Polyalkylol Substituted Alkane (e.g., Pentaerythritol, Trimethylolethane, Ect.) Patents (Class 568/853)
  • Patent number: 4847439
    Abstract: Crystallization of trimethylolethane from supersaturated aqueous solutions is inhibited in the presence of effective amounts of methanol and formic acid as crystallization inhibitors.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: July 11, 1989
    Assignee: International Minerals & Chemical Corp.
    Inventor: Paul E. Eckler
  • Patent number: 4822925
    Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: April 18, 1989
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, John H. Robson
  • Patent number: 4804789
    Abstract: The invention concerns D-mannitol derivatives of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are the same or different, and when R.sup.1 R.sup.2 are the same, signify a straight-chained or branched alkyl, alkenyl or alkynyl group with 6 to 24 carbon atoms, which can contain cycloalkyl radicals with 3 to 6 carbon atoms, aryl radicals, benzyloxy, allyloxy, mesyloxy and/or halogen substituents and, when R.sup.1 and R.sup.2 are different, signify a straight-chained or branched alkyl group with 1 to 24 carbon atoms, which can contain cycloalkyl radicals with 3 to 6 carbon atoms, aryl radicals, benzyloxy, allyloxy, mesyloxy and/or halogen substituents, or a straight-chained or branched alkenyl or alkynyl group with 3 to 24 carbon atoms, which can contain cycloalkyl radicals with 3 to 6 carbon atoms, aryl radicals, benzyloxy, allyloxy, mesyloxy and/or halogen substituents, and R.sup.1 can also be trityl.
    Type: Grant
    Filed: October 22, 1987
    Date of Patent: February 14, 1989
    Assignee: Max-Planck-Gesellschaft Zur Forderung der Wissenschaften E.V.
    Inventor: Hansjorg Eibl
  • Patent number: 4772727
    Abstract: A multistage method for producing R-(+)-.alpha.-lipoic acid and S-(-)-.alpha.-lipoic acid (thioctic acid) by reacting a compound of formula II ##STR1## by means of enantioselective epoxidation to the epoxy alcohol of formula III, ##STR2## reduction to 1,3-diol-dihydroxynone-8-ene of formula IV, ##STR3## reaction with a substituted sulfonic acid chloride to 1,3-disulfoxynone-8-ene of formula V, ##STR4## oxidation with ruthenium tetroxide to 6,8-disulfoxyoctanoic acid of formula VI ##STR5## and subsequent reaction with sodium sulfide/sulfur.
    Type: Grant
    Filed: August 7, 1987
    Date of Patent: September 20, 1988
    Assignee: Degussa
    Inventors: Ian O. Sutherland, Philip C. B. Page, Christopher M. Rayner
  • Patent number: 4740639
    Abstract: The invention relates to a process for the preparation of 2,4-disubstituted-1,5-pentanediols from formaldehyde and at least one simple aldehyde of the formula RCH.sub.2 CHO. More particularly the invention relates to a reaction to produce a 2,4-disubstituted glutaraldehyde wherein the reactant mole ratio of aldehyde/formaldehyde is between 1 and 8. The reaction is carried out in the presence of a secondary amine or secondary amine salt catalyst and leads to higher yields of the 2,4-disubstituted glutaraldehyde. The invention also relates to the production of 2,4-disubstituted-1,5-pentanediols by hydrogenation of the 2,4-disubstituted glutaraldehydes.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: April 26, 1988
    Assignee: Eastman Kodak Company
    Inventor: William A. Beavers
  • Patent number: 4709104
    Abstract: Crystallization of trimethylolethane from supersaturated aqueous solutions is inhibited in the presence of effective amounts of crystallization inhibitors selected from methanol, isopropanol, s-butyl alcohol, t-butyl alcohol, 2-ethoxyethanol, 2-methoxyethanol, 1-methoxy-2-propanol, formic acid and 1-dimethylamino-2-propanol.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: November 24, 1987
    Assignee: International Minerals & Chemical Corp.
    Inventor: Paul E. Eckler
  • Patent number: 4702853
    Abstract: A thermal energy storge composition is disclosed. The composition comprises a non-chloride hydrate having a phase change transition temperature in the range of 70.degree.-95.degree. F. and a latent heat of transformation of at least about 35 calories/gram.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: October 27, 1987
    Assignee: The United States of America as represented by the Department of Energy
    Inventors: David K. Benson, Richard W. Burrows
  • Patent number: 4645855
    Abstract: A process for the preparation of succinic acid diesters by carbonylation of acrylic acid esters in the presence of alcohols, using a cobalt carbonyl complex as the catalyst and a heterocyclic nitrogen base as the promoter, at 80.degree.-200.degree. C. and under a carbon monoxide pressure of 60-300 bar, wherein the reaction is carried out in the presence of not less than 20% by weight, based on the amount of all the liquid constituents of the reaction mixture, of an inert liquid and the concentration of the acrylic acid ester is kept, for the predominant part of the reaction time, at below 15% by weight, again based on the amount of all liquid constituents.
