Plural Stages Each Having Oxidation Patents (Class 568/358)
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Patent number: 9221737Abstract: A reaction zone is provided zone comprising a series of oxygen clean up zones and a series of oxidation zones. A first stream is introduced to oxidation clean up zones comprising liquid cyclohexane. Next, the first stream is passed downwardly from the oxygen clean up zones to the oxidation zones, while cross-currently passing the oxygen containing gas upwardly from the oxidation zones to the oxygen clean up zones. During the reaction, the oxidation zones are maintained at a temperature range of about 145° C. to about 170° C. The product mixture is withdrawn from the oxidation zones that comprises cyclohexylhydroperoxide (CHHP), cyclohexanone and cyclohexanol. An oxidation off-gas comprising less than 3.0% by volume of unreacted oxygen is withdrawn from the oxygen clean up zones.Type: GrantFiled: July 19, 2012Date of Patent: December 29, 2015Assignee: INVISTA NORTH AMERICA S.A.R.L.Inventor: David Lee Valdez
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Patent number: 7741523Abstract: The present invention relates to a continuous method for oxidizing saturated cyclic hydrocarbons by oxygen to obtain a mixture of hydroperoxides, alcohols and ketones. It relates more particularly to a method for oxidizing cyclohexane in a column forming a bubble reactor, for the formation of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. According to the invention, the column may be supplied with oxygen-enriched air, while meeting the maximum oxygen concentration requirements in the headspace of the reactor to avoid any risk of explosion.Type: GrantFiled: October 6, 2005Date of Patent: June 22, 2010Assignee: Rhodia ChimieInventors: Serge Veracini, Frédéric Augier
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Publication number: 20090076308Abstract: The present invention relates to a continuous method for oxidizing saturated cyclic hydrocarbons by oxygen to obtain a mixture of hydroperoxides, alcohols and ketones. It relates more particularly to a method for oxidizing cyclohexane in a column forming a bubble reactor, for the formation of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. According to the invention, the column may be supplied with oxygen-enriched air, while meeting the maximum oxygen concentration requirements in the headspace of the reactor to avoid any risk of explosion.Type: ApplicationFiled: October 6, 2005Publication date: March 19, 2009Inventors: Serge Veracini, Frederic Augier
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Patent number: 6888034Abstract: Process for oxidizing cyclohexane in which oxygen is contacted with cyclohexane at a pre-selected feed rate in a first reaction zone and unconsumed oxygen is contacted with cyclohexane in a second reaction zone in which the cyclohexane feed rate is lower than the pre-selected feed rate.Type: GrantFiled: November 5, 2003Date of Patent: May 3, 2005Assignee: Invista North America S.A.R.L.Inventors: David Paul Landray, Ludovic Rick Fodor, Bruce Edwin Murphree, James Marvin Rung
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Patent number: 6500972Abstract: A method of oxidizing trimethylphenol (TMP) to trimethylbenzoquinone (TMBQ) by various molecular sieves containing various transition metals. In this method, TMP, a molecular sieve containing a transition metal in its framework, an oxidant and a solvent are mixed together to form a reaction system. The reaction system reacting at a temperature of about room temperature to 150° C. to obtain TMBQ, and the concentration of TMP is about 5-60% wt.Type: GrantFiled: July 25, 2001Date of Patent: December 31, 2002Assignee: Chinese Petroleim Corp.Inventors: Soofin Cheng, Chia-Lung Tsai, Berryinne Chou, Debasish Das
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Patent number: 6410798Abstract: A process for the preparation of 2,3,5-trimethyl-p-benzoquinone by oxidation of 2,3,5- or 2,3,6-trimethylphenol using oxygen or a gas mixture containing oxygen in the presence of a two-phase liquid reaction medium composed of water and a neocarboxylic acid having to 11 carbon atoms with a copper (II) halide-containing catalyst system at elevated temperature.Type: GrantFiled: March 8, 2001Date of Patent: June 25, 2002Assignee: Degussa-Huls AktiengesellschaftInventors: Ralf Maassen, Steffen Krill, Klaus Huthmacher
