Cyclic Ketone Or Mixture Thereof With Cyclic Alcohol Patents (Class 562/528)
  • Patent number: 9168469
    Abstract: A fiber reaction process whereby reactive components contained in immiscible streams are brought into contact to effect chemical reactions and separations. The conduit reactor utilized contains wettable fibers onto which one stream is substantially constrained and a second stream is flowed over to continuously create a new interface there between to efficiently bring about contact of the reactive species and thus promote reactions thereof or extractions thereby. Co-solvents and phase transfer catalysts may be employed to facilitate the process.
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: October 27, 2015
    Assignee: Chemtor, LP
    Inventor: John Lee Massingill
  • Patent number: 8846975
    Abstract: A process for preparing dicarboxylic acids is described. More particularly a process is described for preparing adipic acid (1,6-hexanedioic acid), by the action of nitric acid, starting from cyclic ketones or alcohols which are the corresponding compounds from the standpoint of the number of carbon atoms, in the presence of one or more oxides of nitrogen at a molar concentration in the reaction mixture of greater than 2.5 mmol per kg of reaction mixture.
    Type: Grant
    Filed: May 9, 2011
    Date of Patent: September 30, 2014
    Assignee: Rhodia Operations
    Inventors: Sandra Chouzier, Gérard Mignani, Simon Rousseau, Flavie Sarrazin, Sergio Mastroianni
  • Publication number: 20130211036
    Abstract: A process for oxidizing a composition comprising contacting an alkylbenzene of the general formula (I): where R1 and R2 each independently represents hydrogen or an alkyl group having from 1 to 4 carbon atoms, wherein R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, the cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group; and (ii) about 0.05 wt % to about 5 wt % of phenol, with oxygen in the presence of a catalyst containing a cyclic imide having the general formula (II): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group under conditions effective to convert at least a portion of the alkylbenzene to a hydroperoxide.
    Type: Application
    Filed: August 16, 2011
    Publication date: August 15, 2013
    Applicant: ExxonMobil Chemical Company - Law Technology
    Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Charles Morris Smith, Christopher L. Becker, Stephen Zushma
  • Publication number: 20130109886
    Abstract: A process for preparing dicarboxylic acids is described. More particularly a process is described for preparing adipic acid (1,6-hexanedioic acid), by the action of nitric acid, starting from cyclic ketones or alcohols which are the corresponding compounds from the standpoint of the number of carbon atoms, in the presence of one or more oxides of nitrogen at a molar concentration in the reaction mixture of greater than 2.5 mmol per kg of reaction mixture.
    Type: Application
    Filed: May 9, 2011
    Publication date: May 2, 2013
    Applicant: RHODIA OPERATIONS
    Inventors: Sandra Chouzier, Gérard Mignani, Simon Rousseau, Flavie Sarrazin, Sergio Mastroianni
  • Publication number: 20110306789
    Abstract: A process for the manufacture of adipic acid carried out in devices made of material resistant to the corrosion of the synthesis medium is described. A process for the manufacture of adipic acid carried out in devices, some of which are made of a material resistant to corrosion by nitric acid, is also described. The corrosion-resistant material can be a “duplex” austenoferritic stainless steel of X2 CrNiN 23-4 (1.4362) type, according to the European nomenclature.
    Type: Application
    Filed: November 27, 2009
    Publication date: December 15, 2011
    Applicant: RHODIA OPERATIONS
    Inventors: Philippe Carvin, Fabien Bellenger, Serge Crottier-Combe
  • Patent number: 7312357
    Abstract: The present invention discloses a process for producing an aliphatic dicarboxylic acid compound, which comprises oxidizing, with a nitrite or a nitrate in the presence of trifluoroacetic acid, an alicyclic secondary alcohol compound or an alicyclic ketone compound, in each of which at least one methylene group is bonded to the carbon atom having hydroxyl group bonded thereto or the carbon atom as a member of carbonyl group, wherein the reaction is conducted in the presence of water of 5 mass % or less relative to 100 mass % of the total of the trifluoroacetic acid and the water.
