Nitrogen Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/452)
- The chain contains nitrogen (e.g., iminodiacetonitrile, nitrilotriacetonitrile, etc.) (Class 558/455)
- Purification or recovery of saturated hydrocarbon dinitriles (e.g., from mixtures with cyanocyclopentanonimine, 2-cyanocyclopenten-1-ylamine, etc.) (Class 558/456)
- A carbon in the chain is multiple bonded to carbon (e.g., 1,4 dicyanobutene, etc.) (Class 558/457)
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Patent number: 6204408Abstract: 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: GrantFiled: July 21, 1999Date of Patent: March 20, 2001Assignee: BASF AktiengesellschaftInventors: Peter Bassler, Hermann Luyken, Alwin Rehfinger, Harald Rust
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Patent number: 6169199Abstract: 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: GrantFiled: August 9, 1999Date of Patent: January 2, 2001Assignee: BASF AktiengesellschaftInventors: Alwin Rehfinger, Hermann Luyken
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Patent number: 6165237Abstract: 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: GrantFiled: August 17, 1998Date of Patent: December 26, 2000Assignee: BASF AktiengesellschaftInventors: Manfred Julius, Roland Ettl, Wolfgang Gunther, Thomas Greindl
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Patent number: 6156694Abstract: 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: GrantFiled: November 5, 1998Date of Patent: December 5, 2000Assignee: E. I. Dupont De Nemours & CompanyInventor: Mark Jay Harper
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Patent number: 6121481Abstract: 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: GrantFiled: February 1, 1999Date of Patent: September 19, 2000Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rocco Paciello, Michael Roper, Werner Schnurr
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Patent number: 6114567Abstract: 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: GrantFiled: July 24, 1998Date of Patent: September 5, 2000Assignee: BASF AktiengesellschaftInventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
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Patent number: 6087296Abstract: 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: GrantFiled: November 5, 1998Date of Patent: July 11, 2000Assignee: E. I. du Pont de Nemours & Co.Inventor: Mark Jay Harper
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Patent number: 6080883Abstract: 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: GrantFiled: October 8, 1998Date of Patent: June 27, 2000Assignee: BASF AktiengesellschaftInventors: Werner Schnurr, Guido Voit, Klemens Flick, Johann-Peter Melder, Rolf Fischer, Wolfgang Harder
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Patent number: 6077877Abstract: 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: GrantFiled: April 3, 1997Date of Patent: June 20, 2000Assignee: CK Witco CorporationInventors: Richard M. Gerkin, K. Kaye Robinson
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Patent number: 6048997Abstract: 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 neType: GrantFiled: February 1, 1999Date of Patent: April 11, 2000Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rocco Paciello, Michael Roper, Werner Schnurr
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Patent number: 5986126Abstract: 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: GrantFiled: January 25, 1999Date of Patent: November 16, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio Enrique Bunel, Theodore Augur Koch, Ronnie Ozer, Shawn Homer Phillips, Sourav Kumar Sengupta
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Patent number: 5961788Abstract: 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: GrantFiled: October 9, 1998Date of Patent: October 5, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: John Joseph Ostermaier
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Patent number: 5902883Abstract: 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: GrantFiled: December 18, 1997Date of Patent: May 11, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: Frank Edward Herkes
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Patent number: 5801268Abstract: 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: GrantFiled: April 28, 1997Date of Patent: September 1, 1998Assignee: BASF AktiengesellschaftInventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
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Patent number: 5801267Abstract: 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: GrantFiled: April 28, 1997Date of Patent: September 1, 1998Assignee: BASF AktiengesellschaftInventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
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Patent number: 5756808Abstract: 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: GrantFiled: May 16, 1996Date of Patent: May 26, 1998Assignee: BASF AktiengesellschaftInventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
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Patent number: 5668277Abstract: 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: GrantFiled: April 15, 1996Date of Patent: September 16, 1997Assignee: DSM N.V.Inventors: Jan A. J. Hendrix, Martin Booij, Yvonne H. Frentzen
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Patent number: 5646327Abstract: 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: GrantFiled: December 8, 1995Date of Patent: July 8, 1997Assignee: Eastman Kodak CompanyInventors: Elizabeth Gertrude Burns, Lynda Woedy McGarry, Gary Stephen Proehl, Lee Hamilton Latimer
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Patent number: 5618966Abstract: 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: GrantFiled: May 16, 1995Date of Patent: April 8, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5599990Abstract: 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: GrantFiled: October 27, 1995Date of Patent: February 4, 1997Assignee: Albemarle CorporationInventors: Joseph H. Miller, Joe D. Sauer, Dru L. DeLaet
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Patent number: 5599994Abstract: 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: GrantFiled: June 7, 1995Date of Patent: February 4, 1997Assignee: Pharm-Eco Laboratories, Inc.Inventors: Biman Pal, Siya Ram, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5527946Abstract: 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: GrantFiled: January 18, 1995Date of Patent: June 18, 1996Assignee: BASF AktiengesellschaftInventors: Klemens Flick, Johann-Peter Melder, Werner Schnurr, Klaus Ebel, Tom Witzel, Wolfgang Harder, Alwin Rehfinger, Rolf Fischer
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Patent number: 5492641Abstract: .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: GrantFiled: November 21, 1994Date of Patent: February 20, 1996Assignee: BASF AktiengesellschaftInventors: Juergen Mohr, Knut Oppenlaender, Lothar Franz, Juergen Thomas
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Patent number: 5493053Abstract: 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: GrantFiled: December 21, 1994Date of Patent: February 20, 1996Assignee: University of Florida Research Foundation, Inc.Inventor: Raymond J. Bergeron, Jr.
