Two Stage Oxidation From Hydrocarbon Patents (Class 562/529)
  • Patent number: 6639095
    Abstract: The present invention provides a process for preparing optically active &agr;-hydroxy acids and derivatives thereof by subjecting the alkylated 1,3-dioxolanones of formula (IV) wherein R1 and R2 are the same or different and are each independently H or C1-6 alkyl; R5 is H, C1-16 alkyl, or unsubstituted or substituted phenyl; and R6 is C1-8 alkyl, C2-7 alkenyl or unsubstituted or substituted benzyl, to either alcoholysis or hydrolysis, in which the alkylated 1,3-dioxolanones are obtained by using 10-camphorsulfonamide as a chiral auxiliary.
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: October 28, 2003
    Inventors: Biing-Jiun Uang, Jia-Wen Chang, Der-Pin Jang
  • Patent number: 6037491
    Abstract: 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: Grant
    Filed: July 25, 1997
    Date of Patent: March 14, 2000
    Assignee: RPC Inc.
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Sharon M. Aldrich, Ader M. Rostami, David C. DeCoster
  • Patent number: 5980801
    Abstract: Methods for oxidizing a hydrocarbon to an intermediate oxidation product by utilizing an activated initiator. The initiator is activated by partially oxidizing a first mixture of the initiator and a hydrocarbon, which mixture contains a rather large amount of initiator. The first mixture may even be just initiator. The first mixture, after the partial oxidation, is mixed with a second mixture containing hydrocarbon and a smaller amount of initiator. The second mixture may even contain no initiator at all. The oxidation is continued to a desired degree. Preferably, at least one of the two mixtures, and even more preferably both reaction mixtures contain an oxidation catalyst and an acidic solvent.
    Type: Grant
    Filed: June 25, 1998
    Date of Patent: November 9, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
  • Patent number: 5824819
    Abstract: Methods for oxidizing a hydrocarbon to an intermediate oxidation product by utilizing an activated initiator. The initiator is activated by partially oxidizing a first mixture of the initiator and a hydrocarbon, which mixture contains a rather large amount of initiator. The first mixture may even be just initiator. The first mixture, after the partial oxidation, is mixed with a second mixture containing hydrocarbon and a smaller amount of initiator. The second mixture may even contain no initiator at all. The oxidation is continued to a desired degree. Preferably, at least one of the two mixtures, and even more preferably both reaction mixtures contain an oxidation catalyst and an acidic solvent.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: October 20, 1998
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
  • Patent number: 5817868
    Abstract: 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: Grant
    Filed: May 21, 1997
    Date of Patent: October 6, 1998
    Assignee: Twenty-First Century Research Corporation
    Inventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
  • Patent number: 5801273
    Abstract: 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: Grant
    Filed: May 21, 1997
    Date of Patent: September 1, 1998
    Assignee: Twenty-First Century Research Corporation
    Inventors: Eustathios Vassiliou, Mark W. Dassel, David C. DeCoster, Ader M. Rostami, Sharon M. Aldrich
  • Patent number: 5801282
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: September 1, 1998
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark William Dassel, Eustathios Vassiliou
  • Patent number: 5654475
    Abstract: 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: Grant
    Filed: March 25, 1996
    Date of Patent: August 5, 1997
    Assignee: Twenty-First Century Research Corporation
    Inventors: Eustathios Vassiliou, Mark William Dassel
  • Patent number: 5502245
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: March 26, 1996
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark W. Dassel, Eustathios Vassiliou
  • Patent number: 4902827
    Abstract: Disclosed is an improved process for the preparation of adipic acid by the air oxidation of cyclohexane in the presence of acetic acid and a catalyst system comprising cobalt and zirconium and/or hafnium.
    Type: Grant
    Filed: May 3, 1988
    Date of Patent: February 20, 1990
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Norma L. Lafferty, Charles E. Sumner, Jr.
  • Patent number: 4658056
    Abstract: A process for the catalytic oxidation of liquid cycloparaffins to oxidation products thereof is disclosed. In the process, partial oxidation products are formed by oxidizing the cycloparaffin with molecular oxygen-containing gas in the presence of an oxidation catalyst comprising two heavy metal compounds. The first heavy metal compound is a cobalt compound having ligands selected from dialkyl phosphate, dicycloalkylphosphate and alkylcycloalkylphosphate, optionally additionally combined with pyridine. The second heavy metal compound is a chromium alkanoate. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] combined with chromium naphthenate.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: April 14, 1987
    Assignee: Du Pont Canada Inc.
    Inventor: Peter A. Sipos
  • Patent number: 4532347
    Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: July 30, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4450291
    Abstract: A process for the decontamination of the distillation refinement residue from the process of oxidizing cyclohexane to KA oil is provided. The process comprises washing the distillation refinement residue with the crystallization by-product obtained in crystallizing adipic acid from the product stream of the process of oxidizing the KA oil with a strong acid. This crystallization residue comprises residual amounts of the strong acid and adipic acid, as well as substantial amounts of glutaric acid and succinic acid.
    Type: Grant
    Filed: May 2, 1983
    Date of Patent: May 22, 1984
    Assignee: Monsanto Company
    Inventors: Ching T. Chi, J. Harvey Lester, Jr.
  • Patent number: 4375552
    Abstract: Waste streams from adipic acid manufacture containing nitric, succinic, glutaric and adipic acids and valuable catalytic metal as salts are treated with alcohols, thereby separating, as esters, succinic and glutaric acids which would contaminate pure adipic acid on recycling, and allowing the re-use of the resulting stream containing nitric acid and metal catalytic salts.
    Type: Grant
    Filed: June 15, 1970
    Date of Patent: March 1, 1983
    Assignee: C. P. Hall Company
    Inventor: Vincent P. Kuceski
  • Patent number: 4227021
    Abstract: An improved process for producing adipic acid from the acidic wash waters which arise in the process for oxidizing cyclohexane with air, by treatment with nitric acid at from 10.degree. to 50.degree. C., with removal of the heat of reaction by external cooling, wherein the reaction mixture is led, at a flow velocity of at least 2.0 m/sec, as a thin layer spirally in counter-current to the coolant, under conditions which do not perturb the flow of the reaction mixture.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: October 7, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Otto-Alfred Grosskinsky, Norbert Petri, Johannes Hein, Hans Leitner