Acyclic Carbon To Carbon Unsaturation Containing Patents (Class 570/189)
  • Patent number: 5001276
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: March 19, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4990703
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 5, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4935560
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: June 19, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4933488
    Abstract: Described are triisobutylene alcohols and esters and halogenated intermediates for preparing same defined according to the generic structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 " and R.sub.2 " are the same or different and each represents hydrogen, chloro, bromo, hydroxyl or a C.sub.1 -C.sub.3 acyloxy with the provisos that when the dashed line in the 4--4' position is a carbon-carbon double bond then R.sub.1 " is hydrogen and R.sub.2 " is not hydrogen; and R.sub.1 " and R.sub.2 " are not both hydrogen.Also described are the uses of the triisobutylene alcohols and esters in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: June 12, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
  • Patent number: 4924026
    Abstract: Described are triisobutylene alcohols and esters and halogenated intermediates for preparing same defined according to the generic structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 " and R.sub.2 " are the same or different and each represents hydrogen, chloro, bromo, hydroxyl or a C.sub.1 -C.sub.3 acyloxy with the provisos that when the dashed line in the 4--4' position is a carbon-carbon double bond then R.sub.1 " is hydrogen and R.sub.2 " is not hydrogen, and R.sub.1 " and R.sub.2 " are not both hydrogen.Also described are the uses of the triisobutylene alcohols and esters in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: May 8, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
  • Patent number: 4918252
    Abstract: A novel and efficient synthetic route is proposed for the preparation of (Z,E)-9,12-tetradecadienyl acetate as a sex pheromone compound used for population control of the pest insects belonging to the genus of Spodoptera via an intermediate 1-halo-(Z,E)-7,10-dodecadiene, which is a novel compound not known in the prior art. This novel compound is synthesized by reacting a Grignard reagent XMgC.tbd.C(CH.sub.2).sub.6 X,X being Cl or Br, with (E)-2-butenyl chloride or bromide to form an ene-yne compound of the formula CH.sub.3 CH.dbd..sup.(E) CHCH.sub.2 C.tbd.C(CH.sub.2).sub.6 X and then partially hydrogenating this ene-yne compound.
    Type: Grant
    Filed: February 5, 1989
    Date of Patent: April 17, 1990
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Akira Yamamoto
  • Patent number: 4870219
    Abstract: Novel styryl-tetrahydromaphythalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: September 26, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4827056
    Abstract: Chlorinated olefins of general formula (I), ##STR1## wherein R is an alkyl, aralkyl, or alkenyl group substituted or not substituted by a lower acyloxy, lower alkyloxy, alkenyloxy or benzyloxy group, are prepared by the reaction of hypochlorous acid, generated by the reaction of sodium hypochlorite with a strong mineral acid, and olefins of general formula (II), ##STR2## wherein R is the same as defined above, in a two-phase system of water phase and organic solvent phase, not being miscible with water.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: May 2, 1989
    Assignee: Kuraray Company Ltd.
    Inventors: Shigeaki Suzuki, Toshiki Mori, Takashi Onishi, Yoshiji Fujita
  • Patent number: 4818442
    Abstract: A process for the disproportionation of olefins comprising contacting said olefins under suitable reaction conditions with a neutral-carbene complex catalyst and then using anhydrous ammonia to effect separation of the catalyst and the organic products.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: April 4, 1989
    Assignee: Phillips Petroleum Company
    Inventors: John W. Vanderveen, Dennis S. Banasiak
  • Patent number: 4804763
    Abstract: The reactions of chlorination of the pyridine compounds are conducted by means of molecular chlorine, with the use, as free-radical forming initiator, of a decachlorobutane or an octachlorobutene such as octachlorobutene-1 or a crude mixture of these chlorine-containing products obtained by additive chlorination of hexachlorobutadiene-1,3.Good rates of conversion are obtained, and good yields at moderate temperatures.The method is applied, for example, to the chlorination of pyridine and beta-picoline.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: February 14, 1989
    Assignee: Reilly Chemicals, S.A.
    Inventor: James Franklin
  • Patent number: 4734524
    Abstract: A pheromonal compound produced by the western corn rootworm has been identified as 8-methyl-2-decanol propanoate (8-M-2-DP) having the structural formula: ##STR1## A synthesis has been devised for racemic 8-M-2-DP which demonstrates activity toward the western corn rootworm comparable to its natural counterpart. Other diabroticites including the Mexican corn rootworm and the northern corn rootworm also respond to the synthetic compound. By attracting rootworms to field traps, 8-M-2-DP is a useful tool for the monitoring and control of these major agricultural pests.
    Type: Grant
    Filed: August 16, 1982
    Date of Patent: March 29, 1988
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Paul L. Guss, James H. Tumlinson, III, Philip E. Sonnet, Adron T. Proveaux
  • Patent number: 4713458
    Abstract: Ketones and aldehydes are converted to ethenylidene-containing compounds by reaction thereof with dimethyl carbonate and a phosphine compound.
