TW200811280A - Product and process - Google Patents

Abstract

The present invention relates to processes for separating a feed material into soluble and insoluble components, by contacting a feed material and a solvent and subsequently separating the solvent containing the soluble components from the insoluble components, wherein the feed material comprises one or more of: at least 1% by mass phosphatidyl serine, at least 1% by mass sphingomyelin, at least 0.3% by mass acylalkylphospholipids and/or plasmalogens, at least 0.5% by mass aminoethylphosphonate and/or other phosphonolipids, at least 1% by mass cardiolipin, and at least 0.3% by mass gangliosides; and wherein the solvent comprises: supercritical or near-critical CO2, and a co-solvent comprising one or more C1-C3 monohydric alcohols, and water, wherein the co-solvent makes up at least 10% by mass of the CO2, and the water content of the co-solvent is 0 to 40% by mass. The present invention also relates to processes for separating a feed material into soluble and insoluble components, comprising contacting a feed material and a first solvent and subsequently separating the first solvent containing the first soluble components from the first insoluble components, wherein the feed material comprises one or more of: at least 1% by mass phosphatidyl serine, at least 1% by mass sphingomyelin, at least 0.3% by mass acylalkylphospholipids and/or plasmalogens, at least 0.5% by mass aminoethylphosphonate and/or other phosphonolipids, at least 1% by mass cardiolipin, or at least 0.3% by mass gangliosides; and wherein the first solvent comprises supercritical or near-critical CO2. The process then provides contacting the first insoluble components with a second solvent and subsequently separating the second solvent containing the second soluble components from the second insoluble components, wherein the second solvent comprises supercritical or near-critical CO2, and a co-solvent comprising one or more C1-C3 monohydric alcohols, and water, wherein the co-solvent makes up at least 10% by mass of the CO2, and the water content of the co-solvent is 0 to 40% by mass.

Description

200811280 IX. Description of the invention: [Technical street field to which the invention pertains] The present invention relates to a separation method. More particularly, the present invention relates to a separation containing phospholipids and/or glycolipids (for example, including phospholipid tyrosine, ganglioside, cardiolipin, sphingomyelin, plasmalogen, alkyl sulfhydryl) A method of a lipid material of a phospholipid, a phospholipid, a cerebroside or a combination thereof. [Prior Art] Phospholipids are the main components of all biofilms, and include phosphoglycerides (phospholipid choline (PC), phospholipids, ethanolamine (PE), phospholipids (PI), cardiolipin (CL), phospholipids. Serine, plasmalogen (pL), phospholipid (pp), alkylmercaptophospholipid (ALP); and sphingolipids (such as sphingomyelin (SM) and neuroglycosylaminoethylphosphonate (CAEP) )) Gangliosides are glycolipids that regulate cell signaling events in the plasma membrane. These components are particularly important in immune and neurodegenerative disorders. Cerebrosides are important components in animal muscle and neuronal membranes. The squamous cell and ganglion rouge are involved in cellular signal transduction events leading to, for example, cell death (apoptosis), cell growth, cell proliferation, and cell differentiation. Some of these components are reasonably soluble in milk, Soybean products, eggs, animal glands, and § official, marine animals, plants, and other sources. One source of such ingredients is known to contain useful amounts of sphingomyelin, ceramide, gangliosides, and phospholipids. Cow of lysine Lipid globule membrane (MFGM). Another source of such wounds is the green shellfish known to contain a quantity of plasmalogen, decyl ruthenium ruthenium and neuroglycosylethylphosphonate. Doc 200811280 : The moon 曰 神 已 has been involved in providing many health benefits, including brain health, skin storage South gt; « _ w , , ' ", treatment > Q treatment, anti-infection, wound healing, intestinal c microorganisms It can improve the anti-cancer activity, reduce arthritis, improve cardiovascular health and treat metabolic syndrome. It can also be used in sports nutrition. *The sputum is an important component of the lining of the granule n, which is usually present in the myocardium and bone. Muscle metabolism in active cells. It acts as an insulator and stabilizes the activity of protein complexes important for the electron transport chain. • Existing methods of cleavage from such compounds rely on the use of chromatographic techniques, which are slow and expensive to operate. Methods. Such techniques may also require the use of solvents that are inappropriate and/or undesirable in products for sedation or human use: for example, Palaci〇aWang [i] describes an extraction using acetol alcohol, k Using methanol/chloroform separation and extracting the fat from the egg yolk to Kang and Row [2] describes a liquid chromatography method that separates the soybean source from the ^^ and the mixture. It may be expensive to implement the method on an industrial scale. Moreover, it also uses hexane, methanol and isopropanol as solvents. Keams et al. [3] describe a method for purifying yolk-derived PC from 叩 using a mixture of B guess, fluorocarbon and fluorocarbon. Or such solvents are undesirable for medical use. Due to the benefits of treatment and consumption, the use of eh supercritical fluid extraction has become increasingly popular. By reducing the force, c〇2 returns to a gaseous state and can be easily derived from the final product. t removes C〇2 to give a completely solvent-free product. It is believed that the extract is more natural than the extract produced using other solvents, and the use of alternative organic solvents is also provided by reducing the use of organic solvents. Environment ^ Benefits. A disadvantage of supercritical c〇2 treatment is that many compounds are soluble in c〇2. 12D458.doc 200811280 has low resolution and can only extract neutral lipids. It is known that the extraction of certain phospholipids choline can be carried out using co2 with an organic co-solvent such as ethanol and the extraction of phospholipids ethanolamine can be carried out to a much lesser extent. For example, Teberikler et al. [4] describe a method for extracting PC from soy lecithin. Using 10% ethanol in CO 2 at 60 ° C, they found it easy to extract PC, while the extraction of PE and PI was extremely low. Extraction at 12.5% ethanol at 80 ° C? (1; the solubility is increased by 4 times.] \4〇11^311 & 14 et al. [5] describe a method for extracting phospholipids from soy flakes. After first extracting neutral lipids using CO 2 at 320 bar, they It was found that the use of a 10% ethanol co-solvent at a pressure of 194 to 689 bar resulted in some extraction of PC, PE, PI and phosphatidic acid (PA). Selective extraction of PC under certain conditions, but at higher temperatures and pressures Achieving some of the grass and PE. For industrial applications, the pressure required to achieve good extraction is unrealistically high, and the high temperatures (80 ° C) used can cause degradation of polyunsaturated fatty acids. Taylor et al [ 6] A method is described in which a soybean flake is first extracted using only CO 2 at 80 ° C and 665 bar, and then a soybean flake is extracted using a CO 2 having 15% ethanol to obtain a phospholipid mixture, which is separated by an alumina column. Temperature and pressure are too high for practical applications. In these articles, feedstocks derived from soy contain no detectable levels of SM, CL, GS or PS.

Tanaka and Sakaki [7] describe a method of extracting fat by using C〇2 and a waste tuna shaving as a co-solvent. They described the use of 5% ethanol in C02 and the extraction of DHA-containing phospholipids by pre-soaking the salmon fillets in pure ethanol followed by CO2 extraction. The phospholipids obtained in this method are not specifically described and the fractionation of different phospholipids is not described. In addition, phospholipids 120458. doc 200811280 a relatively small fraction of the two materials, thus requiring the use of large σσ to produce a small yield of cans. It: =8] describes the use of C02 and 3% ethanol... Π: yellow. The co-solvent is used to obtain a higher extraction ratio of glycerol tri-fed = a small amount of phospholipid extract (up to 17% of the fractionation of the lecithin in the extract).

