Of Aldehyde Or Ketone Containing Compound Patents (Class 564/471)
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Patent number: 5756558Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, a cell stabilizer and a catalyst composition comprising a compound having the following formula I: ##STR1## where R.sup.1 is hydrogen or a linear or branched C1-C4 alkyl or a C1-C4 hydroxyalkyl group;R.sup.2 and R.sup.3 independently are hydrogen, hydroxy, a linear or branched C1-C4 alkyl or a linear or branched C1-C4 hydroxyalkyl group; andR.sup.4 is a linear or branched C1-C10 hydroxyalkyl group.Type: GrantFiled: July 3, 1996Date of Patent: May 26, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Ann Coates Lescher Savoca, Richard Paul Underwood, Richard Van Court Carr, James Stephen Emerick
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Patent number: 5739403Abstract: 4-Aminodiphenylamines are produced by reacting optionally substituted aniline with optionally substituted nitrobenzene in the presence of water and/or alcohols and organic and/or inorganic bases and then catalytically hydrogenating the resultant nitro- and/or nitrosodiphenylamine in the presence of water, wherein the catalytic hydrogenation of the reaction mixture is performed in the presence of 25 to 80 wt. % of water, relative to the weight of the reaction mixture from the condensation reaction, the hydrogenation catalyst is removed from the hydrogenation mixture once absorption of hydrogen has ceased, 10 to 100 vol. % of aromatic solvent, relative to the total volume of the hydrogenation mixture, are optionally added to the hydrogenation mixture, the resultant organic phase is separated in order to isolate the 4-aminodiphenylamine and the aqueous phase is returned to the initial reaction mixture.Type: GrantFiled: January 6, 1997Date of Patent: April 14, 1998Assignee: Bayer AGInventors: Klaus Reinartz, Adolf Brill, Fred Schuhmacher
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Patent number: 5646235Abstract: A method is provided for the preparation of tertiary polyamines by alkylating a polyamine having at least two primary amino groups without the use of excess solvent. More particularly, a tertiary amine is produced by reductively alkylating a polyamine with a carbonyl compound, such as formaldehyde, in a reaction zone while in the presence of a hydrogenation catalyst and hydrogen under reductive conditions. The carbonyl compound is continuously supplied to the reaction zone.Type: GrantFiled: June 18, 1996Date of Patent: July 8, 1997Assignee: Huntsman Petrochemical CorporationInventors: Robert LeRoy Zimmerman, Wheeler Conrad Crawford, Rodney Frederick Lloyd
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Patent number: 5631405Abstract: 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: June 7, 1995Date of Patent: May 20, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5498707Abstract: A composition adapted to convert hydrogen sulfide and organic sulfides to nontoxic polymers. The compositions comprise amine resin solutions made by reacting sterically hindered amines such as selected diamines, triamines, amino alcohols, and mixtures thereof, with aldehydes, aldehyde donors, or the reaction products of lower alkanolamines and lower aldehydes. The subject compositions are preferably made by reacting the sterically hindered amines and aldehyde components in about a 1:1 molar ratio at a temperature ranging from about 110.degree. to about 120.degree. F. (about 43.degree. to about 49.degree. C.), using enough of the sterically hindered amine to produce a reaction product having a pH ranging from about 10.5 to about 12. Streams containing hydrogen sulfide or organic sulfides are preferably treated by contacting such streams with from about 2 to about 4 ppm of the amine solution of the invention per ppm of sulfide.Type: GrantFiled: May 6, 1994Date of Patent: March 12, 1996Inventor: Larry W. Gatlin
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Patent number: 5488103Abstract: A composition adapted to convert hydrogen sulfide and organic sulfides to nontoxic polymers. The compositions comprise amine resin solutions made by reacting sterically hindered amines such as selected diamines, triamines, amino alcohols, and mixtures thereof, with aldehydes, aldehyde donors, or the reaction products of lower alkanolamines and lower aldehydes. The subject compositions are preferably made by reacting the sterically hindered amines and aldehyde components in about a 1:1 molar ratio at a temperature ranging from about 110.degree. to about 120.degree. F. (about 43.degree. to about 49.degree. C.), using enough of the sterically hindered amine to produce a reaction product having a pH ranging from about 10.5 to about 12. Streams containing hydrogen sulfide or organic sulfides are preferably treated by contacting such streams with from about 2 to about 4 ppm of the amine solution of the invention per ppm of sulfide.Type: GrantFiled: May 15, 1995Date of Patent: January 30, 1996Inventor: Larry W. Gatlin
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Patent number: 5486605Abstract: A composition is disclosed that is adapted to convert hydrogen sulfide and organic sulfides to nontoxic polymers. The compositions comprise amine resin solutions made by reacting sterically hindered amines such as amine heads with aldoses selected from the group consisting of D-aldoses having from 3 to 6 carbon atoms. Streams containing hydrogen sulfide or organic sulfides are preferably treated by contacting such streams with from about 2 to about 4 ppm or more of the amine solution of the invention per ppm of sulfide.Type: GrantFiled: May 20, 1994Date of Patent: January 23, 1996Inventor: Larry W. Gatlin
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Patent number: 5457233Abstract: A process for the preparation of amines of formula ##STR1## wherein the variables are defined as in the claims, which comprises reacting 1 molar equivalent of an amine of formula ##STR2## with 0.8 to 1.5 molar equivalents of an aldehyde of formulaR--CHO (3)and 0.8 to 2 molar equivalents of formic acid, in aqueous medium, and adjusting the pH by addition of a mineral acid such that, at the conclusion of the reaction, the pH is in the range from 3 to 7. The compounds obtainable by the process are useful intermediates for the synthesis of dyeing assistants.Type: GrantFiled: November 28, 1994Date of Patent: October 10, 1995Assignee: Ciba-Geigy CorporationInventor: Philippe Ouziel
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Patent number: 5444099Abstract: A tertiary aminoalcohol having a tert-amino group(s) in the main chain and hydroxyl groups at the terminals. The use of this compound for purposes different from that of ordinary amines and amine derivatives is expected.A process for producing the tertiary aminoalcohol wherein a catalyst comprising copper, a transition metal element of the fourth period and a platinum group element of the group VIII, and further optionally containing an alkali metal or an alkaline earth metal is used.A process for producing polyurethane using the above-mentioned tertiary aminoalcohol which can solve the problems occurring in the production of a polyurethane using a tertiary amine which has a strong irritating odor and is highly irritant to the skin as a catalyst, for example, deteriorations of working atmosphere and sales appeal of the polyurethane.Type: GrantFiled: September 20, 1993Date of Patent: August 22, 1995Assignee: Kao CorporationInventors: Hiroshi Abe, Tetsuaki Fukushima, Kohshiro Sotoya, Shoichiro Harada, Hiroshi Kitagawa, Masayoshi Morii, Yasutoshi Isayama
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Patent number: 5395971Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X--Y).Type: GrantFiled: March 11, 1994Date of Patent: March 7, 1995Assignee: The Board of Regents of The University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5349109Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).Type: GrantFiled: August 26, 1993Date of Patent: September 20, 1994Assignee: The Board of Regents of the University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5344983Abstract: Process for preparing a pentane-1,5-diamine of the formula ##STR1## where R.sup.1 represents a variety of organic radicals including alkyl which can bear substituents such as hydroxyl, halogen, alkoxy, carbalkoxy, carboxyl, alkylamino, cycloalkyl or aryl, andR.sup.2 and R.sup.3 independently of one another, represent hydrogen or have the same meanings as R.sup.1 or together are a C.sub.4 -C.sub.7 -alkylene chain which is unsubstituted or substituted by one to five C.sub.1 -C.sub.4 -alkyl groups,which comprises:(a) reacting a .gamma.-cyanoketone of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given above, with excess ammonia in a first reaction space on an acidic heterogeneous catalyst at 20.degree.-150.degree. C. and 15-500 bar, and(b) hydrogenating the resulting reaction product in a second separate reaction space in the presence of excess ammonia on a cobalt, nickel or noble metal catalyst at 50.degree.-180.degree. C. and 30-500 bar.Type: GrantFiled: August 26, 1992Date of Patent: September 6, 1994Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Eberhard Fuchs, Franz Merger, Claus-Ulrich Priester
