Purification Or Recovery Patents (Class 568/576)
  • Patent number: 8697130
    Abstract: Crystalline benzoyl peroxide particles having a particle size no greater than 25 microns and formed by wet milling in the absence of solvents and wherein the crystalline benzoyl peroxide is not irritating to the skin. A therapeutic or cosmetic composition comprising a water-based gel containing the crystalline benzoyl peroxide.
    Type: Grant
    Filed: May 24, 2011
    Date of Patent: April 15, 2014
    Assignee: Essential Ingredients, Inc.
    Inventors: Chris Gerlach, Mike Davies
  • Patent number: 8536379
    Abstract: The present application relates to a method for manufacturing tert-butyl hydroperoxide that includes the following steps: a) fermenting renewable raw materials and optionally purifying the same to produce a mixture containing at least butanol; b) dehydrating the butanol into butane; c) converting the butane into isobutene and optionally hydrating the isobutene to produce tert-butanol; d) reacting the product of step c) with hydrogen peroxide so as to produce tert-butyl hydroperoxide; and e) isolating the tert-butyl hydroperoxide. The invention also relates to tert-butyl hydroperoxide containing carbon atoms from renewable resources, to the compositions containing said tert-butyl hydroperoxide, and also relates to the use thereof as a polymerization initiator.
    Type: Grant
    Filed: September 24, 2009
    Date of Patent: September 17, 2013
    Assignee: Arkema France
    Inventors: Serge Hub, Philippe Maj
  • Publication number: 20120149942
    Abstract: There is provided a method for handling an aqueous solution containing a water-soluble substance that changes into a water-insoluble substance over time, including a step of bringing the aqueous solution to be treated containing the water-soluble substance that changes into the water-insoluble substance over time into contact with a water-insoluble organic solvent, and extracting the water-soluble substance into the water-insoluble organic solvent. Preferably, the water-soluble substance is alkylbenzene hydroperoxide, and the water-insoluble substance is alkylbenzene hydroperoxide-derived alcohol. Preferably, the aqueous solution to be treated is an alkaline aqueous phase separated in a water-washing step in a process of manufacturing the alkylbenzene hydroperoxide that has an alkali extraction step, the water-washing step, an oxidation step, and a reaction solution separation step.
    Type: Application
    Filed: August 19, 2010
    Publication date: June 14, 2012
    Inventors: Mitsuru Onuma, Tomoyuki Noritake, Shigeru Goto
  • Patent number: 7863493
    Abstract: A process for preparing an organic hydroperoxide, which process comprises: (a) oxidizing an organic compound to obtain an organic reaction product containing organic hydroperoxide; (b) mixing at least part of the organic reaction product of step (a) with a basic aqueous solution to obtain a mixture of basic aqueous solution and the organic reaction product; (c) separating the mixture of step (b) to obtain a separated organic phase containing organic hydroperoxide, and a separated aqueous phase; (d) mixing at least part of the separated organic phase of step (c) with water to obtain a mixture of an aqueous phase and the organic phase; and (e) separating the mixture of step (d) to obtain a separated organic phase containing organic hydroperoxide, and a separated aqueous phase; in which process the separation to a separated organic phase and a separated aqueous phase in step (e) is carried out with the help of a coalescer containing glass fibers.
    Type: Grant
    Filed: June 21, 2006
    Date of Patent: January 4, 2011
    Assignee: Shell Oil Company
    Inventors: Anke Derking, Wan Shi Foong, Raymond Lawrence June, Chao-Yuan Kho, Mohammad Azmi Bin Othman, Hoi-Yan Yuen
  • Patent number: 7763756
    Abstract: A method for collecting an object material from a solution, which comprises the following steps: a step of adding a second solvent to a solution composed of an object material to be collected and a first solvent, then mixing therewith to form an emulsion containing the object material in a state under which the emulsion is not uniformly dissolved in the second solvent, in the second solvent; and a step of separating thus obtained emulsion from the solution.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: July 27, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigenori Shiraishi, Shigeru Goto, Masaaki Katao
  • Patent number: 7678943
    Abstract: A process for the autocatalytic production of organic hydroperoxides and ultra low sulfur diesel boiling range hydrocarbons is disclosed. The organic hydroperoxides react with sulfur compounds to produce sulfones, and the sulfones can be removed from the diesel boiling range hydrocarbons to provide ultra low sulfur diesel.
