Preparing By Oxidation Utilizing Gaseous Oxygen Patents (Class 568/569)
  • Patent number: 5196597
    Abstract: The present invention relates to a process for the oxidation of isobutane in the liquid phase to produce TBA and TBHP wherein at least a portion of the oxidation product mixture is obtained from the condensate of vapors from the oxidation zone.
    Type: Grant
    Filed: April 22, 1992
    Date of Patent: March 23, 1993
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Robert N. Cochran, Shaw-Chan Lin
  • Patent number: 5196598
    Abstract: A process for producing a polyhydroperoxy aromatic compound by oxidation of an aromatic hydrocarbon, e.g., 4,4'-diisopropylbiphenyl and 4,4'-diisopropylnaphthalene, with molecular oxygen is disclosed, in which the oxidation is carried out in the presence of a metal ion selected from cobalt, nickel, zinc and lead ions. Even in using a reaction apparatus made of an iron-containing metal generally employed in industry, a high conversion of secondary alkyl groups can be reached, and the desired polyhydroperoxy aromatic compound can be obtained in a high yield.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: March 23, 1993
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki, Kimiko Kaneko
  • Patent number: 5149885
    Abstract: The present invention relates to the oxidation of isobutane to TBHP wherein the oxidation exothermic heat of reaction is removed by circulating a portion of the liquid reaction mixture through an indirect heat exchanger and comprises the further feature that the molecular oxygen necessary for the oxidation is introduced by means of sparging into the cooled, circulating liquid reaction mixture.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: September 22, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventor: John C. Jubin, Jr.
  • Patent number: 5095143
    Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Amoco Corporation
    Inventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
  • Patent number: 5043481
    Abstract: The present invention relates to the oxidation of a cycloalkane to produce a product comprised of cycloalkylhydroperoxide with the removal of a vapor stream from the oxidation zone wherein oxidation products such as hydroperoxide, cycloalkanol and cycloalkanone are separated from the removed stream before the stream is recycled to the oxidation zone.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: August 27, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventor: Robert Nedwick
  • Patent number: 5032688
    Abstract: A process for the preparation of aralkyl hydroperoxides having the formula (I) is described ##STR1## in which n=1, 2 or 3, Ar means a phenyl group which can be substituted with halogen or one or more branched or straight chain alkyl groups with 1 to 5 C-atoms, or a naphthyl group, and each radical R.sup.1 and R.sup.2 means a low alkyl radical, the alkyl radicals R.sup.1 and R.sup.2 together having 2 to 4 carbon atoms, by reaction of aralkyl carbinols having the formula (II) ##STR2## in which Ar, R.sup.1, R.sup.2 and n have the meaning given for formula (I), with hydrogen peroxide under acid conditions, the reaction being carried out in the presence of an acid-combining agent. An alkali sulphate, ammonium sulphate, alkali hydrogen sulphate and/or ammonium hydrogen sulphate is used in preference as the acid-combining agent. Tert.aralkyl hydroperoxides can be prepared in high yield with a high purity in a simple and safe manner with this process.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: July 16, 1991
    Assignee: Peroxid-Chemie GmbH
    Inventors: Maximilian Dorn, Eberhard Hagel, Werner Zeiss
  • Patent number: 5017729
    Abstract: Phenol is produced in a recycle manner by (a) reacting benzene with propylene to synthesize cumene, (b) oxidizing the cumene of step (a) into cumene hydroperoxide, (c) acid cleaving cumene hydroperoxide into phenol and acetone, (d) hydrogenating the acetone of step (c) into isopropanol, (e) dehydrating the isopropanol of step (d) into propylene, and (f) recycling the propylene of step (e) to step (a). It is also possible to take propylene from step (e). The acetone by-product produced upon preparation of phenol is converted into propylene which is useful by itself for any other uses or recycled to the phenol producing process.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: May 21, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hiroshi Fukuhara, Fujihisa Matsunaga
  • Patent number: 5003113
    Abstract: In a process of producing isopropylnaphthols by oxidizing diisopropylnaphthalenes with molecular oxygen in a liquid phase to provide a reaction mixture which contains therein diisopropylnaphthalene monohydroperoxides and then acid decomposing the monohydroperoxides to isopropylnaphthols, the improvement comprising separating an organic layer from the reaction mixture, adding lower aliphatic alcohols of 1-4 carbons to the organic layer, crystallizing the diisopropylnaphthalenes while allowing the diisopropylnaphthalene monohydroperoxides to remain dissolved in the lower aliphatic alcohols, thereby to separate the monohydroperoxides from the diisopropylnaphthalenes.A further improvement in the process comprises crystallizing the isopropylnaphthols from aromatic hydrocarbons of 6-12 carbons.
