Nitrogen Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/452)
  • Patent number: 6204408
    Abstract: A process for distillative removal of 6-aminocapronitrile from mixtures (I) comprising 6-aminocapronitrile and an imine (II) comprises conducting the distillation in the presence of carbon dioxide.
    Type: Grant
    Filed: July 21, 1999
    Date of Patent: March 20, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Bassler, Hermann Luyken, Alwin Rehfinger, Harald Rust
  • Patent number: 6169199
    Abstract: A process for distillative removal of 6-aminocapronitrile from mixtures (I) comprising 6-aminocapronitrile and an imine (II) comprises performing the distillation in a distillation column using an average mean residence time for the distillation mixture of at least 5 minutes on at least one level of the distillation column.
    Type: Grant
    Filed: August 9, 1999
    Date of Patent: January 2, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Alwin Rehfinger, Hermann Luyken
  • Patent number: 6165237
    Abstract: Compounds of the general formula IZ--CH.sub.2 --NY.sub.2-n H.sub.n (I)wheren is 0 or 1,z is a straight-chain or branched polyalkyl radical having a number average molecular weight of from about 150 to 40,000, andY is a radical of the formula IIa or IIb ##STR1## where the radicals R, R.sup.1 and R.sup.2 independently of one another, are each hydrogen, an unsubstituted or substituted alkyl, alkenyl or alkynyl radical or an unsubstituted or substituted cycloalkyl, aryl or arylalkyl radical, which may carry one or more heteroatoms, andA is an alkyleneimine radical; or, ifn is 0, one of the radicals Y may be a polyoxyalkylene radical, and processes for their preparation and fuel and lubricant compositions, and mixtures of additives, which contain the novel compounds.
    Type: Grant
    Filed: August 17, 1998
    Date of Patent: December 26, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Julius, Roland Ettl, Wolfgang Gunther, Thomas Greindl
  • Patent number: 6156694
    Abstract: The present invention relates to a Raney catalyst comprising iron, cobalt, a third metal wherein the third metal is selected from the group consisting of nickel, rhodium, ruthenium, palladium, platinum, osmium, iridium and mixtures of any of the metals of this group.
    Type: Grant
    Filed: November 5, 1998
    Date of Patent: December 5, 2000
    Assignee: E. I. Dupont De Nemours & Company
    Inventor: Mark Jay Harper
  • Patent number: 6121481
    Abstract: The invention concerns a process for the preparation of 6-aminocapronitrile or 6-aminocapronitrile-hexamethylene diamine mixtures by: a) reacting 5-formylvaleronitrile with ammonia and hydrogen in the presence of hydrogenation catalysts selected from the group consisting of metals or metal compounds rhenium, copper and elements of group VIII of the periodic table of elements, a hydrogenation discharge product being obtained; and b) extracting from the hydrogenation discharge product 6-aminocapronitrile and optionally hexamethylene diamine, provided that the hydrogenation catalyst does not contain copper, nickel or copper and nickel as it's only components.
    Type: Grant
    Filed: February 1, 1999
    Date of Patent: September 19, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rocco Paciello, Michael Roper, Werner Schnurr
  • Patent number: 6114567
    Abstract: Aliphatic alpha,omega-aminonitriles are prepared by partial hydrogenation of aliphatic alpha,omega-dinitriles at elevated temperatures and superatmospheric pressure in the presence of a solvent and of a catalyst by a process which comprises using a catalyst which(a) contains a compound based on a metal selected from the group consisting of nickel, cobalt, iron, ruthenium and rhodium and(b) contains from 0.01 to 25% by weight, based on (a), of a promoter based on a metal selected from the group consisting of palladium, platinum, iridium, osmium, copper, silver, gold, chromium, molybdenum, tungsten, manganese, rhenium, zinc, cadmium, lead, aluminum, tin, phosphorus, arsenic, antimony, bismuth and rare earth metals and(c) from 0 to 5% by weight, based on (a), of a compound based on an alkali metal or on an alkaline earth metal.