    Type: Grant
    Filed: October 18, 2007
    Date of Patent: March 16, 2010
    Assignee: UOP LLC
    Inventors: Christopher D. Gosling, Ronald M. Gatan, Paul T. Barger
  • Patent number: 7102035
    Abstract: A process is disclosed for reducing the concentration of a dialkyl ether in a mixture comprising the dialkyl ether and a dialkyl peroxide wherein the process comprises treating said mixture with a strong acid.
    Type: Grant
    Filed: June 23, 2004
    Date of Patent: September 5, 2006
    Assignee: Crompton Corporation
    Inventors: Peter Frenkel, Delphine Meeh, Lawrence A. Bock, Anthony Andrews
  • Patent number: 7049474
    Abstract: The present invention provides for the use of water, rather than cumene, as a more environmentally acceptable diluent for purified cumene hydroperoxide (CHP) solutions. From 1 to about 6 weight percent water can be used to dilute purified CHP solutions, thus reducing or eliminating the use of a hazardous compound, cumene, as a diluent. The method and CHP-water solutions of the present invention should significantly reduce or eliminate the hazardous emissions problems encountered with the use of cumene as a diluent and make CHP solutions more environmentally acceptable to produce, transport and use. Water as a diluent also depresses the freezing point of the resultant solution, thereby permitting year-round use of higher concentration CHP solutions. Water diluted CHP solutions will also reduce cumene-related impurities in finished products made therefrom.
    Type: Grant
    Filed: September 12, 2000
    Date of Patent: May 23, 2006
    Assignee: Sunoco, Inc. (R&M)
    Inventors: Keith E. Henry, John E. Aiken
  • Patent number: 6369278
    Abstract: There are provided: (I) a process for preparing an extract containing at least one hydroperoxide, which comprises the steps of: (1) oxidizing an aromatic hydrocarbon substituted with an alkyl group to obtain a liquid reaction mixture, and (2) extracting at least one hydroperoxide in the liquid reaction mixture to obtain an extract having a concentration of acetone of not more than 1% by weight: and (II) a process for preparing an extract containing at least one hydroperoxide, which comprises the steps of, (1) oxidizing an aromatic hydrocarbon substituted with an alkyl group to obtain a liquid reaction mixture, and (2) extracting at least one hydroperoxide with an aqueous alkali solution having an A value of not more than 10 to obtain an extract.
    Type: Grant
    Filed: December 7, 2000
    Date of Patent: April 9, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomoyuki Noritake, Shigeru Goto, Kenji Itoh
  • Patent number: 5959155
    Abstract: A process for extraction of hydroperoxides wherein 1,3-di-(2-hydroperoxy-2-propyl)benzene and 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene are extracted from a raw solution comprising 1,3-di-(2-hydroperoxy-2-propyl)benzene, 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene and an aqueous sodium hydroxide solution, said process using methyl isobutyl ketone containing not more than 10 ppm by weight of a phenol or phenols as a solvent for extraction.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: September 28, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshikazu Ohmae, Shigefumi Tokumasu, Hideo Ohki
  • Patent number: 5705708
    Abstract: Discoloration of cumene hydroperoxide is reduced or inhibited by adding to the cumene hydroperoxide an effective amount on the order of 30 to 1000 ppm of a stabilizer of the formula R'C(O)OM wherein R' is alkyl, alkenyl, cycloalkyl or aryl containing 1-40 carbon atoms, or the formula R.sub.4 NOH wherein each R is independently alkyl or cycloalkyl containing 1-40 carbon atoms.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: January 6, 1998
    Assignee: Witco Corporation
    Inventor: Peter Frenkel
  • Patent number: 5658437
    Abstract: A process for reducing the COD of an aqueous stream containing methylhydroperoxide, cumylhydroperoxide and other organic impurities characterized in that the reduction of COD is obtained by eliminating the peroxides from the aqueous stream by column distillation.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: August 19, 1997
    Assignee: Enichem S.p.A.