    Type: Grant
    Filed: March 23, 2005
    Date of Patent: December 25, 2007
    Assignee: Tokuyama Corporation
    Inventors: Yoshihiro Matsumura, Osamu Onomura, Fumiaki Iwasaki
  • Patent number: 7186858
    Abstract: The present invention provides a safe, convenient and efficient method for producing carboxylic acid by a reaction of alicyclic alcohol with an aqueous hydrogen peroxide to thereby obtain carboxylic acid in high yield from alicyclic alcohol or alicyclic ketone under mild reaction conditions, wherein the reaction operation is simple and easy, a step for removing solvent after completion of the reaction is not necessary and influence and toxicity upon the environment and human body are markedly small. In order to provide it, an oily alicyclic alcohol is allowed to react with an aqueous hydrogen peroxide in the presence of a catalyst containing a metal compound belonging to Group 6 of the Periodic Table in a heterogeneous solution system.
    Type: Grant
    Filed: July 24, 2003
    Date of Patent: March 6, 2007
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Kazuhiko Sato, Youko Usui
  • Patent number: 7084300
    Abstract: Degradation acids obtained in the synthesis of carboxylic acids, in particular dicarboxylic acids, having from 8 to 16 carbon atoms may be isolated by separating the degradation acids in the form of a solid from the crude reaction mixture, then washing the degradation acids in the form of an oil with water at an elevated temperature. The resulting degradation acids having low oxidant and metal contents, and the metal catalyst may be recirculated back to the process.
    Type: Grant
    Filed: April 11, 2003
    Date of Patent: August 1, 2006
    Assignee: Degussa AG
    Inventors: Juergen Herwig, Ralf Richter, Martin Roos, Georg Oenbrink
  • Patent number: 7045656
    Abstract: A process is described for recycling catalysts in the reaction for the oxidation of alcohols and/or ketones to carboxylic acids and more particularly the oxidation of cyclic alcohols and/or cyclic ketones to dicarboxylic acids, such as the oxidation of cyclohexanol and/or cyclohexanone to adipic acid. This process involves treating the solution comprising the oxidation catalyst, before it is recycled, with an ion-exchange resin which makes it possible to selectively separate the iron from the other metal elements, in particular from copper and from vanadium.
    Type: Grant
    Filed: May 17, 2004
    Date of Patent: May 16, 2006
    Assignee: Rhodia Fiber & Resin Intermediates
    Inventors: Patrice Gotteland, Sébastien Logette
  • Patent number: 7019167
    Abstract: A method for manufacturing an alkanedicarboxylic acid by oxidizing cycloalkanol and/or cycloalkanone with an aqueous solution of nitric acid, which comprises using an adiabatic reactor comprising a feed nozzle enabling to feed cycloalkanol and/or cycloalkanone at a linear velocity not lower than 8×10?2 m/sec and a mixing apparatus.
    Type: Grant
    Filed: January 24, 2002
    Date of Patent: March 28, 2006
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Masatsugu Kawase, Yasuhiro Murozono
  • Publication number: 20040073061
    Abstract: A method for manufacturing an alkanedicarboxylic acid by oxidizing cycloalkanol and/or cycloalkanone with an aqueous solution of nitric acid, which comprises using an adiabatic reactor comprising a feed nozzle enabling to feed cycloalkanol and/or cycloalkanone at a linear velocity not lower than 8×10−2 m/sec and a mixing apparatus.
    Type: Application
    Filed: July 24, 2003
    Publication date: April 15, 2004
    Inventors: Masatsuga Kawase, Yasuhiro Murozono
  • Patent number: 6632964
    Abstract: A process of producing an aliphatic aldehyde-acid (e.g., adipaldehyde-acid) and/or an aliphatic dicarboxylic acid (e.g., adipic acid) comprising oxidizing a cyclic ketone (e.g., cyclohexanone) with molecular oxygen in the presence of a fixed catalyst which comprises a composite of a carrier and at least one metal element belonging to the groups 4 to 11 of the Periodic Table supported on the carrier and has an acid amount of 0.06 mmol/g or more per unit weight of the carrier.