    Type: Grant
    Filed: August 24, 1984
    Date of Patent: February 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes G. Reuvers, Wolfgang Richter, Rudolf Kummer
  • Patent number: 4612389
    Abstract: This invention provides a process for improving the separation and recovery of metal formate and pentaerythritol as crystalline products, from an aqueous waste stream of a pentaerythritol manufacturing operation which involves the reaction of formaldehyde with acetaldehyde in the presence of a metal hydroxide catalyst.The pentaerythritol process waste stream is passed through a macroreticular resin bed to remove organic byproducts, and the purified waste stream is then evaporatively concentrated to produce crystalline sodium formate product. The resultant mother liquor is diluted with water-miscible alkanol to precipitate a pentaerythritol-metal formate mixture. The precipitate is washed with a portion of waste stream feed to dissolve the metal formate and yield undissolved crystalline pentaerythritol as a product.At least about 85 percent of the metal formate and at least about 90 percent of the pentaerythritol contained in the original waste stream are recovered as products of the process.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: September 16, 1986
    Assignee: Virginia Chemicals Inc.
    Inventors: Frank Gupton, Harry E. Ulmer
  • Patent number: 4599459
    Abstract: A method for the ultrasonic treatment of dilute alcoholic solution in which a vibrator member placed in a dilute alcoholic solution is subjected to ultrasonic vibrations to produce cavitation in the solution in such a way that alcohol in the solution is vaporized and collected in a high concentration. The alcohol may be readily converted into a corresponding aldehyde.
    Type: Grant
    Filed: August 31, 1984
    Date of Patent: July 8, 1986
    Inventor: Masanao Hirose
  • Patent number: 4594461
    Abstract: Trimethylolalkanes are prepared by reacting an n-alkanal with formaldehyde and a trialkylamine in aqueous solution and then hydrogenating the product, by a method in which from 2.2 to 4.5 moles of formaldehyde and from 0.6 to 3 moles of trialkylamine are used per mole of the alkanal, and the reaction mixture is worked up by distillation either before or after the hydrogenation.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: June 10, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Peter Hettinger, Leopold Hupfer, Juergen Paetsch
  • Patent number: 4582946
    Abstract: The present invention describes the production of high molecular weight polyhydric alcohols and their derivatives. In particular the urethane reaction products of polyisocyantes and polyhydric alcohols are described.
    Type: Grant
    Filed: March 16, 1982
    Date of Patent: April 15, 1986
    Assignee: Henkel Corporation
    Inventor: Edgar Rogier
  • Patent number: 4514578
    Abstract: Trimethylolpropane is prepared in such a manner that butyraldehyde is metered into a mixture of water, alkaline condensing agent and formaldehyde, which contains less than 0.1 mol of methanol relative to 1 mol of formaldehyde, at temperatures from 15.degree. to 50.degree. C., and after addition of the butyraldehyde the reaction mixture is heated up to 90.degree. C., sufficient water being present in the reaction mixture so that the reaction mixture has a content of trimethylolpropane of 5 to 25% by weight after the reaction.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: April 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Helmut Schwarz, Hein Quast, Eberhard Bandtel
  • Patent number: 4501840
    Abstract: Pentaerythritol is treated at a temperature of about 180.degree. to 220.degree. C. with a strongly alkaline acting material, e.g. calcium oxide. The thus treated pentaerythritol serves as a costabilizer e.g., with the salt of a polyvalent metal and a carboxylic acid, for a vinyl chloride resin, e.g. polyvinyl chloride and has outstanding properties as such.
    Type: Grant
    Filed: October 20, 1983
    Date of Patent: February 26, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Peter Werle, Wolfgang Merk
  • Patent number: 4435603
    Abstract: A polyol composition comprising a solid polyol which is crystalline under normal conditions and, as an anti-caking agent therefor, a tertiary amine containing at least two identical organic substituents, each having two to twenty carbon atoms. A method of preventing caking of polyols is disclosed wherein to such polyols there is added at least one of such tertiary amines, preferably in a concentration of 0.05 to 0.25 percent by weight based on the weight of the polyol.
