Patents Assigned to Halcon International, Inc.
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Patent number: 4045419Abstract: Process for preparing unsaturated esters by reacting an olefin having an allylic hydrogen atom with an ester forming material in the presence of oxygen and a catalyst selected from the group consisting of mercury, selenium or tellurium. The unsaturated ester may be converted to a polyunsaturated compound by pyrolysis.Type: GrantFiled: November 29, 1974Date of Patent: August 30, 1977Assignee: Halcon International, Inc.Inventor: Charles N. Winnick
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Patent number: 4045500Abstract: Ethylene glycol is prepared in an oxidation zone by the reaction of ethylene, molecular oxygen, and water in the presence of an iodine source to produce a liquid reaction product which is separated into a lower-boiling portion, a glycol fraction and a higher-boiling portion and the higher-boiling portion is recycled to the oxidation zone together with part of the lower-boiling portion.Type: GrantFiled: May 28, 1976Date of Patent: August 30, 1977Assignee: Halcon International, Inc.Inventors: Olav T. Onsager, Peter L. Szecsi
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Patent number: 4045294Abstract: Ethylene glycol or 1,2-propylene glycol contained in mixtures with lower carboxylate esters of the glycol is recovered by azeotropic distillation of the mixtures with an azeotroping agent which is a hydrocarbon which has a boiling point at atmospheric pressure above 190.degree. C but at most about 220.degree. C and is free from linear secondary and tertiary hydrogen atoms.Type: GrantFiled: September 12, 1975Date of Patent: August 30, 1977Assignee: Halcon International, Inc.Inventors: Mitchell Becker, Jon R. Valbert
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Patent number: 4028195Abstract: Ethylene glycol or 1,2-propylene glycol contained in mixtures with lower carboxylate esters of the glycol are separated from such mixtures by fractional distillation of the mixtures with the addition to the lower portion of the distillation zone of aqueous formic acid and/or acetic acid.Type: GrantFiled: September 12, 1975Date of Patent: June 7, 1977Assignee: Halcon International, Inc.Inventors: Mitchell Becker, Charles C. Yang
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Patent number: 4021311Abstract: Ethylene glycol or 1,2-propylene glycol contained in mixtures with lower carboxylate esters of the glycol is recovered by azeotropic distillation of the mixtures with 1,2,3-trimethyl benzene.Type: GrantFiled: September 12, 1975Date of Patent: May 3, 1977Assignee: Halcon International, Inc.Inventor: Mitchell Becker
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Patent number: 4021453Abstract: Olefins are oxidized to produce the corresponding epoxides by means of an aryl thallic carboxylate in the presence of an inert polar organic solvent and in the presence of water, the novel compound thallic benzoate being a preferred reactant.Type: GrantFiled: April 23, 1976Date of Patent: May 3, 1977Assignee: Halcon International, Inc.Inventor: William F. Brill
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Patent number: 4002678Abstract: 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, carbon monoxide and a nickel-chromium catalyst in the presence of a promoter comprising an organo-nitrogen compound or an organo-phosphorus compound wherein the nitrogen and phosphorus are trivalent.Type: GrantFiled: December 22, 1975Date of Patent: January 11, 1977Assignee: Halcon International, Inc.Inventors: Anthony N. Naglieri, Nabil Rizkalla
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Patent number: 4002677Abstract: 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, carbon monoxide and a nickel-chromium catalyst in the presence of a tin promoter.Type: GrantFiled: December 22, 1975Date of Patent: January 11, 1977Assignee: Halcon International, Inc.Inventors: Anthony N. Naglieri, Nabil Rizkalla
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Patent number: 3985795Abstract: Glycol esters of an olefin are prepared by contacting an olefin and a molecular oxygen containing gas in a carboxylic acid medium in the presence of a catalyst. Selectivities to the desired glycol esters are improved by treating the viscous residue and the precursor light components separated from the oxidation effluent by contacting them with water. In a preferred embodiment both residue and precursor light components streams are fed to the same zone wherein they are converted to additional glycol.Type: GrantFiled: December 30, 1974Date of Patent: October 12, 1976Assignee: Halcon International, Inc.Inventor: John Kollar
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Patent number: 3968175Abstract: A polyhydric compound is produced by catalytically disproportionating a precursor which is a lower carboxylate ester of said compound containing at least one lower carboxylate group and at least one free hydroxyl group. Most preferably the invention relates to the production of a diol by the catalytic disproportionation of a lower carboxylate diester of the diol.Type: GrantFiled: November 29, 1974Date of Patent: July 6, 1976Assignee: Halcon International, Inc.Inventor: John Kollar
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Patent number: 3968174Abstract: A polyhydric compound is produced by catalytically disproportionating a precursor which is a lower carboxylate ester of said compound containing at least one lower carboxylate group and at least one free hydroxyl group. Most preferably the invention relates to the production of a diol by the catalylic disproportionation of a lower carboxylate diester of the diol.Type: GrantFiled: November 29, 1974Date of Patent: July 6, 1976Assignee: Halcon International, Inc.Inventor: John Kollar