    Inventors: Vanni Alessi, Alessandro Franzoni, Vittorio Milanesi, Renzo Penzo
  • Patent number: 5554796
    Abstract: A process for the purification of tertiary alkyl hydroperoxide containing contaminating quantities of primary and secondary alkyl hydroperoxides by contacting the impure hydroperoxide mixture with anhydrous carboxylic acid derivative such as maleic anhydride and subsequently reacting the resulting mixture with basic material such as aqueous caustic and recovering purified tertiary alkyl hydroperoxide.
    Type: Grant
    Filed: April 29, 1994
    Date of Patent: September 10, 1996
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Ahmad Soltani-Ahmadi, Robert N. Cochran
  • Patent number: 5539131
    Abstract: In the Oxirane process for epoxide production, at least part of the alcohol formed during isobutane or isopentane peroxidation is replaced by an inert solvent such as decane.
    Type: Grant
    Filed: July 13, 1995
    Date of Patent: July 23, 1996
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Shaw-Chan Lin
  • Patent number: 5488177
    Abstract: A method is described for the preparation of solutions containing little or no water of tertiary alkyl hydroperoxides in inert solvents by dewatering with sulfuric acid, according to which one or more inert organic solvents are added to an aqueous solution as well as sulfuric acid in such amount and concentration that in the aqueous phase forming after the mixing followed by separation of the phases there is at least 49% of H.sub.2 SO.sub.4 and the water content in the organic phase amounts to no more than 2.5%.
    Type: Grant
    Filed: November 1, 1994
    Date of Patent: January 30, 1996
    Assignee: Peroxid-Chemie GmbH
    Inventors: Hans Appel, Fritz Diem
  • Patent number: 5453548
    Abstract: A process for the separation of ditertiary butyl peroxide form tertiary butanol is provided which includes the step of dehydrating the tertiary butanol to isobutylene and water.
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: September 26, 1995
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Robert Nedwick, Jeffrey M. McFarland, Leonard A. Fabiano
  • Patent number: 5334771
    Abstract: A secondary carbon atom in an alkane, including alkyl groups attached to aromatic rings, or cycloalkane is peroxidized by molecular oxygen to the corresponding hydroperoxide in the absence of a catalyst. The peroxidation is carried out in the presence of a tertiary hydroperoxide initiator which provides the free radicals needed to maintain the reaction. The amount of tertiary alcohol in the initiator is limited. The initial product of the peroxidation contains the secondary hydroperoxide as well as unreacted hydrocarbon, unreacted tertiary hydroperoxide and tertiary alcohol. The tertiary alcohol is removed as an azeotrope with part of the unreacted hydrocarbon which may be then separated from the alcohol and recycled. A second azeotropic distillation follows where the unreacted tertiary hydroperoxide is removed as an azeotrope with the rest of the unreacted hydrocarbon. This azeotrope is directly recycled to the peroxidation reaction.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: August 2, 1994
    Assignees: ABB Lummus Crest Inc., Nitrocarbono S.A.
    Inventors: George Ember, Edilberto A. De Castro Netro, Rogerio F. De Lacerda
  • Patent number: 5283370
    Abstract: A process for the partial dehydration and partial purification of a crude water-wet organic stream of the monohydroperoxide of p-diisopropylbenzene is disclosed. This crude stream of monohydroperoxide contains at least 2 wt % water and is partially dehydrated by contacting the stream with a non-reactive inorganic salt to remove a portion of the water into a concentrated brine of the inorganic salt followed by separation of the concentrated brine and the product. The crude water-wet organic stream of the monohydroperoxide is optionally filtered and coalesced prior to contacting the nonreactive inorganic salt.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: February 1, 1994
    Inventors: J. Ronald Hilderbrand, Stephan B. Meydell, III
  • Patent number: 5202498
    Abstract: Undesirable color change in freshly manufactured cumene hydroperoxide is inhibited by treatment comprising adding sodium hydroxide in an effective amount up to about 120 ppm and holding the treated cumene hydroperoxide at a temperature of about 50.degree. C. to about 70.degree. C. for 0.5 to two hours; optionally the cumene hydroperoxide so treated in the higher end of this caustic range is further treated with a wiped-film evaporator.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: April 13, 1993
    Assignee: Aristech Chemical Corporation
    Inventor: Carole L. Elias
  • Patent number: 5166451
    Abstract: Method of treating a hydroperoxide mixture containing both a primary and tertiary aromatic hydroperoxide, by treating the mixture with an alkali and an organic quaternary ammonium salt. This treatment selectively reduces the content of the primary hydroperoxide in the mixture.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: November 24, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akira Takeshita, Shinzaburo Masaki, Osamu Maruyama
  • Patent number: 5104493
    Abstract: The invention relates to a process for concentrating TBHP while avoiding flammability and explosion hazards by distilling a mixture of TBHP and TBA under reduced pressure of up to 300 mm Hg and separating a liquid TBHP concentrate containing at least 65 wt. % TBHP.
