Hetero Ring Containing Reactant Patents (Class 568/483)
  • Patent number: 5210318
    Abstract: A process for producing a 1,3-diol, e.g., 1,3-propanediol, and/or a 3-hydroxyaldehyde, e.g., 3-hydroxypropionaldehyde, is disclosed which comprises contacting a combination of an epoxide, carbon monoxide and hydrogen in the presence of a rhodium-containing catalyst composition effective to promote the hydroformylation of the epoxide at conditions effective to form at least one of a 1,3-diol and a 3-hydroxyaldehyde. The rhodium-containing catalyst composition comprises an anionic rhodium-containing complex. A promoter component is preferably provided to enhance at least one of the rate and selectivity of the epoxide hydroformylation reaction Rhodium-containing compositions and a processes for producing rhodium-containing compositions are also disclosed.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, John M. Maher, Arnold M. Harrison
  • Patent number: 5206442
    Abstract: The preparation of .alpha.,.beta.-unsaturated aldehydes and ketones IO.dbd.C(R.sup.1)--CR.sup.2 .dbd.CR.sup.3 R.sup.4 Iis carried out by acid hydrolysis of cyclic .alpha.,.beta.-unsaturated acetals II ##STR1## in the presence of saturated aldehydes.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: April 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Christiane Mackenroth, Ernst Buschmann
  • Patent number: 5169974
    Abstract: The invention concerns a novel process for the manufacture of various aryloxyaliphatic aldehydes and related arylthio analogues, which are useful as chemical intermediates. The process involves reacting a dihalogenohydroxyalkane of the formula: HO.C(R.sup.2).sub.2.CHX.sub.2 wherein R.sup.2 is alkyl and X is chloro or bromo with a phenol or thiophenol in the presence of base and is applicable to large scale use.
    Type: Grant
    Filed: October 20, 1989
    Date of Patent: December 8, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Gregory D. Harris, Stanley A. Lee
  • Patent number: 5155277
    Abstract: A process for converting tertiary amine N-oxides to aldehydes by reacting tertiary amine N-oxides in the presence of a catalytic quantity of a vanadium containing compound.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: October 13, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Serge Henrot, Claude Mercier
  • Patent number: 4973696
    Abstract: A stereoselective process is described for preparing optically active alpha,beta-disubstituted carbonyl compounds, comprising forming an acetal between an alpha,beta-unsaturated aldehyde or ketone and tartaric acid or a derivative thereof, halogenating the product thus obtained, and restoring the carbonyl compound.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: November 27, 1990
    Assignee: Zambon S.p.A.
    Inventors: Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli, Francesco Minisci
  • Patent number: 4764641
    Abstract: A process is described for preparing optically active alpha-halogenated carbonyl compounds.This process consists of transforming the carbonyl compound into the corresponding acetal with tartaric acid or a derivative thereof, halogenating this acetal and releasing the carbonyl compound.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: August 16, 1988
    Assignee: Zambon SpA
    Inventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano, Carlo Restelli
  • Patent number: 4613694
    Abstract: Process for the concurrent preparation of olefinically unsaturated or satted .alpha.,.omega.-dialdehydes and .alpha.,.omega.-diacids, characterized by the fact that the monoozonide of a a mono- or polyunsaturated cycloolefine in solution in a polar solvent, is treated with water and subsequently with an alkaline aqueous solution at room pressure and at a temperature from -5.degree. C. to 70.degree. C., maintaining during the addition of the alkali, a pH not higher than 12, the dialdehyde and the diacid being subsequently isolated by known, conventional methods.
    Type: Grant
    Filed: September 30, 1980
    Date of Patent: September 23, 1986
    Assignee: Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.p.A.
    Inventors: Pier P. Rossi, Salvatore Marchetti
  • Patent number: 4558154
    Abstract: A novel synthesis of methacrylic acid and methacrolein from isobutylene oxide is provided. This method includes contacting isobutylene oxide with a catalyst, preferably a heteropolyacid catalyst, in the presence of oxygen. Using this method, isobutylene oxide conversion is nearly 100% complete. Depending upon the reaction temperature selected, yields of up to about 60% methacrolein and up to about 12% methacrylic acid may be obtained. A simple, inexpensive high yield process is thus provided for producing reaction mixtures containing methacrylic acid and methacrolein.
    Type: Grant
    Filed: April 27, 1981
    Date of Patent: December 10, 1985
    Assignee: Atlantic Richfield Company
    Inventors: Wilfred P. Shum, John F. White, Eva M. Beals
  • Patent number: 4537998
    Abstract: A novel synthesis of methacrylic acid and methacrolein from isobutylene oxide is provided. This method includes contacting isobutylene oxide with a catalyst, preferably a heteropolyacid catalyst, in the presence of oxygen. Using this method, isobutylene oxide conversion is nearly 100% complete. Depending upon the reaction temperature selected, yields of up to about 60% methacrolein and up to about 12% methacrylic acid may be obtained. A simple, inexpensive high yield process is thus provided for producing reaction mixtures containing methacrylic acid and methacrolein.
    Type: Grant
    Filed: August 13, 1984
    Date of Patent: August 27, 1985
    Assignee: Atlantic Richfield Company
    Inventors: Wilfred P. Shum, John F. White, Eva M. Beals
  • Patent number: 4517386
    Abstract: Terminal epoxides, also known as alpha-epoxides or 1,2-epoxides, are rearranged predominantly to the corresponding aldehydes using a catalyst system consisting of lithium tetrafluoroborate in a polyether solvent.
