Alicyclic Unsaturated Or Acyclic Unsaturated Hydrocarbon Reactant Patents (Class 568/317)
  • Patent number: 9745240
    Abstract: The patent discloses a novel metal free process for the preparation of corresponding phenol and ketone via allylic oxidation of substituted cyclohexenes. Air is used as oxidant in the present process and can be used as such or optionally selected from pure oxygen or atmospheric oxygen. Moreover, the process of the present invention utilizes easily available starting materials and is a green eco-friendly, convenient and economical process with high yield of >60% and high selectivity.
    Type: Grant
    Filed: July 28, 2014
    Date of Patent: August 29, 2017
    Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH
    Inventors: Subhash Prataprao Chavan, Pradeep Bhaskarrao Lasonkar
  • Patent number: 8735632
    Abstract: The invention relates to novel polyglycerol based UV-filters as well as to topical compositions comprising such novel polyglycerol based UV-filters. Furthermore, the invention relates to the use of such novel polyglycerol based UV-filters to enhance the solubility of butyl methoxydibenzoylmethane or bis-ethylhexyloxyphenol methoxyphenyl triazine in cosmetic oils.
    Type: Grant
    Filed: December 8, 2010
    Date of Patent: May 27, 2014
    Assignee: DSM IP Assets B.V.
    Inventor: Alexander Schlifke-Poschalko
  • Patent number: 8716531
    Abstract: A method for producing a norbornene derivative includes forming a Mannich base represented by any of general formulae (5) to (7) by reacting a carbonyl compound represented by any of general formulae (1) to (3) and an amine compound represented by general formula (4) with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent, wherein the acidic solvent comprises a formaldehyde derivative and 0.01 mol/L or more of an acid represented by formula HX; reacting the Mannich base and a diene compound represented by general formula (8) with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form the norbornene derivative represented by any of general formulae (9) to (11).
    Type: Grant
    Filed: May 13, 2010
    Date of Patent: May 6, 2014
    Assignee: JX Nippon Oil & Energy Corporation
    Inventors: Shinichi Komatsu, Hisashi Sone, Takeshi Koike, Sayako Kawahama
  • Publication number: 20130096348
    Abstract: The present invention proposes a chiral diene ligand, a fabrication method thereof and applications thereof. The chiral diene ligand is a bicyclo[2.2.1] diene ligand having structural specificity and high stability, which favors the bicyclo[2.2.1] diene ligand to take part in asymmetric transformations, particularly an asymmetric addition reaction involving a metal catalyst in a basic environment. Most of the products of the reactions implemented by the chiral diene ligands of the present invention have superior optical activity. The method of the present invention comprises a first oxidation step, a saponification step, a second oxidation step, a deprotonation step, and a cross-coupling step. The chiral diene ligand of the present invention is very suitable to be used in the fabrication or synthesis of various chemicals and medical products.
    Type: Application
    Filed: September 10, 2012
    Publication date: April 18, 2013
    Inventors: Hsyueh-Liang WU, Chun-Chih Chen, Chia-Chen Liu, Wei-Ting Wei, Jo-Hsuan Fang
  • Patent number: 8350089
    Abstract: The present invention discloses a process for the production of 2-methyl-1,4-naphthoquinone and its bisulfite adducts, comprising the following steps: a) oxidizing 2-methyl-naphthalene (2-MNA) to achieve an organic phase containing 2-methyl-naphthoquinone (2-MNQ) and 6-methyl-naphthoquinone (6-MNQ); b) subjecting said organic phase to treatment with an aqueous solution of a bisulfite salt to extract preferentially the 6-MNQ isomer from the organic phase; c) separating said organic phase from the aqueous phase; d) subjecting the organic phase of process step c) to a second bisulfidation step with an aqueous solution of a bisulfite salt, resulting in an organic phase containing 2-MNA and trace amounts of 2-MNQ and an aqueous phase containing 2-MSB and trace amounts of 6-MSB; e) optionally removing interfering bisulfite ions from the aqueous phase of process step c); f) raising the pH of the aqueous phase from step c) or e) to higher than 8.
    Type: Grant
    Filed: January 11, 2011
    Date of Patent: January 8, 2013
    Assignee: Lonza Ltd.
    Inventors: Kamyab Amouzegar, Behzad Mahdavi, Charles Didier, Alexander Lieb, Mathieu Langevin
  • Publication number: 20120108851
    Abstract: A method for producing a norbornene derivative includes forming a Mannich base represented by any of general formulae (5) to (7) by reacting a carbonyl compound represented by any of general formulae (1) to (3) and an amine compound represented by general formula (4) with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent, wherein the acidic solvent comprises a formaldehyde derivative and 0.01 mol/L or more of an acid represented by formula HX; reacting the Mannich base and a diene compound represented by general formula (8) with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form the norbornene derivative represented by any of general formulae (9) to (11).
    Type: Application
    Filed: May 13, 2010
    Publication date: May 3, 2012
    Applicant: JX NIPPON OIL & ENERGY CORPORATION
    Inventors: Shinichi Komatsu, Hisashi Sone, Takeshi Koike, Sayako Kawahama
  • Publication number: 20100004467
    Abstract: The present application discloses methods for the production of organic compounds comprising a linear series of five fused carbon rings. Such compounds are useful in the production of electronic components, devices and materials. For example the methods disclosed permit the production of 2,9- and 2,10-disubstituted pentacene compounds and 2,6,9,13- and 2,6,10,13-tetrasubstituted compounds that present particularly advantageous properties for the manufacture of semiconductor materials, and may be used in devices such as for example thin film transistors and solar cells. These features are enhanced by ?-? parallel stacking in the solid state. Also disclosed are compounds that are excellent candidates for use in the manufacture of semiconductor materials, and other components of electronic systems, by virtue of their solubility, crystal packing geometries, and electronic properties.
    Type: Application
    Filed: August 6, 2009
    Publication date: January 7, 2010
    Inventor: Alexander Graham FALLIS
  • Patent number: 7235698
    Abstract: Compounds containing a substituted or unsubstituted allyl group directly bound to a chiral carbon atom are prepared enantioselectively. Starting reactants are either chiral or achiral, and may or may not contain an attached allyloxycarbonyl group as a substituent. Chiral ligands are employed, along with transition metal catalysts. The methods of the invention are effective in providing enantioconvergent allylation of chiral molecules.
    Type: Grant
    Filed: August 29, 2005
    Date of Patent: June 26, 2007
    Assignee: California Institute of Technology
    Inventors: Douglas C. Behenna, Brian M. Stoltz, Justin T. Mohr, Andrew M. Harned
  • Patent number: 7067702
    Abstract: A process for preparing vinyl substituted beta-diketones includes reacting a halogen-containing beta-diketone with an olefin in a reaction zone under Heck coupling reaction conditions in the presence of a catalyst, a base, and an organic phosphine to provide a vinyl substituted beta-diketone product.
    Type: Grant
    Filed: May 12, 2005
    Date of Patent: June 27, 2006
    Assignee: The Johns Hopkins University
    Inventors: Glen E. Southard, George M. Murray
  • Patent number: 6881865
    Abstract: Disclosed is a synthesis method of cyclohexyl phenyl ketone with a high selectivity and a high yield from 1,3-butadiene and acrylic acid in the presence or absence of benzene or a non-aromatic organic solvent in the same reaction without a step of separating or purifying intermediates, the synthesis method including sequentially carrying out a [2+4] Diels-Alder reaction, a hydrogenation reaction, a chlorination reaction and a Friedel-Crafts reaction in the presence/absence of benzene or a non-aromatic organic solvent without separation of intermediates.
    Type: Grant
    Filed: July 28, 2003
    Date of Patent: April 19, 2005
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young J. Joo, Jin Eok Kim, Jeong Im Won, Tae Yi Kang
  • Patent number: 6787671
    Abstract: An osmium-assisted process for the oxidative cleavage of oxidizable organic compounds such as unsaturated organic compounds, including alkenes and olefins into aldehydes, carboxylic acids, esters, or ketones. The process uses a metal catalyst comprising osmium and a peroxy compound selected from the group consisting of peroxymonosulfuric acid and salts thereof to oxidatively cleave the oxidizable organic compound. In particular, the process enables aldehydes, carboxylic acids, esters, or ketones to be selectively produced from the corresponding mono-, 1,1-di-, 1,2-di-, tri-, or tetra-substituted olefins in a reaction that produces the result of ozonolysis but with fewer problems. The present invention further provides a process for oxidizing an aldehyde alone or with the osmium in an interactive solvent to produce an ester or carboxylic acid.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: September 7, 2004
    Assignee: Board of Trustees of Michigan State University
    Inventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
  • Patent number: 6770787
    Abstract: The present invention relates to heavier halogen atom substituted squaraine based dyes of the formula 1 below where X is a heavier halogen atom and pharmaceutically acceptable derivatives thereof, which can be used in photodynamic therapeutical and industrial applications, and to a process for the preparation thereof.
    Type: Grant
    Filed: January 2, 2001
    Date of Patent: August 3, 2004
    Inventors: Ramaiah Danaboyina, Arun Kalliat Thazhathveetil, Suresh Das, Bernd Epe
  • Patent number: 6703528
    Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: March 9, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
  • Patent number: 6384251
    Abstract: A procedure for oxidizing organic compounds having allylic hydrogen atom(s) involving the steps of reactively contacting the organic compound with a combination of an N-hydroxy dicarboxylic acid imide and a chromium-containing oxidant. The reaction can conveniently be conducted under ambient temperature and pressure conditions, and is conveniently conducted in a co-solvent system of water and organic solvent(s).
    Type: Grant
    Filed: November 8, 1999
    Date of Patent: May 7, 2002
    Assignee: Humanetics Corporation
    Inventors: Padma Marwah, Henry A. Lardy
  • Patent number: 6355815
    Abstract: A cyclic anthraquinone process for producing hydrogen peroxide using at least two differently substituted 2-alkylanthraquinones and/or their tetrahydro derivatives. The working solution to be used contains (i) at least one reaction carrier from the series 2-(4-methyl-3-pentenyl) anthraquinone (IHEAQ), 2-(4-methylpentyl) anthraquinone (IHAQ) and their di- and tetrahydro derivatives such as, in particular 2-(4-methylpentyl)-&bgr;-tetrahydroanthraquinone (THIHAQ), and (ii) at least one reaction carrier from the series of the 2-(C1- to C5)-alkylanthraquinones, especially 2-ethylanthraquinone (EAQ), and their tetrahydro derivatives. The reaction carriers according to (i) make up 5 to 95 molar %, especially 20 to 50 molar % of all reaction carrier. The method is distinguished by greater H2O2 capacity, improved hydrogenation kinetics and lesser susceptibility to disturbances. A method for making THIHAQ is also disclosed.
    Type: Grant
    Filed: July 27, 2000
    Date of Patent: March 12, 2002
    Assignee: Degussa AG
    Inventors: Jürgen Glenneberg, Gustaf Goor, Eugen Staab, Hubert Angert
  • Patent number: 6353139
    Abstract: A method for preparing ketones has advantages of improving yields and reducing the time of the reactions due to high efficiency of catalysts. Ketones are prepared by reacting an aliphatic or an aromatic aldehyde with a vinyl olefin having an aliphatic or aromatic alkyl moiety in the presence of a transition metal catalyst, 2-aminopyridine catalyst, a primary amine and an acid, as catalysts and additives.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: March 5, 2002
    Inventors: Chul Ho Jun, Dae Yon Lee, Hyuk Lee, Jun Bae Hong
  • Patent number: 6291716
    Abstract: An ortho-alkylation method of an aromatic ketone. In the method, as starting materials, the aromatic ketone is reacted with aliphatic or aromatic alkyl moiety-containing olefins in the presence of a primary amine and a transition metal catalyst as reaction catalysts, or ketimines resulting from a reaction of aromatic ketones with a primary amine are reacted with aliphatic or aromatic alkyl moiety-containing olefins in the presence of a transition metal catalyst, thereby introducing the alkyl moiety to the ortho-position of the aromatic ketone.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: September 18, 2001
    Inventors: Chul Ho Jun, Jun Bae Hong, Kwan Yong Chung, Yeon Hee Kim
  • Patent number: 6258967
    Abstract: A process for the preparation of an aromatic organozinc compound is provided. The process comprises reacting a zinc chloride, bromide or iodide and an organometallic compound of another metal comprising an aromatic moiety, producing a reaction product comprising an organozinc compound and a halide salt of the other metal. The reaction product is then contacted with a liquid hydrocarbon, in which the organozinc compound is soluble and the halide salt of the other metal is of low solubility. The halide salt of the other metal is separated from the hydrocarbon, and the organozinc compound can be recovered from the hydrocarbon. Organozinc compounds produced by this process can be employed to generate chiral centres in suitable substrates.
    Type: Grant
    Filed: June 21, 1999
    Date of Patent: July 10, 2001
    Assignee: Zeneca Limited
    Inventors: Andrew John Blacker, Jan Michael Fielden
  • Patent number: 6252118
    Abstract: A method for preparation of a new ketone from a preexisting ketone is very advantageous in terms of production cost and yield. A reactant mixture consisting of a ketone containing &bgr;-hydrogen relative to the aldehyde group and a vinyl olefin or internal olefin having an aliphatic or aromatic alkyl moiety is allowed to react at approximately 100-180° C. for at least 6 hours in the presence of a rhodium or iridium transition metal catalyst and a 2-aminopyridine derivative.
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: June 26, 2001
    Inventors: Chul Ho Jun, Hyuk Lee
  • Patent number: 6245944
    Abstract: A process for preparing a compound of the formula I where R1 and R2 are hydrogen or C1-C4-alkyl and R3 is C1-C10-alkyl, phenyl or C1-C4-alkyl-substituted phenyl, comprises reacting a compound II with a compound of the formula III where X is chlorine, bromine or iodine, in the presence of a Friedel-Crafts catalyst in one step to give a compound I.
    Type: Grant
    Filed: December 9, 1998
    Date of Patent: June 12, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Carsten Süling, Heike Gregorius, Walter Dobler, Roland Hingmann, Bernhard Rieger, Ulf Dietrich, Jürgen Matthäus Wagner, Hans-Joachim Müller
  • Patent number: 6159988
    Abstract: Compounds of formula I, ##STR1## and the physiologically tolerable salts thereof, wherein the substituents R.sub.1 -R.sub.4 have the meanings given in the specifications and show an activity against inflammatory conditions.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: December 12, 2000
    Assignee: Hoeschst Aktiengesellschaft
    Inventors: Ramachandra Ganapati Naik, Vilas Narayan Mumbaikar, Ravishankar Vasumathy, Aftab Dawoodbhai Lakdawala, Mandakini Bipin Alreja, Bansi Lal, Jurgen Blumbach, Klaus Ulrich Weithmann, Robert Ryder Bartlett, Kalpana Sanjay Joshi, Swati Bal-Tembe, Sadagopan Raghavan
  • Patent number: 6127580
    Abstract: Process for the preparation of anthraquinones of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which can be identical or different, are hydrogen, a C.sub.1 -C.sub.8 -alkyl or C.sub.2 -C.sub.8 -alkenyl radical, in which 1,4-naphthoquinone is reacted with a 1,3-diene of the general formula II ##STR2## in a cycloaddition step to give the corresponding tetrahydroanthraquinone and the tetrahydroanthraquinone is oxidized with oxygen in the presence of a basic catalyst to give the anthraquinone, in which both the cycloaddition step and the oxidation step are carried out in the presence of an aqueous diluent.Preferably, the cycloaddition step and oxidation step are carried out at a reaction temperature between 90 and 110.degree. C. and at atmospheric pressure.
    Type: Grant
    Filed: November 30, 1998
    Date of Patent: October 3, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Siegel, Andreas Kramer
  • Patent number: 6072073
    Abstract: The invention is directed to a process for preparing an alpha-arylated or vinylated carbonyl-containing compounds, comprising reacting a compound having a carbonyl group with an arylating or vinylating compound in the presence of a base and a transition metal catalyst. The transition metal catalyst has the formula X.sub.n M(ER.sub.1-4).sub.m, wherein X is an optional ligand, M is a group 8 transition metal, E is an element bearing a nonbonding electron pair when E is not bonded to the metal, and R is a substituent bonded to E through a carbon, nitrogen, oxygen, or sulfur atom, with the proviso that R.sub.3 cannot contain 3 aryl groups, n is an integer from 0 to 4, and m is an integer from 1-4. The process of the invention is useful for preparation of alpha-arylated or vinylated carbonyl-containing compounds which are significant in the development of pharmacologically active compounds and polymers and oligomers.
    Type: Grant
    Filed: August 18, 1999
    Date of Patent: June 6, 2000
    Assignee: Yale University
    Inventors: Motoi Kawatsura, John F. Hartwig
  • Patent number: 6057456
    Abstract: The present invention is directed to a process for preparing alpha-arylated carbonyl-containing compounds, comprising the steps of reacting a compound having at least one carbonyl group with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an alpha-arylated carbonyl-containing compound, the transition metal catalyst comprising a Group 8 metal and at least one chelating ligand selected from the group consisting of unsaturated Group 15 heterocycles, Group 15-substituted metallocenes, Group 15-substituted alkanes, Group 15-substituted arylenes, and combinations thereof. The process of the present invention simplifies the preparation of commercially significant organic alpha-aryl carbonyl-containing compounds, particularly for use in the pharmaceutical and polymer industries.
