Carbon To Carbon Unsaturation Containing Patents (Class 568/596)
  • Patent number: 4513143
    Abstract: Rearrangement of allyl acetals to ketene acetals is disclosed. The rearrangement is accomplished by mixing the allyl acetal with a solution of an alkali metal lower alkyl in a water-soluble primary amine. After several hours contact with the allyl acetal with the solution ketene acetal formed during the contact is separated from the reaction mixture.
    Type: Grant
    Filed: December 1, 1982
    Date of Patent: April 23, 1985
    Assignee: SRI International
    Inventors: Steven Y. Ng, Donald W. Penhale, Jorge Heller
  • Patent number: 4513144
    Abstract: Trioxane and other acetals are purified by contacting with an alkali metal superoxide, then isolated in a purified form. Optionally, a phase transfer catalyst can be utilized in the purification. Recovered acetals are sufficiently pure for polymerization to high molecular weight.
    Type: Grant
    Filed: November 3, 1982
    Date of Patent: April 23, 1985
    Assignee: Conoco Inc.
    Inventor: Jeff T. Fenton
  • Patent number: 4504422
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: March 12, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • Patent number: 4504421
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: March 12, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • Patent number: 4503239
    Abstract: Process for the preparation of halogenoacetals of the general formula: ##STR1## wherein X represents chlorine or bromine, the symbols R each represent a linear or branched alkyl radical (1 to 6 carbon atoms) or together form a linear or branched alkylene radical (2 to 6 carbon atoms), and the symbols R.sub.1 and R.sub.2, which are identical or different, represent a hydrogen atom or an alkyl radical (1 to 6 carbon atoms), by reaction of chlorine or bromine with a .beta.,.gamma.-ethylenic aldehyde, in the presence of a tertiary amide, followed by reaction with a primary or secondary aliphatic alcohol, a diol (preferably a glycol) or an alkyl orthoformate.
    Type: Grant
    Filed: December 16, 1982
    Date of Patent: March 5, 1985
    Assignee: Rhone-Poulenc Sante
    Inventor: Jean Desmurs
  • Patent number: 4501705
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: February 26, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • 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: 4317905
    Abstract: A process is disclosed for preparing aliphatic compounds containing two conjugated double bonds cis-cis or cis-trans, characterized in that a compound of the general formula ##STR1## (in which R is H, alkyl from C.sub.1 to C.sub.10, or OY in which Y is a protective group selected from the class consisting of tetrahydropyranyl and 1-ethoxyethyl; X is an ester function selected from the class consisting of the acetates) is reacted with an alkyl-magnesium halide of the general formula:Z--Mg--R.sup.1 (II)(in which Z is chlorine, bromine or iodine, and R.sup.1 is a C.sub.1 -C.sub.10 alkyl group, or a group (CH.sub.2).sub.n OY in which Y has the same meaning as in formula (I), and n is a number from 3 to 10) in the presence of Li.sub.2 CuCl.sub.4, CuCl, CuBr, or CuI at temperatures ranging from about -30.degree. to +10.degree. C. in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula:R--CH.sub.2 --C.tbd.C--CH.dbd.CH--CH.sub.2 R.sup.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: March 2, 1982
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi
  • Patent number: 4277610
    Abstract: A synthesis of 2,6,10-trimethyl-undecan-1-ol, an intermediate for producing vitamin E, from methacrolein, crotonaldehyde, .beta.-hydroxy-isobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: July 7, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy
  • Patent number: 4209644
    Abstract: An unsaturated carbonyl compound, for example, one expressed by the following formula, ##STR1## is prepared by maintaining at an elevated temperature a novel allyl acetal of a .beta.,.gamma.-unsaturated aldehyde, for example, one expressed by the following formula ##STR2## The allyl acetal can be derived, for example, for 3-methyl-3-butenal-1 having 5 carbon atoms and prenyl alcohol having 5 carbon atoms. Thus, the unsaturated aldehyde having the increased number of carbon atoms can be formed in a high yield by a relatively simple reaction.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: June 24, 1980
    Assignee: Teijin Limited
    Inventors: Yataro Ichikawa, Teizo Yamaji, Mamoru Yamamoto
  • Patent number: 4191842
    Abstract: A synthesis of vitamin E in racemic or optically active forms from methacryolein or beta-hydroxyisobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: January 17, 1979
    Date of Patent: March 4, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy
  • Patent number: 4179579
    Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: December 18, 1979
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara
  • Patent number: 4175187
    Abstract: Tertiary allylic amines are obtained from vinylic halides and olefins, and substituted derivatives thereof, by reacting said halide with a mono-, di-, or tri-substituted olefin and an unhindered basic secondary amine in the presence of a palladium catalyst.
    Type: Grant
    Filed: October 24, 1978
    Date of Patent: November 20, 1979
    Assignee: University of Delaware
    Inventor: Richard F. Heck
  • Patent number: 4139720
    Abstract: A multi-step process for the preparation of alpha,beta-unsaturated aliphatic aldehydes such as citral by first reacting an allylic alcohol with a butadienyl ether, or a corresponding acrolein derivative or its acetal, including novel intermediates in this process.
    Type: Grant
    Filed: November 16, 1977
    Date of Patent: February 13, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Willy Leimgruber, Donald H. Valentine, Jr.
  • Patent number: 4133836
    Abstract: A process for the manufacture of acetals by reacting aliphatic aldehydes with aliphatic alcohols, especially olefinically unsaturated aldehydes and allyl alcohols, in the presence of a distillable acid, especially nitric acid, using a rectifying column as the reaction vessel. The products may be used as starting materials for plastics, active substances, scents and vitamins.
    Type: Grant
    Filed: May 31, 1977
    Date of Patent: January 9, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Axel Nissen, Gerd Kaibel
  • Patent number: 4130529
    Abstract: An aqueous film-forming composition is prepared by radially polymerizing unsaturated vinyl monomer with an emulsion stabilizer of oxidation curing water-soluble resin and impregnating the obtained emulsion with a compound represented by the general formula: ##STR1##
    Type: Grant
    Filed: June 30, 1977
    Date of Patent: December 19, 1978
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Yasuharu Nakayama, Tadashi Watanabe, Reiziro Nishida, Satoru Enomoto
  • Patent number: 4130526
    Abstract: An aqueous coating composition which is prepared by radially polymerizing unsaturated vinyl monomer with ionic or nonionic surface active agent, and impregnating the obtained emulsion with a compound (A) that is represented by the general formula: ##STR1##
    Type: Grant
    Filed: June 30, 1977
    Date of Patent: December 19, 1978
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Yasuharu Nakayama, Tadashi Watanabe, Reiziro Nishida, Satoru Enomoto