CN101940240A - Method for preparing fish oil ethyl ester microcapsule from fish pomace - Google Patents
Method for preparing fish oil ethyl ester microcapsule from fish pomace Download PDFInfo
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- 235000021323 fish oil Nutrition 0.000 title claims abstract description 176
- 125000004494 ethyl ester group Chemical group 0.000 title claims abstract description 80
- 241000251468 Actinopterygii Species 0.000 title claims abstract description 59
- 239000003094 microcapsule Substances 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000007788 liquid Substances 0.000 claims abstract description 41
- 238000000605 extraction Methods 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005913 Maltodextrin Substances 0.000 claims abstract description 13
- 229920002774 Maltodextrin Polymers 0.000 claims abstract description 13
- 102000057297 Pepsin A Human genes 0.000 claims abstract description 13
- 108090000284 Pepsin A Proteins 0.000 claims abstract description 13
- 229940035034 maltodextrin Drugs 0.000 claims abstract description 13
- 229940111202 pepsin Drugs 0.000 claims abstract description 13
- 235000010413 sodium alginate Nutrition 0.000 claims abstract description 13
- 239000000661 sodium alginate Substances 0.000 claims abstract description 13
- 229940005550 sodium alginate Drugs 0.000 claims abstract description 13
- 238000001694 spray drying Methods 0.000 claims abstract description 10
- 229920000064 Ethyl eicosapentaenoic acid Polymers 0.000 claims abstract description 3
- 238000004140 cleaning Methods 0.000 claims abstract description 3
- ITNKVODZACVXDS-YNUSHXQLSA-N ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate Chemical compound CCOC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ITNKVODZACVXDS-YNUSHXQLSA-N 0.000 claims abstract description 3
- SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 69
- 239000000463 material Substances 0.000 claims description 43
- 102000004190 Enzymes Human genes 0.000 claims description 35
- 108090000790 Enzymes Proteins 0.000 claims description 35
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- 229940088598 enzyme Drugs 0.000 claims description 35
- 239000000284 extract Substances 0.000 claims description 35
- 235000019441 ethanol Nutrition 0.000 claims description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- 210000001835 viscera Anatomy 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 17
- 238000012545 processing Methods 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- 101000693530 Staphylococcus aureus Staphylokinase Proteins 0.000 claims description 12
- 238000005119 centrifugation Methods 0.000 claims description 12
- 230000006837 decompression Effects 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- 239000012153 distilled water Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 230000015556 catabolic process Effects 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 10
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 239000002699 waste material Substances 0.000 claims description 10
- 230000018044 dehydration Effects 0.000 claims description 9
- 238000006297 dehydration reaction Methods 0.000 claims description 9
- 235000019198 oils Nutrition 0.000 claims description 9
- 239000003760 tallow Substances 0.000 claims description 8
- 239000005018 casein Substances 0.000 claims description 7
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 7
- 235000021240 caseins Nutrition 0.000 claims description 7
- 238000005516 engineering process Methods 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 239000004519 grease Substances 0.000 claims description 4
- 238000007670 refining Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 239000004365 Protease Substances 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 3
- SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 claims description 3
- 235000019419 proteases Nutrition 0.000 claims description 3
- 238000011017 operating method Methods 0.000 claims 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 18
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract description 9
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical group C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 abstract 1
- 108090000145 Bacillolysin Proteins 0.000 abstract 1
- 102000011632 Caseins Human genes 0.000 abstract 1
- 108010076119 Caseins Proteins 0.000 abstract 1
- 102000035092 Neutral proteases Human genes 0.000 abstract 1
- 108091005507 Neutral proteases Proteins 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000005360 mashing Methods 0.000 abstract 1
- 238000004806 packaging method and process Methods 0.000 abstract 1
- 229940080237 sodium caseinate Drugs 0.000 abstract 1
- 238000003860 storage Methods 0.000 abstract 1
- 230000008016 vaporization Effects 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 41
- 230000000694 effects Effects 0.000 description 21
- 238000009413 insulation Methods 0.000 description 18
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- 238000010521 absorption reaction Methods 0.000 description 10
