Of Aldehyde Patents (Class 562/531)
  • Patent number: 4414182
    Abstract: Hydrogen is generated by contacting an alkaline aqueous solution of formaldehyde with at least one catalyst selected from the group consisting of molybdenum, tungsten, molybdenum carbides, tungsten carbides, molybdenum nitrides, tungstenum borides, copper, silver, gold and compounds of copper, silver and gold.Hydrogen can be generated at ambient temperature under atmospheric pressure and, therefore, complicated steps or complicated devices are unnecessary.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: November 8, 1983
    Assignee: Hitachi, Ltd.
    Inventors: Hiroshi Okamoto, Tetsuichi Kudo, Go Kawamura
  • Patent number: 4394355
    Abstract: The solid oxalate of a catalytic metal such as cobalt, typically formed as an undesired and useless by-product during the liquid-phase oxidation of an organic compound, typically a hydrocarbon, in the presence of a homogeneous catalyst comprising said metal, is treated to convert the metal moiety to a reusable form by a process comprising leaching the metal oxalate with an aqueous solution of a soluble salt of ethylenediaminetetraacetic acid (EDTA). The resulting solution of EDTA-metal complex or chelate is then mixed with a soluble calcium salt to precipitate the oxalate moiety as insoluble calcium oxalate leaving the metal-EDTA complex in solution. After removing the resulting solid calcium oxalate, the remaining filtrate is acidified to convert the metal moiety to a simple salt which can be recycled to the liquid-phase oxidation, while the EDTA is precipitated as a solid which can also be recovered and re-used in the complexation step of the process.
    Type: Grant
    Filed: March 2, 1982
    Date of Patent: July 19, 1983
    Assignee: Celanese Corporation
    Inventor: James D. Fruge'
  • Patent number: 4353832
    Abstract: A process for the production of carboxyl compounds such as caprolactones, in which the corresponding carbonyl compounds are oxidized with hydrogen peroxide in the presence of a catalyst in a substantially anhydrous liquid medium. The water formed by the reaction and any water introduced into the reaction mixture are removed from the reaction mixture.
    Type: Grant
    Filed: June 5, 1980
    Date of Patent: October 12, 1982
    Assignee: INTEROX (Societe Anonyme)
    Inventors: Andre Lecloux, Claude Declerck, Franz Legrand
  • Patent number: 4350829
    Abstract: There is disclosed a process for the production of isobutyric acid by liquid-phase oxidation of isobutyraldehyde in the presence of an alkali metal-containing compound, the oxidation being effected while maintaining the molar ratio of oxygen to isobutyraldehyde to be fed at 0.5 or above.
    Type: Grant
    Filed: June 27, 1979
    Date of Patent: September 21, 1982
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Tatsuo Masuko, Shigeo Fukaya, Nobuyuki Murai, Jun Noma
  • Patent number: 4343950
    Abstract: A one-step process is disclosed for forming a carboxylic acid and its anhydride directly from the corresponding olefin which comprises reacting the olefin with carbon monoxide, hydrogen and oxygen in the presence of a stable rhodium complex catalyst. The rhodium catalyst is stabilized by a pentavalent Group V ligand, such as a phosphine oxide. The reaction is preferably conducted in an inert organic solvent. In an alternate embodiment, a carboxylic acid may be obtained by oxidation of an aldehyde (produced, for example, by hydroformylation of the corresponding olefin) in the presence of a rhodium complex catalyst stabilized by a pentavalent Group V ligand. This reaction is also preferably conducted in an inert organic solvent.
