: Steven P. Diefenbach
  • Patent number: 4704377
    Abstract: 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: Grant
    Filed: May 19, 1986
    Date of Patent: November 3, 1987
    Assignee: Ethyl Corporation
    Inventor: Steven P. Diefenbach
  • Patent number: 4698451
    Abstract: 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: Grant
    Filed: June 17, 1986
    Date of Patent: October 6, 1987
    Assignee: Ethyl Corporation
    Inventor: Steven P. Diefenbach
  • Patent number: 4604480
    Abstract: 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: Grant
    Filed: August 15, 1983
    Date of Patent: August 5, 1986
    Assignee: The Research Foundation of State University of New York
    Inventors: Eric Block, Mohammad Aslam
  • Patent number: 4567005
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: January 28, 1986
    Assignee: The Dow Chemical Company
    Inventor: Edmund P. Woo
  • Patent number: 4536603
    Abstract: 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: Grant
    Filed: December 22, 1983
    Date of Patent: August 20, 1985
    Assignee: Rockwell International Corporation
    Inventors: Kenneth M. Sprouse, Merlin D. Schuman, L. Paul Combs
  • Patent number: 4467118
    Abstract: 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: Grant
    Filed: March 3, 1982
    Date of Patent: August 21, 1984
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Steven A. Magennis, Vasile S. Wertheimer, Richard E. Naipawer
  • Patent number: 4441923
    Abstract: 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: Grant
    Filed: January 29, 1982
    Date of Patent: April 10, 1984
    Inventor: Rollan Swanson
  • Patent number: 4427595
    Abstract: 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: Grant
    Filed: July 16, 1981
    Date of Patent: January 24, 1984
    Assignee: Massachusetts Institute of Technology
    Inventor: Richard R. Schrock
  • Patent number: 4384158
    Abstract: 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: Grant
    Filed: July 14, 1981
    Date of Patent: May 17, 1983
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshinobu Ishihara, Akira Yamamoto, Kenichi Taguchi
  • Patent number: 4374290
    Abstract: 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: Grant
    Filed: November 9, 1981
    Date of Patent: February 15, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Karl H. Dotz
  • Patent number: 4367363
    Abstract: 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: Grant
    Filed: December 23, 1980
    Date of Patent: January 4, 1983
    Assignee: GAF Corporation
    Inventors: Michael Katz, Frank Carluccio, Gil Mallari, Kevin FitzPatrick, Ashok Desai, Robert Casciano, Jane Tsai
  • Patent number: 4362670
    Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of a palladium catalyst.
    Type: Grant
    Filed: September 3, 1981
    Date of Patent: December 7, 1982
    Assignee: The Dow Chemical Company
    Inventor: Edmund P. Woo
  • Patent number: 4320065
    Abstract: 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: Grant
    Filed: March 4, 1980
    Date of Patent: March 16, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Karl H. Dotz
  • Patent number: 4317659
    Abstract: 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: Grant
    Filed: January 24, 1980
    Date of Patent: March 2, 1982
    Assignee: Westinghouse Electric Corp.
    Inventor: Michael G. Down
  • Patent number: 4317905
    Abstract: 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: Grant
    Filed: May 21, 1979
    Date of Patent: March 2, 1982
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi