CN110368903A - The enrichment method of polyunsaturated fatty acid in a kind of grease - Google Patents
The enrichment method of polyunsaturated fatty acid in a kind of grease Download PDFInfo
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- CN110368903A CN110368903A CN201910495782.3A CN201910495782A CN110368903A CN 110368903 A CN110368903 A CN 110368903A CN 201910495782 A CN201910495782 A CN 201910495782A CN 110368903 A CN110368903 A CN 110368903A
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- grease
- fatty acid
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
- B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
Abstract
The invention discloses a kind of enrichment methods of polyunsaturated fatty acid in grease, comprising the following steps: 1) preparation of organometallic skeletal compound (MOF)；2) preparation of MOF particle: MOF obtained is crushed, and adhesive is then added and is granulated, MOF particle is obtained；3) in grease polyunsaturated fatty acid enrichment: MOF made from step 2 is particles filled into adsorption column, be added grease to be separated into adsorption column, adsorbent material MOF particle collected after standing, centrifugation obtains the grease of enriching polyunsaturated fatty acid；It repeats the step operation at least three times, obtains the grease of high rich polyunsaturated fatty acid.The polyunsaturated fatty acid in method enrichment grease that the present invention uses MOF to adsorb for the first time, the grease of available various enrichment degrees.The problem of mild condition of the present invention, MOF adsorbent material can reuse, and low energy consumption, and chemical agent residue is not present.
Description
Technical field
The present invention relates to a kind of enrichment methods of polyunsaturated fatty acid, and in particular to polyunsaturated fat in a kind of grease
The enrichment method of acid.
Background technique
Polyunsaturated fatty acid typically refers to a kind of fatty acid of the conjugation containing 2 or more or unconjugated double bond, main
To be present in the fat in the sources such as animals and plants and microorganism in the form of triglycerides, polyunsaturated fatty acid is considered and people
Body eubolism has important association, and has anti-inflammatory response, and anti-oxidant and reduction high-density lipoprotein etc. is specific
Physiological regulation function.
Typical polyunsaturated fatty acid can be mainly divided into n3, n6 and n9 etc. according to the position characteristics of its double bond, belong to
The linolenic acid of n3 type is one of two kinds of essential fatty acids；The DHA being added to as nutrition fortifier in baby milk powder
(docosahexaenoic acid) and ARA (eicosatetraenoic acid) adhere to n3 and n6 type separately；Common health product raw material fish oil then contains
There are n3 unsaturated fatty acid DHA and EPA (eicosapentaenoic acid).
The source of polyunsaturated fatty acid is mainly marine fishes grease, xylophyta grease and the preparation of industrial fermentation method
Microbial oil, the content of polyunsaturated fatty acid highest in part xylophyta grease (linseed oil, peony seed oil etc.)
Polyunsaturated fatty acid in 50% or so, microbial oil (such as schizochytrium limacinum algae oil, the grease etc. of Mortierella production) contains
Amount can also reach 40% or so, and the content of polyunsaturated fatty acid in other animals and plants or microbial oil is in 10-40%
Between.
Polyunsaturated fatty acid plays main physiological activity where it in grease, obtain the higher how unsaturated rouge of content
The meaning of fat acid lipid is: being supplied to the advanced method of purification such as molecular distillation with raw material, reduces advanced separating and purifying technology
Energy consumption and equipment investment improve yield；More efficient daily health products raw material is provided, the intake of daily grease is in diet
It is defined as being no more than 25 grams in guide, it is not for health that additional grease is taken in obtain polyunsaturated fatty acid
Wise, the polyunsaturated fatty acid grease after enrichment can then be reduced brings excessive grease to take in because of health care product.
It includes chemical method and physical method that the main method containing polyunsaturated fatty acid grease is enriched with from grease, with
And physical chemistry combination method.Patent 201710621797.0 and 201710667021.2, which individually discloses, utilizes urea entraing
The method of method enriching polyunsaturated fatty acid from vegetable oil, patent 201210247842.8 also disclose similar approach, make
The polyunsaturated fatty acids such as DHA of the purity 90% can be obtained with urea entraing method, but step is complex, it is also necessary to pay attention to
The residue problem of urea in product；201510757500.4 are disclosed and are enriched with from fish oil more than n3 using the enzyme process of lipase not
The method of saturated fatty acid, patent 201310161447.2 and 201210134054.8 also disclose similar method, and enzyme process is kept away
The use of chemical reagent, but the higher cost of enzyme preparation are exempted from；201510196920.X then proposing uses acetonitrile to make as solvent
With the method for the method enriching polyunsaturated fatty acid that multi-section crystallizes, the content of polyunsaturated fatty acid can be improved into 50-
90%, but product needs are handled with care and toxic acetonitrile are avoided to remain.
Summary of the invention
It is an object of the invention to overcome disadvantage of the existing technology, provide a kind of rich from grease using physical method
Collect the method for polyunsaturated fatty acid.
To achieve the goals above, the technical scheme is that in a kind of grease polyunsaturated fatty acid enrichment side
Method, which comprises the following steps:
1) preparation of organometallic skeletal compound
Metal salt and organic ligand are dissolved in solvent, 100~120 DEG C of reactions 8~for 24 hours, it filters, will consolidate after standing room temperature
Body powdered product with methanol, extract 1~6 time repeatedly by soaking, and then 50~150 DEG C of 2~12h of vacuum drying, are made organic metal bone
Frame compound (MOF)；
The solvent is formulated 1:1~3:1~2 by volume by ethyl alcohol, water and n,N dimethylformamide (DMF), institute
The molar ratio of metal salt and organic ligand is stated as 1:1~3, the mass volume ratio of the metal salt and solvent is 45~60:1 (g/
L), the volume ratio of the solid powder product and methanol is 1:1~5；
2) preparation of MOF particle
MOF obtained is crushed, adhesive is then added and is granulated, MOF particle is obtained；
3) in grease polyunsaturated fatty acid enrichment
MOF made from step 2) is particles filled into adsorption column, grease to be separated is added into adsorption column, stands 2-
Adsorbent material MOF particle is collected after 3h, centrifugation obtains the grease of enriching polyunsaturated fatty acid；Repeat the step operation at least three
It is secondary, obtain the grease of high rich polyunsaturated fatty acid.
Preferably；The metal salt is one of the corresponding nitrate of metal ion, chloride, sulfate or a variety of groups
It closes, the metal ion is Zn2+、Cu2+Or Fe2+One or more of.
Preferably；The organic ligand is to replace terephthalic acid (TPA), and the substitution terephthalic acid (TPA) is to tie shown in formula (1)
Structure,
In formula (1), R1~R4It is identical or different for group independent, indicate hydrogen atom, methyl, ethyl, propyl, hydroxyl
Methyl, ethoxy, hydroxypropyl, carboxyl, carboxymethyl or halogen；
Preferably；The organic ligand is to replace to biphenyl dicarboxylic acid, described to replace to biphenyl dicarboxylic acid for shown in formula (2)
Structure,
In formula (2), R1~R8It is identical or different for group independent, indicate hydrogen atom, methyl, ethyl, propyl, hydroxyl
Methyl, ethoxy, hydroxypropyl, carboxyl, carboxymethyl or halogen.
Preferably；The organic ligand be 2,5- dihydroxymethyl terephthalic acid (TPA), 2,5- dihydroxy butyl terephthalic acid (TPA), 2,
5- dicarboxyl terephthalic acid (TPA), 2,5- dicarboxyl methylterephthalic acid, 2- methylol, 5- carboxyl terephthalic acid (TPA), 2,2 ', 5,
5 '-tetra methylols are to biphenyl dicarboxylic acid, 2,2 ', and 5,5 '-four hydroxyl butyl are to biphenyl dicarboxylic acid, 2,2 ', and 5,5 '-tetracarboxylics are to biphenyl
Dioctyl phthalate, 2,2 ', 5,5 '-four carboxymethyl distich phthalic acids, 2,2 '-dihydroxymethyls, 5,5 '-dicarboxyls are in biphenyl dicarboxylic acid
One kind.
Preferably；MOF described in step 2) is crushed to 60~100 mesh with pulverizer, and described adhesive is that mass concentration is 1
~10% polyphosphate sodium solution.
Beneficial effects of the present invention:
(1) compared with prior art, the present invention uses Organometallic framework material (Metal-organic for the first time
Frameworks, MOFs) absorption method enrichment grease in polyunsaturated fatty acid, the oil of available various enrichment degrees
Rouge provides raw material for dietary supplements or to further molecular distillation.
In animal, plant or microbe-derived grease, fatty acid exists in the form of triglycerides, each triglycerides
Three fatty acid ends in molecule are not identical, if two of them or the above are polyunsaturated fatty acid, entire glycerol three
For ester molecule with the presence of more conjugated double bond, the cloud density of molecular orbit is also higher.
There is a large amount of three-dimensional gap, including channel-type and hole type in the structure of MOF, the size of these cellular structures can
Passed through with accommodating triglycerides molecule, designed in duct it is upper suitable replace group, such as carboxyl and hydroxyl, then the property of can choose
Interact with the fatty acid containing more conjugated double bond, this effect includes giving-feedback effect between molecular orbit, may
Carboxyl/hydroxyl and fatty acid carbonyl hydrogen bond action and charge between electrostatic interaction, can thus pass through glycerol three
Conveying of the ester in MOF is mobile, to realize that the triglycerides molecule containing more conjugated double bond is adsorbed enrichment.
(2) mild condition of the present invention, MOF adsorbent material can reuse, and comparing direct molecular distillation method, low energy consumption,
The problem of comparing urea packet and waiting chemical methods, chemical agent residue is not present.
Detailed description of the invention
Fig. 1 is the three-dimensional simulation structure chart of organometallic skeletal compound (MOF)；
Fig. 2 is the top view of Fig. 1；
Fig. 3 is the enlarged diagram of A in Fig. 2；
Fig. 4 is iron-terephthalic acid (TPA) organometallic skeletal compound XRD diffracting spectrum；
Fig. 5 is iron-terephthalic acid (TPA) organometallic skeletal compound IR map；
Fig. 6 is iron-terephthalic acid (TPA) organometallic skeletal compound BET adsorption curve figure, and embedding figure in the figure is hole
Diameter test curve figure.
Specific embodiment
In the embodiment of the present invention: schizochytrium limacinum algae oil rouge is purchased from Hubei Fuxing Biological Technology Co., Ltd.；
Mortierella alpina grease is purchased from Hubei Fuxing Biological Technology Co., Ltd.；
Korean pine seed oil rouge is purchased from Gu Yigu Food Co., Ltd, Jilin Province；
Linseed oil is purchased from the source Xilinguole League Hong Jing grease Co., Ltd；
Tunny fish oil, which is purchased from, moves lesser sage's promise (granary) Biotechnology Co., Ltd；
Krill oil is purchased from Qingdao Kang Jing marine organisms Science and Technology Ltd..
The preparation of embodiment 1:Fe-MOF74 particle
(1) by 288 grams of Fe (NO3)2.6H2O and 553 gram of 2,5- dihydroxymethyl terephthalic acid (TPA) is dissolved in 5L solvent, described
By ethyl alcohol, water and n,N dimethylformamide (DMF), 1:2:2 is formulated solvent by volume, with bubbling argon 15min, is dispelled
Then closed be placed at 100 DEG C of solution is heated for 24 hours, is cooled to room temperature by the air in solution, filtering, by solid powder product
Using methanol soak extraction 4 times repeatedly, 12h is impregnated using 5L methanol every time, then again dries solid powder product at 150 DEG C
Dry 6h, finally obtains 602.5 grams of product, is crushed to 50 mesh using pulverizer to get iron-terephthalic acid (TPA) organometallic skeletal is arrived
Compound (Fe-MOF74), pore size about 1.46nm, specific surface area 1020m2/g。
(2) 500 grams of Fe-MOF74 powder are taken, are added in swing pelletizer, it is 5% that mass concentration is slowly sprayed after unlatching
Sodium tripolyphosphate solution 100mL, after powder formed little particle after, continue spray into mass concentration be 5% sodium tripolyphosphate it is molten
Wetting shape is presented to little particle surface in liquid 50mL, then proceedes to be sprinkled into 100 grams of Fe-MOF74 powder, continues to stir 15min completion
Be granulated, obtained particle be placed in 200 DEG C of calcining 2h, obtain Fe-MOF74 particle, particle size distribution in 0.1-0.5cm, than
Surface area is in 8000-9000m2/g.The physical property of Fe-MOF74 is referring to table 1.
In the present embodiment Fe-MOF74 XRD diffracting spectrum as shown in figure 4, wherein 6 ° and 11 ° nearby be MOF feature
Peak.
