CN101525558A - Preparation process of functional polyunsaturated fatty acid in bee pollen - Google Patents
Preparation process of functional polyunsaturated fatty acid in bee pollen Download PDFInfo
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- CN101525558A CN101525558A CN200910021890A CN200910021890A CN101525558A CN 101525558 A CN101525558 A CN 101525558A CN 200910021890 A CN200910021890 A CN 200910021890A CN 200910021890 A CN200910021890 A CN 200910021890A CN 101525558 A CN101525558 A CN 101525558A
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- fatty acid
- polyunsaturated fatty
- urea
- bee pollen
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- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- 229940038481 bee pollen Drugs 0.000 title claims abstract description 32
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- 239000004202 carbamide Substances 0.000 claims abstract description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 22
- 239000000194 fatty acid Substances 0.000 claims abstract description 22
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- 239000004519 grease Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
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- 238000010992 reflux Methods 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 7
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- 238000007127 saponification reaction Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 239000006228 supernatant Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000006837 decompression Effects 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
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- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
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- 238000011049 filling Methods 0.000 claims description 2
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- WRHHVVPVKLLPFT-UHFFFAOYSA-N 2-o-ethyl 1-o-methyl oxalate Chemical compound CCOC(=O)C(=O)OC WRHHVVPVKLLPFT-UHFFFAOYSA-N 0.000 abstract 1
- 235000015097 nutrients Nutrition 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 6
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 6
- 238000000926 separation method Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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- 241000256844 Apis mellifera Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
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- 241001301148 Brassica rapa subsp. oleifera Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930003935 flavonoid Chemical class 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003516 hyperlipidaemic effect Effects 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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Landscapes
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Jellies, Jams, And Syrups (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention relates to a preparation process of functional polyunsaturated fatty acid in bee pollen, which comprises the following steps: firstly, preparing free crude fatty acid; secondly, preparing urea alcohol; thirdly, performing urea inclusion reaction; fourthly, obtaining complex fatty acid; fifthly, obtaining polyunsaturated fatty acid; and sixthly, obtaining the polyunsaturated fatty acid methyl ethyl oxalate product. The invention optimizes all parameters influencing the enrichment effect, ensures the optimal process condition, improves the yield of the polyunsaturated fatty acid, has simple process, low production cost and easy industrial popularization and application, and can realize the massive production; meanwhile, the process more completely keeps the nutrient and the physiologically active of the functional polyunsaturated fatty acid, thereby being widely applied to the development and the production of relative medicine and health product thereof.
Description
Technical field
The grease that the present invention relates in the bee pollen separates, and relates in particular to the preparation technology of functional polyunsaturated fatty acid in a kind of bee pollen.
Background technology
Bee pollen is the flour of the stamen flower pesticide of honeybee collection, contain various nutritive substances and multiple functional factors such as rich saccharide, protein, amino acid, VITAMIN, flavonoid, ester class, be called as " nutritional complete food products ", be usually used in treating prostate diseases, cardiovascular and cerebrovascular and hyperlipidaemic conditions, have the brain function of improvement, antifatigue, endocrine regulation, the anti-ageing effect of waiting for a long time.
Fat content is very high in the bee pollen, especially is rich in polyunsaturated fatty acid.According to the literature, in gas chromatogram mass spectrograph GC-MS (Gas Chromatography Mass Spectrometry) analysis revealed Brassica campestris L pollen, contain multiple unsaturated fatty acids, as linolenic acid, oleic acid, linolic acid etc., its content reaches 42.7%, 17.9%, 8.2% respectively.Unsaturated fatty acids especially polyunsaturated fatty acid is not only playing an important role aspect the 26S Proteasome Structure and Function of biometric safeguard film, and in treatment cardiovascular disorder, reducing blood-fat, prevent atherosclerosis, reduce diabetes, anti-inflammatory, anticancer and promote that aspect effect such as brain development is remarkable.
