Amidation Patents (Class 554/69)
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Patent number: 5571934Abstract: Process for preparing solutions of polyhydroxy-fatty acid amides having good color qualityIn the process described, at least one sulfur compound from the group of dithionous acid is added in an active amount to the crude solutions, which are in general more or less brown in color, after which water-clear polyhydroxy-fatty acid amide products result.Type: GrantFiled: August 1, 1995Date of Patent: November 5, 1996Assignee: Hoechst AGInventors: Bernd Papenfuhs, Reinhard Vybiral
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Patent number: 5565590Abstract: This invention relates to a process for recycling waste material selected from amino-carboxylic acid oligomers or polymers and amido-carboxylic acid oligomers or polymers into amido-carboxylic acids. A mixture containing water, an oligomeric or polymeric waste material, and a carboxylic acid is heated. The mixture is cooled to obtain a two phase system containing an aqueous phase and an organic phase which are separated. Carboxylic acids, unreacted starting materials, and the monomeric amido-carboxylic acid product are distilled from the organic phase. The remaining solid residue composed of high boiling oligomeric amino-carboxylic acids is recycled into Step (A).Type: GrantFiled: November 7, 1994Date of Patent: October 15, 1996Assignee: Eastman Chemical CompanyInventors: George C. Zima, Gary P. Lutz, Gary W. McChesney, T. Hugh Williams
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Patent number: 5539134Abstract: The preparation von N-alkanoyl-polyhydroxyalkylamines I in which ##STR1## in which Z stands for the polyhydroxyalkyl radical of a monosaccharide or oligosaccharide,R.sup.1 denotes hydrogen or C.sub.1 -C.sub.8 alkyl andR.sup.2 denotes C.sub.1 -C.sub.21 alkyl, by the reaction of polyhydroxyalkylamines of the general formula IIZ--NH--R.sup.1 (II),with alkyl carboxylates of the general formula III ##STR2## in which R.sup.3 denotes a C.sub.1 -C.sub.4 alkyl radical,in the presence of a basic catalyst, in which(a) all of the ester III is placed in the reactor and is heated to the reaction temperature, and the amine II is metered in in the form of a melt while the reaction proceeds, while alcohol R.sup.3 --OH formed is continuously removed by distillation,(b) the reaction is carried out at a temperature of from 55.degree. to 110.degree. C., and(c) the reaction is carried out in the absence of organic solvents.Type: GrantFiled: April 24, 1995Date of Patent: July 23, 1996Assignee: BASF AktiengesellschaftInventors: Beate Strecker, Helmut Wolf, Gerhard Wolf, Alfred Oftring, Hans-Heinrich Bechtolsheimer, Dieter Hertel
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Patent number: 5534642Abstract: Chemical synthesis of amido acids, and their conversion to amido acid phenyl ester sulfates for use as bleach activators, starting from carboxylic acids and lactams.Type: GrantFiled: February 23, 1995Date of Patent: July 9, 1996Assignee: The Procter & Gamble CompanyInventors: Stephen W. Heinzman, Jeffrey S. Dupont, William C. Tettenhorst
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Patent number: 5523431Abstract: The present application relates to a method of producing an amide product mixture having a low content of secondary amines by reacting an amide product mixture having a high secondary amine content with an aliphatic alkylene oxide in the absence of an essential amount of any alkoxylation catalyst. The amide product mixture obtained contains a minor amount of tertiary amines and exhibits advantageous properties when used for the formulation of cosmetic products, such as shampoos and creams; foam cleaning compositions, e.g. for textiles and cars; and functional fluids, such as lubricants, metal working fluids and hydraulic fluids.Type: GrantFiled: October 29, 1993Date of Patent: June 4, 1996Assignees: Berol Nobel AB, Castrol Ltd.Inventor: Rolf Skold
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Patent number: 5508454Abstract: The present invention relates to novel quaternary ammonium derivatives wh have properties similar to those of non-ionic, amphoteric and cationic surfactants, to their preparation and to their use as surfactants in foaming and emulsifying compositions intended for use in the fields of pharmaceutics, cosmetics, hygiene and detergency.These derivatives have the general formula ##STR1## wherein essentially R is an alkyl or alkenyl radical having from 5 to 29 carbon atoms, R.sub.1 and R.sub.2 are an alkyl radical having from 1 to 4 carbon atoms, R.sub.3 is a 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, methyl or 2,3,4,5,6-pentahydroxyhexyl radical and X is a halogen atom or a hydroxyl group.Type: GrantFiled: August 4, 1994Date of Patent: April 16, 1996Assignee: Societe d'Exploitation de Produits pour les Industries Chimiques -SEPPICInventors: Bernard Brancq, Jean-Pierre Boiteux
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Patent number: 5504228Abstract: The invention relates to new acylamino acids obtained by acylation of hydrolysates of proteins containing, essentially, fibroin and sericin as, for instance, silk.The invention provides also various compositions containing the said acylamino acids, for use in the cosmetic, hygienic, therapeutic and agricultural fields.Type: GrantFiled: December 7, 1993Date of Patent: April 2, 1996Assignee: Laboratoires PhytocosInventors: Jean Morelle, Eliane Lauzanne, Jacqueline Rothfuss
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Patent number: 5498786Abstract: This invention relates to novel processes for synthesizing intermediates in the preparation of N-aryl and N-heteroarylamide inhibitors of the enzyme acyl coenzyme A: cholesterol acyltransferase (ACAT), and to novel intermediates used in such processes.Type: GrantFiled: September 13, 1993Date of Patent: March 12, 1996Assignee: Pfizer Inc.Inventors: Sarah E. Kelly, George Chang
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Patent number: 5496959Abstract: This invention relates to the preparation of N-acyl taurates by the direct condensation of carboxylic acids with taurate (substituted 2-aminoalkane sulfonic acids and their alkali metal salts) derivatives.Type: GrantFiled: May 23, 1994Date of Patent: March 5, 1996Assignee: Hoechst Celanese CorporationInventor: James F. Day
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Patent number: 5470992Abstract: A method for the synthesis of betaines of the general formula ##STR1## by quaternizing the fatty acid amide dialkylamines of the general formula ##STR2## with .omega.-halogenalkylcarboxylic acids of the formula X-(CH.sub.2).sub.y COOH, wherein X is a halogen group, or their salts in aqueous solution, the reaction being carried out within a temperature range of 115.degree. to 180.degree. C., until organically bound chlorine can no longer be detected, the fatty acid amide dialkylamine optionally being quaternized partially or completely in a first step at 80.degree. to 100.degree. C.Type: GrantFiled: March 14, 1994Date of Patent: November 28, 1995Assignee: Th. Goldschmidt AGInventors: Burghard Gruning, Willi Foitzik, Christian Weitemeyer, Hans-Dieter Kaseborn
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Patent number: 5434276Abstract: A process for the preparation of an N-acyl tauride comprising reacting an aliphatic or alicyclic carboxylic acid having from 6 to 22 carbon atoms with a taurine salt having the formula:HNR.sub.1 --CHR.sub.2 --CHR.sub.3 --SO.sub.3 Mwherein R.sub.1 is H or a C.sub.1 to C.sub.20 hydrocarbon radical; R.sub.2 and R.sub.3 are each independently H, or C.sub.1 -C.sub.6 hydrocarbon radical; M is a salt forming radical selected from the group consisting of alkali metals and alkaline earth metals; in a substantially inert atmosphere in the presence of an alkali metal borohydride, wherein the alkali metal is selected from the group of sodium, potassium, lithium and ammonium to produce a reaction product containing N-acyl tauride.Type: GrantFiled: December 27, 1993Date of Patent: July 18, 1995Assignee: Finetex, Inc.Inventors: Ismail I. Walele, Samad A. Syed
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Patent number: 5414099Abstract: Chemical synthesis of amido acids, and their conversion to amido acid phenyl ester sulfates for use as bleach activators, starting from carboxylic acids and lactams.Type: GrantFiled: September 14, 1993Date of Patent: May 9, 1995Assignee: The Procter & Gamble CompanyInventors: Stephen W. Heinzman, Jeffrey S. Dupont, William C. Tettenhorst
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Patent number: 5393901Abstract: This invention relates to a process for preparing amido-carboxylic acids in water wherein hydrolysis and amidation reactions are conducted simultaneously in a single vessel. The process involves three steps. The first step involves heating at a temperature of 150.degree. C.-300.degree. C. for 2 to 10 hours, a mixture containing water, a nitrogen containing compound selected from the group consisting of a lactam and an amino acid, and a carboxylic acid or ester. The second step involves cooling the reaction mixture to obtain a two phase system containing an aqueous layer and an organic layer. The third step involves separating the amido-carboxylic acid containing organic layer from the aqueous layer. The presence of water aids in product isolation by phase separation and recycle of the reactants.Amido-carboxylic acids are used to make bleach activators for detergents.Type: GrantFiled: April 15, 1994Date of Patent: February 28, 1995Assignee: Eastman Chemical CompanyInventors: George C. Zima, T. Hugh Williams, Gary P. Lutz, William C. Dickason
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Patent number: 5393902Abstract: A process is reported for the preparation of bis(amidocarboxylic acid) involving reacting an ester with an aminocarboxylate compound, the latter being formed from lactams or aminocarboxylic acids and salts thereof. The ester and aminocarboxylate compound are present in a weight ratio of about 1:1 to about 1:4, and reaction is conducted in a mono- or polyhydric alcohol solvent.Type: GrantFiled: April 26, 1994Date of Patent: February 28, 1995Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Janet L. Coope, AnneMarie Brescia, Michael I. Hill, Martina Santoso, Stephen A. Madison
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Patent number: 5391780Abstract: This invention relates to a process for preparing amido-carboxylic acids in water. The process involves four steps. Step (A) involves hydrolyzing a lactam at a temperature of 150.degree. C.-300.degree. C. to form a mixture containing an amino acid. Step (B) involves cooling the reaction mixture formed in Step (A) to a temperature of 25.degree. C.-100.degree. C. Step (C) involves reacting a carboxylic acid anhydride with the amino acid formed in Step (A) to form a reaction mixture containing an organic layer which contains an amido-carboxylic acid and an aqueous layer. Step (D) involves separating the amido-carboxylic acid containing organic layer from the aqueous layer. The presence of water aids in product isolation by phase separation and recycle of the reactants. Amido-carboxylic acids are used to make bleach activators for detergents.Type: GrantFiled: April 15, 1994Date of Patent: February 21, 1995Assignee: Eastman Chemical CompanyInventors: George C. Zima, T. Hugh Williams
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Patent number: 5380891Abstract: Disclosed is a process for manufacturing a linear glucamide surfactant comprising reacting an N-alkylglucamine, e.g., N-methylglucamine, a fatty ester, e.g., coconut oil in the presence of a phase transfer agent, generally a nonionic surfactant, preferably a preformed product of the process, the reaction preferably being conducted in the presence of an alkaline catalyst.Type: GrantFiled: June 11, 1993Date of Patent: January 10, 1995Assignee: The Procter & Gamble CompanyInventors: Daniel S. Connor, Jeffrey J. Scheibel, Ju-Nan Kao
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Patent number: 5371252Abstract: A compound of the formula:R--NHCOOCH(CH.sub.2 OCH.sub.2 CHOHCH.sub.2 OH).sub.2 (I)wherein R is a C.sub.10 -C.sub.20 alkyl, optionally unsaturated, is employed in the preparation of wax microdispersions useful particularly in cosmetic composition for the hair.Type: GrantFiled: November 10, 1992Date of Patent: December 6, 1994Assignee: L'OrealInventors: Alexandre Zysman, Henri Sebag
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Patent number: 5371250Abstract: The process described relates to the preparation of aqueous betaine solutions by reaction of a tertiary amine with an .omega.-monohalocarboxylic acid, preferably monochloroacetic acid, and an alkali metal hydroxide in the presence of water, which solutions are said to be highly pure particularly in respect of the tertiary starting amine and .omega.-monohalocarboxylic acid. This is achieved by first reacting the three reaction components in a certain molar ratio with the aim of obtaining a betaine solution which comprises only a tolerated amount of starting amine. This aqueous betaine solution is then treated with a sulfonating agent, preferably with an alkali metal sulfite, alkali metal pyrosulfite or alkali metal bisulfite, for conversion of the .omega.-monohalocarboxylic acid present into the corresponding sulfocarboxylic acid, which is not troublesome. The process described is simple to carry out and leads to the highly pure aqueous betaine solutions mentioned.Type: GrantFiled: September 13, 1993Date of Patent: December 6, 1994Assignee: Hoechst AktiengesellschaftInventors: Hubert Seitz, Reinhard Vybiral
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Patent number: 5354906Abstract: An aqueous liquid solution of a betaine of the following general formula is disclosed ##STR1## in which R is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture which, on the average, corresponds to coconut fatty acids, wherein the solution has a solids content of at least 40% by weight, a pH of 5 to 8 and an aminoamide content of not more than 1% by weight, characterized by a content of 1 to 3% by weight, based on the solution, of one or more saturated fatty acids with, on the average, 8 to 18 carbon atoms or one or more unsaturated fatty acids with, on the average, 8 to 24 carbon atoms and 0 to 4% by weight of glycerin, based on the solution.Type: GrantFiled: February 12, 1993Date of Patent: October 11, 1994Assignee: Th. Goldschmidt AGInventors: Christian Weitemeyer, Willi Foitzik, Hans-Dieter Kaseborn, Burghard Gruning, Uwe Begoihn
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Patent number: 5348995Abstract: A novel amine-free antistatic agent comprising the reaction product of diethanolamine and a fatty acid or fatty acid ester, neutralized with a strong acid is disclosed, along with plastic composition treated with said antistatic composition, as well as a method for making the antistatic composition and methods for using it to produce plastic articles with antistatic properties.Type: GrantFiled: March 29, 1993Date of Patent: September 20, 1994Assignee: PPG Industries, Inc.Inventor: Barbara J. Anderson
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Patent number: 5318727Abstract: A cationic compound is useful for a cleaning agent such as shampooing and defined by the formula (I): ##STR1## in which R1 is straight or branched and an alkyl having 7 to 15 carbon atoms or an alkenyl having 7 to 15 carbon atoms; R2, R3 and R4, independently of one another, are an alkyl having 1 to 3 carbon atoms; G is hydrogen atom, an alkyl having 1 to 3 carbon atoms or a hydroxyalkyl having 1 to 3 carbon atoms, E is hydrogen atom, an alkyl having 1 to 3 carbon atoms, a hydroxyalkyl having 1 to 3 carbon atoms or an ammonium group having the formula (II): ##STR2## Y being hydrogen atom or hydroxy, A being hydroxy, a halogen atom or an alkylsulfate having 1 to 4 carbon atoms, m being 2 or 3, n being zero or an integer of 1 to 5, provided that (1) when G is an alkyl or a hydroxyalkyl, E is neither an alkyl nor a hydroxyalkyl, (2) when n is 1, Y is hydrogen atom or hydroxy and when n is zero, 2, 3, 4 or 5, Y is hydrogen atom and (3) G and E cannot both be hydrogen.Type: GrantFiled: August 14, 1991Date of Patent: June 7, 1994Assignee: Kao CorporationInventors: Yasuki Ohtawa, Makoto Kubo, Hiroyuki Imoto, Takashi Matsuo, Kazuyuki Yahagi, Koshiro Sotoya
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Patent number: 5312933Abstract: The present invention relates to a process of producing symmetrically structured difatty acid diamines by reacting mixtures of fatty acids or their esters with diamines, isolating the symmetrical difatty acid diamides from the reaction mixture by making use of their different solubilities and concentrating them by recrystallisation if necessary. The invention also provides for a process of isolating a fatty acid from a mixture of fatty acids wherein the difatty acid diamides produced in the process of the invention are saponified to yield the corresponding free fatty acid.Type: GrantFiled: February 28, 1991Date of Patent: May 17, 1994Assignee: Battelle-Institut e.V.Inventors: Rainer Frische, Jurgen Volkheimer, Klaus Wollmann, Herrmann Schomann, Judith Schneider, Alexander Ach, Renate Gross-Lannert, Bernd Best
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Patent number: 5310959Abstract: Processes for preparing 5,8,11-eicosatriynoic acid as well as esters and amides thereof involves initially preparing the acid by reacting 1-decyne with 1,4-dihalo-2-butyne in the presence of a strong base to form 1-halo-2,5-tetradecadiyne which is then reacted with 5-hexynoic acid so as to form 5,8,11-eicosatriynoic acid. This acid can then be converted to the acid chloride form and reacted with an alcohol to form an ester or converted to a potassium salt and reacted with a halide also to form an ester, or after conversion to an acid chloride reacted with an amine in the presence of a tertiary amine to form an amide, or the acid can be reacted with carbonyldiimidazole in the presence of a solvent and excess amine to form an amide.Type: GrantFiled: May 17, 1993Date of Patent: May 10, 1994Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Serge Restle, Michel Colin
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Patent number: 5298636Abstract: Polyhydroxy amines reacted with fatty acid esters yield polyhydroxy fatty acid amide surfactants, such as the C.sub.11 -C.sub.17 fatty N-methyl glucamides, which may be contaminated with secondary amines. Such amines are acylated by a reaction with acetic anhydride. The resulting "clean" polyhydroxy fatty acid amide surfactants are preferred for use in the presence of oxidants, especially in the formulation of modern, colorless liquid detergents.Type: GrantFiled: September 23, 1992Date of Patent: March 29, 1994Assignee: The Procter & Gamble CompanyInventors: Daniel S. Connor, Mark Hsiang-Kuen Mao
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Patent number: 5239095Abstract: A method is disclosed for the preparation of flowable, aqueous dispersions, which contain 10 to 30% by weight of betaines of the general formula ##STR1## wherein R.sup.1 is a linear alkyl group with at least 16 carbon atoms or the R.sup.4 CONH(CH.sub.2).sub.x -- group, in which R.sup.4 CO is an acyl group derived from a saturated, linear fatty acid with at least 16 carbon atoms and x=2 or 3,R.sup.2, R.sup.3 are the same or different and in each case represent an alkyl group with 1 to 4 carbon atoms,y is 1, 2 or 3,by quaternizing a tertiary amine of the general formulaR.sup.1 --NR.sup.2 R.sup.3with .omega.-halogenalkylcarboxylic acids X(CH.sub.2).sub.y COOY or their salts (X=halogen group, Y=hydrogen, alkali or ammonium) in an aqueous or alcoholic, aqueous solution at elevated temperature. Anionic surfactants are added to the reaction mixture before the quaternization reaction in such amounts, that the ultimate dispersion contains 1 to 10% by weight of anionic surfactants.Type: GrantFiled: October 31, 1991Date of Patent: August 24, 1993Assignee: Th. Goldschmidt AGInventor: Volkbert Bade
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Patent number: 5210227Abstract: Compounds of formula I, ##STR1## wherein R.sup.1 represents H, OH, protected OH or alkoxy; R.sup.2 represents H; R.sup.3 represents O or (H,OH); R.sup.4 represents methyl, ethyl, propyl or allyl; R.sup.5 represents OH, protected OH or alkoxy; R.sup.6 represents OH; R.sup.7 represents OH, alkoxy or NR.sup.8 R.sup.9 where R.sup.8 and R.sup.9 independently represent H, alkyl or aryl; in addition, R.sup.1 and R.sup.2 may together represent a second bond between the carbon atoms to which they are attached; and R.sup.6 and R.sup.7 may together represent O; and pharmaceutically acceptable salts thereof; are useful inter alia as immunosuppressive agents. The invention also provides the novel compounds of formula I.Type: GrantFiled: February 27, 1991Date of Patent: May 11, 1993Assignees: Fisons plc, Fujisawa Pharmaceutical Company LimitedInventors: Hirokazu Tanaka, Martin E. Cooper, David K. Donald
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Patent number: 5210207Abstract: The invention provides an improved process for the preparation of a vinyl derivative of a Bronsted acid, wherein a vinyl derivative of a first Bronsted acid is subjected to transvinylation by reactive distillation with a second Bronsted acid.Type: GrantFiled: January 31, 1991Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Morteza Mokhtarzadeh, Rex E. Murray
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Patent number: 5208355Abstract: Novel amide derivatives have the following structure (1): ##STR1## where Y is hydrogen or an unsaturated fatty acid residue,A is an hydroxyalkyl group,B is a sugar or phosphate residue, and(C.sub.a H.sub.b) is a hydrocarbon residue with from 7 to 49 carbon atoms.The amide derivative can be employed in compositions, together with a suitable carrier, for topical application, particularly to improve damaged human skin or hair.Type: GrantFiled: May 1, 1991Date of Patent: May 4, 1993Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.Inventor: Ian R. Scott
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Patent number: 5110508Abstract: The invention relates to a process, more especially a discontinuous process, for conducting a reaction taking place at elevated temperature in which heat-sensitive products are formed. To increase the volume-time yield, a heat transfer unit independent of the reactor is used for heating. The invention also relates to an apparatus for the production of heat-sensitive products at elevated temperatures. This apparatus comprises a reactor and a heating system. To increase the volume-time yield, the heating system comprises at least one heat transfer unit arranged outside and connected to the reactor.Type: GrantFiled: April 20, 1989Date of Patent: May 5, 1992Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karl-Heinz Buettgen, Bernhard Gutsche, Friedrich Hommers, Wilhelm Johannisbauer, Eberhard Peukert, Reinhold Sedelies
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Patent number: 5103055Abstract: Disclosed is a method which comprises the reaction in a reaction zone of a nitrile, RCN, with a hydroxyl compound, R'OH, in the presence of water introduced into the reaction zone in the amount of more than 0.15 mole and up to 10 moles, per mole of RCN introduced to the reaction zone, thereby producing a reaction mixture containing at least one amide selected from R--CONHR' and R--CON(R').sub.Type: GrantFiled: May 10, 1990Date of Patent: April 7, 1992Assignee: The Standard Oil CompanyInventor: Mark C. Cesa