Attaching Cyano To The Carbonyl Carbon Of An Aldehyde Or Ketone (e.g., Cyanohydrin Formation, Etc.) Patents (Class 558/351)
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Patent number: 10899706Abstract: The present invention relates to a method for preparing methionine or methionine salts. In particular, the invention describes the step of preparing 2-hydroxy-4-(methylthio)butyronitrile (MMP-CN) from 3-methylthiopropanal (MMP) and hydrogen cyanide (HCN) in the presence of ammonia by bringing a gaseous mixture comprising HCN and ammonia into contact with MMP.Type: GrantFiled: December 15, 2017Date of Patent: January 26, 2021Assignee: Evonik Operations GmbHInventors: Judith Hierold, Daniel Sudhoff, Martin Steurenthaler, Hans Joachim Hasselbach, Philipp Roth, Thorsten Merker, Markus Held, Daniel Fischer, Christian Kaiser
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Patent number: 10774038Abstract: A process for producing cyanonorbornene of the present invention includes Step 1 of preparing a mixture solution including 0.5% by weight to 28% by weight of methyl bicyclononadiene, with respect to a total amount of 100% by weight of dicyclopentadiene, acrylonitrile, and the methyl bicyclononadiene, in a container, and Step 2 of reacting the bicyclopentadiene with the acrylonitrile in the presence of the methyl bicyclononadiene, in the mixture solution.Type: GrantFiled: July 23, 2018Date of Patent: September 15, 2020Assignee: MITSUI CHEMICALS, INC.Inventors: Shigetoshi Kuma, Tomoya Sanda
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Patent number: 9126900Abstract: A process for producing a mandelonitrile compound represented by the following formula (2), comprising a step of reacting a benzaldehyde compound represented by the following formula (1) with at least one member selected from the group consisting of metal cyanides and hydrogen cyanide in the presence of a phase transfer catalyst in a solvent.Type: GrantFiled: March 26, 2012Date of Patent: September 8, 2015Assignee: Sumitomo Chemical Company, LimitedInventor: Tatsuya Toriumi
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Patent number: 8729288Abstract: A method for the production of 2-hydroxy-4-(methylthio)butyronitrile having good storage stability in a multi-zone reactor, is provided. 3-methylmercaptopropionaldehyde is reacted with hydrogen cyanide in the presence of a base as catalyst in a main reaction zone of the multizone reactor to form a reaction mixture comprising the 2-hydroxy-4-(methylthio)butyronitrile, unreacted 3-methylmercaptopropionaldehyde, the catalyst and residual amounts of gaseous hydrogen cyanide. The residual gaseous hydrogen cyanide is removed from the main reaction zone to an absorption and post-reaction zone of the reactor which comprises a mixture of 3-methylmercaptopropionaldehyde and the catalyst; and the gaseous hydrogen cyanide is further reacted with the 3-methylmercaptopropionaldehyde in the absorption and post reaction zone. A molar ratio of hydrogen cyanide to 3-(methylthio)propanal in the main reaction zone is from 0.98 to 1.03.Type: GrantFiled: February 22, 2012Date of Patent: May 20, 2014Assignee: Evonik Degussa GmbHInventors: Dieter Buss, Martin Steurenthaler, Michael R. Rinner, Stephan Kretz, Hans Joachim Hasselbach, Caspar-Heinrich Finkeldei, Martin Koerfer, Pablo Zacchi
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Patent number: 8471053Abstract: A process according to the present invention for producing a cyanohydrin compound flow-reacts a carbonyl compound with hydrogen cyanide in the presence of a catalyst, and can therefore reduce the residence time. This makes it possible to reduce the period of time over which the resulting cyanohydrin compound is exposed to an unreacted portion of the carbonyl compound. As a result, the resulting cyanohydrin compound can be prevented from reacting with the unreacted portion. This makes it possible to produce the cyanohydrin compound in good yield. That is, the process according to the present invention for producing a cyanohydrin compound produces a cyanohydrin compound in good yield from a carbonyl compound and hydrogen cyanide.Type: GrantFiled: October 21, 2008Date of Patent: June 25, 2013Assignee: Nippoh Chemicals Co., Ltd.Inventors: Yuichiro Kinoshita, Naoki Fujiwara, Kazuya Nakagawa, Koji Midorikawa
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Patent number: 8440852Abstract: The invention relates to a process for preparing tetraethylenepentamine (TEPA) by hydrogenation of diethylenetriaminediacetonitrile (DETDN) over a catalyst. If appropriate, DETDN can also be present as a constituent of an amino nitrile mixture which additionally comprises diethylenetriaminemonoacetonitrile (DETMN).Type: GrantFiled: February 27, 2008Date of Patent: May 14, 2013Assignee: BASF SEInventors: Kirsten Dahmen, Alfred Oftring, Randolf Hugo, Thilo Hahn, Katrin Baumann, Johann-Peter Melder