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- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 230000036541 health Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 102000035195 Peptidases Human genes 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention relates to a method for preparing a fish oil ethyl ester microcapsule from fish pomace, which mainly comprises the extraction of fish oil, the preparation of fish fatty acid ethyl ester, the purification of fish oil ethyl ester and the preparation of a fish oil ethyl ester microcapsule, wherein the extraction of fish oil comprising the following steps: eliminating foreign matters from fish viscus, cleaning, mashing, adding pepsin and neutral protease for enzymolysis, then adding anhydrous alcohol, standing to stratify, and centrifuging to obtain the fish oil; the preparation of fish fatty acid ethyl ester comprising the following steps: mixing the fish oil with ethanol, making the mixture to be subject to an esterification reaction under the catalysis of sodium ethylate, vaporizing the ethanol, washing with water, and then centrifuging to obtain the fish oil ethyl ester; in the purification process, supercritical CO2 extraction is adopted, the purified fish oil ethyl ester is a golden yellow transparent liquid, and EPA ethyl ester and DHA ethyl ester contents thereof are more than 50%; and the preparation of a fish oil ethyl ester microcapsule comprises the following steps: mixing sodium alginate, maltodextrin and sodium caseinate, dissolving in water, adding the purified fish oil ethyl ester, and adopting a spray drying method to obtain the powdered fish oil ethyl ester microcapsule which can hide the fishy smell of the fish oil ethyl ester, improve the mouth feel and be beneficial to packaging and storage.
Description
Technical field
The invention belongs to the technical field that from the waste material of fish, reclaims grease, relate to method, and obtain refined fish oil with the method for supercritical extract with acid, alkali.Simultaneously, the present invention also relates to the preparation method of the microcapsules of refined fish oil ethyl ester.
Background technology
Fish is one of important aquatic resources of China, and its output occupies first place in the world.But many fish process only are confined to the utilization to fish body muscle, and less to the processing and utilization of fish guts, fish-bone, the first-class byproduct of fish, generally as offal treatment.The integral level of China's comprehensive utilization fish offal material is also not high, the byproduct that often contains higher protein and fat content does not obtain the rational and effective performance, this has not only caused the waste of resource, and polluted environment, so how effectively to utilize these resources, turning waste into wealth, will be a very important research topic.
Contain abundant polyunsaturated fatty acid in the marine products fish oil, its main component is EPA and DHA, and polyunsaturated fatty acid has anti-inflammatory, antithrombotic, antitumor and promote brain development, strengthen multiple physiological regulation functions such as memory.People such as Yang Yuzan utilize freeze analyse, water boiling and squeeze incorporate method of three steps and from the wall pollack fish guts, extract grease; The holy first-class people of Ping mound extracts the method for the lipid mixture of the phosphatide that contains the polyunsaturated fatty acid composition from fish guts; The eel oil extract of the quick invention of yellow-study is rich in multiple unrighted acid, the active ingredient variation, can fully reach the inhibition platelet aggregation, reduce cholesterol, effects such as prevention cardiovascular and cerebrovascular disease, existing disclosed processing method to fish by-product has: disclose during disclosed CN1432300A Chinese invention patent on the 30th application July in 2003 openly illustrates a kind of " processing and utilizing of fish offal material ", the disclosure file has disclosed the fish offal material and has been divided into internal organ and mill solution to filter out solid content be a class, all the other are another kind of, respectively through enzymolysis, with the fish oil in the modified graphite absorption recovery hydrating solution, institute is surplus be feeding and can eat (medical) hydrolysed protein soln, residue is used to make organic biofertilizer, thereby constitutes a kind of process of full processing and utilizing of fish leftovers from deep processing; That disclosed CN101248821A Chinese invention patent on the 27th application August in 2008 discloses is a kind of " enzymatic isolation method extracts the technology of fish processing fent fish oil ", and the disclosure file has introduced that the fish processing fent cleans after protease hydrolytic, water-oil separating obtain fish oil and protein hydrolysate; Fish oil is through coming unstuck, obtaining refined fish oil after depickling, decolouring and the deodorization.There is the low and low deficiency of purity of fish oil yield in the method for above-mentioned disclosed extraction fish oil.
