Preparing Esters By Oxidation Patents (Class 560/131)
  • Patent number: 11078136
    Abstract: Provided is a process for converting an alkane to an alkene. The process comprises (a) contacting the alkane and either (i) an oxidizing electrophile comprising a main group element in oxidized form, or (ii) an oxidant and a reduced form of the oxidizing electrophile, in a liquid medium comprising an oxygen acid and optionally one or more additives selected from a non-oxidizable liquid, a salt additive, a Lewis acid, and water, to provide an oxidized intermediate and a reduced form of the oxidizing electrophile; (b) optionally separating the oxidized intermediate and the reduced form of the oxidizing electrophile; and (c) performing an elimination reaction on the oxidized intermediate to provide the alkene and the oxygen acid.
    Type: Grant
    Filed: May 25, 2018
    Date of Patent: August 3, 2021
    Assignees: The Scripps Research Institute, Hyconix, Inc.
    Inventors: Roy A. Periana, Brian G. Hashiguchi, Michael M. Konnick
  • Patent number: 8207365
    Abstract: The present disclosure provides a polymerizable compound of the formula (I) where the R1, R2, R?1, R?2, X1 to X8, Y1, Y2, M and L have any of values as defined in the specification. The disclosure also provides an oligomer, a homo-polymer, or a co-polymer of compound of the formula (I). The disclosure also provides methods for preparing the compound of the formula (I) and methods for preparing polymers of the compound of the formula (I), and to methods and intermediates useful for preparing them. The disclosure also provides methods for the use of the polymers of formula (I) as chiral catalysts in enantioselective preparative processes.
    Type: Grant
    Filed: March 13, 2006
    Date of Patent: June 26, 2012
    Assignee: Georgia Tech Research Corporation
    Inventors: Xiaolai Zheng, Michael Johannes Holbach, Marcus Weck, Christopher W. Jones
  • Patent number: 6958407
    Abstract: A phenyl ester is produced by allowing benzene, a carboxylic acid and molecular oxygen to react with each other in the presence of a catalyst comprising (A) palladium, (B) at least one element selected from elements of groups 13, 14, 15, and 16 and the fourth to sixth periods of the periodic table, and (C) at least one element selected from elements of groups 3, 4 and lanthanoid elements of the periodic table. Preferably, element (B) is selected from elements of group 16 and the fourth to sixth periods of the periodic table, and element (C) is contained in a metal oxide form in the catalyst. The catalytic activity can be maintained at a high level, and a phenyl ester is stably produced. The phenyl ester can be converted to phenol by a conventional procedure.
    Type: Grant
    Filed: November 4, 2004
    Date of Patent: October 25, 2005
    Assignee: Tosoh Corporation
    Inventors: Yoshihiko Mori, Takao Doi, Tetsuo Asakawa, Takanori Miyake
  • Patent number: 6956134
    Abstract: Feeds comprising methanol, dimethyl ether or a mixture of the two are oxidized by contacting the feed with an oxygen-containing gas and a supported heteropolyacid catalyst containing molybdenum or molybdenum and vanadium. The primary products are methylal (dimethoxymethane) and methyl formate. Production of dimethyl ether from methanol can be inhibited by partial deactivation of acid sites on the Keggin catalyst.
    Type: Grant
    Filed: January 8, 2004
    Date of Patent: October 18, 2005
    Assignee: The Regents of the University of California
    Inventors: Haichao Liu, Enrique Iglesia
  • Patent number: 6831195
    Abstract: A method for producing an organic acid and/or an organic acid ester which utilizes a steam system permitting stable production of an organic acid and/or an organic acid ester and realizing a high thermal efficiency constantly relative to the waste heat generated in the process of the production is provided. More particularly, this invention concerns a method for the production of an organic acid and/or an organic acid ester, wherein heat generated in the process for producing an organic acid and/or an organic acid ester is recovered in the form of steam, and the steam is used in any of the following forms: {circle around (1)} thermal energy, {circle around (2)} dynamic energy, and {circle around (3)} electrical energy in the process for producing an organic acid and/or an organic acid ester.