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Patent number: 5315041Abstract: A tertiary aminoalcohol having a tert-amino group(s) in the main chain and hydroxyl groups at the terminals. The use of this compound for purposes different from that of ordinary amines and amine derivatives is expected.A process for producing the tertiary aminoalcohol wherein a catalyst comprising copper, a transition metal element of the fourth period and a platinum group element of the group VIII, and further optionally containing an alkali metal or an alkaline earth metal is used.A process for producing polyurethane using the above-mentioned tertiary aminoalcohol which can solve the problems occurring in the production of a polyurethane using a tertiary amine which has a strong irritating odor and is highly irritant to the skin as a catalyst, for example, deteriorations of working atmosphere and sales appeal of the polyurethane.Type: GrantFiled: March 4, 1992Date of Patent: May 24, 1994Assignee: Kao CorporationInventors: Hiroshi Abe, Tetsuaki Fukushima, Kohshiro Sotoya, Shoichiro Harada, Hiroshi Kitagawa, Masayoshi Morii, Yasutoshi Isayama
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Patent number: 5270471Abstract: A branched chain polyalkylene polyamine ("PAPA") having plural amine groups, including a secondary amine group intermediate terminal primary amine groups one of which is hindered, and having at least two carbon atoms between each group, is selectively reductively alkylated with a ketone. The reaction provides a convenient method for selectively reductively alkylating a PAPA having a hindered primary amine group, the method comprising contacting the PAPA with hydrogen and the ketone in the presence of a catalytically effective amount of a Group VIII metal on a catalyst support, at a pressure in the range from about 500-1000 psi and a temperature in the range from about 50.degree. C. to about 200.degree. C. for a period of time sufficient to preferentially alkylate the unhindered amine primary terminal amine group. The alkylation proceeds essentially without alkylating either the sterically hindered terminal primary amine group or the intermediate unhindered secondary amine group.Type: GrantFiled: October 27, 1992Date of Patent: December 14, 1993Assignee: The B. F. Goodrich CompanyInventors: John T. Lai, Pyong-Nae Son
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Patent number: 5231217Abstract: The present invention is directed to a novel solvent-free process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of an acidic catalyst selected from the group consisting of (i) boron trifluoride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8.Type: GrantFiled: March 20, 1991Date of Patent: July 27, 1993Assignee: Miles Inc.Inventors: Robert P. Yeater, Robson Mafoti, Josef Sanders
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Patent number: 5202485Abstract: A process for preparing an N-alkylaminophenol is disclosed, comprising subjecting an aminophenol to reductive alkylation with an aldehyde or a ketone in the presence of an organic solvent and hydrogen, wherein the reductive alkylation is carried out at a temperature of from 20.degree. to 70.degree. C. in the further presence of a catalyst for reduction comprising platinum and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group, and VIB group of the Periodic Table, supported on activated carbon, or comprising palladium and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group and VIB group of the Periodic Table, supported on activated carbon.Type: GrantFiled: April 29, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Maki, Michihiro Kawasaki, Horishi Shimizu, Yoshiaki Ito
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Patent number: 5166443Abstract: A process for the preparation of a 2,2-disubstituted pentane-1,5-diamine of the formula I ##STR1## where R.sup.1 and R.sup.2, independently of one another, are C.sub.1 - to C.sub.10 -alkyl or C.sub.2 - to C.sub.10 -alkenyl or together are a C.sub.4 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by C.sub.1 - to C.sub.4 -alkyl, from a 2,2-disubstituted 4-cyanobutanal of the formula II ##STR2## where R.sup.1 and R.sup.2 are as defined above, comprises, in two spatially separate reaction spaces,a) reacting the 4-cyanobutanal of the formula II, in a first reaction space, with excess ammonia on an acidic heterogeneous catalyst at from 20.degree. to 150.degree. C.Type: GrantFiled: March 17, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Ludwig Schuster
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Patent number: 5091585Abstract: A method for continuous production of tertiary aliphatic methyl amines, particularly fatty aliphatic methyl amines such as di-hydrogenated tallow methyl amine from fatty alkyl amines, such as di-hydrogenated tallow amine over a nickel catalyst has been discovered. The reaction gives high selectivity of tertiary methyl amine over the coproduced secondary amines. The reaction may be conducted continuously in the presence of hydrogen and a formaldehyde source. The formaldehyde source may be selected from the group consisting of formaldehyde alone, formalin, a solution of mixed formaldehyde and paraformaldehyde in methanol and water, trioxane and mixtures thereof. The nickel catalyst may be promoted with copper and/or chromium, in one embodiment.Type: GrantFiled: December 21, 1990Date of Patent: February 25, 1992Assignee: Texaco Chemical CompanyInventors: Wei-Yang Su, Robert L. Zimmerman
