Aldehyde Or Ketone, And Ammonia Or Substituted Ammonia, Reacted With The Inorganic Cyanide Patents (Class 558/346)
  • Patent number: 9914693
    Abstract: The present invention relates to a process for preparing ethylenediamine (EDA), where the process comprises the steps a) to c). In step a), formaldehyde is reacted with hydrocyanic acid (HCN) to form formaldehyde cyanohydrin (FACH), where the hydrocyanic acid is completely free or largely free of sulfur dioxide (SO2). The FACH prepared in this way is reacted with ammonia (NH3) to form aminoacetonitrile (AAN) in step b), whereupon a hydrogenation of AAN in the presence of a catalyst to form EDA is carried out in step c).
    Type: Grant
    Filed: February 12, 2014
    Date of Patent: March 13, 2018
    Assignee: BASF SE
    Inventors: Hermann Luyken, Stephanie Jaegli, Michael Lorenz, Gordon Brasche, Markus Jegelka, Barbara Becker, Robert Baumann, Johann-Peter Melder, Boris Buschhaus, Thomas Krug
  • Patent number: 8128898
    Abstract: 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 From time to time or continuously, at least a portion of the spent washing solution is withdrawn from the gas-liquid contacting stage. The treated synthesis gas (38) is also withdrawn from the gas-liquid contacting stage.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: Grant
    Filed: October 29, 2007
    Date of Patent: March 6, 2012
    Assignee: Sasol Techonology (Proprietary) Limited
    Inventors: Braam Van Dyk, John Marriott, Bavanethan Pillay, Hendrik Johannes Van Der Westhuizen, Ronél Combrink, Trevor David Phillips, Denise Louisette Venter, André´ Peter Steynberg
  • Publication number: 20110104765
    Abstract: Provided herein are compositions including diastereomers in substantially diastereomerically pure form and enantiomers in substantially enantiomerically pure form, and processes for preparing them and converting them to metyrosine.
    Type: Application
    Filed: October 29, 2010
    Publication date: May 5, 2011
    Inventors: Kevin John HALLORAN, Alex COMELY, Zhengming CHEN, Shyam KRISHNAN
  • Patent number: 7531683
    Abstract: The present invention relates to a continuous process for the cyanation of hydrogenated ?-ketoesters in a cyanation zone maintained under conditions of temperature and pressure effective for cyanation of a hydrogenated R-ketoester. A substrate comprising a hydrogenated ?-ketoester is continuously supplyed to the cyanation zone together with a cyanide. The substrate is contacted with the cyanide in the cyanation zone for a period effective for at least partial cyanation of the hydrogenated ?-ketoester and a product stream is continuously extracted from the cyanation zone.
    Type: Grant
    Filed: May 21, 2003
    Date of Patent: May 12, 2009
    Assignee: Phoenix Chemicals Limited
    Inventors: Lee David Proctor, Anthony John Warr
  • Patent number: 6861548
    Abstract: 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: Grant
    Filed: September 9, 2002
    Date of Patent: March 1, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Greindl, Gerold Braun, Friedrich Wirsing, Georg Krug
  • Patent number: 6624323
    Abstract: Herein is provided a process for preparing substituted cyclohexanoic acids of formula (I), where Ra is a carbon-containing group optionally linked by oxygen, sulfur or nitrogen to the phenyl ring and j is 1-5; and one of R and R* is hydrogen and the other is C(O)OH.
    Type: Grant
    Filed: March 14, 2002
    Date of Patent: September 23, 2003
    Assignee: SmithKline Beecham Corporation
    Inventor: Jose J. Conde
  • Patent number: 6417385
    Abstract: 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: Grant
    Filed: December 28, 2001
    Date of Patent: July 9, 2002
    Assignee: Degussa AG
    Inventors: Walter Börner, Liane Deusser, Ralph Marquardt, Rudolf Vanheertum, Karl-Heinz Vieweg
  • Patent number: 6359162
    Abstract: Glufosinate and the 2-methyl analog thereof can be prepared in a multi-step synthesis from methylphosphorus compounds (II) with unsaturated keto compounds (III) via adducts (IV), subsequent reaction under the conditions of a Strecker synthesis and finally hydrolysis of the aminonitrile (V): Step 1: Step 2: Step 3: Hydrolysis of (V) to give glufosinate Depending on process conditions and substrates, various compounds can be identified as adducts (IV).
