With Recycle Or Recovery Of Reaction Component Patents (Class 562/530)
  • 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
  • Patent number: 7847118
    Abstract: A process for continuous heterogeneously catalyzed partial dehydrogenation of at least one hydrocarbon to be dehydrogenated in a reactor which is manufactured from a composite material which consists, on its side in contact with the reaction chamber, of a steel B with specific elemental composition which, on its side facing away from the reaction chamber, either directly or via an intermediate layer of copper, or of nickel, or of copper and nickel, is plated onto a steel A with specific elemental composition, and also partial oxidations of the dehydrogenated hydrocarbon and the reactor itself.
    Type: Grant
    Filed: June 25, 2007
    Date of Patent: December 7, 2010
    Assignee: BASF SE
    Inventors: Claus Hechler, Wilhelm Ruppel, Martin Dieterle, Karl-Heinrich Klappert, Klaus Joachim Mueller-Engel, Goetz-Peter Schindler, Catharina Klanner, Hans-Juergen Bassler
  • Patent number: 7842846
    Abstract: A process for heterogeneously catalyzed partial dehydrogenation of a hydrocarbon, in which a reaction gas mixture input stream comprising the hydrocarbon to be dehydrogenated is conducted through a fixed catalyst bed disposed in a shaft and the reaction gas mixture input stream is obtained in the shaft by metering an input gas II comprising molecular oxygen upstream of the fixed catalyst bed into an input gas stream I which comprises molecular hydrogen and the hydrocarbon to be dehydrogenated and is flowing within the shaft toward the fixed catalyst bed.
    Type: Grant
    Filed: February 23, 2007
    Date of Patent: November 30, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Claus Hechler, Wilhelm Ruppel, Wolfgang Gerlinger, Wolfgang Schneider, Klaus Joachim Mueller-Engel
  • Patent number: 7790942
    Abstract: A process for continuous heterogeneously catalyzed partial dehydrogenation of at least one hydrocarbon to be dehydrogenated in a reactor which is manufactured from a steel with specific elemental composition on its side in contact with the reaction gas, and also partial oxidations of the dehydrogenated hydrocarbon and the reactor itself.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: September 7, 2010
    Assignee: BASF SE
    Inventors: Claus Hechler, Wilhelm Ruppel, Goetz-Peter Schindler, Catharina Klanner, Hans-Juergen Bassler, Martin Dieterle, Karl-Heinrich Klappert, Klaus Joachim Mueller-Engel
  • Patent number: 7141695
    Abstract: The invention relates to methods for producing substituted acrylic acid esters and to the use of the latter for producing substituted ?-amino acids, such as gabapentin and pregabalin. The substituted acrylic acid esters are produced by Wadsworth-Emmons olefination with trialkyl phosphonoacetate in the presence of alkali carbonate as the base, in an aqueous solvent.
    Type: Grant
    Filed: July 19, 2004
    Date of Patent: November 28, 2006
    Assignee: Grunenthal GmbH
    Inventors: Michael Thomas Przewosny, Claudia Pütz
  • 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: 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
  • Patent number: 6939991
    Abstract: In a process for preparing acrylic acid, an acrylic acid-containing product gas mixture obtained by catalytic gas phase partial oxidation of a C3 precursor of acrylic acid, after direct cooling with a quench liquid, is fractionally condensed in a separating column provided with internals, rising into itself with sidestream takeoff of crude acrylic acid, and the acrylic acid oligomers which form are dissociated and the resulting dissociation gas is subjected to a countercurrent rectification before it is recycled.
    Type: Grant
    Filed: June 20, 2003
    Date of Patent: September 6, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Thiel, Ulrich Hammon, Dieter Baumann, Jörg Heilek, Jürgen Schröder, Klaus Joachim Müller-Engel
  • Patent number: 6822117
    Abstract: The present invention relates to a process for the manufacture of adipic acid, more particularly of adipic acid crystals. It relates more specifically to a process for the treatment of the adipic acid crystals obtained on conclusion of crystallization, which consists in dispersing the adipic acid crystals collected on conclusion of crystallization in a liquid medium, in stirring the said liquid medium and in then separating the said crystals from the said liquid medium and optionally drying them. The form of the crystals is modified in order to obtain pebbles with a substantially smooth surface.
    Type: Grant
    Filed: April 22, 2002
    Date of Patent: November 23, 2004
    Assignee: Rhodia Fiber and Resin Intermediates
    Inventors: Albert Felix, Yves Roques
  • Patent number: 6781017
    Abstract: In a process for the preparation of acrolein or acrylic acid or a mixture thereof from propane, the propane is subjected, in a first reaction stage, to a partial dehydrogenation under heterogeneous catalysis to give propene, of the components contained in the product gas mixture formed in the first reaction stage other than propene and propane at least a portion of the molecular hydrogen present is then separated off from said mixture and the product gas mixture is then used for the preparation of acrolein and/or acrylic acid by gas-phase catalytic propylene oxidation, molecular nitrogen being present for diluting the reaction gas mixture during the propylene oxidation.
    Type: Grant
    Filed: December 13, 2002
    Date of Patent: August 24, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Otto Machhammer, Goetz-Peter Schindler, Andreas Tenten, Klaus Harth, Peter Zehner, Klaus Joachim Müller-Engel, Frank Rosowski, Frieder Borgmeier
  • Patent number: 6392092
    Abstract: A method for manufacturing 3-hydroxy-3-methylbutanoic acid (HMB) in commercially viable amounts is disclosed. The reaction mixture cycles through an external heat exchanger while the primary reactant is added in a warmer so as to control and maintain a low temperature for the reaction mixture. The manufacturing process herein disclosed increases yield while decreasing reaction time from the synthetic processes currently practiced.
