Hydrolyzing Fatty Material With Water Only Patents (Class 554/160)
  • Patent number: 12146110
    Abstract: A method for producing renewable diesel includes introducing a primary feedstock comprising biologically-derived triglycerides with catalyst poisons into a first reaction chamber and hydrolyzing the primary feedstock within the first reaction and liquid-liquid extraction chamber for at least an hour such that the reacted triglycerides are separated into an aqueous solution comprising glycerol and catalyst poisons, and an intermediate feedstock comprising free fatty acids and catalyst poisons. The method also includes distilling the intermediate feedstock to separate the intermediate feedstock into a purified intermediate stream and a lower volume bottom stream containing unreacted triglyceride, diglyceride, monoglyceride, FFA and catalyst poisons. The method also includes combining the purified intermediate feedstock with a hydrogen stream and converting, in a second reaction chamber comprising a metallic catalyst bed, the purified intermediate feedstock into a product comprising long-chain alkanes.
    Type: Grant
    Filed: August 24, 2023
    Date of Patent: November 19, 2024
    Assignee: Green Carbon Development, LLC
    Inventors: Thomas Bass, James Rolston, Terry Sparkman
  • Patent number: 11773332
    Abstract: A method for producing renewable diesel includes introducing a primary feedstock comprising biologically-derived triglycerides with catalyst poisons into a first reaction chamber and hydrolyzing the primary feedstock within the first reaction and liquid-liquid extraction chamber for at least an hour such that the reacted triglycerides are separated into an aqueous solution comprising glycerol and catalyst poisons, and an intermediate feedstock comprising free fatty acids and catalyst poisons. The method also includes distilling the intermediate feedstock to separate the intermediate feedstock into a purified intermediate stream and a lower volume bottom stream containing unreacted triglyceride, diglyceride, monoglyceride, FFA and catalyst poisons. The method also includes combining the purified intermediate feedstock with a hydrogen stream and converting, in a second reaction chamber comprising a metallic catalyst bed, the purified intermediate feedstock into a product comprising long-chain alkanes.
    Type: Grant
    Filed: July 1, 2022
    Date of Patent: October 3, 2023
    Assignee: Green Carbon Development, LLC
    Inventors: Thomas Bass, James Rolston, Terry Sparkman
  • Patent number: 11773347
    Abstract: Esterquats find major applications as fabric softeners. After Tallow fatty acids and Palm oil fatty acids, fatty acids from sustainable sources like Rice bran fatty acids (RBFA) are desired. RBFA is formed as a by-product during refining of Rice bran oil and hence it is contained in the non edible portion of the oil. The production of high quality esterquats from this by-product is challenging, but the invention describes a process to produce high quality esterquats having low odour and a low acid value. This enhances easy formulation of various products and better customer acceptance. Liquid esterquats produced from RBFA enable e.g. cold processing for fabric softener formulations.
    Type: Grant
    Filed: July 10, 2019
    Date of Patent: October 3, 2023
    Assignee: CLARIANT INTERNATIONAL LTD
    Inventors: Sushant Dattaram Wadekar, Prerak Rajendrakumar Contractor
  • Patent number: 11718795
    Abstract: A system and method for renewable diesel synthesis utilizes a triglyceride feedstock derived from biological sources. The first step involves hydrolysis of the triglycerides into an intermediate feedstock comprising a mixture of free fatty acids and glycerol (separated from the FFA by decantation and then distilled). The FFA is then further processed in a distillation step to produce a stream free of catalyst poisons and utilized as feedstock for hydrotreatment in a renewable diesel production process. By converting the initial triglyceride feedstock to an FFA feedstock, the need to hydrotreat at typical high temperature that promote the decarboxylation reaction is obviated, thereby reducing the production of CO2, generating a significantly higher proportion of saturated, long chain C14, C16 or C18 hydrocarbons (as opposed to short-chain carbons such as propane), and the more valuable glycerol product is secured.
    Type: Grant
    Filed: December 21, 2021
    Date of Patent: August 8, 2023
    Assignee: Green Carbon Development, LLC
    Inventors: Thomas Bass, James Rolston, Terry Sparkman
  • Patent number: 10961472
    Abstract: A bio-organic composition includes residues of a fatty acid glyceride-containing composition, residues of a first epoxide or glycol, and the residues of a second epoxide. The fatty acid glyceride-containing composition is characterized by the viscosity at room temperature. The first epoxide or glycol and second epoxides are present in a sufficient amount that the room temperature viscosity of the bio-organic composition is lower than the room temperature viscosity of the vegetable oil prior to formulation and/or the first epoxide or glycol and second epoxides are present in a sufficient amount that the pour point of the bio-organic composition is lower than the pour point of the fatty acid glyceride-containing composition prior to formulation.
