Polyhydroxy (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/811)
  • Patent number: 4579983
    Abstract: In processes for the hydrolysis of alkylene oxide to form alkylene glycols in the presence of selectivity-enhancing organometalate wherein the organometalate is provided in a water-insoluble phase, a stabilizing material is used to enhance the stability of the organometalate. The stabilizing material is water-soluble and comprises a cation and a selectivity-enhancing metalate anion.
    Type: Grant
    Filed: March 28, 1984
    Date of Patent: April 1, 1986
    Assignee: Union Carbide Corporation
    Inventor: Brian T. Keen
  • Patent number: 4579982
    Abstract: Alkylene oxides are hydrolyzed in a reaction menstruum containing an aqueous phase, a water-immiscible liquid phase, and a selectivity-enhancing, dissociatable metalate anion-containing material. The concentration of the metalate anion-containing material is greater in the water-immiscible liquid phase than that in the aqueous phase. The water-immiscible liquid phase can be separated from the aqueous phase to recover metalate anion-containing material.
    Type: Grant
    Filed: March 28, 1984
    Date of Patent: April 1, 1986
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, John H. Robson
  • Patent number: 4578524
    Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in the presence of vanadate anion and a selectivity-enhancing amount of carbon dioxide.
    Type: Grant
    Filed: March 28, 1984
    Date of Patent: March 25, 1986
    Assignee: Union Carbide Corporation
    Inventor: Brian T. Keen
  • Patent number: 4571440
    Abstract: A continuous process for making alkylene glycols by the hydrolysis of alkylene oxides in the presence of selectivity-enhancing organometalate wherein the alkylene glycol-containing hydrolysis product contains organometalate comprises recovering organometalate by extraction with a water-immiscible solvent, separating the resulting organometalate-containing solvent into an organometalate-lean stream for reuse in the extraction and an organometalate-rich stream for reuse in the hydrolysis.
    Type: Grant
    Filed: October 23, 1984
    Date of Patent: February 18, 1986
    Assignee: Union Carbide Corporation
    Inventors: Brian T. Keen, John H. Robson
  • Patent number: 4564715
    Abstract: High selectivity to monoalkylene glycol is obtained by contacting in an associated moiety-forming zone alkylene oxide and a selectivity enhancing, dissociatable metalate anion under conditions sufficient to associate at least a portion of the alkylene oxide with metalate anion, and then contacting the associated moiety with water in a glycol-forming zone to form alkylene glycol. The alkylene glycol can be separated from metalate anion. Desirably, the metalate anion can be recycled to the associated moiety-forming zone.
    Type: Grant
    Filed: October 23, 1984
    Date of Patent: January 14, 1986
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, George L. O'Connor, John H. Robson
  • Patent number: 4562299
    Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: December 31, 1985
    Assignee: Montedison S.p.A.
    Inventors: Carlo Venturello, Mario Gambaro
  • Patent number: 4560811
    Abstract: Novel methods for making chlorohydrins are provided using a Lewis acid catalyst with an olefin and peroxy compound or where an enantiomer is desired, a Lewis acid catalyst in combination with a chiral alcohol, particularly glycol, and a combination of a peroxy compound and alkenol. In certain situations, an epoxide may be employed.
    Type: Grant
    Filed: January 18, 1984
    Date of Patent: December 24, 1985
    Assignee: Massachusetts Institute of Technology
    Inventors: Karl B. Sharpless, Roy A. Johnson
  • Patent number: 4560813
    Abstract: In processes for making alkylene glycols by the hydrolysis of alkylene oxides in the presence of selectivity-enhancing metalate anion-containing material, metalate anion can be recovered from the alkylene glycol-containing hydrolysis product by contact with a solid having electropositive complexing sites thereon such as anion exchange resins.
    Type: Grant
    Filed: March 28, 1984
    Date of Patent: December 24, 1985
    Assignee: Union Carbide Corporation
    Inventor: Joseph A. Collier
  • Patent number: 4551566
    Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in the presence of a vanadate salt wherein the pH of the liquid phase is between about 5 and 12.
