CN105029138A - Deodorization and stabilization of marine oils - Google Patents
Deodorization and stabilization of marine oils Download PDFInfo
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- CN105029138A CN105029138A CN201510386282.8A CN201510386282A CN105029138A CN 105029138 A CN105029138 A CN 105029138A CN 201510386282 A CN201510386282 A CN 201510386282A CN 105029138 A CN105029138 A CN 105029138A
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- marine oils
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
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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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
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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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/21—Removal of unwanted matter, e.g. deodorisation or detoxification by heating without chemical treatment, e.g. steam treatment, cooking
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
- C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
Abstract
The invention relates to a process for the preparation of deodorized and stabilized food-grade marine oils by submitting marine oils to a counter-current steam distillation (CCSD) in a thin film column containing a structured packing and, if desired, adding antioxidant(s), to the food-grade marine oils thus obtained and to their uses in the food/feed, cosmetic and/or pharmaceutical industry.
Description
Technical field
The present invention relates to and a kind ofly make marine oils deodorizing and stable method and the marine oils that obtains thus.
Background technology
Marine oils has very attracting benefit, because polyunsaturated fat oil (PUFA) (specifically eicosapentaenoic acid (EPA) and DHA (DHA)) source has great meals meaning, it comprises the PUFA ester with its naturally occurring monoglyceride form and ethyl ester form.But according to the rejecting of its source, its degree of purification and naturally occurring accessory substance and denatured products, the quality of marine oils in taste and stability has different significantly.Because PUFA comprises some carbon-carbon double bonds, so they are easy to be oxidized at ambient conditions thus produce fishlike smell.
At present, there is a large amount of evidence proves: increase the level of these compounds in meals and have beneficial effect to health, and can intervene blood pressure, atherosclerotic and thrombosis thus reduce the death caused by coronary heart disease.
A kind of method fish oil being stablized avoid occurring oxidation and unfavorable development of exploitation is urged in the concern day by day increased these compounds.
In recent years, carrying out to have in stable fish oil and PUFA some improvement by adding stable material.
Hamilton etc. at J.Am.OilChem.Soc. (JAOCS),
75(7), a kind of extraordinary Ternary-Additive mixture (2% Delta-Tocopherol, 0.1% ascorbyl palmitate, 0.5% lecithin) for preventing fish oil to be oxidized is disclosed in 813-822 (1998).Although do not have remarkable peroxidating in time period of 6 months at the fish oil adding refining after said mixture at 20 DEG C, this mixture successfully can not suppress peculiar smell (off-taste and off-smell).Peculiar smell is there is in 3 week.
EP340635A describes a kind of so method: at temperate condition (at 30 DEG C-150 DEG C, preferred 60-100 DEG C, 2-5 hour) under by vacuum steam distillation, the oil (especially fish oil) containing EPA and DHA is processed, thus reduce the volatile flavor compound of the low and low polarity of boiling point, then make described oil contact with adsorbent (such as silica gel), thus reduce the volatile flavor compound of boiling point height and high polarity.In a specific embodiment, the oil of purifying and Rosmarinus officinalis extract antioxidant combination thus.But the oil that this fishy smell is reduced to a great extent has following feature: the taste of rosemary extract and smell make it be unsuitable for numerous food product application, are especially unsuitable for dairy products.
According to process described in european patent application 612346 (=WO93/10207), make the refining marine oils adopting treatment of silica carry out soft vacuum steam distillation (140-210 DEG C) and adopt the mixture of lecithin, ascorbyl palmitate (AP) and alpha-tocopherol to carry out stable make Rancimat improved stability (according to embodiment 1-8: 4.9-14 hour at 100 DEG C) and making the application performance being mainly used in healthy food replenishers good.But, in the dairy applications (such as yogurt and milk beverage) responsive especially to smell, observe and occur in some cases making us unacceptable, undesirable aroma and flavor.
EP999259 (=US2003/161918A1) describes preparation by the following method and the stable food-grade marine oil containing PUFA, described method comprises: use treatment of silica marine oils, makes it at the temperature of 150 DEG C and 190 DEG C, carry out the deodorizing of 2 hours intermittent vacuum steam under the existence of rosemary or Salvia japonica extract (if needing to add ascorbyl palmitate and mixed tocopherol).This process obtains stable food-grade marine oil, and it has the Rancimat induction period of useful aroma and flavor feature and 4.1-6.2 hour.The quality of these oil is best up to now, and they are suitable for various food applications, comprise dairy products, such as milk and yogurt.
Consider the ever-increasing demand of high-quality food-grade oil containing PUFA, need a kind of in output and more effective production method in the short time.The invention provides such method and corresponding product.
According to Ullmann'sEncyclopediaofIndustrialChemistry, 5th plate, A10 rolls up, 204-206 page (1967), interval deodoriser is substituted, this is because more effective stripping and heat recovery can save steam with semicontinuous and continuous deodoration system.Mentioned semicontinuous and example that is continuous deodorizer is made up of the iron-clad being provided with stainless steel tower tray (tray) and supply thereof.Campro deodoriser has tower tray (tray-in-shell) design in continuous print shell, and it is combined with unique film stripping concept by plug flow.
At Bailee'sIndustrialOilandFatProducts, the volumes such as Y.H.Hui, JohnWiley & Sons, NewYork, 1996 (339-390 page) the 4th review in volume the 6th chapter (deodorizing) commercial deodorizing system to the development history of the nineties in last century.
United States Patent (USP) 4,996,072 disclose a kind of by multi-step process deodorizing and/or reduce the method for cholesterol levels of fat and oil (being specially fish oil or marine oils) under vacuo, described method comprises: the temperature above-mentioned oil being heated to about 400-500 ℉ (204-288 DEG C), formed pretreated fluid phase by the oil heated described in flash distillation, then adopt 1-15% (by weight) counter-current steam to carry out film stripping to this oil under 1-7mmHg.Thus, obtain the oil with following feature: the taste of clean fish oil is gentle, cholesterol level is low and content that is n-3 unrighted acid in raw material is at least 95%.
Similarly, close related U.S. patent 5,436,018 discloses by the method for reducing cholesterol levels in oil (concrete fish oil or marine oils), obtain cholesterol lower, be deodorant and there is the oil of good taste, described method comprises: introduce above-mentioned oil on the top of adverse current film steam stripping device under the pressure of at the temperature of at least 400 ℉ (204 DEG C) and at least 1mmHg, introduce steam simultaneously in its underpart.Consider the retention time shorter (5 minutes or shorter) of oil, think that this method is favourable compared with traditional deodorization technology, because the degraded of useful n-3 unrighted acid is minimum.
