Isomerization Patents (Class 558/88)
  • Patent number: 6147062
    Abstract: This invention relates to a new class of phosphoryl hydrazine compounds which are useful as insecticides, acaricides, anthelmintics, and nematocides, compositions containing the compounds, and methods for their use. This invention also relates to methods to produce such compounds.
    Type: Grant
    Filed: November 15, 1999
    Date of Patent: November 14, 2000
    Assignee: Rohm and Haas Company
    Inventors: Richard Martin Jacobson, Luong Tu Nguyen
  • Patent number: 6075157
    Abstract: The present invention provides a method for making O,S-dimethyl phosphoramidothioate. In accordance with this process, O,O-dimethyl phosphoramidothioate is isomerized in the presence of dimethyl sulfate to form a reaction mixture; the reaction mixture is then passed through a wiped film evaporator at a temperature of from about 55.degree. C. to about 120.degree. C. and a pressure of from about 3 to about 10 mm Hg, with the distillate containing O,S-dimethyl phosphoramidothioate, unreacted O,O-dimethyl phosphoramidothioate and by-products, and the residue containing O,S-dimethyl phosphoramidothioate in an amount greater than the amount of O,S-dimethyl phosphoramidothioate contained in the reaction mixture prior to distillation.
    Type: Grant
    Filed: August 17, 1998
    Date of Patent: June 13, 2000
    Assignee: Bayer Corporation
    Inventors: Vidyanatha A. Prasad, Klaus Jelich
  • Patent number: 5936113
    Abstract: The present invention provides a method for making O,S-dimethyl phosphoramidothioate. In accordance with that process, a mixture containing O,S-dimethyl phosphoramidothioate is lagered at a temperature of from 35.degree. C. to about 45.degree. C. for from about 3 to about 6 hours.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: August 10, 1999
    Assignee: Bayer Corporation
    Inventors: Vidyantha A. Prasad, Klaus Jelich, Donald K. Smith
  • Patent number: 5922896
    Abstract: The present invention provides a method for making O,S-dimethyl phosphoramidothioate. In accordance with the present process, O,O-dimethyl phosphoramidothioate is isomerized in the presence of a catalyst at a temperature of from about 35.degree. C. to about 45.degree. C. to form a mixture containing O,S-dimethyl phosphoramidothioate and the resultant mixture is lagered at a temperature of from about 35.degree. C. to about 45.degree. C. for about 3 to 6 hours. The total time for both steps is at least about 4 hours.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: July 13, 1999
    Assignee: Bayer Corporation
    Inventors: Vidyanatha A. Prasad, Klaus Jelich, Donald K. Smith
  • Patent number: 5489635
    Abstract: The new crystalline modification of 1,1',1"-nitrilo{tri-2-propyl-tris[2,2'-ethylidene-bis(4,6-di-tert-butylphe nyl)]phosphite} is obtained by crystallizing said compound from the melt at elevated temperatures.This crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: February 6, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Sai P. Shum, Stephen D. Pastor
  • Patent number: 5489636
    Abstract: The new amorphous modification of 1,1',1"-nitrilo{tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylph enyl)]phosphite } is obtained by cooling rapidly said compound from the melt to ambient temperature.This amorphous form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: February 6, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Sai P. Shum, Stephen D. Pastor
  • Patent number: 5473093
    Abstract: Diethyl ethylphosphonate is formed by the catalytic rearrangement of triethyl phosphite in a reaction medium at elevated temperature, preferably using an ethyl iodide as the rearrangement catalyst, employing a heel of diethyl ethylphosphonate in the reaction medium when the reaction is begun with maintaining of the reaction medium at a temperature above the boiling point of the triethyl phosphite (for example, a temperature of from about 175.degree. C. to about 185.degree. C.) and addition of the triethyl phosphite to the reaction medium at a rate slow enough to maintain that temperature.
    Type: Grant
    Filed: January 10, 1995
    Date of Patent: December 5, 1995
    Assignee: Akzo Nobel N.V.
    Inventor: Fred Jaffe
  • Patent number: 5424478
    Abstract: The present specification relates to an industrially advantageous process for producing vitamin A derivatives which are useful as medicaments, feed additives, food additives and the like. The process provides vitamin A derivatives, particularly all-trans vitamin A derivatives in high yield and purity.
    Type: Grant
    Filed: March 22, 1994
    Date of Patent: June 13, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsutaka Tanaka, Tadashi Hanaoka, Kunio Takanohashi
  • Patent number: 5142084
    Abstract: A novel process for rearranging triallyl phosphite to diallyl allylphosphonate ester is disclosed. The process involves heating triallyl phosphite in the presence of a soluble, inorganic bromide or iodide catalyst. The rearrangement process is useful in a 3-step process for the preparation allylphosphonic acid from trialkyl phosphite without the isolation of intermediates.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: August 25, 1992
    Inventors: Charles G. Carter, David R. Sterrenburg
  • Patent number: 5138084
    Abstract: A process for the preparation of 4-O-phosphates of dopamine and dopamine derivatives by treatment of a mixture of both 3-O-phosphate and 4-O-phosphate isomers with a strong mineral acid and optional esterification of the so obtained phosphoric ester of dopamine or dopamine derivatives is described.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: August 11, 1992
    Assignee: SIMES Societa Italiana Medicinali e Sintetici S.p.A.
