WO2000059921A1 - Preparation de phytosterols satures - Google Patents

Preparation de phytosterols satures Download PDF

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Publication number
WO2000059921A1
WO2000059921A1 PCT/CA2000/000357 CA0000357W WO0059921A1 WO 2000059921 A1 WO2000059921 A1 WO 2000059921A1 CA 0000357 W CA0000357 W CA 0000357W WO 0059921 A1 WO0059921 A1 WO 0059921A1
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WO
WIPO (PCT)
Prior art keywords
phytosterols
mixture
raw material
hydrogenation
solvent
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/CA2000/000357
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English (en)
Inventor
Alfred Wong
Wilfred Nicholas Boguski
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bc Chemicals Ltd
Original Assignee
Bc Chemicals Ltd
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 Bc Chemicals Ltd filed Critical Bc Chemicals Ltd
Priority to AU36509/00A priority Critical patent/AU3650900A/en
Publication of WO2000059921A1 publication Critical patent/WO2000059921A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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 the preparation of saturated phytosterols and, more particularly, to a method of preparing an end product mixture of saturated phytosterols, at -least a substantial of the mixture consisting of saturated phytosterols, from a raw material mixture of phytosterols derived from tall oil, at least a substantial portion of the raw material mixture consisting of unsaturated phytosterols.
  • phytosterols One important source of phytosterols is tall oil, and there are known methods for isolating phytosterols and their saturated or hydrogenated (stanol) forms either from tall oil soap (sometimes referred to as soap skimmings) or from tall oil pitch.
  • ⁇ -sitosterol and campesterol When phytosterols are isolated from tall oil, a portion of the isolated mix (normally including ⁇ -sitosterol and campesterol) will typically include at least some hydrogenated forms of the sterols (viz. ⁇ -sitostanol and campestanol). However, given the higher efficacy of ⁇ -sitostanol compared to ⁇ -sitosterol, it is desirable that substanti.ally all ⁇ -sitosterols present in any such mix should be converted to ⁇ -sitostanols.
  • the conversion of a sterol to a stanol is, by definition, hydrogenation.
  • hydrogenation it is known to hydrogenate a phytosterol or a phytosterol mixture by mixing the phytosterol with a solvent in a reactor in the presence of an appropriate catalyst.
  • hydrogenation is mandated, relatively little attention has been paid to how hydrogenation may best be achieved, including which solvent may be best suited to the hydrogenation process.
  • the ability to do so can be impaired if the execution of the hydrogenation process introduces impurities or contaminants either as the result of phytosterol break down or otherwise. Impurities or contaminants that are carried with the saturated phytosterols may, at added cost, require removal. Likewise, to extend the lifetime of the hydrogenation solvent, any impurities or contaminants that are carried with the solvent may require removal before the solvent is recycled.
  • a further important factor that contributes to the overall cost of producing saturated phytosterols is the time that it takes to dry or sufficiently remove the presence of solvent from the end product.
  • saturated phytosterols are to be used in the preparation of food additives or dietary supplements, government regulations typically will permit the presence of only a very small amount of solvent residue (for example, 50 parts per million).
  • a primary object of the present invention is to provide a new and improved method for efficiently preparing a high purity end product mixture of saturated phytosterols from a raw mixture of phytosterols derived from tall oil - and one which converts a high percentage of unsaturated phytosterols present in the raw material mixture to corresponding saturated phytosterols.
  • a method for the preparation of an end product mixture of phytosterols, at least a substantial portion of the mixture consisting of saturated phytosterols, from a raw material mixture of phytosterols derived from tall oil, at least a substantial portion of the raw material mixture consisting of unsaturated phytosterols, such method comprising the steps of
