Patents Represented by Attorney Riggs T. Stewart
  • Patent number: 4560806
    Abstract: An improved transition metal-phosphine-amide hydroformylation catalyst is disclosed having a substantially increased solubility in non-polar organic solvents, thereby preventing migration of the catalyst into the glycol aldehyde product during the hydroformylation process and subsequent separation operations, greatly facilitating and improving the catalyst separation and recycle operations.
    Type: Grant
    Filed: April 5, 1984
    Date of Patent: December 24, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Stephen E. Jacobson
  • Patent number: 4559183
    Abstract: A carboxylic acid anhydride such as acetic anhydride, is prepared from a carboxylate ester or a hydrocarbyl ether in processes comprising the use of a halide, carbon monoxide and a Group VIII noble metal.
    Type: Grant
    Filed: August 27, 1984
    Date of Patent: December 17, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Colin Hewlett
  • Patent number: 4558026
    Abstract: The present invention relates to a novel tellurium catalyst and its preparation, and to a process for preparing oxirane compounds using the novel catalyst. Specifically, the invention relates to a novel catalyst in which tellurium is chemically bound to a solid aromatic-type resin and to the reaction of olefinic compounds with hydrogen peroxide in the presence of the bound tellurium catalyst to produce oxirane compounds.
    Type: Grant
    Filed: August 24, 1984
    Date of Patent: December 10, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: William F. Brill
  • Patent number: 4555501
    Abstract: A supported silver catalyst for the oxidation of ethylene to ethylene oxide with molecular oxygen is made by impregnating a support with a hydrocarbon solution of a silver salt of a neo-acid having 7 or more carbon atoms, substantially free of water and said neo-acid. Preferably, the hydrocarbon solvent is toluene, xylene, ethyl benzene, cyclohexane, or cumene. The impregnated support is dried and the silver is activated under conditions chosen to provide the optimum selectivity to ethylene oxide. Thereafter, the activated silver catalyst may be impregnated with an alkali metal solution sufficient to increase selectivity of the silver catalyst above its alkali-free state. The amount of alkali metal on the finished catalyst is the optimum for the particular support selected and preferably will be about 1-6.times.10.sup.-3 gew/kg of catalyst. The catalyst may also include additional promoters, such as the alkaline earth metals, preferably barium.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: November 26, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: William D. Armstrong
  • Patent number: 4551560
    Abstract: A process for the selective, thermally-induced hydrolysis of acetals to the corresponding aldehydes and alcohols is disclosed, involving heating and pressurizing a substantially acid-free acetal containing solution to effect the rapid hydrolysis of the acetals without significant harm to the remaining reaction system components, and removing the treated solution from the reaction zone as product.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: November 5, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil M. Rizkalla
  • Patent number: 4547588
    Abstract: A catalyst composition useful for the oxidation of unsaturated aldehydes, particularly the oxidation of methacrolein to produce methacrylic acid, comprises the combination of oxides of molybdenum, copper, phosphorus, antimony, and cesium and/or calcium and optionally may include one or more of the elements Ni, Zn, Ru, Rh, Pd, Pt, As, K, Rb, Sr, Ba, Cr, V, Nb, W, Mn, Re, and rare earth metals including La.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: October 15, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Sargis Khoobiar
  • Patent number: 4540811
    Abstract: A carboxylic acid esters, such as methyl propionate, is prepared by carbonylation of an olefin, such as ethylene, in the presence of an alcohol by the use of a molybdenum-nickel-alkali metal, a tungsten-nickel-alkali metal or a chromium nickel-alkali metal co-catalyst and in the presence of a halide.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: September 10, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil Rizkalla
  • Patent number: 4537871
    Abstract: A liquid-phase catalyst is represented by the formula X:T:Z:Q, wherein X is molybdenum, tungsten or chromium, T is nickel, X and T being in zero valent form or in the form of a halide, an oxide, a carboxylate of 1 to 20 carbon atoms, a carbonyl or an hydride; Z is a halide source which is hydrogen halide, halogen, or an alkyl halide wherein the alkyl group contains 1 to 20 carbon atoms, and Q is the alkali metal component and is in the form of an iodide, a bromide, a chloride or a carboxylate as defined for X and T, the molar ratio of X to T being 0.1-10:1, the molar ratio of X+T to Q being 0.1-10:1, and the molar ratio of Z to X+T being 0.01-0.1:1.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: August 27, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil Rizkalla