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: March 6, 1984
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Boy Cornils, Hanswilhelm Bach, Roderich Gartner, Wilhelm Gick
  • Patent number: 4433159
    Abstract: Optically active alpha-tocopherol is synthesized by a multi-step process using phytol as a starting material. The process does not require an optical resolution step.
    Type: Grant
    Filed: February 18, 1982
    Date of Patent: February 21, 1984
    Assignee: Eisai Co., Ltd.
    Inventors: Kimio Hamamura, Kozo Akasaka, Youji Yamagishi
  • Patent number: 4386219
    Abstract: Hydrogenation catalysts, which have a specific surface area of from 50 to 150 square meters per gram, solely or partially contain crystals having a spinel structure and copper in the form of copper oxide, and have been obtained by precipitating copper and aluminum in a ratio of from 0.25 to 3 atoms of copper per atom of aluminum from their compounds in the presence of a carbonate at a pH of from 4.5 to 9 and calcining the resulting precipitate at from 300.degree. to 800.degree. C., for the catalytic preparation of propanediols by hydrogenating hydroxypropionaldehydes at not more than 300 bar pressure and from 50.degree. to 200.degree. C., and processes for the preparation of propanediols by the use of such catalysts.The propanediols obtainable by the process of the invention, in particular 2,2-dimethylpropane-1,3-diol, are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example corresponding polyesters.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: May 31, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
  • Patent number: 4347109
    Abstract: Acetaldehyde is obtained from an ethyl alcohol "fuel" anodically treated in a fuel cell, and the acetaldehyde (along with any evaporated, unreacted ethanol "fuel") is ultimately recovered in anhydrous or substantially anhydrous form. Further chemical and electrochemical transformation of acetaldehyde in the presence of the fuel cell anode is stopped or minimized to avoid the formation of condensates or polymers or more highly oxidized products (e.g., acetic acid or aldol condensates) which may act as catalyst poisons. For example, ethyl alcohol can be vaporized and fed to the gas side of a gas-permeable fluid-impermeable electrode, in which case up to 60 mole-% or more of the acetaldehyde product stays with the vapor stream and avoids further chemical reactions or side reactions, substantially the balance going into solution in the electrolyte, from which it can be recovered, e.g., by low temperature distillation.
    Type: Grant
    Filed: October 23, 1980
    Date of Patent: August 31, 1982
    Assignee: Electrohol Corporation
    Inventor: Thomas M. Meshbesher
  • Patent number: 4336408
    Abstract: 2-Hydroxymethyl-1,3-propanediol trinitrate, processes for its preparation, and compounds related thereto are disclosed. The final product is useful as a plasticizer of relatively low volatility in double based propellant compositions and as a liquid explosive.
    Type: Grant
    Filed: June 26, 1979
    Date of Patent: June 22, 1982
    Assignee: Thiokol Corporation
    Inventor: Michael W. Barnes
  • Patent number: 4329342
    Abstract: Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles and 1H-1,2,4-triazoles wherein the 1,3-dioxolane ring is substituted in the 4- and in the 5-positions, said compounds having useful antimicrobial properties.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: May 11, 1982
    Assignee: Janssen Pharmaceutica, N.V.
    Inventors: Jan Heeres, Leo Backx, Willy Van Laerhoven, Elmar Sturm
  • Patent number: 4328366
    Abstract: This invention provides a process for recovery of sodium formate from an aqueous waste stream which is a byproduct mother liquor derived from a reaction system in which pentaerythritol is produced by the reaction of formaldehyde with acetaldehyde in the presence of sodium hydroxide catalyst.As one of its important features, the invention process involves contacting the mother liquor with a monoalkylamine solvent which is highly selective for extraction of organic materials to the exclusion of sodium formate.
    Type: Grant
    Filed: February 25, 1980
    Date of Patent: May 4, 1982
    Assignee: Virginia Chemicals Inc.
    Inventors: Charles E. Winslow, Jr., Leonard C. Ellis
  • Patent number: 4328368
    Abstract: A method if provided for continuously hydrolyzing urethane foam in a vertically oriented hydrolysis reactor. In a preferred practice, a bed of foam particles is formed in the reactor. Superheated steam is flowed continuously upward through the bed at a temperature and rate such that only the foam particles then adjacent the bottom of the reactor are hydrolyzed and the bulk of the bed is not fluidized. Unreacted steam heats the unhydrolyzed foam. Liquid hydrolysis products are drained as they are formed to prevent hydrolysis-impeding liquid saturation of unhydrolyzed particles.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: May 4, 1982
    Assignee: General Motors Corporation
    Inventors: Robert J. Salloum, Clifford C. Duff
  • Patent number: 4320064
    Abstract: Particular polynuclear rhodium carbonyl complexes are provided which are useful in the production of polyhydric alcohols such as ethylene glycol by the reaction of carbon monoxide and hydrogen. These complexes are rhodium carbonyl cluster compounds comprising twenty-two rhodium atoms in the cluster cage.