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: March 26, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Michio Tanaka, Masayasu Ishibashi, Katsuo Taniguchi
  • Patent number: 4996372
    Abstract: In a process for producing 2,6-dihydroxynaphthalene from 2,6-diisopropylnaphthalene, 2,6-diisopropylnaphthalene is oxidized in the presence of a specific proportion of a basic compound to hydroxylate or hydroperoxylate 2,6-diisopropylnaphthalene in a high conversion, and the resulting intermediate is then subjected to acid cleavage in the presence of hydrogen peroxide to produce 2,6-dihydroxynaphthalene in a high yield. The yield of 2,6-dihydroxynaphthalene increases by subjecting the reaction mixture containing the above intermediate to a purifying operation or dehydrating operation or adding acetone to it before it is submitted to the acid cleavage. 2,6-Dihydroxynaphthalene may be reacted with acetic anhydride to obtain 2,6-diacetoxynaphthalene.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: February 26, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Kenji Saeki, Hiroshi Fukuhara, Tokinori Agoo, Toru Taguchi, Hisaya Miki, Yutaka Haneda, Sadao Yoshimoto
  • Patent number: 4950794
    Abstract: The oxidation of ethylbenzene to products comprised of ethylbenzene hydroperoxide and acetophenone is modified in order to enhance acetophenone production by reducing the alkali content of the oxidation mixture below 0.1 ppm and by incorporation of 0.05 to 2 wt. % water in the oxidation mixture.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: August 21, 1990
    Assignee: Arco Chemical Technology, Inc.
    Inventors: Lawrence M. Candela, Robert N. Cochran, Scott H. Sandler
  • Patent number: 4584413
    Abstract: This invention relates to the purification of tertiary butyl hydroperoxide containing minor amounts of primary and secondary alkyl hydroperoxide contaminants obtained by the oxidation of isobutane by contacting the tertiary butyl hydroperoxide with at least about 2 milliequivalents per gram of total hydroperoxide present of a hydroxide or an oxide of an alkali metal or alkaline earth metal in aqueous solution and recovering the desired tertiary butyl hydroperoxide containing substantially reduced concentrations of primary and secondary alkyl hydroperoxide contaminants.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: April 22, 1986
    Assignee: Atlantic Richfield Company
    Inventors: William B. Thornton, Alfred E. Borchert
  • Patent number: 4579978
    Abstract: Substantially quantitative yields of bibenzyl hydroperoxide and bibenzyl dihydroperoxide can be obtained when oxygen is reacted with bibenzyl (1,2-diphenylethane) in the presence of a minor amount of sodium bicarbonate at a temperature within the range of about 100.degree. to about 160.degree. C. to provide an oxidation product wherein the bibenzyl is substantially selectively converted to the bibenzyl hydroperoxides. The bibenzyl hydroperoxides can be used as raw materials for the production of propylene oxide by reacting the bibenzyl hydroperoxides with propylene.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: April 1, 1986
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John R. Sanderson
  • Patent number: 4503262
    Abstract: A process is disclosed for the preparation of 2,6-dihydroisopropylnaphthalene, dihydroperoxide involving the oxidation of 2,6-diisopropylnaphthalene in the presence of a catalyst wherein the improvement comprises carrying out said oxidation in the presence of a C.sub.5 -C.sub.14 aliphatic hydrocarbon solvent.
