Preparing Esters From Halogenated Hydrocarbons Patents (Class 560/236)
  • Patent number: 10221123
    Abstract: A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.
    Type: Grant
    Filed: July 30, 2018
    Date of Patent: March 5, 2019
    Inventors: Yuki Miyake, Takeshi Kinsho, Yusuke Nagae
  • Publication number: 20140309452
    Abstract: Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ?-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).
    Type: Application
    Filed: April 9, 2014
    Publication date: October 16, 2014
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Miyoshi Yamashita, Takehiko Fukumoto, Takeshi Kinsho
  • Publication number: 20100298595
    Abstract: There is provided a method for separating and collecting at least alcohol with a high purity from an azeotropic mixture of olefin and alcohol.
    Type: Application
    Filed: January 9, 2009
    Publication date: November 25, 2010
    Inventors: Yuuki Matsuda, Kazuyoshi Ichihara, Takeomi Hirasaka, Takuya Ichida
  • Patent number: 7674925
    Abstract: Methods of producing plant polyols from plant oils include reacting a plant oil with a designed reactant having one or more nucleophilic functional groups and one or more active hydrogen functional groups in the presence of an addition reaction catalyst in a single reaction step. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.
    Type: Grant
    Filed: September 21, 2006
    Date of Patent: March 9, 2010
    Assignee: Athletic Polymer Systems, Inc.
    Inventors: Thomas M. Garrett, Xian Xia Du
  • Patent number: 6946566
    Abstract: A process for preparing regioselectively an optically active 1-halogeno-2-hydroxypropyl compound of the following formula; wherein X is halogen atom and Nu is a heteroatom having a substituent, and an optically active glycidyl compound of the formula; which comprises reacting an optically active epihalohydrin of the formula; with a neucleophilic agent, in the presence of a metal complex of the formula; wherein n is an integer of 0, 1 or 2, Y1, Y2 and Y3 are hydrogen atom, etc., and Y2 and Y3 may form a ring such as benzene, A is a counterion and M is a metal ion, and further subjecting the compound (4) to reaction with a base to prepare the optically active glycidyl compound (5).
    Type: Grant
    Filed: July 30, 2003
    Date of Patent: September 20, 2005
    Assignee: Daiso Co., Ltd.
    Inventors: Keisuke Yaegashi, Yoshiro Furukawa
  • Publication number: 20040077898
    Abstract: There is provided a method for obtaining a high-purity alkyladamantyl ester from an alkyladamantyl ester composition containing a large quantity of alkyladamantyl halide obtained by, for example, alkylating raw material 2-adamantanone obtained through oxidation of adamantane by use of an organic metal reagent and then causing an acid halide to react with the resulting product, efficiently by a simple process.
    Type: Application
    Filed: July 25, 2003
    Publication date: April 22, 2004
    Inventors: Masao Yamaguchi, Hiromasa Yamamoto, Hideki Kikuchi, Yoshihiro Hirota
  • Publication number: 20030233008
    Abstract: Carboxylic benzyl esters can be prepared by reacting benzyl chloride with carboxylic acids in the presence of one or more quaternary ammonium carboxylates as catalyst.
    Type: Application
    Filed: June 10, 2003
    Publication date: December 18, 2003
    Inventors: Pieter Ooms, Ursula Jansen, Bernd-Ulrich Schenke
  • Publication number: 20030130538
    Abstract: An ester compound of formula (1) 1
    Type: Application
    Filed: January 7, 2003
    Publication date: July 10, 2003
    Applicant: Sumitomo Chemical Company, Limited
    Inventors: Noboru Yamamoto, Sanshiro Matsuo
  • Patent number: 6515188
    Abstract: A method for safely and efficiently producing high purity 3-l-menthoxypropane-1,2-diol and intermediates to be used in the method. As shown in the following reaction formula, 3-l-menthoxypropane-1,2-diol represented by the chemical formula (IV) is produced by adding l-menthol to a 1,2-epoxy-3-halogenopropane represented by the general formula (I) (wherein X represents a halogen atom) in an organic solvent in the presence of a Lewis acid, thereby producing a 1-halogeno-3-l-menthoxypropan-2-ol represented by the general formula (II), allowing the first intermediate to react with an alkali metal salt of an aliphatic carboxylic acid having from 1 to 5 carbon atoms to produce a 1-acyloxy-2-substituted-3-l-menthoxypropane represented by the general formula (III) and then hydrolyzing the second intermediate.