    Type: Grant
    Filed: November 21, 2016
    Date of Patent: March 30, 2021
    Assignee: 21st Century R & D, LLC
    Inventor: John Rissio
  • Patent number: 9533934
    Abstract: The present invention concerns a process to carry out an ester hydrolysis wherein the ester compound (c) is made from at least an alcohol (a) and a carboxylic acid (b), and wherein said alcohol (a) and said carboxylic acid (b) are forming a biphasic liquid system when mixed together; comprising at least a step of producing an ester compound (c)/water emulsion by using as stabilizing species amphiphilic solid particles of nanometric dimension and optionally a catalyst X.
    Type: Grant
    Filed: April 11, 2014
    Date of Patent: January 3, 2017
    Assignees: RHODIA OPERATIONS, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ECOLE NORMALE SUPERIEURE DE LYON
    Inventors: Floryan DeCampo, Wenjuan Zhou, Zhaoyu Fan, Xiaoshuang Feng, Jean-Marc Clacens, Laurent Bonneviot, Guillaume Malcouronne
  • Patent number: 8835662
    Abstract: There is described a continuous process for the oxidative cleavage of vegetable oils containing triglycerides of unsaturated carboxylic acids, for the obtainment of saturated carboxylic acids, comprising the steps of: a) feeding to a first continuous reactor at least a vegetable oil, an oxidizing compound and a catalyst capable of catalyzing the oxidation reaction of the olefinic double bond to obtain an intermediate compound containing vicinal diols, and of b) feeding to a second continuous reactor said intermediate compound, a compound containing oxygen and a catalyst capable of catalyzing the oxidation reaction of the vicinal diols to carboxylic groups, to obtain saturated monocarboxylic acids (i) and triglycerides containing saturated carboxylic acids with more than one acid function (ii); c) separating the saturated monocarboxylic acids (i) from the triglycerides having more than one acid function (ii).
    Type: Grant
    Filed: December 29, 2010
    Date of Patent: September 16, 2014
    Assignee: Novamont S.p.A.
    Inventors: Arno Bieser, Giampietro Borsotti, Francesca Digioia, Adriano Ferrari, Alessandro Pirocco
  • Patent number: 8802876
    Abstract: An effective process for producing fatty acids catalyzed by double metal cyanide complex or a supported group VIb transition metal oxide, wherein the catalyst is stable and reusable.
    Type: Grant
    Filed: August 13, 2010
    Date of Patent: August 12, 2014
    Assignee: Council of Scientific and Industrial Research
    Inventors: Srinivas Darbha, Jitendra Kumar Satyarthi, Raja Thirumalaiswamy, Shilpa Shirish Deshpande
  • Patent number: 8530683
    Abstract: A method of obtaining a solid component rich in a petroselinic compound from the seed of a plant of the Apiaceae or Araliaceae families, the method comprising: (a) treating a portion of the seed of the plant with an extraction solvent; and (b) inducing formation of the solid component.
    Type: Grant
    Filed: December 22, 2008
    Date of Patent: September 10, 2013
    Assignee: Bangor University
    Inventors: Mark Stephen Baird, David Preskett
  • Publication number: 20120296073
    Abstract: A process of obtaining a saponin-rich component from a plant of the Araliaceae family, the process comprising the steps of: (a) treating a portion of the plant with an extraction solvent in which saponin-containing compounds are soluble; and (b) treating the portion of plant or the extract obtained therefrom to remove fatty acid residues from said portion of plant or extract thereof.
    Type: Application
    Filed: May 11, 2012
    Publication date: November 22, 2012
    Applicant: BANGOR UNIVERSITY
    Inventors: Mark Stephen Baird, David Preskett
  • Publication number: 20120215017
    Abstract: An effective process for producing fatty acids catalyzed by double metal cyanide complex or a supported group VIb transition metal oxide, wherein the catalyst is stable and reusable.
    Type: Application
    Filed: August 13, 2010
    Publication date: August 23, 2012
    Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Srinivas Darbha, Jitendra Kumar Satyarthi, Raja Thirumalaiswamy, Shilpa Shirish Deshpande
  • Patent number: 7767837
    Abstract: A method comprising contacting an alcohol, a feed comprising one or more glycerides and equal to or greater than 2 wt % of one or more free fatty acids, and a solid acid catalyst, a nanostructured polymer catalyst, or a sulfated zirconia catalyst in one or more reactors, and recovering from the one or more reactors an effluent comprising equal to or greater than about 75 wt % alkyl ester and equal to or less than about 5 wt % glyceride.
    Type: Grant
    Filed: May 4, 2007
    Date of Patent: August 3, 2010
    Assignee: TDA Research, Inc.
    Inventor: Brian Elliott
  • Publication number: 20100184168
    Abstract: A process for producing fatty acid by hydrolyzing oil and fat, which comprises: a first step of partially hydrolyzing oil and fat by either of the following method (a) or (b), and a second step of hydrolysis by the other method: (a) enzymatic hydrolysis using an immobilized enzyme which is an enzyme immobilized on a support and (b) high pressure and temperature hydrolysis. A method of efficiently producing fatty acid with a reduced content of trans-unsaturated fatty acid in the constituent fatty acids and having a good appearance with reduced coloring by hydrolysis of oil and fat is provided.
    Type: Application
    Filed: October 6, 2006
    Publication date: July 22, 2010
    Applicant: KAO CORPORATION
    Inventors: Minoru Kase, Toshiteru Komatsu
  • Patent number: 7691159
    Abstract: A triglyceride-to-fuel conversion process including the steps of (a) preconditioning unsaturated triglycerides by catalytic conjugation, cyclization, and cross-link steps; (b) contacting the modified triglycerides with hot-compressed water containing a catalyst, wherein cracking, hydrolysis, decarboxylation, dehydration, aromatization, or isomerization, or any combination thereof, of the modified triglycerides produce a crude hydrocarbon oil and an aqueous phase containing glycerol and lower molecular weight molecules, and (c) refining the crude hydrocarbon oil to produce various grades of biofuels.
    Type: Grant
    Filed: September 19, 2007
    Date of Patent: April 6, 2010
    Assignee: Applied Research Associates, Inc.
    Inventor: Lixiong Li
  • Patent number: 7642386
    Abstract: The invention relates to a process for producing an alcohol from fats and oils, including: step 1 of reacting starting fats and oils with water to produce a reaction product containing a glycerin unit, and step 2 of subjecting the reaction product obtained in step 1 to a hydrogenation reaction in the presence of a catalyst in the coexistence of water in an amount of 0.5 mole or more relative to 1 mole of the glycerin unit contained in the reaction product.
    Type: Grant
    Filed: March 7, 2006
    Date of Patent: January 5, 2010
    Assignee: Kao Corporation
    Inventors: Toru Sakamoto, Masanori Namba, Nobuhiro Tatsumi
  • Publication number: 20040267035
    Abstract: This invention relates to a method of hydrolyzing glycerol fatty acid ester-containing composition, such as a fat and/or an oil, to produce fatty acids having a low proportion of trans-isomer fatty acids. Specifically, the present invention relates to a process for the hydrolyzing the glycerol fatty acid ester-containing compositions under conditions resulting in a low proportion of trans-isomer fatty acids.
    Type: Application
    Filed: June 10, 2004
    Publication date: December 30, 2004
    Inventors: Paul D. Bloom, Inmok Lee, Peter Reimers
  • Patent number: 6646146
    Abstract: The present invention relates to a liquid phase process for the direct hydrolysis of a fatty acid ester to the corresponding fatty acid and alcohol in the presence of a catalyst, wherein the fatty acid in the liquid phase is contacted with steam in the presence of a compound of a metal that is capable of forming a soap with a large hydration shell as a catalyst.
    Type: Grant
    Filed: April 8, 2002
    Date of Patent: November 11, 2003
    Assignee: HaltermannAscot GmbH
    Inventors: Jacobus Sinnema, Luc De Graef, Thomas Meisel, Inge Mussler
  • Patent number: 6159523
    Abstract: Fish oil concentrates, having:.gtoreq.40% of long chain poly unsaturated fatty acids<20% of saturated fatty acids (C.sub.14 -C.sub.18)<15% oleic acid<12% C.sub.16:1 --fatty acidand with a weight-ratio:DHA=0.5-3.0EPAcan be obtained by a process involving the following stepssubjecting a fish oil to an enzymic conversionremoving free fatty acids or esters from conversion-productsubjecting product of above to enzymic hydrolysis, using 1.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: December 12, 2000
    Assignee: Loders-Croklaan BV
    Inventors: Frederick William Cain, Stephen Raymond Moore, Gerald Patrick McNeill
  • Patent number: 6020020
    Abstract: Fish oil concentrates, having:.ltoreq.40% of long chain poly unsaturated fatty acids<20% of saturated fatty acids (C.sub.14 -C.sub.18)<15% oleic acid<12% C.sub.16:1 -fatty acidand with a weight-ratio: ##EQU1## can be obtained by a process involving the following steps subjecting a fish oil to an enzymic conversionremoving free fatty acids or esters from conversion-productsubjecting product of above to enzymic hydrolysis, using specific lipase or partial glyceride-specific lipasewash and dry productre-esterify dried product.
    Type: Grant
    Filed: May 26, 1998
    Date of Patent: February 1, 2000
    Assignee: Loders-Croklaan B.V.
    Inventors: Frederick William Cain, Stephen Raymond Moore, Gerald Patrick McNeill
  • Patent number: 5917068
    Abstract: This invention relates to a process for removing sterols and phosphorous compounds from naturally occurring lipid mixtures. The process involves hydrolyzing a naturally occurring lipid mixture containing phospholipids, triglycerides, and sterols to form a two-phase product containing a fatty acid phase comprised of free fatty acids and sterols, and an aqueous phase comprised of water, glycerol, and glycerol phosphoric acid esters. The aqueous phase is separated from the fatty acid phase and the crude fatty acid phase is heated to convert the free sterols to fatty acid sterol esters. The free fatty acids are distilled from the fatty acid sterol esters to yield purified fatty acids which are free of cholesterol and other sterols, and phosphorous compounds.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: June 29, 1999
    Assignee: Eastman Chemical Company
    Inventors: Scott Donald Barnicki, Charles Edwan Sumner, Jr.
  • Patent number: 5917067
    Abstract: A process for producing an omega-functionalized aliphatic carboxylic acid starting from cyclohexanone and omega-functionalized .alpha.-olefins or acrylic esters. The process comprises an addition step, an oxidation step, an isomerization step, and one or more hydrogenation steps. The process allows to use raw materials that are available at low cost and to achieve high selectivity and high yield with industrially simple steps. The process includes the production of new intermediate products, including 2-oxepanone-7-substituted products.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: June 29, 1999
    Assignee: Industrie Chimiche Caffaro S.P.A.
    Inventors: Livius Cotarca, Paolo Maggioni, Alfonso Nardelli, Stefano Sguassero
  • Patent number: 5508455
    Abstract: The present invention relates to an improved process for preparing fatty acids from alkyl, preferably methyl esters via acid hydrolysis by using ratios of water/ester/acid catalyst to form single phase reaction mixtures wherein the initial stoichiometric ratio of water to ester is at least about 1:1. These ratios are represented by the ternary phase diagram of FIG. 1 for a preferred C.sub.6 -C.sub.14 alkylbenzene sulfonic acid catalyst having mid-point attachment of the alkyl chain to the benzene ring.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: April 16, 1996
    Assignee: The Procter & Gamble Company
    Inventor: Michael S. Gibson
  • Patent number: 5498733
    Abstract: Nylon-11 monomer, 11-aminoundecanoic acid, is synthesized from 12-oxododecanoic acid oxime in a three-step reaction sequence which involves a Beckmann rearrangement, Hofmann degradation and hydrolysis. The aldoxime acid is hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid. This amide is then treated with a solution of sodium methoxide and bromine at 70.degree.-80.degree. C. to give 11-(methoxycarbonylamino)undecanoic acid, which upon basic hydrolysis and subsequent neutralization, yields the 11-aminoundecanoic acid.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: March 12, 1996
    Assignee: Howard University
    Inventors: Folahan O. Ayorinde, Chukwuma P. Nwaonicha
  • Patent number: 5440061
    Abstract: The present invention relates to an improved process for preparing fatty acids from alkyl, preferably methyl esters comprising mixing the fatty acid ester with water, acid catalyst, and DMSO in order to form a single phase reaction mixture. The single phase reaction mixture is then heated to a temperature of from about 70.degree. C. to about 130.degree. C. to hydrolyze the fatty acid ester into the corresponding acid and volatile alcohol and removing the volatile alcohol. The acid catalyst is heat and water stable and the reaction mixture is essentially free of C.sub.2 -C.sub.5 carboxylic acids. The initial stoichiometric ratio of the water to the ester is at least about 1:1.
    Type: Grant
    Filed: March 29, 1994
    Date of Patent: August 8, 1995
    Assignee: The Procter & Gamble Company
    Inventor: Michael S. Gibson
  • Patent number: 5159092
    Abstract: An alkylene oxide is reacted in a loop reactor with an organic compound having a reactive hydrogen atom, a gas circulation and a liquid circulation around the reactor being provided and being coupled with one another via an ejector mixing nozzle. To ensure completeness of the reaction and suppression of the formation of by-products such as dioxane, it is essential to reduce the temperature of the entire alkylene oxide gas phase to a temperature below that of the liquid phase, and this is effected by feeding and evaporating liquid alkylene oxide and by cooling of the gas phase on the unit walls.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: October 27, 1992
    Assignee: Buss AG
    Inventor: Gunter M. Leuteritz
  • Patent number: 5128070
    Abstract: Process for the acid-catalyzed hydrolysis of fatty acid glycerides, wherein the process is carried out continuously with the glyceride and the water being moved countercurrent to each other, and apparatus therefor.
    Type: Grant
    Filed: August 1, 1989
    Date of Patent: July 7, 1992
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Reinhold Sedelies, Wilhelm Johannisbauer, Guenter Wozny, Lutz Jeromin, Gerhard Dieckelm, Manfred Lindemann, Gerd Matrong