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Patent number: 8334399Abstract: The present invention relates in general terms to a process for preparing acetone cyanohydrin, comprising as steps: A. contacting acetone and hydrocyanic acid in a reactor to give a reaction mixture, the reaction mixture being circulated, to obtain acetone cyanohydrin; B. cooling at least some of the reaction mixture by flowing it through a cooling region of a cooler, the cooler including one cooling element or at least two cooling elements; C.Type: GrantFiled: August 31, 2007Date of Patent: December 18, 2012Assignee: Evonik Röhm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Patent number: 8309753Abstract: A method of producing an optically active cyanohydrin compound represented by formula (3), which includes reacting an aldehyde compound represented by formula (2) with hydrogen cyanide in the presence of a silyl compound and an asymmetric complex which is obtained by reacting an optically active pyridine compound represented by formula (1) with an aluminum halide, and wherein Q1, Q2, R1 and R2 are defined in the specification.Type: GrantFiled: April 3, 2009Date of Patent: November 13, 2012Assignee: Sumitomo Chemical Company, LimitedInventor: Koichi Nakazawa
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Patent number: 8263796Abstract: A process according to the present invention for producing a cyanohydrin compound is a process for producing a cyanohydrin compound by performing a reaction between a carbonyl compound such as an aldehyde compound and hydrogen cyanide in the presence of a catalyst, a content of the carbonyl compound in a reaction system being not more than 50 mol % with respect to the cyanohydrin compound. Thus provided is a process for producing a cyanohydrin compound in good yield from an aldehyde compound and hydrogen cyanide.Type: GrantFiled: October 21, 2008Date of Patent: September 11, 2012Assignee: Nippoh Chemicals Co., Ltd.Inventors: Naoki Fujiwara, Kazuya Nakagawa, Yuichiro Kinoshita, Koji Midorikawa
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Publication number: 20120215022Abstract: A method for the production of 2-hydroxy-4-(methylthio)butyronitrile having good storage stability in a multi-zone reactor, is provided. 3-methylmercaptopropionaldehyde is reacted with hydrogen cyanide in the presence of a base as catalyst in a main reaction zone of the multizone reactor to form a reaction mixture comprising the 2-hydroxy-4-(methylthio)butyronitrile, unreacted 3-methylmercaptopropionaldehyde, the catalyst and residual amounts of gaseous hydrogen cyanide. The residual gaseous hydrogen cyanide is removed from the main reaction zone to an absorption and post-reaction zone of the reactor which comprises a mixture of 3-methylmercaptopropionaldehyde and the catalyst; and the gaseous hydrogen cyanide is further reacted with the 3-methylmercaptopropionaldehyde in the absorption and post reaction zone. A molar ratio of hydrogen cyanide to 3-(methylthio)propanal in the main reaction zone is from 0.98 to 1.03.Type: ApplicationFiled: February 22, 2012Publication date: August 23, 2012Applicant: Evonik Degussa GmbHInventors: Dieter Buss, Martin Steurenthaler, Michael R. Rinner, Stephan Kretz, Hans Joachim Hasselbach, Caspar-Heinrich Finkeldei, Martin Koerfer, Pablo Zacchi
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Patent number: 8163947Abstract: The present invention can provide a cyanation catalyst represented by the general formula (I): (in the formula (I), R1 through R4 are each an optionally substituted hydrocarbon group; R1 and R2 and/or R3 and R4 may form an optionally substituted carbon chain ring; R5 through R8 are each a hydrogen atom, or an optionally substituted hydrocarbon group; R5 and R6 and/or R7 and R8 may form an optionally substituted carbon chain ring; R9 and R10 are each a hydrogen atom, or an optionally substituted hydrocarbon group; W, X and Y each represent an optionally substituted binding chain; X and/or Y may be non-existent; M represents a metal or a metal ion; and ligands of M may each be located at any position).Type: GrantFiled: February 14, 2008Date of Patent: April 24, 2012Assignees: National University Corporation, Hokkaido University, Mitsubishi Rayon Co., Ltd.Inventors: Takeshi Ohkuma, Nobuhito Kurono