=本 = When referring to the special (4), other external literature or / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / References to such external documents or sources of such information are not to be construed as an admission that such documents or such information sources are in the form of a prior art or a part of the general knowledge in the art. It is an object of the present invention to provide a method of producing a product containing a desired amount of a particular phospholipid and/or ganglioside and/or cerebroside or at least to provide the public with a useful choice. SUMMARY OF THE INVENTION Accordingly, the present invention provides a method of separating a feed material into a soluble component and an insoluble component, comprising: (a) providing a feed material comprising one or more of the following: (0 at least 1 (%) at least 1% by mass of sphingomyelin; (out) at least 0.3% by mass of mercaptoalkylphosphorus and/or acetal; (iv) at least 〇 5% by mass of aminoethylphosphonate and/or other phospholipids; (ν) at least 1% by mass of cardiolipin; 120458.doc 200811280 (vi) at least 〇·3 mass. (b) providing a solvent comprising: (i) supercritical or near-critical C〇2; and (11) a cosolvent comprising one or more Ci-C3 monohydric alcohols and water, wherein the cosolvent is C〇 The mass of 2 accounts for at least ·, and the water content of the cosolvent is 0 to 40% by mass; (c) contacting the feed material with the solvent and then separating the solvent containing the soluble component from the insoluble component; (d) separating as appropriate Soluble ingredients and solvents. The feed material preferably contains more than 1% phospholipid quinic acid. The feed material preferably contains large 2% phospholipid yrosine acid. The feed material preferably contains more than 5% linalic acid. Or 'feed material contains more than 1% sphingomyelin. Feed material preferably contains more than 53⁄4 The sphingomyelin. The feed material preferably contains more than i5% of the sphingomyelin. Or the 'feed material contains more than 1% cardiolipin. The feed material preferably contains more than 2% cardiolipin. The feed material preferably contains Greater than the heart structure. Or 'Feed material contains more than 3%·3% of ganglion fat. The feed material preferably contains more than 1% ganglioside. The feed material preferably contains more than 2〇/〇. The ganglion rouge. Alternatively, the feed material comprises greater than 0.5% mercaptoalkyl phospholipids and/or acetal scales. The feed material preferably comprises greater than 2% mercaptoalkyl phospholipids and/or acetal scales. The feed material preferably comprises a mercaptoalkyl phospholipid and/or a plasmalogen greater than 〇D/❶. 120458.doc

II 200811280 or 'Feeding material containing more than 5% 5% of aminoethylphosphonate and / or other phospholipids. The feed material preferably comprises greater than 5% of an aminoethylphosphonate and/or other phospholipid. The feed material preferably comprises greater than 20% of the aminoethylphosphonate and/or other phospholipids. The present invention also provides a method of separating a feed material into a soluble component and an insoluble component, comprising:

(a) providing a feed material comprising one or more of the following: (1) at least 1% by mass of phospholipid lysine; (11) at least 1% by mass of a neurosheath; (in) at least 0.3% by mass of mercaptoalkylphospholipid and/or plasmalogen; (iv) at least 0.5% by mass of aminoethylphosphonate and/or other phospholipid; (v) at least 1% by mass of cardiolipin Or (vi) at least 33% by mass of ganglioside; (b) providing a first solvent comprising supercritical or near-critical co2; (c) contacting the feed material with the first solvent and then containing The first solvent of a soluble component is separated from the first insoluble component; (4) separating the first soluble component and the first solvent as appropriate; (e) providing a second solvent comprising: (1) supercritical or near critical c〇 2; and (ii) comprising a co-solvent in which the co-solvent is 0 to 40% by mass of CO; or a co-solvent of a plurality of CrC3-alcohols and water, the mass of 2 accounts for at least 1% by weight, and the water content of the cosolvent () Contacting the No> gluten component with the second solvent and then separating the second solvent containing the first merging to form a second solvent and the second insoluble component; 120458. Doc -12- 200811280 (g) Separate the second soluble component and the second solvent as appropriate. The first solvent preferably comprises a mixture of supercritical or near critical 0 〇 2 and less than 1 〇 % of CrC 3 -alcohol. The feed material preferably comprises greater than 1% phospholipid lysine. Feed the material more t匕δ greater than 2 鳞 鳞 酸 酸 酸. The feed material preferably contains more than $% phospholipid lysine. Alternatively, the feed material comprises greater than 1% sphingomyelin. The feed material preferably contains greater than 5% of sphingomyelin. The feed material preferably comprises a sphingomyelin of greater than 15 Å/〇. Or the 'feed material contains more than 1% cardiolipin. The feed material preferably contains greater than 2% cardiolipin. The feed material preferably contains more than a core filler. Or the 'feed material contains more than 3%·3% of the ganglion: y: fat. Feeding materials Che Yijia contains more than 1% of the ganglion: y: fat. Preferably, the feed material comprises gangliosides greater than 20/〇. Alternatively, the feed material comprises greater than 0.5% mercaptoalkyl-lipid and/or acetal fat-filling. The feed material preferably comprises greater than 2% mercaptoalkyl phospholipids and/or acetal greases. Preferably, the feed material comprises greater than 1% by weight of sulfhydryl-based fat and/or aldehyde phosphate. Alternatively, the feed material comprises greater than 0.5% of an aminoethylphosphonate and/or other phospholipid. The feed material preferably comprises greater than 5% of an aminoethylphosphonate and/or other phospholipid. The feed material preferably comprises greater than 2% by weight of an aminoethylphosphonate and/or other phospholipid. The feed material of the present invention may be derived from terrestrial animals, marine animals, terrestrial plants, marine plants or microorganisms such as microalgae, yeast and bacteria. Feeding 120458.doc -13 · 200811280 : It is better to be derived from jin sheep, goats, pigs, mice, cattle, horses, donkeys, American dried cows, cattle or humans. Luzhi and 牦Feeding materials are selected from the group consisting of: tissue and tissue parts - part milk, colostrum, colostrum, blood and liquid: feed material: preferably from dairy materials, soybean materials, *, move:; weaving, animal or official animal blood. Preferably, the feed material is selected from the group consisting of a composition comprising a lipid of the second product, comprising 4 egg yolks.