    Type: Grant
    Filed: August 21, 2002
    Date of Patent: December 14, 2004
    Assignee: Nippon Shokubai, Co., LTD
    Inventors: Takeshi Nishimura, Tetsuji Mitsumoto, Kazuhiko Sakamoto, Hidefumi Haramaki
  • Patent number: 6476253
    Abstract: The present invention relates to a process for preparing monoacetylated hydroquinone compounds of the formula I, to the novel final products of the process and to a process for preparing the precursors.
    Type: Grant
    Filed: October 3, 2000
    Date of Patent: November 5, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Karin Schein, Kai-Uwe Baldenius, Wolfgang Siegel, Rainer Stürmer, Detlef Ruff, Hagen Jaedicke
  • Patent number: 6342620
    Abstract: A phenyl carboxylate is produced by allowing benzene, a carboxylic acid and molecular oxygen to react with each other in the coexistence of a palladium catalyst with at least one additive selected from alcohols, aldehydes, cyclic hydrocarbons and formic acid. By using the additive, the reduction of catalytic activity of the palladium catalyst with time is minimized.
    Type: Grant
    Filed: March 29, 2000
    Date of Patent: January 29, 2002
    Assignee: Tosoh Corporation
    Inventor: Yoshihiko Mori
  • Patent number: 6215029
    Abstract: A process for the preparation of halohydroxydiphenyl compounds useful for protecting organic materials and articles from microorganisms, of the formula by acylation of a halogenated benzene compound (first stage), etherification of the acylated compound with a halogenated phenol compound (second stage), oxidation of the etherified compound (third stage) and hydrolysis of the oxidized compound in a fourth stage, according to the following reaction scheme: in which R1 and R2 independently of one another are F, Cl or Br; R3 and R4 independently of one another are hydrogen; or C1-C4alkyl; m is 1 to 3; and n is 1 or 2.
    Type: Grant
    Filed: June 9, 1999
    Date of Patent: April 10, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Urs Burckhardt, Armando Di Teodoro, Werner Hölzl, Dieter Reinehr, Rudolf Zink, Hanspeter Sauter, Uwe Gronde
  • Patent number: 5670695
    Abstract: The present invention relates to a process for the preparation of 1,8-diacetoxy-3-carboxyanthraquinone, also known as diacerein, via aloin acetylation, oxidation of the acetylated product, and purification of the raw diacerein obtained by means of crystallization from 2-methoxyethanol or N,N-dimethylacetamide and optionally by dissolution of the corresponding salt with triethylamine in methylene chloride, followed by removal of the insoluble residue.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: September 23, 1997
    Assignee: Laboratoire Medidom S.A.
    Inventor: Guido Di Napoli
  • Patent number: 5557008
    Abstract: A one pot process for the perfluoroalkylation and/or perfluoroacyloxylation of organic substrates is provided. The process comprises contacting a substrate with a perfluoroalkanoic anhydride in the presence of an inorganic peroxygen compound at a temperature of greater than 10.degree. C. Substrates that can be perfluoroalkylated and/or perfluoroacyloxylated include alkylbenzenes, halogenated aromatic compounds, alkoxybenzenes, aryl benzenes, and aromatic and aliphatic disulphides. Preferably, the perfluoroalkanoic anhydride is trifluoroacetic anhydride and the inorganic peroxygen compound is sodium percarbonate.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: September 17, 1996
    Assignee: Solvay Interox Limited
    Inventors: Craig W. Jones, William R. Sanderson, John P. Sankey
  • Patent number: 5256163
    Abstract: The present invention provides a flow liquid-phase chemical reaction system in which a high pressure reservoir unit holds a solvent solution which contains an organic reactant and a gas reactant. The quantity of gas reactant dissolved in the solvent solution is determined by the level of gas reactant vapor pressure in the reservoir unit. The solvent solution is passed through a solid catalyst reactor unit to achieve a selective reaction between the two reactant components of the solvent solution.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: October 26, 1993
    Assignees: Philip Morris Incorporated, Philip Morris Products Inc.