    Type: Grant
    Filed: August 21, 1984
    Date of Patent: December 15, 1987
    Assignee: The Dow Chemical Company
    Inventors: Kevin A. Frazier, James M. Renga
  • Patent number: 4686310
    Abstract: Described are the 2-isopropenyl-5-methylcyclopentanealkanols and esters thereof having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.2 -C.sub.3 acyl and wherein n represents 0 or 1 and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, cosmetic compositions, fabric softener compositions, fabric softener articles and hair preparations.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: August 11, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventor: John B. Hall
  • Patent number: 4668710
    Abstract: Included are trihalovinyl polyol ethers. The compositions have pendant 1,2,2-trihaloethenyl moieties. The compositions may be low viscosity oils or highly polymeric such as incorporated with a urethane or other polymers. One of the uses of the compositions is as flame retardants which may have high thermal stability and scorch resistance.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: May 26, 1987
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, William J. Kruper, Jr.
  • Patent number: 4665221
    Abstract: An improved process for the preparation of primary terpenoid alcohols, e.g. 6,7-dihydrogeraniol and phytol, and of their esters with formic acid. The terpenoid formates are obtained very advantageously by reacting the corresponding tert.-vinylcarbinols with more than 2 moles, per mole of vinylcarbinol, of aqueous formic acid of more than 70 percent strength by weight, or with anhydrous formic acid, at from 5.degree. to 100.degree. C. The primary terpenoid alcohols themselves are obtained from their formates by trans-esterification with a low-boiling alcohol in the presence of a catalytic amount of a strong base. The products are valuable compounds. For example, 6,7-dihydrogeraniol is used as a scent and phytol is used as a perfume fixative and as a starting material for the synthesis of naturally occurring materials.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: May 12, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Thoemel, Werner Hoffmann
  • Patent number: 4665244
    Abstract: Hexadecene derivatives of the formulae: ##STR1## and ##STR2## in which X and X.sub.1, which may be identical or different, each represent hydrogen or chlorine, and their mixtures, are useful in the preparation of tocopherol and tocopherol acetate.
    Type: Grant
    Filed: September 19, 1985
    Date of Patent: May 12, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Pierre Chabardes, Michel Mulhauser
  • Patent number: 4661648
    Abstract: The substitution chlorination reactions of organic compounds are carried out by means of molecular chlorine, using, as a radical initiator, decachlorobutane or an octachlorobutane such as octachlorobut-1-ene or a mixture containing these two products.Good degrees of conversion and good yields are obtained at moderate temperatures.The process is, for example, applicable to the substitution chlorination of benzene and of chloroform.
    Type: Grant
    Filed: August 15, 1985
    Date of Patent: April 28, 1987
    Assignee: Solvay & Cie (Societe Anonyme)
    Inventor: James Franklin
  • 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: 4571438
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: February 18, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Dennis S. Banasiak
  • Patent number: 4540826
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: September 10, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Jim D. Byers
  • Patent number: 4514409
    Abstract: 5-Aryloxy-5-azolyl-3,3-dimethylpent-1-en-4-ones and -ols of the formula ##STR1## in which Ar is an optionally substituted aryl group,Az is a 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl or imidazol-1-yl group, andB is a keto group of a CH(OH) grouping,or addition products thereof with physiologically acceptable acids or metal salts are suitable for use as plant protection agents, and can be employed with particularly good success for combating those fungi which cause powdery mildew diseases, thus for combating Erysiphe species, Sphaerotheca species and Podosphaera species, and for combating diseases of rice.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: April 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Manfred Jautelat, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4496483
    Abstract: S-(2-Halo-2-propen-l-yl) N-(hexamethyleneimino)thiolcarbamates in which the halo is preferably bromo or chloro. The compounds have biological activity and may be used, for example, as selective pre-emergence herbicides.
    Type: Grant
    Filed: September 12, 1983
    Date of Patent: January 29, 1985
    Assignee: United States Borax & Chemical Corporation
    Inventor: Don L. Hunter
  • Patent number: 4471096
    Abstract: Vinyl chloride polymers are prepared by polymerizing a monomer component that comprises vinyl chloride in an aqueous medium in the presence of a free radical-generating polymerization initiator and 0.01% to 2% by weight, based on the weight of the monomer component, of a chain-transfer agent that is a mercapto organic compound having at least one beta-ether linkage. The process can be used to produce low molecular weight vinyl chloride polymers.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: September 11, 1984
    Assignee: Tenneco Polymers, Incorporated
    Inventors: Zaev Sharaby, Donald Goodman
  • Patent number: 4350824
    Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or the two radicals R.sup.3 together are alkanediyl,in the presence of at least an equimolar amount of a phosphorous acid triamide of the formulaP(NR.sup.4.sub.2).sub.3in whichR.sup.4 each independently is an alkyl radical, or the two radicals R.sup.4 together are alkanediyl.Advantageously,R.sup.1 is hydrogen,R.sup.2 a C.sub.2 to C.sub.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: September 21, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz
  • Patent number: 4343742
    Abstract: 2,3-Perfluoro-1,4-dioxanes of the formula I ##STR1## wherein X and Y independently from one another mean F or CF.sub.3, are manufactured by reacting carbonyl compounds of the formula II ##STR2## wherein X has the same meaning as in formula I,Y' has the same meaning as Y in formula I (F, CF.sub.3), and additionally can be Cl andZ=Cl, mesylate [=OSO.sub.2 CH.sub.3 ] or tosylate=[OSO.sub.2 C.sub.4 H.sub.6 --CH.sub.3 (p)],with alkali metal fluorides and/or with ammonium fluoride. The reaction products I, among which those wherein at least one of both radicals X and Y is CF.sub.3 are novel compounds, are solvents for highly fluorinated compounds and intermediates in various application fields.
