WO2017137908A1 - Distillation de composés neutres à partir de savon à l'huile de pin - Google Patents

Distillation de composés neutres à partir de savon à l'huile de pin Download PDF

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Publication number
WO2017137908A1
WO2017137908A1 PCT/IB2017/050694 IB2017050694W WO2017137908A1 WO 2017137908 A1 WO2017137908 A1 WO 2017137908A1 IB 2017050694 W IB2017050694 W IB 2017050694W WO 2017137908 A1 WO2017137908 A1 WO 2017137908A1
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WO
WIPO (PCT)
Prior art keywords
tall oil
oil
process according
diluent
soap
Prior art date
Application number
PCT/IB2017/050694
Other languages
English (en)
Inventor
Jari KAVAKKA
Heikki LOTTI
Original Assignee
Stora Enso Oyj
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Stora Enso Oyj filed Critical Stora Enso Oyj
Publication of WO2017137908A1 publication Critical patent/WO2017137908A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/06—Evaporators with vertical tubes
    • B01D1/065—Evaporators with vertical tubes by film evaporating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/22—Evaporating by bringing a thin layer of the liquid into contact with a heated surface
    • B01D1/24—Evaporating by bringing a thin layer of the liquid into contact with a heated surface to obtain dry solids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D5/00—Condensation of vapours; Recovering volatile solvents by condensation
    • B01D5/0027—Condensation of vapours; Recovering volatile solvents by condensation by direct contact between vapours or gases and the cooling medium
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
    • C11B13/005—Recovery of fats, fatty oils or fatty acids from waste materials of residues of the fabrication of wood-cellulose (in particular tall-oil)
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

