Patents Represented by Attorney Carl G. Ries
  • Patent number: 5139622
    Abstract: An extractive distillation agent consisting essentially of triethylene glycol is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide contaminated with reduced quantities of acetone and methanol, and a heavier bottoms distillation fraction containing substantially all of the triethylene glycol, water and acetone and some of the methanol introduced into the distillation column.
    Type: Grant
    Filed: October 3, 1991
    Date of Patent: August 18, 1992
    Assignee: Texaco Chemical Company
    Inventors: Edward T. Marquis, George P. Speranza, Yu-Hwa E. Sheu, William K. Culbreth, III, David G. Pottratz
  • Patent number: 5138097
    Abstract: Liquid amine terminated polyamide addition products having an average molecular weight of about 3,000 to about 10,000 are prepared by the non-catalytic reaction of a dicarboxylic acid having a molecular weight within the range of about 130 to about 700 with a higher molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 1,500 to about 6,000 and with a lower molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 200 to about 700, the reaction conditions including a temperature within the range of about 150.degree. to about 280.degree. C., a pressure of about 0.1 to 20 atmospheres and a reaction time of about 2 to about 5 hours.
    Type: Grant
    Filed: February 22, 1991
    Date of Patent: August 11, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Wei-Yang Su
  • Patent number: 5136035
    Abstract: 4-Alkyl-2-morpholinones are prepared by bringing an N-alkyldiethanolamine into contact with a zinc oxide promoted copper catalyst in the presence of hydrogen under reaction conditions including a temperature within the range of about 240.degree. to about 400.degree. C. and a pressure within the range of about 0 to about 300 psig and by recovering the 4-alkyl-2-morpholinone that is formed by the reaction.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: August 4, 1992
    Assignee: Texaco Chemical Company
    Inventor: Wei-Yang Su
  • Patent number: 5130382
    Abstract: Hydroxy terminated polyamides are prepared having the formula: ##STR1## wherein R represents a defined hydrocarbon group,R' and R" represents defined oxypropylene groups, and R'" represents a defined oxyethylene group,the hydroxy terminated polyamide having been prepared by first preparing an intermediate dicarboxylic acid terminated polyoxypropylene polyamide by reacting an excess of a dicarboxylic acid component with a diamine mixture composed of a higher molecular weight polyoxypropylene diamine and a lower molecular weight polyoxypropylene diamine, and by reacting the intermediate polyamide with a molar excess of an oxyethylene amino alcohol.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 14, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Wei-Yang Su
  • Patent number: 5128441
    Abstract: A block polyamido primary amine condensation product prepared by reacting a defined polyoxyalkylene polyamine having terminal primary amine groups with an amount of a defined dicarboxylic acid or an anhydride or a C.sub.1 to C.sub.4 alkyl ester thereof, sufficient to react one mole of the dicarboxylic acid reactant with each primary amine group of the polyoxyalkylene polyamine to thereby prepare an intermediate condensation reaction product containing terminal carboxyl groups, and reacting one mole of a defined organic di-primary amine with each terminal carboxyl group of the said intermediate condensation reaction product to thereby provide, as the principal product of the reaction a block polyamido primary amine condensation product.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: July 7, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5127997
    Abstract: Purified propylene oxide is recovered from an impure propylene oxide feedstock contaminated with more than 50 ppm of six carbon atom hydrocarbon impurities by a solvent extraction process wherein:an impure propylene oxide feedstock is charged to a liquid/liquid extraction zone and contacted therein with an extractant consisting essentially of water and a paraffinic hydrocarbon containing 8 to 10 carbon atoms, and resolved therein into a raffinate consisting essentially of an aqueous solution of propylene oxide and into an extract comprising the paraffinic hydrocarbon and the 6 carbon atom impurities initially present in the propylene oxide feedstock.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: July 7, 1992
    Assignee: Texaco Chemical Company
    Inventors: William A. Smith, Robert A. Meyer, Eileen T. Nguyen
  • Patent number: 5128492
    Abstract: An epoxidation reaction product formed by the molybdenum catalyzed reaction of propylene with tertiary butyl hydroperoxide to provide propylene oxide and tertiary butyl alcohol is separated by distillation into a propylene fraction, a propylene oxide fraction, a tertiary butyl alcohol fraction and a heavy liquid distillation fraction composed primarily of tertiary butyl hydroperoxide, tertiary butyl alcohol, dissolved molybdenum catalyst, and impurities including lower aliphatic C.sub.1 -C.sub.4 carboxylic acids, and the heavy liquid distillation fraction is saturated with hydrogen to precipitate the molybdenum therefrom for recovery.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: July 7, 1992
    Assignee: Texaco Chemical Company
    Inventors: William A. Smith, Robert A. Meyer, Edward T. Marquis
  • Patent number: 5120879
    Abstract: Polyoxypropylene diketones are prepared by initially adding predetermined amounts of a mono- or dicarboxylic acid having a pK<4.5 and a water solubility at 25.degree. C. of >1%, a polyoxypropylene glycol and, optionally, water, to a reaction zone and thereafter adding an aqueous solution of an alkali metal or an alkaline earth metal hypochlorite oxidant to the reaction zone with agitation under reaction conditions including a temperature of about 10.degree. to about 50.degree. C., a pressure of about 0 to 1,000 psig. and a total reaction time of about 0.5 to 20 hours, whereby said polyoxypropylene glycol will be substantially selectively converted to the said corresponding diketone, and recovering said diketone.
