Polyoxy Patents (Class 562/587)
  • Patent number: 4575558
    Abstract: Described is a process for preparing 2,2'-disubstituted-1,3-dioxolane-4-methanol compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl, cycloalkyl or R.sub.1 and R.sub.2 together with the carbon atom form a 3 to 6 member cycloalkyl group, or aryl, the process comprising: reacting D- or L-serine with a nitrosating agent in an aqueous solution in the presence of formic acid, acetic acid, or propanoic acid to prepare 2,3-dihydroxypropanoic acid (D- or L-glyceric acid), the aqueous solution comprising from about 0.1 to 0.5 liter of water per mole of the serine starting material; reacting the glyceric acid so formed with 2,2-dimethoxypropane in the presence of a loweralkyl alcohol to prepare the D- or L-glyceric acid alkyl ester which is reacted with a selected aldehyde or ketone or the acetal or ketal derivative to prepare the corresponding 1,3-dioxolane derivative.
    Type: Grant
    Filed: February 15, 1984
    Date of Patent: March 11, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Khuong H. X. Mai, Ghanshyam Patil
  • 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: 4504421
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: March 12, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • Patent number: 4504422
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: March 12, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • Patent number: 4501705
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: February 26, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • 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: 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: 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: 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: 4461910
    Abstract: A process for the co-production of an alkylidene dicarboxylate and a carboxylic acid, which comprises hydrogenating a carboxylic acid anhydride in the presence of carbon monoxide and a homogeneous iridium- and/or rhodium-containing catalyst, together with an organo phosphorus (III), arsenic (III), or antimony (III) compound and either molecular oxygen or a phosphorus (V), arsenic (V) or antimony (V) compound containing a X=O moiety, where X is a phosphorus, arsenic or antimony atom.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: July 24, 1984
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4432801
    Abstract: A process for the controlled degradation of liquid glucose syrups in concentrated solution and in homogeneous phase wherein the reducing groups of glucose, maltose and maltodextrin are converted into the salts of the corresponding aldonic acids and/or into the salts of lower carboxylic acids (C.sub.1 -C.sub.4) without substantially changing the polysaccharide components (degree of polymerization>3) of maltodextrin, or with only partial depolymerization of the polysaccharide components, by using simple oxidants such as hypohalogenites or ferricyanides, or aqueous alkaline solutions. The conversion of the reducing sugars is equal to or greater than 95%, and a very high reproductibility of the desired results is obtained. The invention also concerns the product obtained by the process and its use as an additive to cement mortars and concretes.
    Type: Grant
    Filed: May 4, 1981
    Date of Patent: February 21, 1984
    Assignee: Grace Italiana S.p.A.
    Inventors: Fabio Tegiacchi, Mario Chiruzzi, Benito Casu, Giangiacomo Torri
  • Patent number: 4421924
    Abstract: A synthetic route to ascorbic acid is provided in which a 3,5:4,6-protected derivative of gulonic acid is prepared from gulono-1,4-lactone. Oxidation of the derivative and hydrolysis of the resulting product affords 2-ketogulonic acid or ester thereof which can be readily converted to ascorbic acid by known methods.
    Type: Grant
    Filed: April 24, 1981
    Date of Patent: December 20, 1983
    Assignee: Pfizer Inc.
    Inventor: Thomas C. Crawford
  • Patent number: 4421930
    Abstract: A process for preparing a pumpable surface active product based on polyether acetic acid is described, wherein 1-10% water and an acid is added to a crude reaction mixture obtained by reacting in an alkaline medium an adduct of the formula RO--(C.sub.2 H.sub.4 O).sub.x H with a compound Hal--CH.sub.2 COOM, wherein R is a hydrophobic, aliphatic or aliphatic-aromatic residue, x is a number having an average value of 0.5-10, Hal is a halogen atom and M represents an alkali metal, the amount of acid added being such that a 10-percent aqueous solution of the product shows a pH of 4-7. Preferably about 7% of water is added and also it is preferred to add so much acid that a pH of about 5-6 is obtained.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: December 20, 1983
    Assignee: Chem-Y Fabriek van Chemische Produkten B.V.
