Aldehyde Or Ketone, And Ammonia Or Substituted Ammonia, Reacted With The Inorganic Cyanide Patents (Class 558/346)
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Patent number: 9914693Abstract: 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: GrantFiled: February 12, 2014Date of Patent: March 13, 2018Assignee: BASF SEInventors: Hermann Luyken, Stephanie Jaegli, Michael Lorenz, Gordon Brasche, Markus Jegelka, Barbara Becker, Robert Baumann, Johann-Peter Melder, Boris Buschhaus, Thomas Krug
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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 From time to time or continuously, at least a portion of the spent washing solution is withdrawn from the gas-liquid contacting stage. The treated synthesis gas (38) is also withdrawn from the gas-liquid contacting stage.Type: GrantFiled: October 29, 2007Date of Patent: March 6, 2012Assignee: Sasol Techonology (Proprietary) LimitedInventors: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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Publication number: 20110104765Abstract: 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: ApplicationFiled: October 29, 2010Publication date: May 5, 2011Inventors: Kevin John HALLORAN, Alex COMELY, Zhengming CHEN, Shyam KRISHNAN
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Patent number: 7531683Abstract: 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: GrantFiled: May 21, 2003Date of Patent: May 12, 2009Assignee: Phoenix Chemicals LimitedInventors: Lee David Proctor, Anthony John Warr
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Patent number: 6861548Abstract: 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: GrantFiled: September 9, 2002Date of Patent: March 1, 2005Assignee: BASF AktiengesellschaftInventors: Thomas Greindl, Gerold Braun, Friedrich Wirsing, Georg Krug
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Patent number: 6624323Abstract: 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: GrantFiled: March 14, 2002Date of Patent: September 23, 2003Assignee: SmithKline Beecham CorporationInventor: Jose J. Conde
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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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Patent number: 6359162Abstract: 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: GrantFiled: February 17, 2000Date of Patent: March 19, 2002Assignee: Hoechst Schering AgrEvo GmbHInventor: Lothar Willms
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Patent number: 6284901Abstract: 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: GrantFiled: June 7, 2000Date of Patent: September 4, 2001Assignee: Dixie Chemical CompanyInventors: Joseph C. Rongione, Robert G. Brown, Dwight E. Raff
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Patent number: 5618965Abstract: 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: GrantFiled: March 4, 1996Date of Patent: April 8, 1997Assignee: CIBA-GEIGY CorporationInventor: Martin Kudschus
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Patent number: 5349079Abstract: .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: GrantFiled: October 13, 1993Date of Patent: September 20, 1994Assignee: Akzo Nobel nvInventors: Alison A. Fleming, Meiylin F. Antezzo
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Patent number: 5268498Abstract: 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: GrantFiled: December 14, 1992Date of Patent: December 7, 1993Assignee: Akzo nvInventor: Alison A. Fleming
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Patent number: 5208363Abstract: 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: GrantFiled: May 5, 1992Date of Patent: May 4, 1993Assignee: The Dow Chemical CompanyInventors: Druce K. Crump, David A. Wilson
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Patent number: 5194657Abstract: 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: GrantFiled: December 9, 1991Date of Patent: March 16, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ronald J. McKinney, Robert N. McGill
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Patent number: 5191106Abstract: 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: GrantFiled: July 30, 1992Date of Patent: March 2, 1993Assignee: W. R. Grace & Co.-Conn.Inventor: Brian A. Parker
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Patent number: 5187301Abstract: 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: GrantFiled: October 11, 1990Date of Patent: February 16, 1993Assignee: W. R. Grace & Co.-Conn.Inventors: Barry A. Cullen, Brian A. Parker
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Patent number: 5079380Abstract: 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: GrantFiled: May 23, 1990Date of Patent: January 7, 1992Assignee: W. R. Grace & Co.-Conn.Inventor: Jon C. Thunberg
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Patent number: 5008428Abstract: 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: GrantFiled: October 26, 1989Date of Patent: April 16, 1991Assignee: W. R. Grace & Co.-Conn.Inventors: Martin B. Sherwin, Jow-Lih Su
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Patent number: 4962223Abstract: 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: GrantFiled: July 3, 1989Date of Patent: October 9, 1990Assignee: Ministero dell'Universita e delle Ricerca Scientifica e TecnologicaInventors: Vincenzo Cannata, Giancarlo Tamerlani, Mauro Morotti
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Patent number: 4959390Abstract: 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: GrantFiled: December 15, 1988Date of Patent: September 25, 1990Assignee: E. I. du Pont de Nemours and CompanyInventors: Ghanshyam Patil, William L. Matier, Khuong H. X. Mai
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Patent number: 4948909Abstract: 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: GrantFiled: August 14, 1989Date of Patent: August 14, 1990Assignee: Monsanto CompanyInventors: Karl E. Koenig, Gary A. Lanser, Paul A. Morrison, Robert B. Weisenfeld
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Patent number: 4895971Abstract: 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: GrantFiled: October 31, 1988Date of Patent: January 23, 1990Assignee: W. R. Grace & Co.-Conn.Inventors: Jow-Lih Su, Martin B. Sherwin
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Patent number: 4745207Abstract: 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: GrantFiled: November 25, 1985Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Fritz Brunnmueller, Karlheinz Stecher, Michael Kroener, Rolf Schneider
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Patent number: 4731465Abstract: 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: GrantFiled: March 7, 1984Date of Patent: March 15, 1988Assignee: Monsanto CompanyInventors: Chung Y. Shen, Kent P. Lannert
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Patent number: 4704465Abstract: 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: GrantFiled: November 22, 1985Date of Patent: November 3, 1987Assignee: Monsanto CompanyInventors: Kent P. Lannert, Sum-Muk Lee
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Patent number: 4694103Abstract: 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: GrantFiled: May 19, 1986Date of Patent: September 15, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventors: Larry R. Krepski, Howell K. Smith, II, Jerald K. Rasmussen, Steven M. Heilmann
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Patent number: 4661614Abstract: 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: GrantFiled: March 6, 1986Date of Patent: April 28, 1987Assignee: Monsanto CompanyInventors: James T. Most, Thomas J. Richard