    Type: Grant
    Filed: June 22, 2001
    Date of Patent: October 14, 2003
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masaru Fujii, Tohru Setoyama
  • Patent number: 6521789
    Abstract: The present invention relates to an improved process for the preparation of adipic acid. More particularly, the present invention relates to an environmental-friendly, clean process for the preparation of adipic acid through oxidation of cyclohexanol, cyclohexanone or a mixture thereof with oxygen or oxygen-containing gas, in the presence of an oxidation initiator, a polar solvent and an organometallic &mgr;3-oxo-bridged Co/Mn cluster complex catalyst.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: February 18, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Darbha Srinivas, Suhas Arunkumar Chavan, Paul Ratnasamy
  • 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: 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: 5663388
    Abstract: A process for forming acids from aldehydes which comprises reacting an oxo aldehyde with water in the presence of an acid-forming catalyst and in the absence of hydrogen, and at a pressure of about 0.1 to 6.99 MPa and a temperature of about 93.degree. to 205.degree. C., thereby converting aldehyde to an oxo acid.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: September 2, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jose M. Vargas, Magdiel Agosto
  • 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: 5420336
    Abstract: Copper and vanadium catalyst components are recovered and dialkyl esters of dicarboxylic acids are synthesized by precipitating the catalyst metals with an alcohol selected from the group consisting of methanol, ethanol, and isopropanol removal of the precipitate, and then heating the mixture.
    Type: Grant
    Filed: November 2, 1994
    Date of Patent: May 30, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Howard W. Anderson, James E. Matush, Brent G. Sparks, Eugene D. Wilhoit
  • Patent number: 5191104
    Abstract: This invention relates to a process for the alkoxylation of a carboxylated compound comprising contacting the carboxylated compound with an alkylene oxide in the presence of a mixed metal oxide catalyst or a modified bimetallic or polymetallic catalyst under conditions effective to alkoxylate the carboxylated compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: March 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 4988825
    Abstract: Aldehydes and ketones, other than acetone, are oxidized with an alkali metal perborate in the presence of an acid.
    Type: Grant
    Filed: September 23, 1986
    Date of Patent: January 29, 1991
    Assignee: Cooper Union Research Foundation, Inc.
    Inventor: John L. Bove
  • Patent number: 4983767
    Abstract: Aliphatic carboxylic acids, e.g., adipic acid, are prepared by oxidizing a monocyclic ketone with molecular oxygen or an oxygen-containing gas, in the presence of a catalytically effective amount of a vanadium compound having one of following formulae (I) and (II):H.sub.3+n [PM.sub.12-n V.sub.n O.sub.40 ].multidot.y H.sub.2 O (I)VO(Y).sub.m (II)in which n is an integer greater than or equal to 1 and less than or equal to 6; M is a molybdenum or tungsten atom; y is an integer ranging from zero to less than 50; Y is an acetylacetonate group or an alkoxy radical containing from 1 to 10 atoms; and m is 2 or 3.
    Type: Grant
    Filed: August 15, 1989
    Date of Patent: January 8, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Marie Bregeault, Bassam El-Ali, Jacques Martin
  • Patent number: 4959494
    Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: September 25, 1990
    Assignee: Monsanto Company
    Inventor: Timothy R. Felthouse
  • 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: 4883910
    Abstract: An organic compound having a cyclic aliphatic moiety is oxidized with a vanadium containing heteropolyanion compound having the formulaA.sub.m XY.sub.12-n V.sub.n.sup.+5 O.sub.40whereinA is H, Li, K or Na:X is P.sup.+5, Si.sup.+4, Ge.sup.+4 or B.sup.+3 ;Y is Mo or W;n is an integer from 1 to 10; andm is 3+n where X is P.sup.+5 or As.sup.+5, 4+n where X is Si.sup.+4 or Ge.sup.+4, and 5+n where X is B+3.No metal catalyst is required. Exemplary is the oxidation of cyclohexanone, cyclohexanol, or any combination thereof to obtain adipic acid.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: November 28, 1989
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: William C. Seidel
  • Patent number: 4870192
    Abstract: This invention provides process embodiments for shape-selective oxidation of cyclic ketones to lactone and/or omega-hydroxycarboxylic acid products in the presence of a zeolite catalyst composition such as ZSM-5 or zeolite Beta.Cyclohexanone can be converted to epsilon-caprolactone or 6-hydroxycaproic acid as a main product under selected conditions.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: September 26, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Stuart D. Hellring
  • Patent number: 4841096
    Abstract: A cyclohexane-2,5-dione-1,4-ylene-bis (-3-propionic acid) derivative represented by the formula ##STR1## wherein R is hydrogen or alkyl. The derivative is prepared by heating a cyclohexane-2,5-dione derivative represented by the formula ##STR2## wherein R is as defined above, and R.sub.1 is alkyl, in the presence of water.