    Inventors: Nicolaas A. I. van Paassen, Hermanus C. H. van Riel
  • Patent number: 4419258
    Abstract: Dialkyl glyoxylates useful as anionic surfactants are disclosed. The dialkyl glyoxylates are particularly effective in removing soils from fabrics under laundering conditions. Detergent compositions containing the dialkyl glyoxylates and detergency builders are disclosed.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: December 6, 1983
    Assignee: Monsanto Company
    Inventor: Marvin M. Crutchfield
  • 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: 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: 4387245
    Abstract: A process for preparing diacetoneketogulonic acid comprises oxidizing diacetonesorbose in two or more oxidizing steps using different oxidizing agents in each step. In preferred embodiments the first oxidation is done electrochemically or using air and the second oxidation is via hypochlorite treatment.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: June 7, 1983
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Rolf Wittmann, Willi Wintermeyer, Jurgen Butzke
  • Patent number: 4352760
    Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: October 5, 1982
    Assignee: The Upjohn Company
    Inventor: Kirk M. Maxey
  • Patent number: 4347379
    Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: August 31, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4326072
    Abstract: A method for the synthesis of L-gulonic acid by catalytically hydrogenating D-glucuronic acid utilizing a ruthenium-based catalyst.
    Type: Grant
    Filed: July 1, 1980
    Date of Patent: April 20, 1982
    Assignee: ICI Americas Inc.
    Inventors: Walter M. Kruse, Makram H. Meshreki
  • Patent number: 4298708
    Abstract: Novel compounds which are produced from aminated alkoxylated aliphatic alcohols and alkyl phenols are described. The compounds are formed by reacting the nitrogen atom with certain compounds to form hydroxyl, carboxyl or sulfonate terminated compounds susceptible to salt formation with Group 1a and 2a metals, particularly sodium and potassium, to increase the water solubility of the compound. These compounds, particularly the salts of these compounds, are useful surface active agents and are soluble in polar and non-polar solvents. The are useful as oil and fuel additives, anticorrosive agents, detergents, froth flotation and oil recovery chemicals, and certain metal salts of the compound are useful as isocyanurate catalysts.
    Type: Grant
    Filed: May 9, 1980
    Date of Patent: November 3, 1981
    Assignee: Texaco Development Corp.
    Inventors: Heinz Schulze, Robert L. Zimmerman, Carter G. Naylor
  • Patent number: 4294766
    Abstract: An improved process for the preparation of potassium ribonate and of ribonolactone, which is an interesting intermediate for the preparation of riboflavin (vitamin B.sub.2), starting from potassium arabonate. An aqueous potassium arabonate solution is epimerized by adding a water-soluble non-ionic organic solvent, after which the greater part of the non-epimerized potassium arabonate can be separated off in a crystalline form. The mother liquor, which essentially contains potassium ribonate in addition to a small amount of unconverted potassium arabonate, is greatly concentrated and cooled, whereupon pure potassium ribonate crystallizes out; the latter can be lactonized in the conventional manner.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: October 13, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfram Schmidt, Joachim Paust
  • Patent number: 4278517
    Abstract: A process for producing glycols by the catalytic oxidation of olefinic compounds which comprises contacting an olefinic compound with an organic selenoxide in an aqueous alkaline medium in the presence of a catalytic amount of octavalent osmium to form the corresponding glycol.
    Type: Grant
    Filed: June 26, 1980
    Date of Patent: July 14, 1981
    Assignee: Union Carbide Corporation
    Inventor: Anthony G. Abatjoglou
  • Patent number: 4263454
    Abstract: Lithium ribonate and lithium arabonate are novel compounds by means of which ribonic acid, required as an intermediate for the synthesis of riboflavin (vitamin B.sub.2), or its salts, can be prepared particularly advantageously. The great advantages of the synthesis of ribonic acid are that, surprisingly, mixtures of lithium ribonate and lithium arabonate in aqueous solution can be exceptionally successfully separated into their components be fractional crystallization, and that the desired lithium ribonate, which is the less soluble salt and crystallizes out first, can be isolated in a very pure form. The solution which remains and which in the main contains lithium arabonate can be inexpensively re-epimerized.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: April 21, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfram Schmidt, Joachim Paust
  • Patent number: 4242145
    Abstract: A process for the simultaneous production of fructose and of gluconic acid from glucose-fructose mixtures and/or from invert sugar by the selective oxidation of the glucose proportion, wherein oxygen and/or air, activated by noble metal catalysts, are utilized as the oxidizing agents; the oxidation is conducted in a pH range of about 8 to 10; and the oxidation is terminated after the formation of 1 equivalent of carboxylic acid per mole of glucose employed.The thus-obtained gluconic acid can subsequently be separated from the unchanged fructose in a simple way and practically quantitatively, and can be isolated as the salt.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: December 30, 1980
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Hans-Rudolf Muller, Werner Kundig, Alfred Hedinger
  • Patent number: 4235811
    Abstract: Novel compounds are produced from aminated alkoxylated aliphatic alcohols and alkyl phenols are described. The compound is formed by reacting the nitrogen atom with certain compounds to form hydroxyl, carboxyl or sulfonate terminated compounds susceptible to salt formation with Group 1a and 2a metals, particularly sodium and potassium, to increase the water solubility of the compound. These compounds, particularly the salts of these compounds, are useful surface active agents and are soluble in polar and non-polar solvents. They are useful as oil and fuel additives, anticorrosive agents, detergents, froth flotation and oil recovery chemicals, and certain metal salts of the compound are useful as isocyanurate catalysts.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: November 25, 1980
    Assignee: Texaco Development Corp.