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Patent number: 8143434Abstract: The present invention relates in general terms to a process for preparing acetone cyanohydrin, comprising as steps: A. contacting acetone and hydrocyanic acid in a reactor to give a reaction mixture, the reaction mixture being circulated, to obtain acetone cyanohydrin; B. cooling at least some of the reaction mixture; C. discharging at least a portion of the acetone cyanohydrin obtained from the reactor; D. continuously distilling the discharged acetone cyanohydrin obtained to obtain an acetone cyanohydrin bottom product and an acetone top product in a distillation column; E. recycling at least a portion of the acetone top product into step A, the acetone top product being kept at less than 60° C.Type: GrantFiled: August 31, 2007Date of Patent: March 27, 2012Assignee: Evonik Röhm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Patent number: 8128898Abstract: A process (10) for at least partially removing hydrogen cyanide from synthesis gas includes feeding a synthesis gas (30) containing hydrogen cyanide to a gas-liquid contacting stage (18) and, in the gas-liquid contacting stage (18), contacting the synthesis gas with an aqueous washing solution (36) comprising at least one dissolved metal salt, with metal cations of the metal salt being capable of forming metal cyanide complexes and/or metal cyanide precipitates, and weak acid anions of the metal salt serving to buffer the pH of the washing solution in a range between 6 and 10. Hydrogen cyanide is washed from the synthesis gas by the washing solution to form a treated synthesis gas (38) and a spent washing solution (40). From time to time or continuously, at least a portion of the spent washing solution is withdrawn from the gas-liquid contacting stage. The treated synthesis gas (38) is also withdrawn from the gas-liquid contacting stage.Type: GrantFiled: October 29, 2007Date of Patent: March 6, 2012Assignee: Sasol Techonology (Proprietary) LimitedInventors: Braam Van Dyk, John Marriott, Bavanethan Pillay, Hendrik Johannes Van Der Westhuizen, Ronél Combrink, Trevor David Phillips, Denise Louisette Venter, André´ Peter Steynberg
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Patent number: 8129559Abstract: The invention relates to a process for preparing acetone cyanohydrin and to a process for preparing alkyl methacrylates, in which an acetone cyanohydrin as can be prepared in accordance with the present invention is used.Type: GrantFiled: August 31, 2007Date of Patent: March 6, 2012Assignee: Evonik Röhm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Patent number: 7999129Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.Type: GrantFiled: December 9, 2008Date of Patent: August 16, 2011Assignee: Les Laboratories ServierInventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
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Patent number: 7994359Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.Type: GrantFiled: November 26, 2008Date of Patent: August 9, 2011Assignee: Les Laboratoires ServierInventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
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Publication number: 20110033362Abstract: The present invention relates to an improved process for producing hydrocyanic acid by reaction of ammonia with methane in which a small amount of at least one sulphur-containing compound corresponding to the general formula R S (S)x—R? is added, in which R and R? which are identical or different, represent a linear or branched alkyl or alkenyl radical containing from 1 to 5 carbon atoms, and x is a number ranging from 1 to 5, to the reactive gas mixture before it passes over the catalyst. The process according to the invention makes it possible to obtain improved yields of HCN. Another subject of the invention relates to the use of the resulting product for producing methionine, acetone cyanohydrin, adiponitrile or sodium cyanide.Type: ApplicationFiled: March 20, 2009Publication date: February 10, 2011Applicant: ARKEMA FRANCEInventors: Enzo Formentin, Catherine Schafer
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Publication number: 20110034718Abstract: A method of producing an optically active cyanohydrin compound represented by formula (3) (wherein, Q1 and Q2 are as defined below, and * represents that the indicated carbon atom is the optically active center) comprising reacting an aldehyde compound represented by formula (2) (wherein, Q1 and Q2 represent each independently a hydrogen atom, optionally substituted alkyl group having 1 to 6 carbon atoms, or the like) with hydrogen cyanide in the presence of a silyl compound and an asymmetric complex which is obtained by reacting an optically active pyridine compound represented by formula (1) (wherein, R1 and R2 represent each independently a hydrogen atom, alkyl group having 1 to 6 carbon atoms, or the like, provided that R1 and R2 are not the same.) with an aluminum halide.Type: ApplicationFiled: April 3, 2009Publication date: February 10, 2011Inventor: Koichi Nakazawa
