Patents Represented by Attorney Harold N. Wells
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Patent number: 4537871Abstract: 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: GrantFiled: April 23, 1984Date of Patent: August 27, 1985Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla
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Patent number: 4535188Abstract: 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: GrantFiled: September 20, 1982Date of Patent: August 13, 1985Assignee: The Halcon SD Group, Inc.Inventor: Sargis Khoobiar
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Patent number: 4532365Abstract: 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: GrantFiled: February 22, 1983Date of Patent: July 30, 1985Assignee: The Halcon SD Group, Inc.Inventor: Sargis Khoobiar
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Patent number: 4519815Abstract: 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: GrantFiled: December 15, 1983Date of Patent: May 28, 1985Assignee: Texas Eastern Engineering Ltd.Inventors: Ronald L. Buls, James P. Gilcrease
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Patent number: 4519875Abstract: 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: GrantFiled: May 9, 1984Date of Patent: May 28, 1985Assignee: The Halcon SD Group, Inc.Inventors: Mitchell Becker, Howard M. Sachs
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Patent number: 4508927Abstract: 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: GrantFiled: August 2, 1983Date of Patent: April 2, 1985Assignee: The Halcon SD Group, Inc.Inventors: Vijay S. Bhise, Harold Gilman
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Patent number: 4503247Abstract: 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: GrantFiled: July 6, 1982Date of Patent: March 5, 1985Assignee: The Halcon SD Group, Inc.Inventor: Sargis Khoobiar
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Patent number: 4483803Abstract: A carboxylic acid anhydride, such as propionic anhydride, is prepared from an olefin and a carboxylic acid in carbonylation processes comprising the use of a halide, carbon monoxide and a molybdenum-nickel-alkali metal, a tungsten-nickel-alkali metal or a chromium-nickel-alkali metal component.Type: GrantFiled: September 30, 1982Date of Patent: November 20, 1984Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla
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Patent number: 4483804Abstract: A carboxylic acid anhydride, such as acetic anhydride, is prepared from a carboxylate ester or a hydrocarbyl ether in carbonylation processes comprising the use of an iodide or bromide carbon monoxide and a molybdenum-nickel-alkali metal or a tungsten-nickel-alkali metal catalyst.Type: GrantFiled: September 30, 1982Date of Patent: November 20, 1984Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla
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Patent number: 4482497Abstract: A carboxylic acid, such as acetic acid, is prepared by carbonylation of a hydrocarbyl alcohol, such as methanol by the use of a molybdenum-nickel-alkali metal or a tungsten-nickel-alkali metal co-catalyst in the presence of an iodide or bromide.Type: GrantFiled: September 30, 1982Date of Patent: November 13, 1984Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla
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Patent number: 4480113Abstract: 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: GrantFiled: September 28, 1982Date of Patent: October 30, 1984Assignee: The Halcon SD Group, Inc.Inventor: William F. Brill
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Patent number: 4479013Abstract: A catalyst composition useful for the oxidation of olefins, particularly the vapor phase oxidation of isobutylene and/or tertiary butyl alcohol to produce methacrolein, consists essentially of the combination of oxides of molybdenum, cobalt, iron, bismuth, thallium, antimony, silicon, and nickel, along with one or more members of the groups consisting of the alkali metals, the alkaline earth metals, the rare earth metals including lanthanum, tungsten, and mixtures thereof. The catalyst has a BET surface area within the range of about 0.5-10 m.sup.2 /gm and preferably within the range of about 2-6 m.sup.2 /gm. Preferably, the catalyst has no more than about 3% of the surface area associated with pores smaller than about 100 .ANG.. The catalyst is heated during its preparation to a temperature above 525.degree. C., preferably above 550.degree. C., most preferably to about 600.degree. C.Type: GrantFiled: July 9, 1982Date of Patent: October 23, 1984Assignee: The Halcon SD Group, Inc.Inventor: Sargis Khoobiar
