Reactant Having Acyclic Or Alicyclic Carbon To Carbon Unsaturation Patents (Class 558/137)
  • Patent number: 10961265
    Abstract: The present invention relates primarily to a process for preparing certain phosphorus-containing cyanohydrins of the formula (I), and also to certain phosphorus-containing cyanohydrins per se and to their use for the preparation of glufosinate and/or glufosinate salts. The present invention further relates to certain mixtures particularly suitable for preparing the phosphorus-containing cyanohydrins of the formula (I).
    Type: Grant
    Filed: July 20, 2017
    Date of Patent: March 30, 2021
    Assignee: BASF SE
    Inventors: Hans-Joachim Ressel, Kilian Tellman, Mark James Ford, Martin Littmann, Friedrich August Muehlthau, Guenter Schlegel
  • Patent number: 10316048
    Abstract: The present invention primarily relates to a process for producing certain phosphorus-containing cyanohydrin esters of formula (I) and the use thereof for producing glufosinate/glufosinate salts. The present invention further relates to a process for producing glufosinate/glufosinate salts.
    Type: Grant
    Filed: August 30, 2016
    Date of Patent: June 11, 2019
    Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
    Inventors: Hans-Joachim Ressel, Kilian Tellmann, Mark James Ford, Martin Littmann, Günter Schlegel
  • Patent number: 10196410
    Abstract: The present invention primarily relates to a process for producing certain phosphorus-containing cyanohydrin esters of formula (I) and the use thereof for producing glufosinate/glufosinate salts. The present invention further relates to a process for producing glufosinate/glufosinate salts.
    Type: Grant
    Filed: August 29, 2016
    Date of Patent: February 5, 2019
    Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
    Inventors: Hans-Joachim Ressel, Kilian Tellmann, Mark James Ford, Martin Littmann, Günter Schlegel
  • Patent number: 9850263
    Abstract: The present invention relates primarily to a process for preparing certain phosphorus-containing cyanohydrins of the formula (I), and also to certain phosphorus-containing cyanohydrins per se and to their use for the preparation of glufosinate and/or glufosinate salts. The present invention further relates to certain mixtures particularly suitable for preparing the phosphorus-containing cyanohydrins of the formula (I).
    Type: Grant
    Filed: May 8, 2015
    Date of Patent: December 26, 2017
    Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
    Inventors: Hans-Joachim Ressel, Kilian Tellman, Mark James Ford, Martin Littmann, Friedrich August Muehlthau, Guenter Schlegel
  • Publication number: 20150148556
    Abstract: The invention provides a method of forming a phosphonate diester compound from a ligand hydrolysis product (LHP) of a phosphite ligand used in a nickel-phosphite hydrocyanation catalyst, such as for conversion of 3-pentenenitrile to adiponitrile, which serves to climinate acidic LHP compound for a hydrocyanation reaction milieu where the acidic LHP can catalyze further catalyst ligand destruction. The invention further provides phosphonate disester compounds prepared by alkylation of diarylphosphite LHP in the presence of a nickel-phosphite catalyst comprising a bidentate ligand, and a continuous hydrocyanation process for production of adiponitrile wherein catalyst ligand breakdown is inhibited through inactivation of ligand hydrolysis products towards further breakdown. A method of stabilizing a hydrocyanation catalyst is provided.
    Type: Application
    Filed: May 24, 2013
    Publication date: May 28, 2015
    Applicant: INVISTA NORTH AMERICA S.A R.L.
    Inventor: William J. Tenn, III
  • Patent number: 8735477
    Abstract: The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (H) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with compounds of formula (V) to yield mono-functionalized dialkylphosphinic acid derivatives (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivatives (VI) are reacted to yield a mono-carboxyfunctionalized diakylphosphinic acid derivative (III) in the presence of a catalyst C, wherein R1, R2, R3, R4, R5, R6, R7 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X and Y are the same or different and stand independently of each for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 a
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: May 27, 2014
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20120330030
    Abstract: Provided is an enantioselective, palladium-catalyzed method for the preparation of ?-amino-?,?-unsaturated carboxylic acid derivatives having the formulas II, III, VII and VIII:
    Type: Application
    Filed: September 6, 2012
    Publication date: December 27, 2012
    Inventors: Murat Acemoglu, Andreas Pfaltz, Claude Shaerer
  • Patent number: 8318968
    Abstract: Process for preparing an alkenylphosphonic acid derivative by reacting a phosphonic acid derivative with an alkyne in the presence of a complex catalyst system and a base whose conjugate acid has a pKa in dimethyl sulfoxide (25° C., 1 bar) of at least 6.