United States Patent (USP) 4,810,330 describe a kind of by make the liquid of falling liquid film and continuous print stripped vapor contact in countercurrent tower detailed description of the invention that the high boiling liquid added relatively small amount carries out continuous deodorization process, described high boiling liquid is such as aliphatic acid, edible oil, fat, glyceride and other high boiling ester, specifically palm oil and other vegetable oil, it also comprises the liquid condensate (compound of free fatty, water, pigment, scent of and/or taste) of about 5wt% except fat oil glyceride.
Similar approach and device are from such as US4,394,221, US4,599,143 and GB2176713A (=DE3522897A1) in know, these method and apparatus by carrying out counter-current steam stripping in falling-film tower, concise to remove its deodorizing of volatile impurity/make/carry out physics to it from higher boiling edible oil, fat and ester (being specially vegetable oil and hydrogenated fish oil).
JP2007014263A describes and is a kind ofly derived from the edible fat of plant and animal and the method for oil by carrying out the film tower containing stacked packing material and tray type device combining purifying, this edible fat and oil comprise content of trans fatty acids be no more than 1 quality % fish oil (be not purified, by depickling, by decolour, be deodorant, be hydrogenated).Temperature in this tower is 225-252 DEG C, and pressure is no more than 18hPa, and oily heap(ed) capacity is 12-28m
3/ m
2, the height of transfer unit of regular packing is 1-7m.Temperature in tray apparatus is 210-247 DEG C, and pressure is no more than 18hPa.The purification process time is 15-120 minute.
Xu etc. (JAOCS,
78(7), 715-718 [July calendar year 2001]) have studied by distillation purifying ad hoc structure in the traditional interval deodoriser adopting stripped vapor lipid during, the cause of acyl group transfer and impact.Result shows to use more effective isolation technics to improve the quality of the Structured lipid be purified, and draw the following conclusions: in order to reduce vapo(u)rizing temperature, vacuum should be low as much as possible, and in order to shorten distillation time, should use film principle in packed columns.
Ahrens is in Fett/Lipid101. (7), and 230-234 (1999), reviews the history of seed oil being carried out to film deodorizing in WILEY-VCHVerlagGmbH, Weinheim.Film deodoriser develops into 20 reagent the mid-80s and is used in commercial Application from 20 century 70s.Latest type be SoftColumn
tM, one is developed the deodoriser for moderate, low cost processing seed oil (being specially sunflower oil, soybean oil and rapeseed oil) especially, and it comprises structurized filler.Carrying out very effective stripping to free fatty can cause oil shorten in vacuum, the total retention time improved at temperature and steam consumption can be reduced to 1/3rd of traditional deodoriser aequum.Gained oil has low acidity, low colour, good taste and stability and lower trans-fatty acid level.By the outstanding distillation efficiency of structuring filling, deodoriser can also be adjusted simply by adjustment stripped vapor, thus for removing tocopherol or retaining both tocopherols.Stenberg etc. (INFORM, 7 (12), 1296-1304, Dec.1996) have been found that: on the one hand packed column is used for tower tray stripping system and carries out film stripping and have advantage; Another aspect has advantage with the filler that structurized filler substitutes random placement in the film deodorizing of edible seed oil.
WO2006/1185518 describes a kind of by making the semicontinuous or continuation method of organic or inorganic fluid deodorizing as follows in the tower with one or more tower tray: described fluid is contacted with gas jet, described gas jet can be water vapour, preferably introduces in the bottom of tower tray.
Sulzer company provides a kind of equipment comprising packed column containing structure shape filler on its website (www.sulzerchemtech.com), and it by removing free fatty and prepare edible fat and for oily deodorizing under low-down vacuum from vegetable oil.Sulzer additionally provides the various dissimilar structuring filling formed by different materials that can be used in above-mentioned tower.
These structurized tower packings make liquid oil phase be uniformly distributed on the large surface of film, thus realize contacting with gas phase extensive and material exchanges.Here it is adopts the deodorization process of above-mentioned tower under vacuum and steam counter-current condition reason more more effective than corresponding batch technology.
In interval deodorization process, the time of contact of oil phase and gas phase is generally some hours, and counter-current steam distillation (CCSD) technique in its in the scope of some minutes.But, shown in EP999259, in the interval deodorisation process that there is herb extracts (such as rosemary or Sage extract), active deodorizing and the stable component of said extracted thing can not be removed, and herbal medicine taste component and cause the component of fishlike smell to be removed by from marine oils.Do not have it is anticipated that, following situation is there is under the condition of highly effective CCSD, namely added marine oils wherein from herbal extract deodorant and optional antioxidant, deodorizing and stable component also can not be removed together with fishlike smell component by with herbal medicine taste component under CCSD condition.Find surprisingly, above-mentioned oil or marine oils is made to carry out CCSD under the existence of herbal extract deodorant, thus form the food-grade oil of high-quality, namely there is the oil of following feature: aroma and flavor quality is very good, Rancimat induction period is long and FAST index is less.
Summary of the invention
Therefore, the present invention relates to a kind of for the preparation of to be deodorant and by the method for stable food-grade marine oil (composition), described method comprises: make marine oils preferably under the existence of herbal extract deodorant (if needing to add antioxidant, ascorbyl palmitate and/or tocopherol and/or citric acid), such as, in the film tower containing structuring filling, carry out counter-current steam distillation (CCSD).Term " marine oils is under the existence of herbal extract deodorant " comprises the marine oils containing herbal extract deodorant or herb extracts and has added the marine oils of herbal extract deodorant and herb extracts.
The invention still further relates to a kind of that obtain by this method or by being deodorant of obtaining of this method and by stable food-grade marine oil (composition), relate to they as meals or healthy replenishers and for the manufacture of such as food, condensed food (functional food) preparation purposes and relate to meals and healthy replenishers and by the food of these marine oils strengthening itself.
Particularly, the present invention relates to every as follows:
1. for the preparation of to be deodorant and by a method for stable food-grade fish oil, described method comprises: make marine oils carry out counter-current steam distillation (CCSD) in the film tower containing structuring filling, if need to add antioxidant.
2. the method as described in item 1, wherein makes described marine oils under the existence of herbal extract deodorant, carry out described counter-current steam distillation.
3. the method as described in item 1 or 2, described method is continuous flow upstream steam distillation.
4. the method as described in item 2 or 3, wherein said herbal extract deodorant is rosemary and/or Sage extract.
5. the method according to any one of item 1-4, wherein said antioxidant comprises ascorbyl palmitate and/or tocopherol and optional citric acid.
6. the method according to any one of item 1-5, wherein said marine oils comprises at least one PUFA (polyunsaturated fatty acid).
7. the method according to any one of item 1-6, wherein said marine oils is food oil containing PUFA or Arrcostab, preferred ethyl ester concentrate.
8. the method according to any one of item 1-7, wherein said distillation 0.1 and 10hPa low pressure under, preferably 0.5 and 10hPa low pressure under, more preferably 1 and 5hPa low pressure under carry out.