The IR map of Fe-MOF74 is as shown in figure 5, wherein 3435cm-1For phenyl ring C-H stretching vibration in organic bridge；
2346cm-1For the stretching vibration of cumulated double bond；1587cm-1For the peak C=O in carboxyl；1430cm-1, 658cm-1For phenyl ring feature
Peak, 1225cm-1For C-N key peak.
The BET adsorption curve figure of Fe-MOF74 is as shown in fig. 6, the opening size test song that the embedded figure in the figure is Fe-MOF74
Line chart.
The preparation of embodiment 2:Zn-MOF74 particle
(1) by 299 grams of Zn (NO3)2.6H2O and 594 gram of 2,5- dihydroxy butyl terephthalic acid (TPA) is dissolved in 6L solvent, described
By ethyl alcohol, water and n,N dimethylformamide (DMF), 1:1:1 is formulated solvent by volume, with bubbling argon 15min, is dispelled
Air in solution, then closed be placed at 120 DEG C heats 12h, is cooled to room temperature, filtering, and solid powder product is used first
Alcohol soak extraction 2 times repeatedly impregnate 8h using 8L methanol every time, solid powder product are then dried 12h at 120 DEG C again,
704.6 grams of product are finally obtained, is crushed to 100 mesh using pulverizer to get zinc-terephthalic acid (TPA) organometallic skeletal chemical combination is arrived
Object (i.e. Zn-MOF74), pore size about 1.42nm, specific surface area 1130m2/g。
(2) 500 grams of Zn-MOF74 powder are taken, are added in swing pelletizer, it is 5% that mass concentration is slowly sprayed after unlatching
Sodium tripolyphosphate solution 150mL, after powder formed little particle after, be heated to 60 DEG C of drying 1h, then proceed to penetrating concentration be
Wetting shape is presented to little particle surface in 5% sodium tripolyphosphate solution 50mL, is then sprinkled into 100 grams of Zn-MOF74 powder, continues
It stirs 10min to complete to be granulated, obtained particle is placed in 180 DEG C of calcining 3h, obtains Zn-MOF74 particle, particle size distribution exists
0.2-0.7cm, specific surface area is in 8000-10000m2/g.The physical property of Zn-MOF74 is referring to table 1.
The physical property of table 1 Fe-MOF74 and Zn-MOF74
Embodiment 3 is enriched with DHA in schizochytrium limacinum algae oil rouge
The Fe-MOF74 particle filling for taking 500 grams of embodiments 1 to prepare is fitted into the column chromatography glass tube of diameter 60mm, then
250mL schizochytrium limacinum algae oil rouge (containing DHA 40%) slowly is added from nozzle, after filling it up with glass tube and submerging Fe-MOF74 particle,
Stand 2h, then release the grease being adsorbed, collect Fe-MOF74 adsorbent material, by adsorbent material be placed in supercentrifuge into
Row centrifugation, revolving speed 8000r/min, centrifugation time 10min collect the schizochytrium limacinum algae oil rouge 200mL of enrichment DHA, and DHA content is
50%, according to DHA content in national standard GB5009.168 test grease；It repeats enrichment procedure three times, obtains the fragmentation pot of high richness DHA
Bacterium algae grease 85mL, DHA content 75%.
Fe-MOF74 adsorbent material after centrifugation passes through acetone rinsing, and reusable after drying, the acetone of flushing subtracts
It obtains remaining grease after pressure separation to recycle together, acetone can be recycled.
Embodiment 4: the ARA in enrichment Mortierella alpina grease
The Fe-MOF74 particle filling for taking 500 grams of embodiments 1 to prepare is fitted into the column chromatography glass tube of diameter 60mm, then
250mL Mortierella alpina grease (containing ARA 40%) slowly is added from nozzle, after filling it up with glass tube and submerging Fe-MOF74 particle,
2h is stood, unadsorbed grease is then released, Fe-MOF74 adsorbent material is collected, adsorbent material is placed in supercentrifuge
It is centrifuged, revolving speed 8000r/min, centrifugation time 10min, collects Mortierella alpina grease 220mL, the ARA content of enrichment ARA
It is 45%, according to ARA content in national standard GB5009.168 test grease；It repeats enrichment procedure three times, obtains the high mountain of high richness ARA
Mortierella grease 90mL, ARA content is 70%.
