Colloid systems and wetting agents; subcombinations thereof; pro – Continuous liquid or supercritical phase: colloid systems;... – Primarily organic continuous liquid phase
Reexamination Certificate
1998-03-09
2002-03-12
Metzmaier, Daniel S. (Department: 1712)
Colloid systems and wetting agents; subcombinations thereof; pro
Continuous liquid or supercritical phase: colloid systems;...
Primarily organic continuous liquid phase
C516S073000, C516S918000, C424S776000, C426S430000, C554S014000, C536S123130, C536S128000
Reexamination Certificate
active
06355693
ABSTRACT:
This application is filed under 35 U.S.C. §371 and is based on PCT International Application No. PCT/SE96/01146 which was filed on Sep. 13, 1996.
TECHNICAL FIELD
This invention relates to an industrially applicable process for preparing a fractionated oil from crude vegetable oils, preferably from cereals and grains, the fractionated oil which is obtainable by said process, and to the use of the fractionated oil as a surface active agent in food, cosmetics and pharmaceutical products.
1. Background of the Invention
The production of vegetable oils from various sources, such as soybeans, rapeseed and corn, is based on extraction with as hexane and subsequent refining of the crude extracts to edible oils. The first step in the refining sequence is the so-called degumming, which step serves to separate the phosphatides by the addition of water. The material precipitated by degumming is separated and further processed to mixtures used under the name of lecithins. The commercial lecithins, such as soybean lecithin and sunflower lecithin, are semi-solid or very viscous materials, which consist of a mixture of polar lipids, mainly phospholipids, and oil, mainly triglycerides. These lecithins are by-products from the production of the corresponding vegetable oils and have, after further treatment and purification, found use as surface active materials in many applications, including food, cosmetics and pharmaceutical products.
Wide ranges of conditions for the degumming process are reported in the literature, all of them based on the addition of water, or water solutions, to the crude oils to hydrate the phosphatides and make them insoluble in the oil. Further processing of this crude precipitate, the so called lecithin sludge, involves centrifugation, that is desliming, bleaching by treatment with hydroperoxide and benzoyl peroxide, heat treatment, such as drying or cooking, to give the crude lecithin, which is used as ingredient mainly in food products. The crude lecithin can be further processed in various ways, the most common being purification, such as filtration and adsorption, deoiling, for instance by acetone fractionation to remove the neutral lipids, and fractionation, for instance by means of alcohol treatment to separate alcohol-soluble and alcohol-insoluble components. The established procedure for producing lecithin is shown in Figure.
The methods outlined above are mainly used to produce lecithins from oil crops, such as soybeans, sunflower, rapeseed, corn and cottonseed. In principle all of these are polar lipid rich oils, characterized by being phospholipid rich, particularly phosphatidylcholine rich, consisting of 40-60% oils and 60-40% polar lipids. The content of glycolipids in said lecithins is relatively small, but varies with the source, and the process is designed to give as high a yield as possible of phospholipids at the expense of the glycolipids and other components. Other sources than oil crops, for example cereals, contain more glycolipids than phospholipids.
Glycolipids are well known constituents of plant cell membranes. The most important classes of these contain one to four sugars linked glycosidically to diacylglycerol. The two most abundant classes contain one and two galactose units, respectively, and the commonly used nomenclature and abbreviations of these are mono- and digalactosyldiglyceride, MGDG and DGDG, sometimes referred to as galactolipids. The general structure of digalactosyldiglyceride, DGDG, is outlined below.
The commercial lecithins, such as lecithins produced from soybean oil, sunflower oil, and rapeseed oil, consist mainly of phospholipids, of which phosphatidylcholine (PC) and phosphatidylethanolamine (PE) are most abundant. PC is the most well characterized class of polar lipids and PC rich materials have found a wide range of industrial applications. Glycolipids have been identified as minor constituents of these lecithins. From an industrial viewpoint it is of a general interest and importance to have access to materials rich in polar lipids other than PC, and also, materials rich in polar lipids other than phospholipids, particularly glycolipids. This relates to the fact that PC and other phospholipid classes are charged, that is contain anionic or zwitterionic functional groups, while the glycolipids are non-charged.
2. Prior Art
There are numerous descriptions in the literature on the use, of lecithins, purified lecithins and phospholipids as surface active ingredients, see for instance “Lecithins: Sources, Manufacture & Uses”, B. F. Szuhaj, Editor, American Oil Chemists' society, 1989.
CA 1102795 describes a method of isolating polar lipids from cereal lipids by the addition of at least 50% by weight of water. This method is a modified degumming in the sense that it utilises the principle of adding water to a crude oil mixture.
In Cereal Chem., 1977, vol. 54(4), pp 803-812, lipids were extracted from oat groats by means of diethyl ether and said ether extract evaporated to dryness and reextracted with water saturated n-butanol. After another evaporation the mixture was taken up in chloroform and the lipids obtained were analysed and recorded as bound lipids.
EP 0 290 156 refers to a process for extracting oilseeds by means of a combination of a polar and a non-polar extraction solvent in a counter-current system aiming at a high oil recovery.
Galactolipids, primarily DGDG and DGDG-rich materials have been investigated and found to be surface active material of interest in industrial applications such as food, cosmetics, and pharmaceutical products.
WO 95/20943 describes the use of DGDG-rich material, a “galactolipid material”, as an emulsifier in oil-in-water emulsions for pharmaceutical, nutritional and cosmetic use. WO 95/20944 describes the use of said “galactolipid material” as a bilayer-forming material in polar solvents for pharmaceutical, nutritional and cosmetic use; and WO 95/20945 describes the use of the “galactolipid material” as a lipophilic carrier for pharmaceutical, nutritional and cosmetic use. The DGDG-rich material, the “galactolipid material”, utilized in said applications was prepared from cereals by extraction of the lipids with ethanol and a subsequent purification on a chromatographic column to pure DGDG or a DGDG-rich fraction of polar lipids. The use of chromatography on a large-scale is expensive compared to the production of, for-example, soybean lecithin by degumming, and there is need for a cheaper way to produce polar lipid rich materials for industrial use, particularly glycolipid rich materials.
DESCRIPTION OF THE INVENTION
The present invention is related to a novel method for producing a fractionated vegetable oil from a plant material.
The present invention provides a novel method for producing purified lecithins or a polar lipid rich fractionated oil, particularly rich in glycolipids, which without further purification can be directly utilized as a surface active agent, for example as an emulsifier in food, cosmetics and pharmaceutical products. The method of the present invention is designed to maintain the concentration of the glycolipids, which implies that the polar lipid rich fractionated vegetable oils obtainable in accordance with the invention are glycolipid rich, particularly digalactosyldiglyceride rich oils. The concentration of the polar lipids can be controlled by process parameters.
In the novel, industrially applicable method of the invention, for producing a polar lipid rich fractionated vegetable oil, a plant material is extracted with a non-polar solvent, and the solvent is evaporated giving a crude oil comprising non-polar and polar lipids, which crude oil is further purified. The method of the invention is characterized in that the crude oil is mixed with an alcohol at a controlled temperature, the alcoholic phase is separated and evaporated and a polar lipid rich fractionated vegetable oil is obtained.
The method of the invention can be described by the following steps:
(a) extraction of a plant material with a non-polar solvent and evaporation of the solven
Herslöf Bengt
Kroon Carl-Gunnar
Tingvall Per
Hoffmann & Baron , LLP
Metzmaier Daniel S.
Scotia Lipidteknik AB
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