    Type: Grant
    Filed: May 30, 1991
    Date of Patent: June 9, 1992
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 5116467
    Abstract: An extractive distillation agent consisting essentially of sulfolane is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide, and a heavier bottoms distillation fraction containing substantially all of the sulfolane and water introduced into the distillation column.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: May 26, 1992
    Assignee: Texaco Chemical Company
    Inventors: Edward T. Marquis, George P. Speranza, Yu-Hwa E. Sheu, William K. Culbreth, III, David G. Pottratz
  • Patent number: 5116465
    Abstract: An extractive distillation agent consisting essentially of 2-hydroxyethyl 2-hydroxyethylcarbamate, and is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide, and a heavier bottoms distillation fraction containing substantially all of the 2-hydroxyethyl 2-hydroxyethycarbamate, and water introduced into the disillation column.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: May 26, 1992
    Assignee: Texaco Chemical Company
    Inventors: Ernest L. Yeakey, Edward T. Marquis
  • Patent number: 5107067
    Abstract: Complexes made by reacting an ammonium-containing molybdenum compound with an alkylene glycol in the presence of water at an elevated temperature are described. Mild stripping of the water subsequent to complex formation is preferred. If some of the water is left in the complex, it may serve as an excellent olefin epoxidation catalyst. The ratio of moles of alkylene glycol to gram atoms of molybdenum in the complex forming reaction ranges from 7:1 to 20:1. Ethylene glycol and propylene glycol are the particularly preferred alkylene glycols.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: April 21, 1992
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, Kenneth P. Keating, John R. Sanderson, William A. Smith
  • Patent number: 5106458
    Abstract: Methyl formate is removed from impure propylene oxide by contacting the impure propylene oxide in a treating zone with a basic ion exchange resin for a period of time sufficient to convert the methyl formate to formic acid and methanol, and by withdrawing a substantially methyl formate-free treated propylene oxide product from the treating zone.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: April 21, 1992
    Assignee: Texaco Chemical Company
    Inventors: Robert A. Meyer, Eileen T. Nguyen, William A. Smith
  • Patent number: 5103062
    Abstract: In accordance with the process of the present invention normally liquid, water-soluble poly(oxyethylene/oxypropylene) polyamine products are prepared using an initiator, which may contain oxyethylene groups. In a series of alkoxylation reaction steps the initiator is reacted with predetermined weight percentages of ethylene oxide and propylene oxide, said process comprising the steps of:a. Charging a predetermined percentage of initiator to an alkoxylation reaction zone,b. Alkoxylating said initiator therein with predetermined percentages of ethylene oxide and propylene oxide to provide an intermediate polyol,c. Propoxylating said intermediate polyol with a predetermined percentage of propylene oxide to provide a normally liquid, water-soluble precursor polyol, andd.
    Type: Grant
    Filed: April 10, 1987
    Date of Patent: April 7, 1992
    Assignee: Texaco Inc.
