Organic Hydroperoxide Reactant Patents (Class 549/529)
  • Patent number: 4703027
    Abstract: Complexes are made by reacting a solid ammonium molybdate and a solid alkali metal molybdate with ethylene glycol. Stripping of water of reaction subsequent to complex formation is preferred. The ratio of moles of alkylene glycol to total gram atoms of molybdenum should be in the range from about 7:1 to about 20:1 and the ratio of gram atoms of molybdenum in the ammonium molybdate to gram atoms of molybenum in the alkali metal molybdenum should be in the range of about 1:1 to about 20:1. Solutions of the complexes are excellent catalysts for the reaction of propylene with an organic hydroperoxide such as tertiary butyl hydroperoxide to form proplyene oxide and tertiary butyl alcohol.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: October 27, 1987
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, John R. Sanderson, Kenneth P. Keating
  • Patent number: 4661463
    Abstract: The process of regenerating a soluble, stable molybdenum-containing catalyst suitable for epoxidation of olefins with a hydroperoxide which comprises thermally precipitating and separating a molybdenum-containing solid obtained from a spent catalyst stream derived from a molybdenum catalyzed epoxidation of an olefin and solubilizing the precipitated solid by contacting with a liquid composition comprising an admixture of a monohydroxy alcohol, a polyhydroxy alcohol and an organic peroxide or hydroperoxide, said polyhydroxy alcohol being present in an amount of at least about 2 moles per mole or molybdenum to be solubilized.
    Type: Grant
    Filed: September 12, 1984
    Date of Patent: April 28, 1987
    Assignee: Atlantic Richfield Company
    Inventor: Michael T. Mocella
  • Patent number: 4654427
    Abstract: Storage stable solutions of molybdenum/alkanol complexes in the alkanol are prepared by reacting a molybdenum oxide and ammonium hydroxide and an amount of a straight chain or branched chain C.sub.6 -C.sub.13 alkanol, within the range of about 10 to about 55 moles of alkanol per gram atom of molybdenum sufficient to form a storage stable molybdenum/alkanol complex. The complex-forming reaction is initiated in the presence of about 1 to about 4 moles of water per gram atom of molybdenum and about 0.5 to about 10 moles of ammonia per gram atom of molybdenum, the water and ammonia preferably being added in the form of concentrated ammonium hydroxide. The reaction is conducted at a temperature of about 120.degree. to about 190.degree. C. for a period of time, normally about 3 to about 8 hours, sufficient to substantially completely remove ammonia and water to provide a liquid reaction product comprising said solution of molybdenum/alkanol complex dissolved in unreacted alkanol and containing about 0.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: March 31, 1987
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, John R. Sanderson, Kenneth P. Keating, William A. Smith
  • Patent number: 4650886
    Abstract: Storage stable solutions of molybdenum/alkanol complexes in the alkanol are prepared by reacting an ammonium molybdate with an amount of a straight chain or branched chain C.sub.6 -C.sub.13 alkanol, within the range of about 7 to about 20 moles of alkanol per gram atom of molybdenum sufficient to form a storage stable molybdenum/alkanol complex. The complex-forming reaction is initiated in the presence of about 1 to about 4 moles of added water per gram atom of molybdenum and is conducted at a temperature of about 120.degree. to about 190.degree. C. for a period of time, normally about 3 to about 8 hours, sufficient to substantially completely remove ammonia and water to provide a liquid reaction product comprising said solution of molybdenum/alkanol complex dissolved in unreacted alkanol and containing about 0.001 to about 0.1 wt. % of water. The reaction product is filtered to provide a clarified storage stable solution of the molybdenum/alkanol complex.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: March 17, 1987
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, John R. Sanderson, Kenneth P. Keating, William A. Smith
  • Patent number: 4607113
    Abstract: Production of novel molybdenum dioxo dialkyleneglycolate compositions, especially adapted for use as catalysts in the epoxidation of olefinic compounds with an organic hydroperoxide, by reaction of molybdenum trioxide with particular dialkylene glycol compounds at specified elevated temperatures while removing water.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: August 19, 1986
    Assignee: Atlantic Richfield Company
    Inventors: Wilfred P. Shum, Charles F. Cooper
  • Patent number: 4602100
    Abstract: A family of polymer bound organometallic complexes comprises compounds derived from a metal and a functionalized organic polymer of formula ##STR1## wherein X is a polymer backbone bonded to a ligand in which; Y is a group derived from an atom selected from C, Si, N and P; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are, independently, groups selected from H, a C.sub.1 -C.sub.4 alkyl group and a halogen atom; R.sub.5 and R.sub.6 are, independently, groups selected from H, a C.sub.1 -C.sub.4 alkyl group and a halogen atom, or together with the nitrogen atom form a heterocyclic ring having 5 or 6 atoms; R.sub.7 and R.sub.8 are, independently, groups selected from H, a C.sub.1 -C.sub.4 alkyl group, an aryl group and a halogen atom and each of n and m have a value from 0 to 10. When the metal is either molybdenum or vanadium the complexes are suitable catalysts for the epoxidation of olefins.