Domestic present extraction fish oil adopts saponification method, molecularly distilled, urea adduct method, CO mostly
2Single methods such as method extract fish oil, in the shortcoming that all exists aspect purity and the oil yield separately; The fish oil that processes in the world in addition takes off the raw meat problem and also is not well solved.Therefore, how to make full use of these fish offal material, the maximum added value of therefrom extracting high-quality grease, improving fish processing, minimizing environmental pollution become current important problem.
In recent years, both at home and abroad the microencapsulation to fish oil has carried out some researchs, but have wall material price height mostly, easily go mouldy, shelf-life weak point, complex process, embedding efficiency are low, fish oil fishy smell heavily waits shortcoming.
Summary of the invention
At the defective that prior art exists, the present invention aims to provide a kind of raising fish byproduct oil yield and method for quality and goods thereof.Microcapsule product that provides fish oil ethyl ester and preparation method thereof is provided specific purposes of the present invention.
Technical solution of the present invention is: with fresh fish processing waste internal organ is raw material, and through cleaning, smash to pieces the back protease hydrolyzed, oil phase obtains refined fish oil through isoelectric point breakdown of emulsion and alcohol precipitation breakdown of emulsion, decolouring; Then refined fish oil and ethanol in the presence of pure sodium catalyst, react the fish acetoacetic ester, get the prepared fiss acetoacetic ester through supercritical extract; The fish acetoacetic ester is made fish oil micro-capsule with micro-capsule wall material again.Its concrete operations step is:
(1) extraction of fish oil
1. raw material is handled: fish processing waste internal organ, clean up, and add 1～2 times of water after the homogenate and mix.
2. extract: adopt the enzyme assisted extraction method, adding accounts for raw material and weighs 0.1～1.0% pepsin (enzyme activity 2.3 * 10 in the homogenate of fish processing waste internal organ
5U/g),, behind enzymolysis～6 hour, be transferred to pH 7 under 35～40 ℃ of conditions of temperature, add afterwards and account for raw material and weigh 0.1～1.0% neutral proteinase (enzyme activity 6 * 10 with the NaOH of 10wt% at pH 2～3
5U/g), stir while adding, temperature remains on 45～55 ℃, enzymolysis 2～6h.After enzymolysis is finished, 100 ℃ of enzyme 10min that go out;
3. isoelectric point breakdown of emulsion and alcohol precipitation breakdown of emulsion: the hydrochloric acid with 5wt% is regulated pH 5.0～5.5, adds the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 2～10h after, the centrifugal 15min of 10000r/min draws upper strata fish oil.
4. fish oil is with the activated carbon decolorizing of 0.2～5.0wt% (w/v), and centrifugation makes refined fish oil.
The gained refined fish oil both can be used as product and had directly applied to food and field of health care products in above-mentioned (one), also can be used for the preparation of further fish oil ethyl ester.
(2) preparation of fish oil ethyl ester
1. reaction: by absolute ethyl alcohol and refined fish oil is that 2～4: 1 volume ratio adds absolute ethyl alcohol and stirs in fish oil, adjusting pH with the ethanolic solution that contains 4wt%NaOH is 10, and be placed on 55～65 ℃ of stirred in water bath, under the situation that feeds nitrogen, add 3wt% solid sodium ethanol catalyst, reaction 1～6h.
2. handle: above-mentioned reactant decompression distillation is gone out excess ethyl alcohol, and being neutralized to pH with rare HCl of 1mol/L is 7, behind the standing demix, discards lower floor, oil reservoir distilled water washed twice, and the centrifuging and taking upper strata is the fish oil ethyl ester that contains multiple polyunsaturated fatty acid ethyl ester.
The gained fish oil ethyl ester both can be used as product and had directly applied to food and field of health care products in above-mentioned (two), also can be used for the preparation of further fish oil ethyl ester.
