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Process for Producing Phytosterols By Europäisches Patentamt *EP001226156B1* (19) European Patent Office Office européen des brevets (11) EP 1 226 156 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C07J 9/00 of the grant of the patent: 24.08.2005 Bulletin 2005/34 (86) International application number: PCT/JP2000/007752 (21) Application number: 00971771.1 (87) International publication number: (22) Date of filing: 02.11.2000 WO 2001/032681 (10.05.2001 Gazette 2001/19) (54) PROCESS FOR PRODUCING PHYTOSTEROLS BY SAPONIFICATION IN AN ALCOHOL/WATER SOLVENT VERFAHREN ZUR HERSTELLUNG VON PHYTOSTEROLE DURCH VERSEIFUNG IN EINEM AUS WASSER/ALKOHOL BESTEHENDEN LÖSUNGSMITTEL PROCEDE DE PRODUCTION DE PHYTOSTEROLS PAR SAPONIFICATION DANS UN SOLVANT ALCOOL/EAU (84) Designated Contracting States: • DATABASE PAPERCHEM2 [Online] Institute of DE FR GB Paper Science and Technology (IPST); 1975 NEKRASOVA, V. B. ET AL: "SEPARATION OF (30) Priority: 04.11.1999 JP 31361899 PHYTOSTEROL FROM AQUEOUS ALCOHOL SOLUTIONS OF SAPONIFIED PITCH BY (43) Date of publication of application: CRYSTALLIZATION USING THE LTA METHOD" 31.07.2002 Bulletin 2002/31 retrieved from STN Database accession no. 2764 XP002161740 & IZV. VUZ, LESNOI ZH., (1974) (73) Proprietor: KAO CORPORATION VOL. 17, NO. 6, PP. 105-108. [RUSS.]., Tokyo 103-8210 (JP) • DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; (72) Inventors: 1995 MAZGAJSKA, IRENA ET AL: "Method of • HATTORI, Yasuyuki, c/o Kao Corporation, obtaining sterols from fatty raw materials" Reser Lab retrieved from STN Database accession no. Wakayama-shi,Wakayama 640-8580 (JP) 122:161041 XP002161741 & PL 162 894 B • HORIO, Masamitsu, c/o Kao Corporation, (INSTYTUT CHEMII PRZEMYSLOWEJ, POL.) 31 Resear Lab January 1994 (1994-01-31) Wakayama-shi, Wakayama 640-8580 (JP) • DATABASE BIOSIS [Online] BIOSCIENCES • KONO, Jun, c/o Kao Corporation, INFORMATION SERVICE, PHILADELPHIA, PA, Research Laborat US; 1993 BIEDERMANN MAURUS ET AL: Wakayama-shi, Wakayama 640-8580 (JP) "Transesterification and on-line LC-GC for determining the sum of free and esterified (74) Representative: HOFFMANN EITLE sterols in edible oils and fats." Database Patent- und Rechtsanwälte accession no. PREV199396027425 XP002161742 Arabellastrasse 4 & FETT WISSENSCHAFT TECHNOLOGIE, vol. 81925 München (DE) 95, no. 4, 1993, pages 127-133, ISSN: 0931-5985 • DATABASE WPI Section Ch, Week 197414 (56) References cited: Derwent Publications Ltd., London, GB; Class US-A- 2 835 682 US-A- 3 840 570 B01, AN 1974-25758V XP002161743 & JP 49 005959 A (NISSHIN OIL MILLS LTD), 19 January 1974 (1974-01-19) cited in the application Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 226 156 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 226 156 B1 Description Technical Field 5 [0001] The present invention relates to a method of efficiently saponifying a fatty acid ester contained in a crude phytosterol composition derived from a vegetable fat and/or oil. Accordingly, it relates to a process for producing a highly pure phytosterol by using the saponified solution. Background Art 10 [0002] Phytosterols are not only used in clinical administration etc. expected to have an effect of reducing cholesterols in blood but also utilized as raw or starting materials for medicines as substitutes for cholesterols or as emulsifiers or emulsion-stabilizers in cosmetics and foods. [0003] Sterols are contained in vegetable fats and oils such as a soybean oil, a rapeseed oil, a rice bran oil, a palm 15 oil, a palm kernel oil and a coconut oil. There has been practically used a producing process by extraction and/or purification thereof from a deodorized concentrate etc. generated upon purification of fats and oils. JP-B 52-8309 describes a general method of extracting therefor. The method comprises adding a lower alcohol to a deodorized distillate of fats and oils in order to esterify with an acid catalyst, then washing with water to remove the acid catalyst, adding an additional lower alcohol and an alkali catalyst to carry out a transesterification reaction, further being calmly 20 left overnight to precipitate crystals, separating the crystals by filtration, and washing and drying with hexane, in order to obtain phytosterols. And, it is described that the purity of the obtained phytosterols is 82 %. However, the purity of the purified phytosterols is too low to be used directly as pharmaceutical preparations and food additives. [0004] A method of separating crude phytosterol from tall oil, which is based on the crystallization of sterols from aqueous alcohol solutions of tall oil is described in Izv. vuz. Lesnoi Zh. 17, No. 6 (1974), pages 105-108. A process 25 for preparing sterols from tall oil pitch is also described in US 3,840,570. A method of obtaining sterols