Definitions

  • the present invention relates to isolation of phytosterols and other neutral compounds from alkaline tall oil soap (TOS) which is obtained from the Kraft process black liquor by skimming.
  • TOS alkaline tall oil soap
  • the invention also enables the production of tall oil with high acid number.
  • Tall oil soap is a by-product of the Kraft process.
  • the soap consists mainly of sodium salts of fatty acids, sodium salts of diterpenic (rosin) acids, free fatty acids, free rosin acids and unsaponifiable neutral compounds such as fatty alcohols, sterols, steryl esters and waxes.
  • the water content of neat soap is typically 25 to 45%, such as 30 to 35%.
  • the pH of the soap is typically in the range of 1 1 to 13, arising from the presence of entrained black liquor.
  • soap is routinely acidulated with sulphuric acid to produce crude tall oil (CTO), an article of commerce. Crude tall oil can be refined by distillation into heads, tall oil fatty acids
  • TOFA tall oil rosin acids
  • TOP tall oil pitch
  • Sterols in particular phytosterols, have several uses, including the use as food additives and as precursors for steroids.
  • Several methods have been reported for the isolation of sterols from tall oil soap. The general method involves the extraction of neat soap with a variety of organic solvents. The presence of entrained black liquor promotes and stabilizes the unwanted water-oil emulsion, which is known to be extremely difficult to break.
  • the present invention is directed to a two stage treatment of tall oil soap in order to separate unsaponifiables and finally produce tall oil with high acid number.
  • the tall oil soap is dried.
  • the drying can be performed using a wiped film evaporator or other suitable technique.
  • a diluent is added in order to prevent the solidification of the distillation residue or the intended distillate.
  • the diluent concentration is chosen between 1 to 100 weight% (based on the wet soap).
  • a suitable diluent can be any chemically inert high boiling oil or solvent e.g silicon oil, mineral oil, paraffin oil etc, or mixture thereof which preferably does not dissolve the residue compounds at lower than working distillation temperature.
  • the dried tall oil soap is subjected to a short path distillation procedure. Since the distillate consists of high melting compounds like phytosterols, the distillate may solidify to the condensing part of the
  • a washing condenser system is used to avoid solidification of the distillate.
  • the washing solvent chosen must have a high boiling point but must be liquid in the condenser
  • washing solvents are chemically inert high boiling oil or solvent e.g silicon oil, mineral oil, paraffin oil etc, or mixtures thereof.
  • the washing solvent is either used directly as crystallization solvent for the purification of the phytosterols or separated prior to crystallization process.
  • the diluent is separated from the residue by filtration, washing, centrifugation, extraction or any combination thereof.
  • the neutral compound depleted tall oil soap can be acidified to produce tall oil with high acid number.
  • the present invention is directed to a process for isolation of
  • phytosterols and/or other neutral compounds from alkaline tall oil soap comprising the steps of a) drying the tall oil soap;
  • step b) adding a diluent to prevent solidification of the distillation residue or the distillate before, during or directly after step a); c) subjecting the dried tall oil soap to a short path distillation using a washing condenser system wherein the washing solvent has a boiling point such that it is liquid in the condenser temperature and able to dissolve the distillate at the condenser temperature; and
  • the drying in step a) is carried out in a wiped film evaporator.
  • the diluent is a chemically inert high boiling oil or solvent such as a silicon oil, mineral oil, paraffin oil or mixtures thereof.
  • the diluent is a mineral oil. In one embodiment of the present invention, the diluent is a silicon oil. In one embodiment of the present invention, the diluent is a paraffin oil.
  • the process also comprises the steps of e) removing the diluent from the distillation residue by washing using an organic solvent;
  • One embodiment of the present invention is a distillation residue obtainable by the process according to the present invention.
  • One embodiment of the present invention is tall oil having an acid number of at least 170, such as at least 175 or at least 180.
  • the tall oil is obtainable by the process according to the present invention.
  • phytosterol is intended to mean a sterol derived from plants and encompasses all plant sterols and the saturated forms of phytosterols thereof (i.e., phytostanols). Plant sterols fall into one of three categories: 4- desmethylsterols (lacking methyl groups); 4-monomethylsterols (one methyl group); and 4,4-dimethylsterols (two methyl groups) and include, but are not limited to, sitosterol (e.g., [alpha] and [beta] sitosterol), campesterol, stigmasterol, taraxasterol, and brassicasterol.
  • sitosterol e.g., [alpha] and [beta] sitosterol
  • phytostanol is intended to mean a saturated phytosterol and encompasses, but is not limited to, sitostanol (e.g., [alpha] and [beta] sitostanol), campestanol, stigmastanol, clionastanol, and brassicastanol.
  • sitostanol e.g., [alpha] and [beta] sitostanol
  • campestanol e.g., [alpha] and [beta] sitostanol
  • campestanol stigmastanol
  • clionastanol clionastanol
  • brassicastanol e.g., brassicastanol.
  • Phytosterols isolated by the methods of the invention may be quantified by any means known in the art. Suitable diluents include heavy mineral oils, silicon oil, polyethyleneoxides and paraffin oil.
  • a washing condenser is defined herein as an internal condenser used in
  • the phytosterol crystallization can be performed using methods known in the art, including cooling, concentration by removing some of the solvent by distillation, evaporation to dryness followed by introduction of a solvent or solvent mixture in which the phytosterols only dissolve at elevated
  • the process according to the present invention may be carried out as a batch process or as a continuous process.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Steroid Compounds (AREA)

Abstract

La présente invention concerne l'isolation de phytostérols et d'autres composés neutres d'un savon à l'huile de pin (TOS) alcalin qui est obtenu à partir de la liqueur noire du procédé kraft par écumage. La présente invention permet également la production d'huile de pin présentant un indice d'acide élevé.
PCT/IB2017/050694 2016-02-12 2017-02-09 Distillation de composés neutres à partir de savon à l'huile de pin WO2017137908A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE1650187-6 2016-02-12
SE1650187 2016-02-12

Publications (1)

Publication Number Publication Date
WO2017137908A1 true WO2017137908A1 (fr) 2017-08-17

Family

ID=58054384

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2017/050694 WO2017137908A1 (fr) 2016-02-12 2017-02-09 Distillation de composés neutres à partir de savon à l'huile de pin

Country Status (1)

Country Link
WO (1) WO2017137908A1 (fr)

