Patents Represented by Attorney Richard H. Thomas
  • Patent number: 4035425
    Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.
    Type: Grant
    Filed: April 10, 1975
    Date of Patent: July 12, 1977
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: 4020108
    Abstract: In a process for the catalytic hydrogenation of unsaturated compounds, which process is characterizable as employing for the active catalyst a glyoxime complexed with cobalt and a base, referred to as a cobaloxime catalyst, the improvement for obtaining increased conversion and/or yield comprising employing a large excess of the glyoxime complexing agent in the hydrogenation reaction. The invention is particularly applicable to the selective reduction of certain .alpha.,.beta.-unsaturated aliphatic ketones and is described with reference to the highly selective hydrogenation of carvone to dihydrocarvone.
    Type: Grant
    Filed: June 30, 1976
    Date of Patent: April 26, 1977
    Assignee: SCM Corporation
    Inventor: William J. Ehmann
  • Patent number: 4018842
    Abstract: Disclosed is a process for the stereoselective hydrogenation of .alpha.-pinene to cis-pinane in which the formation of trans-pinane is suppressed. The hydrogenation is carried out in the presence of a hydrogenation catalyst, under hydrogenation conditions, wherein to obtain increased stereoselectivity, an effective amount of the reactive surfaces of the hydrogenation catalyst is inactivated with a catalyst modifier.
    Type: Grant
    Filed: May 27, 1976
    Date of Patent: April 19, 1977
    Assignee: SCM Corporation
    Inventor: Levy A. Canova
  • Patent number: 4001307
    Abstract: A process for the preparation of 4-halo-3-methylbut-2-enyl lower fatty acid esters from isoprene comprising the steps of halogenating isoprene in the presence of a dipolar aprotic solvent to produce a reaction mixture of which a predominant portion is 1,4-dihalo-2-methyl-2-butene, and esterifying said dihalo-butene under esterification reaction conditions with an alkali metal salt of a lower fatty acid. The amount of alkali metal salt is sufficient stoichiometrically to replace the halogen ion in the 1-position with the anion of said alkali metal salt, a substantial portion of the product of the esterification reaction being desired 4-halo-3-methylbut-2-enyl lower fatty acid ester.
    Type: Grant
    Filed: May 10, 1973
    Date of Patent: January 4, 1977
    Assignee: SCM Corporation
    Inventor: Carlos G. Cardenas
  • Patent number: 3966574
    Abstract: The present invention resides in the discovery that ethylenically unsaturated organic compounds can be readily photopolymerized by adding to such compounds a catalytic formulation including certain FDA approved food color additives and an amount of an organic amine activator. Particularly improved results are obtained by employing as said food color additive the combination of FD&C red No. 3 dye, with either FD&C red No. 2 dye, FD&C red No. 40 dye, or with both FD&C red No. 2 and FD&C red No. 40 dyes.
    Type: Grant
    Filed: June 30, 1975
    Date of Patent: June 29, 1976
    Assignee: SCM Corporation
    Inventors: John David LaBash, Vincent D. McGinniss
  • Patent number: 3966993
    Abstract: A process for making a solid sauce bar by mixing fat flour and condiments, tempering the mixture, and subsequently casting and cooling the bar until it is stable at room temperature.
    Type: Grant
    Filed: May 20, 1970
    Date of Patent: June 29, 1976
    Assignee: SCM Corporation
    Inventor: John V. Luck
  • Patent number: 3949006
    Abstract: A synthesis of novel Vitamin A intermediates from betaionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.
    Type: Grant
    Filed: April 23, 1973
    Date of Patent: April 6, 1976
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: 3947498
    Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.
    Type: Grant
    Filed: April 10, 1975
    Date of Patent: March 30, 1976
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: 3938934
    Abstract: Combustion air feed to a fuel burner is warmed with water otherwise destined for evaporative cooling in a cooling tower or spray pond; then the resulting warmed air is sent to combustion while the resulting cooled water is further cooled by evaporation for recycle use.
    Type: Grant
    Filed: November 8, 1974
    Date of Patent: February 17, 1976
    Assignee: SCM Corporation
    Inventor: William A. Frondorf
  • Patent number: 3932539
    Abstract: An improved process for the preparation of unsaturated terpene alcohols such as myrcenol and cis and trans ocimenol is described. Acyclic terpene allylic halides are reacted with a tertiary amine of the formula hereinafter described to form the corresponding quaternary ammonium salt which is then acidified to remove the ethylenic unsaturation between the 6th and 7th carbon atom and adding a hydroxy substituent on the 7th carbon atom of the terpene halide salt. The hydrated terpene ammonium halide salt is made neutral and thermally decomposed into the unsaturated terpene alcohols. Myrcenol and ocimenol cis and trans are useful for their fragrance and aroma in perfumery and cosmetic manufacture.
    Type: Grant
    Filed: February 14, 1972
    Date of Patent: January 13, 1976
    Assignee: SCM Corporation
    Inventors: Bernard J. Kane, Richard A. Von Genk
  • Patent number: 3932543
    Abstract: In the process for halogenation of conjugated dienes with elemental halogen under halogenation conditions, the improvement for obtaining increased yield of dihalogenated butene products comprising forming the reaction mixture with a dipolar aprotic solvent vehicle resistant to halogenation under such conditions in the proportion of about 0.05-10 moles per mole of said diene. The invention has particular application in the chlorination of isoprene to 1,4-dichloro-2-methyl-2-butene and 1,2-dichloro-2-methyl-3-butene.
    Type: Grant
    Filed: April 13, 1973
    Date of Patent: January 13, 1976
    Assignee: SCM Corporation
    Inventors: Richard A. Von Genk, Carlos G. Cardenas