Quality composition. 3 egg "the composition and contains marine biolipid = the best way to feed the material in the invention method is the milk part. Feed g system distant from: white milk, white milk part, beta whey, beta whey part , whey whey, whey fraction, whey, whey fraction, colostrum and colostrum. The feed material may comprise a milk fat globule. The feed material is preferably in solid form. When it is solid, The feed material may be milled at a low temperature prior to contact with the solvent. The solvent of the present invention preferably comprises: (a) an alcohol selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, and mixtures thereof; 0-40% by volume/volume of water. The solvent preferably comprises between 0 and 20% by volume/volume of water. The solvent preferably comprises between 1 and 10% by volume/volume of water. The alcohol is preferably ethanol. The solvent in the method of the present invention preferably comprises a 95% aqueous solution of ethanol 0 120458.doc -14 - 200811280 A / The mass of the mixture in C 〇 2 is preferably between 5% and 6% by weight. Between 20% and 50%. The mass ratio is optimally between 25% and between. The contact temperature between the feed material and the solvent is better. 〇.〇 and 8〇.〇之-目. Contact temperature is better between hungry and hunger. Contact pressure is best between 100 bar and 5 bar. Contact pressure is better between 200 bar and _ba The ratio of the cosolvent to the feed material is preferably in the range of 1 (): 1 to 2 〇〇: 1. The ratio of the cosolvent to the feed material φ is preferably in the range of 15:1 to 50:1. The separation pressure is preferably between atmospheric pressure and 90 bar. The separation pressure is preferably between 40 bar and 6 bar. It is preferred to recycle the cosolvent for further use. It is preferred to recycle C02 for further use. The co-solvent is removed by evaporation under vacuum. Preferably, the feed material is contacted with a continuous stream of solvent. Preferably, the feed material is contacted with one or more batches of solvent. Φ can be continuously fed into the lipid stream and solvent stream. Prior to contacting c〇2, the feed stream and the cosolvent stream may be mixed as appropriate. The invention also provides a product produced by the process of the invention which is an insoluble component remaining after contact with a solvent (also referred to herein as "residues" And solubility in the solvent after contact with the feed material Ingredients (also referred to herein as "extracts"). When the feed material is contacted with more than one batch of solvent or the solvent is cooled in multiple steps, there will be multiple, "extract" products. The product contains more sphingomyelin than the feed material. Better product package I20458.doc -15- 200811280 Contains more than 3% of sphingomyelin. The product even more preferably contains more than 1% of the nerve sheath. The product preferably contains more than sputum nerve squama. The product preferably contains more phospholipids than the feed material. More preferably, the product comprises greater than 5% phospholipid lysine. The product even more preferably contains more than the phospholipid lysine. The product preferably comprises greater than 70% phospholipid quinic acid. The product preferably contains more gangliosides than the feed material. The product is better packaged with 神经 more than 2 / 〇 gangliosides. The product even more preferably contains more than 々% of the nerve Lang Langzhi product preferably contains more than 6% of the ganglion: y: lipid. The product preferably contains more cardiolipin than the feed material. Preferably, the product comprises greater than 5% cardiolipin. The product even more preferably contains greater than 1% by weight of cardiolipin. The product preferably contains more than 25% cardiolipin. Preferably, the product contains more mercaptoalkyl phospholipids and/or acetal % ruthenium than the feed material. More preferably, the product comprises greater than 5% mercaptoalkyl phospholipids and/or acetal phosphonium ruthenium products even more preferably comprising greater than 10% mercaptoalkyl phospholipids and/or acetals. Preferably, the product comprises greater than 25% mercaptoalkyl phospholipids and/or acetal phospholipids. Preferably, the product contains more aminoethylphosphonate and/or other phospholipid than the feed material. More preferably, the product comprises greater than 5% of an aminoethylphosphonate and/or other phosphine. The product even more preferably contains greater than 1% by weight of aminoethylphosphonate and/or other phospholipids. Preferably, the product comprises greater than 25% of an aminoethylphosphonate and/or other phospholipid. Abbreviations and acronyms In this manual, the following are the meanings of abbreviations or acronyms used: "CLn means cardiolipin; 120458.doc -16- 200811280 "pc" means phospholipid choline; ''PS' means phospholipid yrosine; 'ΡΕ' means phospholipid 醯 ethanolamine; ''ΡΑ' means phosphatidic acid; "PL' means acetal; ΠΡΡ" meaning Phosphate; "ALP" means alkyl sulfhydryl phospholipid; ''SM' means sphingomyelin; "CAEP, meaning neural amide amine ethylphosphonate; ''GS' means ganglion "N/D" means not detected; "C〇2" means carbon dioxide. [Embodiment] As described in the prior art, it is known that supercritical CO 2 containing up to 12.5% ethanol as a cosolvent can extract phospholipid PC from soybean or egg and extract PE and PI to a much smaller extent. Surprisingly, it has been found that phospholipids PS, CAEP and CL and gangliosides are practically insoluble in (:02 and CrCs-alcohol cosolvents, and SM, ALP, PL and PP are soluble. Therefore, it is possible Soluble phospholipids are separated from insoluble phospholipids and gangliosides to obtain one or the other of the desired components. There are many factors that affect the operation of the process: _Feed materials and raw materials Preparation extraction temperature and pressure 120458 .doc -17- 200811280 Cosolvent Concentration_Total Solvent Production Solvent Flow Rate and Contact Conditions It is advantageous to contain at least 5% by mass of lipid and desirably at least 2% of 质/〇 曰 (especially Ps, The feed material of SM, CL, ALp, pL, and/or ganglioside begins. The feed material can be treated with pure C〇2 to remove large before introducing the cosolvent.

P knife or king neutral lipid. This operation reduces the neutral lipid content of the CO# cosolvent extract, resulting in an extract rich in soluble phospholipids and/or nerves. The form of the material into the shell depends on the lipid source and its lipid composition. The 3% milk extract of the milky crop can be substantially body at high temperatures. In contrast to this, the presence of lower sucrose lipids in egg yolk and marine biolipids tends to produce more fluid feedstocks. Promote good contact' This situation may be beneficial for the preparation of feed materials. It may be cold enough to grind solid materials containing lipids. Lipid feeding into the material can also be made more fluid by including one or both of the water. - meeting;;::? , pressure, force, concentration of the agent and total solvent dosage - treatment: the amount of the material to be recovered, the purity of the final product and the recovery of the method i and (1) rate). For example, virtually insoluble lipids f (such as ps, gs, cae have very low solubility, such that excessive use of the solvent or extremes can result in the loss of small amounts of pS, GS, and CL from the residual portion. The product, but the yield is reduced. On the contrary, if the quality of the moon is good, then the soluble lipid rich # will be more the other wood will be greater, but the overall yield will be lower. 120458.doc 200811280 The economic and product relative The value will determine where this equilibrium is. Another option for obtaining multiple enrichment fractions is to extract under increasingly favorable extraction conditions, such as elevated temperatures. We have found cosolvent concentrations below about 10%. Produces very little fat and/or ganglioside extract. The material extraction rate increases rapidly at higher concentrations. We have found that at least 20% and better 30% of the cosolvent concentration reaches PC, PE, SM, ALP, PL , high extraction degree, and lipid ps, 邙

And GS remains virtually insoluble. “Every substance has its own "critical" point at which the liquid and gaseous state of the substance becomes uniform. Above, but close to the critical point of matter, the substance is a fluid state that combines the properties of both liquid and gas. It has a density similar to that of a liquid and a viscosity and a degree of diffusion similar to a gas. As used herein, the term "super: boundary" means a pressure-temperature interval above the critical point of the material. As used herein, the term "subcritical" refers to a pressure-temperature interval that is equal to or higher than the liquid vapor pressure but below the critical (five). As used herein, the term "near critical" encompasses the supercritical = and ''subcritical' intervals and refers to the pressure and temperature near the critical point. Percentages are by weight/weight solids unless otherwise stated. The term Η, as used in this specification, means, at least in part, consists of ". When interpreting the statements in the specification including the term "including,", 〇 there are features other than those beginning with the term, such as the term "include" will be interpreted in the same manner. The present invention consists of the above and is also conceived to construct only the following examples. Example 020458.doc -19- 200811280 The experimental method is described below with reference to FIG. The lipid-containing feed material of the measured mass to be fractionated is placed in a basket BK1 having a porous sintered steel sheet at the bottom. Place the basket BK1 in 3 〇〇 mL extraction • Guzhai EX1. The apparatus was suspended in a heated water bath WB 1 and maintained at a constant temperature via the use of a thermostat and an electric heater. In the continuous extraction mode of operation, the pump C is used to pump the liquid C〇2 from the supply bottle into the extraction vessel EX1 until the pressure reaches the desired operating pressure _ force, and then the valve is operated to be maintained in the extraction vessel. Constant pressure. After passing valve VI, a pressure drop of 40 to 60 bar is supplied to the cylinder pressure, causing C 〇 2 to be converted to a lower density fluid and losing its solvent strength. The precipitated material is captured in the separation vessel SEIM, c〇2 is escaping from the top of the separator, and is calculated by the Coriolis flow meter (F〇ri〇Hs mass meter) FMi and at -5 C The lower operating condensing trap CT1 recirculates c〇2 back to the feed pump. The extracted material is periodically collected from the separator SEP1 by opening the valve V2. Excipients were only extracted using c〇2 as appropriate until all compounds (such as neutral lipids) that were only soluble in c〇2 were extracted. When the c〇2 extraction no longer produced an extract, the ethanol co-solvent with or without the addition of water was added to the C2 from the supply bottle B2 at the desired flow ratio using pump P2. Ethanol and other extraction materials are separated from c〇2 in separator SEpi and periodically removed via valve V2. After the desired amount of ethanol has been added, the ethanol stream is stopped and the eh stream is continued separately until all of the ethanol has been recovered from the system. The remaining c〇2 was drained and the residue material of the basket was removed and dried under vacuum. The extract was partially evaporated to dryness by rotary evaporation. In the batch extraction mode of operation, CO? is optionally continuously passed through the same equipment as the continuous flow mode until all of the separately extractable material is removed. The c〇2 flow is then stopped and the valve π is closed to maintain pressure, and approximately 140 g of ethanol is pumped from the supply bottle 62 by the pump P2 into the extraction vessel. The system was maintained for 15 minutes to equilibrate the system, after which C02 was started and valve V1 was opened to maintain a constant pressure and the ethanol and dissolved compound <RTIgt; This process was repeated twice more, then discharged [ο] and the residual material in the basket BK1 was removed and dried under vacuum. The phospholipid content and profile of the extract and residue fractions were analyzed by 31P_NMR. The phospholipid mass ratio reported herein is for phospholipid choline (pc), phospholipid creatinine (PI), phospholipid oxime ethanolamine (PE), plasmalogen (pL), phospholipid, alkyl sulfhydryl phospholipid (ALP), In the case of sphingomyelin (SM), ceramide aminoethyl phosphonate (CAEP), phospholipid lysine (PS) and cardiolipin (CL). The process illustrated in Figure 1 is selected for the batch process, while the process illustrated in Figures 2-4 is selected for the continuous flow process. Example 1 - Branch of Dairy Lipid Extract A, Ethanol Mass Ratio 2 $ % Lipid Extract A was obtained by the method disclosed in PCT International Application No. PCT/NZ200 5/000262 (published as WO 2006/0413 16) Total lipid extract. The 4 〇 g dairy lipid extract A (the composition of which is shown in Table 1 (raw material)) was extracted using a continuous extraction mode of operation at 60 ° C and 300 bar. ,, other compounds" consist mainly of neutral lipids. Only 44% of the feed material (extract 1) was extracted using C〇2. This extract is free of phospholipids and is completely neutral. Use 25% of c〇2 The other 31% of the feed material (extract 2) was extracted with a 95% aqueous solution of ethanol. The total amount of ethanol and water added was 880 g. The composition and residue of the fraction extracted with c〇2 and ethanol (extract 2) The composition of the part is shown in Table i 120458.doc -21 - 200811280. The extract is rich in sulphuric acid (PC) and sphingomyelin (SM) which are more soluble in CO 2 and ethanol, and the residue is substantially Rich in phospholipid lysine (PS). The content of phospholipid lysine in the extract phase is virtually undetectable, indicating very low solubility in C〇2 and ethanol and almost complete recovery of the residue phase. Phospholipid lysine. Table 1 Yield of raw material % Composition, % PC PI PS PE SM Other phospholipids Other compound starting material 112 2.8 4.3 13.2 7.8 22 583 Extract 2 31 28.2 0.0 0.2 14.4 15.4 4.9 37.0 Residue 25 6.5 10.5 15.6 30.8 10.2 3.6 22.8

