Patents Represented by Attorney M. Turken
  • Patent number: 4692546
    Abstract: Acyloxy aromatic carboxylic acids, e.g., 4-acetoxybenzoic acid, are prepared by oxidizing with oxygen an acyloxy aromatic ketone, e.g., 4-acetoxyacetophenone in the presence of manganese cations and a lower-carboxylic acid anhydride as catalyst and a co-reductant or promoter. The acyloxy aromatic ketone may be prepared by acylating a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone, which has the effect of "masking" the hydroxyl group of the ketone in a manner necessary to effect the subsequent transition-metal catalyzed oxidation of the ketone to the acyloxy aromatic carboxylic acid.
    Type: Grant
    Filed: September 25, 1985
    Date of Patent: September 8, 1987
    Assignee: Celanese Corporation
    Inventor: Kenneth G. Davenport
  • Patent number: 4675449
    Abstract: A process is provided for the production of 6-hydroxy-2-naphthones, e.g., 6-hydroxy-2-acetonaphthone, by contacting a 2-naphthyl carboxylate ester, e.g., 2-naphthyl acetate with at least 20 moles of hydrogen fluoride per mole of 2-naphthyl ester, at reaction temperatures, e.g., 0.degree. to 100.degree. C. for a period of reaction, e.g., 30 minutes to 8 hours sufficient to produce the desired amount of 6-hydroxy-2-naphthone. The process may utilize a carboxylic acid or anhydride, e.g., acetic acid or anhydride as an additive for the purpose of further increasing the regioselectivity of the 6-hydroxy-2-naphthone product. The process is capable of being carried out at a conversion of 2-naphthyl ester of at least 90% and a regioselectivity to 6-hydroxy-2-naphthone of at least 90 mol %.
    Type: Grant
    Filed: June 3, 1986
    Date of Patent: June 23, 1987
    Assignee: Celanese Corporation
    Inventor: Kenneth G. Davenport
  • Patent number: 4665215
    Abstract: A process is provided for the production of 4-acetoxybenzoic acid by subjecting phenyl acetate to a Fries rearrangement or phenol and an acetylating agent to a Friedel-Crafts acetylation to form 4-hydroxyacetophenone which is then acetylated with an acetylating agent such as acetic anhydride to form 4-acetoxyacetophenone. The 4-acetoxyacetophenone is then oxidized with oxygen in the presence of manganese cations and acetic acid as catalysts and a co-reductant or promoter to form 4-acetoxybenzoic acid. The acetylation of the 4-hydroxyacetophenone has the effect of "masking" the hydroxyl group of the latter compound in a manner necessary to effect the subsequent oxidation of the ketone group of the 4-acetoxyacetophenone.
    Type: Grant
    Filed: September 25, 1985
    Date of Patent: May 12, 1987
    Assignee: Celanese Corporation
    Inventor: Kenneth G. Davenport
  • Patent number: 4663485
    Abstract: A process is provided for the distillation of a composition containing 4-hydroxyacetophenone and hydrogen fluoride in the presence of an alkane assisting solvent having from 4 to 16 carbon atoms e.g. n-hexane or n-octane. The process is carried out to obtain an overhead vapor containing alkane solvent and most of the hydrogen fluoride in the feed, and a liquid residue containing most of the 4-hydroxyacetophenone in the feed. The overhead vapor is condensed to form two immiscible phases, one containing a preponderance of hydrogen fluoride and the other a preponderance of alkane solvent, with the latter phase being returned to the distillation as reflux. The liquid residue also separates into two immiscible layers, one containing most of the 4-hydroxyacetophenone in the feed which is recovered and the other a preponderance of alkane solvent.
    Type: Grant
    Filed: July 22, 1986
    Date of Patent: May 5, 1987
    Assignee: Celanese Corporation
    Inventors: Carl D. Murphy, Donna L. Keene, Daniel D. Lindley
  • Patent number: 4652683
    Abstract: A process is provided for the production of 2-hydroxyphenyl lower alkyl ketones, e.g. 2-hydroxyacetophenone, by reacting phenol and a lower alkanoic acid, e.g. acetic acid or an ester of phenol and a lower alkanoic acid, e.g. phenyl acetate, in the presence of a silicalite catalyst containing about 700 to 14000 ppm of alumina, which has been calcined at least once from the as synthesized form. The reaction is preferably conducted in the vapor phase in the presence of an inert gas such as nitrogen.