    Type: Grant
    Filed: January 24, 1991
    Date of Patent: April 14, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Victor M. Chong
  • Patent number: 4891101
    Abstract: Primary and secondary hydroperoxide contaminants in a tertiary hydroperoxide composition obtained by oxidation of a branched hydrocarbon are removed by contacting the tertiary hydroperoxide with a carboxylic acid derivative such as an anhydride and a basic compound such as sodium hydroxide. A tertiary hydroperoxide such as tertiary butyl hydroperoxide is purified with minimal loss of the desired tertiary hydroperoxide.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: January 2, 1990
    Assignee: Arco Chemical Technology, Inc.
    Inventor: Carl J. Sullivan
  • Patent number: 4670609
    Abstract: An improved process for the manufacture of a dihydric phenol such as hydroquinone wherein a dialkylbenzene is oxidized to a dihydroperoxide, the dihydroperoxide being extracted from the oxidate by a caustic solution, leaving an organic phase for recycle to the oxidizer, the improvement comprising decreasing the caustic concentration in the recycle organic phase and increasing the dihydroperoxide concentration of the recycle phase by washing the organic phase from the caustic extract with an aqueous phase removed from the oxidizer, separating the organic phase from the aqueous phase and subsequently introducing the organic phase to the oxidizer.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: June 2, 1987
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Ronald Q. Bennett, Donald E. Smith, Joel Muse, Jr.
  • Patent number: 4654124
    Abstract: Crude cumene hydroperoxide is purified by subjecting it to an evaporation step at a pressure of about 2 to 10 (preferably 3 to 7) mg Hg abs. and a temperature of about 150.degree. F. to about 210.degree. F. (pref. about 175.degree. F. to 195.degree. F.) to remove light impurities and then subjecting the residue from the first evaporation step to a second evaporation step also at a temperature of about 135.degree. F. to 210.degree. F. (pref. about 150.degree. F. to 185.degree. F.) but at a pressure of about 0.5 to about 8 (preferably 1 to 3) mm Hg abs. to obtain a distillate significantly reduced in color bodies, water, acetophenone, and dimethylbenzyl alcohol, and sodium.
    Type: Grant
    Filed: March 20, 1986
    Date of Patent: March 31, 1987
    Assignee: Aristech Chemical Corporation
    Inventors: Carole L. Elias, Marvin C. Fields
  • 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: 4408083
    Abstract: Disclosed is a method of treating hydroperoxide mixtures, which comprises bringing an oily hydroperoxide mixture containing (A) an aromatic hydroperoxide having a hydroperoxymethyl group directly bonded to the aromatic nucleus and (B) an aromatic hydroperoxide having a 2-hydroperoxy-2-propyl group bonded directly to the aromatic nucleus into contact with an aqueous alkali solution, separating the aqueous phase from the oil phase and decomposing at least a part of the component (A) extracted in the aqueous phase.According to this method, the starting oily hydroperoxide mixture can be converted to a mixture in which the primary hydroperoxide content is reduced without substantial loss of the tertiary hydroperoxide. Therefore, aromatic hydroperoxide mixtures suitable for production of phenols can advantageously be proceeded.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: October 4, 1983
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Masakazu Toyoura, Koichi Shomura, Hirotoshi Tsuchida, Tadateru Murakami
  • Patent number: 4381222
    Abstract: A process for the distillative separation of tertiary alkyl hydroperoxides of the formulaR--OOHwhereinR is a tertiary alkyl group with 4 to 6 carbon atoms from the corresponding di-tertiary alkyl peroxides resulting during their preparation, which process comprises neutralizing the reaction mixture resulting during the preparation of the tertiary alkyl hydroperoxide, subjecting same to vacuum distillation in the presence of water at a temperature of less than about 45.degree. C. and recovering the purified tertiary alkyl hydroperoxide as a bottoms product.