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Patent number: 5476960Abstract: 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: GrantFiled: April 7, 1994Date of Patent: December 19, 1995Assignee: Akzo Nobel N.V.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5475138Abstract: 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: GrantFiled: July 7, 1994Date of Patent: December 12, 1995Assignee: Pharm-Eco Laboratories IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5461053Abstract: 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: GrantFiled: October 22, 1992Date of Patent: October 24, 1995Assignee: SanofiInventors: Robert Boigegrain, Roger Brodin, Jean P. Kan, Dominique Olliero, Camille G. Wermuth, Jean-Jacques Bourguignon, Paul Worms
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Patent number: 5434291Abstract: 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: GrantFiled: June 1, 1994Date of Patent: July 18, 1995Assignee: BASF AktiengsellschaftInventors: Tom Witzel, Rudolf Kummer, Franz Merger, Guido Voit, Martin Brudermueller, Claus-Ulrich Priester, Wolfgang Harder
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Patent number: 5399706Abstract: 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: GrantFiled: March 2, 1993Date of Patent: March 21, 1995Assignee: H. B. Fuller Licensing & Financing, Inc.Inventor: Michael J. Dochniak
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Patent number: 5395974Abstract: 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: GrantFiled: January 21, 1994Date of Patent: March 7, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 5369104Abstract: 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: GrantFiled: December 28, 1992Date of Patent: November 29, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
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Patent number: 5367113Abstract: 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: GrantFiled: June 23, 1993Date of Patent: November 22, 1994Assignee: University of Florida Research Foundation, Inc.Inventor: Raymond J. Bergeron, Jr.
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Patent number: 5354777Abstract: 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: GrantFiled: February 23, 1993Date of Patent: October 11, 1994Assignee: Bayer AktiengesellschaftInventors: Peter Wachtler, Wilfried Paulus, Georg-Wilhelm Ludwig
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Patent number: 5334745Abstract: 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: GrantFiled: May 28, 1993Date of Patent: August 2, 1994Assignee: BASF AktiengesellschaftInventors: Martin Brudermueller, Tom Witzel, Franz Merger
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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: 5319126Abstract: .alpha.-aminonitrile compounds derived from a fatty alkyl alkylene diamine containing two reactible amino functionalities are disclosed.Type: GrantFiled: January 29, 1993Date of Patent: June 7, 1994Assignee: Akzo n.v.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5302756Abstract: 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: GrantFiled: December 23, 1992Date of Patent: April 12, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 5296628Abstract: 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: GrantFiled: February 13, 1992Date of Patent: March 22, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Kathryn M. Sanchez
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Patent number: 5281361Abstract: 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: GrantFiled: May 29, 1991Date of Patent: January 25, 1994Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Christopher J. Adams, Stephen A. Madison, John Oakes, David W. Thornthwaite
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Patent number: 5268499Abstract: 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: GrantFiled: April 19, 1993Date of Patent: December 7, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Martin Brudermueller, Wolfgang Harder, Juergen Hartig, Dieter Franz
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Patent number: 5254724Abstract: 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: GrantFiled: October 30, 1991Date of Patent: October 19, 1993Assignee: University of Florida Research Foundation, Inc.Inventor: Raymond J. Bergeron, Jr.
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Patent number: 5252747Abstract: Chiral compounds having the formulae ##STR1## useful in the synthesis of quinolone intermediates.Type: GrantFiled: September 11, 1992Date of Patent: October 12, 1993Assignee: Abbott LaboratoriesInventors: Daniel T. Chu, Qun Li
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Patent number: 5247120Abstract: 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: GrantFiled: July 30, 1992Date of Patent: September 21, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Martin Brudermueller, Claus-Ulrich Priester, Wolfgang Harder, Siegfried Winderl
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Patent number: 5237088Abstract: A process for transfer hydrogenation of nitriles and amines wherein the amines are the hydrogen donors is disclosed.Type: GrantFiled: March 25, 1992Date of Patent: August 17, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank J. Weigert
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Patent number: 5236616Abstract: 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: GrantFiled: May 24, 1991Date of Patent: August 17, 1993Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: John Oakes, David W. Thornthwaite
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Patent number: 5210271Abstract: 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: GrantFiled: August 23, 1991Date of Patent: May 11, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Yukio Mizuno, Miichiro Arita
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Patent number: 5196589Abstract: 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: GrantFiled: September 16, 1991Date of Patent: March 23, 1993Assignee: LCE PartnershipInventors: Anthony J. O'Lenick, Jr., J. Michael Clumpner
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Patent number: 5196583Abstract: 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: GrantFiled: December 4, 1990Date of Patent: March 23, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki
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Patent number: 5192399Abstract: 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: GrantFiled: September 10, 1991Date of Patent: March 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: James B. Sieja