Though China's nectariferous plant cultivated area is wide, bee pollen product receipts amount is big---and on average produce per year about 3000 tons, but consume from the domestic market of bee pollen, consumption only is 1/4 of an output, and wherein major part is used for pharmacy, and small portion is used to produce protective foods and cosmetics and skincare product.Because the polyunsaturated fatty acid in bee pollen, especially its grease has multiple potential medical treatment and health care is worth, so the functional polyunsaturated fatty acid in the bee pollen has wide development and utilization prospects.
At present, the enriching and purifying polyunsaturated fatty acid adopts the crystallizing process under low temperature, supercritical extraction, molecular distillation method or adsorption method of separation etc. more.Wherein the crystallizing process under low temperature technology, principle are simple, easy to operate, but need a large amount of organic solvents, and separation purity is lower; In theory, it is feasible coming the enriching and purifying polyunsaturated fatty acid with supercritical fluid extraction, but difficulty is bigger in the actually operating, and equipment requirements is very high; Though molecular distillation method can effectively prevent the polyunsaturated fatty acid oxygenolysis of being heated, and need high-vacuum apparatus, and it is higher to consume energy; The product purity of adsorption method of separation is higher, but the separation scale is less, cost is high, is difficult to reach the requirement that large-scale industrial is produced.
Summary of the invention
The preparation technology of functional polyunsaturated fatty acid in the bee pollen that technical problem to be solved by this invention provides a kind of purity height, be produced on a large scale.
For addressing the above problem, the preparation technology of functional polyunsaturated fatty acid in the bee pollen of the present invention may further comprise the steps:
(1) preparation of free croude fatty acids: bee pollen grease is got final product after saponification, acidifying, extraction, washing, drying successively;
(2) preparation of urea alcoholic solution: urea is put into dehydrated alcohol, and heating in water bath to urea all dissolves under the nitrogen condition filling; Wherein the weightmeasurement ratio of urea and dehydrated alcohol is 1: 10～5: 10;
(3) carry out the urea clathration reaction: add croude fatty acids in the urea alcoholic solution, after the water-bath backflow, being cooled to room temperature, deepfreeze to urea inclusion crystallization is separated out, and suction filtration is collected crystallisate and filtrate respectively then; Wherein the envelope-bulk to weight ratio of urea alcoholic solution and croude fatty acids is 5: 1～15: 1;
(4) after the crystallisate that step (3) is obtained added water to fully dissolving, extraordinarily going into mass concentration by 1～2 of aqueous solution volume again was 32% the hydrochloric acid and the mixed solution of normal hexane, obtained the saturated fatty acid of complexing through extracting and separating, after concentrating the recovery normal hexane;
(5) the urea alcoholic solution that the filtrate that step (3) obtained adds 2～5 times of volumes carries out inclusion reaction again, to its gained filtrate through the decompression recycling ethanol after washing till do not have urea, supernatant liquor; The normal hexane that adds 1～2 times of volume in supernatant liquor extracts, and the reclaim under reduced pressure normal hexane gets polyunsaturated fatty acid after drying;
(6) after adding ethanol carries out the ethyl ester reaction in the polyunsaturated fatty acid that step (5) is obtained, reclaim ethanol, get polyunsaturated fatty acid ethyl ester type product after extraction, drying, wherein polyunsaturated fatty acid and alcoholic acid mass volume ratio are 1: 1～1: 4.
Bee pollen grease in the described step (1) is to adopt organic solvent extraction to obtain, or adopts supercritical CO
2Extraction obtains.
Saponification in the described step (1) is meant that adding 2～5 times of grease volumes, mass concentration in grease is 3～10% sodium hydroxide ethanolic soln, disappears through 60～70 ℃ of reflux to oil droplets.
Acidulated condition in the described step (1) is a hydrochloric acid mass concentration 5～15%, and bath temperature is 30～40 ℃.