    Type: Grant
    Filed: July 24, 1998
    Date of Patent: September 5, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
  • Patent number: 6087296
    Abstract: The present invention relates to a Raney catalyst comprising iron, cobalt, a third metal wherein the third metal is selected from the group consisting of nickel, rhodium, ruthenium, palladium, platinum, osmium, iridium and mixtures of any of these metals.
    Type: Grant
    Filed: November 5, 1998
    Date of Patent: July 11, 2000
    Assignee: E. I. du Pont de Nemours & Co.
    Inventor: Mark Jay Harper
  • Patent number: 6080883
    Abstract: A process for the coproduction of 6-aminocapronitrile (ACN) and hexamethylenediamine (HMD) by treatment of adiponitrile (ADN) with hydrogen in the presence of a nickel-containing catalyst at temperatures not below room temperature and elevated hydrogen partial pressure in the presence or absence of a solvent comprises, after the conversion based on ADN and/or the selectivity based on ACN has or have dropped below a defined value(a) interrupting the treatment of ADN with hydrogen by stopping the feed of ADN and of the solvent, if used,(b) treating the catalyst at from 150 to 400.degree. C. with hydrogen using a hydrogen pressure within the range from 0.1 to 30 MPa and a treatment time within the range from 2 to 48 h, and(c) then continuing the hydrogenation of ADN with the treated catalyst of stage (b).
    Type: Grant
    Filed: October 8, 1998
    Date of Patent: June 27, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Schnurr, Guido Voit, Klemens Flick, Johann-Peter Melder, Rolf Fischer, Wolfgang Harder
  • Patent number: 6077877
    Abstract: The present invention provides amine/amide catalysts for use in catalyzing the formation of polyurethane. The amine/amide catalysts, which have low fugitivity due to their reactivity with isocyanates, and good catalytic activity, have the structure ##STR1## wherein Q is C.sub.z H.sub.2z+1, or (CH.sub.2).sub.n N(R.sup.3).sub.k T, T is a monovalent C.sub.1 -C.sub.4 alkyl, amino-C.sub.1 -C.sub.4 -alkyl, mono-C.sub.1 -C.sub.4 -alkylamino-C.sub.1 -C.sub.4 -alkyl, or di-C.sub.1 -C.sub.4 -alkylamino-C.sub.1 -C.sub.4 -alkyl group, or T is a divalent alkyl, amine substituted alkyl, alkylaminoalkyl, or alkoxyalkyl group which forms with the nitrogen atom shown in structure (I) to which T is attached a cyclic structure which incorporates up to 6 carbon atoms in the ring as well as the nitrogen atom shown in structure (I), which cyclic structure may be substituted with C.sub.1 to C.sub.4 alkyl;k=0 or 1, being 1 if T is a monovalent group and 0 if T is a divalent group; R.sup.2 .dbd.H or C.sub.z H.sub.2z+1 ; R.sup.3 .dbd.
    Type: Grant
    Filed: April 3, 1997
    Date of Patent: June 20, 2000
    Assignee: CK Witco Corporation
    Inventors: Richard M. Gerkin, K. Kaye Robinson
  • Patent number: 6048997
    Abstract: Manufacture of 6-aminocapronitrile or 6-aminocapronitrile/hexamethylene diamine mixtures, involving a) the reaction of at least one pentennitrile, selected from the group consisting of 2,3 and 4-pentennitrile with carbon monoxide and hydrogen in the presence of catalysts, which contain at least one element of the eighth subgroup as active components, obtaining a hydrogenation formylating discharge (I), b) the optional separation of carbon monoxide, hydrogen and the catalyst from the hydrogenation formylating discharge (I), obtaining a hydrogenation formylating discharge (II), c) the separation of 5-formyl valeronitrile from the hydrogenation formylating discharge (I) or (II), d) the reaction of separated 5-formyl valeronitrile with ammonia and hydrogen in the presence of hydrogenating catalysts, selected from the group consisting of rhenium, copper and its compounds as well as metals and metallic compounds of the eighth group, obtaining a hydrogenation discharge, and e) obtaining 6-aminocapronitrile and if ne
    Type: Grant
    Filed: February 1, 1999
    Date of Patent: April 11, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rocco Paciello, Michael Roper, Werner Schnurr
  • Patent number: 5986126
    Abstract: Process for producing 6-aminocapronitrile and/or hexamethylenediamine by hydroformylating 3-pentenenitrile, isolating a formylvaleronitrile (FVN) mixture from the hydroformylation reaction product, reductively aminating the FVN mixture and isolating the desired product.
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: November 16, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Emilio Enrique Bunel, Theodore Augur Koch, Ronnie Ozer, Shawn Homer Phillips, Sourav Kumar Sengupta
  • Patent number: 5961788
    Abstract: A process for removing tetrahydroazepine from aminocapronitrile or hexamethylenediamine by sequential distillation in which the overhead from the second distillation is combined with a fresh, incoming mixture of tetrahydroazepine and aminocapronitrile or hexamethylenediamine.
    Type: Grant
    Filed: October 9, 1998
    Date of Patent: October 5, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: John Joseph Ostermaier
  • Patent number: 5902883
    Abstract: The present invention relates to a process for the cyanobutylation of ammonia, an alkylamine or hydrazine with 3- and 4-pentenenitrile and mixtures thereof to form alkylaminonitriles.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: May 11, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Frank Edward Herkes
  • Patent number: 5801268
    Abstract: Aliphatic alpha,omega-aminonitriles are prepared by partial hydrogenation of aliphatic alpha,omega-dinitriles at elevated temperatures and superatmospheric pressure in the presence of a solvent and of a catalyst by a process which comprises using a catalyst which(a) contains a compound based on a metal selected from the group consisting of nickel, cobalt, iron, ruthenium and rhodium and(b) contains from 0.
    Type: Grant
    Filed: April 28, 1997
    Date of Patent: September 1, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
  • Patent number: 5801267
    Abstract: Aliphatic alpha,omega-aminonitriles are prepared by partial hydrogenation of aliphatic alpha,omega-dinitriles at elevated temperatures and superatmospheric pressure in the presence of a solvent and of a catalyst by a process in which the catalyst(a) contains a compound based on a metal selected from the group consisting of nickel, cobalt, iron, ruthenium and rhodium and(b) contains from 0.
    Type: Grant
    Filed: April 28, 1997
    Date of Patent: September 1, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
  • Patent number: 5756808
    Abstract: Aliphatic alpha,omega-aminonitriles are prepared by partial hydrogenation of aliphatic alpha,omega-dinitriles at elevated temperatures and superatmospheric pressure in the presence of a solvent and of a catalyst by a process in which the catalyst(a) contains a compound based on a metal selected from the group consisting of nickel, cobalt, iron, ruthenium and rhodium and(b) contains from 0.
    Type: Grant
    Filed: May 16, 1996
    Date of Patent: May 26, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
  • Patent number: 5668277
    Abstract: One or more polyamides can be depolymerized in the presence of at least one nitrogen-containing compound. The depolymerization takes place at a pressure between about 0.5 and about 5 atm. The polyamide may be in the form of carpet waste or other heterogeneous form. Advantages include better selectivity towards the polyamide monomeric components and use of low pressure equipment to effect depolymerization.
    Type: Grant
    Filed: April 15, 1996
    Date of Patent: September 16, 1997
    Assignee: DSM N.V.
