Two Stage Oxidation From Hydrocarbon Patents (Class 562/529)
-
Patent number: 6639095Abstract: 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: GrantFiled: October 8, 2002Date of Patent: October 28, 2003Inventors: Biing-Jiun Uang, Jia-Wen Chang, Der-Pin Jang
-
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
-
Patent number: 5980801Abstract: 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: GrantFiled: June 25, 1998Date of Patent: November 9, 1999Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
-
Patent number: 5824819Abstract: 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: GrantFiled: May 21, 1997Date of Patent: October 20, 1998Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
-
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
-
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
-
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
-
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
-
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
-
Patent number: 4902827Abstract: 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: GrantFiled: May 3, 1988Date of Patent: February 20, 1990Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Norma L. Lafferty, Charles E. Sumner, Jr.
-
Patent number: 4658056Abstract: 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: GrantFiled: April 22, 1982Date of Patent: April 14, 1987Assignee: Du Pont Canada Inc.Inventor: Peter A. Sipos
-
Patent number: 4532347Abstract: 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: GrantFiled: January 21, 1980Date of Patent: July 30, 1985Assignee: Varen TechnologyInventor: Ronald J. Vaughan
-
Patent number: 4450291Abstract: 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: GrantFiled: May 2, 1983Date of Patent: May 22, 1984Assignee: Monsanto CompanyInventors: Ching T. Chi, J. Harvey Lester, Jr.
-
Patent number: 4375552Abstract: 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: GrantFiled: June 15, 1970Date of Patent: March 1, 1983Assignee: C. P. Hall CompanyInventor: Vincent P. Kuceski
-
Patent number: 4227021Abstract: 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: GrantFiled: April 28, 1978Date of Patent: October 7, 1980Assignee: BASF AktiengesellschaftInventors: Otto-Alfred Grosskinsky, Norbert Petri, Johannes Hein, Hans Leitner