Reflux temperature in the described step (2) is 60～75 ℃.
Water bath reflux temperature in the described step (3) is 60～70 ℃, and the low temperature crystallization temperature is-20～10 ℃.
Ethyl ester reaction in the described step (6) is meant with dense H
2SO
4Be catalyzer, fill under the nitrogen condition 65～75 ℃ of water-baths and react that wherein alcohol concn is 75～95%.
The present invention compared with prior art has the following advantages:
1, the present invention studies the process of enriching of polyunsaturated fatty acid in the bee pollen grease first, each parameter that influences concentration effect is optimized, thereby determined optimal preparation technology, belongs to domestic the first.
2, because the two keys of polyunsaturated fatty acid are more, the carbochain bending, the molecule cross section is bigger, has certain space structure, be difficult for by urea clathration, and the urea molecule that utilization of the present invention is dissolved in the organic solvent can form the hexahedron skeleton construction with hydrogen bonded between the molecule in crystallisation process, and the saturated fatty acid of straight chain contained in its framework, form more stable urea inclusion and this characteristic is separated out in crystallization, adopting repeatedly, urea adduct method carries out purification enrichment, therefore gained polyunsaturated fatty acid purity can improve the accumulation rate of polyunsaturated fatty acid up to 90%.
3,, therefore when satisfying suitability for industrialized production, reduced production cost because the present invention adopts solvent safe, reliable, inexpensive, that be easy to get.
4, do not need at high temperature to carry out owing to the present invention; and after forming, urea bag thing also can protect two keys of unsaturated fatty acids not oxidated effectively; thereby can more fully keep its nutrition and physiologically active, can be widely used in the deep development of various functional unsaturated fatty acids medicines and protective foods thereof.
5, technology of the present invention, equipment is simple, easy and simple to handle, with short production cycle, industrial consumption is few, be easy to industrial promotion and application, can accomplish scale production.
Embodiment
Embodiment 1: the preparation technology of functional polyunsaturated fatty acid in the bee pollen may further comprise the steps:
(1) preparation of free croude fatty acids:
Take by weighing 100g and obtain or adopt supercritical CO through adopting organic solvent extraction
2The bee pollen grease that extraction obtains, grease is put into flask, add 2～5 times of grease volumes, mass concentrations and be 3～10% sodium hydroxide ethanolic soln, the HH-4 type thermostat water bath that places state China Electrical Appliances Co., Ltd to produce, after 60～70 ℃ of reflux to naked eyes judge that oil droplet disappears, with the saponification liquor cool to room temperature; Add water until dissolving the saponification crystallisate fully; Add 5～15% hydrochloric acid then and carry out acidifying in 30～40 ℃ of water-baths, wherein the volume of hydrochloric acid is 2 times of aqueous solution volume that dissolve the saponification crystallisate fully; The sherwood oil or the normal hexane that add 2 times of volumes of the crystallisate aqueous solution again, adopt the separating funnel extracting and demixing, collect upper strata oily object after the layering, upper strata oily matter body and function is washed to neutrality (pH=7), and the R-114 type Rotary Evaporators concentrating under reduced pressure that adopts B ü CHI (Switzerland step fine jade laboratory technique company limited) to produce gets lipid acid after removing and desolvating; At last with anhydrous sodium sulphate to lipid acid dehydration, drying, the free croude fatty acids of 85g.
(2) preparation of urea alcoholic solution:
100g urea is put into the 2L round-bottomed flask that the 1000mL dehydrated alcohol is housed, the HH-4 type thermostat water bath that places state China Electrical Appliances Co., Ltd to produce then, fill nitrogen condition, temperature be heated under 60～75 ℃ urea all dissolving promptly get the urea alcoholic solution.