    Type: Grant
    Filed: September 8, 1983
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventors: John H. Robson, George E. Keller, II
  • Patent number: 4533772
    Abstract: The process for hydroxylating olefins with oxygen in the presence of water, an osmium-halide (e.g., OsBr.sub.3) catalyst and transition metal containing co-catalyst (CuBr.sub.2) is disclosed.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: August 6, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4533773
    Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an osmium oxide catalyst such as OsO.sub.4, a carboxylate salt co-catalyst, such as sodium acetate, and organic hydroperoxide oxidant is disclosed.
    Type: Grant
    Filed: March 22, 1984
    Date of Patent: August 6, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4510338
    Abstract: The invention relates to new resorcin derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 3 carbon atoms or alkoxy having from one to 3 carbon atoms.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 9, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4508926
    Abstract: The invention relates to new 4-hydroxy-benzhydrols of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms, with the proviso that if R.sub.1 is hydrogen, R.sub.2 is other than hydrogen or a 3-trifluoromethyl group, or if R.sub.1 is a 2-methyl group, R.sub.2 is other than a 5-methyl group.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredients are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 2, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4507510
    Abstract: Xylyleneglycol is produced by diazotization reaction of xylylenediamine in the presence of more than 5 parts by weight of water per 1 part of xylylenediamine, while maintaining the PH of the reaction mixture in the range of 1.5 to 5.0.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: March 26, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shigeo Yoshinaka, Tsukasa Toki, Tomoji Tsuji, Seiji Uchiyama
  • Patent number: 4497830
    Abstract: Compounds of Formula I ##STR1## wherein X is oxygen or CH.sub.2 ;A is CH.sub.2 --CH.sub.2, trans-CH.dbd.CH or C.tbd.C;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## and the OH groups may be in the .alpha.- or the .beta.-position; D is straight chain or branched, saturated or unsaturated hydrocarbon aliphatic of from 1 to 10 carbon atoms, which may be substituted by fluorine;E is C.tbd.C or CR.sub.3 .dbd.CR.sub.4, R.sub.3 and R.sub.4 being different and being hydrogen or alkyl of 1 to 5 carbon atoms;R.sub.1 is free or functionally modified hydroxy; andR.sub.2 is alkyl, cycloalkyl, optionally substituted aryl or heterocyclic,have valuable pharmacological properties, e.g., hypotensive and bronchodilatory characteristics. They can furthermore be used for prophylaxis and therapy of coronary infarct and as a treatment for stroke. They are produced by means of reduction of the corresponding 1-carbonic acid derivatives.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: February 5, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Gerda Mannesmann, Bob Nieuweboer
  • Patent number: 4496778
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as pyridine is disclosed.
    Type: Grant
    Filed: October 3, 1983
    Date of Patent: January 29, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
  • Patent number: 4496779
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as 1,4-diazabicyclo [2.2.2.] octane is disclosed.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: January 29, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
  • Patent number: 4486613
    Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an oxidant selected from organic hydroperoxides, H.sub.2 O.sub.2, and oxygen and a catalyst composition comprising at least one osmium carbonyl catalyst, such as Os.sub.3 (CO).sub.12, and optionally at least one cocatalyst such as NaI, is disclosed.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: December 4, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
  • Patent number: 4482760
    Abstract: 1,2-Diols of the formula: ##STR1## where R.sub.1 and R.sub.2 are hydrogen, alkyl of 1 to 10 carbon atoms or such as alkyl substituted by a halogen, a hydroxy group, a phenyl group, a methoxy group, or an ethoxy group, a phenyl group or a furyl group or R.sub.1 and R.sub.2 together form an alkylene group of 2 to 7 carbon atoms are formed by hydrogenating a correspondingly substituted cyanohydrin in an aqueous medium first in the presence of a hydrogenation catalyst and an acid at a temperature between -20.degree. and +25.degree. C. and a hydrogen pressure of less than 10 bar until per mole of cyanohydrin employed there is taken up one mole of hydrogen and then the hydrogenation continued to the end of the absorption of hydrogen in the presence of metallic nickel at a temperature between 30.degree. and 100.degree. C. and a hydrogen pressure between 10 and 150 bar.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: November 13, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Klaus Deller, Karlheinz Drauz, Bernd Lehmann
  • Patent number: 4482763
    Abstract: A process for hydroxylating olefins with an organic hydroperoxide and water in the presence of an osmium containing catalyst (e.g. OsO.sub.4) and an organic halogenated hydrocarbon co-catalyst (e.g., n-butyl iodide) is disclosed.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: November 13, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard G. Austin, Robert C. Michaelson
  • Patent number: 4460800
    Abstract: The preparation of hydroxyaryldialkylcarbinols by the reaction of hydroxyaryl alkyl ketones or alkyl hydroxyarenecarboxylates with Grignard reagents in a mixed ether-aromatic hydrocarbon solvent is frequently difficult on a large-scale basis because of formation of a voluminous precipitate of mixed magnesium salt. In an improvement in this process, a solution of the ketone or ester in an ether is added to the solution of the Grignard reagent.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: July 17, 1984
    Assignee: General Electric Company
    Inventors: Charles M. Orlando, Howard J. Klopfer
  • Patent number: 4448987
    Abstract: A process is disclosed for preparation of hydroxymethyl aryl monocarboxylic acid compounds by reduction of arylene dicarboxylic acid compounds in the presence of a rhenium catalyst and an aqueous solvent.