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Publication number: 20100261929Abstract: A process according to the present invention for producing a cyanohydrin compound flow-reacts a carbonyl compound with hydrogen cyanide in the presence of a catalyst, and can therefore reduce the residence time. This makes it possible to reduce the period of time over which the resulting cyanohydrin compound is exposed to an unreacted portion of the carbonyl compound. As a result, the resulting cyanohydrin compound can be prevented from reacting with the unreacted portion. This makes it possible to produce the cyanohydrin compound in good yield. That is, the process according to the present invention for producing a cyanohydrin compound produces a cyanohydrin compound in good yield from a carbonyl compound and hydrogen cyanide.Type: ApplicationFiled: October 21, 2008Publication date: October 14, 2010Inventors: Yuichiro Kinoshita, Naoki Fujiwara, Kazuya Nakagawa, Koji Midorikawa
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Publication number: 20100256409Abstract: A process according to the present invention for producing a cyanohydrin compound is a process for producing a cyanohydrin compound by performing a reaction between a carbonyl compound such as an aldehyde compound and hydrogen cyanide in the presence of a catalyst, a content of the carbonyl compound in a reaction system being not more than 50 mol % with respect to the cyanohydrin compound. Thus provided is a process for producing a cyanohydrin compound in good yield from an aldehyde compound and hydrogen cyanide.Type: ApplicationFiled: October 21, 2008Publication date: October 7, 2010Inventors: Naoki Fujiwara, Kazuya Nakagawa, Yuichiro Kinoshita, Koji Midorikawa
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Publication number: 20100076214Abstract: The invention relates to a process for preparing acetone cyanohydrin and to a process for preparing alkyl methacrylates, in which an acetone cyanohydrin as can be prepared in accordance with the present invention is used.Type: ApplicationFiled: August 31, 2007Publication date: March 25, 2010Applicant: Evonik Roehm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Publication number: 20100069594Abstract: The present invention relates in general terms to a process for preparing acetone cyanohydrin, comprising as steps: A. contacting acetone and hydrocyanic acid in a reactor to give a reaction mixture, the reaction mixture being circulated, to obtain acetone cyanohydrin; B. cooling at least some of the reaction mixture; C. discharging at least a portion of the acetone cyanohydrin obtained from the reactor; D. continuously distilling the discharged acetone cyanohydrin obtained to obtain an acetone cyanohydrin bottom product and an acetone top product in a distillation column; E. recycling at least a portion of the acetone top product into step A, the acetone top product being kept at less than 60° C.Type: ApplicationFiled: August 31, 2007Publication date: March 18, 2010Applicant: Evonik Roehm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Publication number: 20100029977Abstract: The present invention can provide a cyanation catalyst represented by the general formula (I): (in the formula (I), R1 through R4 are each an optionally substituted hydrocarbon group; R1 and R2 and/or R3 and R4 may form an optionally substituted carbon chain ring; R5 through R8 are each a hydrogen atom, or an optionally substituted hydrocarbon group; R5 and R6 and/or R7 and R8 may form an optionally substituted carbon chain ring; R9 and R10 are each a hydrogen atom, or an optionally substituted hydrocarbon group; W, X and Y each represent an optionally substituted binding chain; X and/or Y may be non-existent; M represents a metal or a metal ion; and ligands of M may each be located at any position).Type: ApplicationFiled: February 14, 2008Publication date: February 4, 2010Applicants: National University Corporation Hokkaido University, Mitsubishi Rayon Co., Ltd.Inventors: Takeshi Ohkuma, Nubuhito Kurono
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Patent number: 7544839Abstract: Process for the industrial synthesis and new crystalline form of the compound of formula (I): Medicinal products containing the same which are useful in treating disorders of the melatoninergic system.Type: GrantFiled: April 6, 2007Date of Patent: June 9, 2009Assignee: Les Laboratoires ServierInventors: Jean-Claude Souvie, Isaac Gonzalez-Blanco, Gilles Thominot, Genevieve Chapuis, Stephane Horvath, Gerard Damien
