WO2010038964A2 - Procédé d'extraction et de séparation de matières actives de krill, et produits associés - Google Patents

Procédé d'extraction et de séparation de matières actives de krill, et produits associés Download PDF

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Publication number
WO2010038964A2
WO2010038964A2 PCT/KR2009/005528 KR2009005528W WO2010038964A2 WO 2010038964 A2 WO2010038964 A2 WO 2010038964A2 KR 2009005528 W KR2009005528 W KR 2009005528W WO 2010038964 A2 WO2010038964 A2 WO 2010038964A2
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krill
carbon dioxide
extraction
ethanol
supercritical carbon
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PCT/KR2009/005528
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English (en)
Korean (ko)
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WO2010038964A3 (fr
Inventor
신언무
이상수
서장원
김미영
Original Assignee
주식회사 유맥스
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Priority claimed from KR1020090019347A external-priority patent/KR100951727B1/ko
Application filed by 주식회사 유맥스 filed Critical 주식회사 유맥스
Publication of WO2010038964A2 publication Critical patent/WO2010038964A2/fr
Publication of WO2010038964A3 publication Critical patent/WO2010038964A3/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/50—Molluscs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/20—Fish extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners

Definitions

  • the present invention relates to a method for extracting krill, and more particularly, using a special nutrient contained in krill using an extraction separation method using a pressurized liquid, supercritical carbon dioxide, such as astaxanthin, omega-3 polyunsaturated fatty acid ( ⁇ -3 poly unsaturated fatty acid ( ⁇ -3 PUFA) and phospholipids, and recovering protein from the remaining extract.
  • a pressurized liquid supercritical carbon dioxide, such astaxanthin, omega-3 polyunsaturated fatty acid ( ⁇ -3 poly unsaturated fatty acid ( ⁇ -3 PUFA) and phospholipids
  • Krill is a small shrimp-like zooplankton that is distributed in clean areas of the Antarctic waters and is located at the bottom of the food chain, so there is little risk of accumulation of heavy metals. It is also known to contain more polyunsaturated fatty acid-bound phospholipids relative to other aquatic organisms.
  • Dehydrated krill contains about 20% lipids, of which about 50% are phospholipids, and about 40% of the phospholipids form omega-3 fatty acid-bound forms containing EPA and DHA.
  • the lipids contained in krill have been found to contain a large amount of the antioxidant astaxanthin.
  • Omega-3 fatty acids account for 40% of the fatty acids that make up the brain and 60% of the fatty acids that make up the retina, and are known to be found in blue fish and fish oils such as sardines, mackerel, and saury. These omega-3 fatty acids are known to help improve triglycerides and cholesterol in the blood to help blood flow smoothly and to relieve the symptoms of cardiovascular diseases.Inhibiting platelet aggregation and lowering blood pressure can lead to brain cells It is known to suppress or destroy lipids to alleviate or prevent dementia. Since such unsaturated fatty acids are not produced sufficiently in the body, it is known that they should be consumed steadily through food and the like.
  • krill is known to have a higher ratio of phospholipid-bound omega-3 polyunsaturated fatty acids than other marine and aquatic organisms.
  • the form combined with phospholipids improves absorption, body utilization, and physiological effects compared to neutral lipids.
  • Astaxanthin is a natural carotenoid with a strong antioxidant power, nicknamed supervitamin E. It is known that the antioxidant power, which is the ability to remove excess oxygen generated in the body, is superior to ⁇ -carotene and vitamin E. The ability to remove singlet oxygen, which is particularly toxic among free radicals, is 100 times higher than that of vitamin E, and More than ten times have been found through experiments. In addition, it has been confirmed in recent studies that 800 times higher than CoQ10, which is known to have high antioxidant power. When free radicals bind to fatty acids in tissues, they become fat peroxides, which oxidize tissues to cause lifestyle diseases or damage DNA by damaging DNA. Astaxanthin has a 1,000-fold inhibitory effect on the production of fat peroxide. have.
  • U.S. Patent No. 4,331,695 discloses the use of a pressurized solvent that is gaseous at room temperature, such as propane, butane or hexane. This extraction method is carried out at a desired temperature of 15 to 80 ° C. for finely chopped vegetables or finely ground animal products. Thereafter, the extracted oil is solidified under high temperature and high pressure conditions of 50 to 200 ° C. Hexane, however, is an undesirable solvent for the extraction of marine animals such as krill. Moreover, the high temperatures used in the condensation step are disadvantageous by modifying the lipids.
  • Canadian Patent Application No. 1,098,900 discloses a method for extracting oil from krill. This method involves emulsifying fresh or thawed krill in an aqueous medium. The oil fraction extracted from the krill emulsion is recovered by centrifugation.
  • a simple method for the isolation and purification of total lipids from animal tissues 1995
  • has been presented an extraction method using a mixture of chloroform and methanol as a solvent has been presented an extraction method using a mixture of chloroform and methanol as a solvent.
  • this method cannot be used in food because of the toxicity of the solvents used.
  • the lipid fraction is extracted from marine and aquatic animal material by acetone extraction.
  • the method provides, and the resulting insolubles and granulated fractions disclose the extraction of soluble lipid extracts by applying additional solvent extraction with alcohols, isopropanol, etc., but this also concerns the residual acetone in the krill extract product.
  • the extraction process step is complicated, and the energy cost for removing acetone and additional solvent is expensive.
  • the lipid extracted by acetone will contain a lot of free fatty acids and saturated fatty acids, which will lead to the deterioration of the quality of the krill extract product unless a separate purification process.
  • krill is heated at 80-90 ° C. for 5 minutes and extracted with triple ethanol to dehydrate water and final extraction of krill foil with co-solvent (ethanol) 10% at 280-300 bar pressure with supercritical CO 2 .
  • co-solvent ethanol
  • dehydration with ethanol after catching krill has the advantage of minimizing the degeneration of nutrients of krill
  • extraction with ethanol solvent pre-treatment with phospholipids as well as neutral lipids As it is difficult to obtain a high-purity phospholipid extract, the extracted krill foil also has a disadvantage that requires a separate process for removing the solvent, such as ethanol.
  • the present invention has been made in view of the above-mentioned disadvantages, and in extracting useful nutrients from krill, without using organic solvents such as hexane or acetone, which are harmful to the human body, among the useful nutrients that krill has, Exploring and separating tarxanthin, omega-3 polyunsaturated fatty acid ( ⁇ -3 PUFA), phospholipids, etc., and separating and refining each nutritional ingredient as necessary
  • the present invention has a purpose of establishing a method of allowing protein to be recovered without remaining solvent from krill foil remaining after extraction, while allowing mixing.
  • the above object of the present invention is suitable for extracting nutrients to be extracted from krill, while extracting only useful nutrients from krill by applying an extraction method using supercritical carbon dioxide as a solvent that is harmless to the human body, the supercritical carbon dioxide Optimized the method of fractionation, extraction and separation using different solubility difference according to temperature and pressure in the process, and the fractionation process continuously without moving the filling sample with the raw material once filled in the extractor By the process to be achieved.
  • the present invention provides a novel pretreatment method that improves the problems of the krill ethanol dehydration method.
  • Method of pretreatment of krill according to the present invention is characterized in that the krill is immediately caught by 80 ⁇ 100 °C, pulverized and dried immediately on the ship to prepare a powder.
  • Another method of pretreatment of krill according to the present invention is to catch the krill as soon as 80 ⁇ 100 °C to quickly freeze without the addition of seawater or fresh water is added to the immediate freezing immediately stored and stored in the frozen state, then After drying or crushing, the surface water is removed by a dehydrator and immediately dried by hot air drying to obtain a water content of less than 5% to prepare a powder.
  • this krill pretreatment process it is possible to obtain a high purity phospholipid extract in the subsequent extraction process.
  • the present invention also provides a method of extracting krill powder using supercritical carbon dioxide and ethanol as an extraction solvent.
  • Extraction method of krill the step of pre-processing the raw material krill to powder; Filling the krill powder into an extractor; Extracting krill powder using supercritical carbon dioxide and ethanol as an extraction solvent; Supplying only the supercritical carbon dioxide to the extractor to remove ethanol from the remaining krill extraction foil to obtain krill protein extraction foil; And concentrating the krill extract under reduced pressure to remove ethanol to obtain krill oil.
  • Extraction using the supercritical carbon dioxide and ethanol as the extraction solvent is preferably carried out under a temperature of 50-70 °C and 250 to 800 atmospheres, the average flow rate of ethanol is preferably 5-50% of the flow rate of carbon dioxide. Do.
  • Krill oil and krill protein extract foil are finally obtained from krill powder through the same method as described above.
  • the method of extracting krill comprises the steps of pretreating the raw material krill to powder; Filling krill powder into an extractor; Performing primary extraction of krill powder using supercritical carbon dioxide as an extraction solvent to obtain krill oil; Performing secondary extraction using supercritical carbon dioxide and ethanol as extraction solvent to obtain krill oil, and supplying supercritical carbon dioxide to the extractor to remove ethanol from krill extraction foil to obtain krill protein extraction foil continuously It provides a method of extracting krill, characterized in that performed.
  • Extraction using the primary supercritical carbon dioxide and extraction using the secondary supercritical carbon dioxide and ethanol are preferably performed under pressure conditions of 250 to 800 atm, respectively.
  • Krill oil is obtained as a primary extract through the same method as described above, and krill protein extract foil containing protein as a main component as krill oil and a residue as a secondary extract is obtained.
  • the method of extracting krill comprises the steps of pretreating the raw material krill to powder; Filling krill powder into an extractor; Performing primary extraction of krill powder using supercritical carbon dioxide as an extraction solvent to obtain krill-flavored concentrated oil; Performing second extraction using supercritical carbon dioxide as the extraction solvent to obtain a high krill astaxanthin oil; Performing tertiary extraction using supercritical carbon dioxide and ethanol as extraction solvent to obtain krill phospholipid high oil, and supplying supercritical carbon dioxide to the extractor to remove ethanol from krill extract foil to obtain krill protein extract foil It provides a method of extracting krill, characterized in that is carried out continuously.
  • the extraction using the primary supercritical carbon dioxide is preferably performed at a pressure condition of 80 to 250 atm, and the extraction using the primary supercritical carbon dioxide is preferably performed at a pressure condition of 250 to 800 atm.
  • krill-flavored concentrated oil is obtained as the first extract
  • krill astaxanthin-containing oil is obtained as the second extract
  • krill phospholipid-containing oil is obtained as the third extract
  • protein as a residue is obtained.
  • Krill protein extract foil which contains as a main component is obtained.
  • Krill oil obtained by the method according to each of the present invention as described above is rich in EPA, DHA omega-3 fatty acids and phospholipids can be used as a raw material for various food processing.
  • krill protein extract gourd can be used as a raw material for various seasonings by fermenting the amino acid as a main component.
  • the present invention focuses on the fact that the lipids contained in krill have both neutral lipids and phospholipids.
  • the free fatty acid, saturated fatty acid, and krill scent components having relatively low molecular weight and high probability of rancidity among the neutral lipids are preferentially.
  • Fractional extraction is followed by fractional extraction of unsaturated fatty acids in triglycerides, and finally fractional extraction of phospholipids.
  • supercritical carbon dioxide having high penetration, diffusion rate, and dissolving ability are used as the solvents of the first and second extractions, and the third extraction solvent easily dissolves phospholipids in addition to the supercritical carbon dioxide.
  • Harmless ethanol was used alone or in a mixed solvent thereof.
  • the primary and secondary extraction steps are for fractional extraction of neutral lipids, using the difference in solubility of the supercritical carbon dioxide according to the pressure, temperature and flow rate of the composition ratio according to the antioxidant and fatty acid type.
  • the fragrance components, free fatty acids and neutral lipids of relatively small molecular weight are screened and extracted under pressure of less than 250 atm.
  • unsaturated fatty acids and astaxanthin having high molecular weight are selected and extracted from neutral lipids under pressure of more than 250 atm. It was.