9. by being deodorant of obtaining of method according to any one of item 1-8 and by stable food-grade marine oil.
10. by being deodorant of obtaining of method according to any one of item 1-8 and by stable food-grade marine oil.
11. 1 kinds be deodorant and by stable food-grade marine oil, it is characterized in that, FAST index
tMlower than 1.5, preferred 1.3-1, more preferably 1.1-1, most preferably be 1.0.
12. marine oils according to any one of item 9-11, it is characterized in that, Rancimat is greater than 6.2 hours induction period.
13. marine oils according to any one of item 9-11, is characterized in that, Rancimat induction period is in the scope of 10.15-20 hour.
14. according to any one of item 9-13 be deodorant and manufactured the purposes in meals or healthy replenishers, condensed food and feed (functional food/feed) and cosmetics or pharmaceutical preparation by stable food-grade marine oil.
15. 1 kinds of meals or healthy replenishers, its comprise according to any one of a 9-13 be deodorant and by stable food-grade marine oil.
16. 1 kinds of strengthening/functional food, its comprise according to any one of a 9-13 be deodorant and by stable food-grade marine oil.
17. 1 kinds of cosmetics, its comprise according to any one of a 9-13 be deodorant and by stable food-grade marine oil.
18. 1 kinds of pharmaceutical preparations, its comprise according to any one of a 9-13 be deodorant and by stable food-grade marine oil.
The wiped film distillation column of 19. interstitital texture fillers manufacture according to any one of item 9-13 be deodorant and by the purposes in stable food-grade marine oil.
20. 1 kinds for the method by the meals being rich in n-3PUFA, health or the nutritious supplementary pharmaceutical described in intermediate food or its component production item 15 or 16 or strengthening/functional food, described method has following feature: the marine oils adding certain quantity of fluid form, former state, emulsion or gel form or dried forms in described intermediate food or its component, the n-3 aliphatic acid wherein containing aequum; It is made to disperse by acutely mixing; If needed, the blend obtained thus is processed further also aft-loaded airfoil and become required product.
Detailed Description Of The Invention
Term used herein " marine oils " should be construed broadly, it comprises the component being obtained oil and the above-mentioned marine oils containing at least one long-chain (LC) PUFA by marine organism, described marine organism comprises marine alga, planktonic organism, fish, preferred cold water fish and sea dog, comprise genetic modification/genetically modified organism, and the part of organism or fragment.Broadly say, term " marine oils " comprises the oil that can obtain from any organism, and this oil can be degraded thus be produced the aldehydes and ketone that cause " fishlike smell " or other unhappy taste.Above-mentioned organism comprises animal, microorganism (such as yeast) and plant and part (such as seed) thereof.
Term " polyunsaturated fatty acid (PUFA) " refers to have n-3, n-6 and n-9 (or Ω-3, Ω-6 and Ω-9) aliphatic acid of at least two C-C double bonds and the ester with glycerine or alkanol (preferred low-grade alkane alcohol such as ethanol) thereof, preferred n-3 aliphatic acid.The example of LCn-6PUFA is linoleic acid (C18:2), gamma-Linolenic acid (GLA, C18:3), two height (dihomo)-gamma-Linolenic acid (DGLA, C20:3) and arachidonic acid (ARA, C20:4).The example of LCn-3PUFA is alpha-linolenic acid (C18:3), parinaric acid (C18:4; 6,9,12,15), eicosapentaenoic acid (EPA, C20:5; 5,8,11,14,17), clupanodonic acid (DPA, C22:5; 7,10,13,16,19) and DHA (DHA, C22:6; 4,7,10,13,16,19).In recent years, especially EPA and DHA causes showing great attention to of food industry, and especially pays close attention to the related to the present invention marine oils, particularly its conc forms that contain above-mentioned EPA and DHA of glyceride and Arrcostab (such as methyl esters or ethyl ester) form.PUFA glyceride (it can be natural or reconstruct) comprises monoglyceride, diester and three esters, special concern the latter.Methyl esters and ethyl ester are obtained by ester exchange by marine oils.
In the method for the invention as the marine oils of raw material or its fraction can be add wherein herb extracts (such as rosemary or Sage extract) deodorant not concise, do not come unstuck, unacidified, be neutralized, partially oxidized, concise by part, concise, by bleach and/or the marine oils that is deodorant.Preferred raw material has carried out concise in advance, such as carries out adsorbing and/or carrying out short-path distillation on carbon containing or carbon-free silica gel.Before CCSD, the amount of the herb extracts added is depended on its quality.It is not immediately clear the chemical property and the mechanism of action thereof that make herb extracts have the component of odor removal efficient.The rosemary be deodorant or the amount of Sage extract, in the scope of 0.1-0.4% (w/w), can obtain excellent result.But this scope does not have restricted.Optimum amount can be determined according to each case.When PUFA ethyl ester has such as 250ppmHerbalox, still obtain good rancimat numerical value.
Be deodorant and by stable food-grade marine oil, there is following feature: FAST index
tMlittle, be namely less than 2 or 1.5, be preferably 1-2,1-1.5,1-1.3; More preferably 1-1.1, most preferably is numerical value 1.0.This index is definitely relevant to the trained taste panel for fishlike smell classification.Abbreviation " FAST " expression " fatty acid odor and taste ".The scent molecule solid phase extractions of automation and ammonia negative chemical ionization-mass spectrography combine by the method.This makes it possible to the concentration measuring the three kinds of concrete molecules (4-heptenal, 2,6-nonadienals and 3,6-nonadienal) giving fishlike smell.Algorithm converts these data the scoring of reaction density to.FAST index
tMtaste panel's standardization by the mankind, make the score of 1-7 reflect the scope of human subjects to taste sensitivity.Score 1 represents does not have fishlike smell (namely without) completely; Score 2 represents " very slight "; Score 3 represents " slightly "; Score 4 represents " medium "; Score 5 represents " weight "; Score 6 represents " very heavy "; And score 7 represents extremely heavy fishlike smell.Although the sense of taste of the mankind is saturated for 7 or score higher again, FAST index
tMscore can be measured up to the taste of hundreds of and scent molecule.In the magazine INFORM (12,244-249, March calendar year 2001) of AmericanOilChemists'Society, N.Macfarlane etc. propose a kind of test that fishiness is quantized, and which describe FAST index
tMtechnology and disclose and become the algorithm of score by analyzing data transformations.Fishiness index=1+ (0.312 × A)+(0.11 × B)+(0.03 × C), wherein, A=2,6-nonadienal (ppb); B=4-heptenal (ppb); C=3,6-nonadienal (ppb).
Because 2,6-nonadienal, 3,6-nonadienal and 4-heptenal cause undesirable taste and/or the low stability of marine oils and the main molecules measured in FAST index, and the removal of very high level (remove completely or) is the detailed description of the invention realized by the present invention so the removal of these compounds.The marine oils that FAST index is 1.0 can be obtained, this quality never reached before representing by this method.