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Patent number: 7479569Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.Type: GrantFiled: February 4, 2005Date of Patent: January 20, 2009Assignee: Les Laboratoires ServierInventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
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Patent number: 7476751Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.Type: GrantFiled: February 7, 2005Date of Patent: January 13, 2009Assignee: Les Laboratoires ServierInventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
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Patent number: 7256315Abstract: Process for the Production of 3-methylthiopropanal. A process for the production of 3-methylthiopropanal which reacting reaction medium comprising methyl mercaptan and acrolein in the presence of a catalyst comprising an organic base characterised in that the organic base is a N-alkyl morpholine compound.Type: GrantFiled: October 14, 2003Date of Patent: August 14, 2007Assignee: Adisseo Ireland Ltd.Inventor: Patrick Rey
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Patent number: 7202075Abstract: New genes containing a DNA sequence coding for hydroxynitrile lyase, which genes can be prepared via a primer combination based on the DNA sequence of the 5?-region of the mdl genes from the Prunus serotina and from Prunus amygdalus and/or a primer 2 based on the 3?-region of the DNA sequences of one of the hydroxynitrile lyase isoenzymes from Prunus serotina or from Prunus amygdalus, subsequent amplification with a DNA polymerase using a DNA from organisms, containing genes coding for hydroxynitrile lyase, as templates and cloning, and also recombinant proteins which can be prepared in suitable host cells by heterologous expression of the DNA sequence of said HNL genes, and proteins and fusion proteins derived therefrom and use of said proteins for preparing (R)- or (S)-cyanohydrins.Type: GrantFiled: September 15, 2004Date of Patent: April 10, 2007Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KGInventors: Helmut Schwab, Anton Glieder, Christoph Kratky, Ingrid Dreveny, Rodolfo Bona, Peter Pöchlauer, Wolfgang Skranc, Herbert Mayrhofer, Irma Wirth, Rudolf Neuhofer
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Patent number: 6909011Abstract: A process for preparing protected, enantiomer-enriched cyanohydrins of the formula where R1 and R2 independently of one another can be an unsubstituted, monosubstituted or polysubstituted C1-C20-alkyl, C5-C20-aryl, C5-C20-heteroaryl, C5-C20-alkaryl, C5-C20-alkylheteroaryl or C5-C20-aralkyl radical or an unsubstituted, monosubstituted or polysubstituted C5-C20-heterocycle, or C5-C20-alkylheterocycle or together can be an unsubstituted or substituted C4-C20-alkylene radical, which can contain one or more heteroatoms in the chain, or one of the radicals is hydrogen, and R3 can be an unsubstituted or substituted C1-C20-alkyl, C5-C20-aryl or C5-C20-heteroaryl radical, by reacting an aldehyde or ketone of the formula where R1 and R2 are defined as above, in the presence of an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or 2-phase system or in emulsion at a temperature of ?5 to +40° C. with a carbonic ester nitrile of the formula where R3 is defined as above.Type: GrantFiled: December 23, 2002Date of Patent: June 21, 2005Assignee: DSM Fine Chemicals Austria NFG GmbH & CO KGInventors: Wolfgang Skranc, Peter Poechlauer, Irma Wirth, Rudolf Neuhofer, Herbert Mayrhofer
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Patent number: 6743938Abstract: This process for the production of the methyl ethyl ketone cyanohydrin of formula (I) is characterized by the fact that hydrocyanic acid and methyl ethyl ketone are reacted in the presence of diethylamine as a catalyst.Type: GrantFiled: August 2, 2002Date of Patent: June 1, 2004Assignee: AtofinaInventors: Jean-Francois Croizy, Marc Esch, Gilbert Esquirol
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Patent number: 6717006Abstract: The invention relates to the production of (R)-enantiomeric, optically active cyanohydrins by reacting an aldehyde or a ketone with a cyanide group donor in the presence of (R) oxynitrilase, wherein a reaction mixture comprising a) an aldehyde or a ketone dissolved in an organic solvent; said organic solvent is immiscible or only slightly miscible with water, b) any aqueous R)-oxynitrilase solution and c) a cyanide group donor is stirred in such away that an emulsion is formed which remains intact until the end of the enzymatic reaction. After the enzymatic reaction has terminated, the (R)-cyanohydrin is isolated from the reaction mixture.Type: GrantFiled: June 10, 2002Date of Patent: April 6, 2004Assignee: DSM Fine Chemicals Austria Nfg GmbH & Co KGInventors: Peter Pöchlauer, Irma Wirth, Herbert Mayrhofer, Rudolf Neuhofer