    Inventors: Jan A. J. Hendrix, Martin Booij, Yvonne H. Frentzen
  • Patent number: 5646327
    Abstract: Substituted hydroxylamines useful in photographic processing solution can be prepared by reacting a hydroxylamine with a vinylic compound having an electron withdrawing substituent in a suitable solvent, in the absence of a neutralizing base. The resulting products can be used without isolation from the reaction solution.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: July 8, 1997
    Assignee: Eastman Kodak Company
    Inventors: Elizabeth Gertrude Burns, Lynda Woedy McGarry, Gary Stephen Proehl, Lee Hamilton Latimer
  • Patent number: 5618966
    Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: April 8, 1997
    Assignee: Pharm-Eco Laboratories, Incorporated
    Inventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
  • Patent number: 5599990
    Abstract: A quaternary ammonium halide is prepared by reacting a substituted or unsubstituted haloalkane with a tert-amine in a mol ratio not higher than 1.1/1 in the absence of a solvent and at a temperature such as to maintain the reaction mixture liquid.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: February 4, 1997
    Assignee: Albemarle Corporation
    Inventors: Joseph H. Miller, Joe D. Sauer, Dru L. DeLaet
  • Patent number: 5599994
    Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.The method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 4, 1997
    Assignee: Pharm-Eco Laboratories, Inc.
    Inventors: Biman Pal, Siya Ram, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
  • Patent number: 5527946
    Abstract: Aliphatic alpha, omega-aminonitriles are prepared by partial hydrogenation of aliphatic alpha, omega-dinitriles at elevated temperatures and superatmospheric pressure in the presence of a solvent and of a catalyst by a process which comprises using a catalyst which(a) contains a compound based on a metal selected from the group consisting of nickel, cobalt, iron, ruthenium and rhodium and(b) contains from 0.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: June 18, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
  • Patent number: 5492641
    Abstract: .beta.-Aminonitriles of the following formula I ##STR1## where R.sup.1 is an aliphatic hydrocarbon radical having alkyl side groups and a number average molecular weight of from 250 to 5,000 and R.sup.2, R.sup.3 and R.sup.4, independently of one another, are each hydrogen or C.sub.1 -C.sub.8 -alkyl and R.sup.2 or R.sup.4 is also phenyl, and alkylpropylenediamines prepared from the .beta.-aminonitriles by hydrogenation are used as additives in fuels and lubricants.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: February 20, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Mohr, Knut Oppenlaender, Lothar Franz, Juergen Thomas
  • Patent number: 5493053
    Abstract: A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamin o]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, desferrioxamine B (DFO) is described. N-Benzyloxy-1,5-diaminopentane is selectively protected at the primary amino site. The product is reacted at the benzyloxyamine with an anhydride to produce a carboxylic acid which is, in turn, acylated regio-specifically with a diamine at the primary amine to give a benzyloxyamine. The previous two steps are repeated to afford a DFO reagent. Acetylation of the DFO reagent, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnishes DFO.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: February 20, 1996
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5476960
    Abstract: An .alpha.-aminonitrile compound derived from the reaction, in the presence of a cyanide source of (1) a bisulfite adduct of a carbonyl compound selected from the group consisting of an aldehyde and a ketone with (2) a fatty alkyl alkylene diamine containing two reactible amino functionalities which is of the formula RNHR.sub.1 NH.sub.2, where R is fatty alkyl and R.sub.1 is lower alkylene of up to six carbon atoms.
    Type: Grant
    Filed: April 7, 1994
    Date of Patent: December 19, 1995
    Assignee: Akzo Nobel N.V.
    Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
  • Patent number: 5475138
    Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.
    Type: Grant
    Filed: July 7, 1994
    Date of Patent: December 12, 1995
    Assignee: Pharm-Eco Laboratories Incorporated
    Inventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
  • Patent number: 5461053
    Abstract: The present invention relates to pyridazine derivatives of formula: ##STR1## which are useful as ligands of cholinergic receptors, in particular, receptors of the M.sub.1 type.