  • the temperature is greater than 35 deg. C. (preferably about 40 deg. C. or higher) and the pressure is greater than standard pressure (preferably about 20 psi or higher).
  • Suitable catalysts include platinum dioxide and palladium. However, by reason of its lower cost, the latter is preferred.
  • the resulting end product mixture of saturated phytosterols may be used for various purposes including the manufacture of food additives or dietary supplements with a view to facilitating the reduction of serum cholesterol levels.
  • pressures when expressed as "psi" are pressures relative to standard pressure.
  • 20 psi as used above means 20 psi in excess of standard pressure.
  • Standard pressure is about 14.7 pounds per square inch absolute.
  • Solvents other than ethyl acetate may be used to prepare a mixture of saturated phytosterols from a mixture of unsaturated phytosterols derived from tall oil. Such other solvents include ethanol and isopropanol. However, ethyl acetate has been found to produce surprisingly unique results.
  • ethyl acetate With ethyl acetate, it is possible not only to achieve conversion ratios above 97% and approaching 99% or higher but, in so doing, to produce a resulting saturated phytosterol mixture that has particularly high purity. Moreover, it has been found that a saturated phytosterol mixture produced with ethyl acetate as the solvent can be filtered and dried (e.g. to less than 50 ppm solvent residue) substantially more efficiently than when produced with solvents such as ethanol or isopropanol.
  • the FIGURE is a representation of a gas chromatograph (GC) trace obtained upon hydrogenation of a raw material mixture of phytosterols as described below, in part serving to illustrate results that are achieved when (in accordance with the present invention) ethyl acetate is used as the hydrogenation solvent, and also serving to illustrate results that are achieved when (not in accordance with the present invention) ethanol or ispropanol is used as the hydrogenation solvent.
  • GC gas chromatograph
  • raw material phytosterol mixtures that are isolated from tall oil typically will include both unsaturated and saturated phytosterols.
  • Table 1 below indicates characteristics of raw material crystalline mixes that may be derived from softwood trees indigenous to northern British Columbia (including spruce, lodgepole pine and sub-alpine fir). TABLE 1
  • Phytosterols > 95% by weight ⁇ -sitosterol 55 - 60% by weight ⁇ -sitostanol 12 - 18% by weight campesterol 12 - 17% by weight campestanol 2 - 4% by weight other sterols ⁇ 3% by weight
  • Phytosterol mixtures as indicated in Table 1 may be used in the manufacture of cholesterol lowering agents without any hydrogenation step. However, hydrogenation is desirable because ⁇ -sitostanol is recognized as having an efficacy significantly higher and an absorption rate significantly lower than ⁇ -sitosterol.
  • Raw material mixtures as indicated in Table 1 are themselves considered useful to be used directly for the manufacture of food additives or dietary supplements that have serum cholesterol lowering properties.
  • hydrogenation is desirable because ⁇ -sitostanol is recognized as having particularly high efficacy and because ⁇ -sitosterol is the most plentiful unhydrogenated phytosterol.
  • the temperature used in accordance with the invention is greater than 35 deg. C, and preferably about 40 deg. C. or higher where the percent conversion is in the high 90% range.
  • Reduced drying time represents a significant advantage that ethyl acetate provides over solvents such as ethanol and isopropanol. However, it has also been found the use of ethyl acetate mitigates against impurities that tend to appear in the end product mixture when ethanol or isopropanol is used.
  • FIGURE is generally representative of GC traces that will be obtained upon hydrogenation of a raw material mixture like that indicated in Table 1. As shown, the trace includes three major peaks: Pea l Internal Standard (cholesterol)
  • Peak 4 to the right of peak 3 is representative of other sterols.
  • Peak 5 to the left of peak 1 represents undesirable impurities. Although there is a degree of uncertainty, it is thought to be generated by dehydroxylated forms of sterols (campestane and stigmastane).