    Type: Grant
    Filed: April 17, 2001
    Date of Patent: May 21, 2002
    Assignee: Met-Rx USA, Inc.
    Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
  • Patent number: 6376709
    Abstract: The subject invention relates to a process for the crystallization of di-carboxylic acids comprising dissolving the crude dicarboxylic acid at a temperature sufficient to dissolve the crude diacid in the solvent, whereby portion of the said solvent evaporates, increasing the concentration of the dicarboxylic acid in the said solution, transferring the said solution from the evaporator to a crystallizer, comprising a solid cylindrical impeller conforming to the shape of the crystallizer related by means of a cylindrical shaft attached to the spped motor, adding the additives selected from surfactants, buffer salts and/or acid salts or mixture thereof in the said evaporated solution in the said crystallizer, cooling the said mixture resulting in the formation of crystals of dicarboxylic acids, wherein the said crystallization takes place in the annular space between the impeller and the crystallizer wall.
    Type: Grant
    Filed: July 28, 1999
    Date of Patent: April 23, 2002
    Assignee: Chemintel (India) Private Limited
    Inventors: Sanjib Mall, Satyanand Chirravuri
  • Patent number: 6248922
    Abstract: A method for manufacturing 3-hydroxy-3-methylbutanoic acid (HMB) in commercially viable amounts is disclosed. The reaction mixture cycles through an external heat exchanger while the primary reactant is added in a warmer so as to control and maintain a low temperature for the reaction mixture. The manufacturing process herein disclosed increases yield while decreasing reaction time from the synthetic processes currently practiced.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: June 19, 2001
    Assignee: MET-RX USA Inc.
    Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
  • Patent number: 6090978
    Abstract: A method for manufacturing 3-hydroxy-3-methylbutanoic acid (HMB) in commercially viable amounts is disclosed. The reaction mixture cycles through an external heat exchanger while the primary reactant is added in a warmer so as to control and maintain a low temperature for the reaction mixture. The manufacturing process herein disclosed increases yield while decreasing reaction time from the synthetic processes currently practiced.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: July 18, 2000
    Assignee: MET-RX USA, Inc.
    Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
  • Patent number: 5471001
    Abstract: Crystallization of adipic acid using low intensity ultrasonic agitation during crystallization results in purer product that is more readily handled. Apparatus for carrying out the process is also disclosed.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: November 28, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Howard W. Anderson, John B. Carberry, Harold F. Staunton, Bhagya C. Sutradhar
  • Patent number: 5296639
    Abstract: A process for purification of adipic acid during crystallization by modifying the crystal morphology to decrease incorporation of impurities through the introduction of an effective amount of an additive to the crystallizing solution.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: March 22, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Diana L. Klug, Johannus H. Van Mil
  • 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: 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: 4442303
    Abstract: In one of its embodiments this invention provides a process for recovering C.sub.4 -C.sub.6 dicarboxylic acid components contained in a waste byproduct stream derived from a reaction system in which adipic acid is produced by nitric acid oxidation of cyclohexanone/cyclohexanol.An important aspect of the process is the esterification and extraction of the C.sub.4 -C.sub.6 dicarboxylic acids in the aqueous byproduct stream with a mixture of C.sub.1 -C.sub.3 alkanol and C.sub.6 -C.sub.20 alkanol, and the subsequent recovery of di(C.sub.6 -C.sub.20 alkyl) esters of succinic acid, glutaric acid and adipic acid.In a broader aspect this invention provides a process for recovery of water miscible organic acid components contained in an aqueous solution as C.sub.6 -C.sub.20 alkyl esters of the organic acids.
    Type: Grant
    Filed: December 9, 1980
    Date of Patent: April 10, 1984
    Assignee: El Paso Products Company
    Inventor: Samuel S. Mims
  • 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: 4321407
    Abstract: Process for reducing the color forming tendency of alkanedioic acid esters by contact with an alkali metal borohydride in the presence of water.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: March 23, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert A. Smiley
  • Patent number: 4254283
    Abstract: In the manufacture of adipic acid by nitric acid oxidation of cyclohexanol and cyclohexanone glutaric and succinic acids are recovered from the reaction by-product and waste stream by crystallizing adipic acid and succinic acid out of the stream leaving glutaric acid in the residue; forming succinic anhydride from the succinic acids so obtained; separating the succinic anhydride from the adipic acid by distillation thereby to recover succinic acid in anhydride form; and crystallizing, thereby to recover, the glutaric acid from the residue.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: March 3, 1981
    Assignee: Monsanto Company
    Inventor: George H. Mock
  • Patent number: 4230887
    Abstract: C.sub.2 -C.sub.6 monocarboxylic and dicarboxylic acids are scrubbed from gas phase mixtures of such acids and water by gas absorption techniques utilizing a liquid solvent comprising a polyoxyalkylene glycol or a monoalkyl or dialkyl ether thereof. The solvent enriched with the acid is subjected to distillation to recover a substantially anhydrous acid product.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: October 28, 1980
    Assignee: Celanese Corporation
    Inventors: William T. Mitchell, Phillip S. Snyder
  • Patent number: 4146730
    Abstract: A method for obtaining glutaric acid, succinic acid, and adipic acid from an acid mixture obtained as a by-product in the industry and comprising glutaric acid, succinic acid and adipic acid, which comprises the steps of: (1) contacting the acid mixture with urea of 1 to 2 moles per mole of the acid mixture, in solution, to deposit a urea-glutaric acid adduct so that the weight ratio of glutaric acid remaining in the solution to succinic acid is 1.2 or less when the adipic acid content is in the range of 0% by weight to 7% by weight and 1.
    Type: Grant
    Filed: December 15, 1976
    Date of Patent: March 27, 1979
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Joji Nishikido, Nobuhiro Tamura, Yohei Fukuoka