  • Supercritical carbon dioxide has a high solubility in neutral lipids but little solubility in phospholipids, making it a suitable solvent for extracting only neutral lipids. Therefore, when supercritical carbon dioxide is brought into contact with dry krill powder, only neutralized lipids such as triglycerides are extracted by dissolving and extracting only phospholipids and proteins as a main component in relation to its affinity.
  • neutral lipids are extracted from krill powder through primary and secondary extractions using supercritical carbon dioxide, and insoluble components such as proteins are left through tertiary extracts using a mixed solvent of supercritical carbon dioxide and ethanol or a single ethanol solvent. It is possible to extract high purity phospholipids with low content of neutral lipids. Subsequently, after extracting lipids, krill powder (mainly protein) is contacted with pure supercritical carbon dioxide to remove residual liquid solvent (ethanol, etc.), thereby recovering krill powder containing protein as a main component.
  • the present invention is the contact solvent and pressure, temperature, solvent dosing rate, the total amount of the solvent and the like to extract the fractional fractionation step by step while contacting a mixed solvent of supercritical carbon dioxide and supercritical carbon dioxide and ethanol or a single ethanol in the same extractor It has the characteristics to manufacture various related products of high purity desired by different extraction conditions.
  • Machines and apparatuses used in the present invention is a fluid supply unit consisting of a precooler and a piston pump, an extractor unit consisting of a preheater and an extractor, the fluid in the state containing the omega-3 polyunsaturated fatty acid-bound phospholipids, etc. separated into extracts and gaseous state It consists of a separating section for the separation, a condenser for cooling the evaporated carbon dioxide and a recovery section for storing the carbon dioxide cooled and liquefied. The separation section and the recovery section used in the ethanol extraction process are configured separately.
  • the condenser consists of a vacuum distillation unit for removing ethanol, an ethanol condenser and an ethanol reservoir.
  • Solvents such as carbon dioxide are supplied to the extractor in a liquid or supercritical state having a constant temperature and pressure while passing through the precooler and the piston pump, and have a predetermined temperature while passing through the preheater.
  • a solvent such as carbon dioxide maintains a constant temperature and pressure in the extractor and extracts the neutral lipids and phospholipids contained in the krill powder packed therein.
  • the extract and the supercritical fluid are separated into gases and the separated gases It is recycled as it is converted to a liquid via a condenser.
  • the temperature of the preheater H1 is set to 70 ° C and the precooler H2 to -5 ° C. Carbon dioxide from the vessel passes through the precooler and enters the pump in a complete liquid state at -5 ° C.
  • carbon dioxide is supplied to the extractor at a flow rate of 30 g / min, and is primarily heated while passing through the preheater (H1).
  • V1: BPR the allowable pressure of the decompression device set to 400 atm
  • the carbon dioxide inside the extractor is heated and pressurized until it reaches a supercritical state of 400 atm and 70 ° C.
  • the device discharges more than a certain pressure to the outside and the pressure inside the extractor is maintained at 400 atm.
  • Supercritical carbon dioxide containing neutral lipids is sent to the separator (S1) through a decompression device. At this time, at room temperature and atmospheric pressure, the carbon dioxide loses its dissolving power in the supercritical state and recovers the neutral lipid and astaxanthin dissolved in the supercritical carbon dioxide.
  • the gaseous carbon dioxide is converted into a liquid phase through the condenser (C1) and stored in the recovery tank (R1) and used again for extraction.
  • the phospholipid is decomposed into the liquid and gaseous carbon dioxide of the ethanol containing the dissolved component in the separator (S2) while decompressing the mixed solvent of supercritical carbon dioxide and ethanol through a depressurization device. And liquefied to the recovery tank (R2) to be used for extraction.
  • the liquid ethanol and elution components are sent to the ethanol evaporator (E1) for concentration and recovery.
  • the evaporated ethanol is liquefied in the ethanol condenser (C3), collected in an ethanol recovery tank (R3) and sent to the ethanol storage (T1) for extraction. do.
  • the present invention has the effect of easily producing a high quality product having an omega-3 unsaturated fatty acid content of 40% or more and a phospholipid concentrate product having a phospholipid content of 80% or more, and by optimizing the extraction conditions, etc.