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Heart & Thoracic Surgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Vascular Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Steroid Compounds (AREA)

Abstract

L'invention concerne un mélange faisant office de produit final renfermant essentiellement des phytostérols saturés préparé à partir d'un mélange de matières premières contenant des phytostérols issus de tallöl. Une partie importante du mélange à base de matières premières au moins se compose de phytostérols insaturés. Le procédé consiste à hydrogéner le mélange à base de matières premières dans un solvant comprenant essentiellement un acétate d'éthyle en présence d'un catalyseur d'hydrogénation, à filtrer et sécher le produit obtenu de manière à séparer le mélange de phytostérols saturés du solvant et à laisser un reste de solvant dans le mélange ne dépassant pas une quantité souhaitée. L'hydrogénation est effectuée à une température supérieure à 35 °C, de préférence à 40 °C au moins, et à une pression supérieure à la pression normale, de préférence 20 psi au moins. Le mélange ainsi obtenu, contenant des phytostérols saturés, peut être utilisé à de multiples fins, notamment dans la fabrication d'additifs alimentaires ou de compléments diététiques et a pour objectif de faciliter le réduction du taux de cholestérol stérique.
PCT/CA2000/000357 1999-04-06 2000-04-05 Preparation de phytosterols satures Ceased WO2000059921A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU36509/00A AU3650900A (en) 1999-04-06 2000-04-05 Preparation of saturated phytosterols

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA2,267,929 1999-04-06
CA 2267929 CA2267929A1 (fr) 1999-04-06 1999-04-06 Preparation de phytosterols satures

Publications (1)

Publication Number Publication Date
WO2000059921A1 true WO2000059921A1 (fr) 2000-10-12

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PCT/CA2000/000357 Ceased WO2000059921A1 (fr) 1999-04-06 2000-04-05 Preparation de phytosterols satures

Country Status (3)

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AU (1) AU3650900A (fr)
CA (1) CA2267929A1 (fr)
WO (1) WO2000059921A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100440613B1 (ko) * 2001-04-20 2004-08-16 주식회사 유엘바이오텍 식물성스테롤과 생 플라보노이드의 결합체를 이용한 혈중콜레스테롤 저하제의 제조방법과 이에 의해 제조한 혈중콜레스테롤 저하제
WO2010010227A1 (fr) * 2008-07-25 2010-01-28 Raisio Nutrition Ltd Procédé d’hydrogénation amélioré

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5244887A (en) * 1992-02-14 1993-09-14 Straub Carl D Stanols to reduce cholesterol absorption from foods and methods of preparation and use thereof
WO1998038206A1 (fr) * 1997-02-26 1998-09-03 Raisio Benecol Ltd. Procede pour preparer des esters de stanol
WO1999056558A1 (fr) * 1998-05-06 1999-11-11 Raisio Benecol Oy Compositions de phytosterol

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5244887A (en) * 1992-02-14 1993-09-14 Straub Carl D Stanols to reduce cholesterol absorption from foods and methods of preparation and use thereof
WO1998038206A1 (fr) * 1997-02-26 1998-09-03 Raisio Benecol Ltd. Procede pour preparer des esters de stanol
WO1999056558A1 (fr) * 1998-05-06 1999-11-11 Raisio Benecol Oy Compositions de phytosterol

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 70, no. 24, 16 June 1969, Columbus, Ohio, US; abstract no. 109125, ALLAIS, JEAN P. ET AL: "Preparation of pure.beta.- sitosterol by thin-layer chromatography on silver nitrate impregnated alumina" XP002145680 *
QUAL. PLANT. MATER. VEG. (1968), 16(1-4), 215-22 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100440613B1 (ko) * 2001-04-20 2004-08-16 주식회사 유엘바이오텍 식물성스테롤과 생 플라보노이드의 결합체를 이용한 혈중콜레스테롤 저하제의 제조방법과 이에 의해 제조한 혈중콜레스테롤 저하제
WO2010010227A1 (fr) * 2008-07-25 2010-01-28 Raisio Nutrition Ltd Procédé d’hydrogénation amélioré

Also Published As

Publication number Publication date
AU3650900A (en) 2000-10-23
CA2267929A1 (fr) 2000-10-06

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