    Type: Grant
    Filed: January 16, 1981
    Date of Patent: August 10, 1982
    Assignee: Union Carbide Corporation
    Inventors: Rocco A. Fiato, Roy L. Pruett
  • Patent number: 4338462
    Abstract: In the process for oxidizing methacrolein to a methacrylic acid salt with an oxidizing gas in a strongly alkaline medium at a temperature of 0 to 100.degree. C. and in the presence of a finely divided silver catalyst and recovering methacrylic acid by acidification, the improvement which comprises carrying out said oxidation in the presence of a small amount of dissolved alkali metal carbonate.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: July 6, 1982
    Assignee: Atlantic Richfield Company
    Inventor: Gregory A. Wheaton
  • Patent number: 4317925
    Abstract: A process for the preparation of di-n-propylacetic acid which comprises the steps ofA. converting n-valeraldehyde-diallyl acetal into allyl-1-pentenyl ether by cleaving one mol of allyl alcohol per one mol of n-valeraldehye-diallyl acetal;B. rearranging the allyl-1-pentenyl ether thermally into 2-propyl-pent-4-en-1-al,C. partially hydrogenating the 2-propyl-pent-en-1-al catalytically to form 2-propyl valeraldehyde, andD. oxidizing the 2-propyl valeraldehyde to form dipropyl-acetic acid.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: March 2, 1982
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
  • Patent number: 4311854
    Abstract: A process for the preparation of di-n-propyl-acetic acid, comprising the steps of:A. catalytically reacting n-butyric acid with cleavage of carbon dioxide and water to form heptanone-4;B. hydrogenating heptanone-4 in teh presence of a catalyst to form heptanol-4;C. dehydrating heptanol-4 in the presence of an Al.sub.2 O.sub.3 catalyst to form heptene-3;D. hydroformylating heptene-3 in the presence of a rhodium complex compound as catalyst to form a mixture of 2-propyl pentanal and 2-ethyl hexanal;E. oxidizing the 2-propyl pentanal/2-ethyl hexanal mixture to form a mixture of di-n-propyl acetic acid and 2-ethyl hexanoic acid, andF. separating the mixture of di-n-propyl acetic acid and 2-ethyl hexanoic acid to recover pure di-n-propyl acetic acid.If desired, step B can be carried out without purification of the product of step A. Moreover, the dehydration of step C can be carried out without previous purification of the product of step B.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: January 19, 1982
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Volker Falk, Claus Kniep
  • Patent number: 4302394
    Abstract: Butyrolactone is produced by oxidizing an aldehyde-ether of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each, independently of the other, represent a C.sub.1 to C.sub.4 alkyl radical, and R.sub.3 and R.sub.4 each, independently of the other, represent a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, or wherein R.sub.1 represents a C.sub.1 to C.sub.4 alkyl radical, R.sub.2 and R.sub.3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R.sub.4 represents a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, to form an acid ether of the general formula: ##STR2## followed by deetherification, dehydration and cyclization. Oxidation can be carried out with e.g. gaseous oxygen. Deetherification can be accomplished by contact with an acid catalyst, while cyclization may occur spontaneously. A cyclic process is described in which allyl alcohol is converted by reaction with a suitable olefin, e.g.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: November 24, 1981
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventor: Alan J. Dennis
  • Patent number: 4289708
    Abstract: A process is described for separating soluble copper and manganese catalysts from organic saturated monocarboxylic acids having 3 to 9 carbon atoms by precipitating the copper and manganese as oxalates.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: September 15, 1981
    Assignee: Celanese Corporation
    Inventors: Robert H. Scott, Hubert H. Thigpen, Frank Wood, Jr.