Embodiment 5: the pinolenic acid in enrichment korean pine seed oil
In the column chromatography glass tube for the Fe-MOF74 granule filling people's diameter 60mm for taking 500 grams of embodiments 1 to prepare, then
300mL korean pine seed oil rouge (pinolenic acid containing 15%) slowly is added from nozzle, after filling it up with glass tube and submerging Fe-MOF74 particle,
3h is stood, unadsorbed grease is then released, Fe-MOF74 adsorbent material is collected, adsorbent material is placed in supercentrifuge
It is centrifuged, revolving speed 9000r/min, centrifugation time 10min, collects the korean pine seed oil rouge 210mL of enrichment pinolenic acid, pinolenic acid contains
Amount is 24%, according to pine tar acid content in national standard GB5009.168 test grease；It repeats enrichment procedure twice, obtains high rich pine tar
The korean pine seed oil rouge 100mL of acid, pine tar acid content are 50%.
Embodiment 6: the linolenic acid in enrichment linseed oil
In the column chromatography glass tube for the Zn-MOF74 granule filling people's diameter 60mm for taking 500 grams of embodiments 2 to prepare, then
300mL linseed oil (containing linolenic acid 55%) slowly is added from nozzle, after filling it up with glass tube and submerging Zn-MOF74 particle, stands
Then 3h releases unadsorbed grease, collect Zn-MOF74 adsorbent material, be placed in supercentrifuge and be centrifuged, revolving speed
9000r/min, centrifugation time 10min are collected and are enriched with linolenic linseed oil 220mL, linolenic acid content 70%, according to state
Mark linolenic acid content in GB5009.168 test linseed oil；It repeats enrichment procedure twice, obtains high rich linolenic linseed
Oily 92mL, linolenic acid content 85%.
Zn-MOF74 absorbing material granules after centrifugation may be reused after acetone rinsing is dried.
Embodiment 7: DHA and EPA in enrichment tunny fish oil
The Zn-MOF74 particle filling for taking 300 grams of embodiments 2 to prepare is fitted into the column chromatography glass tube of diameter 30mm, then
200mL tunny fish oil (containing DHA18% and EPA12%) slowly is added from nozzle, fills it up with glass tube and submerges Zn-MOF74 particle
Afterwards, stand 4h, then release unadsorbed grease, collect Zn-MOF74 adsorbent material, be placed in supercentrifuge carry out from
The heart, revolving speed 7000r/min, centrifugation time 15min collect the tuna grease 100mL of enrichment DHA and EPA, and DHA content is
25%, EPA content 16%, according to the DHA and EPA content in national standard GB5009.168 test tunny fish oil.
Embodiment 8: the DHA in enrichment krill oil, EPA and astaxanthin
The Zn-MOF74 particle filling for taking 500 grams of embodiments 2 to prepare is fitted into the column chromatography glass tube of diameter 60mm, then
300mL krill oil (containing DHA20%, EPA8%, astaxanthin 100ppm) slowly is added from nozzle, fills it up with glass tube and submerges Zn-
After MOF74 particle, 4h is stood, then releases unadsorbed grease, Zn-MOF74 adsorbent material is collected, as supercentrifuge
In be centrifuged, revolving speed 8000r/min, centrifugation time 15min collect enrichment DHA, and the krill oil of EPA and astaxanthin repeat rich
Collection operation twice, obtains the krill oil 80mL of high richness DHA, EPA and astaxanthin, DHA content 35%, EPA content 15%, shrimp
Green cellulose content is 280ppm.According to the DHA in national standard GB5009.168 test krill oil, EPA and content astaxanthin.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, made any to repair
Change, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (6)
1. the enrichment method of polyunsaturated fatty acid in a kind of grease, which comprises the following steps:
1) preparation of organometallic skeletal compound
Metal salt and organic ligand are dissolved in solvent, 100~120 DEG C of reactions 8~for 24 hours, it is filtered after standing room temperature, by solid powder
Last product with methanol, extract 1~6 time repeatedly by soaking, and then 50~150 DEG C of 2~12h of vacuum drying, are made organometallic skeletal
It closes object (MOF)；
The solvent is formulated 1:1~3:1~2 by volume by ethyl alcohol, water and n,N dimethylformamide (DMF), the gold
Belong to the molar ratio of salt and organic ligand for 1:1~3, the mass volume ratio of the metal salt and solvent is 45~60:1 (g/L), institute
The volume ratio for stating solid powder product and methanol is 1:1~5；
2) preparation of MOF particle
MOF obtained is crushed, adhesive is then added and is granulated, MOF particle is obtained；
3) in grease polyunsaturated fatty acid enrichment
MOF made from step 2) is particles filled into adsorption column, grease to be separated is added into adsorption column, after standing 2-3h
Adsorbent material MOF particle is collected, centrifugation obtains the grease of enriching polyunsaturated fatty acid；Repeat the step operation at least three times,
Obtain the grease of high rich polyunsaturated fatty acid.