(3) carry out the urea clathration reaction:
In the Erlenmeyer flask that 400mL urea alcoholic solution is housed, add the 80g croude fatty acids, put into the HH-4 type thermostat water bath that state China Electrical Appliances Co., Ltd produces after shaking up, reflux 35～45min in 60～70 ℃ of following water-baths is as clear as crystal shape to mixture, is cooled to room temperature then; Again mixture is refrigerated to spend the night under-20～10 ℃ of low temperature and separate out,, collect crystallisate and filtrate respectively through suction filtration to the urea inclusion crystallization.
(4) get 30g crystallisate that step (3) obtains and add 120mL water to dissolving fully, extraordinarily going into mass concentration by 1～2 of aqueous solution volume again is 32% the hydrochloric acid and the mixed solution of normal hexane, after separating funnel extracting and separating organic phase, the R-114 type Rotary Evaporators concentrating under reduced pressure that adopts B ü CHI company to produce reclaims normal hexane, obtains the saturated fatty acid of 25g complexing.
(5) the urea alcoholic solution that the filtrate that step (3) is obtained adds 2～5 times of volumes carries out inclusion reaction again 1～2 time, to the R-114 type Rotary Evaporators decompression recycling ethanol of its gained merging filtrate through the production of B ü CHI company, be washed to then effluent liquid limpid till, supernatant liquor; The normal hexane that adds 1～2 times of volume in supernatant liquor adopts the separating funnel extracting and demixing, collects oil reservoir, and the R-114 type Rotary Evaporators concentrating under reduced pressure of producing through B ü CHI company reclaims solvent, gets unsaturated fatty acids; At last with anhydrous sodium sulphate to unsaturated fatty acids dewater, drying, obtain the polyunsaturated fatty acid of 42g enrichment.
(6) polyunsaturated fatty acid that enrichment obtains is stable more to be beneficial to preserve in order to make, and the 42g polyunsaturated fatty acid that step (5) is obtained adds 75～95% ethanol, and wherein polyunsaturated fatty acid and alcoholic acid mass volume ratio are 1: 1～1: 4; With dense H
2SO
4Be catalyzer, fill under the nitrogen condition after reflux 1～3 hour reacts completely to ethyl esterization 65～75 ℃ of water-baths, the R-114 type Rotary Evaporators decompression recycling ethanol of producing through B ü CHI company, polyunsaturated fatty acid ethyl ester solution; The sherwood oil that adds its 2 times of volumes then in this fatty-acid ethyl ester solution extracts, the recovery sherwood oil got the polyunsaturated fatty acid ethyl ester after branch was got the ether layer, at last with anhydrous sodium sulphate to polyunsaturated fatty acid ethyl ester dehydration, drying, obtain 51g polyunsaturated fatty acid ethyl ester type product.
Embodiment 2: the preparation technology of functional polyunsaturated fatty acid in the bee pollen may further comprise the steps:
(1) preparation of free croude fatty acids is with embodiment 1.
(2) preparation of urea alcoholic solution is with embodiment 1, wherein urea 150g, dehydrated alcohol 750mL.
(3) carry out the urea clathration reaction with embodiment 1, wherein urea alcoholic solution 800mL, croude fatty acids 60g.
(4), (5), (6) are with embodiment 1.
Embodiment 3: the preparation technology of functional polyunsaturated fatty acid in the bee pollen may further comprise the steps:
(1) preparation of free croude fatty acids is with embodiment 1.
(2) preparation of urea alcoholic solution is with embodiment 1, wherein urea 120g, dehydrated alcohol 950mL.
(3) carry out the urea clathration reaction with embodiment 1, wherein urea alcoholic solution 700mL, croude fatty acids 70g.
(4), (5), (6) are with embodiment 1.
Embodiment 4: the preparation technology of functional polyunsaturated fatty acid in the bee pollen may further comprise the steps:
(1) preparation of free croude fatty acids is with embodiment 1.
(2) preparation of urea alcoholic solution is with embodiment 1, wherein urea 80g, dehydrated alcohol 600mL.