    Type: Grant
    Filed: October 22, 1992
    Date of Patent: October 24, 1995
    Assignee: Sanofi
    Inventors: Robert Boigegrain, Roger Brodin, Jean P. Kan, Dominique Olliero, Camille G. Wermuth, Jean-Jacques Bourguignon, Paul Worms
  • Patent number: 5434291
    Abstract: A process for the preparation of aminopropionitriles of the general formula I ##STR1## in which R denotes hydrogen or methyl, wherein ammonia is caused to react with an acrylonitrile of the general formula II ##STR2## In which the substituent has the aforementioned meanings, in a molar ratio of from 1:1 to 500:1 over a heterogenic catalyst at temperatures ranging from 40.degree. to 180.degree. C. and pressures ranging from 10 to 350 bar.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: July 18, 1995
    Assignee: BASF Aktiengsellschaft
    Inventors: Tom Witzel, Rudolf Kummer, Franz Merger, Guido Voit, Martin Brudermueller, Claus-Ulrich Priester, Wolfgang Harder
  • Patent number: 5399706
    Abstract: Imidazolidinone compounds of the formula: ##STR1## where R is a C.sub.3 -C.sub.5 alkylene group, R.sup.1 and R.sup.2 are independently H or C(.dbd.O)R.sup.4, R.sup.3 is an aliphatic hydrocarbon group optionally substituted with one or more alkoxy groups or interrupted by one or more ether oxygen atoms, and R.sup.4 is a hydrocarbon group substituted with an active hydrogen functional group are useful as chain extending monomers providing pendant imidazolidinone functionality to polyurethane/urea and epoxy polymers. The subject imidazolidinone compounds may also be incorporated into polyester/polyamide polyols or reacted to prepare radically polymerizable ethylenically unsaturated monomer and prepolymer compounds used in the synthesis of emulsion polymers.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: March 21, 1995
    Assignee: H. B. Fuller Licensing & Financing, Inc.
    Inventor: Michael J. Dochniak
  • Patent number: 5395974
    Abstract: The present invention relates to a method of reacting polyamides or mixtures thereof with ammonia to obtain a mixture of monomers. The reaction is carried out in the presence of certain Lewis Acid catalyst precursors.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: March 7, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ronald J. McKinney
  • Patent number: 5369104
    Abstract: Novel compound represented by the formula: ##STR1## wherein X stands for a methine (i.e. the group --CH.dbd.) group or a nitrogen atom; R.sup.1 stands for a hydrogen atom, an optionally substituted lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group, or, taken together, may form a 5- to 7-membered ring combined with the adjacent --C.dbd.C--; R.sup.4 and R.sup.5 respectively stands for a hydrogen atom or an optionally substituted lower alkyl group or, taken together, form a 3- to 7-membered homo- or heterocyclic ring combined with the adjacent carbon atom; A stands for an optionally substituted amino group; m and n denote 1 to 4, respectively, or salts thereof which has an antiallergic, antiinflammatory and anti-PAF activity and is useful as an antiasthmatic agent.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: November 29, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5367113
    Abstract: Synthesis of desferrioxamine B and analogs and homologs thereof beginning with O-protected, N-protected hydroxylamine, which is N-alkylated to produce a protected N-4-cyanoalkylhydroxylamine which is acylated with a suitable anhydride. The resulting half-acid amide is subjected to a series of high yield condensations and reductions which vide desferrioxamine B in high overall yield. Alternatively, polyether analogs of desferrioxamine B can be prepared by reacting an activated polyether with the O-protected, N-protected hydroxylamine and subjecting the resulting product to a series of similar steps.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: November 22, 1994
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5354777
    Abstract: New cyanoalkene derivatives of the formula (I) ##STR1## are described, in which R and R.sup.1 have the meaning given in the description, and a process for their preparation.The new cyanoalkene derivatives are used for combating microorganisms for the protection of industrial materials.