    Type: Grant
    Filed: January 14, 1981
    Date of Patent: August 10, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Muffler, Gunter Siegemund, Werner Schwertfeger
  • Patent number: 4331820
    Abstract: A novel compound cis-6-undecene-1-chloride is prepared by reacting cis-3-octene-1-chloride with metallic magnesium to give a Grignard reagent of the chloride and then reacting the Grignard reagent with 1-bromo-3-chloropropane in the presence of a lithium copper chloride as a catalyst. The inventive compound is a useful intermediate compound for the synthetic preparation of several kinds of so-called sexual pheromone compounds of noxious insects. As an example of such sexual pheromone compounds, the synthetic preparation of cis-9-tetradecenyl acetate is described.
    Type: Grant
    Filed: January 7, 1981
    Date of Patent: May 25, 1982
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Kenichi Taguchi, Akira Yamamoto, Toshinobu Ishihara, Nobuo Takasaka, Hisashi Shimizu
  • Patent number: 4329483
    Abstract: A method for preparing cyclotetrasiloxane, aliphatic chlorides and/or acyl chlorides from a chlorosilane and an acyloxy compound is disclosed. The chlorosilane and the acyloxy compound may be present as substantially equimolar amounts of separate compounds or they may be present in the same molecule in equimolar amounts. The reactants are merely heated sufficiently, with or without a soluble halide salt catalyst, to form the products. Advantageously this method can provide cyclotetrasiloxanes having water-sensitive radicals such as silicon-bonded chlorine atoms and/or silicon-bonded acyl chloride radicals.
    Type: Grant
    Filed: July 10, 1981
    Date of Patent: May 11, 1982
    Assignee: Dow Corning Corporation
    Inventor: John L. Speier
  • Patent number: 4329482
    Abstract: A method for preparing cyclotetrasiloxane, aliphatic chlorides and/or acyl chlorides from a cyclotrisiloxane, a chlorosilane and an acyloxy compound is disclosed. The chlorosilane and the acyloxy compound may be present as substantially equimolar amounts of separate compounds or they may be present in the same molecule in equimolar amounts. The reactants are merely heated sufficiently, with or without a soluble halide salt catalyst, to form the products. Advantageously this method can provide cyclotetrasiloxanes having water-sensitive radicals such as silicon-bonded chlorine atoms and/or silicon-bonded acyl chloride radicals. This method also provides a method for preparing cyclotetrasiloxanes having either one type of siloxane unit (non-mixed cyclotetrasiloxanes) or more than one type of siloxane unit (mixed cyclotetrasiloxanes).
    Type: Grant
    Filed: July 10, 1981
    Date of Patent: May 11, 1982
    Assignee: Dow Corning Corporation
    Inventor: Maher Y. A. I. Elsheikh
  • Patent number: 4324931
    Abstract: The invention provides a novel class of organic compounds 1-halo-4-decene as a useful intermediate for the synthesis of cis-6-heneicosen-11-one which is a promising exterminating chemical of the noxious insect Douglas-fir tussock moth in North American forests acting as a sexual pheromone. The synthetic procedures for the synthetic preparation of the above 1-halo-4-decene are also described.
    Type: Grant
    Filed: November 14, 1980
    Date of Patent: April 13, 1982
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshinobu Ishihara, Kenichi Taguchi, Akira Yamamoto, Nobuo Takasaka, Hisashi Shimizu, Mitsuyoshi Oshima
  • Patent number: 4296264
    Abstract: Novel halo substituted ethynylbenzene compounds that are useful in the treatment of inflammation.
    Type: Grant
    Filed: October 19, 1977
    Date of Patent: October 20, 1981
    Assignee: William H. Rorer, Inc.
    Inventor: Julius Diamond
  • Patent number: 4292454
    Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.
    Type: Grant
    Filed: March 18, 1980
    Date of Patent: September 29, 1981
    Assignee: SCM Corporation
    Inventors: Carlos G. Cardenas, Zia Ud Din
  • Patent number: 4264518
    Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the San Jose scale, Quadraspidiotus perniciosus.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: April 28, 1981
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4254039
    Abstract: This invention relates to a process for preparing tetrahydrofuran which comprises reacting a cis-1,4-dihalobutene-2 with water in the presence of a catalytically effective amount of strong acid to provide 2,5-dihydrofuran and thereafter hydrogenating said 2,5-dihydrofuran.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: March 3, 1981
    Assignee: National Distillers & Chemical Corp.
    Inventors: Jawad H. Murib, John M. Inskeep