Carbon To Carbon Unsaturation Containing Patents (Class 568/849)
  • Patent number: 11643379
    Abstract: A method includes: providing a mixture including at least one alkyl tosylate and a Grignard reagent; and reacting the at least one alkyl tosylate with the Grignard reagent in a C—C coupling reaction mechanism to form a branched aliphatic alcohol.
    Type: Grant
    Filed: March 23, 2021
    Date of Patent: May 9, 2023
    Assignee: CORNING INCORPORATED
    Inventors: Mingqian He, Yang Li, Jing Sun, Hongxiang Wang, Mong-dong Zhou
  • Patent number: 8618330
    Abstract: A hexafluorodimethylcarbinol terminated compound, method of making it, and a composition of matter are disclosed. The compound may have the formula (CF3)2C(OH)-L-M-R. The substructure L may be selected from an optionally substituted propenylene group (—CH2CH?CH—) and trimethylene group (—CH2CH2CH2—). The substructure M may be selected from a substituted or unsubstituted methylene chain, a substituted or unsubstituted oxyalkylene chain, and a silicon-containing chain or combination thereof. In one embodiment, M may be selected from —(CH2)n—, —(OCH2CH2)m—, and —(Si(CH3)2O)p—Si(CH3)2—(CH2)q—, wherein n is at least 1, e.g., n is up to 10, m can be at least 1, e.g., m is up to 10, p can be 0 and in one embodiment is from 1 to 10, and wherein q can be 1 and in one embodiment is from 1 to 12. The substructure R represents one of a halogen, —SH, —SZ, —S—S-M-L-C(CF3)2(OH), wherein Z represents a thiol protecting group.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: December 31, 2013
    Assignee: The United States of America, as represented by the Secretary of the Navy
    Inventor: Arthur W Snow
  • Publication number: 20120142935
    Abstract: This invention provides a method for preparing a 1,2,3-triazole compound comprising contacting an organic azide with a 2-substituted-1-haloalkyne, in the presence of a copper catalyst and a copper-coordinating ligand (preferably a tertiary amine) in a liquid reaction medium, thereby forming a 1,4,5-substituted-1,2,3-triazole compound including a halo substituent at the 5-position of the triazole, the organic portion of the organic azide at the 1-position of the triazole, and the substituent of the 1-iodoalkyne at the 4-position of the triazole. A method for preparing 1-iodoalkynes is also provided.
    Type: Application
    Filed: August 11, 2010
    Publication date: June 7, 2012
    Inventors: Jason E. Hein, Jonathan C. Tripp, Larissa Krasnova, K.Barry Sharpless, Valery V. Fokin
  • Publication number: 20100311989
    Abstract: Disclosed is a process for the preparation of tetrahydropyran-di-amine represented by Structural Formula (I): wherein R1 is H or alkyl and E is H or an amine protecting group.
    Type: Application
    Filed: September 17, 2008
    Publication date: December 9, 2010
    Inventors: Marlys Hammond, Patrick Stoy, Scott K. Thompson
  • Publication number: 20090005609
    Abstract: Methods and systems for the preparation of chlorohydrins are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of olefins into the chlorinating phase. The high shear device may allow for lower reaction temperatures and pressures and may also reduce chlorination time.
    Type: Application
    Filed: June 20, 2008
    Publication date: January 1, 2009
    Applicant: H R D CORPORATION
    Inventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
  • Publication number: 20080293897
    Abstract: Adducts are provided comprising MgCl2, ethanol and a Lewis base (LB), said compounds being present in molar ratios defined by the following formula MgCl2.(EtOH)n(LB)p in which n is from 2 to 6 and p has values satisfying the following equation p/(n+p)?0.1. The said adducts can be used as precursor in the preparation of high activity ZN catalysts.
    Type: Application
    Filed: November 24, 2004
    Publication date: November 27, 2008
    Applicant: Basell Poliolefine Italia s.r.l.
    Inventors: Gianni Collina, Daniele Evangelisti, Mario Sacchetti
  • Publication number: 20080200733
    Abstract: The present invention relates to processes for the preparation of purified solanesol, solanesyl bromide & solanesyl acetone. Solanesyl acetone has the chemical name—all—trans 6,10,14,18,22,26,30,34,38-nonamethyl-5,9,13,17,21,25,29,33,37-triacontanonaen-2-one, of formula 1 and is used for synthesis of coenzyme Q10.
    Type: Application
    Filed: June 21, 2006
    Publication date: August 21, 2008
    Applicant: NICHOLAS PIRAMAL INDIA LIMITED
    Inventors: Abhay Upare, Ganesh Wagh, Amit Chavan, Wazid Sajjad Jafri, Sabapathi Selvakumar, Mita Roy
  • Patent number: 7045642
    Abstract: A process for labeling organic compounds with deuterium and tritium is described using specific catalysts.
