Separating Primary, Secondary, Or Tertiary Amines From Each Other Patents (Class 564/499)
  • Patent number: 8785695
    Abstract: Method for purifying compounds (I) containing amino groups from a polar phase A, where (I) is converted by reaction with an aldehyde or ketone (II) into the corresponding imine (III) which is insoluble or sparingly soluble in the polar phase A, and then the imine (III) is converted to a nonpolar phase B and separated off from phase A, and then the compound containing amino groups is recovered from the imine (III).
    Type: Grant
    Filed: December 13, 2010
    Date of Patent: July 22, 2014
    Assignee: BASF SE
    Inventors: Martin Völkert, Burkhard Ernst, Wolfgang Siegel
  • Patent number: 8766010
    Abstract: The present invention relates to a mixture of ethylenediamine (EDA) and N-methylethylenediamine (Me-EDA) with a low content of Me-EDA, which comprises at least 99.5% by weight of ethylenediamine, and wherein the concentration of N-methylethylenediamine is in the range from 0.005 to 0.15% by weight. The present invention further relates to a process for distillative workup of a mixture comprising EDA, Me-EDA and water, by introducing the mixture into a distillation column which is operated at a column top pressure of 10 mbar to 4 bar, wherein the weight ratio of water to ethylenediamine in the mixture used is a*X:Y where X is the proportion by weight of water and Y is the proportion by weight of ethylenediamine at the azeotropic point of a binary mixture of water and ethylenediamine at the column top pressure in question, and a is a real number with a value of 0.9 or more.
    Type: Grant
    Filed: November 30, 2010
    Date of Patent: July 1, 2014
    Assignee: BASF SE
    Inventors: Michael Jödecke, Jörg Pastre, Randolf Hugo
  • Patent number: 8674140
    Abstract: Apparatus and processes for continuous distillative separation of a mixture comprising one or more alkanolamine(s), wherein the separation is performed in one or more dividing wall column(s) and the alkanolamine or the alkanolamines is/are withdrawn as a side draw stream or side draw streams (side fraction(s)).
    Type: Grant
    Filed: September 16, 2009
    Date of Patent: March 18, 2014
    Assignee: BASF SE
    Inventors: Willi Schmidt, Gerd Kaibel, Elke Geiβbler, Wolfgang Reif, Manfred Julius, Frank-Friedrich Pape
  • Patent number: 8664446
    Abstract: Methods of purifying NMe3 by removing N2, NH2Me, NH3, and H2O are disclosed.
    Type: Grant
    Filed: December 31, 2012
    Date of Patent: March 4, 2014
    Assignee: American Air Liquide, Inc.
    Inventors: Brian Besancon, Christian Dussarrat, Nathan Stafford, Paul Jantzen
  • Patent number: 8658831
    Abstract: According to the present invention, a method for separating a primary amine being an N,N-dialkylbisaminoalkylether, from mixtures comprising said primary amine and at least one of a secondary amine being an N,N,N?-trialkylbisaminoalkylether and a tertiary amine being an N,N,N?,N?-tetraalkylbisaminoalkylether, comprising the steps: (?) joining said mixture and at least one of a ketone and an aldehyde for reacting said primary amine with said at least one of a ketone and an aldehyde, thereby providing a primary amine based imine by a Schiff base reaction; (?) separating the primary amine based imine from said at least one of the secondary or tertiary amine; and (?) recovering the primary amine from its primary amine based imine by hydrolysis of the primary amine based imine.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: February 25, 2014
    Assignees: Huntsman International LLC, Huntsman Corporation Hungary ZRT
    Inventors: Humbert Heiko Heinrich, Gaspar Zsolt, Felber Gabor, Gaspar Attila, Grigsby Robert Alison, Jr., Kordas Imre, Vanderstraeten Petra Emma
  • Patent number: 8466323
    Abstract: A process for preparing pure triethanolamine (TEOA) by continuously distillatively separating an ethanolamine mixture comprising TEOA and diethanolamine (DEOA), by distilling off DEOA in a distillation column (DEOA column) and supplying the resulting bottom stream comprising TEOA to a downstream column (TEOA column) in which the pure TEOA is withdrawn as a side draw stream, wherein the residence time of the ethanolamine mixture in the bottom of the DEOA column is <20 minutes.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: June 18, 2013
    Assignee: BASF SE
    Inventors: Johann-Peter Melder, Gunther Van Cauwenberge, Tom Fremau, Jürgen Moors, Thilo Hahn, Bernd Stein
  • Publication number: 20120130132
    Abstract: According to the present invention, a method for separating a primary amine being an N,N-dialkylbisaminoalkylether, from mixtures comprising said primary amine and at least one of a secondary amine being an N,N,N?-trialkylbisaminoalkylether and a tertiary amine being an N,N,N?,N?-tetraalkylbisaminoalkylether, comprising the steps: (?) joining said mixture and at least one of a ketone and an aldehyde for reacting said primary amine with said at least one of a ketone and an aldehyde, thereby providing a primary amine based imine by a Schiff base reaction; (?) separating the primary amine based imine from said at least one of the secondary or tertiary amine; and (?) recovering the primary amine from its primary amine based imine by hydrolysis of the primary amine based imine.
    Type: Application
    Filed: May 6, 2010
    Publication date: May 24, 2012
    Inventors: Heiko Heinrich Humbert, Zsolt Gaspar, Gabor Felber, Attila Gaspar, Robert Alison Grigsby, JR., Imre Kordas, Petra Emma Vanderstraeten
  • Patent number: 8138378
    Abstract: A process for the separation of a first amine having a tertiary amine group and a secondary amine group such as N,N,N?-trimethylbis(aminoethyl)ether from a di-tertiary amine such as N,N,N?,N?-tetramethylbis(aminoethyl)ether, comprising: contacting a mixture of the first amine and the di-tertiary amine with a carbonyl compound capable of forming an enamine such that the carbonyl compound reacts with the first amine to form an enamine; separating the enamine from the di-tertiary amine; and subsequently converting the enamine to the first amine.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: March 20, 2012
    Assignee: Huntsman Petrochemical LLC
    Inventors: Robert A. Grigsby, Jr., Robert L. Zimmerman
  • Publication number: 20100130715
    Abstract: A process for the separation of a first amine having a tertiary amine group and a secondary amine group such as N,N,N?-trimethylbis(aminoethyl)ether from a di-tertiary amine such as N,N,N?,N?-tetramethylbis(aminoethyl)ether, comprising: contacting a mixture of the first amine and the di-tertiary amine with a carbonyl compound capable of forming an enamine such that the carbonyl compound reacts with the first amine to form an enamine; separating the enamine from the di-tertiary amine; and subsequently converting the enamine to the first amine.
    Type: Application
    Filed: June 11, 2008
    Publication date: May 27, 2010
    Applicant: Huntsman Petrochemical LLC
    Inventors: Robert A. Grigsby, JR., Robert L. Zimmerman
  • Patent number: 7309403
    Abstract: The invention relates to a method of avoiding corrosion in the separation of methylamine from a product stream (10) which is obtained in the preparation of methylamines by gas-phase reaction of methanol and ammonia and includes monomethylamine, dimethylamine, trimethylamine, ammonia and methanol as components, where ammonia is separated off by pure distillation in a first column (1), the remaining components of the product stream obtained as bottoms (12) are fed to a second column (2). Trimethylamine (14) is separated off in the second column (2) by extractive distillation with introduction of water. The further of the product stream obtained as bottoms (15) from the second column (2) are fed to a third column (3), in which monomethylamine and dimethylamine are separated off at the top. The monomethylamine and dimethylamine are separated by distillation in a fourth column (4). To avoid corrosion alkali metal hydroxide is added to the second or third column (3).
    Type: Grant
    Filed: September 24, 2004
    Date of Patent: December 18, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Reutemann, Theodor Weber, Karl-Heinz Ross, Manfred Julius
  • Patent number: 7279602
    Abstract: Process for separating triethanolamine continuously by distillation from a mixture of monoethanolamine, diethanolamine and triethanolamine together with ethanolamine ethers and water obtained by reaction of ammonia with ethylene oxide in the liquid phase under superatmospheric pressure and at elevated temperature, in which the mixture is distilled in two stages. The low-boiling fraction and the high-boiling fraction are taken off and discharged in the first stage and the intermediate-boiling fraction comprising >99.4% by weight of triethanolamine and <0.2% by weight of diethanolamine is distilled in the second stage. The distillation of the mixture is preferably carried out in a first column and a second column connected to this or in a dividing wall column.
    Type: Grant
    Filed: October 2, 2004
    Date of Patent: October 9, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reif, Hans Hammer, Guenther Ruider, Anton Meier, Philip Buskens, Matthias Frauenkron
  • Patent number: 7271292
    Abstract: The invention relates to a process for continuously, distillatively removing piperazine from an ethylenediamine-piperazine mixture under pressure at elevated temperature, by discharging the ethylenediamine at the top and the piperazine at the bottom of a distillation column. For the purpose of improving the quality of the piperazine, especially its color and color stability, the piperazine is subjected directly to circulation conveying it through an evaporator unit operated at a temperature of from about 160° C. to about 170° C. and returning it into the distillation column. After a residence time of from about 30 min to about 60 min in the circulation system, the piperazine is discharged in vapor form from a side draw in the lower section of the distillation column.
    Type: Grant
    Filed: July 28, 2006
    Date of Patent: September 18, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Jödecke, Ortmund Lang, Gunther van Cauwenberge, Matthias Frauenkron
  • Patent number: 6846959
    Abstract: A process for producing an alkanolamine includes supplying a reactive distillation apparatus having an inner contacting surface which simultaneously facilitates a reaction process and a distillation process, feeding a first reactant including an amine represented by R?3-XNHX, wherein R? is a hydrocarbon group, and X is 1, 2, or 3, feeding a second reactant including an akylene oxide represented by R?O, wherein R? is a C2-C10-alkylene, feeding a catalyst in an amount from 0% to about 15% by weight of a mixture of the first reactant, the second reactant and the catalyst; recycling an overhead output from an overhead portion including an unreacted portion of the amine and the catalyst to achieve a substantially total reflux of the amine and the catalyst, and collecting a product output including an alkanolamine, the alkanolamine being a member selected from the group consisting of a monoalkanolamine, a dialkanolamine, and a trialkanolamine.
    Type: Grant
    Filed: October 7, 2002
    Date of Patent: January 25, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Diwakar Garg, Shashank Navin Shah, Matthew Joseph Okasinski, Ava S. Drayton-Elder
  • Patent number: 6683217
    Abstract: The present invention relates to a continuous process for the manufacture of triethanolamine (TEA) comprising, in succession: (i) a step of synthesizing the TEA by continuously bringing ammonia into contact with ethylene oxide under conditions allowing the formation of a reaction mixture comprising mono-, di- and triethanolamines, (ii) a step of continuously separating the ammonia that has not reacted from the reaction mixture and (iii) a step of continuously separating the TEA from the mixture resulting from step (ii). The process is characterized in that a specific mixture of alkanolamines, comprising TEA and from 0.5 to 50% by weight of at least one secondary dialkanolamine, is prepared or isolated from the mixture resulting from step (ii), and in that the TEA is separated and isolated with a degree of purity equal to or greater than 99.2% by weight, by a continuous distillation of the specific mixture of alkanolamines.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: January 27, 2004
    Assignee: BP Chemicals Limited
    Inventors: Daniel Brun-Buisson, Philippe Villegier
  • Patent number: 6573406
    Abstract: High-purity alkanolamines, whose iron content is less than 50 ppb, are provided. Said high-purity alkanolamines can be produced by covering with an alkanolamine-resistant material at least a part of the inner wall of equipment that contacts alkanolamines from the top of the distillation tower to the storage tank in producing a high-purity alkanolamine from a crude alkanolamine by using distillation towers.