    Type: Grant
    Filed: March 17, 2008
    Date of Patent: November 27, 2012
    Assignee: BASF SE
    Inventors: Markus Christian Biel, Roland Kessinger, Jens Sommer, Janet Bluemel
  • Patent number: 8293938
    Abstract: The invention relates to alkylphosphonous acids, salts and esters of formula (I) A-P(?O)(OX)—H (I) wherein A is C2-C20alkyl, C2-C20alkylene, and C8-C20 alkaryl are optionally substituted, and X is H, alkyl, aryl, alkylaryl, alkenyl, substituted alkyl, aryl, alkaryl, alkenyl, ammonium, primary, secondary, tertiary, quaternary alkyl and/or aryl ammonium, an alkali metal, an alkaline earth metal, a metal of the third and fourth main group and the second, fourth and eight sub-group or a metal of the lanthanoid group. The invention also relates to methods for producing same and to the uses of said compounds.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: October 23, 2012
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Harald Bauer, Werner Krause
  • Publication number: 20110213060
    Abstract: The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (H) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with compounds of formula (V) to yield mono-functionalized dialkylphosphinic acid derivatives (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivatives (VI) are reacted to yield a mono-carboxyfunctionalized diakylphosphinic acid derivative (III) in the presence of a catalyst C, wherein R1, R2, R3, R4, R5, R6, R7 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X and Y are the same or different and stand independently of each for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 a
    Type: Application
    Filed: October 6, 2009
    Publication date: September 1, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20100121092
    Abstract: Process for preparing an alkenylphosphonic acid derivative by reacting a phosphonic acid derivative with an alkyne in the presence of a complex catalyst system and a base whose conjugate acid has a pKa in dimethyl sulfoxide (25° C., 1 bar) of at least 6.
    Type: Application
    Filed: March 17, 2008
    Publication date: May 13, 2010
    Applicant: BASF SE
    Inventors: Markus Christian Biel, Roland Kessinger, Jens Sommer, Janet Bluemel
  • Patent number: 7399876
    Abstract: Process for preparing an alkenylphosphonic acid derivative by reacting a phosphonic acid derivative with an alkyne in the presence of a catalyst complex system, wherein the catalyst complex system comprises (a) nickel, (b) a phosphine having at least two trivalent phosphorus atoms and in addition (c) a phosphine having one trivalent phosphorus atom.
    Type: Grant
    Filed: November 1, 2004
    Date of Patent: July 15, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Roland Kessinger, Jan-Dirk Arndt, Jochem Henkelmann, Florian Thomas
  • Patent number: 7294733
    Abstract: An improved process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.
    Type: Grant
    Filed: June 5, 2006
    Date of Patent: November 13, 2007
    Assignee: Monsanto Technology LLC
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 7145034
    Abstract: The invention relates to a process for preparing N-phosphono-methylglycine by reacting a hexahydrotriazine compound with a triacyl phosphite in an organic solvent, hydrolyzing the resulting phosphono compound after prior extraction into an aqueous phase and separation from the organic phase. The process avoids decomposition of the organic solvent during hydrolysis.
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: December 5, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Christian Wulff, Stefan Orsten, Alfred Oftring, Peter Zehner
  • Patent number: 7119220
    Abstract: Process for preparing dimethyl propanephosphonate, characterized in that dimethyl phosphite is reacted with propene in the presence of a free-radical former at a reaction temperature of 60 to 95° C., the half life of the free-radical former being 0.1 to 20 min at the reaction temperature.
    Type: Grant
    Filed: February 21, 2003
    Date of Patent: October 10, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jan-Gerd Hansel, Gert Jabs, Johannes Kaulen, Hans-Georg Adams, Hans-Günter Fröhlen
  • Patent number: 7091376
    Abstract: An improved process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.
    Type: Grant
    Filed: June 15, 2004
    Date of Patent: August 15, 2006
    Assignee: Monsanto Technology LLC
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 6765107
    Abstract: The present invention relates to a new manufacturing method for phosphonate esters, which have utility as a carbon-carbon binding formation agent, as well as a synthesis intermediate for biologically active substances such as medical drugs and agri-chemicals. Specifically the present invention relates to a new industrially advantageous manufacturing method for phosphonate esters in which the phosphonate esters of the subject can be efficiently obtained with a high yield rate through a simple operation while having barely any side reaction or sub-product. More specifically, the present invention pertains to a manufacturing method for phosphonate esters in which secondary phosphonate esters and alkene compounds are reacted in a transition metal catalyst. In addition the present invention relates to a new manufacturing method for allylphosphonate esters in which secondary cyclic phosphonate esters and 1,3-diene compounds are reacted in a palladium catalyst.