    Type: Grant
    Filed: October 15, 1998
    Date of Patent: May 2, 2000
    Assignee: Yale University
    Inventors: John F. Hartwig, Blake C. Hamann
  • Patent number: 6034279
    Abstract: An improved process is described for preparing .gamma.,.delta.-unsaturated ke-tones, which are in demand as aroma substances and intermediates for vitamins and carotenoids, by reacting tertiary allyl alcohols and alkenyl alkyl ethers in the presence of acid catalysts at elevated temperature, which comprises carrying out the reaction in the presence of a phosphorus derivative of the formula IV ##STR1## where A and B are each a branched or unbranched alkyl or alkoxy having from 1 to 10 carbons, a substituted or unsubstituted aryl, cycloalkyl, aryloxy or cycloaryloxy;A can additionally be --H or --OH orA and B together are a substituted or unsubstituted tetramethylene or pentamethylene or substituted or unsubstituted phenyl-1,2-diol or 1,1'-binaphthyl-2,2'-diol.
    Type: Grant
    Filed: January 29, 1999
    Date of Patent: March 7, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Kashammer, Detlef Ruff
  • Patent number: 5770774
    Abstract: A method for preparing 2-methyl-1,4-naphthoquinone (vitamin K.sub.3), in which 2-methyl-1,4-benzoquinone and 1,3-butadienes are subjected to a ?2+4! Diels-Alder reaction and subsequently to oxidative dehydrogenation, using dimethylsulfoxide as both a dehydrogenating agent and a solvent in the presence of at least one Lewis acid or a Broensted acid, in a single pot, shows high selectivity and yield.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: June 23, 1998
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young J. Joo, Jin-Eok Kim, Jeong-Im Won, Kum-Ui Hwang
  • Patent number: 5723678
    Abstract: Acetylenic compounds of the general formula IR.sup.1 --C.tbd.C--CHR.sup.2 --CH.sub.2 --X Iwhere the substituents have the following meanings:R.sup.1 hydrogen, unsubstituted or substituted alkyl or aryl;R.sup.2 hydrogen or C.sub.1 -C.sub.4 -alkyl;X CN; COOR.sup.3 where R.sup.3 is C.sub.1 -C.sub.6 -alkyl or benzyl; C(O)R.sup.4 where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,are prepared by reacting an alkyne of the formula IIR.sup.1 --C.tbd.C--H IIwith an .alpha.,.beta.-unsaturated compound of the formula IIIR.sup.2 HC.dbd.CH--X IIIin the presence of a homogeneous rhodium-phosphine catalyst, in a process wherein a catalyst with a bidentate or tridentate phosphine compound is used.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Peter Hofmann
  • Patent number: 5723675
    Abstract: A method for preparing anthraquinones, by which 1,4-benzoquinone or 1,4-naphthoquinone and 1,3-butadienes are subjected to a ?2+4! Diels-Alder reaction and subsequently to oxidative dehydrogenation by using dimethylsulfoxide as a dehydrogenating agent in a single pot in the presence of a Lewis acid or Broensted acid shows high selectivity and yield.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: March 3, 1998
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young J. Joo, Jin-Eok Kim, Jeong-Im Won, Kum-Ui Hwang
  • Patent number: 5434289
    Abstract: A process for producing an optically active .beta.-hydroxyketone represented by formula (I): ##STR1## by catalytic asymmetrical aldol reaction is disclosed, comprising reacting a silyl-enol ether represented by formula (II): ##STR2## with a substituted aldehyde represented by formula (III):R.sup.5 CHO (III)in the presence of a binaphthol-titanium complex represented by formula (IV): ##STR3## An optically active .beta.-hydroxyketone is efficiently produced with diastereo-specificity and enantio-specificity.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: July 18, 1995
    Assignee: Takasago International Corporation
    Inventors: Koichi Mikami, Satoru Matsukawa, Masaki Shimizu, Masahiro Terada, Noboru Sayo
  • Patent number: 5396011
    Abstract: An aromatic compound (such as benzene) is alkylated with a alkene (such as propylene) by contacting the two compounds together in the presence of a tungsten on zirconia catalyst. The reaction preferably takes place at elevated temperature and elevated pressure. The process of the invention has very high selectivity and conversion, and produces no or only very low amounts of undesirable oligomers (as measured by bromine number).