    Type: Grant
    Filed: October 27, 1981
    Date of Patent: April 26, 1983
    Assignee: Peroxide-Chemie GmbH
    Inventors: Gottfried Brossmann, Fritz Diem
  • Patent number: 4371721
    Abstract: A process for selective cracking of 1,4-disubstituted benzene compounds having at least one polar substituent. Mixtures containing isomers of such a compound are brought into contact with a specified type of shape selective crystalline zeolite catalyst under conditions of temperature and pressure conducive to reaction of said benzene compound, thereby selectively reacting the 1,4-disubstituted isomer in preference to the 1,2- and 1,3-disubstituted isomers of said polar benzene compound. The shape selective zeolite catalysts employed herein are crystalline zeolites characterized by a silica to alumina ratio of at least about 12 and a constraint index within the approximate range of 1 to 12.
    Type: Grant
    Filed: September 25, 1981
    Date of Patent: February 1, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Margaret M. Wu
  • Patent number: 4293720
    Abstract: Disclosed is a process for the preparation of hydroperoxides comprising liquid-phase oxidizing an aromatic compound having a secondary alkyl group with molecular oxygen in the presence of a basic aqueous solution and a copper compound catalyst, wherein an aqueous solution containing (A) cupric carbonate and (B) an alkali metal carbonate and/or an alkali metal bicarbonate is prepared outside the oxidation system and this aqueous solution is supplied to the oxidation system.According to the process, even under basic conditions, inactivation of the catalyst owing to precipitation is prevented, and the intended aromatic hydroperoxide can be obtained at a high oxidation speed.
    Type: Grant
    Filed: May 2, 1980
    Date of Patent: October 6, 1981
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tetsuo Iwaki, Yukio Takahashi, Shuji Moriuchi, Hisamitsu Kaneko
  • 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: 4257852
    Abstract: Hazards are dealt with by appropriate placement of high heat capacity flame arrestor packings at suitable zones in the flow of the process streams comprising vapors of flammable mixture containing water and more than 10 mol % tertiary butyl hydroperoxide (conveniently designated as TBHP). Stainless steel mesh or other corrosion resistant high heat capacity packing is inserted in the lower portion of the first distillation zone, from which all components more volatile than dilute aqueous TBHP are removed. Suitable packing is also inserted into the upper portion of the second distillation zone, whereby a flammable mixture containing more than 10 mol % TBHP, is distilled without allowing a large plenum filled with flammable vapor. The vapor line between the top of such distillation zone and a condensation zone features a plurality of flame arrestors (e.g.
    Type: Grant
    Filed: January 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Atlantic Richfield Company
    Inventor: G. Richard Worrell
  • Patent number: 4230890
    Abstract: Separation of diisopropylbenzene dihydroperoxide from a diisopropylbenzene oxidation reaction mixture by treating the reaction mixture with concentrated alkali metal hydroxide and recovering the alkali metal salt of diisopropylbenzene dihydroperoxide in high purity and good yield, and subsequently converting the salt to diisopropylbenzene dihydroperoxide.
    Type: Grant
    Filed: July 19, 1978
    Date of Patent: October 28, 1980
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Ward J. Burkholder
  • Patent number: 4160000
    Abstract: A hydroperoxide containing reaction mixture also containing a corresponding unreacted hydrocarbon is treated with an aqueous alcoholic solvent, e.g., aqueous methanolic solvent, to provide in a first step an extract containing a high percentage of hydroperoxide and an appreciable amount of original or unreacted hydrocarbon whereupon the extract is treated with water under recited conditions to obtain two desired phases, one of which is primarily hydrocarbon rejected from the extract by the addition of water and the other an aqueous methanolic solution of the desired hydroperoxide suitable for use in the acid-catalyzed decomposition for the production of carbonyl compounds and hydroxy compounds.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: July 3, 1979
    Assignee: Phillips Petroleum Company
    Inventors: John F. Hutto, Alfred A. Hoffman, Jr.