    Type: Grant
    Filed: April 4, 2002
    Date of Patent: February 4, 2003
    Assignee: Takasago International Corporation
    Inventors: Akira Amano, Teruyoshi Akiyama, Takashi Miura, Toshimitsu Hagiwara
  • Publication number: 20020177729
    Abstract: The present invention provides a process for preparing a desired halogenated ester, which process comprises the steps of:
    Type: Application
    Filed: April 5, 2002
    Publication date: November 28, 2002
    Applicant: 3M Innovative Properties Company
    Inventors: Klaus Hintzer, Egon Obermaier, Werner Schwertfeger
  • Patent number: 6465696
    Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide only or the alkyl bromide and the hydrogen bromide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide is oxidized to form original metal oxide and bromine, both of which are recycled.
    Type: Grant
    Filed: September 11, 2001
    Date of Patent: October 15, 2002
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Xiao Ping Zhou, Galen D. Stucky, Jeffrey H. Sherman
  • Patent number: 6018075
    Abstract: A process for the manufacture of a .gamma.-acetoxy-tiglic aldehyde by reacting a .gamma.-bromotiglic aldehyde or a .gamma.-chlorotiglic aldehyde with sodium acetate or potassium acetate in an organic solvent in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: January 25, 2000
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
  • Patent number: 5804687
    Abstract: A compound (Ia) or (Ib) is prepared by reacting, in a polar aprotic solvent, a compound (III) with a salt of a carboxylic or dicarboxylic acid (IIa) or (IIb). The reaction may be carried out under pressure, but also at normal atmospheric pressure or in the region of normal atmospheric pressure (especially between 0.10 bar and 2 bars). The product (Ia) or (Ib) formed is, in this latter case, recovered continuously as it is formed. ##STR1## R.sup.1, R.sup.2 =optionally substituted saturated or unsaturated acyclic or cyclic hydrocarbon radicals; R.sup.3 =C.sub.1 -C.sub.10 perhaloalkyl; 0<n.ltoreq.4; X=halogen.The applications of the fluoroalkyl (meth)acrylates obtained are especially: anti-dust or anti-soiling paints for various supports such as exterior coatings and metal furniture; optical fibers; contact lenses; lithography; electrophotography; heat-resistant materials; dental resins.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: September 8, 1998
    Assignee: Elf Atochem S.A.
    Inventors: Gilles Drivon, Jean-Philippe Gillet, Sophie Suc
  • Patent number: 5648489
    Abstract: A method is provided for the synthesis of synthesis of acyclic purine nucleosides, particularly 9-(2-hydroxy-ethoxymethyl)-guanine (acyclovir) and 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine ("DHPG") where the N.sup.2,N.sup.9 -diprotected guanine is reacted with CH.sub.3 C(O)OCH.sub.2 O(CH.sub.2).sub.2)OC(O)CH.sub.3 or 2-acetoxymethoxy-1,3-diacetoxypropane, respectively, in the presence of a mixture of an acid and acetic anhydride, or in the presence of an acid, where the acid can be phosphoric acid or polyphosphoric acid.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 15, 1997
    Assignee: University of Georgia Research Foundation
    Inventors: Chung K. Chu, Jinfa Du, Chunguang Wang
  • Patent number: 5414116
    Abstract: The invention relates to a catalyst formed of an active charcoal support in the form of particles or of cylinders having a diameter from 0.3 to 1.5 mm and a length of 0.3 to 5 mm or spheres having a diameter from 0.3 to 2 mm, the said particles being loaded with a precious metal from group 8. Advantageously, palladium on active charcoal is used.The invention is particularly useful for purifying monochloroacetic acid.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: May 9, 1995
    Assignee: Societe Elf Atochem S.A.