    Type: Grant
    Filed: March 31, 1980
    Date of Patent: March 16, 1982
    Assignee: Union Carbide Corporation
    Inventor: Jose' L. Vidal
  • Patent number: 4317945
    Abstract: A process for the preparation of 2-methyl-2-sec.butyl-1,3-propanediol comprising hydroformylating 2-methyl-1-butene with carbon monoxide and hydrogen in the presence of a first catalyst to form the substance 3-methyl-pentanal, condensing said substance with formaldehyde, or a compound which forms formaldehyde under the conditions of condensation in a basic medium to form alpha-sec.butyl-acrolein, partially hydrogenating said acrolein in the presence of a second catalyst to form the material 2,3-dimethyl pentanal, and converting said material into said diol by treatment with formaldehyde, or a compound which forms formaldehyde under the conditions of conversion, in the presence of a strong base as a third catalyst.The compound of the present invention is useful as an intermediate in the production of pharmaceuticals and drugs; in particular, the production of carbamates which are useful as tranquilizers and blood pressure lowering agents.
    Type: Grant
    Filed: August 15, 1980
    Date of Patent: March 2, 1982
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Wolfgang Bernhagen, Jurgen Weber, Helmut Bahrmann, Helmut Springer
  • Patent number: 4304945
    Abstract: The present invention describes the production of high molecular weight polyhydric alcohols and their derivatives. In particular the urethane reaction products of polyisocyanates and polyhydric alcohols are described.
    Type: Grant
    Filed: October 4, 1979
    Date of Patent: December 8, 1981
    Assignee: Henkel Corporation
    Inventor: Edgar R. Rogier
  • Patent number: 4251673
    Abstract: An organic ester e.g. 1,4-diacetoxybutane is hydrolyzed with an alkali metal or an alkaline earth metal hydroxide to a corresponding alcohol, the reaction being rapidly effected by having present a hydroxyl-containing compound. In a preferred embodiment, the hydroxyl-containing compound to be present is the very compound to be produced e.g. 1,4-butanediol is to be produced from 1,4-diacetoxybutane and there is present during the reaction of hydrolysis an earlier produced 1,4-butanediol.
    Type: Grant
    Filed: July 3, 1979
    Date of Patent: February 17, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Harold W. Mark, William V. Childs
  • Patent number: 4250337
    Abstract: In a process for the production of neopentyl glycol comprising high-pressure hydrogenating a crude hydroxypivalaldehyde, containing the monoisobutyric acid ester of neopentyl glycol as an impurity, in the liquid phase over a barium-activated copper chromite catalyst, an improvement comprises hydrogenating the crude hydroxypivalaldehyde in the presence of 3-8% of water, and in two stages, wherein, in the first stage, the temperature is 120.degree.-160.degree. C. and the charge of hydrogenation starting material is 0.05-1.0 liter/liter of catalyst . h., and in the second stage, the temperature is 170.degree.-200.degree. C. and the charge of hydrogenation starting material is 0.05-1.0 liter/liter of catalyst . h., whereby there is obtained neopentyl glycol having a degree of purity of above 98% as determined by gas chromatographic analysis.