Therefore, another embodiment of the present invention is by above-mentioned molecule removing or is reduced to FAST index
tMbe the concentration of 1.0, wherein 1.0 should be understood to be less than 1.1 but comprise 1.01.
Except the three kinds of molecules described in FAST test, there is other and there is different taste profile and aldehyde and the ketone that can cause peculiar smell (if existing to analyze confirmable amount).These molecules comprise alkanal (valeral-blue cheese taste; Hexanal-by mowing taste; Heptane-chemicals, unhappy; Octanal-chemicals, plastics taste; Aldehyde C-9-chemicals, plastics taste); Olefine aldehydr (2-hexenoic aldehyde-bitter taste; 2-heptenal-bitter taste; 2-octenal-nut astringent taste; 2-nonenyl aldehyde-chemicals, unhappy); Two olefine aldehydrs (2,4-heptadienal-putrefactive odor; 2,4-nonadienal-putrefactive odor) and ketone (1-penten-3-one-chemicals, plastics taste; 1-octene-3-ketone-mushroom taste; 3,5-octadiene-2-ketone-metallic taste).It is very important for the soft oil of production that they are reduced to below the sensation limit, quantitatively determine these compounds whether exists contribute to differentiation of the present invention be deodorant and by stable marine oils and prior art by the marine oils stablized/be deodorant.In this food-grade marine oil, these components are reduced to detectable limit.
On the other hand, its stability is determined by the numerical value of the Rancimat induction period (RIT) of marine oils.There is the rancid time interval in this numeric representation oil, in hour.This numerical value utilizes RancimatRTM device (MetrohmLtd., CH-9101Herisau, Switzerland) to measure at 100 DEG C.Can to be extrapolated the stability of this oil under lower temperature (such as 20 DEG C or 10 DEG C) by the numerical value at high temperature measured.Marine oils of the present invention has following feature: the Rancimat stability at 100 DEG C is greater than 2, is preferably greater than 3.8, more preferably greater than 5.2,6 or 6.2, most preferably in the scope of 10.15-20 hour.
In another embodiment of the present invention, marine oils of the present invention is further processed into powder, pre-composition, particle, bead (beadlet), replenishers form, tablet, pill, emulsion, solution or emulsion according to known technology.
Comprise/organic vehicle be commonly used in food, animal feed, cosmetics or pharmaceutical preparation can be comprised further based on the composition of marine oils of the present invention and preparation or preparation.
As mentioned above, by adding the method that stable/antioxidant makes marine oils stablize to be this area existing level to adopt, itself and the present composition are the preferred embodiment of the present invention.The instantiation of stabilizing agent comprises ascorbic acid, ascorbyl palmitate, BHT, t-butylhydroquinone (TBHQ), Rosmarinus officinalis extract (such as from the Herbalox " O " of KalsecInc), Kalamazoo, Michigan, Sage extract, tocopherol, lecithin and citric acid.
The present invention is by breakthrough that the is stable and commercial run of the marine oils be deodorant to preparation.By using film reverse flow technique, improve the oil mass of unit interval production to a large extent.According to Sopwith staff used cun, the output being greater than 10kg per hour can be realized.Preferably, the output of product is greater than 100kg/ hour, is even 1000kg/ hour, and this represents industrially significant marine oils amount or marine oils fraction.Preferred Package size comprises, and is greater than 4kg, is preferably greater than 19kg, more preferably greater than 170kg, is most preferably greater than the sample of 900kg.
The film tower containing structuring filling (being specially efficient configuration filler) of all kinds can be used in the practice of the invention, formed by this tower and treat deodorizing and the film treating stable marine oils, thus make it fully contact with gas phase (steam).There is many structuring fillings formed by the different materials becoming known for above-mentioned film tower.In a detailed description of the invention, corrugated sheet metal filler obtains excellent result.In multiple available commercial packed column in the methods of the invention, specifically mention following filler as an example: SulzerMellapak, SulzerMellapakPlus, Sulzergauze model BX, BXPlus or CY, SulzerMellagrid, Nuttergrid,
rombopak or ZehuaSepak, the purposes of above-mentioned filler represents the preferred embodiment of the present invention.
Can contact with steam in every way.But, in a concrete effective mode, marine oils or part marine oils are added top or the top of tower, add steam in bottom or bottom, thus run with counter-flow pattern.
Although the present invention can carry out in the mode of batch technology or half-continuous process, preferably carry out this method in a continuous manner.In an especially preferred embodiment, tower is with the formal operations of continuous flow upstream turret, and technique is counter-current steam distillation (CCSD).
The present inventor infers, the quality of the theoretical stage in film tower on this technique has impact.In one preferred embodiment, the film tower containing highly effective structuring filling adopt be greater than 10, be preferably greater than 50, more preferably from about 60 or the NTS (theoretical stage) of 60-100 operate.Particularly preferably be, this tower does not have physical barrier (physicalplate) at all, but currently thinks that 1 physical barrier can not reduce the advantage of the inventive method, and even 2 dividing plates are also acceptable.
Observe, between at the bottom of tower top and tower bottom pressure difference (pressure drop) in some embodiments for composition at the bottom of production there is impact.Therefore, in a preferred embodiment of the invention, the pressure drop at the bottom of tower and between tower top is less than 2mbar/m, preferably 0.01-1mbar/m, more preferably 0.8-1.0mbar/m.
Also observe, the ratio between marine oils and steam makes the result of the method different.Presently it is preferred that, operate film tower with following marine oils to steam ratio (w/w) in some embodiments, described marine oils than being 1000:1-10:1, is preferably 500:1-20:1 to steam, be more preferably 200:1-50:1, most preferably be 160:1-70:1.In fact, under the ratio of 120:1.8, extraordinary result is obtained.
This method effectively can utilize raw material.Observe, it can reduce waste material in sizable degree.Certainly, the character of obvious raw material and quality have impact for mass balance.In a preferred embodiment, such as, when by by concise marine oils, the mass balance (difference before and after namely contacting with steam) of marine oils is less than 5 % by weight.
The metric size of tower has impact for the economy of this technique.The tower of preferred use comprises 0.5-20 rice, preferably 1-12 rice, more preferably 2-10 rice, is most preferably greater than the active structure filler of 7 meters.Essential advantage of the present invention is, marine oils is relative with the average contact time of steam short, thus according to this method be deodorant and be shortened to a great extent by the production of units time of stable marine oils.
A reason is: the retention time of marine oils in film tower is relatively short.In a preferred embodiment of the invention, the retention time of liquid phase in tower is 0.5-60 minute, more preferably 5-30 minute, 2-20 minute or 5-10 minute.Especially preferred, the retention time of gas phase in tower is 0.5-10 second.
