Producing Monohydroxy Alkyl Amines Patents (Class 564/477)
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Patent number: 5208377Abstract: Off-color N-(C.sub.4 -C.sub.10)alkyl di(C.sub.2 -C.sub.3) alkanolamines purified and decolorized by vacuum distillation at a pressure within the range of 1 to 50 mm.Hg (1-50 torr) in the presence of water and or water-soluble metal borohydride whereby the distilled alkanolamine has a reduced APHA color rating which is maintained on storage.Type: GrantFiled: September 1, 1992Date of Patent: May 4, 1993Assignee: Elf Atochem North America, Inc.Inventors: Thomas H. Overgaard, Louis P. Verduce
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Patent number: 5183923Abstract: The invention concerns a method for the preparation of polyurethane, polyester, polyamide, and polyurea diols which contain essentially all primary hydroxyl groups without capping by ethylene oxide. The method comprises coupling an alkylene oxide adduct of propylene glycol t-butyl ether or butylene glycol t-butyl ether or its aminated derivative with organic diisocyanates or dibasic acids followed by cleavage of the t-butyl group with an acid catalyst.The resulting diol is useful in many types of urethane applications including foams, elastomers and coatings.Type: GrantFiled: March 28, 1990Date of Patent: February 2, 1993Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, George P. Speranza
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Patent number: 5129917Abstract: The reaction product of certain epoxy resins and secondary amines improve the low-temperature properties of distillate fuels.Type: GrantFiled: December 3, 1990Date of Patent: July 14, 1992Assignee: Mobil Oil CorporationInventors: David J. Baillargeon, Angeline B. Cardis, Susan W. Johnson
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Patent number: 4992587Abstract: Process for preparing a ruthenium promoted, halogen-containing, nickel and/or cobalt catalyst includes impregnating, in one or more steps, a porous metal oxide support with a nickel compound and/or a cobalt compound, and a ruthenium compound to form a catalyst intermediate; reducing the nickel compound and/or cobalt compound, and ruthenium compound, in one or more steps, to the respective metal by reacting the catalyst intermediate with hydrogen gas at an elevated temperature sufficient to reduce the respective compounds to the metal; and introducing halogen by adding a halide compound at any stage in the process. Catalyst prepared by the above process and use thereof.Type: GrantFiled: June 2, 1989Date of Patent: February 12, 1991Assignee: Berol Kemi ABInventor: Juhan Koll
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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: 4939301Abstract: A process for preparing monoalkanolamines from ammonia and alkylene oxide using a catalyst which allows for high selectivity and high productivity which comprises an acid modified montmorillonite clay.Type: GrantFiled: December 23, 1988Date of Patent: July 3, 1990Assignee: Texaco Chemical CompanyInventors: Neal J. Grice, John F. Knifton
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Patent number: 4931596Abstract: Hydroxylated primary amines corresponding to the formula:R--X--CH.sub.2 --CH(OH)--CH.sub.2 NH.sub.2 (I)in which R is a saturated or unsaturated straight chain C.sub.5 -C.sub.18 aliphatic radical and X represents --O--, --S--, --NH-- or --CH.sub.2 -- are prepared by reacting an epoxide of the formula: ##STR1## in which R and X are as defined previously and R.sub.1 and R.sub.2 together represent an epoxy radical with ammonium carbamate to form the corresponding substituted ammonium carbamate of the formula: ##STR2## in which R and X are as defined previously and thereafter heating the substituted ammonium carbamate thus formed at a temperature and for a length of time sufficient to form the corresponding hydroxylated primary amine of formula (I).The hydroxylated primary amines of formula (I) and the salts of these compounds, particularly the hydrohalide, acetate and quaternary alkyl ammonium salts thereof are useful as medicaments, anticeptics, sterilizing agents and preservatives.Type: GrantFiled: January 3, 1989Date of Patent: June 5, 1990Assignee: Ethyl CorporationInventor: Kathleen S. Laurenzo
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Patent number: 4888446Abstract: The invention concerns a method for the preparation of polyoxyalkylene compounds wherein each compound has one primary amine group and one primary hydroxyl group. The method comprises alkoxylating a t-butyl ethylene, propylene or butylene glycol then aminating the product. Finally the t-butyl group is cleaved by an acid. The compounds of the method of this invention are useful in urethane/urea plastics including foams, elastomers and coatings.Type: GrantFiled: April 11, 1988Date of Patent: December 19, 1989Assignee: Texaco Chemical Co.Inventors: Howard P. Klein, Michael Cuscurida
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Patent number: 4855505Abstract: The invention relates to a ruthenium promoted nickel and/or cobalt dehydrogenation-hydrogenation catalyst. The ruthenium on the catalyst is applied from a solution containing a ruthenium halide compound. The catalyst use in organic reactions and a process performed in its presence are also described. Preferably, the catalyst is used to aminate alkylene oxides, alcohols, phenols, alkanolamines, aldehydes, and ketones.Type: GrantFiled: December 8, 1986Date of Patent: August 8, 1989Assignee: Berol Kemi ABInventor: Juhan Koll
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Patent number: 4847418Abstract: A continuous process is provided for preparing alkanolamines having a high yield of monoalkanolamine, which comprises continuously reacting a flowing stream of a homogeneous mixture of an alkylene oxide having from two to four carbon atoms and ammonia in a molar ratio of ammonia to alkylene oxide within the range from about 15:1 to about 50:1 at temperatures above the critical temperature of the mixture and at pressures above the critical pressure of the mixture and maintaining the mixture in a single phase having a density of at least 15 lbs./cu.ft. for the time necessary to form an alkanolamine product mixture containing at least about 65% by weight monoalkanolamine.Type: GrantFiled: May 16, 1988Date of Patent: July 11, 1989Assignee: Union Carbide CorporationInventors: Charles A. Gibson, Moinuddin Ahmed, James R. Nelson
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Patent number: 4845296Abstract: A process is provided for preparing alkanolamines having a high yield of monoalkanolamine which comprises reacting in a reaction mixture an alkylene oxide having from two to four carbon atoms with ammonia in a molar ratio of ammonia to alkylene oxide within the range from about 15.1 to about 50.1 at temperatures above the critical temperature of the reaction mixture and at pressures above the critical pressure of the reaction mixture and high enough to maintain the reaction mixture at sufficiently high fluid densities.Type: GrantFiled: May 12, 1988Date of Patent: July 4, 1989Assignee: Union Carbide CorporationInventors: Moinuddin Ahmed, James R. Nelson, Charles A. Gibson
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Patent number: 4612335Abstract: Polyoxyalkylene polyether amino alcohols are prepared which have the following formula: ##STR1## wherein, R represents hydrogen or a methyl or an ethyl group, x represents a number having an average value of about 1 to about 4 and n represents a number having an average value of about 1 to about 40.The polyoxyalkylene polyether amino alcohol is prepared by alkoxylating a glycol that contains one tertiary hydroyxl group and also a primary or secondary hydroxyl group in order to form an alkoxylated intermediate and by then reductively aminating the alkoxylated intermediate.Type: GrantFiled: May 6, 1985Date of Patent: September 16, 1986Assignee: Texaco, Inc.Inventors: Michael Cuscurida, Howard P. Klein
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Patent number: 4605769Abstract: Alkanoamines such as diethylaminopropanol is prepared by reacting an alkylene oxide and either an amine or ammonia is the presence of a salt of a fluorosulphonic acid.Type: GrantFiled: June 12, 1985Date of Patent: August 12, 1986Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4482743Abstract: A process for manufacturing hydroxyalkyl bis(dialkylaminoalkyl)amine is disclosed wherein dialkylaminopropylaminopropionitrile is separated from a mixture of dialkylaminopropylaminopropionitrile and bis(dialkylaminoalkyl)amine by adding to the mixture under alkoxylation conditions alkylene oxide sufficient to react with substantially all of the bis(alkylaminoalkyl)amine and then separating the reacted materials by distillation. This process yields very pure hydroxyalkyl bis(dialkylaminoalkyl)amine which is useful as a urethane catalyst.Type: GrantFiled: July 28, 1983Date of Patent: November 13, 1984Assignee: Texaco Inc.Inventors: Ernest L. Yeakey, Robert L. Zimmerman
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Patent number: 4479010Abstract: A non-catalytic procedure for reacting polyoxyalkyleneamines with alkylene oxides in the presence of 5 to 15 wt. % water is described. With this inventive procedure the addition of the oxides may be done quickly and at the surprisingly low temperature of between 75 and 85.degree. C. The proportion of tertiary amine in the resulting product ranges between 90 and 100% indicating essentially total alkoxylation. This technique is particularly suitable for propoxylation which is difficult to achieve by conventional means.Type: GrantFiled: July 20, 1983Date of Patent: October 23, 1984Assignee: Texaco Inc.Inventors: Michael Cuscurida, Walter P. Krause
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Patent number: 4471138Abstract: A novel class of severely sterically hindered secondary aminoether alcohols of the general formula: ##STR1## are prepared wherein R.sub.1 and R.sub.2 are each selected from the group consisting of alkyl and hydroxylalkyl radicals R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each selected from the group consisting of hydrogen, alkyl and hydroxyalkyl radicals, with the proviso that at least one of R.sub.4 or R.sub.5 bonded to the carbon atom directly bonded to the nitrogen atom is an alkyl or hydroxyalkyl radical when R.sub.3 is hydrogen, x and y are each positive integers ranging from 2-4 and z is a positive integer ranging from 1-4. The compounds are useful in the selective removal of H.sub.2 S from mixtures containing H.sub.2 S and CO.sub.2.Type: GrantFiled: December 27, 1982Date of Patent: September 11, 1984Assignee: Exxon Research and Engineering Co.Inventor: Eugene L. Stogryn
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Patent number: 4465858Abstract: A non-catalytic procedure for reacting polyoxyalkyleneamines with alkylene oxides in the presence of 5 to 15 wt. % water is described. With this inventive procedure the addition of the oxides may be done quickly and at the surprisingly low temperature of between 75.degree. and 85.degree. C. The proportion of tertiary amine in the resulting product is less than 90%, indicating partial alkoxylation. This technique is particularly suitable for propoxylation which is difficult to achieve by conventional means.Type: GrantFiled: July 20, 1983Date of Patent: August 14, 1984Assignee: Texaco Inc.Inventors: Michael Cuscurida, Howard P. Klein
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Patent number: 4438281Abstract: The selective production of monoalkanolamines from alkylene oxides and ammonia over acidic inorganic catalysts such as acidic silica-aluminas, natural zeolites, acid clays and others is described. These catalysts have the advantage of providing good selectivity to the monoalkanolamine together with high alkylene oxide conversion and anhydrous operation which lowers operating costs. The catalysts are also relatively low cost and have high relative heat stability.Type: GrantFiled: January 24, 1983Date of Patent: March 20, 1984Assignee: Texaco Inc.Inventor: Fred L. Johnson, Jr.
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Patent number: 4417075Abstract: A novel class of di-secondary aminoethers of the general formula: ##STR1## are disclosed wherein R.sub.1 and R.sub.8 are each independently selected from the group consisting of primary alkyl having 1 to 8 carbon atoms and primary hydroxyalkyl having 2 to 8 carbon atoms, secondary alkyl and secondary hydroxyalkyl radicals having 3 to 8 carbon atoms, tertiary alkyl and tertiary hydroxyalkyl radicals having 4 to 8 carbon atoms, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are each independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.3 alkyl and hydroxyalkyl radicals, with the proviso that R.sub.2, R.sub.3, R.sub.6, and R.sub.7 are C.sub.1 -C.sub.4 alkyl or hydroxyalkyl radicals when R.sub.1 and R.sub.8 are primary alkyl or hydroxyalkyl radicals, and at least one of R.sub.2 or R.sub.3 and R.sub.6 or R.sub.7 are C.sub.1 to C.sub.3 alkyl or hydroxyalkyl radicals when R.sub.1 and R.sub.Type: GrantFiled: January 18, 1982Date of Patent: November 22, 1983Assignee: Exxon Research and Engineering Co.Inventor: Eugene L. Stogryn
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Patent number: 4404405Abstract: There is disclosed a continuous process for making polyethylene polyamines such as diethylenetriamine, triethylenetetramine, etc. comprising the reaction of ethylene oxide with ammonia to produce a mixture of alkanolamines, the amination of the alkanolamines to ethyleneamines, and the reaction of at least a portion of the ethyleneamines thus produced with ethylene dichloride optionally in the presence of ammonia and/or water.Type: GrantFiled: September 30, 1981Date of Patent: September 13, 1983Assignee: Union Carbide CorporationInventor: John R. Winters