    Type: Grant
    Filed: February 17, 2000
    Date of Patent: March 19, 2002
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventor: Lothar Willms
  • Patent number: 6284901
    Abstract: Omapatrilat (I) is a potent inhibitor of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) both in vitro and in vivo and is currently undergoing large scale clinical trials as an anti-hypertensive. Omapatrilat may be synthesized using the S-stereoisomer of a racemic mixture. The racemic mixture may be prepared from a hydantoin (III). The hydantoin may be prepared from a novel dinitrile compound (IV): The dinitrile may be produced by reacting a monoacetal with a non-carbonate ammonium salt and an alkali cyanide.
    Type: Grant
    Filed: June 7, 2000
    Date of Patent: September 4, 2001
    Assignee: Dixie Chemical Company
    Inventors: Joseph C. Rongione, Robert G. Brown, Dwight E. Raff
  • Patent number: 5618965
    Abstract: Process for preparing a nitrile of the formula (I) ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are for example hydrogen, halogen, cyano, hydroxyl, carboxyl, alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, aryl, aryloxy, arylthio or arylamino, or R.sub.2 and R.sub.3 together form a substituted or unsubstituted 4-membered carbon bridge,by reacting an aldehyde of the formula (II) ##STR2## with a hydroxylammonium salt followed by dehydration by heating to an elevated temperature, wherein the reaction takes place in the presence of an anhydrous inorganic sulfate and in the absence of diluents from the group consisting of carboxylic acids, strongly polar aprotic solvents, sulfur compounds and heteroaromatic basic nitrogen compounds.The nitriles obtainable by the process of the invention are valuable intermediates for, in particular, the preparation of diketopyrrolopyrrole pigments.
    Type: Grant
    Filed: March 4, 1996
    Date of Patent: April 8, 1997
    Assignee: CIBA-GEIGY Corporation
    Inventor: Martin Kudschus
  • Patent number: 5349079
    Abstract: .alpha.-aminonitrile compounds can be synthesized by reacting a carbonyl compound, for example an aldehyde, such as, one containing an alkyl group, with a fatty amine hydrohalide, for example, a fatty amine hydrochloride, in the presence of a cyanide source, for example, an alkali metal cyanide.
    Type: Grant
    Filed: October 13, 1993
    Date of Patent: September 20, 1994
    Assignee: Akzo Nobel nv
    Inventors: Alison A. Fleming, Meiylin F. Antezzo
  • Patent number: 5268498
    Abstract: The bisulfite adduct of a carbonyl compound, amine, and alkali metal cyanide are reacted in aqueous media to form an organic layer containing the desired .alpha.-aminonitrile product and an aqueous layer containing alkali metal sulfite. The aqueous layer, after separation from the organic layer, can be used as the reaction medium in a fresh reaction of bisulfite adduct, amine and alkali metal cyanide after its pH has been adjusted to the moderately acidic range, e.g., a pH of about 4 to about 5.
    Type: Grant
    Filed: December 14, 1992
    Date of Patent: December 7, 1993
    Assignee: Akzo nv
    Inventor: Alison A. Fleming
  • Patent number: 5208363
    Abstract: The present invention is a process for preparing aminoacetonitriles or ethylenediamine tetraacetonitrile comprising the steps of (a) admixing glycolonitrile with an amine having at least one primary amine group or ethylenediamine to form an intermediate amine acetonitrile reaction product, (b) admixing the reaction product of Step (a) with formaldehyde and hydrocyanic acid such that each hydrogen on an amine nitrogen is replaced by an acetonitrile group. The resulting aminoacetonitrile advantageously has all amino groups fully substituted with acetonitrile groups.