    Type: Grant
    Filed: May 25, 2004
    Date of Patent: May 16, 2006
    Assignee: The Regents of the University of California
    Inventors: Robert C. Bergman, Steven R. Klei
  • Patent number: 6169212
    Abstract: The compounds of formula wherein the acetyl substituting group is either in position 2 or in position 3 of the cycle, or any mixture of compounds of formula (I) are novel compounds which can namely confer a natural odor of the leather type to products or compositions to which they are added.
    Type: Grant
    Filed: October 22, 1999
    Date of Patent: January 2, 2001
    Assignee: Firmenich SA
    Inventor: Wolfgang Klaus Giersch
  • Patent number: 5919992
    Abstract: The present invention relates to process of halogenating an alkynol having 3 to 20 carbon atoms to produce a compound having the formula: R-C.tbd.(C--CH.sub.2).sbsb.x-OH, wherein R is F, Cl, Br or I and x is 1 to 18. In particular, this invention provides a process for preparing a halopropynyl alcohol, specifically iodopropynyl alcohol. In one embodiment, iodopropynyl alcohol is produced by sequentially adding potassium hydroxide, potassium iodide and an oxidizing agent to a solution of propynyl alcohol at a rate and temperature sufficient to produce an iodopropynyl alcohol.
    Type: Grant
    Filed: June 11, 1996
    Date of Patent: July 6, 1999
    Assignee: Lonza, Inc.
    Inventor: David L. Kuo
  • Patent number: 5728376
    Abstract: The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: March 17, 1998
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Athula B. Attygalle, Gulab N. Jham, Ales Svatos, Rosa T.S. Frighetto
  • Patent number: 5654473
    Abstract: Novel trifluoromethylated intermediates are provided which are useful in synthesizing trifluoromethylated organic compounds. Specifically, compounds of the formula CF.sub.3 CCl.dbd.CHCH.sub.2 X are provided, which compounds are versatile intermediates for the synthesis of a wide variety of trifluoromethylated organic compounds.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: August 5, 1997
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5406007
    Abstract: Disclosed is a process for the conversion of conjugated epoxyalkenes to unsaturated alcohols wherein a conjugated epoxyalkene is catalytically hydrogenated in the presence of a sulfur-modified or sulfided nickel catalyst whereby the epoxide ring is hydrogenolyzed without concomitant hydrogenation of the olefinic unsaturation thereby producing allylic and/or homoallylic alcohols.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: April 11, 1995
    Assignee: Eastman Chemical Company
    Inventor: Stephen N. Falling
  • Patent number: 5349097
    Abstract: A process for the catalytic isomerization of secondary .alpha.-alkenols of formula I ##STR1## in which R.sup.1 is a C.sub.1 -C.sub.20 alkyl group or a C.sub.2 -C.sub.2 alkenyl group and in which R.sup.2 stands for hydrogen, a halogen atom, a C.sub.1 -C.sub.10 alkoxy group, a carbonyl group, or a C.sub.1 -C.sub.20 alkyl group and in which R.sup.1 and R.sup.2 can be joined together to complete a five-membered or six-membered carbocyclic ring, to primary .alpha.-alkenols of formula II ##STR2## or for the isomerization of primary .alpha.-alkenols of formula II to secondary .alpha.-alkenols of formula I, wherein the isomerization is carried out in the presence of organotrioxorhenium(VII) compounds of formula III ##STR3## in which R.sup.3 is a C.sub.1 -C.sub.10 alkyl group, a cyclopentadienyl group substituted by from one to five C.sub.1 -C.sub.4 alkyl groups, an unsubstituted cyclopentadienyl group, a C.sub.6 -C.sub.10 aryl group, or a C.sub.7 -C.sub.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: September 20, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Thome, Michael Roeper, Heinz-Josef Kneuper
  • Patent number: 5149843
    Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5087774
    Abstract: A novel process for converting myrcene to a key palladium-myrcene complex using palladium (II) chloride in the presence of an aqueous cycloamide solvent and lithium salt is disclosed. Novel processes for converting the palladium-myrcene complex to citral using a phosphine compound, or to nerol using a nitrogen-donor compound in the presence of hydrogen gas, are also presented.