from fatty raw materials is disclosed in PL 162894 B. US 2,835,682 concerns the isolation of sterols from sterol containing materials by fractionation procedures. [0005] When methanol is particularly used as the lower alcohol for an esterification or transesterification reaction, methyl esters of C6-28 fatty acids are contained as impurities in the resultant phytosterols. If these fatty acid methyl 30 esters can be removed, a highly pure phytosterol can be obtained. [0006] As a method of removing them, there is exemplified a saponification with an alkali. This method comprises converting a fatty ester with an alkali into a soap, precipitating a sterol crystal by cooling the soap, separating the crystal, and re-precipitating and drying the resultant crystal, in order to obtain a highly pure phytosterol. In this method, it is important how the saponification reaction is carried efficiently out, but, because of a low rate of saponification, the 35 conventional method is not practical. Accordingly, the purification thereof by re-crystallizing repeatedly has been generally used in spite of an increasing number of steps. The problem of this method is that the yield of phytosterols is decreased thorough a number of steps, thus making the method uneconomical in respect of recovery. 40 Disclosure of Invention [0007] The object of the present invention is to provide a method of obtaining a highly pure phytosterol practically and efficiently from a crude phytosterol composition derived from a vegetable fat and/or oil. [0008] The present invention relates to a method of saponifying a fatty acid ester contained in a crude phytosterol 45 composition having an acid value of 10 or less with an alkali in a mixed solvent of water and a lower alcohol represented by at least one member of methanol, ethanol, isopropanol, n-propanol and a linear or branched butanol or a mixture of two or more thereof. It relates also to a process for producing a phytosterol, which comprises, after this saponifying method, cooling the reaction solution to precipitate crystals of the phytosterol and separating the obtained crystals. [0009] In the present invention fatty acid esters, contained in a raw material of phytosterol, can be saponified and 50 dissolved in the solvent mixture to remove the fatty acid esters and obtain a concentrated product of phytosterol. The invention relates to a process for producing phytosterol by cooling the above-shown saponification product mixture to obtain crystals of phytosterol and separating the crystals. [0010] The present invention provides a process for producing a concentrated phytosterol product by treating a raw material with the above-mentioned saponifying process. The raw material may be fat and/or oil including fatty acid 55 esters such as methyl ester. The product mixture of the saponification of the invention may be further purified by re- crystallization of natural phytosterol and the phytosterol product obtained by the saponification. [0011] The invention is a purifying method of phytosterol and a concentrating method of a phytosterol in a fat and/ or oil. 2 EP 1 226 156 B1 [0012] The present invention also provides a process for preparing a phytosterol product, comprising treating a crude phytosterol product having an acid value of 10 or less including a fatty acid ester(s) with an alkali in a solvent mixture of a lower alcohol represented by at least one member of methanol, ethanol, isopropanol, n-propanol and a linear or branched butanol or a mixture of two or more thereof and water to saponify the fatty ester(s) contained in the crude 5 phytosterol product. It is preferable that this process further comprises cooling the reaction solution to precipitate crys- tals of the phytosterol and separating the obtained crystals. [0013] The starting crude phytosterol product used by the process of the invention may be in advance treated by (A) crystallizing the phytosterol in a solvent mixture of an organic solvent and water or (B) crystallizing the fatty acid esters in a lower alcohol at a temperature of 1 to 40 °C, separating the crystals out and taking the lower alcohol solution 10 including phytosterol. A more concentrated phytosterol product can be obtained this way. Modes for Carrying out the Invention [0014] The phytosterols in the present invention refer to sterols, contained in vegetable fats and oils, such as β- 15 sitosterol, stigmasterol, campesterol and brassicasterol. A crude phytosterol composition refers to a phytosterol com- position containing at least a fatty acid ester as impurity. The vegetable fat and/or oil as a raw material of the phytosterol is not limited in particular, but they are preferably a soybean oil, a rapeseed oil, a palm kernel oil, a coconut oil, a palm oil or the like.
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