    Type: Grant
    Filed: August 4, 1983
    Date of Patent: March 5, 1985
    Assignee: Virginia Chemicals, Inc.
    Inventors: B. Franklin Gupton, Edwin D. Little
  • Patent number: 4464304
    Abstract: A nucleophile substituted unsaturated hydrocarbon based compound is prepared by reacting a compound of the formula: ##STR1## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, or carboxyalkyl or carboxyalkenyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic reagent.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: August 7, 1984
    Assignee: Duke University
    Inventors: Ned A. Porter, Carl B. Ziegler, Jr., David H. Roberts
  • Patent number: 4455440
    Abstract: In a method for producing 1,3,5-triisopropylbenzene trihydroperoxides by bringing 1,3,5-triisopropylbenzene or its homologs into contact reaction with oxygen or an oxygen-containing gas in the co-existence of an aqueous alkali solution, a method for producing 1,3,5-triisopropylbenzene trihydroperoxides wherein said contact reaction is carried out under a condition that the reaction temperature be 60.degree. to 120.degree. C., the pH of the reaction solution phase be 8 to 11 and the amount of said aqueous alkali solution be 0.
    Type: Grant
    Filed: November 15, 1982
    Date of Patent: June 19, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tsutomu Chiyoda, Makoto Nakamura, Shinichi Hasegawa
  • Patent number: 4450303
    Abstract: High selectivities (>90%) for the production of secondary-alkyl substituted benzene hydroperoxides are achieved by heating a secondary-alkyl substituted benzene in the presence of oxygen and a samarium salt. Preferably, a free radical initiator is also present.
    Type: Grant
    Filed: February 23, 1983
    Date of Patent: May 22, 1984
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4400558
    Abstract: The present invention provides a novel method for recovering 2-phenylethanol which is produced as a by-product of non-catalytic air oxidation of ethylbenzene, and as a by-product, in the ethylbenzene hydroperoxide epoxidation of an olefinically unsaturated compound, e.g., propylene, to the corresponding alkylene oxide, e.g., propylene oxide. In such processes, 2-phenylethanol accumulates in a process stream typically comprising major proportions of methylbenzyl alcohol, ethylbenzene, alkylene oxide and acetophenone. Conventional distillation-separation procedures may remove most of the alkylene oxide and ethylbenzene, leaving a process stream which is eventually used for styrene monomer production which contains minor amounts, i.e., less than about 20 weight percent, of 2-phenylethanol.
    Type: Grant
    Filed: April 17, 1981
    Date of Patent: August 23, 1983
    Assignee: Atlantic Richfield Company
    Inventors: Margaret I. Nemet-Mavrodin, John F. White
  • Patent number: 4329514
    Abstract: Episodes of accelerated decomposition, or runaway, during the preparation of hydrocarbon hydroperoxides by reaction of hydrocarbons with molecular oxygen at elevated temperature, are brought under control through the addition to the oxidation reaction mixture of a small quantity of base in a substantially instantaneous manner at the onset of the runaway.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: May 11, 1982
    Assignee: Shell Oil Company
    Inventors: Ludovicus B. J. O. van der Weijst, Enno B. De Vries, Gerard J. Heiszwolf
  • Patent number: 4283352
    Abstract: In a method for the production of .alpha.-tetralone wherein tetralin is oxidized in the absence of a catalyst at a temperature of from 50.degree. to 100.degree. C. to an extent that the conversion of tetralin into tetralin hydroperoxide is 25 to 35 percent by weight, thereby producing a solution of tetralin hydroperoxide in tetralin, and wherein an inorganic metal salt is added to said solution to decompose the tetralin hydroperoxide to .alpha.-tetralone, the improvement comprising adding to said solution, as said inorganic metal salt, a mixture of at least one water-soluble inorganic iron salt and at least one water-soluble inorganic copper salt at a temperature of from 0.degree. to 90.degree. C.