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Patent number: 5091584Abstract: A formaldehyde/amine adduct useful in water treatment having improved stability made by reacting formaldehyde and a secondary amine, limiting the water content of the adduct to no more than 30 weight percent, optionally, adding an alcohol.Type: GrantFiled: December 20, 1990Date of Patent: February 25, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Loren D. Brake
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Patent number: 5066824Abstract: The present invention is directed to a process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of a solvent and an acidic catalyst selected from the group consisting of (i) boron trifuloride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8 with the proviso that if the primary amino group containing compound contains no aromatically bound amino groups, the pKa of said organic acid is from 0.1 to less than 0.7.Type: GrantFiled: August 3, 1990Date of Patent: November 19, 1991Assignee: Mobay CorporationInventors: Robson Mafoti, Josef Sanders
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Patent number: 4983736Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic polyphosphate condensation catalyst having a condensed structure. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentatethylenehexamine (PEHA).Type: GrantFiled: August 8, 1989Date of Patent: January 8, 1991Assignee: Union Carbide Chemicals and Plastic Company Inc.Inventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 4952734Abstract: A process for the preparation of methylamines by the reaction of amines, formaldehyde and hydrogen as starting materials on a fixed-bed catalyst in the liquid phase under pressure and preferably at elevated temperature. The starting materials contain a reduced percentage of water. They are heated to a predetermined temperature apart from each other, and then mixed with each other in the presence of the fixed-bed catalyst.Type: GrantFiled: June 23, 1988Date of Patent: August 28, 1990Assignee: Hoechst AG Werk RuhrchemieInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4940818Abstract: A process for the preparation of 2,2'-oxybis[N,N-dimethylethanamine] by reaction of 2,2'oxybisethanamine, hydrogen and formaldehyde having a reduced percentage of water on conventional fixed-bed hydrogenation catalysts. The reactants, especially the amine and formaldehyde, are heated to a predetermined temperature separate from each other, and then mixed with each other in the presence of the fixed-bed catalyst.Type: GrantFiled: June 23, 1988Date of Patent: July 10, 1990Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Franz Thonnessen, Claus Kniep
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Patent number: 4730075Abstract: A process for the production of (1) an ether or (2) a second amine comprises reacting an activated olefin with respectively an alcohol or first amine in the presence of a catalyst which is either (a) an amidine or (b) a Lewis base and epoxide. The same catalyst may also be used to carry out the reverse reaction in which an activated olefin and an alcohol or first amine are produced from the appropriate ether or second amine.Type: GrantFiled: June 20, 1986Date of Patent: March 8, 1988Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4621158Abstract: A method for making amines by reacting alcohols and/or aldehydes with primary and/or secondary amines or with ammonia in the presence of a catalyst at elevated temperature, and optionally at elevated pressure, in the liquid phase, the catalyst being an unsupported catalyst consisting of a combination of copper and tin compounds.Type: GrantFiled: August 21, 1985Date of Patent: November 4, 1986Assignee: Schering AktiengesellschaftInventors: Hans-Juergen Hubert, Klaus D. Tillmetz
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Patent number: 4540821Abstract: A process for the manufacture of aminopolyols and polyaminopolyols by continuous reductive amination of sugars in aqueous solution is described. Syrups such as corn syrups may be used directly for this process. It has been found that the lower the mol ratio of NH.sub.3 to the sugar, with a ratio of 1 as the lower limit, the higher is the degree of nitrogen incorporation into the sugar. It is essential that the streams of ammonia and aqueous sugar solution be pumped to the reaction zone separately.Type: GrantFiled: January 26, 1981Date of Patent: September 10, 1985Assignee: Texaco Inc.Inventors: John M. Larkin, Ernest L. Yeakey, Lewis W. Watts, Jr.