    Type: Grant
    Filed: May 5, 1992
    Date of Patent: May 4, 1993
    Assignee: The Dow Chemical Company
    Inventors: Druce K. Crump, David A. Wilson
  • Patent number: 5194657
    Abstract: A process for preparing an alpha aminonitrile comprises providing a cyclic or acyclic aliphatic ketone in a reactor, adding ammonia to the reactor, mixing the ketone and the ammonia, and adding hydrogen cyanide to the reactor to convert the hydrogen cyanide to an aminonitrile. Preferably, the reactor is purged with ammonia before the addition of hydrogen cyanide. The hydrogen cyanide may be added to the reactor at a constant rate, or it may be added to the reactor at a rate that decreases over time. A portion of the ketone may be added to the reactor during the addition of the hydrogen cyanide to the reactor.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: March 16, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ronald J. McKinney, Robert N. McGill
  • Patent number: 5191106
    Abstract: A novel intermediate useful in the synthesis of ethylenediaminetriacetic acid (ED3A) or its salts. A salt of N,N'-ethylenediaminediacetic acid (ED2AH.sub.2) is condensed with formaldehyde to form a stable 5-membered ring intermediate. The addition of cyanide across this cyclic material forms ethylenediamine N,N'-diacetic acid-N'-cyanomethyl or salts thereof (mononitrile-diacid), which is a useful intermediate in the production of ED3A. The nitrile in aqueous solutions may be spontaneously cyclized to form 2-oxo-1,4-piperazinediacetic acid (3KP) or salts thereof. In the presence of excess base, salts of ED3A are formed in excellent yield and purity.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: March 2, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Brian A. Parker
  • Patent number: 5187301
    Abstract: A process for producing iminodiacetonitrile (IDAN) from glycolonitrile and ammonia or its salt is disclosed. In the batch process, pH is controlled with the addition of ammonia or suitable acids. In the continuous process, glycolonitrile and ammonia are reacted in near stoichiometric amounts at a temperature from about 90.degree. C. to about 180.degree. C.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: February 16, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Barry A. Cullen, Brian A. Parker
  • Patent number: 5079380
    Abstract: A process for producing glycinonitrile under substantially adiabatic reaction conditions by reacting in a tubular reactor hydrogen cyanide, formaldehyde and ammonia. The excess ammonia is flashed off and the remaining solution volatiles are evaporated and condensed to product. The resulting glycinonitrile can be saponified to the alkali metal glycinate, from which glycine can be prepared.
    Type: Grant
    Filed: May 23, 1990
    Date of Patent: January 7, 1992
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Jon C. Thunberg
  • Patent number: 5008428
    Abstract: This invention relates to the production of aminoacetonitriles, and more specifically to an integrated process wherein a crude, unpurified reactor product stream from a hydrogen cyanide reactor together with a formaldehyde stream, optionally, a crude, unpurified reactor product stream from a formaldehyde process reactor are fed directly to a reactive absorber with an additional nitrogen source and scrubbed with a controlled pH aqueous solution to produce aminoacetonitriles in high yields. This process eliminates intermediate recovery and purification processes associated with conventional hydrogen cyanide and formaldehyde production processes by integrating the recovery and reaction processes into a reactive absorber.
    Type: Grant
    Filed: October 26, 1989
    Date of Patent: April 16, 1991
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Martin B. Sherwin, Jow-Lih Su
  • Patent number: 4962223
    Abstract: New process for the synthesis of the levodopa, L-(-)-2-amino-3-(3,4-dihydyphenyl)propionic acid, drug used in the treatment of the Parkinson's disease. The process consists in resolving with d-camphorsulfonic acid, or with a salt thereof, the d,l-2-amino-3-(3,4-dimethoxyphenyl)propionitrile, obtained from the 3,4-dimethoxyphenylacetaldehyde, and in the subsequent hydrolysis and demethylation, by means of concentrated solutions of haloid acids, of the d-2-amino-3-(3,4-dimethoxyphenyl)propionitrile and of salts thereof.
    Type: Grant
    Filed: July 3, 1989
    Date of Patent: October 9, 1990
    Assignee: Ministero dell'Universita e delle Ricerca Scientifica e Tecnologica
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Mauro Morotti
  • Patent number: 4959390
    Abstract: Compounds of the present invention, are represented by the general formula ##STR1## wherein R.sub.1 group which may be alkyl of from 1 to about 6 carbon atoms, alkenyl of from 2 to about 6 carbon atoms, alkynyl of from 2 to about 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to about 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to about 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms R.sub.2, R.sub.3 and R.sub.4 are hydrogen or hydroxyl groups or the combination of either hydrogen or hydroxyl groups; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NHCOR.sub.5, --NHCONR.sub.5 R.sub.6, or --NHCOOR.sub.5 wherein R.sub.5 and R.sub.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: September 25, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ghanshyam Patil, William L. Matier, Khuong H. X. Mai
  • Patent number: 4948909
    Abstract: An improved process is provided for producing iminodiacetonitrile by contacting ammonia, formaldehyde and hydrogen cyanide, or hexamethylenetetramine, formaldehyde and hydrogen cyanide in a reaction medium, the improvement which comprises the further steps of thereafter adjusting the pH of the reaction medium to a pH between about 5.5 and about pH 10 and heating the reaction medium to an elevated temperature for a sufficient time to convert by-products in the reaction medium to iminodiacetonitrile.