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Patent number: 4476238Abstract: Tarry residues often are formed in carbonylation reactions, such as those in which esters or ethers are carbonylated to produce ethylidene diacetate or carboxylic acid anhydrides, such as acetic anhydride. Such residues contain Group VIII noble metal catalysts, typically rhodium, which must be separated before the residues can be disposed of. In the process of the invention, the residues are extracted with solvents which preferentially dissolve the tars. Preferred solvents include alkanes, cycloalkanes, halogenated alkanes, and aromatic hydrocarbons, particularly cyclohexane, carbon tetrachloride, and toluene. Separation of the residues from the noble metal catalyst by solvent extraction makes possible the disposal of the residues and the return of the noble metals to the reaction for reuse.Type: GrantFiled: May 28, 1981Date of Patent: October 9, 1984Assignee: The Halcon SD Group, Inc.Inventors: Burton J. Palmer, Joseph V. Posluszny
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Patent number: 4476237Abstract: Tarry residues often are formed in carbonylation reactions, such as those in which esters or ethers are carbonylated to produce ethylidene diacetate or carboxylic acid anhydrides, such as acetic anhydride. Such residues contain Group VIII noble metal catalysts, typically rhodium, which must be separated before the residues can be disposed of. In the process of the invention, a portion of the carbonylation reaction mixture is flashed to a lower pressure and the resulting residues-containing liquid is extracted with solvents which preferentially remove the tars. The tars are separated from the solvents and disposed of while the solvents are recycled for further use. The catalyst-containing liquid is processed to remove residual solvent and returned to the carbonylation reaction.Type: GrantFiled: May 28, 1981Date of Patent: October 9, 1984Assignee: The Halcon SD Group, Inc.Inventor: Richard V. Porcelli
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Patent number: 4462978Abstract: Hydrogen peroxide is produced in a reaction between carbon monoxide, oxygen, and water in the presence of a solvent using a Group 8 noble metal as a catalyst. Especially preferred as the working solution is palladium chloride in acetone.Type: GrantFiled: December 10, 1982Date of Patent: July 31, 1984Assignee: The Halcon SD Group, Inc.Inventor: William F. Brill
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Patent number: 4454346Abstract: 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 in predetermined relative atomic ratios.Type: GrantFiled: March 27, 1981Date of Patent: June 12, 1984Assignee: The Halcon SD Group, Inc.Inventor: Sargis Khoobiar
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Patent number: 4437938Abstract: Ethylene oxide is recovered from aqueous solutions by extracting with carbon dioxide in the near-critical or super-critical state, thereby selectively removing the ethylene oxide from water, and thereafter recovering ethylene oxide from the carbon dioxide by distillation or other suitable means.Type: GrantFiled: July 17, 1981Date of Patent: March 20, 1984Assignee: The Halcon SD Group, Inc.Inventors: Vijay S. Bhise, Robert Hoch
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Patent number: 4437939Abstract: Ethylene oxide is extracted from aqueous solutions by carbon dioxide under (near) super-critical conditions and thereafter recovered by distillation at sub-critical conditions. Improved distillation is obtained by adding to the carbon dixoide a gas (or gases) which adjust the critical temperature of the gas mixture of the top of the distillation column within the range of about 32.degree. C. to about 75.degree. C. Preferred gases are the saturated hydrocarbons, particularly propane, n-butane, isobutane and pentane.Type: GrantFiled: November 16, 1981Date of Patent: March 20, 1984Assignee: The Halcon SD Group, Inc.Inventors: Vijay S. Bhise, Robert Hoch
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Patent number: 4434240Abstract: Heavy residues produced by noble metal catalyzed carbonylation reactions and containing Group VIII noble metals, particularly rhodium, are treated with reagents to precipitate solids containing substantially all of the noble metal contained in the residues. The solids may be further treated to recover the noble metals or they may be returned directly for reuse in the carbonylation reaction. Suitable reagents include alkali metal hydroxides, alkali metal peroxides, alkali metal borohydrides, and other reducing agents, such as formaldehyde and acidified sodium bisulfite.Type: GrantFiled: November 16, 1981Date of Patent: February 28, 1984Assignee: The Halcon SD Group, Inc.Inventor: Joseph Pugach
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Patent number: 4413147Abstract: 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: GrantFiled: April 14, 1982Date of Patent: November 1, 1983Assignee: The Halcon SD Group, Inc.Inventor: Sargis Khoobiar