Example 2 · Fractionation of Dairy Lipid Extract A, ethanol mass ratio 31% As in Example 1, at 60. (Running mode with continuous extraction at 3 and 300 bar, first use C〇2 alone to extract 50% of the feed material (extract 1, which is only neutral lipid) and then use 95% of the 31% concentration in CO 2 An aqueous ethanol solution was used to extract 41 g of the dairy lipid extract a (having the same composition as in Example 1), and 33% of the feed material (extract 2) was extracted. The total amount of ethanol and water added was 11,500 g. The composition of the parts is shown in Table 2. The higher ethanol concentration resulted in a more complete extraction of the lipid and the concentration of the fat-filled lysine in the residue portion was 19.3% higher than that found in Example 1. Table 2 Yield % Composition, % PC PI PS PE SM Other phospholipids Other compound materials 11.2 2.8 4.3 13.2 7.8" 2.2 58.3 Extract 2 33 - - - - - Residues 17 4.4 12.6 19.3 27.1 8.5 2.5 25.5 120458.doc -22- 200811280 Example 3: Fractionation of dairy lipid extract a, ethanol mass ratio 43% As in Example 1, using continuous extraction mode of operation at 60 ° C and 300 bar 'First use C〇2 alone to extract 41% of the feed material (Extract 1, which is only neutral fat And then, using a 43% concentration of 95%/% ethanol solution in C〇2 to extract 32% of the raw material (extract 2), 4 〇g of the dairy lipid extract A (having the same composition as in Example 1) was extracted. The total amount of ethanol and water added was 960 g. The composition of extract 2 and the residual fraction is shown in Table 3. The concentration of phospholipid lysine in the residue fraction was 2 (K7% higher than in Examples 1 and 2). The concentration found. Although the extract also contained a high content of neutral lipids, the concentration of SM in the extract was enriched by 125% by mass relative to 7.8 mass% of the raw materials. Table 3 % yield of raw materials Composition, % PC PI PS PE SM Other phospholipids Other compounds 3 Materials 11.2 2.8 4.3 13.2 7.8 2.2 58.3 Extract 2 32 2U 0.0 0.5 13.3 1Z5 3.5 49.1 Residue 27 4.2 13.6 20.7 26.7 7.8 1.9 25.0 Example 4: Dairy Lipid Extract Α Fractionation, 40 X: using a continuous extraction mode of operation at 300 bar, first used separately to extract 54% of the feed material (extract enthalpy, which is only neutral lipid) and then use 30% concentration in C〇2 95% aqueous ethanol solution to extract 12% of raw materials ( Extract 2) 'by this, 39 g of dairy lipid extract A (having the same composition as in Example 1) was extracted. The temperature in this example was 4 (rc. The total amount of ethanol and water added was 975 g. The composition of the extracted portion and the residual portion are shown in Table 4. 120458.doc -23- 200811280 = The degree of extraction is less than 6 (the example below TC is 丨3, but the concentration in the extract is higher. The concentration of PS in the residue is 1; 2.4% is lower than in Examples 1 to 3. 4 Yield of raw materials % Composition 7 --- PC PI PS PE SM Raw material 11.2 2.8 4.3 13.2 7.8 Other compound extract 2 12 2.2 58.3 27.9 0·0 0.3 16.7 15.3 Residue 34 9.9 8.1 12.4 25.3 12.2 ^6~ 34.9 28.5

Example 5 - Partial copper of dairy dish fat concentrate was extracted using a continuous extraction mode of operation at 300 bar and 6 generations... Dairy scale concentrate (composition is shown in Table 5) (raw material), wherein no previous use only The mass ratio of ethanol (95% aqueous ethanol solution) in the extraction step '(7) 2 of C〇2 was 3〇%. The total amount of ethanol and water added was 1 () 26 g. The composition of the extracted portion and the residual portion are shown in Table 5. Since only the raw material lipid of (10) was extracted, the enrichment of the residue was not significant because of the residue, but the concentration was increased from 8: to 8.8%. The poor extraction in this example is due to the physical properties of the solid feed material that limits mass transfer. In contrast, the lipid extract of the sample (1) was liquid at the treatment temperature and had a preferred extraction ratio. =^ The amount of extractable material is increased by the same method of preparation of the raw materials and/or a longer equilibrium time and/or a larger amount of solvent. table 5