    Inventors: Heinz Schulze, Robert L. Zimmerman, Carter G. Naylor
  • Patent number: 4223163
    Abstract: Improved process for making alcohol polyethoxylates with narrow polyethoxy chain distributions using approximately equimolar ratios of alcohol and alkali metal or alkali metal hydride catalyst. The products are useful in making improved carboxyalkylated alkyl polyether surfactants having specific narrow ranges of ethoxylation and containing less than about 6% fatty alcohol. Detergent compositions containing said alkyl carboxyalkylated polyether surfactants and having less than about 6% fatty alcohol by weight of said alkyl carboxyalkylated polyether surfactants. Processes of making said alkyl carboxyalkylated polyether surfactants.
    Type: Grant
    Filed: December 10, 1976
    Date of Patent: September 16, 1980
    Assignee: The Procter & Gamble Company
    Inventor: Haydee R. Guilloty
  • Patent number: 4214101
    Abstract: A process for preparing ether carboxylates which comprises contacting an ethoxylated alcohol or alkylphenol or an ethylene oxide/propylene oxide block copolymer, with oxygen, in the presence of a palladium catalyst, at a pH of from 8 to 13 and at a temperature of 50.degree. to 95.degree. C.
    Type: Grant
    Filed: April 13, 1978
    Date of Patent: July 22, 1980
    Assignee: Kao Soap Co., Ltd.
    Inventors: Bunji Miya, Akio Kimura
  • Patent number: 4192801
    Abstract: Disclosed are novel phosphorane intermediates of the formula ##STR1## wherein Z is phenyl or C.sub.1 -C.sub.6 alkyl. The intermediates are of use in preparing 2-penem-3-carboxylic acid compounds having potent antibacterial activity.
    Type: Grant
    Filed: November 16, 1978
    Date of Patent: March 11, 1980
    Assignee: Bristol-Myers Company
    Inventor: Yasutsugu Ueda
  • Patent number: 4179392
    Abstract: A novel class of biodegradable detergents having improved resistance to precipitation in hard water are the water-soluble ionic salts or nonionic esters or amides of alkanoic acids which are substituted by at least one group containing an electronegative atom, said substitution being attached to a carbon atom 2 to 5 positions from the carboxyl carbon. Gamma-substituted alkanoic acid derivatives are preferred.
    Type: Grant
    Filed: August 3, 1973
    Date of Patent: December 18, 1979
    Assignee: Mobil Oil Corporation
    Inventors: El-Ahmadi I. Heiba, Albert L. Williams
  • Patent number: 4156093
    Abstract: The process comprises the hot treatment at a temperature of 80.degree. to 160.degree. C. by an amount of 5 to 50% of 85% of phosphoric acid, of the residues resulting from the distillation of reaction media containing hemiacetal-esters under substantially anhydrous conditions. These reaction media are selected from among those resulting from the reaction of alcohols and glyoxylic acid and those resulting from the treatment of glyoxylic hemiacetal-esters with P.sub.2 O.sub.5.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: May 22, 1979
    Assignee: Hoechst France
    Inventor: Yani Christidis
  • Patent number: 4144226
    Abstract: Ether and acetal carboxylates useful as detergent builders to replace sodium tripolyphosphate (STP) in detergent formulations are known to the art. According to the present invention, new and novel polymeric acetal carboxylates are provided which are stable under laundry use conditions, but depolymerize in acid media, making the polymer fragments more readily biodegradable in waste streams.
    Type: Grant
    Filed: August 22, 1977
    Date of Patent: March 13, 1979
    Assignee: Monsanto Company
    Inventors: Marvin M. Crutchfield, Victor D. Papanu, Craig B. Warren