(3) fish oil ethyl ester is refining
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Fish oil second fat is put into supercritical extract equipment extraction kettle and is extracted, and uses supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 2～8wt%, 40～50 ℃ of temperature, pressure 25～35MPa, the time is 80～100min, CO
2Flow is 10～25L/h, and the temperature of separating still I is 40～50 ℃, and pressure is 8～10MPa, and the temperature of separating still II is 30～45 ℃, and pressure is 4～6MPa, and refining fish oil ethyl ester is golden transparent liquid, and wherein EPA ethyl ester and DHA ethyl ester content are greater than 50%.
Gained fish oil ethyl ester and refined fish oil ethyl ester both can be used as product and had directly applied to food and field of health care products among above-mentioned (two), (three), also can be used for the preparation of further fish oil ethyl ester microcapsules.
(4) preparation of fish oil ethyl ester microcapsules
With wall material (sodium alginate, maltodextrin, casein sodium) and the deionized water of 2.5～3.5 times of raw material gross masses mix, add the refined fish oil ethyl ester while stirring, behind 20～40MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140～200 ℃ with EAT in spray drying tower, and outlet temperature is 60～100 ℃, and the atomizing dehydration obtains Powdered fish oil ethyl ester microcapsule product.
Raw material quality per distribution ratio is:
Sodium alginate 12.0～32.0
Maltodextrin 18.0～50.0
Casein sodium 16.0～40.0
Refined fish oil 20.0～40.0
The present invention has following advantage:
1. the present invention adopts the method extraction fish oil that aqueous enzymatic method and alcohol precipitation demulsification technology combine, products obtained therefrom purity height, and quality better, oil yield increases than conventional method.
2. the present invention adopts supercritical CO
2Extraction is made with extra care fish oil ethyl ester, and the fish oil after making with extra care is golden transparent liquid, still has good flowability below zero centigrade, and wherein EPA and DHA content are greater than 50%.
3. the present invention with the micronizing of refined fish oil ethyl ester, both can shelter the fishy smell of fish oil ethyl ester by microcapsules technology, improved mouthfeel, can instant packedly deposit again, was convenient to add in food, health products, cosmetics.
4. the caseinic acid sodium molecule has amphipathicly, and very strong emulsification is arranged, and uses the wall material that contains casein sodium to prepare the fish oil ethyl ester microcapsules and can effectively prevent in the fish oil effectively nutritional labeling oxidation deterioration, and shelf life of products is prolonged greatly.
The invention will be further described below by example.
The specific embodiment
Embodiment one
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 4L water and mix, and add pepsin 4g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 2 hours under 35 ℃ and pH 2.5 conditions, added 20g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 45 ℃ of following insulation enzymolysis 6h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 3h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 0.2% (w/v), centrifugation makes refined fish oil product 180g.
Embodiment two
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 8L water and mix, and add pepsin 40g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 6 hours under 37 ℃ and pH 2 conditions, added 4g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 55 ℃ of following insulation enzymolysis 2h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 3h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 1% (w/v), centrifugation makes refined fish oil 169g.
Get the 100g refined fish oil, add the 200mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 2h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 69g contains multiple polyunsaturated fatty acid ethyl ester.
Embodiment three
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 6L water and mix, and add pepsin 15g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 2 hours under 40 ℃ and pH 3 conditions, added 25g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 55 ℃ of following insulation enzymolysis 5h, 100 ℃ of enzyme 10min that go out regulate pH to 5.5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 2h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 3% (w/v), centrifugation makes refined fish oil 191g.
Get the 100g refined fish oil, add the 250mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 2h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 72g contains multiple polyunsaturated fatty acid ethyl ester.
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Get fish tallow acid second fat 50g and put into supercritical extract equipment extraction kettle and extract, use supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 2%, 40 ℃ of temperature, pressure 25MPa, the time is 80min, CO
2Flow is 10L/h, and the temperature of separating still I is 40 ℃, and pressure is 8MPa, and the temperature of separating still II is 30 ℃, and pressure is 4MPa, can make refined fish oil ethyl ester product 22g, and product is golden transparent liquid, and wherein EPA and DHA content are greater than 50%.
