Lower Fatty Acid Patents (Class 564/141)
  • Patent number: 9527065
    Abstract: The present invention relates to a catalyst for glycerin dehydration, a preparation method thereof, and a preparation method of acrolein. The catalyst for glycerin dehydration exhibits a high glycerin conversion ratio, minimizes by-product formation to improve acrolein selectivity, and also maintains high catalytic activity during reaction.
    Type: Grant
    Filed: November 18, 2014
    Date of Patent: December 27, 2016
    Assignee: LG Chem, Ltd.
    Inventors: Ji Yeon Kim, Jun Seon Choi, Joo Young Cheon, Wang Rae Joe
  • 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
  • Patent number: 8853439
    Abstract: The invention relates to improved processes for the preparation of lacosamide. The invention also relates to a novel intermediate useful in the preparation of lacosamide. The invention also relates to process for the purification of lacosamide.
    Type: Grant
    Filed: September 23, 2010
    Date of Patent: October 7, 2014
    Assignee: Cadila Healthcare Limited
    Inventors: Bipin Pandey, Kalpesh Shah
  • Patent number: 8759373
    Abstract: The present invention relates to cyanoisoquinoline compounds suitable for use in treating hypoxia inducible factor-mediated and/or erythropoietin-associated conditions.
    Type: Grant
    Filed: March 26, 2012
    Date of Patent: June 24, 2014
    Assignee: Fibrogen, Inc.
    Inventors: Michael P. Arend, Lee A. Flippin, Min Wu, Eric D. Turtle, Wen-Bin Ho, Shaojiang Deng
  • Patent number: 8334411
    Abstract: A method for producing a diamine includes purifying a diamine from an aqueous solution containing a diamine salt by adding an alkaline substance to the aqueous solution and then filtering the resulting solution by allowing the solution to pass through a nanofiltration membrane to remove the salt, thereby obtaining an aqueous diamine solution.
    Type: Grant
    Filed: March 11, 2009
    Date of Patent: December 18, 2012
    Assignee: Toray Industries, Inc.
    Inventors: Masateru Ito, Izumi Nakagawa, Koya Kato, Takashi Mimitsuka, Kenji Sawai, Shin-ichi Minegishi, Hideki Sawai, Katsushige Yamada
  • Publication number: 20120215028
    Abstract: Biobased multifunctional cross-linking polyols that can be used in preparing polyesters and in polyurethane applications, and methods of making them are described.
    Type: Application
    Filed: September 30, 2010
    Publication date: August 23, 2012
    Inventors: Daniel Garbark, Herman Paul Benecke
  • Publication number: 20120209022
    Abstract: The invention relates to improved processes for the preparation of lacosamide. The invention also relates to a novel intermediate useful in the preparation of lacosamide. The invention also relates to process for the purification of lacosamide.
    Type: Application
    Filed: September 23, 2010
    Publication date: August 16, 2012
    Applicant: CADILA HEALTHCARE LIMITED
    Inventors: Bipin Pandey, Kalpesh Shah
  • Patent number: 8183413
    Abstract: Provided is a process for production of a ?-amino-?-hydroxy carboxamide derivative that is important in production of drugs or the like. In the presence of a predetermined solvent, a ?-(N-protected)amino-?-hydroxycarboxylic acid is reacted with an amine to conversion to a ?-(N-protected)amino-?-hydroxy carboxamide derivative; then the derivative is deprotected for conversion to a ?-amino-?-hydroxy carboxamide derivative; and the derivative is crystallized using a protic solvent to obtain a crystal. The high-purity ?-amino-?-hydroxy carboxamide derivative can be stably produced on an industrial scale by the process.
    Type: Grant
    Filed: January 16, 2007
    Date of Patent: May 22, 2012
    Assignee: Kaneka Corporation
    Inventors: Narumi Kishimoto, Hiroaki Yasukouchi, Toshihiro Takeda
  • Publication number: 20120108667
    Abstract: Disclosed herein are compounds, compositions, methods of treatment and synthetic methods for making compounds related to Ceramides and the use of Ceramides.
    Type: Application
    Filed: October 31, 2011
    Publication date: May 3, 2012
    Inventors: Zdzislaw M. Szulc, Alicja Bielawska, Yusuf A. Hannun
  • Publication number: 20110130350
    Abstract: The present invention is concerned with an improved method of producing (R)-2-acetamido-N-benzyl-3-methoxypropionamide (lacosamide) comprising the 0-methylation of a compound of formula (I) to produce a compound of formula (II) in a single step reaction.
    Type: Application
    Filed: December 7, 2010
    Publication date: June 2, 2011
    Applicant: UCB PHARMA GMBH
    Inventors: Jens Riedner, Gavin Dunne
  • Publication number: 20110118479
    Abstract: In accordance with the disclosure, one aspect of the present application is directed to a dispersant compound comprising the reaction product of (i) a hydrocarbyl carbonyl compound, (ii) a polycarbonyl compound having at least three carbonyl acylating functions, and (iii) a primary amine moiety of a polyamine. Methods of making and methods of using the dispersant compound are also disclosed.
    Type: Application
    Filed: December 21, 2010
    Publication date: May 19, 2011
    Applicant: AFTON CHEMICAL CORPORATION
    Inventor: John T. Loper
  • Publication number: 20110098319
    Abstract: The invention relates to novel derivatives of short-chain fatty acids, in particular derivatives of butyric acid, useful for all the known clinical applications of the latter, which show physicochemical characteristics suitable for an easy oral administration, being devoid of the unpleasant organoleptic properties that characterize butyrate. The new compounds are amide derivatives which can be synthesized by reaction of the corresponding fatty acid halide with a naturally occurring amino acid, phenylalanine or a suitable derivative thereof, and which are in a poorly hygroscopic, easily weighable form, stable to acids and alkalis and able to release the acid at the small and large bowel level in a constant manner over time. They do not have disagreeable odors and are practically tasteless, thus allowing the manufacture of preparations for oral administration also suitable for the therapy of chronic diseases and in the pediatric field.
    Type: Application
    Filed: April 21, 2009
    Publication date: April 28, 2011
    Inventors: Roberto Berni Canani, Antonio Calignano, Orietta Mazzoni, Anna Coruzzo
  • 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: 7538247
    Abstract: The invention is directed to a process for the preparation of ?,?-unsaturated acids, esters and amides from ?- or ?-hydroxycarboxylic acids or esters or precursors in high yields and high selectivity. The ?,?-unsaturated acids or esters are optionally prepared in the presence of specific dehydration and/or esterification catalysts. The ?,?-unsaturated amides or substituted amides are prepared optionally in the presence of a dehydration and/or amidation catalyst. The source of ?- or ?-hydroxycarboxylic acids or precusor is preferably from a renewable resource. The precursor is defined herein.
    Type: Grant
    Filed: March 30, 2005
    Date of Patent: May 26, 2009
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Liliana Craciun, Gerald P. Benn, John Dewing, George W. Schriver, William J. Peer, Bernd Siebenhaar, Urs Siegrist
  • Patent number: 7439394
    Abstract: Novel cyclohexyl-1,4-diamine compounds corresponding to formula I, processes for the production thereof, pharmaceutical compositions containing these compounds, methods of producing pharmaceutical compositions including these compounds and related methods of treating or inhibiting certain diseases or conditions.
    Type: Grant
    Filed: November 9, 2006
    Date of Patent: October 21, 2008
    Assignee: Gruenenthal GmbH
    Inventors: Corinna Sundermann, Bernd Sundermann
  • Patent number: 6670506
    Abstract: A method of synthesis of dinitro-diaza-alkanes and intermediate products thereto from alkylamines and esters, whereby a dialkyl ester of a dicarboxylic acid is reacted with an alkylamine in an aqueous medium to form the corresponding dialkyldiamide of the dicarboxylic acid; the resulting dialkyldiamide is nitrated by means of conventional nitration agents to form the corresponding dialkyldinitroamide of the dicarboxylic acid and; the resulting dialkyldinitroamide is reacted with methylamine and/or ethylamine in an aquous medium to yield a corresponding alkylnitroamine and the dimethyldiamide and/or diethyldiamide of the dicarboxylic acid, and the alkylnitroamine is isolated from that, and the isolated alkylnitroamine is condensed in a known manner to form the dinitro-diaza-alkanes.
    Type: Grant
    Filed: November 1, 2001
    Date of Patent: December 30, 2003
    Assignee: Nitrochemie Achau GmbH
    Inventor: Thomas Knott
  • Patent number: 6384278
    Abstract: The present invention provides an inexpensive one-step method for preparing an aromatic carboxamide, such as a phenyl substituted carboxamide) by reacting an aromatic amine (e.g. a phenylamine) and a carboxylic acid (e.g. an alkanoic acid or ester thereof) in the presence of a boron containing compound (e.g. boronic acid or boric acid) and, optionally, a chelating agent (e.g. a 2-pyridinylamine).
    Type: Grant
    Filed: February 5, 2001
    Date of Patent: May 7, 2002
    Assignee: Emisphere Technologies, Inc.
    Inventors: Pingwah Tang, Feng Ye
  • Patent number: 6215024
    Abstract: The present invention provides a novel single step process for the production of amides from amines comprising reaction of amines with an acylating agent comprising of a carboxylic acid in a molar ratio of 1:3 to 1:10 in the presence of reusable natural montmorillonite/metal ion-exchanged clay catalysts, in a suitable solvent medium at a temperature in the range of 30-160° C. for a period of 0.02 to 6 hrs, and recovering the corresponding amides by a conventional simple work-up procedure.
    Type: Grant
    Filed: October 4, 1999
    Date of Patent: April 10, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Veldurthy Bhaskar, Mannepalli Lakshmi Kantam, Kottapalli Koteswara Rao, Kondapuram Vijaya Raghavan
  • 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: 6107498
    Abstract: Methods for producing carboxylic amides involves combining near-stoichiometric amounts of carboxylic acid and amine in a reaction vessel and reacting under pressures greater than atmospheric pressure. Alternatively, an excess of amine is reacted with carboxylic acid at atmospheric pressure to produce a carboxylic amide.
    Type: Grant
    Filed: April 22, 1997
    Date of Patent: August 22, 2000
    Assignee: AKZO Nobel N.V.
    Inventors: Bernard Maisonneuve, Dale Steichen, Ralph Franklin, Kornelis Overkempe
  • Patent number: 5998668
    Abstract: An optically active (2S,3R)-2-(3'-hydroxyacyl)aminoalkane-1,3-diol and a process for producing the same are disclosed. The compound is represented by the following general formula (1): ##STR1## wherein R.sup.1 represents a linear or branched, saturated aliphatic hydrocarbon group having 9 to 19 carbon atoms; R.sup.2 represents a linear or branched, saturated aliphatic hydrocarbon group having 1 to 19 carbon atoms; and symbol * means that the carbon atom is an asymmetric carbon atom of the S or R configuration. The optically active compound is a ceramide in which the fatty acid moiety has an optically active hydroxyl group in the 3-position.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: December 7, 1999
    Assignee: Takasago International Corporation
    Inventors: Kazutoshi Sakurai, Kenya Ishida, Miharu Ogura
  • Patent number: 5962708
    Abstract: The invention relates to a process for the preparation of highly concentrated free-flowing and pumpable aqueous solutions of betaines by quaternization of a compound which contains tertiary amine nitrogen with a .omega.-halo carboxylic acid characterized in that 0.5-5% by weight of the final product, of a viscosity-reducing compound such as an alkali or alkaline earth metal citric acid salt is added to the reaction mixture before or during the quaternization reaction.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: October 5, 1999
    Assignee: Witco Surfactants GmbH
    Inventors: Ingo Hamann, Hans-Jurgen Kohle, Winfried Wehner
  • Patent number: 5945543
    Abstract: A process for preparing .alpha.-(N,N-dialkylamino) carboxamides of the formula I ##STR1## where the substituents have the stated meanings, comprises reacting the corresponding free acids with primary or secondary amines in the presence of anhydrides of an alkanephosphonic acid.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: August 31, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Thomas Zierke
  • Patent number: 5883132
    Abstract: The present invention relates to compounds selected from the group consisting of:(i) the compounds of the formula ##STR1## in which: R is a hydrogen atom, a group OH, a group OCH.sub.3 or a group CH.sub.2 OH,*C, in the case where R is not a hydrogen atom, is an asymmetric carbon atom of (R,S), (R) or (S) configuration, and**C is an asymmetric carbon atom of (R,S) or (R) configuration; and(ii) their addition salts.It further relates to the method of preparing these compounds, to their use in therapeutics and in the field of analysis, and to intermediates.
    Type: Grant
    Filed: October 10, 1996
    Date of Patent: March 16, 1999
    Assignee: Fournier Industrie Et Sante
    Inventors: Luc Lebreton, Patrice Renaut, Philippe Durand
  • Patent number: 5728852
    Abstract: A method for producing a monoalkanol amide comprising the steps of (a) treating an entire amount of fatty acid with a monoalkanol amine in an amount of 0.7 to 0.95 times by mole of the amount of the fatty acid and more than 70% and not more than 90% by weight of the entire amount of the monoalkanol amine to yield a mixture mainly containing a monoalkanol amide and an amido monoester; and (b) treating the mixture obtained in step (a) with the remaining portion of the monoalkanol amine, wherein the molar ratio of the entire amount of the monoalkanol amine to that of the fatty acid is 1.0 to 1.3.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: March 17, 1998
    Assignee: KAO Corporation
    Inventors: Kenichi Nishikawa, Kazuhito Miyoshi, Yukiko Oshima, Hiroyuki Imoto
  • Patent number: 5712414
    Abstract: The present invention relates to a process for the preparation of hydroxycarboxylic acid amides of the general formula (1): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, halogen, cyano, a linear or branched alkyl, alkenyl, alkynyl or alkoxy group having 1 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a cycloalkyl group having 6 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, R.sup.3 is hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms, R.sup.4 is hydrogen or a linear or branched alkyl group having 1 to 6 carbon atoms, or R.sup.3 and R.sup.4, together with the carbon atom to which they are attached, form a five- or six-membered cycloalkane ring, and n is an integer from 1 to 12, wherein an aniline of the general formula (2) ##STR2## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: July 10, 1996
    Date of Patent: January 27, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Dierdorf, Theodor Papenfuhs
  • Patent number: 5587498
    Abstract: A method for amidation of carboxylic acids using a supported transition metal catalyst. The amides prepared by this inventive method are available in high-yield and excellent purity, without catalytic residue.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: December 24, 1996
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: James A. Krogh, Anita R. Mokadam, B. Brian Smith
  • Patent number: 5506362
    Abstract: An .alpha.-amino acid amide is prepared by reaction of an N.sup..alpha. -aryloxycarbonylamino acid with a compound containing a free amino group. This process makes it possible readily to prepare peptides, by direct reaction between the carboxyl group of the N.sup..alpha. -aryloxycarbonyl derivative of an amino acid and the free amino group of a second amino acid or of a peptide fragment, without requiring protection of the carboxyl function of the second amino acid or of the peptide fragment, nor a coupling agent nor a deprotection step.
    Type: Grant
    Filed: June 9, 1994
    Date of Patent: April 9, 1996
    Assignee: Solvay (Societe Anonyme)
    Inventors: Roland Callens, Georges Blondeel
  • Patent number: 5461176
    Abstract: This invention relates to bis-naphthalimides, including 2,2'-[1,2-ethanediylbis[imino(1-methyl-2,1-ethanediyl)]]-bis[5-nitro-1H-be nz[de]isoquinoline-1,3(2H)-dione] and 2,2'-[1,2-ethanediylbis[imino(2-methyl-2,1-ethanediyl)]]-bis[5-nitro-1H-be nz[de]isoquinoline-1,3(2H)-dione], processes for their preparation, pharmaceutical compositions containing them, and methods of using them to treat cancer in mammals.
    Type: Grant
    Filed: May 26, 1994
    Date of Patent: October 24, 1995
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventors: Jung-Hui Sun, Jose R. Matos, Chung-Ho Park, Robert G. Clifton, Jr.
  • Patent number: 5391826
    Abstract: Diamidopolyamines are prepared by reacting glutamic acid with two moles, per mole of glutamic acid, of a defined class of diamines, including oxyethyelene diamines, oxypropylenediamines, oxyethylene/propylene diamines, oxypropylene triamines, 1,2-diaminocyclohexane and isophorone diamine, whereby each of the carboxyl groups of the glutamic acid will react with an amine group of the amine reactant to thereby provide primary amine terminated amidopolyamines containing, internally, the unreacted primary amine group of the glutamic acid.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: February 21, 1995
    Assignee: Huntsman Corporation
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5329048
    Abstract: This invention relates to bis-naphthalimides, including 2,2'-[1,2-ethanediylbis[imino(1-methy1-2,1-ethanediyl)]]-bis[5-nitro-1H-be nz[de]isoquinoline-1,3(2H)-dione] and 2,2'-[1,2-ethanediylbis[imino(2-methyl-2,1-ethanediyl)]]-bis[5-nitro-1H-be nz[de]isoquinoline-1,3(2H)-dione], processes for their preparation, pharmaceutical compositions containing them, and methods of using them to treat cancer in mammals.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: July 12, 1994
    Assignee: The DuPont Merck Pharmaceutical Company
    Inventor: Jung-Hui Sun
  • Patent number: 5220063
    Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: June 15, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
  • 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: 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: 5103056
    Abstract: Disclosed is a method for selective formation of amidoamines which comprises reacting a carboxylic acid group, such as, for example, a diacid or an aliphatic acid terminated amide with an aminopropylated disecondary amine which contains a secondary amine terminus in the same molecule at a temperature of about 150.degree. C. to about 260.degree.0 C.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: April 7, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Donald H. Champion
  • Patent number: 5091572
    Abstract: Liquid amine terminated polyamide addition products having an average molecular weight of about 3,000 to about 10,000 are prepared by the non-catalytic reaction of a dicarboxylic acid having a molecular weight within the range of about 130 to about 700 with a higher molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 1,500 to about 6,000 and with a lower molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 200 to about 700, the reaction conditions including a temperature within the range of about 150.degree. to about 280.degree. C., a pressure of about 0.1 to 20 atmospheres and a reaction time of about 2 to about 5 hours.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: February 25, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Wei-Yang Su
  • Patent number: 4906394
    Abstract: C.sub.5 -C.sub.9 lactone based adduct materials are made by reacting a C.sub.5 -C.sub.9 lactone with a polyamine, a polyol or an amino alcohol to form a lactone adduct intermediate, and thereafter reacting the intermediate with an aliphatic hydrocarbyl saturated or unsaturated, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about one to about 165 total carbon atoms in said straight or branched chain to insure that the resulting lactone adduct is hydrocarbon soluble. The resulting adduct material are useful per se, as oil soluble dispersant additives, and are useful in fuel and lubricating oil compositions including concentrates containing the additives.
    Type: Grant
    Filed: October 7, 1986
    Date of Patent: March 6, 1990
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Antonio Gutierrez, Robert D. Lundberg
  • Patent number: 4869728
    Abstract: A motor fuel composition which inhibits engine ORI comprises a mixture of hydrocarbons boiling in the range of 90.degree. F.-450.degree. F. and the reaction product of one or more substituted or unsubstituted aliphatic carboxylic acids, including acyl-containing aliphatic carboxylic acids, and a polyoxyalkylene diamine.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: September 26, 1989
    Assignee: Texaco Inc.
    Inventor: Rodney L. Sung
  • Patent number: 4682982
    Abstract: N-higher alk(en)yl neoalkanamides are new compounds which unlike many other amides, are oily at washing temperatures, in the 10.degree. to 90.degree. C. range, and are capable of being adsorbed from wash and rinse waters by fibrous materials, such as laundry of synthetic, e.g., polyester, fabrics, which laundry is susceptible to being electrostatically charged, and decrease any electrostatic charge or inhibit accumulation thereof on such materials. Such neoalkanamides, e.g., N-coco-alkyl neodecanamide, can be incorporated in detergent compositions and in compositions for addition to laundry rinse waters, and in some instances it may be desirable for bentonite powder or agglomerate to also be included in such compositions to contribute fabric softening and other useful physical properties. Washing and rinsing operations are described in which N-higher alk(en)yl neoalkanamide is present in the waters, with and without supplementing small proportions of quaternary ammonium salt.
    Type: Grant
    Filed: March 27, 1985
    Date of Patent: July 28, 1987
    Assignee: Colgate-Palmolive Company
    Inventors: Robert J. Steltenkamp, Michael A. Camara
  • 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: 4655972
    Abstract: Carbonamides are prepared from carboxylic acids and ammonia in the presence of a catalytic amount of a hydrated oxide.Preferably a hydrated titanium-, zirconium- or tin oxide in an amount between 0.05 to 10% by weight is used. The hydrated oxide contains at least 4% of water.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: April 7, 1987
    Assignee: Internationale Octrooi Maatschappij "Octropa" B.V.
    Inventors: Teunis Eikelboom, John A. Rand, Pieter M. van Dijk
  • Patent number: 4640787
    Abstract: Certain branched chain amines and carboxylic derivatives thereof are useful additives for lubricants and fuels.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: February 3, 1987
    Assignee: Phillips Petroleum Company
    Inventor: Alexander D. Schuettenberg
  • Patent number: 4600520
    Abstract: Borated adducts of alkyl diamines and alkoxides impart effective multifunctional friction reducing and high temperature stabilizing characteristics to compositions comprising hydrocarbyl lubricants and fuels.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: July 15, 1986
    Assignee: Mobil Oil Corporation
    Inventor: Andrew G. Horodysky
  • Patent number: 4582933
    Abstract: This invention describes a process for the production of N-(tert-aminoalkyl)acrylamides by the reaction of acrylic acid with a suitable tertiary aminoalkylamine at a temperature of 150.degree.-230.degree. C. The aminoalkylamine and acrylic acid are reacted in equimolar quantities, preferably in the presence of an acidic or a basic catalyst.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: April 15, 1986
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventors: Richard Mertens, Kurt Dahmen
  • Patent number: 4552699
    Abstract: A process for the preparation of 3-acylaminoanilines of the general formula (1) ##STR1## in which R denotes a branched or unbranched alkyl radical having 1-7 carbon atoms or the phenyl group, which can be substituted by 1-2 methyl groups or by 1-2 chlorine atoms, which comprises reacting a carboxylic acid of the general formula (2)R--COOH (2)in which R has the meaning mentioned, with an excess of 1,3-diaminobenzene, and separating the reaction mixture by distillation.
    Type: Grant
    Filed: December 13, 1983
    Date of Patent: November 12, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhard Hahnle, Theodor Grewer
  • Patent number: 4549975
    Abstract: Borated adducts of alkyl diamines, alkoxides and lower carboxylic acids impart effective multifunctional friction reducing and high temperature stabilizing characteristics to compositions comprising hydrocarbyl lubricants and fuels.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: October 29, 1985
    Assignee: Mobil Oil Corporation
    Inventor: Andrew G. Horodysky
  • Patent number: 4529529
    Abstract: Borated hydrocarbylenetriamine amides can be made by borating the appropriate reaction product of a triamine and an organic monocarboxylic acid. They demonstrate friction reducing and/or fuel consumption reducing properties when formulated into lubricants, particularly lubricating oils, and fuels.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: July 16, 1985
    Assignee: Mobil Oil Corporation
    Inventor: Andrew G. Horodysky