Various marine oils can be stablized by making it carry out method of the present invention.Preferred marine oils is the mixture of oil and these oil obtained by following fish, and described fish comprises catfish, black carp, sardine, long tail anchovy, Pacific sardine (pilchard), tuna, catfish, squama fish, snapper, whitefish, mackerel, Chilean mackerel (jackmackerel), husky eel, bullhead, salmon, cod, cod, halibut, salmon, sweetfish, blue whitefish, westerly wind, dog shark etc.
The present invention not only relates to the stable of the full oil directly obtained by marine organism and deodorization process, also relates to the stable of marine oils fraction and deodorization process.For a person skilled in the art, the marine oils obviously with various quality can be used for this technique as raw material, and its quality depends on the age of organism.Some have carried out one or more purification step before method process according to the present invention.Therefore, for the inventive method rise expect or raw material comprise be not purified, not by concise marine oils, by the marine oils come unstuck, by depickling marine oils, decoloured and quilt part and completely concise marine oils, the marine oils be neutralized, by the marine oils bleached, by marine oils that is stable and/or that be deodorant and composition thereof.In most preferred embodiment of the present invention, raw material to have carried out adsorbing and comprising herbal extract deodorant on silica, or almost make raw material carry out the present invention before add above-mentioned herbal extract deodorant.
In a specific embodiment of the present invention, marine oils is food oil, and it comprises the polyunsaturated fatty acid of glyceride form, mainly naturally occurring or reconstruct triglyceride.This oil is fed and is processed at the temperature of 80 DEG C-250 DEG C, preferably at the temperature of 100 DEG C-230 DEG C, more preferably at the temperature of 180 DEG C-220 DEG C.
In another embodiment of the present invention, marine oils comprises the polyunsaturated fatty acid of Arrcostab (preferred methyl esters or ethyl ester) form, and it is fed and is processed at the temperature of 60 DEG C-200 DEG C, preferably at the temperature of 80 DEG C-180 DEG C, more preferably at the temperature of 105 DEG C-150 DEG C or 120 DEG C-160 DEG C.
The temperature of described steam 100 DEG C-290 DEG C, preferably 140 DEG C-160 DEG C.
Although method of the present invention can operate at ambient pressure, obvious is that the method under reduced pressure operates the best.Therefore, in a preferred embodiment, film tower runs under the pressure of 0.1-10hPa, preferably under the pressure of 0.5-10hPa, more preferably under the pressure of 1-5hPa.
Various extra Conventional process steps can carry out in conjunction with the execution of the inventive method.A preferred step is degassed.In particular implementation of the present invention, the method comprises makes marine oils degassed, preferably before making marine oils contact with steam, makes it degassed, to O
2be less than 1ppm (stereometer with marine oils), be preferably less than 0.5ppm,
Another kind of particularly advantageous measure is evaporation water.Improvement is, evaporation marine oils, preferably not long ago evaporates marine oils, and is less than 50ppm (weight based on marine oils), preferred 1-50ppm to water making marine oils contact with steam.
Described steam should oxygen-freeization component, such as O
2.Find, the steam deriving from normal tap water is just enough.
In particular implementation of the present invention, stabilizing agent (such as antioxidant) and/or extra deodorant (such as herb extracts) can add after deodorization process.
Consider the organoleptic quality that marine oils of the present invention is favourable and high stability, it advantageously can substitute containing PUFA marine oils itself and contain PUFA marine oils in existing and commercial composite, this area and preparation or preparation, nutritious supplementary pharmaceutical and meals or strengthening/functional food.The present invention is deodorant and is food products market by the staple market of stable marine oils.But also may there is interesting application aspect at feed market.In the context of the present invention, also interested in pet food market.Also there is some application in expection at cosmetics and medical market.In a preferred embodiment of the invention, the composition that method according to the present invention obtains can be used as healthy replenishers, can be included in food applications.Dairy products, infant nutrition product or baby food to the interested especially field of pure and stable marine oils.Instantiation comprises beverage or cereal.Described composition can be advantageously utilised in milk, yogurt and fruit juice, these products to the taste occurred due to the oxidation of marine oils component and degraded and smell change the most responsive.
Therefore, the invention still further relates to comprise of the present invention be deodorant and by the meals of stable food-grade marine oil and healthy replenishers and strengthening or functional food, and relate to a kind of for the preparation of the above-mentioned method being rich in the product of n-3PUFA.
Marine oils of the present invention is rich in PUFA, especially n-3 or ω-3PUFA is rich in, specifically be rich in EPA and DHA, it can be advantageously used in the food (functional food) prepared meals, health or nutritious supplementary pharmaceutical according to known method (such as described in US2007/0298079) or strengthened by n-3 aliphatic acid.According to said method, condensed food is by being made up of intermediate food or its component as follows: in described intermediate food or its component, add a certain amount of marine oils being embedded in matrix, liquid form, former state, emulsion or gel form or dried forms (such as powder), n-3 aliphatic acid (be generally every part of food 5-5000mg, preferably at least 16mg) wherein containing aequum; It is made to disperse by acutely mixing; If need that the substantially uniform blend obtained thus is processed also aft-loaded airfoil further to become required product.Intermediate food can be juice (FC or NFC), the mixture of such as citrus juice, non-citrus juice, milk beverage, energy drink, sports drinks, strengthening/enhancing water drink, soymilk, fermented beverage, Carbonated drinks, above-mentioned fruit juice and drink, yogurt, oat, cereal, cake, fast food, patch, cheese and combination thereof.Further processing and aft-loaded airfoil adopt means known in the art to realize, and it comprises such as pasteurize respectively and cools; Or load container and pack.
In another particular implementation, marine oils of the present invention can be used in the manufacture method of the nutrition of the liquid of type described in WO0147377 and EP1241955, preparation of refreshing oneself (such as orange juice), and the content of above-mentioned patent document is inserted in this description by reference.Wherein said refresh oneself preparation and component in nature and quantitatively similar preparation be the example of marine oils of the present invention in food applications.
Marine oils of the present invention can also be a part for dietary composition and food formulation and can be used in its manufacture, described dietary composition and food formulation also comprise at least one dietary fiber except above-mentioned oil, resistant starch (resistantstarch), FOS, FOS glycosides and inulin such as in the fat reducing meals of the object in order to reduce body weight or control body weight such as described in United States Patent (USP) 2007/0010480, the content of above-mentioned patent document is inserted in this description by reference.There is the example that the dietary composition of at least one n-3 fatty acid component (for marine oils of the present invention) and food formulation thereof are also meals of the present invention or healthy replenishers and strengthening/functional food.
Finally, the example of another particular implementation of the present invention is the nutritious supplementary pharmaceutical described in WO2006/117164 and functional food, the content of above-mentioned patent document is inserted in this description by reference, wherein, described n-3 fatty acid source is marine oils of the present invention, and it also comprises at least one macadamia nut oil and flavor enhancement, such as mayonnaise.