120458.doc -24- 200811280 Example 6: Branch of Dairy Phospholipid Concentrate Using Batch Extraction Method 19 g of dairy phospholipid concentrate was extracted at 300 bar and 60 ° C using a batch extraction mode of operation (composition of Example 5) Said). A total of 22% of the feed material was extracted by sequential extraction of three of each consisting of 140 g of ethanol (95% aqueous ethanol) in 300 mL of C02. The composition of the extracted fraction and the final residual fraction are shown in Table 6. In this example, 22% of the raw material lipid was extracted, which was significantly higher than the raw material lipid obtained in the continuous extraction example (Example 5) and a lower total amount of the ethanol co-solvent was used. The concentration of phospholipids in the residue has increased from 8% to 11.2%; and the concentration of neurolemin in the extract has increased from 15.1% to 16.7%. This example demonstrates an increase in total extracted material caused by contact for a longer period of time to more completely dissolve the soluble portion. Table 6 Yield of raw materials % Composition, % PC PI PS PE SM Other phospholipids Other compound materials 15.4 5.3 8.0 21.6 15.1 0.3 34.3 Extract 22 32.4 0.5 0.4 17.7 16.7 4.7 27.5 Residue 78 13.6 7.4 11.2 26.6 13.3 2.9 25.0 Example 7 • Fractionation of dairy lipid extract B, ethanol mass ratio of 10% This example relates to the extraction of dairy lipid extract B (the composition of which is shown in Table 7) (raw material), which is from PCT International Application PCT/NZ2004 Total lipid extract obtained by the high fat whey protein concentrate method disclosed in WO0000/06614 (published as WO 2004/066744). The "other compounds" listed include 2-3% gangliosides and about 3% lactose, which are not present in dairy lipid extract A. In this example, 42 g of dairy lipid extract B was extracted using a continuous extraction mode of operation at 300 120458.doc -25 - 200811280 bar and 60 C. 52% of the feedstock was extracted using C〇2 alone (extract. Only 3% of the raw material lipid (extract 2) was extracted using 460 g of 95% aqueous ethanol solution' and the extract contained less than 1% phospholipid. Phospholipid extraction does not occur to any significant extent for ethanol mass ratios of 1% or less. However, ethanol does extract some additional neutral lipids that are not extracted with C〇2 alone. In this case, residues Rich in PS and SM. Yield of raw materials % Composition, % PC PI PS PE SM Other phospholipids Other compound raw materials 7.4 2.5 3.9 10.3 5.7 1.3 69.0 Extract 2 3 4.5 0.0 0.0 1.6 1.0 0.3 92.6 Residue 45 15.0 6.1 8.7 21.8 12.0 5.9 30.7 Example Dairy Lipid Extract B, ethanol mass ratio ^ QO / 〇 In this example, 40 g of dairy lipid extract B was extracted using a continuous extraction mode of operation at 300 bar and 60 ° C. Used alone C〇2 extracts 51% of the feed material (extract 1). Another 7% of the feed material (extract 2) is extracted using 760 g of a 30% aqueous solution of 95% ethanol in C〇2. Residual part of the fat filling profile display In Table 8. The residue is rich in ps and SM. Yield % of raw material Composition, % - PC PI PS PE SM Other phospholipids Other compound raw materials 7.4 2.5 3.9 10.3 5.7 1.3 69^~ Extract (2) 7 22.5 0.5 0.4 14.0 11.2 3.3 48.2 Residue 41 12.0 5.5 8.5 20.2 Γ io.o 2.4 1 41.5 120458.doc -26- 200811280 Example 9: Fractionation of dairy lipid extract A, ethanol mass ratio 3% This example shows low cosolvent concentration In the case of 10 mass%, the stone resin was not extracted. In this example, the operation mode of continuous extraction at 300 bar and 6 (TC) was 98% ethanol with a mass ratio of C〇2 of 3%. 27 g of the dairy lipid extract A as described in Example 1 was extracted, without the extraction step using only c. 2. 62% of the feed material was extracted. The detectable phospholipid was not extracted. This extract represents 90. Neutral lipids are present in the feed material. The extraction rate of neutral lipids from the feed material is substantially faster when using ethanol co-/valley than with C〇2 alone. Use less than the total of 4850 used. 150 g of ethanol in g C02 substantially extracts the extracted material, and as in the case, Neutral lipids generally requires a separate 10 kg C02. Example 10 ·· yolk lecithin branch penetration present embodiment based on the fractionation of a commercially available egg yolk lecithin, phospholipids profiles shown in Table 9. Phospholipid lysine was not detected in the raw material lipid, indicating that the concentration was less than < 0.5%. In this example, 34 g of feed material was extracted using a continuous extraction mode of operation and a 25% strength 95% aqueous solution of ethanol at 3 bar and 6 liters. 4% of the feed material was extracted as a neutral lipid using c〇2 alone. An additional 49% of the feed material was extracted using ethanol and c〇2 with a total ethanol flow of 640 g. The phospholipid profiles of the extract and the residual fraction are shown in Table 9. In this example, the content of the fat-filled lanthanum acid in the residual material is substantially enriched compared to the undetectable content of the feed material. 120458.doc -27 - 200811280 Table 9 Yield of raw materials % Composition, % PC PI PS PE SM Other phospholipids Other compound materials 56.4 N/DN/D 6.4 2.0 5.7 29.4 Extract 49 43.5 N/DN/D 9.2 2.6 2.1 42.5 Residue 6 17.4 8.0 5.9 19.1 3.8 3.8 42.0 Example 11 · Fractionation of egg yolk phospholipid extract This example relates to the fractionation of the egg yolk phospholipid fraction, which is shown in Table 9. In this example, 40 g of feed material was extracted using a continuous extraction mode of operation and a 28% strength aqueous 95% ethanol solution at 300 bar and 60 °C. CO 2 was used alone to extract 50% of the feed material in the form of a neutral lipid. An additional 46% of the feed material was extracted using ethanol and 〇:02 with a total ethanol flow of 800 g. The extracts and residual phospholipids are shown in Table 1. In this example, the amount of phospholipidic acid in the residual material is substantially enriched compared to the amount in the feed material, while the sphingomyelin is enriched in the extract relative to the feedstock. Table 10 Yield % of raw materials Composition, % PC PI PS PE SM Other phospholipids Other compound raw materials 21.2 0.6 0.4 5.2 1.6 0.9 70.1 Extract 46 65.6 0.3 N/D 6.3 2.8 2.3 22.8 Residue 4 12.9 11.2 8.2 27.6 2.8 8.2 29.2 Examples 12. Fractionation of Hoki Head Lipid Extract This example relates to the fractionation of the taro-free lipid extract, and the phospholipid profiles are shown in Table 11. In this example, 25 g of feedstock 120458.doc -28-200811280 was extracted at 300 bar and 60 °C using a continuous extraction mode of operation and a 31% strength 95% aqueous ethanol solution. The c〇2 was used alone to extract 1% of the feed material in the form of a neutral lipid. An additional 72% of the feed material was extracted using ethanol and C〇2 with a total ethanol flow of 940 g. The phospholipid profiles of the extract and the residual fraction are shown in Table η. In the present case, the content of the linonic acid in the residual material is substantially enriched compared to the content in the feed material. Some Ps were also observed in the extract phase. The alkyl mercapto phospholipid choline (AAPC) (a class of alkyl sulfhydryl phospholipids) is fully extracted. Table 11 Yield of raw materials % Composition, % PC PI PS PE SM AAPC Other phospholipids Other compound materials 1 9.2 U L4 4.8 0.5 1.1 1.8 80.8 Extract 72 14.2 0.0 0.7 53 0.5 1.6 0.6 71.2 Residue 27 143 7.1 7.6 13.9 0.0 0.0 6.2 47.7 Example 13: Fractionation of Bovine Heart Lipid Extract This example is about the separation of bovine heart lipid extracts. The fat filling profile is shown in Table 9. In this example, 40 g of the feed material was extracted using a continuous extraction mode of operation at 3 ° bar and 60 ° C and a 33% strength aqueous solution of 95% ethanol in C 〇 2 . Lipids were not extracted using c〇2 alone. 79% of the feed material was extracted using ethanol and c〇2, and the total ethanol flow rate was 96 〇 g. The extracts and residue fractions of the grease are shown in Table 12. The amount of phospholipidic acid in the residual material is substantially enriched compared to the amount in the feed material. Cardiolipin is also significantly enriched in the residue. 120458.doc -29- 200811280 Table 12 Yield of raw materials, % by weight Composition, % by weight CL PC PI PS PE SM Other phospholipids Other compound materials 16.8 13.4 3.2 1.5 123 3.6 15.3 33.9 Extract 79 8.2 18.6 0.8 0.4 S.6 3.5 13.1 46.7 Residue 21 42.2 2.8 14.1 4.7 23.4 12.8 0.0 Example 14: Fractionation of dairy lipid extract a using a propan-2-ol cosolvent In this example, a continuous extraction mode of operation at 300 bar and 6 (TC) And a 95% aqueous solution of propan-2-ol having a cerium concentration of 35% in C〇2, and extracting 39 g of the dairy lipid extract A as described in Example 1. The 甩c〇2 was separately extracted as a neutral lipid by 48%. The material was fed in. Further, 23% of the feed material was extracted using a propan-2-ol cosolvent and c〇2 (total propanol mass 810 g). The extract and residual phospholipids are shown in Table 3. The content of phospholipid lysine in the residual material was substantially enriched, and the results were comparable to those of Examples 1 and 2. The use of a comparable concentration of ethanol gave a slightly lower total ps content than Example 2. Observed in the extracted fraction The PS content is also high, indicating the choice of propanol It is not as good as ethanol. On this basis, ethanol alone will be the preferred cosolvent. Table 13 Yield of raw materials % Composition, % 丨 -1 PC PI PS PE SM Other phospholipids Other compound materials • it ti— , ι / 11.2 2.8 4.3 13.2 7.8 2.2 58.3 Extract tlTt »l/_ 23 irfj' 0.8 1.3 19.5 14.0 4.2 32.4 Residue 29 10.7 8.6 13.0 23.8 15.5 3A 25.0 Example 15 ··········································· Fractionation of fat (Heaitheries 彡p fat-filled natural dietary supplement 12Q458.doc -30· 200811280 filling, Healtheries〇fNeW Zealand Limited), the composition of which is shown in Table 9. In this example, at 3〇〇巴和6〇 Extract the 42 g feed material using the continuous extraction mode of operation and the 33% ethanol solution of 33% ethanol in C〇2. The lipid was not extracted by using c〇2 alone. Use ethanol and c〇2# to take 91%. The material was fed and the total ethanol flow was 52 〇g. The extract and residual phospholipid profiles are shown in Table 14. pc&pE was preferentially extracted and significantly enriched in the extract. In this example, no detectable content ^ or SM. Table 14 Yield % of raw materials Composition, % PC PI PS PE SM Other fat-filled other raw materials 22.2 12.3 0.0 17.4 0.0 11.7 36.4 Extract 9 /Λ 1 31.9 0.7 0.0 9.9 0.0 6.1 51.4 Residue 91 20.7 132 0.0 18.4 0.0 12.4 35.2 Example 16·················································································· The phospholipid fraction contains 55% pc, 29% PE and 14% PI. The raw material lipid was pumped to 1 Torr [top of the pressure vessel, and contacted with c〇2 containing 8.7% of 98% aqueous ethanol solution flowing upward through the vessel at a pressure of 300 bar and a temperature of 60 °C. The extract phase is taken from the top of the continuous contact vessel and the raffinate phase is periodically withdrawn from the bottom of the vessel. The lipid material rate was 1.5 kg/hr. The flow rate of the C02+ cosolvent is 27 kg/hr. The extract phase is primarily a neutral lipid but also contains 2% by weight of the phospholipid present in the feed stream. The phospholipids in the extract fraction consisted of pc between 7〇% and 1〇〇%, the remainder being mainly PE. This situation indicates that pc is preferentially extracted than other phospholipids. 120458.doc •31 - 200811280 In the second experiment, the raw material lipid was premixed with 98% ethanol (with 2% water) at a lipid concentration of 10.2%. The mixture was pumped to the top of the pressure vessel and brought into contact with the upward flowing c〇2. The total > agronomic degree of ethanol in C〇2 under steady state treatment conditions was 5.9%. In this case, the quality of the dish fat in the raw material is extracted. The composition in the extract phase is composed of 6〇% and 7〇Q/. The composition of the pc between the rest is mainly PE. The presence of PI and other phospholipids in the extract was not detected by the HPLC method used. Example 17 · Green lip mussel (green jjpped m is a branch of lipid extract. This example is about the fractionation of the lip extract of the green-lipped mussel. The phospholipid profile is not shown in Table 11. In this example, at 25 bar and 60t: Under the batch agitation tank method, 122 g of feed material was extracted using C〇2 and 30.5% ethanol (containing 5% water). The lipid was placed in a stirred tank, and c〇2 was added to obtain the desired pressure. Next, 95% ethanol was added during constant stirring. Then, after stirring for an hour, 65% of the feed material was extracted using c〇2 and ethanol by sampling the extract phase under constant pressure. Extract and residual phospholipids The profile is shown in Table 15. In this example, the CAEp content in the residual material is substantially enriched compared to the content in the feed material. Alkyl phosphatidylcholine choline (AAPC) (-alkyl hydrazine) Partially extracted phospholipids. Table 15