    Inventors: Cesare Casagrande, Francesco Santangelo
  • Patent number: 5072032
    Abstract: Methods for converting phosphonates into thiophosphonates and specific thiophosphonate compounds so produced are disclosed and claimed. The methods start with a reaction mixture formed of a phosphonate compound, including one or more strong electron-withdrawing groups located adjacent to the phosphorus in the compound, a slight excess of Lawesson's reagent, and a polar aprotic solvent. The reaction mixture is heated until reaction is complete and may be followed with separation or hydrolyzation steps to produce thiophosphonic acids and their addition salts. One of these thio-analogues, thiophosphonoformic acid (TPFA) is particularly effective at inhibiting HIV replication and in treating mammals infected with HIV.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: December 10, 1991
    Inventor: Charles E. McKenna
  • Patent number: 5061819
    Abstract: Processes for synthesizing novel phosphonate diester compounds of the general formula ##STR1## are disclosed and claimed. The claimed process includes forming a reaction mixture of a C-14 aldehyde and a methylene-bis-phosphonic acid ester, separating a pentadienyl phosphonic acid dialkyl ester intermediate from the reaction mixture, optionally isomerizing the intermediate in the presence of a basic catalyst, and isolating the desired pentadienylphosphonic acid dialkyl ester compound. The isolated phosphonate compounds made according to the processes of the present invention may be employed in synthesizing retinoids such as retinoic acid or carotenoids such as beta-carotene.
    Type: Grant
    Filed: February 5, 1990
    Date of Patent: October 29, 1991
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 4983749
    Abstract: A process for preparing a S-substituted phosphorochloridothiolate having the formula: ##STR1## wherein R.sup.1 is a chlorine atom or an alkoxy or phenoxy group which may be substituted, and R.sup.2 is an alkyl, alkenyl, alkynyl, cycloalkyl or phenyl group which may be substituted, which comprises isomerizing an O-substituted phosphorochloridothionate having the formula: ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a Lewis acid catalyst or a phosphorus compound catalyst.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: January 8, 1991
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Tasuhiro Tsujii, Tatsuo Isogai, Takao Awazu, Tokiya Kimura
  • Patent number: 4916250
    Abstract: Novel phosphonate compounds of the formula ##STR1## are disclosed and claimed, as well as methods for manufacturing the phosphonates from C-14 through C-16 aldehydes. The phosphonate compounds of the present invention can be employed to form 13-cis retinoic acid, retin-A and beta-carotene.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: April 10, 1990
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 4812502
    Abstract: An oligomer flame-retarding additive can be defined by the general formula ##STR1## wherein: R is the hydrogen atom, or a linear or branched alkyl radical, containing from 1 to 6 carbon atoms;m takes the value 1, 2 or 3;n takes a value, or an average value, comprised within the range of from 2 to 50.Such an additive is obtained by means of the oligomerization of a hydroxyalkylenephenylphosphinic acid or of a related alkyl ester thereof.According to another form of practical embodiment, the flame-retarding additive is the product of co-oligomerization of a hydroxyalkylenephenylphosphinic acid, or of a related alkyl ester thereof, with a phenylphosphonic acid or a related alkyl ester thereof.Such oligomer additives are used for endowing a linear polyester with self-extinguishing characteristics.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: March 14, 1989
    Assignee: Enichem Sintesi, S.p.A.
    Inventors: Gioacchino Cipriani, Armando Mariano
  • Patent number: 4736050
    Abstract: A process for preparing a S-substituted phosphorochloridothiolate having the formula: ##STR1## wherein R.sup.1 is a chlorine atom or an alkoxy or phenoxy group which may be substituted, and R.sup.2 is an alkyl, alkenyl, alkynyl, cycloalkyl or phenyl group which may be substituted, which comprises isomerizing an O-substituted phosphorochloridothionate having the formula: ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a Lewis acid catalyst or a phosphorus compound catalyst.
    Type: Grant
    Filed: October 7, 1986
    Date of Patent: April 5, 1988
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Yasuhiro Tsujii, Tatsuo Isogai, Takao Awazu, Tokiya Kimura
  • Patent number: 4582652
    Abstract: Allyl phosphonate diesters are converted to vinyl phosphonate diesters by isomerization with a catalytically effective amount of one or more metal hydroxide catalysts.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: April 15, 1986
    Assignee: Allied Corporation
    Inventors: David Nalewajek, David S. Soriano