    Inventor: Yves Correia
  • Patent number: 5319132
    Abstract: The present invention provides a process for producing a halomethyl ester of an aliphatic carboxylic acid in which a metal salt of an aliphatic carboxylic acid is reacted with a dihalomethane in the presence of a phase transfer catalyst, whereby the efficient production of a halomethyl ester of an aliphatic carboxylic acid has been made possible without the formation of a halomethyl ether as a by-product. The bis compound bis[aliphatic carbonyloxy)methane], which is obtained as a by-product, is hydrolyzed to enable the quantitative recovery of an aliphatic carboxylic acid and its reuse. Thus, the present process is preferable as a process for industrial production of a halomethyl ester of an aliphatic carboxylic acid.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: June 7, 1994
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Noriyuki Ozawa, Naoto Yazawa
  • Patent number: 5292929
    Abstract: A process for producing (R)-2-hydroxy-6-haloalkane is disclosed. In the first step, a cyclic alkanol is photohalogenated. In the second step, the photohalogenation product is reacted with a chiral catalyst and dialkyl zinc to produce (R)-2-hydroxy-6-haloalkane.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: March 8, 1994
    Assignee: Boulder Scientific Company
    Inventor: Jeffrey M. Sullivan
  • Patent number: 5202462
    Abstract: A process for producing a halomethyl pivalate which comprises reacting an aqueous solution of a metal salt of pivalic acid with a dihalomethane selected from the group consisting of bromochloromethane, chloroiodomethane and bromoiodomethane in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: July 28, 1992
    Date of Patent: April 13, 1993
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Naoto Yazawa, Keinosuke Ishikame
  • Patent number: 5068401
    Abstract: Organic esters such as propylene glycol diacetate are prepared in a single organic reaction phase from the corresponding halocarbon having from 3 to 8 carbon atoms, e.g., 1,2-dicholorpropane and the alkali or alkaline earth metal salt of a carboxylic acid. The inorganic salt formed thereby is not soluble in the organic phase. The reaction rate and selectivity are surprisingly good when the reaction contains little or no water.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: November 26, 1991
    Assignee: The Dow Chemical Company
    Inventors: Garnet E. McConchie, Frank E. Mark, Hans-Gunter Hollmann
  • Patent number: 4990458
    Abstract: A process for forming derivatives of organic compounds as a step during their analysis. A macroreticular resin is used as both an adsorbent for the analyte and the derivatizing reagent and also as a catalyst for the derivatization reaction. Subsequent serial elution of the absorbed compounds leads to simple separation of the derivatized analyte from the starting materials. Further, the resin impregnated with derivatizing reagent can be used to combine the extraction and derivatization of the analyte. As macroreticular resins are relatively inexpensive, they result in reduced costs compared with conventional catalysts, and their ease of separation from liquid systems makes them easy to use and makes it possible to automate the procedure.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: February 5, 1991
    Assignee: McMaster University
    Inventor: Jack M. Rosenfeld
  • Patent number: 4929775
    Abstract: This invention relates to a process for preparing high purity dibromoneopentyl glycol which comprises: (a) charging a vessel with pentaerythritol, a first portion of aqueous HBr and a catalyst; (b) maintaining the liquid contents in the vessel at a temperature from C. to C. for 1 to 3 hours; (c) adding a second portion of aqueous HBr to provide a total HBr to pentaerythritol molar ratio of 1:3 to 1:6; (d) after the foregoing aqueous HBr addition, raising the temperature of the liquid content of the vessel to C. to C.; and (e) sweeping the headspace of the vessel during at least (b), (c) and (d) with an inert gas and removing the sweep gas and any vapors formed during the process from the vessel.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: May 29, 1990
    Assignee: Ethyl Corporation
    Inventor: Saadat Hussain
  • Patent number: 4898970
    Abstract: This invention relates to a process for producing a fluorinated ester containing a trifluoromethyl group by esterification in the presence of .gamma.-butyrolactone as a solvent, and more particularly a process or producing a fluorinated ester containing a trifluoromethyl group which is useful as a raw material of various fluorine containing compound.
    Type: Grant
    Filed: February 1, 1983
    Date of Patent: February 6, 1990
    Assignees: Onoda Cement Co., Ltd., Tosoh Corporation
    Inventors: Eiji Ogura, Kunihiro Mito, Shoji Arai
  • Patent number: 4791223
    Abstract: The invention relates to the synthesis of 1,1,2,2-tetrahydroperfluoroalkanols and their esters by oxidizing a 2-(perfluoroalkyl)ethyl iodide using hydrogen peroxide in a carboxylic acid or carboxylic acid ester in the presence of sulphuric acid.In the process according to the invention, from 1 to 30 moles of sulphuric acid, from 1 to 50 moles of carboxylic acid or of an ester of such an acid, and from 3 to 20 moles of hydrogen peroxide per mole of 2-perfluoralkyl)ethyl iodide are used.