120458.doc -32- 200811280 Example 18 · Antarctic shrimp (kHU) lipid separation This example shows the fractionation of Antarctic shrimp lipid from Antarctic shrimp powder and indicates the concentration of AAPC in the extract and the concentration of AAPE in the residue. Supercritical c〇2 was used to continuously extract 5619·9 g of freeze-dried Antarctic shrimp powder containing 21.4% lipid and corresponding phospholipid concentrations as shown in Table 16 at 3 bar and 313 K until no longer obtained Extracts. This extract (extract enthalpy) contains no phospholipids and is substantially all neutral lipids. A total of 650 g of this extract was obtained, and 66.41 kg of CO was used, followed by a mass ratio of 11% ethanol to c〇2, and pure ethanol to extract the residual powder. The CO: and ethanol extract phases were passed through two consecutive The separation pressures were 95 bar and 6 bar, respectively. The majority of the phospholipid-rich extract (extract 2) was obtained in the first separator and most of the total was obtained in the second separator. Solvent (extract 3). The composition of extract 2 and residual powder is not shown in Table 16. Alkyl phosphatidylcholine choline (aapc) (a type of alkyl im squaraine) is concentrated in a rich dish The lipid extract is highly enriched and cannot be extracted to a large extent to the pyridyl phospholipid oxime ethanolamine (AApE) (another type of alkyl sulfonate). Table 16 Yield % of the raw material, % PC PI PS PE CL AAPC AAPE Other compounds _78.6 53 7 Raw material 6.6 0.0 0.0 0.4 0.1 0.6 0.1 Extract 2 43 39.8 0.0 0.0 0.3 0.2 4.6 0.2 Residue 79.2 3.6 0.0 0.0 ”3 0.2 0.5 0.1 93.4 Example 18 · Dairy Separation of lipids from beta whey powder This example is shown from beta whey powder ( Powder and concentrated milk fat globule membrane) fractionating 120458.doc -33- 200811280 dairy lipid and indicate the concentration of residual powder in ps & SM concentration using supercritical C〇2 + ethanol extract of the obtained. 5835.3 g of β-whey powder containing phospholipids of the concentrations shown in Table 17 were continuously extracted at 300 bar and 313 using supercritical C〇2 until the extract was no longer obtained. This extract contains no phospholipids and is essentially all neutral lipids. Using 94.42 kg C〇2, 1085·6 g of this extract (extract 1) was obtained. Next, using a mass ratio of 25% ethanol to C〇2 under 3 bar and M3 κ, 2906.3 g of residual powder was re-extracted with c〇2 and absolute ethanol. The mixture was extracted with this mixture for 9 minutes (7.a kg of drunkenness). The (11〇2 and D drunken phases were passed through two continuous separators with pressures of 100 bar (extract 2) and 54 bar (extract 3), respectively. The extract was separated in two. Separate between the devices. A total of 262. 2 g of extract was obtained. The combined extracts (Extract 2 and Extract 3) and the composition of the residual powder are shown in Table 17. The extract was rich in sphingolipids and The residue is rich in phospholipid yrosine. Table 17 Yield of raw material % Composition, % PC PI PS PE SM Other phospholipids Other compound materials 4.9 1.5 2.3 5.6 4.3 0.1 81.3 Extract 2+3 9.02 49.6 0.0 0.0 12.4 30.1 0.7 7.1 Residue 71.14 0.3 2.0 3.0 3.0 0.5 0.1 91.1 ~ Industrial Applicability The present invention can be used to provide a product having a high content of a specific phospholipid and/or glycolipid (including cardiolipin and phospholipid lysine and sphingomyelin). The compositions and methods described are useful in a variety of applications, including infant formula 120458.doc -34-200811280 powder, brain health, sports nutrition, and dermatological compositions. References 1. Palacios, LE·, Wang, T., Extraction of egg-y Olk lecithin, JAOCS 82,8,2005 2. Kang9 D.H.j Row5 KeH.9 Fractionation of soybean phospholipids by preparative high-performance liquid chromotography with sorbents of various particle size,