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Patent number: 6262311Abstract: Process for the preparation of 2,3,5-trimethyl-p-benzoquinone by oxidizing 2,3,5-trimethylphenol or 2,3,6-trimethylphenol with oxygen or an oxygen-containing gas mixture in the presence of a catalyst system which can be a copper halide and a transition metal halide; for example iron, chromium, manganese, cobalt, nickel, zinc or a rare earth halide, in a two-phase reaction medium, at elevated temperature.Type: GrantFiled: October 16, 2000Date of Patent: July 17, 2001Assignee: Degussa AGInventors: Ralf Maassen, Steffen Krill, Barbara Jäger, Klaus Huthmacher
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Patent number: 6075169Abstract: In a process for preparing oxidation products of cyclohexane by catalytic oxidation with oxygen-containing gases in the liquid phase, where the gases are brought into contact essentially uniformly with the liquid cyclohexane in a reaction zone, liquid cyclohexane and the oxygen-containing gases are passed in countercurrent through the reaction zone.Type: GrantFiled: April 14, 1999Date of Patent: June 13, 2000Assignee: BASF AktiengesellshcaftInventors: Alwin Rehfinger, Martin Gann, Robert Markl, Rudiger Schmitt
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Patent number: 6037491Abstract: This invention relates to methods and devices of preparing acids, such as adipic acid for example, by oxidizing a hydrocarbon, such as cyclohexane for example, with a gas containing an oxidant, preferably oxygen. A respective hydrocarbon is reacted, preferably at a steady state, with a gaseous oxidant to form an acid in a liquid mixture which preferably contains a solvent, a catalyst, water, and an initiator. The ratio of solvent to hydrocarbon may be controlled in a manner to maintain in the reaction zone maximum reaction rate and/or reactivity, or reaction rate and/or reactivity within a desired range, or reaction rate and/or reactivity directed toward a desired range. In addition, the ratio of solvent to hydrocarbon is controlled in a manner to maintain in the reaction zone substantially maximum selectivity and/or yield, or selectivity and/or yield within a desired range, or selectivity and/or yield directed toward a desired range.Type: GrantFiled: July 25, 1997Date of Patent: March 14, 2000Assignee: RPC Inc.Inventors: Eustathios Vassiliou, Mark W. Dassel, Sharon M. Aldrich, Ader M. Rostami, David C. DeCoster
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Patent number: 6008415Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products.Type: GrantFiled: July 10, 1998Date of Patent: December 28, 1999Assignee: ABB Lummus Global Inc.Inventors: Marvin I. Greene, Charles Summer, Robert J. Gartside
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Patent number: 5892122Abstract: An improved method for making cyclohexanone and cyclohexanol from oxidation of cyclohexane in which a polyprotic acid is used to neutralize caustic to prevent oligomerization of cyclohexanone during fractional distillation.Type: GrantFiled: August 25, 1997Date of Patent: April 6, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: John Joseph Ostermaier, George Crumbaugh Russell, III
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Patent number: 5817868Abstract: Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating the temperature, hold-up time, and conversion in consecutive reaction zones. The temperature in the consecutive reaction zones progressively decreases, while the hold-up time increases. Preferably, the conversion also increases. One of the major advantages of the methods and devices of the present invention is that an outstanding balance between productivity and selectivity/yield of the desired acid may be achieved. In this respect high yields and selectivities may be obtained without sacrificing productivity.Type: GrantFiled: May 21, 1997Date of Patent: October 6, 1998Assignee: Twenty-First Century Research CorporationInventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
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Patent number: 5801273Abstract: Methods and devices for controlling the reaction rate of a hydrocarbon to an acid or other intermediate oxidation product by pressure drop rate adjustments. The pressure drop rate measurements are conducted at predetermined time intervals, after stopping the feeding and exiting of gases. The pressure drop at a predetermined time interval is measured or the time it takes for the pressure to drop by a certain degree. Adjustments are then made in one or more temperature, feeding rates of hydrocarbon, solvent, catalyst, promoter, and the like until the pressure drop rate and the reaction rate fall within desirable predetermined limits.Type: GrantFiled: May 21, 1997Date of Patent: September 1, 1998Assignee: Twenty-First Century Research CorporationInventors: Eustathios Vassiliou, Mark W. Dassel, David C. DeCoster, Ader M. Rostami, Sharon M. Aldrich