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Patent number: 4515986Abstract: An improved process for preparing 3-dimethylamino-2,2-dimethylpropanal from isobutyraldehyde, dimethylamine and a source of formaldehyde is disclosed wherein the process is carried out at a pH value of 9 to 11.Type: GrantFiled: August 19, 1981Date of Patent: May 7, 1985Assignee: Ruhrchemie AktiengesellschaftInventors: Wolfgang Bernhagen, Volker Falk, Helmut Springer, Jurgen Weber, Ernst Wiebus, Claus Kniep
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Patent number: 4464488Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydration catalyst to produce compounds of the formula ##STR1## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and R" is methyl or ##STR2## where R is as above. Monocarboxylic acid salts of these compounds show unexpectedly high efficiency as polyurethane catalysts. Smaller amounts of this amine are required to produce foams having the same reaction profile as foams made with prior art amine salt catalysts.Type: GrantFiled: August 11, 1983Date of Patent: August 7, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Bruce W. Peterson
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Patent number: 4433170Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydrogenation catalyst to produce new compounds of the formula ##STR1## where R is hydrogen or lower alkyl and R" is methyl or ##STR2## These compounds show unexpectedly high efficiency as polyurethane catalysts. Fewer equivalents of this amine are required to produce foams having the same reaction profile as foams made with piror art amine catalysts.Type: GrantFiled: July 20, 1981Date of Patent: February 21, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Ernest L. Yeakey
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Patent number: 4405811Abstract: A novel class of severely sterically hindered tertiary amino compounds having a pK.sub.a value at 20.degree. C. greater than 8.6, preferably ranging from 9.3 to about 10.6, and a cumulative -E.sub.s value of at least 1.9 are found to be useful in selective removal of H.sub.2 S from a normally gaseous mixture containing H.sub.2 S and CO.sub.2.Type: GrantFiled: January 18, 1982Date of Patent: September 20, 1983Assignee: Exxon Research and Engineering Co.Inventors: Eugene L. Stogryn, Guido Sartori
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Patent number: 4373107Abstract: A process for preparing an N-alkylene-diamine by contacting an alkylene diamine with an aliphatic aldehyde in a reaction solvent in the presence of hydrogen under pressure and an platinum group metal, which comprises gradually adding the aliphatic aldehyde to the alkylene diamine. The process according to the present invention provides a high conversion of the alkylene diamine and a high selectivity to the N-alkyl-alkylene-diamine.Type: GrantFiled: July 22, 1981Date of Patent: February 8, 1983Assignee: Ube Industries, Ltd.Inventors: Susumu Tahara, Keigo Nishihira, Takashi Miyatake, Hiroyuki Sawada, Junichiro Kita
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Patent number: 4338408Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydration catalyst to produce new compounds of the formula ##STR1## where R is hydrogen or lower alkyl and R" is methyl or ##STR2## These compounds show unexpectedly high efficiency as polyurethane catalysts. Fewer equivalents of this amine are required to produce foams having the same reaction profile as foams made with prior art amine catalysts.Type: GrantFiled: July 20, 1981Date of Patent: July 6, 1982Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Ernest L. Yeakey
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Patent number: 4292242Abstract: Aminomethylation of olefins which employs a homogeneous catalyst which is a solution in a suitable solvent of mixed ruthenium and iron carbonyls. The overall reaction may be represented as follows: ##STR1## where R.sub.1 and R.sub.2 are hydrogen or essentially hydrocarbon groups. The reaction proceeds by way of an aldehyde intermediate. Accordingly, the starting material may be an aldehyde instead of an olefin.Type: GrantFiled: August 26, 1980Date of Patent: September 29, 1981Assignee: SRI InternationalInventor: Richard M. Laine