It should be noted that to there is application known in various industry, wherein, add Citrus local flavor with the peculiar smell of the fraction and/or PUFA and PUFA (alkyl) ester and glycerine (three) acid esters that hide marine oils and/or marine oils.Although the final products that can obtain according to the present invention do not need above-mentioned additive, the combination comprising Citrus local flavor (comprising citric acid) is also included in the present invention.In fact, preferably do not add Citrus local flavor, because they can hinder people to find the natural protection function of rotten food.
Finally, marine oils of the present invention can be used to the galenica prepared according to known method in cosmetics and medical industry.
Set forth the present invention further by following examples, but the present invention is not limited thereto.
Embodiment
Embodiment 1
Make the ethyl ester concentrate of the marine oils be distilled at film tower (highly: 8m; Diameter: 250mm; There is the stainless head tower of SulzerBX gauze packing) under following operating condition, carry out counter-current steam distillation:
Temperature: 150 DEG C; Pressure: 1-2mbar; Oil feed rate: 100kg/h; Steam feed speed: 1.8kg/h.
The various ethyl ester concentrates of the marine oils processed under these conditions have excellent sensory qualities and Rancimat stability (see table 1), and it can be improved further by the stabilizing agent added containing antioxidant.
As common in industry, in RancimatRTM device (MetrohmLtd.CH-9101Herisau, Switzerland), at 100 DEG C, assess the stability of the oil obtained thus.The time interval that measured this oil of numeric representation appearance is rancid, in hour.
The oxidation stability of product that table 1 represents the several n-3PUFA of being purchased ester product and obtains according to embodiment 1
Embodiment 2
By preheating in thin film evaporator under the decompressions of the concise marine oils of part at 150 DEG C and 30mbar.After this this oil is made immediately at film tower (highly: 8m; Diameter: 250mm; There is the stainless head tower of SulzerBX filler) under following operating condition, carry out counter-current steam distillation:
Temperature: 210 DEG C; Pressure: 1-2mbar; Oil feed rate: 100kg/h; Steam feed speed: 1.8kg/h.
This oil cools after steam treatment, then measures FAST index (see table 2).Equation used is as follows: fishiness index=1+ (0.31A)+(0.11B)+(0.03C), wherein, and A=2,6-nonadienal; B=4-heptenal; C=3,6-nonadienal.
Adopt this model, the sense organ figure (sensorypicture) of sample that good the inventive method makes and several commercial products can be obtained.Be purchased oil (glyceride) more stable than (alkyl) ester concentrate, the numerical value of its FAST index is in the scope of 20-100, and the numerical value of ester concentrate is in the scope of 60-2500.This means: although oxidation is no more than all these products of a few ppm all have fishlike smell.To this explains why " repetition " sign relevant to n-3 replenishers be common and why in the processing of these products with there will be some problems in consuming.
Table 2 represents the FAST exponential number of sample being purchased ester concentrate and reconstruct triglycerides and obtaining according to the present invention.
| Sample | FAST numerical value |
| EPAX 6000EE(4020) | 2068 |
| EPAX 6000TG | 2396 |
| EPAX 4510TG | 1997 |
| EPAX 1050TG | 1531 |
| Croda 332EE | 111 |
| ONC 4020EE | 125 |
| Croda TG3322 | 82 |
| Croda TG0525 | 1073 |
| Ropufa 75EE | 2-3 |
| Embodiment 1 | 1.5-2 |
| Ropufa food oil | 1.5 |
| Embodiment 2 | 1-1.3 |
Mixed with antioxidant by the material of embodiment 2 and further test thus improve the oxidation stability of these products, some the results are shown in following.Those of ordinary skill in the art know that this selection not delimit the scope of the invention.
TBHQ is considered to a kind of effective antioxidant for a long time.Unexpectedly, we find that it and rosemary oil have strong synergy.Containing 0.2% Rosmarinus officinalis extract, 200ppm ascorbyl palmitate and 1000ppm mixed tocopherol
food oil has the Rancimat induction period of 5.4 hours at 100 DEG C.If substitute tocopherol with 200ppmTBHQ, the induction period so at 100 DEG C extends to more than 10 hours.
Herbal medicine phenol containing various combination and TBHQ's
the results are shown in table 3 of food oil oxidation stability.Rancimat induction period of often kind of situation is all more than 4 hours.
Table 3: by stable PUFA oil and the Rancimat stability of ester
Embodiment 3
(A) the marine oils type DHA for ROPUFA'30'n-3 food oil from Smit & Zoon, NL has following specification:
Outward appearance: yellow oil
Color (Gardner): maximum 11
Taste: can accept
Smell: very light fishlike smell
Acid number: maximum 0.5 (mgKOH/g oil)
Peroxide number: maximum 5.0 (mEq/kg oil)
P-Anisidin value: maximum 30
Unsaponifiable matters: maximum 2.0%
DPA content: maximum 1.0%
EPA content: minimum 10.5%
DHA content: minimum 16.0%
N-3 fatty acid total amount: minimum 30.0%
N-3 long-chain PUFA (DPA+EPA+DHA) total amount: minimum 25.0%
Vitamin A: 100IU/ml at most
Vitamine D3: 50IU/ml at most
Cholesterol: maximum 0.5%
(B) above-mentioned marine oils is by completely concise (being undertaken coming unstuck, bleaching and deodorizing by standard oil refinery practice).But in order to produce the gentleness of human consumption and stable marine oils, it is considered to rough, must carry out extra step and adapt to food applications to make it.
(C1) adsorb on silica
Under nitrogen atmosphere, thick for 500kg marine oils is added in 1000l container.Add 5% (w/w) silica wherein, then start to stir.The Pressure Drop of container is low to moderate 40hPa.Once reach 100hPa, just container contents is heated to 70 DEG C.Keep stirring, temperature and pressure 5 hours.Then, the content in container is cooled to 40 DEG C, and successively filters on the tubular filter of the bag filter of 10 microns and 1 micron.To being filtered the Herbalox adding 2000ppm in oily half.
(C2) adsorb on silica and carbon
Under nitrogen atmosphere, thick for 500kg marine oils is added in 1000l container.Add 5% (w/w) silica wherein, then start to stir.The Pressure Drop of container is low to moderate 40hPa.Once reach 100hPa, just container contents is heated to 70 DEG C.Keep stirring, temperature and pressure 2 hours.Then, be normal by pressure setting, then add 2% active carbon.The pressure of container is made again to reach 40hPa.Keep stirring, temperature and pressure other 3 hours.Content in container is cooled to 40 DEG C, and successively filters on the tubular filter of the bag filter of 10 microns and 1 micron.To being filtered the Herbalox adding 2000ppm in oily half.