Embodiment four
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 4L water and mix, and add pepsin 15g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 6 hours under 37 ℃ and pH 2.5 conditions, added 40g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 45 ℃ of following insulation enzymolysis 3h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 6h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 5% (w/v), centrifugation makes refined fish oil 200g.
Get the 100g refined fish oil, add the 300mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 5h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 76g contains multiple polyunsaturated fatty acid ethyl ester.
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Get fish tallow acid second fat 50g and put into supercritical extract equipment extraction kettle and extract, use supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 4%, 50 ℃ of temperature, pressure 30MPa, the time is 80min, CO
2Flow is 10L/h, and the temperature of separating still I is 40 ℃, and pressure is 8MPa, and the temperature of separating still II is 30 ℃, and pressure is 4MPa, can make refined fish oil ethyl ester product 19g, and product is golden transparent liquid, and wherein EPA and DHA content are greater than 50%.
Get sodium alginate 30g, maltodextrin 25g, caseinic acid 20g adds in the 300ml deionized water successively, add 24g refined fish oil ethyl ester while stirring, behind the 20MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140 ℃ with EAT in spray drying tower, outlet temperature is 60 ℃, and the atomizing dehydration obtains Powdered fish oil ethyl ester microcapsule product 106g.
Embodiment five
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 4L water and mix, and add pepsin 15g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 2 hours under 37 ℃ and pH 2.5 conditions, added 20g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 55 ℃ of following insulation enzymolysis 3h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 10h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 5% (w/v), centrifugation makes refined fish oil 206g.
Get the 100g refined fish oil, add the 400mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 1h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 64g contains multiple polyunsaturated fatty acid ethyl ester.
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Get fish tallow acid second fat 50g and put into supercritical extract equipment extraction kettle and extract, use supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 8%, 55 ℃ of temperature, pressure 35MPa, the time is 80min, CO
2Flow is 20L/h, and the temperature of separating still I is 50 ℃, and pressure is 8MPa, and the temperature of separating still II is 30 ℃, and pressure is 4MPa, can make refined fish oil ethyl ester product 21g, and product is golden transparent liquid, and wherein EPA and DHA content are greater than 50%.
Get sodium alginate 15g, maltodextrin 55g, caseinic acid 20g adds in the 300ml deionized water successively, add 24g refined fish oil ethyl ester while stirring, behind the 20MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140 ℃ with EAT in spray drying tower, outlet temperature is 60 ℃, and the atomizing dehydration obtains Powdered fish oil ethyl ester microcapsule product 118g.
Embodiment six
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 4L water and mix, and add pepsin 15g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 2 hours under 37 ℃ and pH 2.5 conditions, added 20g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 65 ℃ of following insulation enzymolysis 6h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 3h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 3% (w/v), centrifugation makes refined fish oil 212g.
Get the 100g refined fish oil, add the 230mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 4h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 71g contains multiple polyunsaturated fatty acid ethyl ester.
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Get fish tallow acid second fat 50g and put into supercritical extract equipment extraction kettle and extract, use supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 6%, 40 ℃ of temperature, pressure 25MPa, the time is 100min, CO
2Flow is 25L/h, and the temperature of separating still I is 40 ℃, and pressure is 10MPa, and the temperature of separating still II is 30 ℃, and pressure is 4MPa, can make refined fish oil ethyl ester product 23g, and product is golden transparent liquid, and wherein EPA and DHA content are greater than 50%.
Get sodium alginate 15g, maltodextrin 25g, caseinic acid 20g adds in the 300ml deionized water successively, add 30g refined fish oil ethyl ester while stirring, behind the 40MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140 ℃ with EAT in spray drying tower, outlet temperature is 60 ℃, and the atomizing dehydration obtains Powdered fish oil ethyl ester microcapsule product 100g.
Embodiment seven
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 4L water and mix, and add pepsin 15g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 2 hours under 37 ℃ and pH 2.5 conditions, added 22g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 55 ℃ of following insulation enzymolysis 3h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 3h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 2% (w/v), centrifugation makes refined fish oil 204g.