    Type: Grant
    Filed: February 23, 1993
    Date of Patent: October 11, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Wachtler, Wilfried Paulus, Georg-Wilhelm Ludwig
  • Patent number: 5334745
    Abstract: 3-Aminopropionitriles of the general formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4 and R.sup.5 independently of one another are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.8 -aminoalkyl, C.sub.1 -C.sub.8 -cyanoalkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.7 -C.sub.20 -aralkyl or aryl,are prepared by a process in which an amine of the general formula II ##STR2## is reacted with an acrylonitrile of the general formula III ##STR3## where the substituents have the abovementioned meanings, in a molar ratio of from 0.9:1 to 100:1 over a heterogeneous catalyst at from 40.degree. to 200.degree. C. and from 1 to 350 bar.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: August 2, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Brudermueller, Tom Witzel, Franz Merger
  • Patent number: 5332826
    Abstract: 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: Grant
    Filed: October 13, 1993
    Date of Patent: July 26, 1994
    Assignee: Eastman Kodak Company
    Inventor: Paul R. Buckland
  • Patent number: 5332825
    Abstract: 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: Grant
    Filed: October 13, 1993
    Date of Patent: July 26, 1994
    Assignee: Eastman Kodak Company
    Inventor: Paul R. Buckland
  • Patent number: 5319126
    Abstract: .alpha.-aminonitrile compounds derived from a fatty alkyl alkylene diamine containing two reactible amino functionalities are disclosed.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: June 7, 1994
    Assignee: Akzo n.v.
    Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
  • Patent number: 5302756
    Abstract: Useful monomeric products are obtained in the reaction of nylon 6,6 with ammonia. Increased yield of monomer products from nylon 6,6 is obtained from ammonolysis when a mixture with nylon 6 is employed.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: April 12, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ronald J. McKinney
  • Patent number: 5296628
    Abstract: A process for the conversion of adiponitrile to 6-aminocapronitrile in high yield and high selectivity using Raney nickel catalyst and a reaction mixture containing a low valent transition metal complex.
    Type: Grant
    Filed: February 13, 1992
    Date of Patent: March 22, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Kathryn M. Sanchez
  • Patent number: 5281361
    Abstract: Novel cationic nitriles, methods of preparing such nitriles and use thereof as cationic peroxyacid bleach precursor in bleaching (detergent) compositions are disclosed.The novel cationic nitriles are non-hygroscopic and are characterized in that they have a counter-anion X.sup.- selected from the group consisting of 1) R-SO.sub.3.sup.-, 2) R-SO.sub.4.sup.-, 3) R-CO.sub.2.sup.-, wherein R is a straight or branched chain, optionally substituted, alkyl, alkylether or alkylene group containing 4 to 20 carbon atoms, or a phenyl or alkyl phenyl group containing 6 to 20 carbon atoms, and 4) any other surfactant anion not falling under the groups 1), 2) and 3).
    Type: Grant
    Filed: May 29, 1991
    Date of Patent: January 25, 1994
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Christopher J. Adams, Stephen A. Madison, John Oakes, David W. Thornthwaite
  • Patent number: 5268499
    Abstract: A process for preparing mixtures of 3-aminopropionitrile of the formula IH.sub.2 N--CH.sub.2 --CH.sub.2 --CN (I)and ethylene cyanohydrin of the formula IIHO--CH.sub.2 --CH.sub.2 --CN (II)comprises reacting bis(2-cyanoethyl) ether of the formula IIINC--CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --CN (III)with ammonia at from 50 to 170.degree. C. and under from 1 to 500 bar thermally or in the presence of a heterogeneous catalyst.
    Type: Grant
    Filed: April 19, 1993
    Date of Patent: December 7, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Martin Brudermueller, Wolfgang Harder, Juergen Hartig, Dieter Franz
  • Patent number: 5254724
    Abstract: Synthesis of desferrioxamine B and analogs and homologs thereof beginning with O-protected, N-protected hydroxylamine, which is N-alkylated to produce a protected N-4-cyanoalkylhydroxylamine which is acylated with a suitable anhydride. The resulting half-acid amide is subjected to a series of high yield condensations and reductions which provide desferrioxamine B in high overall yield. Alternatively, polyether analogs of desferrioxamine B can be prepared by reacting an activated polyether with the O-protected, N-protected hydroxylamine and subjecting the resulting product to a series of similar steps.