    Type: Grant
    Filed: December 4, 1987
    Date of Patent: December 13, 1988
    Assignee: Societe Atochem
    Inventors: Andre Lantz, Pascal Michaud
  • Patent number: 4720572
    Abstract: A process for the preparation of a 4-acyloxy-3-oxo-butyric acid ester of the formula ##STR1## in which R.sup.1 is alkyl with up to 4 C atoms, andR.sup.2 is alkyl with up to 4 C atoms and optionally substituted by halogen, hydroxyl, alkoxy or phenyl, or is aryl,which comprises reacting a 4-halogenobutyric acid ester of the formula ##STR2## in which X is chlorine or bromine, with a carboxylic acid of the formula ##STR3## in the presence of acid-trapping agent in an organic solvent at a temperature of between and C.
    Type: Grant
    Filed: November 15, 1985
    Date of Patent: January 19, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Mathias Stubbe
  • Patent number: 4699991
    Abstract: Organosilicon compounds referred to as silacrown ethers or "silacrowns" are of the general formula: ##STR1## where R.sup.1 and R.sup.2 are organic radicals or hydrogen and n is an integer between 4 and 10 inclusive. Silacrown ethers are prepared by reacting polyethylene glycol with substituted silanes under conditions promoting cyclization over polymerization. Silacrown ethers may be employed as phase-transfer catalysts in solution or immobilized on siliceous supports.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: October 13, 1987
    Assignee: Petrarch Systems Inc.
    Inventor: Barry C. Arkles
  • Patent number: 4666633
    Abstract: A triarylmethyl methacrylate is produced by reacting methacrylic acid with a triarylmethylating agent in an inert, organic solvent containing therein an excess amount of an amine or in the presence of an anion exchanger.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: May 19, 1987
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoichi Yuki, Ryoji Noyori, Masahiko Hayashi
  • Patent number: 4613681
    Abstract: This invention relates to a process for the preparation of a fluorinated compound of the general formulaR.sub.F C.sub.2 H.sub.4 ORcomprising reacting an iodide of the general formula R.sub.F C.sub.2 H.sub.4 I with a percarboxylic acid of the general formula R.sup.1 CO.sub.3 H at a temperature and for a time sufficient to form said fluorinated compound; in said formulae R.sub.F is a straight or branched chain perfluorinated radical containing 1 to 20 C atoms, R is a hydrogen atom or --COR.sup.1, and R.sup.1 is a hydrogen atom or an aliphatic or aromatic hydrocarbon radical.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: September 23, 1986
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Louis Foulletier, Andre Lantz
  • Patent number: 4609498
    Abstract: Process for the production of the insect sex attractant, gossyplure, is provided. The process comprises first disproportionating 1,5-cyclooctadiene and 1-hexene to give 1,5,9-tetradecatriene, then metallating the triene to form a 1-metallo-5,9-tetradecadiene, and finally treating the organometal compound with a C.sub.2 -synthon to give directly 7,11-hexadecadienyl acetate or a substituted 7,11-hexadecadienyl moiety which can readily be converted to the desired acetate.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: September 2, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Edward C. Mozdzen, Jim D. Byers
  • Patent number: 4478760
    Abstract: The process for making a fluorinated product comprising reacting a perfluoroalkyl iodide and an olefin in the presence of a finely divided zinc and an acidic solvent.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: October 23, 1984
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre
  • Patent number: 4443625
    Abstract: The present invention relates to crop culture and is particularly concerned with practices for conserving soil nitrogen and for supplying the soil nitrogen requirements for plant nutrition. These practices involve the employment, as active agent, of a novel butane compound having the formula ##STR1## wherein X is H or ##STR2## R is H or C.sub.1 -C.sub.8 alkyl; R' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo and n is an integer from 0 to 2.
    Type: Grant
    Filed: May 14, 1981
    Date of Patent: April 17, 1984
    Assignee: The Dow Chemical Co.