Get the 100g refined fish oil, add the 260mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 4h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 74g contains multiple polyunsaturated fatty acid ethyl ester.
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Get fish tallow acid second fat 50g and put into supercritical extract equipment extraction kettle and extract, use supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 2%, 40 ℃ of temperature, pressure 25MPa, the time is 80min, CO
2Flow is 10L/h, and the temperature of separating still I is 40 ℃, and pressure is 8MPa, and the temperature of separating still II is 45 ℃, and pressure is 4MPa, can make refined fish oil ethyl ester product 20g, and product is golden transparent liquid, and wherein EPA and DHA content are greater than 50%.
Get sodium alginate 15g, maltodextrin 25g, caseinic acid 20g adds in the 300ml deionized water successively, add 30g refined fish oil ethyl ester while stirring, behind the 20MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140 ℃ with EAT in spray drying tower, outlet temperature is 100 ℃, and the atomizing dehydration obtains Powdered fish oil ethyl ester microcapsule product 90g.
Embodiment eight
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 4L water and mix, and add pepsin 15g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 2 hours under 37 ℃ and pH 2.5 conditions, added 25g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 55 ℃ of following insulation enzymolysis 3h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 3h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 3% (w/v), centrifugation makes refined fish oil 197g.
Get the 100g refined fish oil, add the 360mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 3h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 77g contains multiple polyunsaturated fatty acid ethyl ester.
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Get fish tallow acid second fat 50g and put into supercritical extract equipment extraction kettle and extract, use supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 2%, 40 ℃ of temperature, pressure 25MPa, the time is 80min, CO
2Flow is 10L/h, and the temperature of separating still I is 40 ℃, and pressure is 8MPa, and the temperature of separating still II is 30 ℃, and pressure is 6MPa, can make refined fish oil ethyl ester product 24g, and product is golden transparent liquid, and wherein EPA and DHA content are greater than 50%.
Get sodium alginate 15g, maltodextrin 25g, caseinic acid 20g adds in the 300ml deionized water successively, add 30g refined fish oil ethyl ester while stirring, behind the 20MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 200 ℃ with EAT in spray drying tower, outlet temperature is 60 ℃, and the atomizing dehydration obtains Powdered fish oil ethyl ester microcapsule product 98g.
Embodiment nine
After the internal organ of fish remove foreign material, clean up, smash to pieces.Internal organ after getting 4kg and smashing to pieces add 4L water and mix, and add pepsin 18g (enzyme activity 2.3 * 10
5U/g), the insulation enzymolysis was transferred to pH 7 with the NaOH of 10% (w/v) after 2 hours under 37 ℃ and pH 2.5 conditions, added 20g neutral proteinase (enzyme activity 6 * 10 afterwards
5U/g), 65 ℃ of following insulation enzymolysis 6h, 100 ℃ of enzyme 10min that go out regulate pH to 5 with the hydrochloric acid of 5% (w/v), add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 3h after, the centrifugal 15min of 10000r/min, absorption upper strata fish oil.Behind the activated carbon decolorizing of fish oil with 3% (w/v), centrifugation makes refined fish oil 214g.
Get the 100g refined fish oil, add the 330mL absolute ethyl alcohol, mixing, and add the ethanolic solution that contains 4%NaOH, and transfer to pH=10, place 55 ℃ of stirred in water bath, feed nitrogen, add 3g caustic alcohol catalyst behind the question response thing mixing, reaction 6h.With above-mentioned reactant decompression distillation excess ethyl alcohol, being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, discards lower floor, uses distilled water flushing twice again, and the centrifuging and taking upper strata can make the fish oil ethyl ester product that 74g contains multiple polyunsaturated fatty acid ethyl ester.
Utilize supercritical extract equipment that the fish oil second fat of gained is made with extra care.Get fish tallow acid second fat 50g and put into supercritical extract equipment extraction kettle and extract, use supercritical CO
2Extraction, the condition of extraction fish oil is: entrainer amount of alcohol added 6%, 40 ℃ of temperature, pressure 25MPa, the time is 100min, CO
2Flow is 25L/h, and the temperature of separating still I is 40 ℃, and pressure is 10MPa, and the temperature of separating still II is 30 ℃, and pressure is 4MPa, can make refined fish oil ethyl ester product 25g, and product is golden transparent liquid, and wherein EPA and DHA content are greater than 50%.