    Type: Grant
    Filed: October 30, 1991
    Date of Patent: October 19, 1993
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5252747
    Abstract: Chiral compounds having the formulae ##STR1## useful in the synthesis of quinolone intermediates.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: October 12, 1993
    Assignee: Abbott Laboratories
    Inventors: Daniel T. Chu, Qun Li
  • Patent number: 5247120
    Abstract: Abstract of the Disclosure: Aminopropionitriles of the general formula I ##STR1## where R is hydrogen or methyl, wherein ammonia is reacted with an acrylonitrile of the general formula II ##STR2## where the substituents have the abovementioned meanings, in a molar ratio of from 1:1 to 500:1 over a heterogeneous catalyst at from 40.degree. to 180.degree. C. and from 10 to 350 bar.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: September 21, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Martin Brudermueller, Claus-Ulrich Priester, Wolfgang Harder, Siegfried Winderl
  • Patent number: 5237088
    Abstract: A process for transfer hydrogenation of nitriles and amines wherein the amines are the hydrogen donors is disclosed.
    Type: Grant
    Filed: March 25, 1992
    Date of Patent: August 17, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 5236616
    Abstract: Bleaching compositions are disclosed comprising a peroxide bleaching agent and a novel cationic peroxyacid bleach precursor having at least one of the following groups (A) and (B) : ##STR1## wherein R.sub.1 and R.sub.2 are each individually H, or a substituent group containing at least one carbon atom, provided that R.sub.1 and R.sub.2 are not both H.The novel bleach precursor of the cationic nitrile type shows no tendency to deliquesce under normal atmospheric conditions.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: August 17, 1993
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: John Oakes, David W. Thornthwaite
  • Patent number: 5210271
    Abstract: A method of producing diethanolamine derivatives or acid salts thereof according to the reaction scheme: ##STR1## wherein X stands for a leaving group; and R.sup.1 stands for an alkylcarbamoyl group, which provides an industrially advantageous method of preparing the subject matter useful as an antiarrhythmic agent.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: May 11, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yukio Mizuno, Miichiro Arita
  • Patent number: 5196589
    Abstract: The present invention relates to novel methods of stabilizing polymers of acrylonitrile. The polymers are stabilized by the inclusion of small amounts of stable free radicals compounds which act to inhibit the homopolymerization of the acrylonitrile while promoting the reaction of the acrylonitrile with nucleophilic species such as amines and alcohols.
    Type: Grant
    Filed: September 16, 1991
    Date of Patent: March 23, 1993
    Assignee: LCE Partnership
    Inventors: Anthony J. O'Lenick, Jr., J. Michael Clumpner
  • Patent number: 5196583
    Abstract: The invention provides a novel class of propargyl compounds represented by the formula: ##STR1## wherein R is an C.sub.1 -C.sub.20 alkyl group, C.sub.1 -C.sub.20 alkylene group, C.sub.1 -C.sub.20 alkylene group interrupted by --NH-- group(s), C.sub.6 -C.sub.7 alicyclic group and an aromatic group; R.sub.1 comprises 1-100% --CH.sub.2 --C.tbd.CH group and 99-0% hydrogen atom and n is an integer of 1 to 4, and preparation thereof.These compounds are useful as coating material or sealer or rim-injection molding material.
    Type: Grant
    Filed: December 4, 1990
    Date of Patent: March 23, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki
  • Patent number: 5192399
    Abstract: Separation of an aliphatic aminonitrile or an aliphatic diamine from a mixture containing the corresponding cyclic, aliphatic, mono-unsaturated amine by adding caustic compound to the mixture and then distilling the aminonitrile or the diamine at a temperature less than 170.degree. C. and at a pressure of less than 1 atmosphere.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: March 9, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: James B. Sieja