    Type: Grant
    Filed: December 2, 1985
    Date of Patent: March 24, 1987
    Assignee: Celanese Corporation
    Inventors: Ioan Nicolau, Adolfo Aguilo
  • Patent number: 4607125
    Abstract: A process of acylating a monocyclic phenolic reactant, e.g. phenol to a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, by contacting the phenolic reactant with about 0.4 to 0.8 moles of a carboxylic acid anhydride, e.g. acetic anhydride as acylating agent per mole of phenolic reactant of in the presence of a Friedel-Crafts catalyst, e.g. hydrogen fluoride. The process generally results in phenolic reactant conversions of at least about 80% and reaction selectivities to hydroxy aromatic ketone of at least about 70%.
    Type: Grant
    Filed: April 8, 1985
    Date of Patent: August 19, 1986
    Assignee: Celanese Corporation
    Inventor: Graham N. Mott
  • Patent number: 4593125
    Abstract: Naphthalene substituted in the 2- or .beta.-position with an electron-donating substituent can be acylated with high regioselectivity in the 6-position by using an acylating agent in substantially anhydrous hydrogen fluoride which functions both as catalyst and solvent.
    Type: Grant
    Filed: March 13, 1985
    Date of Patent: June 3, 1986
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, H. Clay Linstid, III
  • Patent number: 4568763
    Abstract: N-acyl-acyloxy aromatic amines, e.g. 4-acetoxyacetanilide (AAA), are prepared by reacting a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, with hydroxylamine or a hydroxylamine salt and a base to obtain the ketoxime of the ketone, e.g. 4-hydroxyacetophenone oxime, and then subjecting the ketoxime to a Beckmann rearrangement and accompanying acylation by contacting the ketoxime with a carboxylic acid anhydride and a Beckmann rearrangement catalyst to form the N-acyl-acyloxy aromatic amine.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: February 4, 1986
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, Charles B. Hilton
  • Patent number: 4560789
    Abstract: 4-Acetoxyacetanilide is produced by subjecting phenyl acetate to a Fries rearrangement or phenol and an acetylating agent to a Friedel-Crafts acetylation to form 4-hydroxyacetophenone which is then reacted with hydroxylamine or a hydroxylamine salt to form 4-hydroxyacetophenone oxime. The oxime is then subjected to a Beckmann rearrangement and accompanying acetylation with acetic anhydride to form the 4-acetoxyacetanilide.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: December 24, 1985
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, Charles B. Hilton
  • Patent number: 4542231
    Abstract: New and improved compositions are described of ethylenically unsaturated organic compounds capable of addition polymerization stabilized from unintentional or premature polymerization in the liquid phase by the addition of the combination cerium compounds which are soluble in the ethylenically unsaturated organic compounds and phenolic type inhibitors.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: September 17, 1985
    Assignee: Celanese Corporation
    Inventors: Edward F. Dougherty, Mark O. Scates
  • Patent number: 4529550
    Abstract: Improvements in efficiencies and yields are achieved in the production of a saturated aliphatic monocarboxylic acid containing 5 to 9 carbon atoms from its corresponding aldehyde by rapidly hydrolyzing the anhydride of the monocarboxylic acid formed in the oxidation. The hydrolysis is accomplished by contacting the anhydride with water at a temperature from about 130.degree. C. to about 215.degree. C. and at a pressure under which the water is maintained in the liquid state to convert the anhydride to its corresponding acid.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: July 16, 1985
    Assignee: Celanese Corporation
    Inventors: Olan S. Fruchey, James S. Alder
  • Patent number: 4524217
    Abstract: N-acyl-hydroxy aromatic amines, e.g. N-acetyl-para-aminophenol (APAP), are prepared by reacting a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, with a hydroxylamine salt and a base to obtain the ketoxime of the ketone, e.g. 4-hydroxyacetophenone oxime, and then subjecting the ketoxime to a Beckmann rearrangement in the presence of a catalyst to form the N-acyl-hydroxy aromatic amine.
    Type: Grant
    Filed: June 8, 1984
    Date of Patent: June 18, 1985
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, Charles B. Hilton
  • Patent number: 4507495
    Abstract: In the process of producing ethyl acrylate by the reaction of ethylene and acrylic acid in the presence of sulfuric acid, using phenolic type inhibitors, soluble manganese or cerium salts are additionally utilized.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: March 26, 1985
    Assignee: Celanese Corporation
    Inventors: Edward F. Dougherty, Mark O. Scates, James L. Paul
  • Patent number: 4500464
    Abstract: A process is described for removing copper and manganese catalysts from an organic phase comprising a saturated aliphatic monocarboxylic acid containing 5 to 9 carbon atoms by extracting the catalysts with aqueous formic acid.