    Inventors: Jeffrey D. Griffith, Thomas M. Ozretich
  • Patent number: 4434297
    Abstract: A process for the preparation of 2,2,2-trifluoroethanol which comprises reacting 2-chloro-1,1,1-trifluoroethane with an alkali metal salt of a carboxylic acid in a substantially anhydrous aprotic solvent thereby to form the carboxylic acid ester of 2,2,2-trifluoroethanol and an alkali metal chloride, reacting the ester with the hydroxide or a basic salt of the alkali metal in water thereby to form 2,2,2-trifluoroethanol and the alkali metal salt of the carboxylic acid, separating the 2,2,2-trifluoroethanol, and recycling the alkali metal salt of the carboxylic acid for further reaction. Advantageously the alkali metal salt is potassium acetate, the aprotic solvent is N-methyl-2-pyrrolidone and the reaction in the N-methyl-2-pyrrolidone is effected at about to C.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: February 28, 1984
    Assignee: Halocarbon Products Corporation
    Inventor: Gary W. Astrologes
  • Patent number: 4421675
    Abstract: A novel catalyst, possessing phase transfer properties contains an alumina or silica substrate bearing at least one poly(oxyethylene) or poly(oxypropylene) residue bonded through an oxygen atom to the substrate.
    Type: Grant
    Filed: January 8, 1982
    Date of Patent: December 20, 1983
    Assignee: Texaco Inc.
    Inventor: Robert A. Sawicki
  • Patent number: 4391984
    Abstract: The invention provides a novel method for the synthetic preparation of an .omega.-haloalkyne compound of the general formula R--C.tbd.C--CH.sub.2).sub.n X, in which X is a halogen atom, R is a monovalent hydrocarbon group and n is 4, 5 or 6, by the coupling reaction of a Grignard reagent RMgX' and an .omega.-halo-1-bromoalkyne compound of the formula X--CH.sub.2).sub.n C.tbd.C-Br. The .omega.-haloalkyne compound obtained in the above can be readily converted to the corresponding alkenyl acetate of the formula R--CH.dbd.CH--CH.sub.2).sub.n OCOCH.sub.3 by first acetylating and then partially hydrogenating in the presence of a Lindlar catalyst. In particular, 7, 11-hexadecadienyl acetate, which is a sexual pheromone compound of a noxious insect, is obtained in the same route of synthesis starting with the Grignard reagent of a 1-halo-3-octene and 1, 8-dibromo-1-octyne.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: July 5, 1983
    Assignee: Schin-Etsu Chemical Co., Ltd.
    Inventors: Toshinobu Ishihara, Akira Yamamoto, Kenichi Taguchi
  • Patent number: 4377533
    Abstract: Process for introducing a substituent selected from branched- or straight-chain alkyl radicals having from 1 to 12 carbon atoms, aralkyl or cycloalkyl radicals in which the alkyl moiety has from 1 to 4 carbon atoms, into a carbon chain bearing a stable functional group the said carbon chain having at least one proton in .alpha.-position in relation to this functional group, process whereby, in a first step, this carbon chain is reacted with a complex base comprising a mixture of alkali metal amide and alkali metal alcoholate suspended in an anhydrous organic solvent to provide temporarily a carbanion, then in a second step this carbanion is reacted in an anhydrous organic solvent with an alkyl, aralkyl or cycloalkyl halide corresponding to the substituent to be introduced.
    Type: Grant
    Filed: April 3, 1981
    Date of Patent: March 22, 1983
    Assignee: Sanofi
    Inventors: Michel Bouisset, Michel Chignac, Claude Grain, Charles Pigerol
  • Patent number: 4362884
    Abstract: Organosilicon compounds referred to as silacrown ethers or "silacrowns" are of the general formula: ##STR1## where R.sup.1 and R.sup.2 are organic radicals or hydrogen and n is an integer between 4 and 10 inclusive. Silacrown ethers are prepared by reacting polyethylene glycol with substituted silanes under conditions promoting cyclization over polymerization. Silacrown ethers may be employed as phase-transfer catalysts in solution or immobilized on siliceous supports.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: December 7, 1982
    Assignee: Petrarch Systems, Inc.
    Inventor: Barry C. Arkles
  • Patent number: 4314072
    Abstract: 2-(2-Hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde and certain derivatives thereof are useful intermediates for the preparation of dihalovinyl-type pyrethroid esters.
    Type: Grant
    Filed: November 23, 1979
    Date of Patent: February 2, 1982
    Assignee: Shell Oil Company
    Inventor: Johannes L. M. Syrier
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4233464
    Abstract: 1-[3-Methyl-3,5,5-trialkoxy-pent-1-yn-1-yl]-2,6-dimethyl-cyclohex-1-enes, which may or may not be methyl-substituted in the 2- and/or 6-position, are obtained by reacting the corresponding 1-[3-methyl-but-1-yn-3-en-1-yl]-2,6-dimethyl-cyclohex-1-enes with orthoformic acid esters in the presence of acid condensing agents. The new compounds provide a new method of access to the compounds of carotinoid chemistry, especially to vitamin A, which avoids the conventional expensive synthesis via phosphorus ylide compounds.