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Patent number: 4400539Abstract: There is described a continuous process for the manufacture of ethylenediamine from the products of the reaction of ethylene oxide and ammonia, provision of a continuous recycle stream of monoethanolamine to the products of the reaction of ethylene oxide and ammonia, the amination of such products of the reaction of ethylene oxide and ammonia combined with the monoethanolamine recycle in which the feed stream to the amination reaction zone contains at least 70 weight percent monoethanolamine as well as diethanolamine and triethanolamine, the moles of ammonia provided to the amination reaction exceeds the molar concentration of alcoholic hydroxyl groups present in the amination feed, and the feed to the amination reactor contains at least a 5% increase in the concentration of monoethanolamine over the concentration of monoethanolamine in the reaction product stream from the reaction of ethylene oxide and ammonia.Type: GrantFiled: September 30, 1981Date of Patent: August 23, 1983Assignee: Union Carbide CorporationInventors: Charles A. Gibson, John R. Winters
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Patent number: 4355181Abstract: In a process of making ethanolamines by reacting ethylene and ammonia and wherein ammonia is used in excess of the stoichiometric amount, the improvement comprising flashing and liquification at least part of the excess ammonia in the effluent prior to recycling. This moderates the operating conditions and simplifies the equipment needed to recycle the balance of the ammonia.Type: GrantFiled: February 27, 1981Date of Patent: October 19, 1982Assignee: The Dow Chemical CompanyInventors: Stephen B. Willis, Jr., Joseph D. Henry
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Patent number: 4329505Abstract: A process for preparing novel polymeric reaction products comprises commingling one molar proportion of an alkoxyalkylamine with from about 0.5 to about 2.0 molar proportions of an epihalohydrin at a temperature from about 40.degree. C. to about 150.degree. C. in the presence of an inorganic base, and recovering the reaction products. Epichlorohydrin is a preferred epihalohydrin.Type: GrantFiled: October 15, 1980Date of Patent: May 11, 1982Assignee: UOP Inc.Inventors: Gary W. Y. Kwong, Joseph Levy
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Patent number: 4324918Abstract: There are disclosed the chemical compound N,N-dimethyl-N'-isobutyl-N'-.beta.-hydroxyethyl-propylenediamine, a process for the preparation thereof and its use.Type: GrantFiled: October 3, 1980Date of Patent: April 13, 1982Assignee: Ruhrchemie AktiengesellschaftInventors: Jurgen Weber, Volker Falk, Claus Kniep
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Patent number: 4323709Abstract: Novel polymeric products are formed in the process which comprises commingling one molar proportion of a poly(oxyalkylene)amine with from about 0.5 to about 2.0 molar proportions of an epihalohydrin. Epichlorohydrin is the epihalohydrin of choice.Type: GrantFiled: October 15, 1980Date of Patent: April 6, 1982Assignee: UOP Inc.Inventor: Gary W. Y. Kwong
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Patent number: 4321271Abstract: Compounds of formula (I) ##STR1## wherein: R.sup.1 is C.sub.1-6 alkyl or C.sub.5-7 cycloalkyl;R.sup.2 is hydrogen or C.sub.1-6 alkyl; orNR.sup.1 R.sup.2 represents a heterocyclic ring having 5 to 7 ring atoms and only one hetero-atom; andR.sup.3 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenatedor salts thereof are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.Type: GrantFiled: June 30, 1980Date of Patent: March 23, 1982Assignee: Beecham Group LimitedInventor: Brian G. McDonald
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Patent number: 4281201Abstract: This invention relates to compounds of the formula: ##STR1## including derivatives thereof. The subject compounds have been found to be particularly useful as cationic emulsifiers and exhibit many desirable properties in connection with personal care compositions.Type: GrantFiled: December 10, 1979Date of Patent: July 28, 1981Assignee: Quad Chemical CorporationInventor: Phillip G. Abend