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Patent number: 6653498Abstract: The present invention relates to a process for preparing optically active cyanohydrins of the formula (II), by reacting an aldehyde of the formula (I) with HCN in a water-immiscible organic solvent in the presence of water, in the absence or presence of a buffer, in the presence of a (R)-hydroxynitrile lyase, where X, Y and Z in formula (II) have the same meaning as in formula (I), independently of each other are identical or different and are H, F, Cl, Br, I, OH, O(C1-C4-alkyl), OCOCH3, NHCOCH3, NO2 or C1-C4-alkyl.Type: GrantFiled: November 1, 2001Date of Patent: November 25, 2003Assignee: Clariant GmbHInventors: Bettina Kirschbaum, Goetz Wilbert, Franz Effenberger
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Patent number: 6417385Abstract: Acetone-cyanhydrin can be produced in a gas-liquid reactor from a hydrogen cyanide-containing gas, especially the crude gas originating from a methane-ammonia (BMA) or Andrussow process, and acetone in the presence of a base. The aim of the invention is to overcome the disadvantages of the methods for producing acetone-cyanhydrin known from the art. To this end, the gaseous phase removed from the reactor is liberated from the unreacted acetone and hydrogen cyanide in a gas purifier that is operated with a high-boiling solvent, especially with stabilized acetone-cyanhydrin, and the washed phase is fed to the gas-liquid reactor.Type: GrantFiled: December 28, 2001Date of Patent: July 9, 2002Assignee: Degussa AGInventors: Walter Börner, Liane Deusser, Ralph Marquardt, Rudolf Vanheertum, Karl-Heinz Vieweg
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Publication number: 20020087024Abstract: The invention relates to a continuous process, carried out in two steps, for the cyanoalkylation of compounds having one or more NH functions by reaction thereof with carbonyl compounds and hydrocyanic acid, in which the first step is carried out without pressure at a temperature which is below the boiling point of the reaction mixture.Type: ApplicationFiled: October 5, 2001Publication date: July 4, 2002Applicant: BASF AktiengesellschaftInventors: Thomas Greindl, Gerold Braun, Friedrich Wirsing, Georg Krug
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Patent number: 6258966Abstract: A chiral ligand of the formula (II) or formula (II′), was synthesized. The chiral ligand (II) or formula (II′) can chelate to metals to form a catalytic complex to catalyze the addition of trimethylsilyl cyanide to aldehydes to give optically active cyanohydrin, individually.Type: GrantFiled: October 13, 1999Date of Patent: July 10, 2001Assignee: Everlight USA, Inc.Inventors: Biing-Jiun Uang, Chun-Tzu Yang
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Patent number: 6111128Abstract: In the presence of a metal catalyst such as a samarium compound, an enol ester compound shown by the formula (1) is reacted with a carbonyl compound shown by the formula (3) and a cyanogenation agent to produce an .alpha.-cyanohydrin ester shown by the formula (4): ##STR1## wherein R.sup.1, R.sup.7, and R.sup.8 are the same or different from each other, each representing a non-reactive atom or a non-reactive organic group; R.sup.2, R.sup.3, and R.sup.4 are the same or different from each other, each representing a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.By hydrolyzing the obtained compound, the corresponding .alpha.-hydroxy acid or a salt thereof can be obtained. According to the above processes, an .alpha.-cyanohydrin ester and an .alpha.-hydroxy acid can be obtained in high yields.Type: GrantFiled: December 17, 1998Date of Patent: August 29, 2000Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 6054065Abstract: A chiral ligand of the formula (I) or formula (I'), ##STR1## was synthesized. The chiral ligand (I) or formula (I') can chelate to metals to form a catalytic complex to catalyze the addition of trimethylsilyl cyanide to aldehydes to give optically active cyanohydrin, each individually.Type: GrantFiled: July 19, 1999Date of Patent: April 25, 2000Inventors: Biing-Jiun Uang, Chyuan-Der Hwang
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Patent number: 6040471Abstract: This invention relates to a process for making certain acetonitriles.Type: GrantFiled: October 15, 1998Date of Patent: March 21, 2000Assignee: SmithKline Beecham CorporationInventor: Ann Marie Diederich