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Patent number: 3964980Abstract: The conventional process for the recovery of ethylene oxide produced by the silver catalyzed, vapor phase, partial oxidation of ethylene with molecular oxygen involves a sequence of steps including absorption in water of the ethylene oxide contained in the reaction effluent. The ethylene oxide-containing absorbate is then stripped and the vapor thus generated is subjected to reabsorption, also in water. This invention provides an improved stripper-reabsorption system and includes the steps of partial condensation of the stripper overhead and introduction of an additional absorbent stream into the readsorption step.Type: GrantFiled: March 24, 1975Date of Patent: June 22, 1976Assignee: Halcon International, Inc.Inventor: Brian I. Ozero
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Patent number: 3960954Abstract: Oximes and hydroxylamines are prepared by reacting a primary amine, the amino group of which is attached to a primary or secondary carbon atom, with an organic hydroperoxide in the presence of a catalytic amount of a compound of Ti, V, Cr, Se, Zr, Nb, Mo, Te, Ta, W, Re, or U.Type: GrantFiled: May 11, 1970Date of Patent: June 1, 1976Assignee: Halcon International, Inc.Inventors: Joseph Lee Russell, John Kollar
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Patent number: 3956358Abstract: Derivatives of the .alpha.,.beta.-unsaturated carboxylic acids are dimerized by reaction in the presence of a catalyst consisting essentially of (a) at least one metal compound of the formula M(X).sub.n wherein M is zinc, aluminum, titanium, vanadium, iron, or cobalt, X is a halide and n is a number equal to the valence of the metal M and (b) at least one nitrogen-containing Lewis Base which is (1) a tertiary monoaryl amine of the formula, ##EQU1## wherein R.sup.1 and R.sup.2 are the same or different and each is an alkyl group or a cycloalkyl group with at least one of R.sup.1 and R.sup.2 containing at least two carbon atoms; or (2) a tertiary monobenzyl amine of the formula, ##EQU2## wherein R.sup.3 and R.sup.Type: GrantFiled: December 30, 1974Date of Patent: May 11, 1976Assignee: Halcon International, Inc.Inventor: Olav Torgeir Onsager
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Patent number: 3954831Abstract: Acrylonitrile is dimerized by reaction in the presence of a catalyst consisting essentially of (a) at least one metal compound of the formula M(X).sub.n wherein M is Zn or Co, X is an anion derived from an alkyl or aryl sulfonic acid or from a carboxylic acid containing at least two carbon atoms which is substituted by at least one of the groups, --F, --Cl, --Br, --I and --CN in the .alpha.-C-position relative to the acid group and n is a number equal to the valence of the metal M divided by the number of acid equivalents of X and (b) at least one nitrogen-containing Lewis Base which is (1) a tertiary monoamine of the formula ##EQU1## wherein R.sup.1, R.sup.2, and R.sup.Type: GrantFiled: December 30, 1974Date of Patent: May 4, 1976Assignee: Halcon International, Inc.Inventor: Olav Torgeir Onsager
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Patent number: 3950370Abstract: Acrylonitrile is dimerized by reaction in the presence of a catalyst consisting essentially of (a) at least one metal compound of the formula M(X).sub.n wherein M is magnesium, chromium or manganese, X is a halide and n is a number equal to the valence of the metal M and (b) at least one nitrogen-containing Lewis Base which is (1) a tertiary monoamine of the formula ##EQU1## wherein R.sup.1, R.sup.2, and R.sup.Type: GrantFiled: December 30, 1974Date of Patent: April 13, 1976Assignee: Halcon International, Inc.Inventor: Olav Torgeir Onsager
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Patent number: 3947501Abstract: The acidic catalyst characteristics of a reaction mixture resulting from a catalytic epoxidation are reduced whereby dehydration of by-product alcohol is suppressed during subsequent work-up procedures. This reduction is effected by catalytic hydrogenation, chemical reduction or the addition of a basic material.Type: GrantFiled: April 5, 1974Date of Patent: March 30, 1976Assignee: Halcon International, Inc.Inventor: John Kollar
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Patent number: 3947500Abstract: The present invention is concerned with the treatment of reaction mixtures which result from the metal catalyzed epoxidation of olefinically unsaturated compounds to the corresponding oxirane compound using organic hydroperoxides.Type: GrantFiled: April 5, 1974Date of Patent: March 30, 1976Assignee: Halcon International, Inc.Inventor: John Kollar
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Patent number: 3947474Abstract: A catalyst useful for the oxidation of organic compounds, particularly vapor-phase oxidation of benzene with molecular oxygen to produce maleic anhydride, comprises the oxides of molybdenum, vanadium, phosphorus, sodium and boron in combination with an oxide of at least one metal of the group consisting of manganese, tin, tungsten and bismuth, and preferably also in combination with an oxide of at least one member of the group consisting of iron, cobalt and nickel.Type: GrantFiled: January 15, 1974Date of Patent: March 30, 1976Assignee: Halcon International, Inc.Inventor: Robert S. Barker
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Patent number: 3932513Abstract: The present invention relates to the oxidation of cyclohexane with molecular oxygen in a series of reaction zones, with vaporization of cyclohexane from the last reactor effluent and parallel distribution of this cyclohexane vapor among the series of reaction zones.Type: GrantFiled: February 22, 1973Date of Patent: January 13, 1976Assignee: Halcon International, Inc.Inventor: Joseph L. Russell