(3) carry out the urea clathration reaction with embodiment 1, wherein urea alcoholic solution 750mL, croude fatty acids 50g.
(4), (5), (6) are with embodiment 1.
Embodiment 5: the preparation technology of functional polyunsaturated fatty acid in the bee pollen may further comprise the steps:
(1) preparation of free croude fatty acids is with embodiment 1.
(2) preparation of urea alcoholic solution is with embodiment 1, wherein urea 60g, dehydrated alcohol 550mL.
(3) carry out the urea clathration reaction with embodiment 1, wherein urea alcoholic solution 300mL, croude fatty acids 50g.
(4), (5), (6) are with embodiment 1.
Embodiment 6: the preparation technology of functional polyunsaturated fatty acid in the bee pollen may further comprise the steps:
(1) preparation of free croude fatty acids is with embodiment 1.
(2) preparation of urea alcoholic solution is with embodiment 1, wherein urea 70g, dehydrated alcohol 420mL.
(3) carry out the urea clathration reaction with embodiment 1, wherein urea alcoholic solution 600mL, croude fatty acids 75g.
(4), (5), (6) are with embodiment 1.
Claims (7)
1, the preparation technology of functional polyunsaturated fatty acid in a kind of bee pollen may further comprise the steps:
(1) preparation of free croude fatty acids: bee pollen grease is got final product after saponification, acidifying, extraction, washing, drying successively;
(2) preparation of urea alcoholic solution: urea is put into dehydrated alcohol, and heating in water bath to urea all dissolves under the nitrogen condition filling; Wherein the weightmeasurement ratio of urea and dehydrated alcohol is 1: 10～5: 10;
(3) carry out the urea clathration reaction: add croude fatty acids in the urea alcoholic solution, after the water-bath backflow, being cooled to room temperature, deepfreeze to urea inclusion crystallization is separated out, and suction filtration is collected crystallisate and filtrate respectively then; Wherein the envelope-bulk to weight ratio of urea alcoholic solution and croude fatty acids is 5: 1～15: 1;
(4) after the crystallisate that step (3) is obtained added water to fully dissolving, extraordinarily going into mass concentration by 1～2 of aqueous solution volume again was 32% the hydrochloric acid and the mixed solution of normal hexane, obtained the saturated fatty acid of complexing through extracting and separating, after concentrating the recovery normal hexane;
(5) the urea alcoholic solution that the filtrate that step (3) obtained adds 2～5 times of volumes carries out inclusion reaction again, to its gained filtrate through the decompression recycling ethanol after washing till do not have urea, supernatant liquor; The normal hexane that adds 1～2 times of volume in supernatant liquor extracts, and the reclaim under reduced pressure normal hexane gets polyunsaturated fatty acid after drying;
(6) after adding ethanol carries out the ethyl ester reaction in the polyunsaturated fatty acid that step (5) is obtained, reclaim ethanol, get polyunsaturated fatty acid ethyl ester type product after extraction, drying, wherein polyunsaturated fatty acid and alcoholic acid mass volume ratio are 1: 1～1: 4.
2, the preparation technology of functional polyunsaturated fatty acid in the bee pollen as claimed in claim 1 is characterized in that: the bee pollen grease in the described step (1) is to adopt organic solvent extraction to obtain, or adopts supercritical CO
2Extraction obtains.
3, the preparation technology of functional polyunsaturated fatty acid in the bee pollen as claimed in claim 1, it is characterized in that: the saponification in the described step (1) is meant that adding 2～5 times of grease volumes, mass concentration in grease is 3～10% sodium hydroxide ethanolic soln, disappears through 60～70 ℃ of reflux to oil droplets.
4, the preparation technology of functional polyunsaturated fatty acid in the bee pollen as claimed in claim 1, it is characterized in that: the acidulated condition in the described step (1) is a hydrochloric acid mass concentration 5～15%, bath temperature is 30～40 ℃.