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Patent number: 5885809Abstract: A method for producing (S)-cyanohydrins of general formula ##STR1## in which R and R' independently represent (1) hydrogen; (2) a substituted or unsubstituted saturated alkyl group which may include amine, imine, hydroxy, C.sub.1 -C.sub.8 -alkoxy, halogen, carboxyl, C.sub.3 -C.sub.20 -cycloalkyl groups and/or a N,O,S-heteroatom-substituted aromatic ring as substituent; (3) a substituted or unsubstituted, singly or multiply unsaturated alkenyl- or alkinyl group which may include one or several amine, imine, hydroxy, C.sub.1 -C.sub.8 -alkoxy, halogen, carboxyl, C.sub.3 -C.sub.20 -cycloalkyl groups and/or one optionally N,O,S-heteroatom-substituted aromatic ring as substituents; (4) a substituted or unsubstituted aromatic or heteroaromatic group.Type: GrantFiled: February 7, 1997Date of Patent: March 23, 1999Assignee: Degussa AktiengesellschaftInventors: Franz Effenberger, Harald Wajant, Siegfried Forster, Jurgen Roos
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Patent number: 5780665Abstract: Halomethylbenzoyl cyanides IPH--CO--CN (I)where Ph is phenyl which is substituted by chloromethyl or bromomethyl and may cary 1-4 other rradicals, are prepared from halomethylbenzoyl chlorides IIPH--CO--Cl (II),by reacting II with a cyanide-donating compound in the presence of a Lewis acid, if required in an inert organic solvent or diluent, and then isolating the product.The halomethylbenzoyl cyanides I are important intermediates for synthesizing crop protection agents.Type: GrantFiled: May 6, 1997Date of Patent: July 14, 1998Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Michael Keil, Bernd Wolf, Horst Wingert, Thomas Wettling
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Patent number: 5763639Abstract: A process for preparing quaternized glycine nitriles of formula I ##STR1## comprising reaction of the corresponding precursor amine, aldehyde, hydrocyanic acid or alkali metal cyanide, and subsequent quaternization with an alkylating agent, wherein the reaction and quaternization are carried out successively in aqueous medium without isolation of an intermediate.Type: GrantFiled: March 3, 1997Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Annen, Hans-Peter Seelmann-Eggebert, Rudi Widder, Reinhard Muller
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Patent number: 5756803Abstract: A process for the condensation of an aldehyde with hydrogen cyanide in the presence of a buffer is disclosed. The buffer advantageously allows the condensation reaction to occur at a pH equal to or above 4.0 and in the absence of amines.Type: GrantFiled: April 24, 1996Date of Patent: May 26, 1998Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Claude Casse, Frederic Kress, Philippe Morel
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Patent number: 5705675Abstract: Described herein is a catalytic processes for the preparation of 3-(methylthio)propanal and 2-hydroxy-4-(methylthio)butanenitrile using novel addition catalysts are disclosed. The novel addition catalysts include:triisopropanolamine, nicotinamide, imidazole, benzimidazole, 2-fluoropyridine, poly-4-vinylpyridine, 4-dimethylaminopyridine, picoline, pyrazine, trialkylamines having from three to eighteen carbon atoms in each of the alkyl substituents bonded to the nitrogen atom and tertiary amines having the formula ##STR1## wherein A is aryl, R.sub.1 and R.sub.2 are alkyl and x, a, b and c are integers such that 0.ltoreq.x.ltoreq.3, 1.ltoreq.a.ltoreq.3, 0.ltoreq.b.ltoreq.2, 0.ltoreq.c.ltoreq.2 provided that a+b+c=3.Type: GrantFiled: December 29, 1995Date of Patent: January 6, 1998Assignee: Novus International, Inc.Inventors: Thomas F. Blackburn, Paul F. Pellegrin
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Patent number: 5663409Abstract: Catalytic processes for the preparation of 3-(methylthio)propanal and 2-hydroxy-4-(methylthio)butanenitrile using novel addition catalysts are disclosed. The novel addition catalysts include: nicotinamide, imidazole, benzimidazole, 2-fluoropyridine, poly-4-vinylpyridine, 4-dimethylaminopyridine, picoline and pyrazine.Type: GrantFiled: June 7, 1995Date of Patent: September 2, 1997Assignee: Novus International, Inc.Inventors: Thomas F. Blackburn, Paul F. Pellegrin
