Producing Monohydroxy Alkyl Amines Patents (Class 564/477)
  • Patent number: 5208377
    Abstract: 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: Grant
    Filed: September 1, 1992
    Date of Patent: May 4, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventors: Thomas H. Overgaard, Louis P. Verduce
  • Patent number: 5183923
    Abstract: 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: Grant
    Filed: March 28, 1990
    Date of Patent: February 2, 1993
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, George P. Speranza
  • Patent number: 5129917
    Abstract: The reaction product of certain epoxy resins and secondary amines improve the low-temperature properties of distillate fuels.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: July 14, 1992
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Angeline B. Cardis, Susan W. Johnson
  • Patent number: 4992587
    Abstract: 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: Grant
    Filed: June 2, 1989
    Date of Patent: February 12, 1991
    Assignee: Berol Kemi AB
    Inventor: Juhan Koll
  • Patent number: 4983736
    Abstract: 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: Grant
    Filed: August 8, 1989
    Date of Patent: January 8, 1991
    Assignee: Union Carbide Chemicals and Plastic Company Inc.
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck
  • Patent number: 4939301
    Abstract: 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: Grant
    Filed: December 23, 1988
    Date of Patent: July 3, 1990
    Assignee: Texaco Chemical Company
    Inventors: Neal J. Grice, John F. Knifton
  • Patent number: 4931596
    Abstract: 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: Grant
    Filed: January 3, 1989
    Date of Patent: June 5, 1990
    Assignee: Ethyl Corporation
    Inventor: Kathleen S. Laurenzo
  • Patent number: 4888446
    Abstract: 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: Grant
    Filed: April 11, 1988
    Date of Patent: December 19, 1989
    Assignee: Texaco Chemical Co.
    Inventors: Howard P. Klein, Michael Cuscurida
  • Patent number: 4855505
    Abstract: 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: Grant
    Filed: December 8, 1986
    Date of Patent: August 8, 1989
    Assignee: Berol Kemi AB
    Inventor: Juhan Koll
  • Patent number: 4847418
    Abstract: 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: Grant
    Filed: May 16, 1988
    Date of Patent: July 11, 1989
    Assignee: Union Carbide Corporation
    Inventors: Charles A. Gibson, Moinuddin Ahmed, James R. Nelson
  • Patent number: 4845296
    Abstract: 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: Grant
    Filed: May 12, 1988
    Date of Patent: July 4, 1989
    Assignee: Union Carbide Corporation
    Inventors: Moinuddin Ahmed, James R. Nelson, Charles A. Gibson
  • Patent number: 4612335
    Abstract: 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: Grant
    Filed: May 6, 1985
    Date of Patent: September 16, 1986
    Assignee: Texaco, Inc.
    Inventors: Michael Cuscurida, Howard P. Klein
  • Patent number: 4605769
    Abstract: 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: Grant
    Filed: June 12, 1985
    Date of Patent: August 12, 1986
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4482743
    Abstract: 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: Grant
    Filed: July 28, 1983
    Date of Patent: November 13, 1984
    Assignee: Texaco Inc.
    Inventors: Ernest L. Yeakey, Robert L. Zimmerman
  • Patent number: 4479010
    Abstract: 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: Grant
    Filed: July 20, 1983
    Date of Patent: October 23, 1984
    Assignee: Texaco Inc.
    Inventors: Michael Cuscurida, Walter P. Krause
  • Patent number: 4471138
    Abstract: 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: Grant
    Filed: December 27, 1982
    Date of Patent: September 11, 1984
    Assignee: Exxon Research and Engineering Co.
    Inventor: Eugene L. Stogryn
  • Patent number: 4465858
    Abstract: 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: Grant
    Filed: July 20, 1983
    Date of Patent: August 14, 1984
    Assignee: Texaco Inc.
    Inventors: Michael Cuscurida, Howard P. Klein
  • Patent number: 4438281
    Abstract: 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: Grant
    Filed: January 24, 1983
    Date of Patent: March 20, 1984
    Assignee: Texaco Inc.
    Inventor: Fred L. Johnson, Jr.
  • Patent number: 4417075
    Abstract: 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: Grant
    Filed: January 18, 1982
    Date of Patent: November 22, 1983
    Assignee: Exxon Research and Engineering Co.
    Inventor: Eugene L. Stogryn
  • Patent number: 4404405
    Abstract: 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: Grant
    Filed: September 30, 1981
    Date of Patent: September 13, 1983
    Assignee: Union Carbide Corporation
    Inventor: John R. Winters
  • Patent number: 4400539
    Abstract: 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: Grant
    Filed: September 30, 1981
    Date of Patent: August 23, 1983
    Assignee: Union Carbide Corporation
    Inventors: Charles A. Gibson, John R. Winters
  • Patent number: 4355181
    Abstract: 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: Grant
    Filed: February 27, 1981
    Date of Patent: October 19, 1982
    Assignee: The Dow Chemical Company
    Inventors: Stephen B. Willis, Jr., Joseph D. Henry
  • Patent number: 4329505
    Abstract: 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: Grant
    Filed: October 15, 1980
    Date of Patent: May 11, 1982
    Assignee: UOP Inc.
    Inventors: Gary W. Y. Kwong, Joseph Levy
  • Patent number: 4324918
    Abstract: 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: Grant
    Filed: October 3, 1980
    Date of Patent: April 13, 1982
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Volker Falk, Claus Kniep
  • Patent number: 4323709
    Abstract: 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: Grant
    Filed: October 15, 1980
    Date of Patent: April 6, 1982
    Assignee: UOP Inc.
    Inventor: Gary W. Y. Kwong
  • Patent number: 4321271
    Abstract: 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: Grant
    Filed: June 30, 1980
    Date of Patent: March 23, 1982
    Assignee: Beecham Group Limited
    Inventor: Brian G. McDonald
  • Patent number: 4281201
    Abstract: 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: Grant
    Filed: December 10, 1979
    Date of Patent: July 28, 1981
    Assignee: Quad Chemical Corporation
    Inventor: Phillip G. Abend