(D) adverse current deodorizing
The deodorizing of PUFA oil is made by continuous flow upstream steam distillation (CCSD).Before oil is added deodorizing tower, by oil at the temperature of 140 DEG C and 40hPa pressure under carry out in degas module degassed.After degassed, oil be preheated in a heat exchanger further the temperature of 210 DEG C, be then fed to the top of deodorizing tower.The tower of deodoriser has the internal diameter of 50mm, and is provided with structuring filling (model
rombopakS6M).In tower, the length of structuring filling is 4m.Below filler, the steam deriving from equivalent steam generating unit is added in tower continuously.The pressure of steam is about 4bar (4000hPa), and temperature is about 144 DEG C.In tower itself, maintain low-down vacuum by 3-level vacuum pump unit.At the top of tower, pressure is adjusted to 2hPa.By the counter-current flow of liquid oil phase and vapor-gas phase, from oil, take away taste component.The mass flow of oil adds up to 11kg/h, and the mass flow of steam adds up to 0.1kg/h.The oil of deodorizing is cooled to 80 DEG C, the antioxidant (tocopherol: 1000ppm that finally interpolation three kinds is different; Ascorbyl palmitate: 250ppm; Citric acid: 25ppm).
(E) application of food oil in milk (0.2%)
preparation
-sodium ascorbate is dissolved in part milk
-food oil is added in milk
-homogenizing (2 ×, under 150 and 50bar)
-milk is loaded in 200ml bottle
-pasteurization (in the core 80 DEG C at 1 minute)
-to be stored in refrigerator 2 weeks
(F) application of food oil in natural acid cheese (agitating type)
preparation
-by Milk During Heating to 30 DEG C
The mixture of-interpolation defatted milk powder, stabilizing agent and sugar
-mixing
-be heated to 65 DEG C
-add food oil
-homogenize (60 DEG C, 200kg/cm
2, 2 minutes)
-pasteurize (90 DEG C, 15 minutes)
-be cooled to 15 DEG C
-add natural acid cheese and mix
-at 45 DEG C of bottom fermentation 3-4 hour (pH4.3)
-cooling and vigorous stirring immediately
-will seal in bulk device cup
-be stored in the temperature of the highest 5 DEG C under
Sense organ is assessed:
Carry out testing as sense organ method.Sense organ test provides the most useful information, because it relates to the acceptance level of consumer to the aroma and flavor of food.The method is very responsive, and provides the information about flavor stability.
All samples to the trial test panel of undergoing training.Internal rate (according to different qualities) is adopted to carry out organoleptic parameters by descriptive analysis.Internal rate is made up of 6 intervals, 1 grade of characterization " not detectable "; 7 grades of expressions " extremely strong ".Implement variable analysis (ANOVA) to determine whether there is significant difference.Least significant difference test (L.S.D) is adopted repeatedly to compare under 5% level of signifiance.
The quality of deodorizing marine oils:
Embodiment 4
Similar with method described in embodiment 3, make the ester exchange ocean fish oil deodorizing from OceanNutrition, Canada (ONC).EE75 fish oil ethyl ester from ONC has following specification:
Outward appearance: yellow oil
Color (Lovibond red 5
1/
4"): maximum 0.5
Acid number: maximum 3.0 (mgKOH/g oil)
Peroxide number: maximum 5.0 (mEq/kg oil)
P-Anisidin value: maximum 20
EPA content: minimum 42.0%
DHA content: minimum 22.0%
N-3 fatty acid total amount: minimum 75.0%
Claims (10)
1. for the preparation of to be deodorant and by a method for stable food-grade fish oil, described method comprises: make marine oils carry out counter-current steam distillation (CCSD) in the film tower containing structuring filling, if need to add antioxidant; Wherein said counter-current steam distillation is optionally carried out under the existence of herbal extract deodorant, wherein said herbal extract deodorant is optionally rosemary and/or Sage extract, and wherein said antioxidant optionally comprises ascorbyl palmitate and/or tocopherol and optional citric acid.
2. the method for claim 1, wherein said marine oils comprises at least one PUFA (polyunsaturated fatty acid).
3. method as claimed in claim 1 or 2, wherein said marine oils is food oil containing PUFA or Arrcostab, preferred ethyl ester concentrate.
4. the method according to any one of claim 1-3, wherein said distillation at 0.1-10hPa, preferably carry out under 0.5-10hPa, low pressure more preferably at 1-5hPa.
5. by or by being deodorant of obtaining of method according to any one of claim 1-4 and by stable food-grade marine oil.
6. that be deodorant and by a stable food-grade marine oil, it is characterized in that, FAST index
tMlower than 1.5, preferred 1.3-1, more preferably 1.1-1, most preferably be 1.0.
7. marine oils as claimed in claim 6, it is characterized in that, Rancimat is greater than 6.2 hours induction period, or in the scope of 10.15-20 hour.
8. according to any one of claim 5-7 be deodorant and manufactured the purposes in meals or healthy replenishers, condensed food and feed (functional food/feed) and cosmetics or pharmaceutical preparation by stable food-grade marine oil.
9. meals, health or nutritious supplementary pharmaceutical, a kind of strengthening/functional food, a kind of cosmetics or an a kind of pharmaceutical preparation, its comprise according to any one of claim 5-8 be deodorant and by stable food-grade marine oil.
