Polyalkylol Substituted Alkane (e.g., Pentaerythritol, Trimethylolethane, Ect.) Patents (Class 568/853)
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Patent number: 4847439Abstract: Crystallization of trimethylolethane from supersaturated aqueous solutions is inhibited in the presence of effective amounts of methanol and formic acid as crystallization inhibitors.Type: GrantFiled: August 10, 1987Date of Patent: July 11, 1989Assignee: International Minerals & Chemical Corp.Inventor: Paul E. Eckler
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Patent number: 4822925Abstract: 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: GrantFiled: February 6, 1987Date of Patent: April 18, 1989Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4804789Abstract: 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: GrantFiled: October 22, 1987Date of Patent: February 14, 1989Assignee: Max-Planck-Gesellschaft Zur Forderung der Wissenschaften E.V.Inventor: Hansjorg Eibl
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Patent number: 4772727Abstract: 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: GrantFiled: August 7, 1987Date of Patent: September 20, 1988Assignee: DegussaInventors: Ian O. Sutherland, Philip C. B. Page, Christopher M. Rayner
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Patent number: 4740639Abstract: 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: GrantFiled: June 12, 1987Date of Patent: April 26, 1988Assignee: Eastman Kodak CompanyInventor: William A. Beavers
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Patent number: 4709104Abstract: 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: GrantFiled: October 15, 1985Date of Patent: November 24, 1987Assignee: International Minerals & Chemical Corp.Inventor: Paul E. Eckler
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Patent number: 4702853Abstract: 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: GrantFiled: October 6, 1986Date of Patent: October 27, 1987Assignee: The United States of America as represented by the Department of EnergyInventors: David K. Benson, Richard W. Burrows
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Patent number: 4645855Abstract: 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: GrantFiled: August 24, 1984Date of Patent: February 24, 1987Assignee: BASF AktiengesellschaftInventors: Johannes G. Reuvers, Wolfgang Richter, Rudolf Kummer
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Patent number: 4612389Abstract: 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: GrantFiled: May 10, 1982Date of Patent: September 16, 1986Assignee: Virginia Chemicals Inc.Inventors: Frank Gupton, Harry E. Ulmer
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Patent number: 4599459Abstract: 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: GrantFiled: August 31, 1984Date of Patent: July 8, 1986Inventor: Masanao Hirose
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Patent number: 4594461Abstract: 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: GrantFiled: November 5, 1984Date of Patent: June 10, 1986Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger, Leopold Hupfer, Juergen Paetsch
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Patent number: 4582946Abstract: 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: GrantFiled: March 16, 1982Date of Patent: April 15, 1986Assignee: Henkel CorporationInventor: Edgar Rogier
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Patent number: 4514578Abstract: 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: GrantFiled: June 22, 1984Date of Patent: April 30, 1985Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Hein Quast, Eberhard Bandtel
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Patent number: 4501840Abstract: 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: GrantFiled: October 20, 1983Date of Patent: February 26, 1985Assignee: Degussa AktiengesellschaftInventors: Peter Werle, Wolfgang Merk
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Patent number: 4435603Abstract: 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: GrantFiled: March 11, 1981Date of Patent: March 6, 1984Assignee: Ruhrchemie AktiengesellschaftInventors: Boy Cornils, Hanswilhelm Bach, Roderich Gartner, Wilhelm Gick
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Patent number: 4433159Abstract: 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: GrantFiled: February 18, 1982Date of Patent: February 21, 1984Assignee: Eisai Co., Ltd.Inventors: Kimio Hamamura, Kozo Akasaka, Youji Yamagishi
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Patent number: 4386219Abstract: 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: GrantFiled: February 2, 1982Date of Patent: May 31, 1983Assignee: BASF AktiengesellschaftInventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
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Patent number: 4347109Abstract: 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: GrantFiled: October 23, 1980Date of Patent: August 31, 1982Assignee: Electrohol CorporationInventor: Thomas M. Meshbesher
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Patent number: 4336408Abstract: 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: GrantFiled: June 26, 1979Date of Patent: June 22, 1982Assignee: Thiokol CorporationInventor: Michael W. Barnes