    Type: Grant
    Filed: August 14, 1989
    Date of Patent: August 14, 1990
    Assignee: Monsanto Company
    Inventors: Karl E. Koenig, Gary A. Lanser, Paul A. Morrison, Robert B. Weisenfeld
  • Patent number: 4895971
    Abstract: This invention relates to the production of iminodiacetonitrile, and more specifically to an integrated process wherein a crude, unpurified reactor gas stream from a hydrogen cyanide reactor and optionally, a crude, unpurified reactor gas stream from a formaldehyde process reactor are fed directly to a reactive absorber together with additional ammonia and acidified water to produce iminodiacetonitrile in high yields. This process provides improved economics for producing iminodiacetonitrile by eliminating costly intermediate recovery and purification processes associated with conventional hydrogen cyanide and formaldehyde production processes.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: January 23, 1990
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Jow-Lih Su, Martin B. Sherwin
  • Patent number: 4745207
    Abstract: Reaction products of hydrogen cyanide are prepared by a process in which hydrogen cyanide prepared in a conventional manner by pyrolysis at from 250.degree. to 650.degree. C. over a solid under from 5 to 200 mbar is cooled to a temperature of from 200.degree. to -10.degree. C. together with the other pyrolysis products, the hydrogen cyanide is then fed to a chemisorption reaction with a base or with a carbonyl compound, and the reaction products of hydrogen cyanide which are formed therein are removed from the system and brought to atmospheric pressure. In this process, the handling of large amounts of hydrogen cyanide is avoided.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz Brunnmueller, Karlheinz Stecher, Michael Kroener, Rolf Schneider
  • Patent number: 4731465
    Abstract: A continuous process for preparing nitrilotriacetonitrile in which the reactants, formaldehyde, hydrogen cyanide, and either ammonia or hexamethylenetetramine are reacted first in a mixing reactor, preferably a circulating loop reactor at from about 90.degree. C. to about 120.degree. C., then reacted in a plug flow tubular reactor at from about 95.degree. C. to about 120.degree. C., then after cooling the reaction mixture crystalline nitrilotriacetonitrile is recovered.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: March 15, 1988
    Assignee: Monsanto Company
    Inventors: Chung Y. Shen, Kent P. Lannert
  • Patent number: 4704465
    Abstract: A process for preparing an ethylenediamine intermediate for the production of an ethylenediaminetetraacetonitrile. Formaldehyde is combined with ethylenediamine at a mole ratio of 1 to 2 respectively wherein the molar ratio of ethylenediamine to formaldehyde in the reaction mixture at least 0.48 or greater.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: November 3, 1987
    Assignee: Monsanto Company
    Inventors: Kent P. Lannert, Sum-Muk Lee
  • Patent number: 4694103
    Abstract: A novel, one-pot procedure for the preparation of N-acryloyl-.alpha.-amino acids involves the steps of:(i) reacting a ketone, an ammonium salt, and a cyanide salt in water, optionally in the presence of ammonium hydroxide and a co-solvent, to form an aminonitrile;(ii) acryloylating the aminonitrile in aqueous media to afford an acrylamidonitrile; and(iii) hydrolyzing with aqueous acid the acrylamidonitrile to provide the N-acryloyl-.alpha.-amino acid.
    Type: Grant
    Filed: May 19, 1986
    Date of Patent: September 15, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Larry R. Krepski, Howell K. Smith, II, Jerald K. Rasmussen, Steven M. Heilmann
  • Patent number: 4661614
    Abstract: A process for preparing iminodiacetonitrile which comprises bringing together under reaction conditions formaldehyde, hydrogen cyanide and a source of ammonia under substantially stoichiometric conditions at a temperature between about 30.degree. and about 65.degree. C. at a pH between about 1.5 and about 5.5, preferably between about 3.5 and about 5.3, to produce the desired iminodiacetonitrile.
    Type: Grant
    Filed: March 6, 1986
    Date of Patent: April 28, 1987
    Assignee: Monsanto Company
    Inventors: James T. Most, Thomas J. Richard