    Inventors: Robert L. Augustine, Glen Wolosh
  • Patent number: 5214192
    Abstract: Diacetoxyatene compounds are obtained by reacting a perborate such as sodium perborate monohydrate or tetrahydrate and acetic acid with an iodoarene compound under mild conditions, such as 40 to 50.degree. C. The iodoarene can be further substituted by a wide range of substituents, such as halo, nitro, alkyl, alkoxy or carbosylic acid, in any position around the nucleus, except that electron withdrawing substituents occupy meta positions only. The invention process thus enables a wide range of substituted diacetoxyarene compounds to be produced using widely available and easily handled materials under mild operating conditions.
    Type: Grant
    Filed: October 2, 1991
    Date of Patent: May 25, 1993
    Assignee: Interox Chemicals Limited
    Inventors: Alexander McKillop, Duncan Kemp
  • Patent number: 4990660
    Abstract: Aromatic hydroxycarboxylic acids of the formula(HO--).sub.n A--COOHwhere n is 1 or 2 and A is a radical from the benzene, naphthalene, biphenyl, diphenyl ether, diphenyl sulfide or diphenyl sulfone series, are prepared by a process in which an acylated aromatic compound of the formula(R.sup.1 --CO--O--).sub.n A--CO--R.sup.2where R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl and n and A each have the abovementioned meanings, is oxidized with oxygen in the presence of a catalyst and of a solvent at from 20.degree. to 250.degree. C. to give a carboxylic acid of the formula(R.sup.1 --CO--O--).sub.n A--COOHwhere R.sup.1, n and A have the abovementioned meanings, and the acyl group or groups is or are then eliminated.
    Type: Grant
    Filed: December 21, 1988
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Ulrich Eichenauer
  • Patent number: 4952721
    Abstract: A process is disclosed for the oxidation of esters of para- and meta-methyl-substituted phenols to the corresponding aromatic carboxylic acid in the presence of a promoter comprising an anhydride of a lower aliphatic carboxylic acid and a heavy metal catalyst with or without the presence of bromine. The resulting carboxylic acids are useful in liquid crystal polymers and polymers useful in engineering plastics.
    Type: Grant
    Filed: March 8, 1989
    Date of Patent: August 28, 1990
    Assignee: Amoco Corporation
    Inventor: Kristi A. Fjare
  • Patent number: 4877898
    Abstract: A process for the one step esterification of aldehydes and alcohols comprises the steps of combining an aldehyde with an alcohol, in the presence of oxygen and in contact with a catalyst having the general formulaPdTe.sub.a Zn.sub.d E.sub.ewhereE is one or more metals from the group consisting of group IA, IIA, IVA, VIIB or VIII metals, As or Sb; anda, d and e are from about 0 to 3 with the proviso that at least d or e.noteq.0.
    Type: Grant
    Filed: June 12, 1986
    Date of Patent: October 31, 1989
    Assignee: The Standard Oil Company
    Inventors: Christos Paparizos, Wilfrid G. Shaw, James L. Callahan
  • Patent number: 4655974
    Abstract: A process is described for the manufacture of aryl esters such as phenyl esters by liquid phase reaction of an aromatic compound such as benzene with molecular oxygen in the presence of a carboxylic acid preferably having 6 or more carbon atoms over a catalyst composed essentially of a compound of palladium and an antimony compound wherein the aromatic compound is added continuously to the reaction and water formed in the reaction is rapidly and continuously removed from the reaction zone.