    Type: Grant
    Filed: November 30, 1982
    Date of Patent: May 15, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventor: Lawrence D. Lillwitz
  • Patent number: 4413151
    Abstract: A process for hydroxylating olefins using a supported osmium catalyst such as Os.sub.3 (CO).sub.12 adsorbed on a support, such as MgO, and optionally in conjunction with a co-catalyst such as NaI, is disclosed.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: November 1, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
  • Patent number: 4393251
    Abstract: Hydrogenation catalysts which are prepared from mixed crystals of copper-zinc compounds, obtained by precipitation, of the formulaCu.sub.1.5-3 Zn.sub.1-2.5 (CO.sub.3).sub.1-2 (OH).sub.4-6.(H.sub.2 O).sub.0-1by decomposition at 200.degree.-500.degree. C., and are used for the catalytic preparation of propanediols of the formula ##STR1## where the R's may be identical or different and each is an aliphatic, araliphatic or aromatic radical, or the two R's together with the adjacent carbon atom are members of an alicyclic ring, by hydrogenating hydroxypropionaldehydes of the formula ##STR2## where R has the above meanings, and to processes for the preparation of propanediols, using such catalysts. The propane-1,3-diols obtainable by the novel process are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example of polyesters derived from the propanediols.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: July 12, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz J. Broecker, Leopold Hupfer, Franz Merger, Ernest Miesen, Juergen Paetsch, Guenter Zirker
  • Patent number: 4393253
    Abstract: A method for preparing polyols such as diols by catalytic hydroxylation of an olefinic compound by reacting the olefinic compound with an organic hydroperoxide and water in the presence of a catalyst comprising osmium compound and a specific halide co-catalyst is disclosed.
    Type: Grant
    Filed: October 9, 1981
    Date of Patent: July 12, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4393242
    Abstract: Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: July 12, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Meyer Sletzinger
  • Patent number: 4393075
    Abstract: New quinone compounds of the formula: ##STR1## wherein R.sup.1 is methyl or methoxy, or the two R.sup.1 groups jointly represent --CH.dbd.CH--CH.dbd.CH--; X is --CH.dbd.CH-- or --C.dbd.C--; Y.sup.1 is hydrogen, hydroxyl, carboxyl, cyano, acyloxy or --COZ in which Z is amino which may be substituted; m is zero or an integer of 1 to 3; n is zero or an integer of 1 to 10; n' is an integer of 1 to 5; k is an integer of 1 to 3; and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH.sub.2).sub.n' group; and their hydroquinone forms and salts, have useful physiological activities such as antiasthmatic, antiallergic and bloodpressure decreasing activities.
    Type: Grant
    Filed: March 26, 1981
    Date of Patent: July 12, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Mitsuru Shiraishi, Yoshitaka Maki
  • Patent number: 4390739
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins with an oxygen containing gas and water in the presence of a catalyst composition comprising (i) a catalytically active metal oxide such as OsO.sub.4, (ii) as a co-catalyst I a transition metal salt such as CuBr.sub.2, and (iii) optionally a co-catalyst II salt such as tetra ethyl ammonium bromide is disclosed.