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: July 20, 2004
    Assignees: National Institute of Advanced Industrial Science and Technology, Japan Science and Technology Agency
    Inventors: Li-Biao Han, Farzad Mirzaei, Masato Tanaka
  • Patent number: 6534669
    Abstract: Alkenylphosphonic acid derivatives are prepared by reacting phosphonic acid derivatives with alkynes in the presence of a metal complex catalyst system comprising (a) nickel and (b) a phosphine having at least two trivalent phosphorus atoms.
    Type: Grant
    Filed: November 1, 2001
    Date of Patent: March 18, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Jochem Henkelmann, Katrin Klass, Jan-Dirk Arndt
  • Patent number: 6278012
    Abstract: The present invention relates to a process for the preparation of phosphinic acid esters, which comprises a) reacting elemental yellow phosphorus with alkylating agents in the presence of a base to give a mixture which comprises, as principal constituents, the (metal) salts of alkylphosphonous, phosphorous and hypophosphorous acids, b) esterifying the principal constituents of the mixture from a) to give an ester mixture, c) isolating the ester of the alkylphosphonous acid from the ester mixture, d) adding the resultant ester of the alkylphosphonous acid onto an olefin containing a functional group. The invention likewise relates to the use of the phosphinic acid esters prepared by this process, inter alia as flame retardants and precursors for further syntheses.
    Type: Grant
    Filed: May 24, 2000
    Date of Patent: August 21, 2001
    Assignee: Clariant GmbH
    Inventors: Sebastian Hörold, Norbert Weferling, Heinz-Peter Breuer, Martin Sicken
  • Patent number: 6218570
    Abstract: An improved process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: April 17, 2001
    Assignee: Monsanto Company
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 6111127
    Abstract: A process for the preparation of an unsaturated phosphonic acid ester of the formula:R.sup.1 CH.dbd.C(R.sup.2)P(.dbd.O)(OR.sup.3).sub.2wherein an acetylene compound of the formula:R.sup.1 C.tbd.CR.sup.2is reacted with a secondary phosphite of the formula:HP(.dbd.O)(OR.sup.3).sub.2in the presence of a palladium complex catalyst. The process is characterized in that the reaction is performed in the presence of water or in that the palladium complex catalyst contains, as a ligand, a 1,3-bisphosphinopropane of the formula: ##STR1## wherein R.sup.4, R.sup.5, R.sup.6 and R.sup.7 stand, independently from each other, for an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group.
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: August 29, 2000
    Assignees: Agency of Industrial Science & Technology, Masato Tanaka
    Inventors: Masato Tanaka, Li-Biao Han
  • Patent number: 6090968
    Abstract: The present invention relates to a process for preparing phosphinic esters which comprisesa) reacting elemental yellow phosphorus with alkyl halides in the presence of alkali metal hydroxide or alkaline earth metal hydroxide to form a mixture which comprises as main constituents the alkali metal salts and/or alkaline earth metal salts of alkylphosphonous acid, phosphorous acid and hypophosphorous acidb) removing the alkylphosphonous acid from the mixture obtained as described in a),c) esterifying the alkylphosphonous acid,d) adding the resultant ester of the alkylphosphonous acid to a compound having at least one C.dbd.C double bond.The invention likewise relates to the use of the phosphinic esters prepared by this process inter alia as flame retardants and as precursor for further syntheses.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: July 18, 2000
    Assignee: Clariant GmbH
    Inventors: Sebastian Horold, Norbert Weferling, Heinz-Peter Breuer
  • Patent number: 6054608
    Abstract: A process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.
    Type: Grant
    Filed: May 1, 1998
    Date of Patent: April 25, 2000
    Assignee: Monsanto Company
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 5847185
    Abstract: Allenic phosphonate reagent compositions are described which have the formula: ##STR1## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups, or R, R'=(CH.sub.2).sub.n (n=2 or 3) or ?CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 !.Also described are methods for forming such allenic phosphonates from ethynyl-.beta.-ionol, and for converting these allenic compounds to allylic phosphonate compounds which can be used in the synthesis of a variety of biologically-active materials.
    Type: Grant
    Filed: November 21, 1997
    Date of Patent: December 8, 1998
    Assignee: Loyola University of Chicage
    Inventor: James H. Babler
  • Patent number: 5648509
    Abstract: The addition of acid diesters of phosphorous acid onto alpha,beta-unsaturated carboxylic acid derivatives under basic catalysis is achieved with good yields if it is carried out in the presence of alkali metal alcoholates or phenolates and in the presence of halides, oxides or hydroxides of divalent metals. Co-use of these metal compounds allows relatively small mounts of metal alcoholates or phenolates to be used. The resulting reaction mixtures do not contain relatively large amounts of troublesome by-products.
