Classifications

• • 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 invention is in the field of food additives and relates to a new process for the simplified production of phytosterols.
• Phytosterols and their esters have hypocholesterolemic properties, i.e. these substances are able to reduce the cholesterol level in the blood. They are therefore used as food additives, for example for the production of margarine, frying oils, sausages, ice cream and the like.
• the extraction of sterols and other unsaponifiable components, e.g. Tocopheroias, from distillates that are obtained in the deacidification of vegetable oils have already been described in various ways in the patent literature. Representative here are the publications EP-A2 0610742 (Hoffmann-LaRoche), GB-A1 2145079 (Nisshin Oil Mills Japan) and EP-A1 0333472 (Palm Oil Research and Development Board).
• the object of the present invention was to provide phytosterols in high yields and to simplify existing methods of the prior art.
• the invention relates to a process for obtaining phytosterols from mixtures with fatty acid esters and methanol by crystallization, filtration, washing and drying known per se, which is characterized in that the methanol, based on the sterols, in amounts of 25 to 75% by weight. % uses.
• the crystallization temperature of the sterols is significantly influenced by the methanol content in the reaction mixture.
• the melting temperature of a mixture with a methanol content of 30% by weight increases from 65 to 78 ° C compared to an alcohol-free fraction. This not only leads to a simplification of the process and an improvement in the energy balance, in the subsequent work-up, significantly higher yields are also achieved.
• the invention includes the finding that the increase in the crystallization temperature is not a linear function of the methanol content, but a rapid decrease can be observed again at contents above about 75% by weight.
• a sterile-rich fraction can be produced by transesterification of residues from the deacidification of vegetable oils and subsequent workup in the manner known from EP-B1 0656894.
• Suitable starting materials are distillation residues which are obtained, for example, as so-called damper condensates in the production of fatty acid methyl esters based on rapeseed oil, soybean oil or, in particular, sunflower oil.
• Tall oil pitch, particularly pitch obtained from birch bark, is also suitable.
• the process is particularly suitable for the production of sterols based on vegetable oils that only contain a small proportion of ⁇ -sitosterols. Therefore, phytosterol-rich fractions from the transesterification of rapeseed oil (“rapeseed sterols”) or soybean oil (“soyasterines”) serve as the preferred starting material.
• the crystallization of the sterol fractions takes place in a manner known per se, ie the hot mixtures (approx. 90 to 100 ° C.) are slowly cooled down to approx. 10 ° C. in a crystallizer.
• alkaline catalyst contained in the mixture can be neutralized beforehand from the transesterification, for example by adding citric acid.
• raw sterols instead of the transesterification products, to add methanol and optionally methyl esters and to concentrate them in the manner described. If desired, the raw sterols can also be washed with methyl ester fractions; Small amounts of product are lost, but a sustainable color improvement is achieved. The resulting phytosterols are then separated and purified in a manner known per se, ie filtered off, washed free of ester and dried to constant weight.
• Comparative Example V1 A rapeseed methyl ester fraction was used as the starting material, which, based on the content of free and bound sterols, additionally contained 100% by weight of methanol. The mixture was continuously cooled from approximately 100 ° C. to 10 ° C., the first crystals already beginning to separate at 68 ° C. After completion of the crystallization, the crystals were filtered off, washed free of methyl ester with methanol and dried to constant weight. The yield was - based on the sterol content in the transesterification product - 78% by weight.
• Example V1 was repeated using a mixture which, based on the amount of sterol, contained 200% by weight of methanol. Crystallization only started at 63 ° C., the yield was 72% by weight. The products have a Hazen color number of 798 or a Gardner color number of 4.4 in 10% by weight ethanolic solution.
• Example V1 was repeated using a mixture which, based on the amount of sterol, contained 300% by weight of methanol. Crystallization only started at 56 ° C., the yield was 68% by weight.
• Example V1 was repeated using a mixture which, based on the amount of sterol, contained 30% by weight of methanol. Crystallization started at 78 ° C, the yield was 92% by weight
• Example 2 100 g of a crude soyasterin mixture (sterol content: 83% by weight) was dissolved at 90 ° C. in 186 g of coconut fatty acid methyl ester and an amount of methanol was added such that the weight ratio of sterol to methanol was 2: 1. After lowering the temperature, the first sterol crystals were already deposited at 74 ° C. After the crystallization had ended, the crystals were filtered off, washed free of methyl ester with methanol and dried. The resulting fraction showed a purity of 93.7% by weight.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Steroid Compounds (AREA)
• Saccharide Compounds (AREA)

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Citations (6)

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• 1999
  • 1999-04-09 DE DE19916034A patent/DE19916034C1/de not_active Expired - Fee Related
• 2000
  • 2000-03-31 DE DE50004569T patent/DE50004569D1/de not_active Expired - Lifetime
  • 2000-03-31 AU AU45411/00A patent/AU762975B2/en not_active Ceased
  • 2000-03-31 CA CA002369977A patent/CA2369977C/en not_active Expired - Lifetime
  • 2000-03-31 WO PCT/EP2000/002849 patent/WO2000061603A1/de not_active Ceased
  • 2000-03-31 JP JP2000611545A patent/JP4796695B2/ja not_active Expired - Lifetime
  • 2000-03-31 AT AT00926783T patent/ATE255124T1/de active
  • 2000-03-31 NZ NZ514667A patent/NZ514667A/xx not_active IP Right Cessation
  • 2000-03-31 EP EP00926783A patent/EP1169335B1/de not_active Expired - Lifetime
• 2004
  • 2004-07-22 US US10/896,486 patent/US7244856B2/en not_active Expired - Lifetime

Patent Citations (6)

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