    Type: Grant
    Filed: October 9, 1981
    Date of Patent: June 28, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4358624
    Abstract: Phenol reactants and fluorinated aldehydes or fluorinated ketones are reacted in the presence of organic sulfonic acid catalysts to yield fluorinated monophenols and fluorinated diphenols. Fluorinated monophenols can be isolated and reacted with additional phenol reactant in the presence of organic sulfonic acid catalysts to yield asymmetrical, as well as symmetrical, fluorinated diphenols. A preferred organic sulfonic acid catalyst is methanesulfonic acid. The novel fluorinated monophenols have a hydroxy group and a fluorinated aryl radical or fluorinated alkyl radical substituted upon the benzylic carbon atom. The novel fluorinated diphenols have at least one fluorinated aryl radical or fluorinated alkyl radical substituted upon the methylene carbon atom of the bisphenol.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: November 9, 1982
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4338290
    Abstract: Glycols are readily and conveniently prepared by hydrolysis of halohydrins and/or dihaloalkanes in the presence of a catalytically effective amount of a strong acid.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: July 6, 1982
    Assignee: National Distillers & Chemical Corp.
    Inventors: Jawad H. Murib, John M. Inskeep
  • Patent number: 4333952
    Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen, halogen or C.sub.1-4 alkoxy;X is oxygen; NR.sup.3 in which R.sup.3 is hydrogen, C.sub.1-4 alkyl, or -Y-R.sup.2 ; --C.dbd.O; or --CHOH;Y is --CH.sub.2 --CHOH, and when X is --C.dbd.O it may also be --CH.dbd.CH--; andR.sup.2 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenated;or salts thereof, are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: June 8, 1982
    Assignee: Beecham Group Limited
    Inventor: Brian G. McDonald
  • Patent number: 4314088
    Abstract: Method for preparing polyols such as diols and triols by the homogeneous catalytic hydroxylation of an olefinic compound by contacting the olefinic compound with an organic hydroperoxide in an inert polar solvent containing catalytic amounts of an osmium compound and a halide and at least a stoichiometric amount of water based on the amount of said olefinic compound.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: February 2, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard G. Austin, Robert C. Michaelson
  • Patent number: 4308408
    Abstract: Styrene or styrene substituted in the aromatic nucleus or on the vinyl group with a methyl group or styrene having the vinyl group substituted by hydroxymethyl is reacted with less than 2 moles of formic acid and less than 2 moles of hydrogen peroxide per mole of styrene or substituted styrene to hydroxylate the double bond. The formic acid is employed at a concentration between 20 and 100 weight percent and the hydrogen peroxide is employed at a concentration of less than 50 weight %. The concentration of the hydrogen peroxide in the aqueous phase of the reaction mixture is held below 15 weight percent during the entire reaction.The corresponding diols or triols are formed directly from the olefins employed within reasonable reaction times in high yields.
    Type: Grant
    Filed: September 16, 1980
    Date of Patent: December 29, 1981
    Assignee: Degussa Aktiengesellschaft
    Inventors: Gerhard Kabisch, Horst Malitius, Siegfried Raupach, Rudolf Trube, Hans Wittmann
  • 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: 4283580
    Abstract: A process for the production of alkylene glycols, which comprises causing a corresponding alkylene carbonate to react with water in the presence of a catalyst of at least one member selected from the group consisting of molybdenum and tungsten.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: August 11, 1981
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Hiroshi Odanaka, Minoru Saotome, Toshihiko Kumazawa
  • Patent number: 4277632
    Abstract: A process for the production of alkylene glycols, which comprises causing a corresponding alkylene oxide to react with water in the presence of a catalyst of at least one member selected from the group consisting of molybdenum and tungsten.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: July 7, 1981
    Assignee: Nippon Shokubai Kaguku Kogyo Co., Ltd.
    Inventors: Toshihiko Kumazawa, Takeshi Yamamoto, Hiroshi Odanaka
  • Patent number: 4271319
    Abstract: The present invention relates to a novel organic compound, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, and(c) converting the epoxide to a chlorohydrin, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: June 2, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4243683
    Abstract: Tertiary alcohols of the formula: ##STR1## wherein Y.sup.1 represents a carbonyl or hydroxymethylene group, and either(i) A.sup.1 represents a direct bond and R.sup.1 represents a phenyl group which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, or(ii) A.sup.1 represents a straight- or branched-chain alkylene group containing from 1 to 10 carbon atoms and R.sup.1 represents a hydrogen atom, or a phenyl, phenoxy or phenylthio group each of which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, are new compounds of use in the field of mammalian reproduction and also of use in the control of insects and acarines.