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Patent number: 5801282Abstract: Methods of making intermediate oxidation products by atomizing a first liquid (in the form of droplets) containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation is controlled by monitoring the pre-coalescing temperature (temperature of the droplets just before they coalesce into a mass of liquid), or transient temperature difference (difference between the pre-coalescing temperature and the temperature of the droplets just before atomized), or transient conversion (conversion taking place in the time interval between the formation of the droplets and their coalescence into a mass of liquid) or a combination thereof.Type: GrantFiled: June 7, 1995Date of Patent: September 1, 1998Assignee: Twenty-First Century Research CorporationInventors: Mark William Dassel, Eustathios Vassiliou
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Patent number: 5780683Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The product is then catalytically hydrogenated while the product is still at reaction temperature to produce additional cyclohexanol and cyclohexanone from the precursors. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products. The hydrogenation is carried out in a reactor using a catalyst of palladium supported on carbon.Type: GrantFiled: September 11, 1996Date of Patent: July 14, 1998Assignee: ABB Lummus Global Inc.Inventors: Marvin I. Greene, Charles Sumner, Robert J. Gartside
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Patent number: 5654475Abstract: Methods of making intermediate oxidation products by atomizing a first liquid (in the form of droplets) containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation rate is controlled by monitoring and adjusting the temperatures and/or conversions at critical points of the process.Type: GrantFiled: March 25, 1996Date of Patent: August 5, 1997Assignee: Twenty-First Century Research CorporationInventors: Eustathios Vassiliou, Mark William Dassel
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Patent number: 5502245Abstract: Methods of making intermediate oxidation products by atomizing a first liquid containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation is controlled by monitoring the transient conversion (conversion taking place in the time interval between the formation of the droplets and their coalescence into a mass of liquid) of first reactant to oxidation product just before the droplets coalesce into a mass of a second liquid.Type: GrantFiled: June 7, 1995Date of Patent: March 26, 1996Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou
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Patent number: 4587363Abstract: Oxygen-containing compounds are prepared by oxidizing a hydrocarbon in the liquid phase with a gas containing molecular oxygen, at elevated temperatures and under superatmospheric pressure, by a continuous process in which the said gas is fed into the liquid reaction mixture, in a downward direction, at several points along the reaction zone via nozzle apertures, so that it emerges at each nozzle aperture with a velocity of from 0.01 to 1 m/sec in an amount of from 0.001 to 10 liters per second per nozzle aperture, and the said reaction mixture is brought into substantially uniform contact with the gas containing molecular oxygen, over the volume of the reaction zone.Type: GrantFiled: August 10, 1984Date of Patent: May 6, 1986Assignee: BASF AktiengesellschaftInventors: Jurgen Hartig, Gunter Schuch, Armin Stoessel, Guenter Herrmann, Arthur Brunner, Peter Zehner, Otto-Alfred Grosskinsky
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Patent number: 4203927Abstract: Olefins are oxidized to carbonyl compounds, for example, 2-hexene to a mixture of 2-hexanone and 3-hexanone, with a palladium/copper/boric acid catalyst and a suitable surfactant or phase transfer agent. The reaction takes place in a diluent system comprising at least two liquid phases, wherein at least one liquid phase is an aqueous phase, and in the presence of free oxygen. The catalyst system can be used to oxidize internal olefins, as well as terminal olefins, at reasonable rates. The catalyst system can also be used for the selective oxidation of linear olefins in a mixed stream containing linear and branched olefins.Type: GrantFiled: April 11, 1978Date of Patent: May 20, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp