Recovery Of Tall Oil Or Derivatives From Papermaking Waste, Purification Of Tall Oil, Or Separation Of Components Of Tall Oil; Or Product Thereof (e.g., Separation Of Rosin, Fatty Acids, Sterols, Etc.; Decolorizing, Etc.) Patents (Class 530/205)
  • Patent number: 10041020
    Abstract: A process and apparatus for recovering crude tall oil are disclosed. Acidulation of a crude tall oil soap stream generates a spent acid stream that comprises lignin and entrained crude tall oil. By subjecting the spent acid stream to dissolved gas flotation, a lignin phase comprising entrained crude tall oil can be recovered and causticized, resulting in recovery of most of the crude tall oil that was present in the spent acid stream. A clarified spent acid stream is also generated, which can be treated with caustic and utilized for a soap washing process that integrates easily into the overall CTO recovery process. The apparatus comprises a crude tall oil acidulation unit, a dissolved gas flotation unit, a causticizing unit, and a soap separation unit. The inventive process marries dissolved gas flotation, a well-known water treatment process, with causticization of a recovered lignin phase, a step known from batch acidulation, to improve overall tall oil recovery from a continuous process.
    Type: Grant
    Filed: September 12, 2015
    Date of Patent: August 7, 2018
    Assignee: Kraton Chemical, LLC
    Inventors: Charles Douglas Foran, Francis Edwin Swann, Robert Earl Bowles
  • Patent number: 9926503
    Abstract: The present invention relates to a process and system for producing fuel components, and more particularly to a process and system for producing fuel components from a material of biological origin. The process is a two-step or a three-step process comprising purifying of the feed material by evaporating and refining the purified feed material in the presence of at least one catalyst to form a mixture of hydrocarbon compounds from which mixture liquid hydrocarbon compounds are separated and further fractionated into fuel components. The present invention relates further to fuel components obtained by the process of the present invention as well as to the use of the fuel components and a mixture comprising the fuel components.
    Type: Grant
    Filed: November 25, 2011
    Date of Patent: March 27, 2018
    Assignee: UPM-KYMMENE CORPORATION
    Inventors: Heli Laumola, Jari Kotoneva, Arto Rissanen, Jaakko Nousiainen
  • Patent number: 9624442
    Abstract: A method of treating tall oil pitch. In the present method, part of the fatty acids and the resin acids are released from their sterol esters and wood alcohol esters and converted into methanol esters or ethanol esters. The transesterified products are removed from the pitch by evaporation and then condensed, and by hydrogenating the generated condensate the acids are decarboxylated and the double bonds are satisfied. It is possible to use the present method to produce automotive fuel from tall oil pitch.
    Type: Grant
    Filed: March 28, 2011
    Date of Patent: April 18, 2017
    Assignee: FORCHEM OYJ
    Inventors: Juhani Saviainen, Mikko Rintola, Timo Saarenko
  • Patent number: 9487717
    Abstract: Disclosed is an enrichment method for obtaining components for the production of a diesel like fuel additive or a diesel like fuel from crude tall oil. In the method, lipophilic components, being present in said crude tall oil, are extracted with an organic solvent and the resulting extract is washed with sulfuric acid and water.
    Type: Grant
    Filed: December 7, 2012
    Date of Patent: November 8, 2016
    Assignee: Invico Tech AB
    Inventor: Jan Warnqvist
  • Patent number: 9186596
    Abstract: Odorant from a process stream is removed by passing the stream (18) to a counter-current contacting device (12) for stripping odorants. The odorants passes from the contacting device (12) as contaminated steam (26) while the remaining process stream passes directly to a “tube side” of a falling film evaporator (14) and is heated producing steam that passes into the counter-current contacting device (12) to strip that process stream and produce the contaminated steam (26). This contaminated steam from the contacting device (12) passes through a vapor compression step (16) from which it is introduced into a “shell side” of the falling film evaporator (14) and in which it heats the process stream passing from the contacting device (12) into the evaporator (14). The contaminated steam that is not condensed in the falling film evaporator passes as a low flow vent gas (50) in which the odorants have been concentrated.
    Type: Grant
    Filed: August 10, 2010
    Date of Patent: November 17, 2015
    Assignee: Alcoa of Australia Limited
    Inventor: Peter Stewart Hay
  • Patent number: 8916031
    Abstract: Described is a process to obtain tetracosanol from a complex mixture derived from tall oil pitch that comprises terpenoids, rosin alcohols, rosin aldehydes, aliphatic alcohols, hydrocarbons and stilbene derivatives. The process comprises a mixture crystallization step from hexane and a fractional distillation of the crystallized solids, which yields tetracosanol with more than 90% purity.
    Type: Grant
    Filed: May 10, 2010
    Date of Patent: December 23, 2014
    Assignees: Pontificia Universidad Catolica de Valparaiso, Harting S.A.
    Inventors: Miguel Angel Fuenzalida Diaz, Alejandro Markovits Rojas, Miriam Berrios Cornejo, Mabel Keller Mena, Jose Rodrigo Vergara Salinas, Glenda Cea Barcia, Andres Illanes Frontaura, Rolando Arturo Chamy Maggi, Andres Markovits Schersl, Araceli Olivares Miralles
  • Patent number: 8865922
    Abstract: A method of treating tall oil pitch, which comprises sterol esters of fatty acids. According to the present invention, the esters of sterols and fatty acids are broken down, in which case especially formic acid esters or acetic acid esters of sterols are formed instead. The free fatty acids and sterol esters generated are distilled or separated in another way. Use of the present invention increases the yield of fatty acids and also facilitates the separation of sterols from tall oil pitch.
    Type: Grant
    Filed: March 28, 2011
    Date of Patent: October 21, 2014
    Assignee: Forchem Oy
    Inventors: Esko Kiviranta, Juhani Saviainen, Mikko Rintola
  • Publication number: 20130261284
    Abstract: A process for recovering fatty acids, resin acids and sterols from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase, c) separating the aqueous phase from the organic phase, d) evaporation fractionating the organic phase to obtain a distillate rich in sterols, fatty acids and resin acids, d) evaporation fractionating the organic phase to obtain a distillate rich in sterols, fatty acids and resin acids, e) evaporation fractionating the distillate to obtain a bottom fraction rich in sterols, and a distillate rich in fatty acids and resin acids, and f) subjecting the sterols in the sterol-rich bottom fraction to crystallisation purification.
    Type: Application
    Filed: May 1, 2013
    Publication date: October 3, 2013
    Applicant: RAVINTORAISIO OY
    Inventor: Antti HAMUNEN
  • Patent number: 8450453
    Abstract: The invention relates to a process for recovering fatty acids, resin acids and sterols from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase, c) separating the aqueous phase from the organic phase, d) evaporation fractionating the organic phase to obtain a distillate rich in sterols, fatty acids and resin acids, e) evaporation fractionating the distillate to obtain a bottom fraction rich in sterols, and a distillate rich in fatty acids and resin acids, and f) subjecting the sterols in the sterol-rich bottom fraction to crystallization purification.
    Type: Grant
    Filed: February 15, 2008
    Date of Patent: May 28, 2013
    Assignee: Ravintoraisio OY
    Inventor: Antti Hamunen
  • Patent number: 8419897
    Abstract: A method for producing crude tall oil from black liquor soap while removing calcium carbonate and lignates is disclosed. Black liquor soap is first combined with an alkaline ash medium having a lower concentration of lignates and inorganic solids than the black liquor soap, to form washed tall oil soap, fortified brine, lignates, and calcium carbonate. The washed tall oil soap is then separated from the fortified brine, lignates, and calcium carbonate, by centrifugation, decantation, filtration, settling, or a combination of these techniques. Acidification of the washed tall oil soap gives crude tall oil and a spent acid mixture. The crude tall oil is separated from the spent acid. The spent acid is made alkaline, and at least a portion of it is returned for use as alkaline wash medium. The method avoids accumulation of calcium sulfate in acidulation units.
    Type: Grant
    Filed: November 22, 2011
    Date of Patent: April 16, 2013
    Assignee: Arizona Chemical Company, LLC
    Inventors: Robert E. Bowles, C. Douglas Foran, Joseph H. Griffin, F. Edwin Swann
  • Patent number: 8338564
    Abstract: A method of preparing phytosterols from tall oil pitch containing steryl esters comprises the steps of converting the steryl esters to free phytosterols while in the pitch to produce a modified pitch containing the free phytosterols; removing light ends from the modified pitch by evaporation to produce a bottom fraction containing the free phytosterols; evaporating the bottom fraction to produce a light phase distillate containing the free phytosterols; dissolving the light phase distillate in a solvent comprising an alcohol to produce a solution containing the free phytosterols; cooling the solution to produce a slurry with the free phytosterols crystallized in the slurry; and, washing and filtering the slurry to isolate the crystallized phytosterols.
    Type: Grant
    Filed: August 4, 2010
    Date of Patent: December 25, 2012
    Assignee: Pharmachem Laboratories, Inc.
    Inventors: Alfred Wong, Hugh Sven Oscar Norman, Angus Kirke MacMillan
  • Publication number: 20120296066
    Abstract: A continuous method and an arrangement for separation of crude tall oil (CTO) from black liquor. The method involves an initial separation within a tank and/or within a centrifugal separator, and processing of the thus separated tall oil soap product by acidulation and/or splitting, followed by further separation, e.g. by centrifugation. The black liquor fraction may be processed for further CTO retrieval, before evaporation and feeding to a recovery boiler.
    Type: Application
    Filed: December 28, 2010
    Publication date: November 22, 2012
    Inventor: Anders Goran Hofstedt
  • Patent number: 7763717
    Abstract: A process and system for recovering protein and lipid from food animal byproducts, and the products thereof, involves homogenizing animal byproducts with water to form a homogenate, solubilizing the homogenate by adjusting the pH of the homogenate to form a first pH adjusted composition, separating the first pH adjusted composition forming a light fraction containing lipids (oil), a medium fraction containing protein in solution, and a heavy fraction containing fat-free impurities, separation by first centrifugation, adjusting the pH of the medium fraction to about the isoelectric point of the proteins thereby precipitating the medium fraction forming a second pH adjusted composition, and separating the second pH adjusted composition forming a light fraction containing water and a heavy fraction containing precipitated proteins. The water may then be recycled and used in the homogenization of further byproducts.
    Type: Grant
    Filed: March 7, 2006
    Date of Patent: July 27, 2010
    Assignee: West Virginia University Research Corp. of West Virginia University
    Inventor: Jacek Jaczynski
  • Publication number: 20100137556
    Abstract: The invention relates to a process for recovering fatty acids, resin acids and sterols from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase, c) separating the aqueous phase from the organic phase, d) evaporation fractionating the organic phase to obtain a distillate rich in sterols, fatty acids and resin acids, e) evaporation fractionating the distillate to obtain a bottom fraction rich in sterols, and a distillate rich in fatty acids and resin acids, and f) subjecting the sterols in the sterol-rich bottom fraction to crystallisation purification.
    Type: Application
    Filed: February 15, 2008
    Publication date: June 3, 2010
    Applicant: Ravintoraiso OY
    Inventor: Antii Hamunen
  • Publication number: 20090227767
    Abstract: The invention relates to a process for the production of tall oil from soap oil and to the use of heating in order to improve the production of tall oil. Soap oil, which has been produced by neutralization of tall oil soap, is acidulated by reacting the soap oil with an acid and freed tall oil is recovered. In the acidulation step, the temperature is raised above 100° C., preferably over 105° C., for improving the acidulation of soap oil. The acid is preferably concentrated sulfuric acid.
    Type: Application
    Filed: June 20, 2007
    Publication date: September 10, 2009
    Applicant: LINDE AKTIENGESELLSCHAFT
    Inventors: Per Sellerholm, Nils Kjellberg, Jonas Jonsson, Valeri Naydenov, Curt Lindstrom
  • Patent number: 7504478
    Abstract: Methods of increasing the yield of tall oil soap from a black liquor are provided. In an embodiment, the method comprises adding a separation aid to the black liquor. The separation aid comprises alkyl alcohol alkoxylates of formula RO[(CH2CHCH3O)x(CH2CH2O)y]M and combinations thereof, wherein R is straight or branched alkyl of about 8 to about 22 carbon atoms; x is 1 to about 20; y is about 20 to about 80 and M is H or an alkali metal.
    Type: Grant
    Filed: January 26, 2007
    Date of Patent: March 17, 2009
    Assignee: Nalco Company
    Inventors: James J. Svarz, Prasad Y. Duggirala, Grady E. Worley
  • Publication number: 20080182967
    Abstract: Methods of increasing the yield of tall oil soap from a black liquor are provided. In an embodiment, the method comprises adding a separation aid to the black liquor. The separation aid comprises alkyl alcohol alkoxylates of formula RO[(CH2CHCH3O)x(CH2CH2O)y]M and combinations thereof, wherein R is straight or branched alkyl of about 8 to about 22 carbon atoms; x is 1 to about 20; y is about 20 to about 80 and M is H or an alkali metal.
    Type: Application
    Filed: January 26, 2007
    Publication date: July 31, 2008
    Inventors: James J. Svarz, Prasad Y. Duggirala, Grady E. Worley
  • Patent number: 7208570
    Abstract: The present invention relates to a method of refining crude tall oil. According to the method, the crude tall oil is fed into a column distiller, where it is separated into desired fractions. The conditions of the column distiller are adjusted on the basis of the composition of the feed and the product flow. According to the present invention, the densities of the crude tall oil fed into the column distiller and of at least one product flow are measured accurately as a function of the temperature. The density values are compared with correlation coefficients derived from the chemical compositions of the flows, coefficients which are obtained on the basis of laboratory analyses made earlier from corresponding flows, by using temperature compensation to specify the correlations, and by taking account of the regular variation in the wood composition of fresh wood according to the annual cycle and, as a result, the compositions of the flows are achieved.
    Type: Grant
    Filed: February 18, 2005
    Date of Patent: April 24, 2007
    Assignee: Forchem Oy
    Inventor: Juhani Saviainen
  • Patent number: 7084238
    Abstract: A process for separating sodium bicarbonate brine from crude tall oil or for separating sulfate brine from soap oil, such as in a recovery process in a pulp mill. A water solution having an increased density is added during the neutralization of crude tall oil soap with carbon dioxide or acidulation of soap oil with sulfuric acid.
    Type: Grant
    Filed: April 8, 2004
    Date of Patent: August 1, 2006
    Assignee: Linde Aktiengesellschaft
    Inventor: Nils Kjellberg
  • Patent number: 6844420
    Abstract: This invention is directed to a method of preparing a natural resin by liquefying wood, bark, forest residues, wood industry residues, or other biomass using rapid destructive distillation (fast pyrolysis). Fast pyrolysis produces both vapors and char from biomass, and following removal of the char from the product vapors, a liquid pitch product is recovered and processed by distillation, evaporation, or a combination thereof, in order to obtain a natural resin which may be in either liquid or solid form. The natural resin comprises a total phenolic content from about 30% to about 80% (w/w), and is a highly-reactive ligninic compound that has been found to be suitable for use within resin formulations without requiring any further extraction or fractionation procedures. Resins comprising up to 60% natural resin have been prepared and tested in board production and found to exhibit similar properties associated with commercially available resins.
    Type: Grant
    Filed: July 28, 2000
    Date of Patent: January 18, 2005
    Assignee: Ensyn Renewables, Inc.
    Inventors: Barry Freel, Robert G. Graham, Régi Giroux
  • Patent number: 6555649
    Abstract: This invention is directed to a method of preparing a natural resin by liquefying wood, bark, forest residues, wood industry residues, or other biomass using rapid destructive distillation (fast pyrolysis). Fast pyrolysis produces both vapours and char from biomass, and following removal of the char from the product vapours, a liquid pitch product is recovered and processed by distillation, evaporation, or a combination thereof, in order to obtain a natural resin which may be in either liquid or solid form. The natural resin comprises a total phenolic content from about 30% to about 80% (w/w), and is a highly-reactive ligninic compound that has been found to be suitable for use within resin formulations without requiring any further extraction or fractionation procedures. Resins comprising up to 60% natural resin have been prepared and tested in board production and found to exhibit similar properties associated with commercially available resins.
    Type: Grant
    Filed: November 16, 2001
    Date of Patent: April 29, 2003
    Assignee: Ensyn Group, Inc.
    Inventors: Regi Giroux, Barry Freel, Robert Graham
  • Patent number: 6433121
    Abstract: A method for making natural oil-based polyols directly from vegetable or animal oil using a consecutive two-step process involving epoxidation and hydroxylation is provided. Specifically, this process comprises adding a peroxyacid to a natural oil wherein said natural oil and said peroxyacid react to form an epoxidized natural oil and adding said epoxidized natural oil to a mixture of an alcohol, water, and a fluoboric acid catalyst. The catalytic amount of fluoboric acid is less than about 0.5% by weight of the entire reaction mixture, and the amount of water is about 10 to 30% by weight of the entire mixture. The epoxidized natural oil undergoes hydroxylation and forms a natural oil-based polyol. The present invention further includes a method for making natural oil-based polyols from epoxidized oil by hydroylating the epoxidized oil in the presence of fluoboric acid, alcohol and water in the amounts discussed above.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: August 13, 2002
    Assignee: Pittsburg State University
    Inventors: Zoran Petrovic, Ivan Javni, Andrew Guo, Wei Zhang
  • Patent number: 6420533
    Abstract: This method will produce depolymerized lignins substantially free from sodium compounds. Black liquor supplied from a pulping process is utilized for providing a mixture of depolymerized lignins dispersed and dissolved in absolution containing sodium hydroxide. The mixture is then separated to form depolymerized lignins and a solution containing sodium hydroxide. Following separation, the depolymerized lignins are then extracted with water to produce an extractate containing water soluble sodium compounds. The extracted depolymerized lignins, containing sodium compounds, are then reacted with an acid to form sodium salts. The solution containing sodium salts is then separated from the extracted depolymerized lignins to produce substantially sodium free depolymerized lignins. The separated solution containing sodium hydroxide is combined with the extractate and the combination, subsequent to removal of water, is made available to reuse for recycle to depolymerize, disperse and dissolve additional lignins.
    Type: Grant
    Filed: August 4, 2000
    Date of Patent: July 16, 2002
    Inventor: Gene E. Lightner
  • Patent number: 6414111
    Abstract: A method is set forth for separating a sterol or sterol ester from crude tall oil comprising fractionating the crude tall oil into a residue fraction and a volatile fraction, wherein the temperature of the residue fraction does not exceed about 290° C., and wherein the residue fraction includes the sterol or sterol ester. By application of this method, which can be implemented in existing fractionating equipment or in specially designed pitch collecting apparatuses disclosed herein, the yield of sterols can exceed 50% with respect to the sterols present in crude tall oil. A method is also provided for separating unsaponifiable material from a tall oil stream comprising saponifying the stream with a mixture of sodium hydroxide and potassium hydroxide to form sodium and potassium salts of fatty acids, rosin acids, or both; evaporating the unsaponifiable material; and acidulating the unevaporated sodium and potassium salts.
    Type: Grant
    Filed: February 14, 2001
    Date of Patent: July 2, 2002
    Assignee: Arizona Chemical Company
    Inventors: Derk T. A. Huibers, Andrew M. Robbins, David H. Sullivan
  • Patent number: 6348566
    Abstract: The invention relates to a method for enhancing the cooking step in a tall oil preparation process comprising: a neutralization step in which soap is neutralied to form soap oil, and a cooking step in which soap oil is cooked with sulphuric acid to form tall oil, the soap oil obtained in the neutralization step being subjected to an intermediate treatment before the cooking step, the intermediate treatment comprising heating of the soap oil to release gases dissolved in and bound to the soap oil. The invention also relates to a method for preparing tall oil comprising the steps mentioned above.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: February 19, 2002
    Assignee: L'Air Liquide Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges Claude
    Inventor: Seppo Sarasto
  • Patent number: 6326461
    Abstract: This invention is directed to a method of preparing a natural resin by liquefying wood, bark, forest residues, wood industry residues, or other biomass using rapid destructive distillation (fast pyrolysis). Fast pyrolysis produces both vapors and char from biomass, and following removal of the char from the product vapors, a liquid pitch product is recovered and processed by distillation, evaporation, or a combination thereof, in order to obtain a natural resin which may be in either liquid or solid form. The natural resin comprises a total phenolic content from about 30% to about 80% (w/w), and is a highly-reactive ligninic compound that has been found to be suitable for use within resin formulations without requiring any further extraction or fractionation procedures. Resins comprising up to 60% natural resin have been prepared and tested in board production and found to exhibit similar properties associated with commercially available resins.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: December 4, 2001
    Assignee: Ensyn Group, Inc.
    Inventors: Regi Giroux, Barry Freel, Robert Graham
  • Patent number: 6297353
    Abstract: A method for obtaining neutral compounds from black-liquor soaps, tall oil and tall oil by-products is disclosed. The method includes the steps of: (1) dehydrating black liquor soaps, neutralized tall oil, or neutralized tall oil by-products to form a dehydrated current; (2) distilling the dehydrated current in a distillation column; (3) collecting an essentially soap free distillate; and (4) collecting an essentially neutral compound free residue. Also disclosed is a method for obtaining a sterol concentrate from black-liquor soap solutions, neutralized tall oil, or neutralized tall oil by-products. In this method, a distillation operation is repeated until a current of sterols with the desired purity is obtained. The method yields a sterol concentrate with a level of purity over 96%.
    Type: Grant
    Filed: April 19, 1999
    Date of Patent: October 2, 2001
    Assignee: Harting, S.A.
    Inventors: Miguel Angel Fuenzalida Diaz, Alejandro Markovits Rojas, Roberto Benito Leiva Hinojosa, Endre Markovits Schersl
  • Patent number: 6172183
    Abstract: The present invention relates to a process and apparatus for the cleaning of crude tall oil soap. Crude soap floating on top of a layer of black liquor is cleaned with carbon dioxide, in a tall oil recovery system containing a cleaning vessel (T) for crude tall oil soap and black liquor. Said vessel has a carbon dioxide inlet (6) for introducing cleaning carbon dioxide into the soap. The cleaning vessel (T) is also provided with a black liquor separately from the cleaned soap. The cleaned soap may be acidified so as to provide tall oil.
    Type: Grant
    Filed: October 21, 1999
    Date of Patent: January 9, 2001
    Assignee: AGA Aktiebolag
    Inventor: Hannu Juhani Leino
  • Patent number: 6107456
    Abstract: A method is set forth for separating a sterol or sterol ester from crude tall oil comprising fractionating the crude tall oil into a residue fraction and a volatile fraction, wherein the temperature of the residue fraction does not exceed about 290.degree. C., and wherein the residue fraction includes the sterol or sterol ester. By application of this method, which can be implemented in existing fractionating equipment or in specially designed pitch collecting apparatuses disclosed herein, the yield of sterols can exceed 50% with respect to the sterols present in crude tall oil. A method is also provided for separating unsaponifiable material from a tall oil stream comprising saponifying the stream with a mixture of sodium hydroxide and potassium hydroxide to form sodium and potassium salts of fatty acid, rosin acids, or both; evaporating the unsaponifiable material; and acidulating the unevaporated sodium and potassium salts.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: August 22, 2000
    Assignee: Arizona Chemical Corporation
    Inventors: Derk T. A. Huibers, Andrew M. Robbins, David H. Sullivan
  • Patent number: 5898065
    Abstract: The invention relates to a method for improving the separation of water in a tall oil preparation process which comprises: a neutralization step, in which a mixture of tall oil soap and water is neutralized with carbon dioxide; a water separation step, in which the aqueous phase containing bicarbonate is separated from the tall oil soap; and a cooking step, in which the tall oil soap obtained from the previous step is cooked with sulfuric acid in order to form tall oil, the improvement comprising the fact that, after the neutralization with carbon dioxide but before the water separation step, the pH is adjusted with an acidically reacting substance, such as bisulfite. The invention also relates to a method for the preparation of tall oil, the method comprising the steps stated above.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: April 27, 1999
    Assignee: L'Air Liquide, Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges Claude
    Inventors: Eero Aitta, Elias Varila
  • Patent number: 5698668
    Abstract: Toluene-soluble modified natural-resin acid esters which can be prepared by reacting at least one compound from each of the component groups: A) natural resins or natural-resin acids; B) .alpha.,.beta.-ethylenically unsaturated carboxylic acids or their anhydrides; C) phenols which are polyfunctional with respect to oxo compounds; D) aldehydes or aldehyde acetals; E) alcohols having at least two hydroxyl groups; and, if desired, further compounds from the substance groups: F) fatty acids or fatty acid esters; G) ethylenically unsaturated monomers; H) ethylenically unsaturated hydrocarbon resins in the presence of: I) monovalent or divalent metal compounds or mixtures thereof at a temperature of from 100.degree. to 300 .degree. C., with elimination of water, to an acid number of less than 100 mg of KOH/g of resin, and then reacting the resulting products with: J) carboxylic acids which contain at least two carboxyl groups and are not .alpha.,.beta.
    Type: Grant
    Filed: June 3, 1996
    Date of Patent: December 16, 1997
    Assignee: Vianova Resins GmbH
    Inventor: Albert Bender
  • Patent number: 5691154
    Abstract: An improvement in enzyme linked immunoassays is disclosed wherein the enzyme is in the form of a water soluble polymer saccharide conjugate which is stable in hostile environments. The conjugate comprises the enzyme which is linked to the polymer at multiple points through saccharide linker groups.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: November 25, 1997
    Assignee: Cargill, Incorporated
    Inventors: Matthew R. Callstrom, Mark D. Bednarski, Patrick R. Gruber
  • Patent number: 5543110
    Abstract: A process for deodorizing tall oil rosin and tall oil fatty acids and their derivatives by treating same with an ammonium hydroxide solution under conditions of a steam sparge.
    Type: Grant
    Filed: January 26, 1995
    Date of Patent: August 6, 1996
    Assignee: Westvaco Corporation
    Inventors: Fredricke S. Starr, Joseph M. Wong, Norman L. Kennedy
  • Patent number: 5492821
    Abstract: This invention is directed to water soluble protein polymer conjugates which are stabile in hostile environments. The conjugate comprises a protein which is linked to an acrylic polymer at multiple points through saccharide linker groups.
    Type: Grant
    Filed: November 13, 1991
    Date of Patent: February 20, 1996
    Assignee: Cargill, Inc.
    Inventors: Matthew R. Callstrom, Mark D. Bednarski, Patrick R. Gruber
  • Patent number: 5455328
    Abstract: The invention relates to acidification of soap, wherein the acidification is performed with a sodium bisulphite solution produced by absorbing the SO.sub.2 entrained in the flue gases obtained from the combustion of odor gases derived from a chemical pulp mill into an alkaline sodium solution which is NaOH or oxidized white liquor, or with a sodium bisulphite solution which is NaHSO.sub.3 -containing mother liquid obtained from SO.sub.2 or NaHSO.sub.3 acidification of soap. The acidification can be conducted in one or more steps and by the cross-current and/or counter-current method by recycling the Na.sub.2 SO.sub.3 mother liquid obtained from the acidification.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: October 3, 1995
    Assignee: LT-Dynamics Oy
    Inventors: Olavi Vuorikari, Teemu Tanner, Jukka Koistinen, Kari Sarkkinen, Esko Mattelmaki
  • Patent number: 5283319
    Abstract: The present invention provides for the efficient recycling of carbon dioxide used in high pressure tall oil soap acidulation processes. The excess carbon dioxide used in the high pressure tall oil soap acidulation processes is recycled and contacted with an aqueous tall oil soap solution at a point before the high pressure contacting stage. Preferably, the recycled carbon dioxide is contacted in a first reactor, under pressure, to provide a preliminary tall oil mixture having an extent of acidification beyond the presence of a gel phase. Methods are provided for the monitoring of the acidulation reaction in the first reactor to maintain the extent of acidification beyond the gel phase region.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: February 1, 1994
    Assignee: Union Camp Corporation
    Inventors: Derk T. A. Huibers, Richard G. Grotyohann, Andrew M. Robbins
  • Patent number: 5132399
    Abstract: The color and color stability of tall oil fractions are improved and the odor and sulfur content are reduced by treating the heated black liquor soap skimmings prior to acidulation with 1.0 to 1.5 wt. % hydrogen peroxide for at least one minute.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: July 21, 1992
    Assignee: Hercules Incorporated
    Inventors: Charles M. MacDonald, Richard R. Suchanec
  • Patent number: 5082497
    Abstract: A gravure printing ink comprising, a vehicle having a binder dissolved in a hydrocarbon solvent and a pigment dispersed therein, wherein the binder is a modified rosin resinate prepared by reacting a rosin modified by reaction with a dienophile to form a rosin adduct, and reacting the rosin adduct with from about 0.1% to about 5.0% by weight of the resinate of a reactive compound of a metal belonging to Group I of the Periodic Table to form a resinate.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: January 21, 1992
    Assignee: Westvaco Corporation
    Inventor: Joseph W. LeVine
  • Patent number: 4977243
    Abstract: An adsorptive separation process for separating sterols from a feed mixture, especially one that is acid-free, containing sterols, e.g., tan oil, wool fat, etc., which process comprises contacting the feed mixture with an adsorbent comprising magnesium silicate (Florisil), selectively adsorbing substantially all of the sterols to be separated to the substantial exclusion of the other components and thereafter recovering high purity sterols. The adsorbed sterols are desorbed with methyl-t-butyl ether (MtBE), which is superior, as a desorbent, to previously used aromatic liquids, e.g., toluene and chlorobenzene. An especially suitable acid-free feed is produced from crude tall oil, without the need for pitching, by a liquid-liquid extraction with DMSO and hexane solvents added to the top and bottom of the extraction column, respectively, and feed introduced at an intermediate zone.
    Type: Grant
    Filed: December 28, 1988
    Date of Patent: December 11, 1990
    Assignee: UOP
    Inventors: Timothy J. Barder, W. Brian Bedwell, Steven P. Johnson
  • Patent number: 4879369
    Abstract: Lignin is removed from a crude tall oil in the production of tall oil fractions suitable for use as chemical ingredients and additives in other products by sparging the crude tall oil at a temperature of between about 350.degree. F. to 400.degree. F. with a carrier gas to depolymerize and remove from the tall oil lower molecular weight lignin materials.
    Type: Grant
    Filed: January 20, 1988
    Date of Patent: November 7, 1989
    Assignee: Westvaco Corporation
    Inventor: Carlton G. Force