Isomerization Patents (Class 558/88)
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Patent number: 6147062Abstract: 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: GrantFiled: November 15, 1999Date of Patent: November 14, 2000Assignee: Rohm and Haas CompanyInventors: Richard Martin Jacobson, Luong Tu Nguyen
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Patent number: 6075157Abstract: 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: GrantFiled: August 17, 1998Date of Patent: June 13, 2000Assignee: Bayer CorporationInventors: Vidyanatha A. Prasad, Klaus Jelich
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Patent number: 5936113Abstract: 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: GrantFiled: December 10, 1997Date of Patent: August 10, 1999Assignee: Bayer CorporationInventors: Vidyantha A. Prasad, Klaus Jelich, Donald K. Smith
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Patent number: 5922896Abstract: 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: GrantFiled: December 10, 1997Date of Patent: July 13, 1999Assignee: Bayer CorporationInventors: Vidyanatha A. Prasad, Klaus Jelich, Donald K. Smith
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Patent number: 5489636Abstract: 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: GrantFiled: May 3, 1995Date of Patent: February 6, 1996Assignee: Ciba-Geigy CorporationInventors: Sai P. Shum, Stephen D. Pastor
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Patent number: 5489635Abstract: 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: GrantFiled: May 3, 1995Date of Patent: February 6, 1996Assignee: Ciba-Geigy CorporationInventors: Sai P. Shum, Stephen D. Pastor
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Patent number: 5473093Abstract: 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: GrantFiled: January 10, 1995Date of Patent: December 5, 1995Assignee: Akzo Nobel N.V.Inventor: Fred Jaffe
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Patent number: 5424478Abstract: 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: GrantFiled: March 22, 1994Date of Patent: June 13, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsutaka Tanaka, Tadashi Hanaoka, Kunio Takanohashi
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Patent number: 5142084Abstract: 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: GrantFiled: October 11, 1991Date of Patent: August 25, 1992Inventors: Charles G. Carter, David R. Sterrenburg
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Patent number: 5138084Abstract: 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: GrantFiled: November 14, 1990Date of Patent: August 11, 1992Assignee: SIMES Societa Italiana Medicinali e Sintetici S.p.A.Inventors: Cesare Casagrande, Francesco Santangelo
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Patent number: 5072032Abstract: 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: GrantFiled: June 21, 1989Date of Patent: December 10, 1991Inventor: Charles E. McKenna
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Patent number: 5061819Abstract: 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: GrantFiled: February 5, 1990Date of Patent: October 29, 1991Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 4983749Abstract: 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: GrantFiled: January 15, 1988Date of Patent: January 8, 1991Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Tasuhiro Tsujii, Tatsuo Isogai, Takao Awazu, Tokiya Kimura
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Patent number: 4916250Abstract: 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: GrantFiled: October 31, 1988Date of Patent: April 10, 1990Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 4812502Abstract: 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: GrantFiled: July 7, 1987Date of Patent: March 14, 1989Assignee: Enichem Sintesi, S.p.A.Inventors: Gioacchino Cipriani, Armando Mariano
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Patent number: 4736050Abstract: 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: GrantFiled: October 7, 1986Date of Patent: April 5, 1988Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Yasuhiro Tsujii, Tatsuo Isogai, Takao Awazu, Tokiya Kimura
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Patent number: 4582652Abstract: Allyl phosphonate diesters are converted to vinyl phosphonate diesters by isomerization with a catalytically effective amount of one or more metal hydroxide catalysts.Type: GrantFiled: July 2, 1984Date of Patent: April 15, 1986Assignee: Allied CorporationInventors: David Nalewajek, David S. Soriano