    Type: Grant
    Filed: October 3, 1978
    Date of Patent: January 6, 1981
    Assignee: May & Baker Limited
    Inventors: Barbara J. Broughton, Michael P. L. Caton, David J. Hambling
  • Patent number: 4191696
    Abstract: A new liquid phase oxidation process in which a metal nitro complex transfers an oxygen atom from the nitro ligand to a substrate; especially such process conducted cyclically or catalytically using molecular oxygen as the oxygen source. Metal nitrosyl complex is formed as a coproduct together with an oxidation product of the substrate. In a catalytic process, molecular oxygen maintains a concentration of nitro ligand in the reaction mixture. In a cyclic process, nitrosyl ligand of the metal nitrosyl coproduct is reoxidized by molecular oxygen in presence of a monodentate base such as pyridine to nitro ligand; and the nitro complex, thus regenerated, can be used again to oxidize the substrate, In particular the metal is a Group VIII metal, especially cobalt and the nitro complex is pyridine cobalt nitro saloph. To accelerate oxidation of the substrate at given temperature, a cocatalyst is included in the reaction mixture, e.g.
    Type: Grant
    Filed: July 24, 1978
    Date of Patent: March 4, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Benjamin S. Tovrog, Steven E. Diamond, Frank Mares
  • Patent number: 4178293
    Abstract: Esters of lower alkanoic acids substituted at the .alpha.-position with isoindoline or tetrahydroisoquinoline, and intermediates therefor, useful as pesticides.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: December 11, 1979
    Assignee: Zoecon Corporation
    Inventors: Clive A. Henrick, Robert L. Carney, Jeffrey N. Labovitz
  • Patent number: 4165330
    Abstract: An asymmetric synthesis process which involves addition of optically active chelated organometal compounds of lithium, sodium, beryllium, magnesium, zinc, copper and cadmium to prochiral unsaturated substrates. The optically active chelating agent is not consumed and can be recycled.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: August 21, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Thomas A. Whitney, Arthur W. Langer, Jr.
  • Patent number: 4163865
    Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.
    Type: Grant
    Filed: April 3, 1978
    Date of Patent: August 7, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
  • Patent number: 4151294
    Abstract: Alkynols of the formula, ##STR1## wherein X is F, Cl or Br; n is 0 or 1; m is 0 or 1 and R (if m is 0) is hydroxyalkyl of 1-6 carbon atoms or (if m is 1) alkyl, straight-chain hydroxyalkyl or straight-chain tetrahydropyran-2-yloxyalkyl of 2-6 carbon atoms in the alkyl, have anti-inflammatory activity.
    Type: Grant
    Filed: June 9, 1977
    Date of Patent: April 24, 1979
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Hans-Adolf Kurmeier, Erich Schacht, Joachim Gante, Dieter Orth, Zdenek Simane, Albrecht Wild
  • Patent number: 4112243
    Abstract: A process whereby photograde quality hydroquinone can be separated from the reaction mixture produced by a rearrangement of p-diisopropylbenzene dihydroperoxide, which process comprises the steps of (1) subjecting the mixture to hydrogenation to remove color; (2) concentrating the colorless solution; (3) adding a solvent to the concentrated mixture which dissolves impurities but which causes the hydroquinone to precipitate; and (4) separating the hydroquinone from the supernatant liquid in step (3).
    Type: Grant
    Filed: September 14, 1977
    Date of Patent: September 5, 1978
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Edward Norbert Nowak, Lawson Gibson Wideman, David Alan Hutchings
  • Patent number: 4107444
    Abstract: Thermally stable, rigid, aliphatic diols of the formula ##STR1## where R is a substituted or unsubstituted arylene group are useful as intermediates for forming polymers such as thermally stable, rigid polyesters.
    Type: Grant
    Filed: December 16, 1976
    Date of Patent: August 15, 1978
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Elmore Louis Martin