    Type: Grant
    Filed: July 27, 1995
    Date of Patent: July 15, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Salman Dermeik, Martina Wanner, Karl-Heinz Lemmer, Reinhold Braun
  • Patent number: 5420329
    Abstract: The invention relates to a process for the enantioselective preparation of L-phosphinothricin (L-Ptc) and derivatives of the formula I ##STR1## in which R.sup.1 is H, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.3 -C.sub.6)-cycloalkyl or (subst.) phenyl-(C.sub.1 -C.sub.4)-alkyl, R.sup.2 is hydrogen, formyl, [(C.sub.1 -C.sub.6)alkyl]carbonyl, [(C.sub.1 -C.sub.6)alkoxy]carbonyl, (subst.) benzyloxycarbonyl, (C.sub.1 -C.sub.6)-alkylsulfonyl or (subst.) (C.sub.6 -C.sub.10)-arylsulfonyl, and R.sup.3 is OH, NH.sub.2 or (C.sub.1 -C.sub.6)-alkoxy, or their salts with acids or bases.
    Type: Grant
    Filed: July 25, 1994
    Date of Patent: May 30, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Jaochim Zeiss
  • Patent number: 5210262
    Abstract: A method is provided for preparing a phosphonic acid ester having the structure ##STR1## wherein R.sup.1 is farnesyl or a derivative or analog thereof, and R.sup.2 is lower alkyl, by treating a farnesyl halide R.sup.1 Hal(Hal=Cl,Br,I) with an alkoxide of the structure ##STR2## wherein M is an alkali metal and R.sup.2c is lower alkyl. The resulting phosphonic acid ester is an intermediate in preparing a squalene synthetase inhibitor which is used for inhibiting cholesterol biosynthesis.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: May 11, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Janak Singh, Richard H. Mueller
  • Patent number: 5166386
    Abstract: Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthesis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents, are provided which have the structure ##STR1## wherein R.sup.2 is a metal ion, lower alkyl or H;R.sup.3 is a metal ion or lower alkyl;R is R.sup.1 --(CH.sub.2).sub.n --, R.sup.1 --(CH.sub.2).sub.m --O-- orR.sup.1 --(CH.sub.2).sub.m --OCH.sub.2 --, wherein n is 1 to 4 and m is 0 to 3, andR.sup.1 is R.sup.5 --Q.sup.1 --Q.sup.2 --Q.sup.3 --wherein R.sup.5, Q.sup.1, Q.sup.2 and Q.sup.3 are as defined herein.New intermediates, new methods of preparation and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: November 24, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Scott A. Biller
  • Patent number: 4599207
    Abstract: The invention relates to a new process for the preparation of compounds of the formula (I) ##STR1## in which R.sub.1 denotes alkyl and R.sub.2 denotes H, acetyl or propionyl, by addition of compounds of the formula II ##STR2## onto compounds of the formula III, using radical-formers, the radical-formers being used being compounds of the general formula IV ##STR3## in which R.sub.3 denotes alkyl or phenyl and R.sub.4 denotes alkyl, the reaction being carried out at temperatures in the range from 50.degree. to 100.degree. C., and, for the preparation of compounds of the formula I where R.sub.2 is H, then splitting off the radical R.sub.2.sup.'. Using this process, the compounds of the formula I are obtained in high yield and particular purity.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: July 8, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Stephen Lachhein, Hilmar Mildenberger
  • Patent number: 4594199
    Abstract: A method is provided for preparing phosphinic acid prodrug intermediates which are useful in preparing phosphinic acid angiotensin-converting enzyme inhibitors which method includes the step of coupling a phosphonous acid or its ester of the structure ##STR1## wherein R is H or lower alkyl and R.sup.1 is lower alkyl, aryl, arylalkyl, cycloalkyl or cycloalkylalkyl, with a conjugated compound of the structure ##STR2## wherein R.sup.2, R.sup.3 and R.sup.4 may be the same or different and each is independently H, lower alkyl or aryl, and Z is --CO.sub.2 R.sup.5 (wherein R.sup.5 is H or lower alkyl), ##STR3## (wherein R.sup.6 is H, lower alkyl aryl or arylalkyl), ##STR4## (wherein R.sup.7 and R.sup.8 are the same or different and are selected from the group consisting of H, lower alkyl, aryl, aryl-lower alkyl, cycloalkyl or cycloalkylalkyl and at least one of R.sup.7 and R.sup.8 is other than H, or R.sup.7 and R.sup.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: June 10, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: John K. Thottathil