    Type: Grant
    Filed: December 8, 1987
    Date of Patent: June 20, 1989
    Assignee: Nippon Gosei Kaagaku Kogyo
    Inventor: Masahiko Miyashita
  • Patent number: 4739114
    Abstract: This invention relates to a novel method of preparing 3-alkyl-substituted glutaric acids and 2-alkyl-substituted succinic acids from 5-alkyl-substituted-1,3-cyclohexane-diones or 3-alkyl-substituted-5-ketohexanoic acids via transition-metal catalyzed oxidation.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: April 19, 1988
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Young J. Lee, Robert C. Ligon, Herbert E. Johnson
  • Patent number: 4649217
    Abstract: Oxocarboxylic acids, for example adipaldehydic acid can be advantageously produced by a process, in which cyclohexanones are oxidized with molecular oxygen in the presence of water and iron or iridium compound, preferably also in the presence of a sulfur or organic nitrogen compound.
    Type: Grant
    Filed: March 15, 1983
    Date of Patent: March 10, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Takao Maki, Kenji Murayama, Yoshio Asahi
  • 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: 4510321
    Abstract: Processes for the autoxidative cleavage of selected ketones such as C.sub.4 -C.sub.10 cycloalkanones having at least one hydrogen or at least one R group on a carbon alpha to the carbonyl carbon or aryl alkyl ketones having the formula III ##STR1## comprising contacting a liquid phase comprising said ketone with elemental oxygen gas, preferably air, in the presence of a pulverized alkali metal hydroxide at a temperature of no more than 50.degree. C. for a time sufficient to produce an oxidized product are disclosed. Preferred cycloalkanones, 2-alkyl- and 2-arylcyclohexanone are autoxidized in pulverized sodium hydroxide/dimethoxyethane to produce 6-alkyl- or 6-aryl-6-oxohexanoic acids, respectively.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: April 9, 1985
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Edward H. Manahan
  • 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: 4433163
    Abstract: Process for the production of 3,3-dimethylglutaric acid or its esters from dimedone. Dimedone is converted with ozone into an ozone-addition product. The latter is converted by hydrolysis into 3,3-dimethylglutaric acid or by alcoholysis into one of its esters.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: February 21, 1984
    Assignee: Lonza Ltd.
    Inventor: Pavel Lehky
  • Patent number: 4423018
    Abstract: A by-product stream from the production of adipic acid from cyclohexane, containing glutaric acid, succinic acid and adipic acid, is employed as a buffer in lime or limestone flue gas scrubbing for the removal of sulfur dioxide from combustion gases.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: December 27, 1983
    Assignee: Monsanto Company
    Inventors: J. Harvey Lester, Jr., Donald E. Danly
  • 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: 4340753
    Abstract: A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: July 20, 1982
    Assignee: General Electric Company
    Inventor: James A. Cella
  • Patent number: 4259524
    Abstract: A method for the oxidation of alicyclic hydrocarbons having substituent groups by the use of liquid nitrogen dioxide (N.sub.2 O.sub.4).
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: March 31, 1981
    Assignee: K.K. Pollution Preventing Research Laboratory
    Inventors: Wataru Ando, Ichiro Nakaoka