    Type: Grant
    Filed: January 3, 1979
    Date of Patent: August 11, 1981
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takashi Yamauchi, Hirofumi Nanbu
  • Patent number: 4271321
    Abstract: Process for the preparation of araliphatic dihydroperoxides which comprises oxidizing a hydrocarbon of the formula: ##STR1## with oxygen or an oxygen-containing gas, (2) extracting the resulting dihydroperoxide with an alkali metal hydroxide solution of a concentration of 1-12% thereby producing an aqueous extract and an organic raffinate, (3) neutralizing any alkali metal hydroxide remaining in the organic raffinate with carbon dioxide, thereby producing alkali metal carbonate or bicarbonate in the raffinate, (4) washing the alkali metal carbonate or bicarbonate remaining in the raffinate with wash-water, (5) extracting from the wash-water used in step (4) any dissolved hydroperoxides remaining therein with a hydrocarbon solvent, and (6) optionally recycling the hydroperoxide-containing hydrocarbon solvent into the process. The resulting wash-water effluent is free of polluting and contaminating materials.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: June 2, 1981
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventor: Heinz W. Voges
  • Patent number: 4255592
    Abstract: An aromatic primary hydroperoxide is produced by oxidizing a methyl-substituted aromatic compound in a liquid phase with a molecular oxygen-containing gas at a temperature of 80.degree.-150.degree. C. under a pressure of the atmospheric to 100 kg/cm.sup.2 gage in the presence of 8-300 parts by weight of an aliphatic tertiary hydroperoxide per 100 parts by weight of the methyl-substituted aromatic compound. The oxidation reaction is promoted, an aromatic primary hydroperoxide content of the reaction products is increased, whereas by-products are reduced, and a selectivity to the aromatic primary hydroperoxide is considerably increased.
    Type: Grant
    Filed: September 27, 1979
    Date of Patent: March 10, 1981
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yoshio Kawai, Koichi Kida, Hideo Ikarashi, Tsukasa Toki, Yoshiharu Suzuki
  • Patent number: 4230894
    Abstract: Benzene or alkylbenzene (e.g. toluene) is alkylated with propylene to produce diisopropylbenzenes or isopropylalkylbenzenes, which in turn are selectively cracked to remove the 1,4-isomer. The resultant product, containing a high level of the 1,3-isomer, is then oxidized to 1,3-dihydroxybenzene or 3-alkylphenol (e.g. 3-methylphenyl) in significant yield.
    Type: Grant
    Filed: December 14, 1978
    Date of Patent: October 28, 1980
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4163863
    Abstract: A process for preparing a methylphenol from an alkylbenzene which process comprises oxidizing by molecular oxygen an alkylbenzene having one secondary alkyl group and 1-3 methyl groups of the general formula I ##STR1## where R is a secondary alkyl group and n is an integer of 1-3, acid-decomposing the oxidation product solution in the presence of an acid catalyst, stopping the acid-decomposition reaction before its completion, hydrogenating the acid decomposition product solution in the presence of a hydrogenation catalyst in the presence or absence of a solvent, and recovering the resulting methylphenol of the general formula II ##STR2## where n is an integer of 1-3 from the hydrogenation product solution.
    Type: Grant
    Filed: February 15, 1978
    Date of Patent: August 7, 1979
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takeo Ikarashi, Mikio Goto, Kozo Sano, Naoto Osaki, Tetsuo Aoyama, Shigeru Horie
  • Patent number: 4147726
    Abstract: An organic hydroperoxide is hydrolyzed by acid-catalysis in a reaction medium comprising essentially a mixture of a polar solvent, e.g. a low boiling, low molecular weight alcohol and/or sulfolane and phenol. Specifically cyclohexanone and phenol are obtained from cyclohexylbenzene hydroperoxide.
    Type: Grant
    Filed: November 8, 1976
    Date of Patent: April 3, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Yulin Wu