Journal of Chromatography A, 949, 2002 3. Kearns, JJ, Tremblay, PA, Robey, RJ, Sunder, S., Process for purification of phospholipids, U.S. Patent No. 4,814,111, 1989 4. Teberikler, L., Koseoglu, S., Akkerman, A·, Selective extraction of phosphatidylcholine from lecithin by supercritical carbon dioxide/ethanol mixture, JAOCS 78, 2, 2001 5. Montanari, L., Fantozzi, P·, Snyder, JM·, King, JW · Selective extraction of phospholipids from soybeans with supercritical carbon dioxide and ethanol, J Supercritical Fluids, 14, 1999 6. Taylor, SL·, King, JW, Montanari, L., Fantozzi, P·, Blanco, MA 5 Enrichment and fractionation Of phospholipid concentrates by supercritical fluid extraction and chromatography,Ital J Food Sci,1,12,2000 7. Tanaka, Y., Sakaki, I., Extraction of phospholipids from I20458.doc -35- 200811280 unused natural resources with supercritical carbon dioxide And an entrainer,Journal of oleo science 54,11,2005 8. Bulley, NR·, Labay, L., Arntfield, SD, Extraction/ Fractionation of egg yolk using supercritical C02 and alcohol entrainers, J supercritical fluids, 5, 1992 ° [Simplified illustration] Figure 1 To illustrate the preferred method of the present invention.

Figure 2 is a timing diagram illustrating a second preferred method of the present invention. Figure 3 is a plan view showing a third preferred method of the present invention. Figure 4 is a plan view showing a fourth preferred method of the present invention. [Main component symbol description] B1 Supply bottle B2 Supply bottle BK1 Basket CT Condensate trap EX1 Extraction container FM1 Coriolis mass flowmeter P1 Pump P2 pump SEP1 separator VI Valve V2 valve WB1 Heating water bath 120458.doc -36-

Claims (1)