    Type: Grant
    Filed: April 4, 1984
    Date of Patent: April 7, 1987
    Inventors: Anil B. Goel, Robert A. Grimm
  • Patent number: 4526722
    Abstract: A process is described for the manufacture of diacyloxy aromatic hydrocarbons by the liquid phase reaction of an aromatic hydrocarbon or a monoacyloxy aromatic hydrocarbon with molecular oxygen in the presence of a carboxylic acid over a catalyst composed of a compound of palladium, a compound of antimony and a compound of at least one member selected from the group consisting of an alkali metal, chromium, zinc, antimony and tin wherein the water formed in the reaction is rapidly and continuously removed from the reaction as it forms.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: July 2, 1985
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4515983
    Abstract: A process for the preparation of phenyl esters and phenol in which a feed mixture of benzene, molecular oxygen, a lower carboxylic acid and optionally water is passed over a catalyst composed of a palladium carboxylate, an antimony carboxylate and a chromium carboxylate is described.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: May 7, 1985
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Michael E. Pettiford
  • Patent number: 4512927
    Abstract: A process for the preparation of naphthyl or indene carboxylates by reaction of tetralin or indane with oxygen and a carboxylic acid in the presence of a catalyst comprising palladium is described.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: April 23, 1985
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4507243
    Abstract: The oxidation process for the manufacture of aryl esters comprising contacting the reaction mixture of an aromatic hydrocarbon, a carboxylic acid and molecular oxygen in the liquid phase at an elevated temperature with a catalyst composed of palladium or a compound of palladium, a chromium compound and a compound of at least one member selected from the group consisting of zinc, manganese, tin, cobalt and nickel is described.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: March 26, 1985
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Peter E. Throckmorton
  • Patent number: 4504672
    Abstract: Equimolar amounts of phenol and formaldehyde may be prepared from oxygen and toluene. The catalytic oxidation of toluene, when carried out in the presence of acetic anhydride, forms phenyl acetate and methylene diacetate. Pyrolysis of these two intermediates yields phenol and formaldehyde.Significant improvements in this process are achieved when the first stage of the reaction is carried out in the presence of MoO.sub.3.In a further embodiment of this invention it has been found that Group VIII dithiosemibenzil compounds, particularly nickel dithiosemibenzil, serves as a superior promoter for the toluene oxidation reaction.In still a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for the toluene oxidation reaction.In a like manner, hydroquinone or resorcinol may be obtained from cresyl acetates.
    Type: Grant
    Filed: November 5, 1980
    Date of Patent: March 12, 1985
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: 4499298
    Abstract: A process is described for the preparation of aryl esters such as benzyl acetate by reacting an aryl alkyl compound such as toluene with a carboxylic acid such as acetic acid and oxygen in the presence of a catalytically effective amount of a catalyst comprising palladium metal, gold metal and a metal of Group VA of the Periodic Table of the Elements such as bismuth.
    Type: Grant
    Filed: December 20, 1979
    Date of Patent: February 12, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventors: John A. Scheben, James A. Hinnenkamp
  • Patent number: 4469883
    Abstract: Acetoxyacetophenone is the predominant product when phenyl acetate, acetic acid and acetic anhydride are reacted in the presence of palladium and a gas mixture containing an inert gas and more than 13 vol. % oxygen. Secondary products are hydroxyacetophenone and phenylene diacetates. The meta isomers predominate when a metal acetate is present in the reaction mixture. Mineral acids cause shift to ortho isomers.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: September 4, 1984
    Assignee: Sun Tech, Inc.
    Inventors: Chao-Yang Hsu, James E. Lyons
  • Patent number: 4465633
    Abstract: A process is described for the manufacture of aryl esters such as phenyl esters by liquid phase reaction of an aromatic compound such as benzene with molecular oxygen in the presence of a carboxylic acid preferably having 6 or more carbon atoms over a catalyst composed essentially of a compound of palladium, a compound of antimony and a compound of at least one member selected from the group consisting of chromium, cobalt, nickel, manganese, iron, and tin wherein the aromatic compound is added continuously to the reaction and water formed in the reaction is rapidly and continuously removed from the reaction zone.
    Type: Grant
    Filed: November 15, 1982
    Date of Patent: August 14, 1984
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Peter E. Throckmorton
  • Patent number: 4464303
    Abstract: An improved process for the manufacture of higher aromatic hydrocarbon esters, such as naphthyl esters, by liquid phase reaction of the higher aromatic hydrocarbon compound with molecular oxygen in the presence of a higher carboxylic acid over a catalyst composed essentially of a compound of palladium and an antimony compound wherein the aromatic compound is dissolved in an inert solvent and is added continuously to the reaction zone and water formed in the reaction is rapidly and continuously removed from the reaction zone.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: August 7, 1984
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4370497
    Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.