    Type: Grant
    Filed: January 24, 2002
    Date of Patent: June 3, 2003
    Assignee: Nippon Shokubai Co. Ltd.
    Inventors: Kenji Muraoka, Toshiaki Saito, Yukio Kadono
  • Patent number: 6469214
    Abstract: A process for the preparation of one or more ethanolamines (I), chosen from the group consisting of monoethanolamine, diethanolamine and triethanolamine, by conversion of one or more ethanolamines (II) different from the ethanolamine(s) (I), chosen from the group consisting of monoethanolamine, diethanolamine, triethanolamine. O,N,N-tris(2-hydroxyethyl) ethanol-N-(2-aminoethyl)-ethanolamine, N-(2-amine, hydroxy ethyl) piperazine, N-(2-hydroxyethyl)morpholine and N,N′-bis(2-hydroxyethyl)piperazine, where the ethanolamine(s) (II), optionally in the presence of ammonia, is/are treated with a strong base.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: October 22, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Johann-Peter Melder, Gerhard Schulz
  • Publication number: 20020120167
    Abstract: High-purity alkanolamines, whose iron content is less than 50 ppb, are provided. Said high-purity alkanolamines can be produced by covering with an alkanolamine-resistant material at least a part of the inner wall of equipment that contacts alkanolamines from the top of the distillation tower to the storage tank in producing a high-purity alkanolamine from a crude alkanolamine by using distillation towers.
    Type: Application
    Filed: January 24, 2002
    Publication date: August 29, 2002
    Applicant: NIPPON SHOKUBAI CO., LTD.
    Inventors: Kenji Muraoka, Toshiaki Saito, Yukio Kadono
  • Patent number: 6388137
    Abstract: Method of purifying triethanolamine prepared by reacting aqueous ammonia with ethylene oxide in the liquid phase under pressure and at elevated temperature by removing excess ammonia, water and monoethanolamine from the reaction product, reacting the resulting crude product with ethylene oxide at temperatures of from 110 to 180° C., and then rectifying the mixture in the presence of phosphorous or hypophosphorous acid or compounds thereof.
    Type: Grant
    Filed: May 31, 2001
    Date of Patent: May 14, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Günther Ruider, Karl-Heinz Ross
  • Patent number: 6353138
    Abstract: A process for the removal of primary and secondary amine and alkanolamine impurities from aqueous tertiary amine and alkanolamine solutions without affecting the tertiary amine and/or alkanolamine by treating these solutions with a monoaldehyde or dialdehyde has been described.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: March 5, 2002
    Inventor: Peter C. Rooney
  • Patent number: 6251229
    Abstract: A process for separating 2-aminomethylcyclopentylamine from a mixture consisting of hexamethylenediamine and 2-aminomethylcyclopentylamine by distilling the mixture at a pressure from 1 to 300 mbar.
    Type: Grant
    Filed: March 10, 1999
    Date of Patent: June 26, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Luyken, Alwin Rehfinger, Peter Bassler, Guido Voit, Rolf Fischer, Martin Merger, Harald Rust
  • Patent number: 6011156
    Abstract: A process is provided for removing primary amines from an amine-containing stream. Particularly, a process is provided for removing primary amines from said amine-containing stream by reacting said primary amine with a dione. More particularly, a process is provided for removing n-amylamine from an amine-containing stream comprising piperidine by reacting n-amylamine with 2,5-hexanedione.
    Type: Grant
    Filed: June 8, 1999
    Date of Patent: January 4, 2000
    Assignee: Phillips Petroleum Company
    Inventor: Michael S. Matson
  • Patent number: 5902903
    Abstract: In the process described, purification and improvement in odor of, in particular, fatty alkyldimethylamines is achieved by exposing, in the liquid phase, the tertiary amine to be treated to a vacuum or an inert gas stream. By means of the process according to the invention, in a relatively short time and in a simple and economical manner, a tertiary fatty alkylmethylamine is obtained which is essentially trimethylamine-free and improved in odor.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: May 11, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bernd Papenfuhs, Hubert Seitz, Andreas Gallas
  • Patent number: 5869696
    Abstract: Universal solid support oligonucleotide synthesis reagents, oligonucleotide synthesis processes, and reagents for cleaving oligonucleotides from solid supports are disclosed. Oligonucleotide synthesis reagents have the following general formula:SS--R.sup.6 --O--R.sup.3 Iwherein SS is a solid support; R.sup.6 is ##STR1## where R.sup.5 is hydrogen or alkyl and R.sup.4 is a phosphate protecting group; and R.sup.3 is a ring moiety having vicinal groups --XR.sup.1 and --YR.sup.2 wherein each of X and Y is independently selected from the group consisting of O, S and NH and one of R.sup.1 and R.sup.2 is a blocking moiety and the other is hydrogen or a hydroxy protecting group. Oligonucleotide cleaving reagents include methylamine and/or ammonium hydroxide and trimethylamine.
    Type: Grant
    Filed: April 22, 1996
    Date of Patent: February 9, 1999
    Assignee: Beckman Instruments, Inc.
    Inventors: M. Parameswara Reddy, Maged A. Michael, Firdous Farooqui
  • Patent number: 5608114
    Abstract: Upon subjecting trimethylamine with ammonia and optionally, a methylamine to a disproportioning reaction to reduce the proportion of the trimethylamine, use of a zeolite as a catalyst, said zeolite being mordenite, clinoptilolite or the like at least 80% of whose ion-exchangeable cations being in the form of hydrogen ions, makes it possible to efficiently conduct the reaction at a low reaction temperatures and also to suppress by-production of impurities such as acetonitrile.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: March 4, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventor: Tadamitsu Kiyoura
  • Patent number: 5481037
    Abstract: A process for the purification of tertiary amines in a crude mixture contaminated with undesirable primary and secondary amines which may have only a slight variance in boiling point with respect to the tertiary amine, wherein the crude mixture of the tertiary amine is treated at temperatures which may range from 0.degree. to 200.degree. C. but preferably from 20 to 150.degree. C. and at pressures of from 1 to 200 bar but most preferably under atmospheric pressure with a carboxylate of the formula ##STR1## in which R.sup.4 and R.sup.5 are selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, and aryl or C.sub.7 -C.sub.20 -aralkyl, both optionally mono- to penta- substituted by C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, or C.sub.4 -C.sub.12 -cycloalkylalkyl, and R.sup.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: January 2, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Fuchs, Tom Witzel, Klaus P. Stadler
  • Patent number: 5424482
    Abstract: Tertiary-butyldiethanolamine subject to color deterioration is purified and stabilized against color formation by vacuum distilling said amine at a pressure within the range of 1 to 50 mm.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: June 13, 1995
    Assignee: Elf Atochem N.A., Inc.
    Inventors: Thomas H. Overgaard, Louis P. Verduce
  • Patent number: 5292958
    Abstract: Processes for eliminating the diethanolamine present in triethanolamine and the preparation of triethanolamine or compositions containing triethanolamine substantially free from diethanolamine in which the triethanolamine containing diethanolamine is treated with glyoxal in a molar ratio of glyoxal to diethanolamine greater than or equal to 1, then if desired the triethanolamine obtained or the composition containing it is isolated, and their use.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: March 8, 1994
    Assignee: Societe Francaise Hoechst
    Inventors: Gabrielle Claud, Alain Blanc
  • Patent number: 5225597
    Abstract: A continuous method of preparing N-monoalkyl alkylenediamines, uncontaminated by the N,N'-dialkyl alkylenediamine, is based on the observation that the disubstituted material selectively precipitates from aqueous media. A scheme is presented where an aqueous alkylenediamine is reacted with a suitable carbonyl component and hydrogen over a supported platinum catalyst. Where the alkylenediamine forms an azeotrope with water it can be conveniently recycled to the reactor.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: July 6, 1993
    Assignee: UOP
    Inventor: Paul R. Kurek
  • Patent number: 5189221
    Abstract: A mixture of C.sub.1 -C.sub.4 mono-, di- and trialkylamines is separated by adding at least about an equimolar amount, based on the amine mixture, of a formyldialkanolamine selected from the group consisting of formyldiethanolamine, formyl aminoethylethanolamine and formyl 2-(2-aminoethylamino)-ethanol to the alkyl amine mixture, at a temperature of about 120.degree. to about 160.degree. C. and a pressure of about 500 to about 3,000 psig to provide a reaction mixture comprising the trialkylamine, the formyl dialkylamine and the formyl monoalkylamine, together with unreacted formyldialkanolamine and the corresponding alkanolamine, by separately recovering the trialkyl amine, the formyl dialkylamine and the formyl monoalkylamine from the reaction mixture, by reacting the dialkyl amine with said alkanolamine at atmospheric pressure at temperature of about 120.degree. to about 140.degree. C.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: February 23, 1993
    Assignee: Texaco Chemical Company
    Inventors: Roger G. Duranleau, Robert L. Zimmerman
  • Patent number: 5175369
    Abstract: This invention relates to a process for separating methoxyisopropylamine and particularly to an improvement in the process for the recovery of methoxyisopropylamine from the reaction of methoxyisopropanol with ammonia under amination conditions. In this process water is produced as a byproduct and in the separation process an azeotrope is formed which comprises about 14% water and 86% methoxyisopropylamine at atmospheric pressure. The process for enhancing separation of the azeotrope comprises contacting the azeotrope of methoxyisopropylamine and water with diisopropylamine in sufficient amount to form the azeotrope of water and diisopropylamine and separating the azeotrope from the other materials in a distillation column. The overheads in this column is charged to a decanter where water is removed as a bottoms phase and the diisopropylamine as the upper phase and returned as reflux to the distillation volumn.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: December 29, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Robert L. Fowlkes
  • Patent number: 4868335
    Abstract: This invention relates to a process for separating mono-n-hexylamine from water and particularly to an improvement in a process for the recovery of mono-n-hexylamine from the reaction of n-hexanol with ammonia under amination conditions. In this process water is produced as a by-product and in the separation process an azeotrope is formed which comprises about 49% water and 51% hexylamine. The process for enhancing separation of the azeotrope of mono-n-hexylamine and water comprises contacting the azeotrope of mono-n-hexylamine and water with di-n-hexylamine or with a mixture of di-n-hexylamine and tri-n-hexylamine in sufficient amount to reduce the solubility of mono-n-hexylamine in water thus forming an organic phase and an aqueous phase which can be separated by simple techniques, e.g., decanting.
    Type: Grant
    Filed: January 6, 1988
    Date of Patent: September 19, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Robert L. Fowlkes, Lewis S. Forester, George D. Cooper
  • Patent number: 4552958
    Abstract: A method for the separation of primary amines such as bis-(2-aminoethyl)ether from tertiary amines such as N-(2-methoxyethyl)morpholine which have close boiling points via extraction using a non-polar hydrocarbon solvent and water is described. The water may be added to a stream containing both bis-(2-aminoethyl)ether and N-(2-methoxyethyl)morpholine before extraction with the non-polar hydrocarbon is performed. The N-(2-methoxyethyl)morpholine is selectively removed by the hydrocarbon.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: November 12, 1985
    Assignee: Texaco Inc.
    Inventors: Simon P. Burns, John M. Walton, Edward E. McEntire
  • Patent number: 4552957
    Abstract: A method for the separation of primary amines such as bis-(2-aminoethyl)ether from tertiary amines such as N-(2-methoxyethyl)morpholine which have close boiling points via extraction using a non-polar hydrocarbon solvent is described. Alternatively, a polyhydroxylic compound or a mixture of such compounds may be added to a stream containing both bis-(2-aminoethyl)ether and N-(2-methoxyethyl)morpholine before extraction with the non-polar hydrocarbon is performed. The N-(2-methoxyethyl)morpholine is selectively removed by the hydrocarbon.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: November 12, 1985
    Assignee: Texaco Inc.
    Inventor: Edward E. McEntire
  • Patent number: 4543163
    Abstract: Disclosed is a process for recovering a virtually water-free amine from an amine acid salt thereof. The process comprises a unique combination of phase separation stages practiced under mild heating and distillation stages. An amine product containing less than 0.2% water can be achieved by the present process. The feedstock for the process suitably is an acid scrub liquor used to scrub amine from a vapor stream thereof which has been used in a cold-box molding process in the foundry industry or in the cure of vapor permeation curable coatings in the coatings industry.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: September 24, 1985
    Assignee: Ashland Oil, Inc.
    Inventors: David M. Stamerjohn, Richard V. Norton, Gregory P. Sturtz
  • Patent number: 4543411
    Abstract: Secondary and tertiary amines are selectively prepared by a process comprising reacting an olefin, a nitrogen-containing compound and synthesis gas in the presence of a catalyst system comprising a ruthenium-containing compound mixed with a quaternary onium salt, optionally in the presence of a solvent, heating the resultant mixture to a temperature of at least 100.degree. C. and a pressure of at least 100 psi until there is substantial formation of the desired tertiary amine and separating the desired amine by a phase separation technique.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: September 24, 1985
    Assignee: Texaco Inc.
    Inventors: John F. Knifton, David C. Alexander
  • Patent number: 4532354
    Abstract: The present invention relates to a method for purifying N,N-dimethylaminopropylamine containing 1,3-diaminopropane as an impurity. Dimethylaminopropionitrile is formed by adding dimethylamine to acrylonitrile, and is then converted by subsequent hydrogenation and distillation into N,N-dimethylaminopropylamine. The impurity 1,3-diaminopropane is removed by adding a metal salt of a transition element which forms a stable complex with the 1,3-diaminopropane.
    Type: Grant
    Filed: May 19, 1982
    Date of Patent: July 30, 1985
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Boy Cornils, Ernst Wiebus, Norbert Breitkopf
  • Patent number: 4472246
    Abstract: Disclosed is a process for recovering a virtually water-free amine from an amine acid salt thereof. The process comprises a unique combination of phase separation stages practiced under mild heating and distillation stages. An amine product containing less than 0.2% water can be achieved by the present process. The feedstock for the process suitably is an acid scrub liquor used to scrub amine from a vapor stream thereof which has been used in a cold-box molding process in the foundry industry or in the cure of vapor permeation curable coatings in the coatings industry.
    Type: Grant
    Filed: August 20, 1982
    Date of Patent: September 18, 1984
    Assignee: Ashland Oil, Inc.
    Inventors: David M. Stamerjohn, Richard V. Norton, Gregory P. Sturtz
  • Patent number: 4407703
    Abstract: A mixture of isomers of an alkylamine, for example ethylamine is separated into its constituent components by a process in which the mixture is first distilled and at least one pure component separated from the mixture. The remainder of the mixture is then subjected to a multi-stage liquid-liquid extraction, preferably in five theoretical stages using water as extractant. For example, in the separation of mixtures of ethylamines, substantially all of the mono-ethylamine and a large proportion of the di-ethylamine is recovered in the distillation stage. The use of a multi-stage extraction (instead of the more usual single-stage extraction) to treat the remainder of the mixture leads to an enhanced yield of tri-ethylamine and lower consumption of energy and of extractant.
    Type: Grant
    Filed: February 18, 1982
    Date of Patent: October 4, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: William Featherstone
  • Patent number: 4398041
    Abstract: A process for converting a C.sub.1 -C.sub.4 alcohol to a non-equilibrium controlled distribution of mono-, di- and trialkylamines is disclosed. A mixture of the alcohol and ammonia is reacted in a first conversion reactor containing a shape selective catalyst to yield a first product stream comprising the mono- and disubstituted alkylamines and substantially no trisubstituted alkylamine. A predetermined fraction of the first product stream is removed and the remainder of the stream is reacted in a second conversion reactor containing a catalyst which yields a second product stream comprising an equilibrium controlled distribution of the mono-, di- and trisubstituted alkylamine. The fraction of the first product stream and the second product stream are combined to yield an alkylamines stream comprising a non-equilibrium controlled alkylamines distribution.
    Type: Grant
    Filed: January 29, 1982
    Date of Patent: August 9, 1983
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Robert N. Cochran, Michel Deeba
  • Patent number: 4387005
    Abstract: The present invention relates to a process for carrying out the first stage of separation of constituents of a reaction mixture obtained during synthesis of asymmetric dimethylhydrazine by the Raschig method, consisting in sending, into an empty central section (B) of a column, the reaction mixture coming from said synthesis, this central section being surmounted by a column (C) in which is effected separation of the volatile compounds contained in said mixture and being extended downwardly by an exhausting section (A).
    Type: Grant
    Filed: June 2, 1981
    Date of Patent: June 7, 1983
    Assignee: Societe Europeenne de Propulsion
    Inventor: Guy Corteel
  • Patent number: 4328370
    Abstract: Lower trialkanolamines such as triethanolamine and triisopropanolamine are converted to the corresponding mono- and dialkanolamine by reacting with ammonia at about 150.degree. C.-275.degree. C. under superatmospheric pressure in the presence of a hydrogenation catalyst. The process is particularly useful for the recovery of alkanolamine values from still bottoms of alkanolamine production processes.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: May 4, 1982
    Assignee: The Dow Chemical Company
    Inventor: Michael J. Fazio
  • Patent number: 4306068
    Abstract: A method for separating primary and secondary amines by contacting a mixture thereof with mesityl oxide, which forms acetone and an adduct with the primary amine. Acetone is removed to force the reaction. The reaction is particulary useful for separating close boiling amines. The primary amine adducts have high boiling points, thereby allowing the secondary amine to be recovered in high purity by distillation. The primary amine may also be recovered by hydrolyzing the adduct which produces the primary amine and acetone.
    Type: Grant
    Filed: March 23, 1978
    Date of Patent: December 15, 1981
    Assignee: Chemical Research and Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4255356
    Abstract: A method of purifying tertiary amines by removing sec. and prim. amines and/or their hydrochlorides produced in the manufacture of the tertiary amines. The impurities are removed by dissolving the impure tertiary amines in an organic solvent and the resulting solution is passed over absorbents such as aluminum oxides having a specific surface area of about 100 to 400 square meters per gram. The sec. and prim. amines and/or their hydrochlorides are retained on the adsorbents and pure tertiary amines are useful in the solvents or can be separated therefrom. The adsorbents are regenerated by passing polar solvents thereover to remove the sec. and prim. amines and/or their hydrochlorides.
    Type: Grant
    Filed: August 8, 1979
    Date of Patent: March 10, 1981
    Assignee: Chemische Werke Huls AG
    Inventors: Alfred Coenen, Kurt Kosswig, Ferdinand Von Praun, Hans-Peter Schuller
  • Patent number: RE45240
    Abstract: A process for preparing pure triethanolamine (TEOA) by continuously distillatively separating an ethanolamine mixture comprising TEOA and diethanolamine (DEOA), by distilling off DEOA in a distillation column (DEOA column) and supplying the resulting bottom stream comprising TEOA to a downstream column (TEOA column) in which the pure TEOA is withdrawn as a side draw stream, wherein the residence time of the ethanolamine mixture in the bottom of the DEOA column is <20 minutes.
    Type: Grant
    Filed: November 21, 2013
    Date of Patent: November 11, 2014
    Assignee: BASF SE
    Inventors: Johann-Peter Melder, Gunther Van Cauwenberge, Tom Fremau, Jürgen Moors, Thilo Hahn, Bernd Stein