Get sodium alginate 25g, maltodextrin 25g, caseinic acid 50g adds in the 300ml deionized water successively, add 30g refined fish oil ethyl ester while stirring, behind the 40MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140 ℃ with EAT in spray drying tower, outlet temperature is 60 ℃, and the atomizing dehydration obtains Powdered fish oil ethyl ester microcapsule product 138g.
Claims (6)
1. utilize the fish offal material to prepare the method for fish oil ethyl ester microcapsules, it is characterized in that being is raw material with the discarded internal organ of fresh fishes processing, through cleaning, smash to pieces the back protease hydrolyzed, the oil phase behind the enzymolysis obtains refined fish oil through isoelectric point breakdown of emulsion and alcohol precipitation breakdown of emulsion, decolouring; Refined fish oil and ethanol in the presence of pure sodium catalyst, react the fish acetoacetic ester, and after supercritical extract gets the prepared fiss acetoacetic ester; The prepared fiss acetoacetic ester is made the fish oil ethyl ester microcapsules with micro-capsule wall material again.
2. according to the described method of utilizing the fish offal material to prepare the fish oil ethyl ester microcapsules of claim 1, it is characterized in that described refined fish oil is to extract with following operating procedure:
(1) raw material is handled: fish processing waste internal organ, clean up, and add 1～2 times of water after smashing to pieces and mix;
(2) extract: adopt the enzyme assisted extraction method, adding accounts for raw material and weighs 0.1～1.0% pepsin in the homogenate of fish processing waste, at pH 2～3, enzymolysis is after 2～6 hours under 35～40 ℃ of conditions of temperature, be transferred to pH 7 with the NaOH of 10wt%, adding afterwards accounts for raw material and weighs 0.1～1.0% neutral proteinase, and temperature remains on 45～55 ℃, enzymolysis 2～6h, enzyme goes out;
(3) isoelectric point breakdown of emulsion and alcohol precipitation breakdown of emulsion: regulate pH to 5～5.5 with the hydrochloric acid of 5wt%, add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 2～10h after, the centrifugal 15min of 10000r/min;
(4) decolouring: fish oil is with the activated carbon decolorizing of 0.2～5.0wt%, and centrifugation gets refined fish oil.
3. according to the described method of utilizing the fish offal material to prepare the fish oil ethyl ester microcapsules of claim 1, it is characterized in that described fish tallow acid second fat is to make with following operating procedure:
(1) reaction: by absolute ethyl alcohol and fish oil is that 2～4: 1 volume ratio adds absolute ethyl alcohol and stirs in fish oil, adjusting pH with the ethanolic solution that contains 4wt%NaOH is 10, and be placed on 55～65 ℃ of stirred in water bath, feed nitrogen, add fish oil 3wt% solid sodium ethanol catalyst, reaction 1～6h;
(2) handle: above-mentioned reactant decompression distillation is gone out excess ethyl alcohol, and being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, and oil reservoir distilled water washed twice, the centrifuging and taking upper strata is a fish oil ethyl ester.
4. according to claim 1 or the 3 described methods of utilizing the fish offal material to prepare the fish oil ethyl ester microcapsules, it is characterized in that described prepared fiss acetoacetic ester is to make with following operating procedure:
The fish oil ethyl ester supercritical CO
2Extraction, extraction conditions is: the entrainer amount of alcohol added is 2～8wt% of adding fish oil ethyl ester, 40～50 ℃ of temperature, pressure 25～35MPa, the time is 80～100min, CO
2Flow is 10～25L/h, and the temperature of separating still I is 40～50 ℃, and pressure is 8～10MPa, and the temperature of separating still II is 30～45 ℃, and pressure is 46MPa, and refining fish oil ethyl ester is golden transparent liquid, and wherein EPA ethyl ester and DHA ethyl ester content are greater than 50%.