10. one kind for the method by meals, health or the nutritious supplementary pharmaceutical described in intermediate food or its component production claim 9 or strengthening/functional food, described method has following feature: the marine oils adding certain quantity of fluid form, former state, emulsion or gel form or dried forms in described intermediate food or its component, the n-3 aliphatic acid wherein containing aequum; It is made to disperse by acutely mixing; If needed, the blend obtained thus is processed further also aft-loaded airfoil and become required product.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07009539A EP1992233A1 (en) | 2007-05-11 | 2007-05-11 | Stabilized marine oils and process of making them |
| EP07009539.3 | 2007-05-11 | ||
| US79849607A | 2007-05-14 | 2007-05-14 | |
| US11/798,496 | 2007-05-14 | ||
| CN200880015614A CN101677600A (en) | 2007-05-11 | 2008-05-09 | deodorization and stabilization of marine oils |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880015614A Division CN101677600A (en) | 2007-05-11 | 2008-05-09 | deodorization and stabilization of marine oils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105029138A true CN105029138A (en) | 2015-11-11 |
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ID=39817122
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510386282.8A Pending CN105029138A (en) | 2007-05-11 | 2008-05-09 | Deodorization and stabilization of marine oils |
| CN200880015614A Pending CN101677600A (en) | 2007-05-11 | 2008-05-09 | deodorization and stabilization of marine oils |
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|---|---|---|---|
| CN200880015614A Pending CN101677600A (en) | 2007-05-11 | 2008-05-09 | deodorization and stabilization of marine oils |
Country Status (6)
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|---|---|
| EP (1) | EP2152094A2 (en) |
| JP (2) | JP5550147B2 (en) |
| KR (1) | KR101586502B1 (en) |
| CN (2) | CN105029138A (en) |
| HK (1) | HK1216977A1 (en) |
| WO (1) | WO2008138575A2 (en) |
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| CN105029138A (en) * | 2007-05-11 | 2015-11-11 | 帝斯曼知识产权资产管理有限公司 | Deodorization and stabilization of marine oils |
| CA2718525C (en) | 2008-03-17 | 2016-05-24 | Lipid Nutrition B.V. | Process for refining a triglyceride oil |
| CN102461677B (en) * | 2010-11-19 | 2014-06-18 | 嘉里特种油脂（上海）有限公司 | Composite improving stability of long-chained polyunsaturated fatty acid and application thereof |
| JP5858712B2 (en) * | 2011-09-30 | 2016-02-10 | 日清オイリオグループ株式会社 | Method for producing thin film evaporation process fats and oils |
| ES2845556T3 (en) * | 2011-11-01 | 2021-07-27 | Dsm Ip Assets Bv | Oil containing oxidatively stable polyunsaturated fatty acids |
| CN104507324A (en) * | 2012-07-31 | 2015-04-08 | 帝斯曼营养产品股份公司 | Refinement of oils using green tea extract antioxidants |
| JP6166983B2 (en) * | 2013-08-23 | 2017-07-19 | 花王株式会社 | Method for producing refined fats and oils |
| CA2930897C (en) | 2013-12-04 | 2022-08-16 | Nippon Suisan Kaisha, Ltd. | Dihomo-.gamma.-linolenic acid-containing microbial oil and dihomo-.gamma.-linolenic acid-containing microbial biomass |
| KR102600389B1 (en) * | 2015-04-27 | 2023-11-08 | 후지세유 그룹 혼샤 가부시키가이샤 | Method for producing fats and oils containing long-chain polyunsaturated fatty acids |
| CN113528235A (en) * | 2020-04-22 | 2021-10-22 | 华中农业大学 | Deodorization process for steam distillation of ethanol of edible oil |
| EP4183462A1 (en) | 2021-11-23 | 2023-05-24 | TotalEnergies OneTech | Method for deodorizing regenerated lubricating oils using supercritical co2 |
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| US3506696A (en) * | 1968-04-22 | 1970-04-14 | Procter & Gamble | Continuous high temperature steam deodorization of edible oils |
| CN1262875A (en) * | 1998-11-04 | 2000-08-16 | 弗·哈夫曼-拉罗切有限公司 | Preparation of food-level edible oil |
| US20040229233A1 (en) * | 2002-10-16 | 2004-11-18 | Ngk Insulators, Ltd. | Human housekeeping genes and human-tissue specific genes |
| CN1871331A (en) * | 2003-10-21 | 2006-11-29 | 帝斯曼知识产权资产管理有限公司 | Stabilisation of polyunsaturated fatty acid (PUFA) ester concentrates |
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| US4996072A (en) * | 1987-03-02 | 1991-02-26 | General Mills, Inc. | Physical process for the deodorization and/or cholesterol reduction of fats and oils |
| US5436018A (en) * | 1986-10-21 | 1995-07-25 | Source Food Technology, Inc. | Preparation of low cholesterol oil |
| JPS63145845U (en) * | 1987-03-17 | 1988-09-27 | ||
| US5023100A (en) * | 1988-05-02 | 1991-06-11 | Kabi Vitrum Ab | Fish oil |
| JPH0860177A (en) * | 1994-08-19 | 1996-03-05 | Ueda Seiyu Kk | Method for deodorizing oil fat or of marine animal |
| AU2001270974A1 (en) * | 2000-07-19 | 2002-01-30 | Lysi Hf | Marine oils with reduced levels of contaminants |
| US6666436B1 (en) * | 2002-09-25 | 2003-12-23 | Beco Engineering Co. | Mixed-size packed beds |
| JP4459781B2 (en) | 2004-10-29 | 2010-04-28 | 株式会社カネカ | Oils and fats containing phospholipids and processed oils and fats using phospholipids and oils |
| JP4280234B2 (en) * | 2004-12-24 | 2009-06-17 | 花王株式会社 | Production method of fats and oils high in diglycerides |
| JP4516897B2 (en) * | 2005-07-07 | 2010-08-04 | 日清オイリオグループ株式会社 | Edible oil and fat manufacturing method and edible oil and fat |
| JP5710865B2 (en) * | 2005-07-18 | 2015-04-30 | ディーエスエム アイピー アセッツ ビー．ブイ． | How to recycle old cooking oil |
| CN105029138A (en) * | 2007-05-11 | 2015-11-11 | 帝斯曼知识产权资产管理有限公司 | Deodorization and stabilization of marine oils |
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- 2008-05-09 JP JP2010506862A patent/JP5550147B2/en not_active Expired - Fee Related
- 2008-05-09 CN CN200880015614A patent/CN101677600A/en active Pending
- 2008-05-09 WO PCT/EP2008/003782 patent/WO2008138575A2/en active Application Filing
- 2008-05-09 EP EP08758456A patent/EP2152094A2/en not_active Withdrawn
- 2008-05-09 KR KR1020097023423A patent/KR101586502B1/en not_active IP Right Cessation
-
2014
- 2014-02-07 JP JP2014022494A patent/JP2014128273A/en active Pending
-
2016
- 2016-05-03 HK HK16105007.2A patent/HK1216977A1/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3506696A (en) * | 1968-04-22 | 1970-04-14 | Procter & Gamble | Continuous high temperature steam deodorization of edible oils |
| CN1262875A (en) * | 1998-11-04 | 2000-08-16 | 弗·哈夫曼-拉罗切有限公司 | Preparation of food-level edible oil |
| US20040229233A1 (en) * | 2002-10-16 | 2004-11-18 | Ngk Insulators, Ltd. | Human housekeeping genes and human-tissue specific genes |
| CN1871331A (en) * | 2003-10-21 | 2006-11-29 | 帝斯曼知识产权资产管理有限公司 | Stabilisation of polyunsaturated fatty acid (PUFA) ester concentrates |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010526896A (en) | 2010-08-05 |
| WO2008138575A2 (en) | 2008-11-20 |
| HK1216977A1 (en) | 2016-12-16 |
| KR101586502B1 (en) | 2016-01-18 |
| JP5550147B2 (en) | 2014-07-16 |
| KR20100016389A (en) | 2010-02-12 |
| EP2152094A2 (en) | 2010-02-17 |
| WO2008138575A3 (en) | 2009-01-22 |
| JP2014128273A (en) | 2014-07-10 |
| CN101677600A (en) | 2010-03-24 |
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