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Patent number: 4329342Abstract: 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: GrantFiled: November 3, 1980Date of Patent: May 11, 1982Assignee: Janssen Pharmaceutica, N.V.Inventors: Jan Heeres, Leo Backx, Willy Van Laerhoven, Elmar Sturm
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Patent number: 4328366Abstract: 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: GrantFiled: February 25, 1980Date of Patent: May 4, 1982Assignee: Virginia Chemicals Inc.Inventors: Charles E. Winslow, Jr., Leonard C. Ellis
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Patent number: 4328368Abstract: 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: GrantFiled: May 5, 1980Date of Patent: May 4, 1982Assignee: General Motors CorporationInventors: Robert J. Salloum, Clifford C. Duff
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Patent number: 4320064Abstract: 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: GrantFiled: March 31, 1980Date of Patent: March 16, 1982Assignee: Union Carbide CorporationInventor: Jose' L. Vidal
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Patent number: 4317945Abstract: 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: GrantFiled: August 15, 1980Date of Patent: March 2, 1982Assignee: Ruhrchemie AktiengesellschaftInventors: Wolfgang Bernhagen, Jurgen Weber, Helmut Bahrmann, Helmut Springer
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Patent number: 4304945Abstract: 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: GrantFiled: October 4, 1979Date of Patent: December 8, 1981Assignee: Henkel CorporationInventor: Edgar R. Rogier
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Patent number: 4251673Abstract: 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: GrantFiled: July 3, 1979Date of Patent: February 17, 1981Assignee: Phillips Petroleum CompanyInventors: Harold W. Mark, William V. Childs
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Patent number: 4250337Abstract: 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: GrantFiled: June 22, 1979Date of Patent: February 10, 1981Assignee: Chemische Werke Huls AktiengesellschaftInventors: Manfred zur Hausen, Manfred Kaufhold, Erhard Lange
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Patent number: 4239641Abstract: 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: GrantFiled: July 23, 1979Date of Patent: December 16, 1980Assignee: BASF AktiengesellschaftInventors: Johannes Perner, Paul Diessel, Dieter Stoeckigt, Franz Merger, Juergen Paetsch
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Patent number: 4239552Abstract: 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: GrantFiled: July 23, 1979Date of Patent: December 16, 1980Assignee: BASF AktiengesellschaftInventors: Johannes Perner, Dieter Stoeckigt, Paul Diessel, Franz Merger, Juergen Paetsch
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Patent number: 4235875Abstract: 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: GrantFiled: April 24, 1978Date of Patent: November 25, 1980Assignee: A.B. FerrosanInventors: Sven E. H. Hernestam, Lars O. Willard, Aina L. Abramo, Hans-Bertil Johansson
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Patent number: 4229562Abstract: 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: GrantFiled: April 4, 1979Date of Patent: October 21, 1980Assignee: Henkel CorporationInventor: Edgar R. Rogier
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Patent number: 4216343Abstract: 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: GrantFiled: April 4, 1979Date of Patent: August 5, 1980Assignee: Henkel CorporationInventor: Edgar R. Rogier
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Patent number: 4216344Abstract: 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: GrantFiled: April 4, 1979Date of Patent: August 5, 1980Assignee: Henkel CorporationInventor: Edgar R. Rogier
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Patent number: 4175053Abstract: Alkyl nitriles in combination with alkali metal hydroxides provide super bases which are useful in various chemical processes.Type: GrantFiled: October 12, 1976Date of Patent: November 20, 1979Assignee: The Procter & Gamble CompanyInventor: Donald J. Peterson
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Patent number: 4122290Abstract: 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: GrantFiled: December 16, 1977Date of Patent: October 24, 1978Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel, Heinrich Krimm
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Patent number: 4091040Abstract: 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: GrantFiled: July 21, 1977Date of Patent: May 23, 1978Assignee: The United States of America as represented by the Secretary of the NavyInventor: Arnold T. Nielsen
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Patent number: H253Abstract: 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: GrantFiled: June 17, 1986Date of Patent: April 7, 1987Assignee: The United States of America as represented by the Secretary of the NavyInventors: Michael E. Sitzmann, William H. Gilligan