    Inventors: Michael Cuscurida, Ernest L. Yeakey
  • Patent number: 5101052
    Abstract: An epoxidation reaction product formed by the molybdenum catalyzed reaction of propylene with tertiary butyl hydroperoxide to provide propylene oxide and tertiary butyl alcohol is separated by distillation into a propylene fraction, a propylene oxide fraction, a tertiary butyl alcohol fraction and a heavy liquid distillation fraction composed primarily of tertiary butyl hydroperoxide, tertiary butyl alcohol, dissolved molybdenum catalyst, and impurities including lower aliphatic C.sub.1 -C.sub.4 carboxylic acids, and the heavy liquid distillation fraction is saturated with ammonia to precipitate the molybdenum therefrom for recovery.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: March 31, 1992
    Assignee: Texaco Chemical Company
    Inventors: Robert A. Meyer, Edward T. Marquis
  • Patent number: 5101060
    Abstract: Normally liquid final Mannich condensates prepared by reacting a para C.sub.1 -C.sub.15 alkyl phenol with formaldehyde and a first polyoxyalkylene diamine to form an intermediate Mannich condensate that is reacted with formaldehyde and a second polyoxyalkylene diamine to form a final Mannich condensate, the first and second polyoxyalkylene diamines having the formula: ##STR1## wherein R represents hydrogen or methyl and R' represents an alkyl group containing 1 to 4 carbon atoms or cyanoethyl group, and n represents positive numbers having a value of 1 to about 6, the final Mannich condensate having the formula: ##STR2## wherein X and Y are polyoxyalkylene amine groups derived from the first and second polyoxyalkylene diamines and formaldehyde.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: March 31, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5098986
    Abstract: Normally liquid polyfunctional final Mannich condensates that are useful as curing agents for epoxy resins are prepared by reacting a para C.sub.1 -C.sub.15 alkyl phenol with formaldehyde and a first polyoxyalkylene diamine to form an intermediate Mannich condensate that is reacted, in turn, with formaldehyde and a second polyoxyalkylene diamine to form the final Mannich condensate, the first polyoxyalkylene diamine having the formula: ##STR1## wherein: n represents a positive number having a value of 1 to about 6, andR' independently represents hydrogen or a methyl group, the second polyoxyalkylene diamine having the formula: ##STR2## wherein n and n' represent positive numbers having a value of 1 to about 6,R' independently represents hydrogen or a methyl group, andR"' represents an alkyl group containing 1 to 4 carbon atoms or a cyanoethyl group.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: March 24, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5099073
    Abstract: A process for the conversion of a polyoxypropylene glycol to the corresponding diketone derivative by dehydrogenation in the presence of an unsupported nickel, copper, chromia catalyst or a Raney nickel catalyst.
    Type: Grant
    Filed: February 11, 1991
    Date of Patent: March 24, 1992
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, John M. Larkin
  • Patent number: 5095116
    Abstract: A block amido-amine condensation product having the formula: ##STR1## wherein R' represents hydrogen or methyl, andR" represents an organic group selected from the group consisting of polyoxyethylene groups, polyoxypropylene groups, polyoxyethylene/oxypropylene groups, and polyethylene amino groups.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: March 10, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5093382
    Abstract: Foamed reaction products of organic polyisocyanates containing an average of at least 2 isocyanate groups per molecule with equivalent weights of carbon dioxide-generating, carboxyl group terminated addition reaction products of a polyoxyalkylene polyamine or polyoxyalkylene polyol reactant with a polycarboxylic acid reactant,the polyoxyalkylamine and polyoxyalkyl polyol reactant having an average molecular weight of about 200 to about 5,000 and being selected from the group consisting of polyoxypropylene diamines, polyoxypropylene/oxyethylene diamines, poly(oxytetramethylene) diamines and polyoxypropylene triamines, polyoxypropylene diols, polyoxypropylene/oxyethylene diols, poly(oxytetramethylene) diols and polyoxypropylene triols,the polycarboxylic acid reactant containing 2 to about 45 carbon atoms and being selected from the group consisting of aromatic and aliphatic dicarboxylic acids and anhydrides thereof.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: March 3, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Donald H. Champion
  • Patent number: 5093506
    Abstract: The distillation product fraction obtained from an isobutane oxidation reaction product after the removal of unreacted isobutane will contain tertiary butyl hydroperoxide, tertiary butyl alcohol and carboxylic acid contaminants such as formic acid, acetic acid and isobutyric acid. It has been discovered that when the distillation product fraction is treated with about 1/2 to 1 equivalents of calcium oxide and/or calcium hydroxide based on the carboxylic acid content of the distillate product fraction, a portion of the carboxylic acid contaminants will precipitate thus partially purifying the distillation product fraction so that, thereafter, molybdenum precipitation will be substantially inhibited when the thus-treated distillation product fraction is used as a feedstock for an epoxidation reaction wherein tertiary butyl hydroperoxide is reacted with an olefin in the presence of a soluble molybdenum catalyst to provide an olefin epoxide and additional tertiary butyl hydroperoxide.
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: March 3, 1992
    Assignee: Texaco Chemical Company
    Inventors: Edward T. Marquis, John R. Sanderson, Robert A. Meyer