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3965085A (en) 1973-06-29 1976-06-22 Bjarne Holmbom Method for refining of soaps using solvent extraction
US4044031A (en) 1976-07-02 1977-08-23 Ake Allan Johansson Process for the separation of sterols
US5770749A (en) 1994-09-29 1998-06-23 The University Of British Columbia - University Maison Office (Industrial) Process of isolating a phytosterol composition from pulping soap
EP0952208A2 (fr) * 1998-04-22 1999-10-27 Härting S.A. Procédé particulièrement efficace d'obtention d'une fraction insaponifiable à partir de liqueur noire ou d'huile de tall brute
CA2319230A1 (fr) 2000-09-13 2002-03-13 Alfred Wong Methode amelioree d'extraction de savon a l'huile de pin
US20020107168A1 (en) 2001-02-02 2002-08-08 Antti Hamunen Process for separating unsaponifiable valuable substances from sulphate soap based materials
US6462210B1 (en) 1999-04-16 2002-10-08 Harting, S.A. Fractionation process for the unsaponifiable material derived from black-liquor soaps
US6465665B1 (en) 1999-09-03 2002-10-15 Thomas Francis Harting Glade High efficiency process for the recovery of the high pure sterols
US20050107582A1 (en) 2003-07-30 2005-05-19 Alfred Wong Method for the preparation of phytosterols from tall oil pitch
US7078544B2 (en) 2001-08-22 2006-07-18 Harting, S.A. Process for producing sterol or stanol esters by enzymatic transesterification in solvent and water free media
US7087402B2 (en) 2001-08-22 2006-08-08 Harting, S.A. Selective transesterification of stanols in mixtures comprising sterols and stanols
US20090118524A1 (en) * 2006-03-19 2009-05-07 Uic Gmbh Process for Removing Volatile Components from a Substance Mixture & Apparatus for Performing this Process
WO2009106696A1 (fr) 2008-02-29 2009-09-03 Raisio Nutrition Ltd Procédé de séparation de stérols et d'acides à partir du brai de tallöl

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3965085A (en) 1973-06-29 1976-06-22 Bjarne Holmbom Method for refining of soaps using solvent extraction
US4044031A (en) 1976-07-02 1977-08-23 Ake Allan Johansson Process for the separation of sterols
US5770749A (en) 1994-09-29 1998-06-23 The University Of British Columbia - University Maison Office (Industrial) Process of isolating a phytosterol composition from pulping soap
EP0952208A2 (fr) * 1998-04-22 1999-10-27 Härting S.A. Procédé particulièrement efficace d'obtention d'une fraction insaponifiable à partir de liqueur noire ou d'huile de tall brute
US6297353B1 (en) 1998-04-22 2001-10-02 Harting, S.A. Process for obtaining unsaponifiable compounds from black-liquor soaps, tall oil and their by-products
US6462210B1 (en) 1999-04-16 2002-10-08 Harting, S.A. Fractionation process for the unsaponifiable material derived from black-liquor soaps
US6465665B1 (en) 1999-09-03 2002-10-15 Thomas Francis Harting Glade High efficiency process for the recovery of the high pure sterols
CA2319230A1 (fr) 2000-09-13 2002-03-13 Alfred Wong Methode amelioree d'extraction de savon a l'huile de pin
US20020107168A1 (en) 2001-02-02 2002-08-08 Antti Hamunen Process for separating unsaponifiable valuable substances from sulphate soap based materials
US7078544B2 (en) 2001-08-22 2006-07-18 Harting, S.A. Process for producing sterol or stanol esters by enzymatic transesterification in solvent and water free media
US7087402B2 (en) 2001-08-22 2006-08-08 Harting, S.A. Selective transesterification of stanols in mixtures comprising sterols and stanols
US20050107582A1 (en) 2003-07-30 2005-05-19 Alfred Wong Method for the preparation of phytosterols from tall oil pitch
US20090118524A1 (en) * 2006-03-19 2009-05-07 Uic Gmbh Process for Removing Volatile Components from a Substance Mixture & Apparatus for Performing this Process
WO2009106696A1 (fr) 2008-02-29 2009-09-03 Raisio Nutrition Ltd Procédé de séparation de stérols et d'acides à partir du brai de tallöl

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MILENA ROUSKOVÁ ET AL: "Extraction of phytosterols from tall oil soap using selected organic solvents", CHEMICAL PAPERS, SP VERSITA, HEIDELBERG, vol. 65, no. 6, 26 August 2011 (2011-08-26), pages 805 - 812, XP019957867, ISSN: 1336-9075, DOI: 10.2478/S11696-011-0077-3 *

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