  • Patent number: 4535188
    Abstract: Isobutane in a C.sub.4 hydrocarbon feed stream is converted to methacrolein in an integrated two-step process. Isobutane is dehydrogenated in a first step to isobutylene, hydrogen, and by-products and the reaction effluent is passed directly into a second step where isobutylene is oxidized to methacrolein without significant oxidation of the hydrogen and by-products. Any normal butenes present are converted to butadiene. The methacrolein and by-products may be separated and the unreacted isobutylene and isobutane recycled to the first step. Alternatively, the effluent from the second step may be used as feed to a further oxidation step for conversion of methacrolein to methacrylic acid.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: August 13, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Sargis Khoobiar
  • Patent number: 4532365
    Abstract: Alkanes, particularly propane and isobutane are converted to unsaturated aldehydes, particularly acrolein and methacrolein in an integrated two-step process wherein the alkane is dehydrogenated in a first step to the corresponding olefin, hydrogen, and by-products and the reaction effluent is passed directly into a second step where the olefin is oxidized to the corresponding unsaturated aldehyde without significant oxidation of the hydrogen and by-products. The aldehydes and by-products may be separated and the unreacted olefin and alkane recycled to the first step. Alternatively, the effluent from the second step may be used as feed to a further oxidation step for conversion of the unsaturated aldehyde to the corresponding unsaturated acid.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: July 30, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Sargis Khoobiar
  • Patent number: 4524581
    Abstract: A process for the production of variable amounts of electric power from a syngas feedstock is disclosed. The process captures, stores and releases carbon monoxide by forming and dissociating a suitable organic molecule, i.e., an alkyl formate, and thereby exploits the natural stoichiometry of the coal conversion to greatest advantage.
    Type: Grant
    Filed: April 10, 1984
    Date of Patent: June 25, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventors: Ronald F. Cascone, C. Ashley Solomon
  • Patent number: 4523980
    Abstract: A process is disclosed for the recovery of high purity squaric acid from squarate containing solids from the electrochemical cyclization of carbon monoxide, involving contacting the squaric acid containing product with a two-phase mixture of strong, nonoxidizing aqueous acid and an immiscible organic solvent, followed by separating the solid, substantially pure squaric acid from the resulting three-phase mixture.
    Type: Grant
    Filed: August 31, 1984
    Date of Patent: June 18, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: James J. Barber
  • Patent number: 4519815
    Abstract: Liquids in natural gas pipelines are separated, accumulated and distributed in a system wherein the pipeline contents are introduced into a vertical separation zone, the separated gaseous components are withdrawn from the upper portion of the separation zone and reintroduced into the pipeline at a downstream point, a stream of liquid components is withdrawn from a bottom portion of the separation zone, excess liquid components are introduced into an accumulation zone having a gradually rising slope and extending from the bottom portion of the separation zone to the upper portion of the separation zone, and gas displaced by and disengaged from the liquid in the accumulation zone is introduced into the upper portion of the separation zone, while the liquid is withdrawn and removed at a predetermined rate.
    Type: Grant
    Filed: December 15, 1983
    Date of Patent: May 28, 1985
    Assignee: Texas Eastern Engineering Ltd.
    Inventors: Ronald L. Buls, James P. Gilcrease
  • Patent number: 4519875
    Abstract: Ethylene glycol is purified, particularly for fiber-grade applications, by removal of the residual ethylene carbonate from which the glycol was derived. The effluent from a reactor in which ethylene carbonate is hydrolyzed to ethylene glycol is distilled to produce a lower-boiling fraction comprising substantially ethylene glycol and water and a higher-boiling fraction comprising substantially ethylene glycol, higher glycols, and concentrated in hydrolysis catalyst. The higher-boiling fraction is recirculated to reflux against the lower-boiling product, thereby essentially completing the hydrolysis of unreacted ethylene carbonate thereby reducing the ethylene carbonate content of the ethylene glycol to very low levels suitable for fiber-grade applications.