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: March 7, 1995
    Assignee: Mallinckrodt Chemical, Inc.
    Inventor: Deborah K. Kuhn
  • Patent number: 5393917
    Abstract: A process for isolating and purifying oxadimethacrylics of the general formula ICH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2 Iwhere A and B are selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN and R.sup.1, R.sup.2 and R.sup.3 are each defined as follows:R.sup.1 is hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, substituted or unsubstituted aryl or arylalkyl,R.sup.2 and R.sup.3 are each hydrogen, alkyl, substituted or substituted cycloalkyl or cycloalkylalkyl, substituted or unsubstituted aryl or arylalkyl,comprises precipitating or crystallizing them from their solutions that contain at least one liquid hydrocarbon compound.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: February 28, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegmund Besecke, Andreas Deckers, Harald Lauke
  • Patent number: 5372995
    Abstract: Described is a two-step process for producing phenyl- and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention by means of first reacting methyl ethyl ketone with benzaldehyde in the presence of a sulfonic acid catalyst to produce a mixture of phenyl pentenone derivatives; and then hydrogenating the resulting mixture of phenyl pentenone derivatives in the presence of a hydrogenation catalyst, as well as the product produced thereby; and perfumery uses thereof for augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: December 13, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna
  • Patent number: 4973756
    Abstract: An alpha-hydroxyl-alpha,alpha-di(inert-substituted)-gamma',delta'-yne ketone can be prepared by a procedure comprising contacting an acetylenic Grignard reagent with an alpha-hydroxyl-alpha,alpha-di(inert substituted)-alpha',beta'-ene ketone, and the alpha-hydroxyl-alpha,alpha-di(inert-substituted)-alpha',beta'-ene ketone can be prepared by a procedure comprising steps of contacting, first, an alkoxy allene with a lithium donating organic agent, second, product of the first step with a di(inert-substituted)ketone, and third, product of the second step with an acidic substance.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: November 27, 1990
    Assignee: Marion Laboratories, Inc.
    Inventors: Hans Wynberg, Wolter T. Hoeve, Gerrit A. Barf, Johannes N. Koek, David R. Borcherding
  • Patent number: 4568782
    Abstract: Disclosed is the vapor phase cyclodehydration of an aldehyde or ketone over a solid Lewis acid as catalyst to make indene or a substituted indene according to the equation: ##STR1##
    Type: Grant
    Filed: June 17, 1985
    Date of Patent: February 4, 1986
    Assignee: The Standard Oil Company
    Inventors: Marco Pagnotta, Mark C. Cesa, James D. Burrington
  • Patent number: 4328363
    Abstract: Halogen-substituted olefin addition compounds that contain a carbonyl group are formed by oxidatively adducting an olefin and a carbonyl compound such as a ketone, aldehyde, or ester. The method consists of reacting the olefin and the carbonyl component, in solution, with an oxidizing ion of manganese, cerium or vanadium in the presence of fluoride, chloride or bromide ion. This ionic component is incorporated in the adduct and appears on the olefin-derived carbon atom gamma to the carbonyl group. The gamma halogen substituted adducts are readily converted to cyclopropane derivatives, including pyrethroid intermediate compounds.
    Type: Grant
    Filed: November 8, 1978
    Date of Patent: May 4, 1982
    Assignee: Mobil Oil Corporation
    Inventors: El-Ahmadi I. Heiba, Ralph M. Dessau
  • Patent number: 4263212
    Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: April 21, 1981
    Assignee: Rikagaku Kenkyusho
    Inventors: Pangbu Hong, Hiroshi Yamazaki
  • Patent number: 4260750
    Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.
    Type: Grant
    Filed: March 13, 1980
    Date of Patent: April 7, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Emile Kuntz
  • Patent number: 4241206
    Abstract: The invention is a generalized hydroacylation reaction. The reaction involves the activation of a selected aldehyde by converting by iminization to an aldimine or an aminal. The imine group replaces the carbonyl group. The imine C-H bond is then susceptible to attack by a chosen olefin, and hydrolysis to yield the ketone. One moiety of the ketone derives from the aldehyde and the other from the olefin added later. Therefore, the ketone may be symmetrical or unsymmetrical. Both aromatic and aliphatic aldehydes may be activated according to this process.
    Type: Grant
    Filed: October 27, 1978
    Date of Patent: December 23, 1980
    Assignee: Bell Telephone Laboratories, Incorporated
    Inventor: John W. Suggs