    Type: Grant
    Filed: August 7, 1980
    Date of Patent: January 25, 1983
    Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
  • Patent number: 4360691
    Abstract: Malonic anhydride and substituted malonic anhydrides are prepared by ozonolysis of the enol-lactone dimers of ketenes. The resulting malonic anhydrides can be hydrolyzed with water to form the corresponding acid, reacted with an alcohol to yield the monoester, or reacted with an amine to yield the monoamide.
    Type: Grant
    Filed: August 25, 1980
    Date of Patent: November 23, 1982
    Assignee: The Regents of the University of California
    Inventor: Charles L. Perrin
  • Patent number: 4336396
    Abstract: This invention relates to a process for the preparation of 4-[2-(dimethylamino)-ethoxy]-2-methyl-5-(1-methylethyl)-phenol esters (I) and their salts with organic and inorganic acids comprising the reaction of thymol with a salt of an 1-halo-dimethylaminoethane to obtain ethylamine-N,N-dimethyl-2-(thymyloxy) (II), the subsequent reaction of (II) with an acylating agent according to the Friedel and Kraft reaction to obtain 4-[2-(dimethylamino)-ethoxy]-2-methyl-5-(1-methylethyl)-1-acyl-benzene (III) and the oxidation of (III) to obtain the products (I) which, if desired, may be transformed in their salts with organic or inorganic acids.This process allows to obtain the products (I) in high quality and quantity without isolating any intermediate product.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: June 22, 1982
    Assignee: Blasinachim S.p.A.
    Inventors: Claudio Giordano, Aldo Belli
  • Patent number: 4332963
    Abstract: Paraphenylene diacetate is the predominant product when phenylacetate, acetic acid and acetic anhydride are reacted in the presence of palladium and a gas mixture containing an inert gas and no more than 13 vol.% oxygen.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: June 1, 1982
    Assignee: Sun Tech, Inc.
    Inventors: James E. Lyons, Chao-Yang Hsu
  • Patent number: 4328361
    Abstract: A process is disclosed for converting p-isopropenylphenol and derivatives thereof and, more particularly, oligomers of p-isopropenylphenol and derivatives thereof, to hydroquinone via monomeric intermediates [e.g. p-(2-haloisopropyl)phenol in the case of p-isopropenylphenol and oligomers thereof]. The process involves reacting the starting materials with a hydrogen halide (e.g. gaseous hydrogen chloride) in the presence of an organic solvent and subjecting the product so obtained to oxidation with hydrogen peroxide or an organic hydroperoxide.
    Type: Grant
    Filed: January 16, 1981
    Date of Patent: May 4, 1982
    Assignee: The Upjohn Company
    Inventor: Shenghong A. Dai
  • Patent number: 4311850
    Abstract: Muconic acid monoesters of alkanediols of 2-6 carbons and of phenol are prepared by copper (II) oxidative cleavage of phenols, catechols or orthobenzoquinones. The products are useful as comonomers in polyamides and other polymers. The alkanediol or phenol is introduced into the copper (II) reactant or catalyst.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: January 19, 1982
    Assignee: Allied Corporation
    Inventors: Timothy R. Demmin, Milorad M. Rogic
  • Patent number: 4286068
    Abstract: A process for oxidizing organic substrates such as ketones and ethylenically unsaturated compounds. The substrate is contacted with aqueous hydrogen peroxide in a solution or in a two-phase liquid system, in the presence of a polymeric catalyst containing chemically bonded arsenic. This process can lead to lactones or hydroxy acids from cyclic ketones or to esters or mixtures of alcohol and carboxylic acid from open chain ketones. Unsaturated compounds afford epoxides and/or diols. Preparations of certain polymers substituted by arsenic groups, particularly from polystyrene, poly(vinylpyridine) and copolymers thereof, useful as catalysts in such oxidation process, are described. For example, polystyrene is brominated, bromine therein is replaced by lithium and the resulting lithiated polymer is converted into a polymer containing an arsenic group, such as arsono, --As(O)(OH).sub.2, as substituent group, by reaction with arsine triethoxide followed by oxidation and hydrolysis by aqueous hydrogen peroxide.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: August 25, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Frank Mares, Stephen E. Jacobson
  • Patent number: 4260808
    Abstract: Equimolar amounts of phenol and formaldehyde may be prepared from oxygen and toluene. The catalytic oxidation of toluene, when carried out in the presence of acetic anhydride, forms phenyl acetate and methylene diacetate. Pyrolysis of these two intermediates yields phenol and formaldehyde.Significant improvements in this process are achieved when the first stage of the reaction is carried out in the presence of MoO.sub.3.In a further embodiment of this invention it has been found that Group VIII dithiosemibenzil compounds, particularly nickel dithiosemibenzil, serves as a superior promoter for the toluene oxidation reaction.In still a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for the toluene oxidation reaction.In a like manner, hydroquinone or resorcinol may be obtained from cresyl acetates.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: April 7, 1981
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: 4249019
    Abstract: A carboxylic ester is produced in one step in a high yield and with a high selectivity by reacting an aldehyde with an alcohol in the presence of oxygen by using a catalyst comprising (I) palladium, (II) at least one compound selected from the group consisting of lead compounds, thallium compounds and mercury compounds and (III) at least one compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.