200811280 X. Patent application scope: 1. A method for separating a feed material into a soluble component and an insoluble component, comprising: (a) providing a feed material comprising one or more of the following: (i) At least 1% by mass of phospholipid lysine; (ii) at least 1% by mass of a neurolipid phospholipid; (iii) at least 0.3% by mass of a mercaptophosphoryl phospholipid and/or a condensed phospholipid; (iv) at least 〇 .5 mass% of aminoethylphosphonic acid vinegar and/or other phospholipids, · (7) at least 1% by mass of cardiolipin; (vi) at least 〇3% by mass of ganglioside; (b) providing inclusion a solvent for: (0 supercritical or near-critical CO 2 ; and (ii) a cosolvent comprising one or more Cl_C 3 monohydric alcohols and water, wherein the cosolvent accounts for at least 丨〇 % by mass of C 〇 2 , and The cosolvent has a water content of from 〇 to 4 〇 mass ❻ / g; (C) contacting the feed material with the solvent and subsequently separating the solvent containing the soluble components from the insoluble components; (4) separating as appropriate The soluble components and the solvent. 2. If the request item 1 夕古,, also ' ' /, the The feed material contains a fat-filled lanthanum amide larger than i 0 / 0. 3 · If the claim 1 is a serine acid, the feed material contains more than 2% phospholipid 醯 4 · as in claim 1 Turning the face is missing. The feed material contains more than 5% phospholipid 醯 120458.doc 5 · as requested in the method, and ^ phospholipids, /, the feed material contains more than 1% of the neural crest 6 · as requested Item 1, the method of 1, and no phospholipids in the middle, and the μ feeding material contains a nerve sheath greater than 53⁄4. 7. The method of claim 1 only, wherein the sputum is ... sheath chlorosis green. ^ The material contains more than 15% Nerve 8 · as for the item 1 lipid. #法' where the feed material contains more than 1% of the heart phosphorus. 9. The method of claim, wherein the feed is fat. The shellfish contains more than 2% of the heart phosphorus 10. The method of claim 1 is only 1 wherein the preparation is x &quot; lipid. The μ-into material contains more than 5% of the heart 粦 11 · as requested in the method 1 , wherein the ganglioside. The eight-material 枓 contains more than ο·3% of the nerve. 12. The method of claim ,, wherein the 誃 脂 λ /, μ 贝 入 inclusion material contains large 1% of the ganglion ganglion 13. The method of claim 1, wherein the feed material comprises greater than 2% of the gods 14. The method of claim 1 wherein the feed material comprises greater than (four) sulfhydryl phospholipids And/or a plasmalogen. 15. The method of claim [wherein the feed material comprises greater than dethiol phospholipids and/or plasmalogens. 16] The method of claim [wherein the feed material comprises greater than 〇 〇 醯 醯 醯 based phospholipids and / or plasmalogens. 12045S.doc 200811280 17. The method of claim 1, the ethyl phosphonate and/or its octagonal feed material comprises greater than 0.5% aminophosphoryl lipid. The feed material comprises greater than 5% of an amine group. The method of claim 1, wherein the phosphinate and/or other phospholipid 19 is as in the case of claim 1, and the feed is in the A/ The material contains greater than 20% aminoethyl ketamine and/or other phospholipids. 20. Species: A method for separating a material into a soluble component and an insoluble component, comprising: (a) providing a feed material comprising one or more of the following: - (I) at least 1 (%) at least 1% by mass of sphingomyelin; ···) to &gt;, 〇.3 11% thiol-based phospholipid and/or condensate; ·) to &gt;, 〇·5 畺% of aminoethylphosphonate and/or other phospholipids; (ν) at least 1% by mass of cardiolipin; or (vi) at least 〇·3 mass% of nerves (b) providing a first solvent comprising supercritical or near-critical c〇2; (c) contacting the feed material with the first solvent and subsequently contacting the first solvent comprising the first soluble component Separating an insoluble component; (d) separating the first soluble component and the first solvent as appropriate; (e) providing a second solvent comprising: (i) supercritical or near-critical C〇2; Ii) a cosolvent comprising one or more Cl_c3_ols and water, wherein the cosolvent comprises at least 10% by mass of (02) and the water content of the cosolvent is from 4 to 4 458质量%; 120458.doc 200811280 (f) contacting the ^-insoluble component with the first solvent and then separating the second solvent each having the first commissable component from the second insoluble component, (g) The second soluble component and the second solvent are optionally isolated. The method of claim 20 wherein the first solvent comprises a mixture of supercritical or near critical eh and less than 10% Cl_C3 monohydric alcohol. The method of claim 2 or 21, wherein the feed material comprises greater than Phospholipid lysine. Wherein the §Hai feed material comprises greater than 2%. 23. The method of claim 20 or 21 is phospholipid lysine. 24. The method of claim 20 or 21, wherein the phospholipid is seric acid. 25. The method of claim 20 or 21, sphingomyelin. 26. The method of claim 20 or 21, sphingomyelin. Wherein the feed material comprises more than 5% of which 5" feed material comprises greater than 1% &quot;, the feed material comprises greater than 5% of 27. The method of claim 20 or 21 wherein the feed material Contains greater than 15% of sphingomyelin. 28. The method of claim 20 or 21, wherein the feed material comprises a cardiolipin greater than ".." The method of claim 20 or 21, wherein the feed material comprises greater than (4) cardiolipin. _A method of claim </ RTI> wherein the feed material comprises greater than said cardiolipin. 120458.doc 200811280 wherein the 5H feed material comprises greater than 0.3% wherein the feed material comprises greater than 1% of the 〃中馈 feed material A ganglioside comprising more than 2% of 31. The method of claim 20 or 21. 32. The method of claim 20 or 21, ganglioside. 33. The method of claim 20 or 21, nerve The method of claim 20 or 21, wherein the feed material comprises a decylalkylphospholipid and/or a plasmalogen greater than 〇5〇/( 35. The method of claim 20 or 21 Wherein the feed material comprises greater than 2% mercaptoalkyl phospholipids and/or plasmalogens. 36. The method of claim 2 or 21, wherein the feed material comprises greater than 10% mercaptoalkyl Phospholipids and/or plasmalogens 37. The method of claim 20 or 21 wherein the feed The material comprises an aminoethylphosphonate and/or other phospholipids greater than m. 38. The method of claim 20 or 21, wherein the feed material comprises greater than an aminoethylphosphonate and/or other phospholipid 39. The method of claim 20 or 21 wherein the feed material comprises greater than the aminoethylphosphonate of the woven group and/or other phospholipids. The method of any one of claims 1 to 21 , 1 /, 肀 4 feedstock is derived from terrestrial animals, marine animals, terrestrial plants, -, ^ marine plants or microorganisms such as micro-bath, yeast and bacteria. • The method of claim 40, wherein the feed The materials are from sheep, mountain, pig, mouse, buffalo, lagoon, thin cow, horse, donkey, American, cow or human. 120458.doc 200811280 42 · The method of seeking 4〇, The feed material is selected from the group consisting of: tissue, tissue part, organ, organ part, milk, milk part, colostrum, colostrum knife, blood and blood part. 43 · Method of requesting item 4, wherein the feeding Materials are derived from dairy materials, large and materials, eggs, animal tissues 44. The method of claim 4, wherein the feeding material is selected from the group consisting of a composition comprising a dairy lipid, a composition comprising an egg lipid, and a composition comprising a marine biological lipid. The method of any one of claims 1 to 21, wherein the feed material is a milk portion. The method of claim 45, wherein the feed material is selected from the group consisting of: white milk, white milk, Beta whey, beta whey fraction, butter whey, whey fraction, whey, whey fraction, colostrum and colostrum. 47. The method of any one of claims 1 to 21, a lipid globule membrane. The method of any one of claims 1 to 21, wherein the feed material comprises milk wherein the feed material comprises at least (a) 1% phospholipid lysine and (b) 0.3% ganglion: y: fat. The method of claim 48, wherein the feed material comprises at least: (a) 1% phospholipid lysine; (b) 1% sphingomyelin; and (c) 0. 3% ganglion Glycosides. The method of claim 48, wherein the feed material comprises at least 120458.doc 200811280 (a) i % continued: fatty acid serine; (b) 1% sphingomyelin; (c) 1% cardiolipin; and (d) 0.3% gangliosides. The feed material of the crucible 4 has been based on the method in which the feed material is a solid 51. The method according to any one of claims 1 to 21 is modified. 52. The method of any one of claims 1 to 21. Wherein the feed material is subjected to low temperature milling as in the method of claim 5 2 prior to contact with the solvent. 54. The alcohol of any one of claims 1 to 21 selected from the group consisting of: methanol: B: wherein the cosolvent comprises: a mixture thereof; and + n-propanol, isopropanol and (b) 0- 40 quality ❶ /. Water. Wherein the ruthenium co-solvent comprises between 〇 and 2 〇% by mass, wherein the δHeil cosolvent comprises water between 〗 〖 and 〇 〇 mass % 55. 56. Water between the methods of claim 54. 57. The method of claim 54, wherein the alcohol is ethanol. The method of claim 1 to 21, wherein the cosolvent is a 95% aqueous solution of ethanol. 59. Such as:, item! The method of any one of 21, wherein the mass ratio of the co-solvent in (3) 2 is between 5% and 60%. The method of Lunar 59, wherein the mass ratio is between 20% and 50%. 120458.doc 200811280 61. The method of claim 59, and the middle of the eight-side shell 1 ratio between 25% and 3〇%. The method of any one of claims 1 to 2, wherein the contact temperature between the feed material and the solvate is between lot: and 8 CTC. 63. The method of claim 62, wherein the contact angle is between 55 ° C and 65 ° C of FbI 〇 64. Between 100 Bars and 5 Bars in Requests 1 to 21. 65. The method of claim 64, between. The method of the present invention, wherein the contact pressure is between: the contact pressure is between 2 〇〇巴 and 3 〇〇巴 66, as in any one of claims 1 to 21, wherein the cosolvent and the feed material The ratio is in the range of 1 〇:1 to 200:1. 67. The method of claim 66 wherein the cosolvent is in the range of from 15:1 to 50:1.卄比比羊 68. As in any of the requirements 1 to 21, π is produced, and the separation pressure of A is between atmospheric pressure and 90 bar. 69. The method of claim 68, wherein the separating force is between Samba (4) and 0, wherein the cosolvent is recycled to recycle the C〇2 therein, wherein the feed is fed by evaporation under vacuum And the method of any one of claims 1 to 21 for further use. 71. The method of any one of claims 1 to 21 is used in one step. 72. The method of any one of claims 1 to 21 to remove the cosolvent. 73. The method of any one of claims 1 to 21 120458.doc 200811280 solvent stream contact. 74. If requested! The method of any one of 2, wherein a plurality of solvents are contacted. The feed material is a method of any one of clauses 1 to 21, wherein the lipid stream and the stream are continuously fed. The method of any one of claims 1 to 21, wherein the method of contacting the C 〇 2 to mix the material of the feed material with the cosolvent stream is carried out by a method of any one of the claims (4) The product produced. : product of long term 77, wherein the product contains a ratio of the sphingomyelin. 79. The product of claim 77, wherein the product contains more than 3% of the vulcanity v 80. The product of the sheath phosphorus term 77, wherein the product comprises greater than 1% neurological scale 8 1 · as claimed in claim 7 lipid. a product, wherein the product comprises a sphingolipid greater than (10) 8 2 as claimed in claim 7 wherein the product contains more than 83% of the feed material, wherein the product comprises greater than 5 % of 84 · as requested by the amine acid. Wherein the product comprises greater than 30% phosphorus 85. The product of the claim, which comprises greater than 70% of the phospholipid, silk fibroin, phospholipid, phospholipid, silk fibroin I2045S.doc 200811280 86 · as requested, product ' Wherein the product contains more ganglioside than the feed material. 87·士口言奋work 'Products of § 7' wherein the product contains more than 2% of ganglion lipids 0, 8 S. 'kp jg, 77 products, wherein the product contains more than 4% of ganglion rouge . , 8 9 · If requested, the product of g, 7?, wherein the product contains more than 6% of gangliosides. , 9 0 · Yan Qinggong hundred, 7 products, wherein the product contains more cardiolipin than the feed material. The product of j, 7 7 wherein the product contains greater than 5% heart fat. The product of claim 77, wherein the product comprises greater than 1% pectin. 93. The product of claim 77, wherein the product comprises greater than 25% cardiolipin. The product of claim 77, wherein the product contains more lanthanyl phospholipids and/or plasmalogens than the feed material. 9 The product of claim 77, wherein the product comprises greater than 5% mercaptoalkyl ruthenium and/or plasmalogen. A product of the term 77, wherein the product comprises greater than 103⁄4 of a mercapto-based fat and/or a plasmalogen. The product of claim 77, wherein the product comprises greater than 25% mercaptoalkyl linoleum and/or plasmalogen. 98. The product of claim 77, wherein the product contains more aminoethylphosphonate and/or other phospholipid than the feed material. 99. The product of claim 77, wherein the product comprises greater than 5% aminoethyl 120458.doc -10- 200811280 phosphonate and/or other phospholipids. 100. The product of claim 77, wherein the product comprises greater than 1% aminoethyl phosphonate and/or other phospholipids. 101. The product of claim 77, wherein the product comprises greater than 25% aminoethyl phosphonate and/or other phospholipids. 120458.doc π -