  • the present invention can be fractionally extracted by a continuous operation process in the same extractor, it is possible to compactly design the whole extraction equipment.
  • carbon dioxide is easy to remove because it is a gas at room temperature and atmospheric pressure, and in the case of ethanol, it is easy to remove by vacuum distillation.
  • the organic solvent is often left in a significant proportion in the residue of the extraction tank.
  • the present invention uses supercritical carbon dioxide in the final extraction step, so that almost no solvent, such as ethanol, remains in the final krill foil after the extraction process, so it can be used without a separate solvent removal process has excellent economic efficiency.
  • FIG. 1 is a structural diagram of an extraction apparatus using a pressurized liquid and supercritical carbon dioxide used in the present invention.
  • Example 2 is a flowchart illustrating an extraction process of krill powder according to Example 2 of the present invention.
  • Example 3 is a flowchart illustrating an extraction process of krill powder according to Example 3 of the present invention.
  • Example 4 is a flowchart illustrating an extraction process of krill powder according to Example 3 of the present invention.
  • V1 Pressure regulating valve with Back Pressure Regulator
  • R1 A place to recover liquefied carbon dioxide and send it to a circulation pump
  • R2 A place to recover liquefied carbon dioxide and a small amount of ethanol and send it to a circulation pump
  • 130 g of krill powder was placed in the extractor under conditions of a temperature of 70 ° C. and a pressure of 400 atm, with an average flow rate of 30 g / min of carbon dioxide and an average flow rate of 10%, 20%, 30%, 40% and 50%, respectively. Extraction was carried out for a time (390 minutes, 195 minutes, 130 minutes, 97.5 minutes and 78 minutes) is injected into the ethanol 6 times compared to the sample filled with ethanol as the extraction solvent.
  • 130 g of krill powder was placed in the extractor and extracted for 3 hours using 70 g of ethanol at an average flow rate of 30 g / min and 50% of the ethanol flow rate at an average flow rate of carbon dioxide under a temperature of 70 ° C. and a pressure of 400 atm.
  • pure carbon dioxide having an average flow rate of 30 g / min was fed for 30 minutes to remove ethanol from the remaining krill extraction foil.
  • the pressure of the extractor was adjusted to atmospheric pressure to recover the krill extract foil, and the mixed liquid remaining in the separator was distilled under reduced pressure to prepare a krill extract from which ethanol was removed.
  • the extractor was subjected to secondary extraction for 2 hours using a solvent mixture of 50% of the average flow rate of 30 g / min carbon dioxide and 50% of the flow rate of the average flow rate carbon dioxide under a temperature of 70 ° C. and a pressure of 400 atm. Pure carbon dioxide was supplied to the extractor at an average flow rate of 30 g / min for 30 minutes to remove ethanol from the remaining krill extraction foil, and then the pressure of the extractor was adjusted to atmospheric pressure to recover the krill extraction foil. The remaining mixed liquid in the separator was distilled under reduced pressure to prepare a secondary extract B from which ethanol was removed.
  • 130 g of krill powder was placed in an extractor and subjected to a primary extraction for 2 hours using supercritical carbon dioxide having an average flow rate of 30 g / min as an extraction solvent under a temperature of 70 ° C. and a pressure of 200 atm.
  • the primary extract A was separated and recovered from carbon dioxide by transporting under reduced pressure to a separator. Subsequently, the pressure was increased to 400 atm at a temperature of 70 ° C., and secondary extraction was performed for 2 hours using supercritical carbon dioxide having an average flow rate of 30 g / min as an extraction solvent, and then the supercritical carbon dioxide was transferred to a separator under reduced pressure. Tea extract B was separated and recovered from carbon dioxide.
  • the method of extracting krill using supercritical carbon dioxide according to the present invention can provide a product richer in DHA omega-3 fatty acids and containing a high concentration of phospholipids than in the conventional extraction method using an organic solvent.
  • the present invention can be fractionated, extracted and recovered step by step, such as krill oil and krill protein products, further concentrated krill fragrance oil, high astaxanthin oil, high phospholipid oil, etc. It is a very useful invention for the special food processing industry because it has an excellent effect.