    Type: Grant
    Filed: November 13, 1978
    Date of Patent: February 3, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
  • Patent number: 4244881
    Abstract: Alpha-naphthol esters of aliphatic carboxylic acids are prepared by oxidation of naphthalene in the presence of cobalt compounds.
    Type: Grant
    Filed: March 28, 1979
    Date of Patent: January 13, 1981
    Assignee: Montedison S.p.A.
    Inventors: Claudio Giordano, Aldo Belli, Francesco Minisci
  • Patent number: 4237309
    Abstract: The oxidation of methyl benzenes with air or oxygen in the presence of acetic anhydride, benzaldehyde and an acid catalyst under mild reaction conditions yields a phenolic acetate and formaldehyde or paraformaldehyde when the ratio of acetic anhydride to methyl benzene is adjusted to provide the selective formation of the phenolic acetate and formaldehyde or paraformaldehyde. In this process, it is essential that the flow of air or oxygen through the reaction medium be maintained at a sufficient rate to provide for the continuous removal of formaldehyde as it is formed. The formaldehyde may then be recovered in the form of paraformaldehyde.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: December 2, 1980
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: 4237310
    Abstract: The oxidation of methyl benzenes, such as toluene, with air or oxygen in the presence of acetic anhydride and sulfuric acid catalyst to form a phenolic acetate and methylene diacetate may be carried out under mild conditions when small amounts of benzaldehyde are added to the reaction.The resulting acetates may then be pyrolyzed to yield phenolic compounds and formaldehyde, respectively.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: December 2, 1980
    Assignee: Suntech, Inc.
    Inventors: George Suld, James E. Lyons, Robert W. Shinn
  • Patent number: 4233460
    Abstract: An extremely mild, oxidative process for converting alkoxyalkanols to the corresponding acids is disclosed which comprises reacting the alcohol with an alkali metal hydroxide and tert-butyl hydroperoxide in the presence of a catalytic amount of palladium.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: November 11, 1980
    Assignee: Shell Oil Company
    Inventors: Carl L. Willis, Lynn H. Slaugh
  • Patent number: 4229587
    Abstract: A process for preparing aromatic esters by oxyacylation which comprises contacting benzene or an aryl alkyl compound with a carboxylic acid and oxygen in the vapor phase in the presence of a catalytically effective amount of a catalyst comprising an oxide of uranium and at least one oxide selected from the group consisting of arsenic, antimony and bismuth oxide.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: October 21, 1980
    Assignee: National Distillers and Chemical Corporation
    Inventor: Jawad H. Murib
  • Patent number: 4227012
    Abstract: Oxidation of methyl benzenes with air or oxygen to form a phenolic acetate and formaldehyde or methylene diacetate may be carried out in the presence of acetic acid, phosphorus pentoxide, benzaldehyde and an acid catalyst. The resulting acetates may then be pyrolyzed to yield phenolic compounds and formaldehyde, respectively.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: October 7, 1980
    Assignee: Suntech, Inc.