    Type: Grant
    Filed: May 11, 1984
    Date of Patent: May 14, 1985
    Assignee: Givaudan Corporation
    Inventors: Richard E. Naipawer, Alan J. Chalk
  • Patent number: 4489205
    Abstract: Described herein is a process for the preparation of a novel essentially nonaqueous glutaraldehyde precursor which is capable of rapidly generating glutaraldehyde upon addition to water. The precursor is prepared by the hydration of 2-alkoxy-3, 4-dihydropyran in the presence of an acid catalyst.
    Type: Grant
    Filed: June 28, 1983
    Date of Patent: December 18, 1984
    Assignee: Union Carbide Corporation
    Inventor: Nan S. Chu
  • Patent number: 4469887
    Abstract: To produce methacrylic acid, firstly, isobutyraldehyde is acetalized. The resultant acetal is cleaved into the isobutenyl ether and alcohol. The isobutenyl ether is oxidized with molecular oxygen or an oxygen-containing gaseous mixture in the presence of an alkaline solution at temperatures of 30.degree.-70.degree. C. to obtain the epoxide. This epoxide is hydrolyzed to the .alpha.-hydroxyisobutyraldehyde. The latter is then oxidized with concentrated or fuming nitric acid at temperatures of 20.degree.-110.degree. C. to produce .alpha.-hydroxyisobutyric acid, and methacrylic acid is obtained therefrom by splitting off water.
    Type: Grant
    Filed: October 26, 1982
    Date of Patent: September 4, 1984
    Assignee: Chemische Werke Huels, AG
    Inventors: Rudolf Brockhaus, Hans-Jurgen Franke
  • Patent number: 4448977
    Abstract: A storage stable composition of glutaraldehyde acetals and an organic acidic catalyst, which can be converted to glutaraldehyde at the site and upon demand, by the addition of water.
    Type: Grant
    Filed: August 26, 1982
    Date of Patent: May 15, 1984
    Assignee: Union Carbide Corporation
    Inventors: Glenn H. Warner, Louis F. Theiling, Jr., Marvin G. Freid
  • Patent number: 4426534
    Abstract: 2,2'-bipyridinium chlorochromate has been found to be an effective oxidizing agent, particularly for the conversion of primary or secondary alcohols to their respective aldehydes or ketones.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: January 17, 1984
    Assignee: Thiokol Corporation
    Inventor: Frank S. Guziec, Jr.
  • Patent number: 4399281
    Abstract: 2,2'-Bipyridinium chlorochromate has been found to be an effective oxidizing agent, particularly for the conversion of primary or secondary alcohols to their respective aldehydes or ketones.
    Type: Grant
    Filed: September 22, 1981
    Date of Patent: August 16, 1983
    Assignee: Thiokol Corporation
    Inventor: Frank S. Guziec, Jr.
  • Patent number: 4383122
    Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.
    Type: Grant
    Filed: April 27, 1981
    Date of Patent: May 10, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
  • Patent number: 4337346
    Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 29, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
  • Patent number: 4297517
    Abstract: A process for hydrolysing allylethers of the general formula:R.sub.6 CH.dbd.CR.sub.5 --CR.sub.4 --O--CR.sub.1 R.sub.2 R.sub.3wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6, which may be the same or different, represent a hydrogen atom or an alkyl group of from 1 to 8 carbon atoms or one of R.sub.1, R.sub.2 or R.sub.3 and R.sub.6 together represent a covalent bond, with water in the presence of a supported Group VIII metal catalyst. Methyl sec-butenyl ether can be hydrolysed in high yield to methyl ethyl ketone.
    Type: Grant
    Filed: July 31, 1980
    Date of Patent: October 27, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes A. M. Van Broekhoven, Eit Drent
  • Patent number: 4288635
    Abstract: A method for the preparation of (E)-4-bromo-2-methylbut-2-en-1-al comprises brominating 3,4-epoxy-3-methyl-1-butene with cupric bromide in the presence of lithium carbonate.
    Type: Grant
    Filed: May 23, 1980
    Date of Patent: September 8, 1981
    Assignee: J. T. Baker Chemical Co.
    Inventor: Gary M. Gray
  • Patent number: 4267363
    Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the yellow scale.
    Type: Grant
    Filed: June 26, 1978
    Date of Patent: May 12, 1981
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4240985
    Abstract: Aldehydes are produced by cleaving 2,2-dialkyltetrahydropyrans bearing two hydrogen atoms in the sixth position with a strong acid. The 2,2-dialkyltetrahydropyran can be formed in situ by contacting the strong acid with a primary 6-alken-1-ol having at least one methyl group in the fifth position so that cyclization occurs.
    Type: Grant
    Filed: February 26, 1979
    Date of Patent: December 23, 1980
    Assignee: Ethyl Corporation
    Inventor: Lawrence H. Shepherd, Jr.
  • Patent number: 4205186
    Abstract: A process is described for the preparation of substituted oxyacetaldehydes and acetals thereof according to the reaction sequence: ##STR1## wherein R.sub.1 and R.sub.2 are each lower alkyl or R.sub.1 and R.sub.2, taken together form a lower alkylene group; wherein R.sub.3 is alkyl, alkenyl or alkadienyl and X is halogen selected from the group consisting of chlorine and bromine, the reaction (i) being carried out (1) using a "phase transfer agent" and (2) in a two phase system.
    Type: Grant
    Filed: January 16, 1979
    Date of Patent: May 27, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, John J. Kryschuk, John B. Hall