5. according to claim 1 or the 4 described methods of utilizing the fish offal material to prepare the fish oil ethyl ester microcapsules, it is characterized in that described refined fish oil second grease microcapsule is to make with following operating procedure:
Micro-capsule dry raw material quality per distribution ratio is:
Sodium alginate 12.0～32.0
Maltodextrin 18.0～50.0
Casein sodium 16.0～40.0
Refined fish oil 20.0～40.0
The water yield is pressed 2.5～3.5 water extraordinarily of dry gross mass;
Preparation technology: sodium alginate, maltodextrin and casein sodium are mixed in proportion, be dissolved in the water, add fish oil while stirring, behind 20～40MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140～200 ℃ with EAT in spray drying tower, outlet temperature is 60～100 ℃, and the atomizing dehydration obtains Powdered fish oil micro-capsule product.
6. according to each described method of utilizing the fish offal material to prepare the fish oil ethyl ester microcapsules in the claim 1～5, it is characterized in that operating procedure is:
(1) refined fish oil extracts:
(1) raw material is handled: fish processing waste internal organ, clean up, and add 1～2 times of water after smashing to pieces and mix;
(2) extract: adopt the enzyme assisted extraction method, adding accounts for raw material and weighs 0.1～1.0% pepsin in the homogenate of fish processing waste, at pH 2～3, enzymolysis is after 2～6 hours under 35～40 ℃ of conditions of temperature, be transferred to pH 7 with the NaOH of 10wt%, adding afterwards accounts for raw material and weighs 0.1～1.0% neutral proteinase, and temperature remains on 45～55 ℃, enzymolysis 2～6h, enzyme goes out;
(3) isoelectric point breakdown of emulsion and alcohol precipitation breakdown of emulsion: regulate pH to 5～5.5 with the hydrochloric acid of 5wt%, add the absolute ethyl alcohol that accounts for liquid volume 40%, leave standstill 2～10h after, the centrifugal 15min of 10000r/min;
(4) decolouring: fish oil is with the activated carbon decolorizing of 0.2～5.0wt%, and centrifugation gets refined fish oil;
(2) preparation of fish acetoacetic ester:
(1) reaction: by absolute ethyl alcohol and fish oil is that 2～4: 1 volume ratio adds absolute ethyl alcohol and stirs in fish oil, adjusting pH with the ethanolic solution that contains 4wt%NaOH is 10, and be placed on 55～65 ℃ of stirred in water bath, feed nitrogen, add fish oil 3wt% solid sodium ethanol catalyst, reaction 1～6h;
(2) handle: above-mentioned reactant decompression distillation is gone out excess ethyl alcohol, and being neutralized to pH with the HCl of 1mol/L is 7, behind the standing demix, and oil reservoir distilled water washed twice, the centrifuging and taking upper strata is a fish oil ethyl ester;
(3) the fish acetoacetic ester is refining:
The fish oil ethyl ester supercritical CO
2Extraction, extraction conditions is: the entrainer amount of alcohol added is 2～8wt% of adding fish oil ethyl ester, 40～50 ℃ of temperature, pressure 25～35MPa, the time is 80～100min, CO
2Flow is 10～25L/h, and the temperature of separating still I is 40～50 ℃, and pressure is 8～10MPa, and the temperature of separating still II is 30～45 ℃, and pressure is 46Mpa;
(4) preparation of fish acetoacetic ester microcapsules:
Micro-capsule dry raw material quality per distribution ratio is:
Sodium alginate 12.0～32.0
Maltodextrin 18.0～50.0
Casein sodium 16.0～40.0
Refined fish oil 20.0～40.0
The water yield is pressed 2.5～3.5 water extraordinarily of dry gross mass;
Preparation technology: sodium alginate, maltodextrin and casein sodium are mixed in proportion, be dissolved in the water, add fish oil while stirring, behind 20～40MPa homogeneous, form the material liquid of stable homogeneous, material liquid is 140～200 ℃ with EAT in spray drying tower, outlet temperature is 60～100 ℃, and the atomizing dehydration obtains Powdered fish oil micro-capsule product.
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