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Patent number: 5350871Abstract: The invention relates to a method of preparing an optically active cyanohydrin by addition of hydrogen cyanide to a carbonyl compound, selected from aldehydes and ketones, in the presence of hydroxynitrile lyase, in a biphasic solvent system, comprising a homogeneous aqueous solution of said enzyme, and a suitable organic solvent which is at least substantially immiscible with water. Said method is performed in that said homogeneous aqueous solution is buffered with an acetate buffer having a buffer concentration of between 0.005 and 0.1 mole per liter or with a non-acetate buffer, that the volume ratio organic phase:aqueous phase is between approx. 5:1 and approx. 1:5, and that a solution of hydrogen cyanide and said carbonyl compound in said organic solvent is properly mixed during the reaction period with said homogeneous aqueous solution of hydroxynitrile lyase.Type: GrantFiled: December 8, 1992Date of Patent: September 27, 1994Assignee: Duphar International Research B.V.Inventors: Hendrik W. Geluk, Wybrand T. Loos
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Patent number: 5332826Abstract: This invention relates to a process for preparing aminoacetonitriles in one vessel. The process involves the steps of: (A) reacting an alkali metal cyanide with an aldehyde in water to form a cyanohydrin; (B) extracting the cyanohydrin formed in Step (A) into a water immiscible solvent to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase; (C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin; (D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution; and (E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5332825Abstract: This invention relates to two processes for preparing aminoacetonitriles in one vessel under anhydrous conditions. Process I involves the steps of: (A) reacting trimethylsilyl cyanide and an aldehyde in a water miscible amide solvent to obtain a silyl blocked cyanohydrin solution; (B) adding a catalytic amount of water to the silyl blocked cyanohydrin solution from Step (A); and (C) passing ammonia through the solution to obtain an aminoacetonitrile. Process II involves the steps of: (A') reacting trimethylsilyl cyanide with an aldehyde in the absence of solvent to form a silyl blocked cyanohydrin; (B') adding a water miscible amide solvent to the silyl blocked cyanohydrin from Step (A') to obtain a solution; and (C') passing ammonia through the solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5292918Abstract: A process for preparing an (S,S) or (R,R) diastereoisomer of the formula: ##STR1## or salts, esters or amides thereof, wherein R.sup.3 and R.sup.4 independently represent hydrogen, alkyl, aryl or aryl substituted with halogen, alkyl, nitro or alkoxy, and n and m independently represent integers from one to six, comprising combining a cyanide compound of the formula:M.sup.1 C.tbd.N (III)wherein M.sup.1 is hydrogen, trimethylsilyl or a metal, with an optional proton source, a solvent and a Lewis acid of the formula:M.sup.2 X.sub.4, AlCl.sub.3 or BF.sub.3 (IV)wherein M.sup.2 is Sn or Ti and X represents chloro, bromo, fluoro or iodo, with an .alpha.-amino acid compound or salts or esters thereof, followed by addition of an acyl or acetal compound to give the diastereoisomer of formula (X).Type: GrantFiled: October 6, 1992Date of Patent: March 8, 1994Assignee: Schering CorporationInventors: Jacques Gosteli, Ingrid Mergelsberg, Markus Tanner
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Patent number: 5235089Abstract: A process for the preparation of isophorone nitrile utilizing solutions of lithium hydroxide or lithium cyanide, solid LiOH or solid LiOH.cndot.H.sub.2 O as a catalyst. The reaction is carried out under precisely controlled temperature conditions and cyanide feed rate profiles to maintain a reasonably constant concentration of non-reacted cyanide, thereby minimizing the formation of undesirable diisophorone, its nitrile derivative(s) and HCN polymers. A polyacidic acid can be used to acidify the batch, followed by filtration to remove the precipitated lithium salt of the acid, and vacuum distillation to remove liberated HCN and excess isophorone. The resulting isophorone nitrile is obtained in high yield and with low impurity content.Type: GrantFiled: February 27, 1992Date of Patent: August 10, 1993Assignee: Hampshire Chemical Corp.Inventors: Richard P. Woodbury, Jon C. Thunberg, Steven P. VanKouwenberg, Walter B. Begonis
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Patent number: 5187296Abstract: A process for the assymetric cyanohydrination of m- phenoxybenzaldehyde with HCN, using a catalytically effective amount of enantiomeric cyclo(phenylalanylhistidine) absorbed on a solid support comprising a nonionic polymer resin is described.Type: GrantFiled: July 17, 1991Date of Patent: February 16, 1993Assignee: Bromine Compounds LimitedInventors: Yigal Becker, Asher Elgavi, Youval Shvo