    Inventors: George Suld, James E. Lyons, Robert W. Shinn
  • Patent number: 4225728
    Abstract: Equimolar amounts of vinyl acetate and phenol may be prepared by oxidation of ethyl benzene. The catalytic oxidation, of ethyl benzene, when carried out in the presence of acetic anhydride, forms phenyl acetate and ethylidene diacetate. Pyrolysis of these two intermediates yields vinyl acetate and phenol.In a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for this oxidation reaction.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: September 30, 1980
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: 4191839
    Abstract: A highly selective, one-step conversion of toluene to benzylidene diacetate is provided by the reaction of toluene with O.sub.2 and acetic anhydride in the presence of an acid catalyst. No metal catalysts are required.
    Type: Grant
    Filed: March 27, 1978
    Date of Patent: March 4, 1980
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, Robert W. Shinn, George Suld
  • Patent number: 4156783
    Abstract: Benzylidene diacetate may be converted to phenyl acetate and methylene diacetate by an acid-catalyzed reaction in the presence of oxygen or air, and acetic anhydride, at elevated temperatures and pressures.
    Type: Grant
    Filed: March 27, 1978
    Date of Patent: May 29, 1979
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, Robert W. Shinn, George Suld
  • Patent number: 4156090
    Abstract: 15,15'-Didehydro-astaxanthin and ester derivatives thereof useful as coloring agents and intermediates for astaxanthin and a method for preparing astaxanthin from keto .alpha.-isophorone and intermediates therein.
    Type: Grant
    Filed: November 12, 1976
    Date of Patent: May 22, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Frank Kienzle
  • Patent number: 4138580
    Abstract: A process for preparing a diester of a dicarboxylic acid having two more carbon atoms than the unsaturated hydrocarbon used as a starting material, which comprises subjecting an unsaturated hydrocarbon, carbon monoxide and an alcohol to reaction in the presence of a platinum group metal in combination with one or more compounds selected from the group consisting of nitric acid, a nitrogen oxide and an ester of nitrous acid.
    Type: Grant
    Filed: September 29, 1977
    Date of Patent: February 6, 1979
    Assignee: Ube Industries, Ltd.
    Inventors: Sumio Umemura, Kanenobu Matsui, Yoshinari Ikeda, Katsuro Masunaga
  • Patent number: 4060545
    Abstract: The production of acrylates and methacrylates, made by the oxidative esterification of propylene or isobutylene wherein gaseous reactants are contacted with one or more catalysts and ethylene or an alcohol can be advantageously conducted in a single fluid bed reactor to obtain the desired ester.
    Type: Grant
    Filed: May 28, 1976
    Date of Patent: November 29, 1977
    Assignee: The Standard Oil Company
    Inventors: Arthur F. Miller, Robert J. Zagata, Robert K. Grasselli
  • Patent number: 4056572
    Abstract: A method for the production of phenols which comprises subjecting alkylaromatic hydrocarbons to liquid-phase oxidation with oxygen at a temperature of 100.degree.-300.degree. C and under a pressure of 1-100 atm in the presence of an acidic catalyst taken in an amount of 0.0006-10 mole % and also in the presence of carboxylic acid anhydrides or chlorides, followed by saponifying the resulting phenolic esters.
    Type: Grant
    Filed: February 22, 1974
    Date of Patent: November 1, 1977
    Inventors: Andrei Nikolaevich Bashkirov, Mark Markovich Grozhan, Vladimir Vasilievich Kamzolkin, Jury Anatolievich Lapitsky, Irina Vladimirovna Vygodskaya
  • Patent number: 4051318
    Abstract: Formate esters of the general formula HCOOAr wherein Ar is an aromatic hydrocarbon group containing an alkyl substituent are prepared by oxidizing alkyl aromatic aldehydes of the general formula ArCHO wherein Ar is the same as defined above with organic peroxy acids in the presence of hydrogen fluoride.
    Type: Grant
    Filed: January 5, 1976
    Date of Patent: September 27, 1977
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takashi Suzuki, Susumu Naito