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Abstract

L'invention concerne un procédé d'extraction de matières actives de krill. Elle concerne un procédé permettant de sélectionner, de fractionner, d'extraire et de séparer des matières nutritives spéciales, à chaque étape d'extraction, à l'aide de dioxyde de carbone supercritique et d'un solvant unique à base d'éthanol ou d'un solvant mixte à base d'éthanol et analogue, par un système d'extraction utilisant du dioxyde de carbone supercritique. L'invention permet d'obtenir des produits huileux riches en astaxanthine et en acides gras insaturés oméga-3, des produits de phospholipides de grande pureté comportant au moins 80% de phospholipides et d'autres produits de protéines, par la variation des conditions d'extraction telles que solvant, pression, température, vitesse d'injection de solvant et quantité totale de solvant, etc. L'invention concerne aussi un procédé de séparation des produits. L'invention est avantageuse en ce qu'elle rend superflus des processus d'extraction de solvant et permet de produire des produits de protéines de qualité supérieure contenant peu de solvant résiduel.
PCT/KR2009/005528 2008-09-30 2009-09-28 Procédé d'extraction et de séparation de matières actives de krill, et produits associés WO2010038964A2 (fr)

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KR20080096322 2008-09-30
KR10-2008-0096322 2008-09-30
KR1020090019347A KR100951727B1 (ko) 2008-09-30 2009-03-06 크릴로부터 유용성분 추출분리방법 및 관련 제품
KR10-2009-0019347 2009-03-06

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WO2010038964A3 WO2010038964A3 (fr) 2010-07-29

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8609157B2 (en) 2009-10-30 2013-12-17 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
CN104478774A (zh) * 2014-12-12 2015-04-01 吕梁广汇生物科技股份有限公司 一种以万寿菊鲜花为原料提取叶黄素的方法
CN107903997A (zh) * 2017-12-21 2018-04-13 山东师范大学 一种以南极磷虾脱脂干虾渣为原料再制备油脂的方法
CN115232668A (zh) * 2022-07-20 2022-10-25 中船黄埔文冲船舶有限公司 船载磷虾产品生产线及虾油生产方法

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8609157B2 (en) 2009-10-30 2013-12-17 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US8772516B2 (en) 2009-10-30 2014-07-08 Tharos. Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US8865236B2 (en) 2009-10-30 2014-10-21 Tharos Ltd. Solvent-Free Process for Obtaining Phospholipids and Neutral Enriched Krill Oils
US9011942B2 (en) 2009-10-30 2015-04-21 Tharos, Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US9150815B2 (en) 2009-10-30 2015-10-06 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
CN104478774A (zh) * 2014-12-12 2015-04-01 吕梁广汇生物科技股份有限公司 一种以万寿菊鲜花为原料提取叶黄素的方法
CN107903997A (zh) * 2017-12-21 2018-04-13 山东师范大学 一种以南极磷虾脱脂干虾渣为原料再制备油脂的方法
CN115232668A (zh) * 2022-07-20 2022-10-25 中船黄埔文冲船舶有限公司 船载磷虾产品生产线及虾油生产方法
CN115232668B (zh) * 2022-07-20 2024-05-24 中船黄埔文冲船舶有限公司 船载磷虾产品生产线及虾油生产方法

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