  • Patent number: 4285875
    Abstract: A process for preparing carboxylic acids by the oxidative conversion of the corresponding aldehydes comprises oxidizing the aldehydes in the presence of a catalyst comprising the anion [Fe(CN).sub.5 H.sub.2 O].sup.-3. The catalyst may be selected from [Fe(CN).sub.5 H.sub.2 O].sup.-3, compounds that form [Fe(CN).sub.5 H.sub.2 O].sup.-3 under the reaction conditions, and their salts. The catalyst is useful for the oxidation of aldehydes with oxygen or oxygen-containing gases. The present process permits the use of lower reaction times and temperatures, and reduces the formation of undesirable reaction by-products.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: August 25, 1981
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Boy Cornils, Werner De Win, Jurgen Weber
  • Patent number: 4273936
    Abstract: A one-step process is disclosed for forming a carboxylic acid and its anhydride directly from the corresponding olefin which comprises reacting the olefin with carbon monoxide, hydrogen and oxygen in the presence of a stable rhodium complex catalyst. The rhodium catalyst is stabilized by a pentavalent Group V ligand, such as a phosphine oxide. The reaction is preferably conducted in an inert organic solvent. In an alternate embodiment, a carboxylic acid may be obtained by oxidation of an aldehyde (produced, for example, by hydroformylation of the corresponding olefin) in the presence of a rhodium complex catalyst stabilized by a pentavalent Group V ligand. This reaction is also preferably conducted in an inert organic solvent.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: June 16, 1981
    Assignee: Union Carbide Corporation
    Inventors: Rocco A. Fiato, Roy L. Pruett
  • Patent number: 4263448
    Abstract: An oxidizable hydrocarbon is oxidized in a reaction zone at elevated temperature in the presence of a liquid reaction medium by introducing the hydrocarbon and a feed stream containing molecular oxygen to the reaction zone under conditions sufficient to oxidize at least a portion of the hydrocarbon; withdrawing at least a portion of the liquid reaction medium from the reaction zone; passing at least a portion of the withdrawn liquid reaction medium to an oxygen injection zone located external to the reaction zone; contacting the liquid in said oxygen-injection zone with a gas stream containing molecular oxygen under conditions sufficient to form a two-phase gas/liquid mixture; and passing said two-phase gas/liquid mixture to the reaction zone as the feed of molecular oxygen thereto.
    Type: Grant
    Filed: March 30, 1979
    Date of Patent: April 21, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: James Leacock
  • Patent number: 4246185
    Abstract: A process is described for separating soluble copper and manganese catalysts from organic saturated aliphatic monocarboxylic acids having 6 to 9 carbon atoms by precipitating the copper and manganese as oxalates into a separate aqueous phase.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: January 20, 1981
    Assignee: Celanese Corporation
    Inventor: Frank Wood, Jr.
  • 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: 4182919
    Abstract: A reaction in a catalyst suspension system is carried out by using a reactor equipped with a filter for separating the catalyst in the reactor.
    Type: Grant
    Filed: March 16, 1978
    Date of Patent: January 8, 1980
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Shunsuke Mabuchi, Sadakatsu Kumoi, Kenji Tsuzuki
  • Patent number: 4146731
    Abstract: Improved process for preparing glyoxylic acid by oxidizing glyoxal with nitric acid at a concentration of 4 to 10% by weight of nitric acid based on the weight of the reaction system, introducing oxygen or oxygen-containing gas into the reaction system so as to satisfy a relation K.sub.L a.P.gtoreq.150, wherein K.sub.L a is a liquid-phase over-all mass transfer coefficient of the reactor (1/hour) and P is a partial pressure of oxygen in the reaction system (kg./cm..sup.2). Glyoxylic acid can be prepared in high yields with less consumption of nitric acid and the generation of nitrogen oxides can be remarkably decreased.
    Type: Grant
    Filed: March 10, 1977
    Date of Patent: March 27, 1979
    Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha
    Inventors: Junzo Ogahara, Kunihiko Sekiyama
  • Patent number: 4125559
    Abstract: Alkali metal salts of arabonic acid are manufactured by oxidizing D-hexoses in the presence of alkali metal compounds under specific conditions in respect of temperature, pressure, reaction time, sequence of addition of the individual reactants and mixing.The alkali metal salts of arabonic acid which may be manufactured by the process of the invention are valuable starting materials for the manufacture of vitamins, electro-coating assistants, crop protection agents and metal complexing agents.
    Type: Grant
    Filed: May 19, 1977
    Date of Patent: November 14, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Scholz, Guenther Gotsmann