    Type: Grant
    Filed: June 22, 1979
    Date of Patent: February 10, 1981
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventors: Manfred zur Hausen, Manfred Kaufhold, Erhard Lange
  • Patent number: 4239641
    Abstract: A method for regulating the viscosity of aqueous detergent and cleanser slurries, in which there are added to the slurries, as viscosity regulators, dihydric, trihydric or tetrahydric aliphatic alcohols, monobasic aliphatic carboxylic acids, hydroxycarboxylic acids, esters of the said alcohols and the said acids or mixtures of these, in which compounds the alcohols, carboxylic acids and hydroxycarboxylic acids, and the individual components of the esters, are of 5 to 9 carbon atoms, of which one is a quaternary atom, the alcohols and hydroxycarboxylic acids carry exclusively primary alcohol groups, and the carboxylic acids and hydroxycarboxylic acids have the carboxyl group bonded to the quaternary carbon atom.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: December 16, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Perner, Paul Diessel, Dieter Stoeckigt, Franz Merger, Juergen Paetsch
  • Patent number: 4239552
    Abstract: A process for machine dishwashing, employing a rinsing liquor which contains carboxylic acids or hydroxycarboxylic acids or mixtures of these and dihydric, trihydric or tetrahydric alcohols, the alcohols and carboxylic acids being of 5 to 9 carbon atoms, of which one carbon atom is quaternary, the alcoholic hydroxyl groups being exclusively primary and the carboxyl group being bonded to the quaternary carbon atom.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: December 16, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Perner, Dieter Stoeckigt, Paul Diessel, Franz Merger, Juergen Paetsch
  • Patent number: 4235875
    Abstract: Novel alkyl 1-(hydroxyalkyl)piperidines and acid addition salts thereof, useful as inhibitors of dental plaque and therefore also useful against dental caries and periodontitis, are disclosed. Methods of making same, orally-acceptable compositions thereof, a method of treating therewith, and important and novel intermediates for the production thereof are also disclosed.
    Type: Grant
    Filed: April 24, 1978
    Date of Patent: November 25, 1980
    Assignee: A.B. Ferrosan
    Inventors: Sven E. H. Hernestam, Lars O. Willard, Aina L. Abramo, Hans-Bertil Johansson
  • Patent number: 4229562
    Abstract: The present invention describes the production of high molecular weight polyhydric alcohols and their derivatives. In particular the urethane reaction products of polyisocyanates and polyhydric alcohols are described. The particular urethane products of the present invention are obtained using an alcohol having a terminal hydroxyl functionality and a geminal hydroxymethyl structure. The particular urethan products of the present invention are obtained using an alcohol having a terminal hydroxyl functionality and a geminal hydroxymethyl structure.
    Type: Grant
    Filed: April 4, 1979
    Date of Patent: October 21, 1980
    Assignee: Henkel Corporation
    Inventor: Edgar R. Rogier
  • Patent number: 4216343
    Abstract: The present invention describes the production of high molecular weight polyhydric alcohols and their derivatives. In particular the urethane reaction products of polyisocyantes and polyhydric alcohols are described.
    Type: Grant
    Filed: April 4, 1979
    Date of Patent: August 5, 1980
    Assignee: Henkel Corporation
    Inventor: Edgar R. Rogier
  • Patent number: 4216344
    Abstract: The present invention describes the production of high molecular weight polyhydric alcohols and their derivatives. In particular the urethane reaction products of polyisocyantes and polyhydric alcohols are described.
    Type: Grant
    Filed: April 4, 1979
    Date of Patent: August 5, 1980
    Assignee: Henkel Corporation
    Inventor: Edgar R. Rogier
  • Patent number: 4175053
    Abstract: Alkyl nitriles in combination with alkali metal hydroxides provide super bases which are useful in various chemical processes.
    Type: Grant
    Filed: October 12, 1976
    Date of Patent: November 20, 1979
    Assignee: The Procter & Gamble Company
    Inventor: Donald J. Peterson
  • Patent number: 4122290
    Abstract: An improved process for the preparation of a trimethylolalkane of the formula ##STR1## wherein R.sup.1 denotes an aliphatic radical by reacting formaldehyde with an aldehyde of the formula ##STR2## wherein R.sup.1 has the meaning indicated above and thereafter hydrogenating the resultant 2,2-dimethylolalkanal, the improvement residing in employing formaldehyde in a molar ratio of at least 8:1 to the aldehyde reactant, carrying out the aldehyde-formaldehyde reaction in the presence of an aldol condensation base at a temperature between -20 and 5.degree. C, optionally in the presence of an ion of an element of group VII and/or VIII and/or sub-group I or II of the periodic system.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: October 24, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel, Heinrich Krimm
  • Patent number: 4091040
    Abstract: A process for the production of trimethylolmethane in high yields. Trimetolmethane is useful as the essential precurser to trimethylolmethane trinitrate, a high-energy plasticizer and explosive.
    Type: Grant
    Filed: July 21, 1977
    Date of Patent: May 23, 1978
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Arnold T. Nielsen
  • Patent number: H253
    Abstract: Energetic branched polynitrodiols of the formula ##STR1## wherein Z is --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --C(NO.sub.2).su CH.sub.3, or --N(NO.sub.2)CH.sub.3, and a method of preparation. These diols are useful as components of energetic binders for plastic-bonded explosives.
    Type: Grant
    Filed: June 17, 1986
    Date of Patent: April 7, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, William H. Gilligan