    Type: Grant
    Filed: February 15, 1983
    Date of Patent: February 19, 1985
    Assignee: Celanese Corporation
    Inventor: Olan S. Fruchey
  • Patent number: 4496488
    Abstract: A process is described for removing copper and manganese ions from a saturated aliphatic monocarboxylic acid containing from 6 to 9 carbon atoms by extracting the metal ions into an aqueous layer in the presence of an extractant acid, the hydrogen of which can be replaced by both metal ions. The metal ion-containing aqueous layer may then be separated from the monocarboxylic acid-containing organic layer, with the latter layer having a substantially reduced content of copper and manganese ions.
    Type: Grant
    Filed: March 30, 1983
    Date of Patent: January 29, 1985
    Assignee: Celanese Corporation
    Inventor: Clarence J. Duey, Jr.
  • Patent number: 4487720
    Abstract: In the purification of the corresponding acid products obtained by oxidizing C.sub.5 to C.sub.9 organic saturated aliphatic aldehydes in the presence of a combination of manganese and copper catalysts soluble in said acids, the liquid acid reaction product is separated from the soluble catalysts by distillation in the presence of a sufficient amount of oxygen to prevent copper from plating out on the distillation equipment.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: December 11, 1984
    Assignee: Celanese Corporation
    Inventor: Olan S. Fruchey
  • Patent number: 4485046
    Abstract: A process for the production of cupric and manganous alkanoates containing from 6 to 9 carbon atoms is described. This process comprises first thermally decomposing a mixture of cupric and manganous oxalates, obtained from the oxidation of C.sub.6 to C.sub.9 aldehydes to the corresponding acids using a mixture of copper and manganese compounds soluble in the acid product as the catalyst, in the presence of an organic saturated aliphatic monocarboxylic acid containing from 6 to 9 carbon atoms, and in the absence of oxygen, to produce manganous alkanoate and metallic copper. The metallic copper is then oxidized with oxygen to copper in the cupric form, which reacts with the organic saturated aliphatic monocarboxylic acid present to produce cupric alkanoate. The mixtures of cupric and manganous alkanoates obtained can be used as oxidation catalysts, and in fact may be recycled to the reaction sphere in which the C.sub.6 -C.sub.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: November 27, 1984
    Assignee: Celanese Corporation
    Inventor: Olan S. Fruchey
  • Patent number: 4485047
    Abstract: A process is described for recovering water soluble copper and manganese compounds from an aqueous solution by reacting the copper and manganese compounds with saturated aliphatic monocarboxylic acids containing 5 to 9 carbon atoms at elevated temperatures forming cupric and manganous alkanoates containing 5 to 9 carbon atoms, and simultaneously removing the water by distillation in the presence of sufficient oxygen-containing gas to prevent the copper from plating on the distillation equipment, recovering the cupric and manganese alkanoates.
    Type: Grant
    Filed: February 15, 1983
    Date of Patent: November 27, 1984
    Assignee: Celanese Corporation
    Inventors: Olan S. Fruchey, Edward M. de la Garza
  • Patent number: 4480122
    Abstract: A process for producing methyl formate is described by the dehydrogenation of methanol over a catalyst produced by reducing a precursor comprising copper oxide and a spinel structure support comprising the oxides of zinc and aluminum, said precursor containing 10 to 80 percent copper.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: October 30, 1984
    Assignee: Celanese Corporation
    Inventors: Theodore Horlenko, Adolfo Aguilo
  • Patent number: 4480138
    Abstract: In hydroformylating an olefinic compound to produce an aldehyde derivative thereof employing as a catalyst a complex of a Group VIII metal and an organic ligand dissolved in an inert liquid reaction solvent, improvements in production efficiencies and product separation from reaction product in solution are achieved in using as the inert liquid reaction medium, a saturated alpha-olefin oligomer free of naphthenic and aromatic hydrocarbons having the appropriate viscosity, average molecular weights and flash point properties which are required in the hydroformylating reaction.
    Type: Grant
    Filed: October 12, 1982
    Date of Patent: October 30, 1984
    Assignee: Celanese Corporation
    Inventors: E. B. Hackman, L. D. Zeagler