    Type: Grant
    Filed: April 12, 1978
    Date of Patent: November 11, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Baumann, Werner Hoffmann
  • Patent number: 4229366
    Abstract: The invention relates to a process for nucleophilic substitution reactions. According to the invention the reaction is carried out in a heterogeneous system, consisting of a solid and a dissolved reactant, one or several organic solvents, one or several linear polyether derivatives, and/or amino compounds and water.The volume of the water is preferably at the most 100% of the volume of the organic solvent and more preferably 5%.According to the invention the anhydrous reaction medium which is difficult to ensure, is not necessary and the use of the expensive and in industrial scales unavailable crown ethers is eliminated.
    Type: Grant
    Filed: October 20, 1978
    Date of Patent: October 21, 1980
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termeker Gyara Rt.
    Inventors: Laszlo Toke, Gabor T. Szabo, Gabor Szabo, Lajos Nagy, Istvan Rusznak
  • Patent number: 4219680
    Abstract: 2-(perfluoroalkyl)-ethanols of the formula R.sub.f CH.sub.2 CH.sub.2 OH are obtained from 2-(perfluoroalkyl)-ethyl iodides of the formula R.sub.f CH.sub.2 CH.sub.2 I as a mixture with 2-(perfluoroalkyl)-ethylenes of the formula R.sub.f CH.dbd.CH.sub.2 and possibly also with 2-(perfluoroalkyl)-ethylcarboxylic acid esters of the formula R.sub.f CH.sub.2 CH.sub.2 OCOR. From these mixtures, the 2-(perfluoroalkyl)-ethanols are obtained with a high purity degree when adding during the distillation separation as entrainer an alkanol having from 1 to 8 carbon atoms or a monoalkyl ether of ethyleneglycol the alkyl radical of which contains 1 to 4 carbon atoms, or a mixture of such alkanols and/or alkylglycols, and in the presence of 2-(perfluoroalkyl)-ethylcarboxylic acid esters, furthermore an acidic ester interchange catalyst.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: August 26, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Inge Konig, Horst Streitberger, Engelbert Krempl, Ulrich Schwenk
  • Patent number: 4214098
    Abstract: Novel cyclooctene derivatives of the formula: ##STR1## in which R.sup.1 and R.sup.2 each represents an alkyl group and R.sup.3 is hydrogen or an acyl group are disclosed along with their use as aroma chemicals and/or aroma chemical precursors and processes for their preparation.
    Type: Grant
    Filed: October 25, 1977
    Date of Patent: July 22, 1980
    Assignee: Shell Oil Company
    Inventors: Aaldert J. de Jong, Hendricus J. Heijmen
  • Patent number: 4117251
    Abstract: Straight-chain, primary alcohols are prepared by reacting straight-chain 1-bromoalkanes having 6 to 20 carbon atoms with alkali salts of monocarboxylic acids having 4 to 22 carbon atoms in the presence of 1 to 10 mole percent of monocarboxylic acids or alcohols based upon the alkali salt of the carboxylic acid and at temperatures ranging from to C. The esters formed are saponified in alkaline medium to the straight-chain, primary alcohols and separated.
    Type: Grant
    Filed: March 17, 1977
    Date of Patent: September 26, 1978
    Assignee: Chemische Werke Huls AG
    Inventors: Manfred Kaufhold, Gottfried Bankwitz
  • Patent number: 4088823
    Abstract: A process is provided for oxygenating alkyl-substituted aromatic compounds. In the process alkyl-substituted aromatic compounds are contacted with molecular oxygen in the presence of a suitable monocarboxylic acid, a soluble copper, cobalt, or iron compound, and an inorganic bromine compound. Optionally present are inorganic nitrates, acetic anhydride, or water. In an embodiment of the invention the process is carried out in two distinct steps with contact of the alkyl-substituted aromatic compounds and oxygen in the presence of the essential components produce an ester comprising both an aromatic alcohol and the carboxylic acid with subsequent hydrolyzing of this ester to produce an aromatic alcohol with regeneration of the carboxylic acid.
    Type: Grant
    Filed: October 7, 1975
    Date of Patent: May 9, 1978
    Assignee: Phillips Petroleum Company
    Inventors: Hans D. Holtz, Lloyd E. Gardner