2. the enrichment method of polyunsaturated fatty acid in grease according to claim 1, it is characterised in that: the metal salt
For one of the corresponding nitrate of metal ion, chloride, sulfate or multiple combinations, the metal ion is Zn2+、Cu2+
Or Fe2+One or more of.
3. the enrichment method of polyunsaturated fatty acid in grease according to claim 1, it is characterised in that: described organic to match
Body is to replace terephthalic acid (TPA), and the substitution terephthalic acid (TPA) is structure shown in formula (1),
In formula (1), R1~R4It is identical or different for group independent, indicate hydrogen atom, methyl, ethyl, propyl, hydroxyl first
Base, ethoxy, hydroxypropyl, carboxyl, carboxymethyl or halogen.
4. the enrichment method of polyunsaturated fatty acid in grease according to claim 1, it is characterised in that: described organic to match
Body is to replace to biphenyl dicarboxylic acid, and the substitution is structure shown in formula (2) to biphenyl dicarboxylic acid,
In formula (2), R1~R8It is identical or different for group independent, indicate hydrogen atom, methyl, ethyl, propyl, hydroxyl first
Base, ethoxy, hydroxypropyl, carboxyl, carboxymethyl or halogen.
5. the enrichment method of polyunsaturated fatty acid in grease according to claim 1 or 3, it is characterised in that: described to have
Machine ligand be 2,5- dihydroxymethyl terephthalic acid (TPA), 2,5- dihydroxy butyl terephthalic acid (TPA), 2,5- dicarboxyl terephthalic acid (TPA), 2,
5- dicarboxyl methylterephthalic acid, 2- methylol, 5- carboxyl terephthalic acid (TPA), 2,2 ', 5,5 '-tetra methylols are to biphenyl diformazan
Acid, 2,2 ', 5,5 '-four hydroxyl butyl are to biphenyl dicarboxylic acid, 2,2 ', and 5,5 '-tetracarboxylics are to biphenyl dicarboxylic acid, 2,2 ', 5,5 '-tetracarboxylic acids
Methyl is to biphenyl dicarboxylic acid, 2,2 '-dihydroxymethyls, 5,5 '-dicarboxyls to one of biphenyl dicarboxylic acid.
6. the enrichment method of polyunsaturated fatty acid in grease according to claim 1, it is characterised in that: institute in step 2)
It states MOF and is crushed to 60~100 mesh with pulverizer, described adhesive is the polyphosphate sodium solution that mass concentration is 1~10%.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108816287A (en) * | 2018-05-23 | 2018-11-16 | 福州大学 | Uio-66 immobilized Carboxyl-functional Ionic Liquid composite material and its preparation and application in situ |
| CN109046462A (en) * | 2018-08-14 | 2018-12-21 | 武汉理工大学 | A kind of Pd reduction induction compound MOF catalyst of micropore-mesopore functional form and its preparation method and application |
| CN109569728A (en) * | 2018-12-18 | 2019-04-05 | 吉林大学 | A kind of biology base metal organic frame assembles esterase catalyzed dose, preparation method and its application in biodiesel synthesis |
-
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108816287A (en) * | 2018-05-23 | 2018-11-16 | 福州大学 | Uio-66 immobilized Carboxyl-functional Ionic Liquid composite material and its preparation and application in situ |
| CN109046462A (en) * | 2018-08-14 | 2018-12-21 | 武汉理工大学 | A kind of Pd reduction induction compound MOF catalyst of micropore-mesopore functional form and its preparation method and application |
| CN109569728A (en) * | 2018-12-18 | 2019-04-05 | 吉林大学 | A kind of biology base metal organic frame assembles esterase catalyzed dose, preparation method and its application in biodiesel synthesis |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113956919A (en) * | 2021-11-15 | 2022-01-21 | 山东禹王制药有限公司 | Preparation method of high-purity unsaturated fatty acid |
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