5, the preparation technology of functional polyunsaturated fatty acid in the bee pollen as claimed in claim 1, it is characterized in that: the reflux temperature in the described step (2) is 60～75 ℃.
6, the preparation technology of functional polyunsaturated fatty acid in the bee pollen as claimed in claim 1, it is characterized in that: the water bath reflux temperature in the described step (3) is 60～70 ℃, the low temperature crystallization temperature is-20～10 ℃.
7, the preparation technology of functional polyunsaturated fatty acid in the bee pollen as claimed in claim 1, it is characterized in that: the ethyl ester reaction in the described step (6) is meant with dense H
2SO
4Be catalyzer, fill under the nitrogen condition 65～75 ℃ of water-baths and react that wherein alcohol concn is 75～95%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100218903A CN101525558B (en) | 2009-03-20 | 2009-03-20 | Preparation process of functional polyunsaturated fatty acid in bee pollen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100218903A CN101525558B (en) | 2009-03-20 | 2009-03-20 | Preparation process of functional polyunsaturated fatty acid in bee pollen |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102234564A (en) * | 2010-05-07 | 2011-11-09 | 上海医药工业研究院 | Extraction method of oil compounds from bee pollen |
| CN103083328A (en) * | 2011-11-04 | 2013-05-08 | 上海医药工业研究院 | Preparation method of rape bee pollen long chain fatty acids and derivatives thereof |
| CN104059774A (en) * | 2014-06-30 | 2014-09-24 | 新疆大学 | Method of preparing purslane polyunsaturated fatty acids from purslane residues |
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN105647650A (en) * | 2016-01-13 | 2016-06-08 | 常州市金坛区维格生物科技有限公司 | Method for producing freezing-resistant methyl oleate |
| CN107523424A (en) * | 2017-10-16 | 2017-12-29 | 西南林业大学 | A kind of method of amino-compound inclusion method separation unrighted acid |
| CN111164067A (en) * | 2017-08-07 | 2020-05-15 | 帝斯曼知识产权资产管理有限公司 | Process for producing concentrated polyunsaturated fatty acid oils |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100435664C (en) * | 2004-10-08 | 2008-11-26 | 颜怀玮 | Compound nutrients of hydrolyzed yeast , pollen, complete animal and plant essential fatty acid and its preparation method |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102234564A (en) * | 2010-05-07 | 2011-11-09 | 上海医药工业研究院 | Extraction method of oil compounds from bee pollen |
| CN102234564B (en) * | 2010-05-07 | 2014-07-16 | 上海医药工业研究院 | Extraction method of oil compounds from bee pollen |
| CN103083328A (en) * | 2011-11-04 | 2013-05-08 | 上海医药工业研究院 | Preparation method of rape bee pollen long chain fatty acids and derivatives thereof |
| CN103083328B (en) * | 2011-11-04 | 2015-09-30 | 上海医药工业研究院 | The preparation method of Brassica campestris L pollen long-chain fatty acid and derivant thereof |
| CN104059774A (en) * | 2014-06-30 | 2014-09-24 | 新疆大学 | Method of preparing purslane polyunsaturated fatty acids from purslane residues |
| CN104059774B (en) * | 2014-06-30 | 2016-05-11 | 新疆大学 | A kind of method of preparing purslane polyunsaturated fatty acid from purslane slag |
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN105647650A (en) * | 2016-01-13 | 2016-06-08 | 常州市金坛区维格生物科技有限公司 | Method for producing freezing-resistant methyl oleate |
| CN111164067A (en) * | 2017-08-07 | 2020-05-15 | 帝斯曼知识产权资产管理有限公司 | Process for producing concentrated polyunsaturated fatty acid oils |
| CN107523424A (en) * | 2017-10-16 | 2017-12-29 | 西南林业大学 | A kind of method of amino-compound inclusion method separation unrighted acid |
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| CN101525558B (en) | 2011-01-12 |
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