    Type: Grant
    Filed: October 16, 1984
    Date of Patent: July 22, 1986
    Assignee: BP Chemicals Limited
    Inventor: Raymond L. Kelly
  • Patent number: 4598057
    Abstract: The process of regenerating a stable organic soluble molybdenum-containing catalyst suitable for epoxidation of olefins with a hydroperoxide which comprises thermally precipitating and separating a molybdenum-containing solid obtained from a spent catalyst stream derived from a molybdenum catalyzed epoxidation of an olefin and solubilizing the precipitated solid by contacting with a liquid composition comprising a peroxy compound, a monohydroxy alcohol, optionally a polyhydroxy alcohol, and an organic dicarboxylic acid present in an amount of at least about 0.2 parts, by weight, of molybdenum contained in said solid.
    Type: Grant
    Filed: October 26, 1984
    Date of Patent: July 1, 1986
    Assignee: Atlantic Richfield Company
    Inventor: Bruce H. Isaacs
  • Patent number: 4593012
    Abstract: Production of novel hydrocarbon-soluble salts, especially adapted for use as catalysts in the epoxidation of olefinic compounds with an organic hydroperoxide, by reaction of an ammonium molybdate with a carboxylic acid in the presence of an organic amine at specified elevated temperatures while removing water.
    Type: Grant
    Filed: March 5, 1985
    Date of Patent: June 3, 1986
    Assignee: Atlantic Richfield Company
    Inventors: Masahiro Usui, Yasuhiko Higashio
  • Patent number: 4590172
    Abstract: Production of molybdenum-containing stable catalyst solutions especially adapted for use in the epoxidation of olefinic compounds with an organic hydroperoxide by reaction of molybdenum metal with a peroxy compound and an organic dicarboxylic acid in the presence of monohydroxy alcohol is provided.
    Type: Grant
    Filed: October 26, 1984
    Date of Patent: May 20, 1986
    Assignee: Atlantic Richfield Company
    Inventor: Bruce H. Isaacs
  • Patent number: 4579967
    Abstract: This invention provides a process for converting alkyl isobutyrate to alkyl methacrylate via alkyl-hydroperoxy-isobutyrate and alkyl alpha-hydroxyisobutyrate intermediate.An important aspect of the process is the use of a particulate metal oxide substrate in the first step of the process.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: April 1, 1986
    Assignee: Celanese Corporation
    Inventor: H. Clay Linstid, III
  • Patent number: 4567283
    Abstract: Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2;Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2 or 3;the sum of m+n+p is an integer of 2 to 5, inclusive;R.sub.2 and R.sub.3 each is H or alkyl, and the like;R.sub.1 is H or alkyl; andW is an unsaturated moiety, are useful as plant growth regulators and herbicides.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: January 28, 1986
    Assignee: Shell Oil Company
    Inventors: George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
  • Patent number: 4483997
    Abstract: A method for the preparation of an epoxide by reacting an olefin having 3 or more carbon atoms with a hydroperoxide in the presence of a catalyst. The catalyst includes molybdenum and/or tungsten and an inorganic metal phosphate and/or arsenate wherein at least the inorganic metal phosphate and/or arsenate is substantially insoluble in the olefin hydroperoxide reaction mixture. The metal portion of the inorganic metal phosphate and/or arsenate is one or more metals selected from the group consisting of the metals found in Groups I to III, VIIb and VIII, of the Periodic Table of Elements. Preferred metals include aluminum, iron, zinc and mixtures of these metals.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: November 20, 1984
    Assignee: Texaco Inc.
    Inventors: Edward E. McEntire, Robert M. Gipson
  • Patent number: 4433159
    Abstract: Optically active alpha-tocopherol is synthesized by a multi-step process using phytol as a starting material. The process does not require an optical resolution step.
    Type: Grant
    Filed: February 18, 1982
    Date of Patent: February 21, 1984
    Assignee: Eisai Co., Ltd.
    Inventors: Kimio Hamamura, Kozo Akasaka, Youji Yamagishi
  • Patent number: 4402794
    Abstract: A process for purifying 1,2-butylene oxide which comprises extractive distillation of crude butylene oxide with an added solvent comprising an acyclic, paraffinic hydrocarbon having from 7 to 9 carbon atoms.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: September 6, 1983
    Assignee: Atlantic Richfield Company
    Inventors: Margaret I. Nemet-Mavrodin, Yon-Li Shangkuan, Richard L. Bobeck
  • Patent number: 4367342
    Abstract: Alkene oxides are produced by the reaction of an organic hydroperoxide and an alkene in the presence of a catalyst of an inorganic oxygen compound of silicon in chemical combination with an oxide or hydroxide of titanium.
    Type: Grant
    Filed: May 26, 1978
    Date of Patent: January 4, 1983
    Assignee: Shell Oil Company
    Inventors: Harald P. Wulff, Freddy Wattimena