    Type: Grant
    Filed: July 10, 1990
    Date of Patent: February 11, 1992
    Assignee: Union Camp Corporation
    Inventor: James B. Woell
  • Patent number: 5049681
    Abstract: A novel optically active allyl alcohol derivative represented by the following general formulae (I), (II), (III) and (IV): ##STR1## The novel optically active allyl alcohol can be used effectively for producing leucotrienes B.sub.4 by the process of reacting an optically active halogen substituted allyl alcohol and a novel optically active acetylene-substituted allyl alcohol.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: September 17, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4985594
    Abstract: Process for the preparation of fluorinated carboxylic acid fluoridesFluorinated carboxylic acid fluorides of the Formula I ##STR1## can be prepared from fluorinated vinyl ethers of the Formula II ##STR2## by heating the vinyl ethers to a temperature of 100.degree. to 350.degree. C.Perfluorinated carboxylic acids and derivatives thereof can be prepared from the carboxylic acid fluorides by secondary reactions, for example hydrolysis, esterification or aminolysis.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: January 15, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Blickle, Klaus Hintzer, Werner Schwertfeger, Heinz Strutz
  • Patent number: 4933511
    Abstract: An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II ##STR1## wherein: X.sup.1, X.sup.2 and X.sup.3 independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C.sub.1 to C.sub.6 alkyl, C.sub.1 and C.sub.6 haloalkyl, and haloaryl; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R.sup.3 and R.sup.4 is as hereinbefore defined and R.sup.1 and R.sup.2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene or formula IV in the presence of an optically-active organometallic catalyst. ##STR2## Furthermore, the compound of formula II can be isomerized to the allylic alcohol of formula I with retention of optical purity.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: June 12, 1990
    Assignee: ICI Australia Limited
    Inventors: Matthew Gredley, Colin Wilshire
  • Patent number: 4730065
    Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.
    Type: Grant
    Filed: July 24, 1987
    Date of Patent: March 8, 1988
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
  • Patent number: 4720591
    Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: January 19, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
  • Patent number: 4644085
    Abstract: 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: Grant
    Filed: June 4, 1985
    Date of Patent: February 17, 1987
    Assignee: Rooperol (NA) NV
    Inventors: Siegfried Drewes, Roelof W. Liebenberg
  • Patent number: 4634778
    Abstract: Process for preparing chlorinated ethylenic derivatives of the formula ##STR1## in which R.sub.1 represents acetyl, formyl optionally in the form of an acetal, hydroxy optionally as an ether or ester, alkyloxycarbonyl, alkyl of 1 to 12 carbon atoms substituted by one or more acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, alkenyl of 2 to 12 carbon atoms containing one or more double bonds optionally substituted by one or more of acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, or R.sub.1 represents 3-sulpholenyl or a radical of formula ##STR2## in which R.sub.2 denotes a hydrogen or acetyl, by reacting chlorine in a nonpolar aprotic solvent with a compound of general formula ##STR3## in which R.sub.1 is defined as above. The products of formula I, some of which are new, are useful as intermediates in the synthesis of terpene products such as vitamin E.
    Type: Grant
    Filed: November 16, 1984
    Date of Patent: January 6, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel, Pierre Chabardes
  • Patent number: 4578396
    Abstract: Hydroxyalkinyl-azolyl derivatives of the formula ##STR1## in which A is a nitrogen atom or the CH group,R is optionally substituted alkyl, cycloalkyl or phenyl,R.sup.1 is hydrogen, alkyl, alkenyl, alkinyl, or optionally substituted benzyl,R.sup.2 is hydrogen or methyl, andX is hydrogen, bromine or iodine,or addition products thereof with acids or metal salts exhibit fungicidal activity. Some intermediates therefor are also new.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: March 25, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Klaus Bockmann, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger, Hans Scheinpflug
  • Patent number: 4536347
    Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: August 20, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang
  • Patent number: 4385185
    Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: May 24, 1983
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Walter Hafner
  • Patent number: 4380675
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are equal or different aliphatic radicals, if desired, branched, and R.sub.3 stands for H or CH.sub.3. The invention also relates to a process for making these compounds and their use as fragrant and flavoring products.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: April 19, 1983
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Walter Hafner
  • Patent number: 4345084
    Abstract: Unsaturated eicosanoic acids and derivatives thereof which inhibit the synthesis of SRS-A are useful for treating and preventing asthma and allergic responses caused by SRS-A as well as useful in inhibiting inflammation.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: August 17, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, George W. Holland, Perry Rosen
  • Patent number: 4310709
    Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventor: Walter Rebafka
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4197245
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: April 8, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4172839
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 30, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4170597
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 9, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4113968
    Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.
    Type: Grant
    Filed: September 26, 1975
    Date of Patent: September 12, 1978
    Assignee: Kuraray Co., Ltd.
    Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi