Purification Or Recovery Patents (Class 554/70)
  • 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
  • Patent number: 7312346
    Abstract: A method for purifying hydroxyalkyl amide of residual alkanolamine by using nonpolar solvent, an acidic pH, salt solutions and an elevated temperature.
    Type: Grant
    Filed: November 12, 2003
    Date of Patent: December 25, 2007
    Assignee: Crompton Corporation
    Inventors: Timothy L. Lambert, E. Brian Fox
  • Patent number: 6777213
    Abstract: A process for recovering carboxylic acids from an aqueous mixture such as a fermentation broth using a solvent containing at least one olefin without the need for first removing the spent microorganism cells is provided. A co-solvent which increases the partition coefficient of the solvent relative to the carboxylic acid may optionally be included. The resulting carboxylic acid is hydrogenated to produce a saturated carboxylic acid.
    Type: Grant
    Filed: August 13, 2003
    Date of Patent: August 17, 2004
    Assignee: Cognis Corporation
    Inventor: Michael D. Staley
  • Patent number: 6583095
    Abstract: The present invention relates to an improved process for synthesizing organic compounds for use as bleach activators.
    Type: Grant
    Filed: May 7, 2001
    Date of Patent: June 24, 2003
    Assignee: Procter & Gamble Company
    Inventors: Jeffrey Scott Dupont, Robert Richard Dykstra
  • Patent number: 6500973
    Abstract: A process for the purification and isolation of a chemical compound, by extractive solution crystallization. The process comprises combining in any order a first solvent, a second solvent, and a mixture comprising a chemical compound with at least one impurity. The second solvent phase extracts impurities out of the first solvent, and keeps the impurities dissolved to avoid their co-crystallization with the phenyl ester salt. Once the chemical compound has crystallized out of solution, it is collected, washed and/or dried. The second solvent may be added after the mixture containing at least one chemical compound is dissolved in a first solvent, as long as the second solvent phase is added prior to the end of crystallization. Advantageously, this invention combines the previously distinct steps of extraction and crystallization in one unit operation.
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: December 31, 2002
    Assignee: Eastman Chemical Company
    Inventor: Kevin J. Fontenot
  • Patent number: 6369250
    Abstract: The present invention relates to a process for the preparation of a purified salt of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate. The process comprises the steps of: (a) providing a source of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate; (b) admixing the source with a water-based purification system to form a purification mixture, the water-based purification system having water present at a ratio of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate to water ranging from about 1:0.05 to about 1:50, preferably from about 1:0.1 to about 1:40; (c) separating a purified salt of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate from the purification mixture; and (d) collecting said purified salt of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate. In preferred embodiments, the purification mixture includes a processin aide such as ethyl alcohol, propyl alcohol, isopropyl alcohol, acetone and mixtures thereof.
    Type: Grant
    Filed: February 17, 2000
    Date of Patent: April 9, 2002
    Assignee: Procter & Gamble Company
    Inventors: Robert Richard Dykstra, Jeffrey Scott Dupont, Michael Eugene Burns
  • 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: 6034257
    Abstract: In a process for preparing an alkoxylated amide of the formula (I)R.sup.1 --CO--NR.sup.2 --CHR.sup.3 --CHR.sup.4 --O--(CHR.sup.5 --CHR.sup.6 --O).sub.n --H (I)(1) glycerides of the fatty acids, specified later on, of the formula (II):R.sup.1 --COOH (II)are reached with amines of the formula (III)HNR.sup.2 R.sup.7 (III)to give amides of the formula (IV)R.sup.1 --CO--NR.sup.2 --R.sup.7 (IV)and glycerol,(2) then the glycerol which has been formed is separated off by adding of aqueous acid solution to the reaction mixture until it has a pH in the range 1-7, in order to bring about phase separation into a glycerol-containing aqueous phase and an organic phase containing amides of the formula (IV), and separating off the aqueous phase, and(3) subsequently the amide of the formula (IV) is reacted with ethylene oxide and/or propylene oxide and/or butylene oxide to give alkoxylated amides of the formula (I).
    Type: Grant
    Filed: June 3, 1999
    Date of Patent: March 7, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Oftring, Gunter Oetter, Richard Baur, Oliver Borzyk, Bernd Burkhart, Christian Ott, Martin aus dem Kahmen
  • Patent number: 6008390
    Abstract: N-long-chain acyl acidic amino acids or salts thereof are prepared by condensing an acidic amino acid or a salt thereof and a C.sub.8 -C.sub.22 long-chain fatty acid chloride in an aqueous solvent with stirring at a stirring power of not less than 0.2 kW/m.sup.3 while keeping the pH in the range of 10-13.
    Type: Grant
    Filed: September 8, 1997
    Date of Patent: December 28, 1999
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tatsuya Hattori, Kiyomiki Hirai
  • Patent number: 5962709
    Abstract: Process for the aftertreatment of betaine and amphoteric surfactants comprising adjusting the pH to the range of from 11 to 14 by addition of an alkali metal hydroxide, followed by a thermal aftertreatment if the surfactant contains dichloroacetic acid residues.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: October 5, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien (KGaA)
    Inventors: Gunter Uphues, Uwe Ploog, Rainer Jeschke, Renate Schick
  • Patent number: 5723673
    Abstract: N-alkyl polyhydroxy alkyl amines such as N-methyl glucamine having a Gardner Color of less than 1 are reacted with sources of fatty acyl groups such as methyl esters, anhydrides, and/or fatty acids that have greater than 98% transmittance at 460 nm in organic hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amine amides with good color. The N-alkyl polyhydroxyamines can be purified by crystallization, and/or subjected to reductive bleaching, to provide superior color. The reaction is preferably carried out at low temperature for short periods of time and with low catalyst levels to minimize formation of cyclic products. The resulting amide product can be further purified by treatment with anionic and cationic exchange resins to remove soap and amine impurities. The anionic ion exchange resin can be readily regenerated by acidifying it followed by washing with an organic solvent.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 3, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Junan Kao, Ephraim Lamar Kelly, Vicki Lynn Weber, Michael Steven Gibson, Donald Benjamin Appleby, Joseph Fredrich Sherman, Ronald Edward Pegoli, Mary Celine Schneider, Terry Franklin Formyduval, Larry Nelson Hawkins
  • Patent number: 5646318
    Abstract: A process is provided for producing a hydroxyalkylamide which comprises reacting alkyl ester and alkanolamine in the presence of a catalyst to provide a reaction mixture containing hydroxyalkylamide product and low boiling alcohol by-product, solidifying the hydroxyalkylamide product, neutralizing the catalyst and recovering the hydroxyalkylamide product.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: July 8, 1997
    Assignee: Akzo Nobel nv
    Inventors: Maurice Dery, Nils Brolund
  • Patent number: 5571934
    Abstract: 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: Grant
    Filed: August 1, 1995
    Date of Patent: November 5, 1996
    Assignee: Hoechst AG
    Inventors: Bernd Papenfuhs, Reinhard Vybiral
  • Patent number: 5565590
    Abstract: 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: Grant
    Filed: November 7, 1994
    Date of Patent: October 15, 1996
    Assignee: Eastman Chemical Company
    Inventors: George C. Zima, Gary P. Lutz, Gary W. McChesney, T. Hugh Williams
  • Patent number: 5523431
    Abstract: 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: Grant
    Filed: October 29, 1993
    Date of Patent: June 4, 1996
    Assignees: Berol Nobel AB, Castrol Ltd.
    Inventor: Rolf Skold
  • Patent number: 5473088
    Abstract: A process for the direct neutralization of N-acyl sarcosines wherein all raw materials and products are in the liquid state up to the final crystallization of the product. The N-acyl sarcosines are neutralized in a continuous or batch mode with caustic such as aqueous hydroxide at elevated temperatures to produce a molten, free flowing liquid, which can then be crystallized to solid product.
    Type: Grant
    Filed: June 7, 1994
    Date of Patent: December 5, 1995
    Assignee: Hampshire Chemical Corp.
    Inventor: John M. Beland
  • Patent number: 5466840
    Abstract: This invention relates to a 5 step process for preparing a purified alkali metal salt of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate in one reaction vessel without isolation of intermediates. The steps are as follows: A) reacting an alkali metal salt of 4-hydroxybenzenesulfonic acid with a C.sub.2 to C.sub.4 carboxylic anhydride in a solvent to form an alkali metal salt of 4-acyloxybenzenesulfonic acid and a C.sub.2 to C.sub.4 carboxylic acid. B) adding an [(1-oxyalkanoyl)amino]alkanoic acid and a transesterification catalyst to the reaction product of step A) and heating at a temperature and pressure sufficient to maintain reflux of the solvent and to remove the C.sub.2 to C.sub.4 carboxylic acid from the reaction vessel to form a reaction mixture containing an alkali metal salt of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate. C) removing the solvent from the reaction mixture formed in step B).
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: November 14, 1995
    Assignee: Eastman Chemical Company
    Inventors: Gary P. Lutz, George C. Zima, Rex Bernard
  • Patent number: 5434276
    Abstract: 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: Grant
    Filed: December 27, 1993
    Date of Patent: July 18, 1995
    Assignee: Finetex, Inc.
    Inventors: Ismail I. Walele, Samad A. Syed
  • Patent number: 5419815
    Abstract: The present invention relates to a process for purifying fatty acid amides, which contains the following process steps:neutralization of the fatty acid by addition of an aqueous alkaline solution andsubsequent distillation of the neutralized mixture.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: May 30, 1995
    Assignee: Hoechst AG
    Inventors: Norbert Doerpinghaus, Siegbert Rittner
  • Patent number: 5393905
    Abstract: This invention relates to a four step process for purifying amido-carboxylic acids by liquid/liquid extraction from a reaction mixture containing an amido-carboxylic acid. The first step involves distilling impurities from a reaction mixture containing an amido-carboxylic acid to form a distillate residue. The second step involves mixing the distillate residue with a nonpolar hydrocarbon solvent wherein the mixture is maintained above the freezing point of the distillate residue. The third step involves allowing the hydrocarbon solvent and distillate residue to achieve phase separation of an organic phase containing the amido-carboxylic acid and an organic phase containing the nonpolar hydrocarbon solvent. The fourth step involves separating the organic phase containing the nonpolar hydrocarbon solvent from the organic phase containing the amido-carboxylic acid.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: February 28, 1995
    Assignee: Eastman Chemical Company
    Inventors: George C. Zima, T. Hugh Williams, Mark R. Shelton
  • Patent number: 5386043
    Abstract: A process for the non-aqueous neutralization of N-Acyl sarcosines. N-Acyl sarcosines are neutralized with anhydrous hydroxide or with hydroxide with low water content, ideally less than 20% water, using high shear. The process eliminates numerous stages previously required on route to a 100% active product. In addition, 30% solutions can be produced by the instant process, with the advantage of avoiding pH ranges at which gel phases or liquid crystals form.
    Type: Grant
    Filed: June 7, 1994
    Date of Patent: January 31, 1995
    Assignee: Hampshire Chemical Corp.
    Inventor: Joseph J. Crudden
  • Patent number: 5371250
    Abstract: 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: Grant
    Filed: September 13, 1993
    Date of Patent: December 6, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Seitz, Reinhard Vybiral
  • Patent number: 5298636
    Abstract: 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: Grant
    Filed: September 23, 1992
    Date of Patent: March 29, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Daniel S. Connor, Mark Hsiang-Kuen Mao