    Type: Grant
    Filed: May 9, 1984
    Date of Patent: May 28, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventors: Mitchell Becker, Howard M. Sachs
  • Patent number: 4517062
    Abstract: A process for the formation of glycols, particularly ethylene glycol through the electrochemical coupling of aldehydes such as formaldehyde in neutral or acidic solutions producing high yields and product selectivities is disclosed. The process can also be effectively operated in the presence of a wide variety of polar, miscible, organic cosolvents.
    Type: Grant
    Filed: November 3, 1983
    Date of Patent: May 14, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: James J. Barber
  • Patent number: 4508927
    Abstract: A process for preparation of glycols in which the vapor remaining after the partial condensation of a conventional ethylene oxide stripper overhead vapor stream is contacted with an aqueous solution of ethylene carbonate to recover ethylene oxide. No water need be removed from the enriched ethylene carbonate stream. Carbon dioxide is added and ethylene carbonate is formed by reaction at about 50.degree. to 200.degree. C. and 5 to 150 kg/cm.sup.2 gauge in the presence of a suitable catalyst, preferably about 0.5-20 wt % of an organic phosphonium halide. After stripping off unreacted components, the ethylene carbonate is hydrolyzed to glycols in the presence of the same carbonation catalyst and at temperatures in the range of about 100.degree. to 200.degree. C. and pressures of about 5 to 150 kg/cm.sup.2 gauge. Optionally, ethylene oxide and ethylene carbonate may be co-produced.
    Type: Grant
    Filed: August 2, 1983
    Date of Patent: April 2, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventors: Vijay S. Bhise, Harold Gilman
  • Patent number: 4503247
    Abstract: A catalyst composition useful for the oxidation of unsaturated aldehydes, particularly the oxidation of methacrolein to produce methacrylic acid, comprises the combination of oxides of molybdenum, copper, phosphorus, antimony, cesium and rhenium in predetermined relative atomic ratios.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: March 5, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Sargis Khoobiar
  • Patent number: 4497967
    Abstract: An integrated process for the preparation of ethanol from methanol, carbon monoxide and hydrogen feedstock is disclosed; the process featuring the steps of esterifying methanol and acetic acid to form methyl acetate; carbonylating the methyl acetate to form acetic anhydride; esterifying acetic anhydride with a lower aliphatic alcohol in an anhydrous zone to form the corresponding aliphatic acetate; hydrogenating the aliphatic acetate in a second anhydrous zone to form ethanol and the corresponding aliphatic alcohol; and separating the formed ethanol stream into an ethanol product stream and/or aliphatic alcohol recycle stream, which is recycled to react with acetic anhydride.
    Type: Grant
    Filed: June 15, 1984
    Date of Patent: February 5, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Chee-Gen Wan
  • Patent number: 4496781
    Abstract: A process for the preparation and purification of a glycol aldehyde intermediate which is later hydrogenated to ethylene glycol is disclosed. The process proceeds via the catalytic reaction of formaldehyde, carbon monoxide and hydrogen and utilizes a novel class of lipophilic rhodium phosphine amide catalysts and an effective solvent mixture, which enables efficient catalyst separation and recycle without the loss of a substantial amount of the expensive catalyst.
    Type: Grant
    Filed: April 5, 1984
    Date of Patent: January 29, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventors: Stephen E. Jacobson, Chun F. Chueh
  • Patent number: RE32082
    Abstract: Isobutane is converted to methacrolein in an integrated two-step process wherein isobutane is dehydrogenated in a first step to isobutylene, hydrogen, and by-products and the reaction effluent is passed directly into a second step where isobutylene is oxidized to methacrolein without significant oxidation of the hydrogen and by-products. The methacrolein and by-products may be separated and the unreacted isobutylene and isobutane recycled to the first step. Alternatively, the effluent from the second step may be used as feed to a further oxidation step for conversion of methacrolein to methacrylic acid. In one embodiment, the hydrogen produced in the first step is oxidized using the excess oxygen from the second step under conditions selected to avoid loss of the C.sub.4 components. In an alternative embodiment, the unreacted isobutane and isobutylene are absorbed and separated from the remaining components before being recycled to the first step.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: February 11, 1986
    Assignee: The Halcon SD Group, Inc.
    Inventor: Sargis Khoobiar