Lower Fatty Acid Patents (Class 564/137)
  • Patent number: 9139513
    Abstract: The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl 10 derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.
    Type: Grant
    Filed: November 9, 2011
    Date of Patent: September 22, 2015
    Assignee: UCB Pharma GmbH
    Inventors: Alain Merschaert, Christophe Joseph Szczepaniak, Joerg Hamann, Ralf Kanzler
  • Patent number: 9006487
    Abstract: Nitrogen-containing lipids prepared from the conjugate addition of amines to acrylates, acrylamides, or other carbon-carbon double bonds conjugated to electron-withdrawing groups are described. Methods of preparing these lipids from commercially available starting materials are also provided. These amine-containing lipids or salts forms of these lipids are preferably biodegradable and biocompatible and may be used in a variety of drug delivery systems. Given the amino moiety of these lipids, they are particularly suited for the delivery of polynucleotides. Complexes or nanoparticles containing the inventive lipid and polynucleotide have been prepared. The inventive lipids may also be used to in preparing microparticle for drug delivery. They are particularly useful in delivering labile agents given their ability to buffer the pH of their surroundings.
    Type: Grant
    Filed: June 14, 2006
    Date of Patent: April 14, 2015
    Assignee: Massachusetts Institute of Technology
    Inventors: Daniel G. Anderson, Andreas Zumbuehl, Elizaveta Sergeyevna Leshchiner (Turkhanova), Robert S. Langer, Michael Goldberg
  • Patent number: 8901328
    Abstract: Disclosed is a method involving reacting a deprotonated mono- or dialkanol amine with one or more C4 to about C75 fatty acid monoalcohol esters.
    Type: Grant
    Filed: April 11, 2012
    Date of Patent: December 2, 2014
    Assignee: Chervon Oronite Company LLC
    Inventors: Yat Fan Suen, Sarah Liz Jensen
  • Patent number: 8877972
    Abstract: A process is described for preparing alkylene oxide-adducted hydrocarbyl amides having less than 2 wt % of amine by-products by a) reacting a C4-C30 fatty acid or fatty acid lower alkyl ester with a mono- or di-hydroxy hydrocarbyl amine to form a hydrocarbyl amide; b) reacting the hydrocarbyl amide with alkylene oxide; and c) extracting the product of b) with water, acidic water, or water-containing inorganic salts or a combination thereof at a temperature from about 5° C. to 95° C. to yield an alkylene oxide-adducted hydrocarbyl amide having less than 2 wt % of amine by-products.
    Type: Grant
    Filed: September 28, 2011
    Date of Patent: November 4, 2014
    Assignee: Chevron Oronite Company LLC
    Inventors: Francois Simard, Richard E. Cherpeck
  • Publication number: 20130281664
    Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e.
    Type: Application
    Filed: October 11, 2011
    Publication date: October 24, 2013
    Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
  • Publication number: 20130274491
    Abstract: Disclosed is a method involving reacting a deprotonated mono- or dialkanol amine with one or more C4 to about C75 fatty acid monoalcohol esters.
    Type: Application
    Filed: April 11, 2012
    Publication date: October 17, 2013
    Applicant: Chevron Oronite Company LLC
    Inventors: Yat Fan Suen, Sarah Liz Jensen
  • Patent number: 8536355
    Abstract: Disclosed herein is a process for producing Dialkyl substituted fatty acids amides. More particularly the present invention provides a process for producing pure form of N,N-dimethylamide of aliphatic carboxylic acids, wherein the aliphatic carboxylic acid is Octanoic Acid and Hexanoic Acid. The disclosed process comprises condensing Alkanoyl Chloride with dilute solution of Dialkylamine at a temperature of about 8 to 12° C. and isolating the crude by salting out the reaction mixture employing Sodium Chloride and distilling the same under vacuum.
    Type: Grant
    Filed: September 22, 2005
    Date of Patent: September 17, 2013
    Inventors: Ramachandran Radhakrishnan, Sisir K. Adhikari
  • Publication number: 20120095220
    Abstract: The invention relates to a continuous method for producing amides of aliphatic carboxylic acids by reacting at least one carbonic acid ester of formula (I) R3—COOR4 (I), wherein R3 represents hydrogen or an optionally substituted aliphatic hydrocarbon group with 1 to 100 carbon atoms and R4 represents a hydrocarbon group with 1 to 30 carbon atoms, or wherein R3 and R4 form an optionally substituted ring with 5, 6 or 7 ring members, with at least one amine of formula (II) HNR1R2 (II), wherein R1 and R2 independently represent hydrogen or a hydrocarbon group with 1 to 100 C atoms, in a reaction tube the longitudinal axis of which extends in the direction of propagation of the microwaves of a monomode microwave applicator, under microwave irradiation to form carboxamide.
    Type: Application
    Filed: June 9, 2010
    Publication date: April 19, 2012
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Matthias Krull, Roman Morschhaeuser
  • Patent number: 7790924
    Abstract: A process is described for preparing alkylene oxide-adducted hydrocarbyl amides having less than 2 wt % of amine by-products by a) reacting a C4-C30 fatty acid or fatty acid lower alkyl ester with a mono- or di-hydroxy hydrocarbyl amine to form a hydrocarbyl amide; b) reacting the hydrocarbyl amide with alkylene oxide; and c) extracting the product of b) with water, acidic water, or water-containing inorganic salts or a combination thereof at a temperature from about 5° C. to 95° C. to yield an alkylene oxide-adducted hydrocarbyl amide having less than 2 wt % of amine by-products.
    Type: Grant
    Filed: November 19, 2004
    Date of Patent: September 7, 2010
    Assignee: Chevron Oronite Company LLC
    Inventors: Francois Simard, Richard E. Cherpeck
  • Patent number: 7723543
    Abstract: The invention relates to a method for the continuous production of alkyl amino acryl amides by reacting alkyl acrylates with high-boiling amines. A specific preparation technique is used in order to achieve hitherto unobtainable product qualities. Very high spatial, temporal and overall yields can also be obtained.
    Type: Grant
    Filed: November 18, 2005
    Date of Patent: May 25, 2010
    Assignee: Evonik Roehm GmbH
    Inventors: Volker Schleep, Thomas Mertz
  • Patent number: 7586004
    Abstract: The invention relates to a process for continuously preparing alkylamino(meth)acrylamide by reacting methyl (meth)acrylate, ethyl (meth)acrylate or amines having a high boiling point compared to methanol or ethanol. A special workup technique which includes removing water from the amine before entering the reactor allows product qualities which have hitherto not been attained to be achieved. In addition, very high space-time and overall yields can be achieved.
    Type: Grant
    Filed: April 13, 2004
    Date of Patent: September 8, 2009
    Assignee: Roehm GmbH & Co. KG
    Inventors: Volker Schleep, Thomas Mertz
  • Patent number: 7102032
    Abstract: In the synthesis of an amide compound through reaction of an acyl fluoride group-bearing compound with an amino compound, a reaction mixture contains the amide compound and hydrogen fluoride or a hydrofluoric acid amine salt. The amide compound is recovered in high purity form by adding an oxide, carbonate or hydroxide of an alkaline earth metal to the reaction mixture to convert the hydrogen fluoride or hydrofluoric acid amine salt to an alkaline earth metal fluoride salt that can be readily removed by filtration.
    Type: Grant
    Filed: April 21, 2004
    Date of Patent: September 5, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yasunori Sakano, Noriyuki Koike
  • Patent number: 7087783
    Abstract: A synthesis method which comprises reacting NH group-containing compounds with thiocyanates, cyanamides, nitriles or esters in the presence of a silylating agent to synthesize the corresponding nitrogen-containing addition or substitution products. This method not only enables the direct and efficient synthesis of nitrogen-containing compounds including isothioureas, guanidines, amidines and amides, but it also has a wide range of applications and is suitable for large-scale synthesis.
    Type: Grant
    Filed: October 4, 2004
    Date of Patent: August 8, 2006
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Takashi Emura, Tsuyoshi Haneishi
  • Patent number: 6660886
    Abstract: A magnetic recording medium including a lubricant topcoat having increased bonding to the medium surface comprises an amphiphilic lubricant molecule having a hydrophilic central portion including a plurality of polar functional groups bound to the medium surface and a pair hydrophobic fluoroalkyl ether or perfluoroalkylether end portions at respective ends of the hydrophilic central portion and extending away from the medium surface.
    Type: Grant
    Filed: February 1, 2002
    Date of Patent: December 9, 2003
    Assignee: Seagate Technology LLC
    Inventors: Youmin Liu, Vidya Gubbi, Chung Shih
  • Patent number: 6313294
    Abstract: The present invention provides a process for preparing an amide, which comprises reacting an amine with an ester in a molten form in the absence of a solvent.
    Type: Grant
    Filed: July 8, 1998
    Date of Patent: November 6, 2001
    Assignee: Development Center for Biotechnology
    Inventors: Wen-Chih Chou, Chang-Wei Tan, Shyh-Fong Chen, Hao Ku
  • Patent number: 6291712
    Abstract: A process for producing a saturated aliphatic carboxylic acid amide, comprising reacting a saturated aliphatic carboxylic acid with ammonia to thereby obtain a saturated aliphatic ammonium carboxylate and subjecting the saturated aliphatic ammonium carboxylate to a dehydration reaction for obtaining a saturated aliphatic carboxylic acid amide, wherein the dehydration reaction of the saturated aliphatic ammonium carboxylate is conducted while supplying water to a reaction system in which the dehydration reaction is carried out. Preferably, water is continuously supplied to the reaction system so that the production of the saturated aliphatic carboxylic acid amide is carried out in a continuous manner and the amount of water present in a steady state ranges from 20 to 70 mol per 100 mol of a total of the saturated aliphatic carboxylic acid, the ammonia, the saturated aliphatic ammonium carboxylate, the saturated aliphatic carboxylic acid amide and the water.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: September 18, 2001
    Assignee: Showa Denko K.K.
    Inventors: Shinya Saihata, Masaaki Katayama, Hitoshi Nakamura, Toshiyuki Aizawa
  • Patent number: 6235933
    Abstract: The invention relates to a process for preparing a &bgr;-hydroxyalkylamide, in which alkyl esters are reacted with &bgr;-aminoalcohols in the absence of solvents and in the presence of basic catalysts, where, to improve the selectivity, the ratio of equivalents of ester to equivalents of amine is 1:1.001 to 8.
    Type: Grant
    Filed: May 28, 1999
    Date of Patent: May 22, 2001
    Assignee: EMS-Chemie AG
    Inventors: Andreas Kaplan, Rene Gisler, Albert Reich
  • Patent number: 6194613
    Abstract: Process for the continuous preparation of hydroxyalkylamides Process for the continuous preparation of hydroxyalkylamides from carboxylic esters and alkanolamines, wherein the reaction of the starting materials is carried out in an extruder or intensive mixer by intensive mixing and brief reaction with supply of heat and simultaneous removal of the alcohol formed and the final product is then isolated.
    Type: Grant
    Filed: May 17, 1999
    Date of Patent: February 27, 2001
    Assignee: Creanova Spezialchemie GmbH
    Inventors: Thomas Weihrauch, Klaus Behrendt, Silvia Herda, Rainer Elm
  • Patent number: 6166243
    Abstract: Disclosed herein is a method for making compounds having the structural formulae (I) or (II): ##STR1## wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C.sub.1 -C.sub.4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 haloalkanoyl dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C.sub.1 -C.sub.4 alkoxy carbonyl; and R is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C.sub.3 -C.sub.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: December 26, 2000
    Assignee: CK Witco Corporation
    Inventors: Haihong Jin, Joseph A. Feiccabrino
  • Patent number: 5948778
    Abstract: This invention relates to novel statone antiviral analogs, to the processes and intermediates useful for their preparation and to their use as antiviral agents.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: September 7, 1999
    Assignee: Merrel Pharmaceuticals Inc.
    Inventors: Viviane Van Dorsselaer, Daniel Schirlin, Celine Tarnus
  • Patent number: 5861532
    Abstract: Methods for solid phase synthesis of N-alkyl amides comprise reductive amination of carbonyl compounds using a reducing agent and an amine-containing linker bound to a solid support. The methods afford high yields of linker-bound, monoalkylated amines, and subsequent coupling with acid derivatives provide derivatized N-substituted amides in excellent yields after cleavage from the solid-phase. Compositions useful in solid phase synthesis are also described.
    Type: Grant
    Filed: March 4, 1997
    Date of Patent: January 19, 1999
    Assignee: Chiron Corporation
    Inventors: Edward G. Brown, John M. Nuss
  • Patent number: 5654478
    Abstract: N-Alkenylcarboxamides of the formula I ##STR1## where at least one of the radicals R.sup.1 is hydrogen, the second radical R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by reacting an alkenyl carboxylate of the formula II ##STR2## where R.sup.1 has the abovementioned meanings and R.sup.3 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, and a carboxamide of the general formula III ##STR3## where R.sup.2 has the abovementioned meanings, in the presence of a base.
    Type: Grant
    Filed: August 10, 1995
    Date of Patent: August 5, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Bernd Fiechter
  • Patent number: 5449808
    Abstract: A process which comprises contacting and catalytically reacting under essentially anhydrous conditions in the liquid phase an amide with a nitrile according to the equation:RCONH.sub.2 +R.sup.1 CN.revreaction.RCN+R.sup.1 CONH.sub.2where R and R.sup.
    Type: Grant
    Filed: March 29, 1994
    Date of Patent: September 12, 1995
    Assignee: The Standard Oil Company
    Inventors: Marco Pagnotta, Mark C. Cesa, Sandra L. Denman, Robert D. Boyer, Jr.
  • Patent number: 5428116
    Abstract: New synthesis and analysis procedures for novel crosslinked polyamines and ampholytes. Polyamines are crosslinked with tartaric acid ester, malonic acid ester, or polycarboxylic acid esters of the citric acid cycle. The resulting crosslinked polyamine may further react with other compounds such as an .alpha.,.beta.-unsaturated or .alpha.-halo unsaturated carboxylic acids to prepare new ampholyte mixtures. The resulting novel ampholytes exhibit greater heterogeneity and complexity than presently prepared ampholytes, and can be used in analytical and preparative isoelectric focusing processes.Novel ampholyte analysis process entails analyzing chemical compounds, usually ampholytes, used in isoelectric focusing processes. The ampholyte is isoelectrically focused on an immobilized pH gradient, and then immersed in a picric acid solution to cause precipitation and visualization of amphoteric species.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: June 27, 1995
    Assignee: Board of Regents, The University of Texas System
    Inventors: L. Scott Rodkey, Philip R. DeShong
  • Patent number: 5217634
    Abstract: A material useful as a dispersant additive in oleaginous compositions selected from fuels and lubricating oils comprising the reaction products of:(i) at least one intermediate adduct comprised of the reaction products of(a) at least one polyepoxide, and(b) at least one member selected from the group consisting of polyamines, polyols, and amino alcohols; and(ii) at least one of (a) hydrocarbyl substituted C.sub.3 -C.sub.10 monocarboxylic or C.sub.4 -C.sub.10 dicarboxylic acid producing material; (b) an aldehyde and a hydrocarbyl substituted hydroxy aromatic compound; or (c) an aldehyde and the reaction product of a hydrocarbyl substituted C.sub.3 -C.sub.10 monocarboxylic or C.sub.4 -C.sub.10 dicarboxylic acid or anhydride and an amine substituted hydroxy aromatic compound.Also included is a process for preparing said material and an oleaginous composition containing said material.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: June 8, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jacob Emert, Antonio Gutierrez, Robert D. Lundberg
  • Patent number: 5194668
    Abstract: Carboxylic acid esters and formamide are efficiently obtained by reacting carboxylic acid amides and formic acid esters, or by reacting carboxylic acid amides, alcohols and carbon monoxide in the presence of a dehydrated condensate of carboxylic acid amide with an alkali metal hydroxide or an alkaline earth metal hydroxide catalyst.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: March 16, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideo Ikarashi, Hirofumi Higuchi, Koichi Kida
  • Patent number: 5155269
    Abstract: A process for removing impurities from an aqueous feed mixture comprising a reaction solution produced by catalytic hydrogenation of nitrobenzene in an acid aqueous medium. An aqueous feed mixture comprising the reaction solution is contacted with an extractant comprising aniline for extraction from the feed mixture of 4,4'-diaminodiphenylether, thereby providing a primary raffinate that contains p-aminophenol and is contaminated with aniline. The primary raffinate is contacted at a pH of between about 5.5 and about 8.0 with a purifying solvent, the purifying solvent comprising an organic solvent effective for extraction of aniline from the primary raffinate, thereby producing a purified raffinate comprising p-aminophenol.Also described is a unified process for the preparation of N-acetyl-p-aminophenol in which p-aminophenol contained in the aforesaid purified raffinate is acetylated without prior separation of solid p-aminophenol from the raffinate.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: October 13, 1992
    Assignee: Mallinckrodt
    Inventors: Thomas J. Dunn, Vojko B. Jovanovic
  • Patent number: 5101073
    Abstract: A method of preparing solid hydroxyalkylamides by reacting carboxylic alkyl esters with alkanolamines at controlled reaction temperatures, removing the alcohol byproduct, controlling the temperature of the reaction mixture to form a slurry, maintaining the slurry and recovering the solid hydroxyalkylamides.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: March 31, 1992
    Assignee: Rohm and Haas Company
    Inventor: Francis W. Schlaefer
  • Patent number: 5034536
    Abstract: Unsaturated esters with an alkyl group at the 2 carbon, such as methyl methacrylate, react with .beta.-aminoalkanols, such as 2-aminoethanol, in the presence of an alkali metal alkoxide or hydroxide such as sodium methoxide, under moderate temperatures to form an amide such as N-(2-hydroxyethyl)methacrylamide. The amide may be cyclized by a weak Lewis acid, such as ferric chloride, at about 220.degree. C. to form a 2-alkenyl oxazoline, such as isopropenyl oxazoline.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: July 23, 1991
    Assignee: The Dow Chemical Company
    Inventor: Michael J. Fazio
  • Patent number: 5023375
    Abstract: Ethylidene bisamide is produced by the reaction of vinyl acetate with a primary carboxylic acid amide over a catalytic amount of a salt of palladium (II), platinum(II) or mercury(II). The reaction is carried out in the presence of an aliphatic or arylaliphatic alcohol in a concentration greater than 0.01 equivalents based upon the limiting reagent.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: June 11, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Mark L. Listemann
  • Patent number: 4990651
    Abstract: Carboxylic acid esters, industrially important compounds, are obtained by reacting carboxylic acid amides and formic acid esters, or carboxylic acid amides, alcohols and carbon monoxide in the presence of metal alcoholate.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: February 5, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideo Ikarashi, Yoshio Kawai, Seiji Nagasawa, Hiroyuki Hirayama
  • Patent number: 4973739
    Abstract: Carboxylic acid esters, industrially important compounds, are efficiently obtained by reacting carboxylic acid amides with formic acid esters in the presence of an inorganic solid acid catalyst.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: November 27, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Seiji Nagasawa, Hideo Ikarashi, Yoshio Kawai, Hiroyuki Hirayama
  • Patent number: 4855455
    Abstract: A hydroxy-carboxylate ester is converted to an amino-acid-amide by replacement of the --OH group with --N.sub.3, via, e.g., CH.sub.3 SO.sub.2 Cl and NaN.sub.3 ; reacting with amine to convert the ester to amide; and hydrogenating --N.sub.3 to --NH.sub.2. The present process alleviates the conventional use of blocking-deblocking procedures.
    Type: Grant
    Filed: January 22, 1988
    Date of Patent: August 8, 1989
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Robert J. Kupper
  • Patent number: 4675442
    Abstract: What is disclosed is a method for making an amide of acrylic acid or of methacrylic acid by the reaction of an alkyl ester of acrylic acid or of methacrylic acid with an amine at a temperature between 50.degree. C. and 180.degree. C., whereby the reaction with the amine is carried out in the presence of a catalytic amount of a compound of a metal of Group IVB of the periodic table of the elements or of a compound of lead, zinc, or tantalum.
    Type: Grant
    Filed: March 6, 1985
    Date of Patent: June 23, 1987
    Assignee: Rohm GmbH
    Inventors: Siegmund Besecke, Guenter Schroeder
  • Patent number: 4659866
    Abstract: Formamide is prepared continuously from methyl formate and ammonia, pure methanol being recovered, by a process wherein(a) the reaction of methyl formate and ammonia is carried out predominantly in the liquid phase in the upper region of a reaction column R having a total of from 15 to 30 theoretical plates,(b) the methanol formed in this reaction is removed, together with small amounts of formamide, from the column or the evaporator in vaporus form at the level of plates 1-5 (counted from the bottom),(c) the formamide is removed from this methanol/formamide mixture, together with small amounts of methanol, in a distillation column D1 and recycled to R, and(d) the small amounts of methanol contained in the bottom product from R, which substantially consists of formamide and in this column should be at from 110.degree. to 130.degree. C., are separated off in a distillation column D2.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: April 21, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Kaspar Bott, Gerd Kaibel, Herwig Hoffmann, Rudolf Irnich, Otto Kratzer
  • Patent number: 4613673
    Abstract: This invention is directed to novel catalysts characterized as compounds of tin or zinc containing a direct metal-nitrogen bond. The novel catalysts are derived from a primary or secondary amine such as an alkyl amine, a heterocyclic amine, an aromatic amine, etc. The amine is reacted with a tin compound such as a tin chloride, a tin bromide, a tin oxide, or a tin alkoxide. Alternatively, the amine may be reacted with a zinc halide, a zinc alkoxide or an organozinc compound.In another aspect of the present invention, the novel catalysts are used to catalyze the reaction of an acrylate or methacrylate ester with an amine in order to prepare N-substituted acrylamides or methacrylamides in good yield and with high selectivity.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: September 23, 1986
    Assignee: Texaco Inc.
    Inventors: Edward E. McEntire, Kathy B. Sellstrom
  • Patent number: 4590292
    Abstract: A modified novel process for preparing cyclopropylamine from .gamma.-butyrolactone is described. The .gamma.-butyrolactone ring is cleaved with a hydrohalide in the presence of a novel catalyst comprising an aqueous sulfuric acid solution. The 4-chlorobutyric acid, thus formed is converted into a hindered chlorobutyrate ester. The hindered ester based on secondary and tertiary alkanols of eight or less carbon atoms, is cyclized to form the hindered cyclopropanecarboxylate ester by a novel reaction medium consisting of solid caustic in a water-immiscible solvent and a phase transfer catalyst. The hindered cyclopropanecarboxylate ester is ammoniated to form cyclopropanecarboxamide by a novel catalyst comprising an alkali metal salt of a polyol having hydroxy groups on adjacent carbons. The carboxamide formed in substantially quantitative yields is converted to cyclopropylamine by a modified Hofmann reaction utilizing continuous degradation of the intermediate with simultaneous distillation.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: May 20, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph T. Blackwell, Harold L. Daughety, Henry C. Grace, Ward H. Oliver
  • Patent number: 4539427
    Abstract: Formamides e.g. diethylformamide are prepared by reacting a primary or secondary amine e.g. diethylamine or ammonia with (a) an alkyl formate or (b) carbon monoxide and an alkanol in the presence, as catalyst, of (i) a compound containing an amidine group or (ii) a Group V element-containing Lewis base and an epoxide. The Lewis base can be a trivalent nitrogen or phosphorus-containing compound. The amidine group which can be cyclic or acyclic can form part of a guanidine group.
    Type: Grant
    Filed: October 18, 1983
    Date of Patent: September 3, 1985
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4379928
    Abstract: Alkyl amides have been synthesized from cyclic anhydrides, carboxyl acids and their esters by contacting them with an amine carbamic acid salt.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: April 12, 1983
    Assignee: Union Carbide Corporation
    Inventor: Spyros Theodoropulos
  • Patent number: 4358612
    Abstract: Amides having the formulaRCONR.sub.2 R.sub.3in which R is .alpha.-halo-C.sub.1 -C.sub.8 -alkyl; R.sub.2 is C.sub.1 -C.sub.8 alkyl, and R.sub.3 is C.sub.1 -C.sub.8 alkyl, are prepared by reacting an ester with an amine in the presence of a promotor which is a halide of a Group IIIa metal having a molecular weight of 26 or greater, or of a Group IVb metal. The process is particularly suitable for production of a desired optical isomer of such an amide.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: November 9, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Richard D. Gless, Jr.
  • Patent number: 4322551
    Abstract: A process for the preparation of aromatic amide antioxidants from a simple aliphatic or aromatic ester and primary amine in the presence of a metal alkoxide and an alcohol. Unsaturated products produced using this process are sufficiently pure to use as comonomers in the preparation of elastomers.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: March 30, 1982
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Niranjan V. Shah
  • Patent number: 4311857
    Abstract: Described are D-(threo)-1-aryl-2-acylamido-3-fluoro-1-propanol esters and salts thereof, methods for their preparation, and methods for their use as antibacterial agents.
    Type: Grant
    Filed: April 4, 1980
    Date of Patent: January 19, 1982
    Assignee: Schering Corporation
    Inventor: Tattanahalli L. Nagabhushan
  • Patent number: 4259259
    Abstract: Covers a process for the preparation of a .beta.-aminopropionanide of the formula ##STR1## wherein R.sub.1 is H or methyl, n is an integer of 2 to 6 and R.sub.2 and R.sub.3, taken singly are hydrogen or lower alkyl groups containing 1 to 4 carbon atoms or R.sub.2 and R.sub.3, taken jointly are combined with the nitrogen atom to form a heterocyclic group selected from the groups consisting of morpholine, pyrrolidine and piperidine ring groups; which process comprises reacting in the presence of an alkali or alkaline earth metal salt of a strong acid having a pK.sub.a of less than about 2.0 acting as a catalyst a tertiaryaminoalkyl amine of the formula: where R.sub.2, R.sub.3 and n are as above with an acrylic or methacrylic compound of the formula: ##STR2## where R.sub.1 is as above and R.sub.4 is lower alkyl and recovering said .beta.-aminopropionamide.
    Type: Grant
    Filed: November 15, 1979
    Date of Patent: March 31, 1981
    Assignee: Texaco Development Corp.
    Inventor: Edward E. McEntire
  • Patent number: 4258200
    Abstract: Carboxylic acid amides are produced by the catalytic reaction of an ester and an amine is shown. Organo cobalt salts are used as the catalyst. The process is particularly useful for producing dimethylacetamide by the reaction of methyl acetate and dimethylamine.
    Type: Grant
    Filed: March 11, 1980
    Date of Patent: March 24, 1981
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Randall J. Daughenbaugh