CN110368903B - Method for enriching polyunsaturated fatty acid in grease - Google Patents
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Abstract
The invention discloses a method for enriching polyunsaturated fatty acid in grease, which comprises the following steps: 1) preparation of an organometallic framework compound (MOF); 2) preparation of MOF particles: crushing the prepared MOF, and then adding an adhesive for granulation to obtain MOF particles; 3) and (3) enriching polyunsaturated fatty acid in the grease: filling the MOF particles prepared in the step 2) into an adsorption column, adding oil to be separated into the adsorption column, standing, collecting the MOF particles of the adsorption material, and centrifuging to obtain the oil enriched with polyunsaturated fatty acids; repeating the step for at least three times to obtain the grease rich in polyunsaturated fatty acid. According to the invention, the multi-unsaturated fatty acid in the grease is enriched by adopting an MOF adsorption method for the first time, and the grease with various enrichment degrees can be obtained. The method has mild conditions, the MOF adsorption material can be recycled, the energy consumption is low, and the problem of chemical reagent residue is solved.
Description
Technical Field
The invention relates to an enrichment method of polyunsaturated fatty acid, in particular to an enrichment method of polyunsaturated fatty acid in grease.
Background
Polyunsaturated fatty acids generally refer to a class of fatty acids containing 2 or more conjugated or unconjugated double bonds, and are mainly present in fats derived from animals, plants, microorganisms, and the like in the form of triglycerides, and are considered to be important in the normal metabolism of the human body, and have specific physiological regulatory functions such as anti-inflammatory reaction, oxidation resistance, and reduction of high-density lipoproteins.
Typical polyunsaturated fatty acids can be mainly classified into n3, n6, n9 and the like according to the position characteristics of double bonds of the polyunsaturated fatty acids, and linolenic acid belonging to the n3 type is one of two essential fatty acids for human bodies; DHA (docosahexaenoic acid) and ARA (arachidonic acid) added as nutrition enhancer to infant milk powder belong to n3 and n6 types; the fish oil as a raw material of a common health-care product contains n3 unsaturated fatty acids DHA and EPA (eicosapentaenoic acid).
The polyunsaturated fatty acid is mainly from marine fish oil, woody plant oil and microbial oil prepared by industrial fermentation, the content of the polyunsaturated fatty acid in part of the woody plant oil (linseed oil, peony seed oil and the like) is about 50 percent at most, the content of the polyunsaturated fatty acid in the microbial oil (such as schizochytrium oil, oil produced by Mortierella) can also reach about 40 percent, and the content of the polyunsaturated fatty acid in other animals and plants or microbial oil is between 10 and 40 percent.
The polyunsaturated fatty acid plays a main physiological activity in the oil in which the polyunsaturated fatty acid is positioned, and the significance of obtaining the polyunsaturated fatty acid oil with higher content is as follows: the raw materials are provided for high-grade purification methods such as molecular distillation and the like, so that the energy consumption and equipment investment of high-grade separation and purification technologies are reduced, and the yield is improved; provides more efficient daily health product raw materials, the daily oil intake is regulated to be not more than 25 g in the dietary guidelines, the intake of additional oil for obtaining polyunsaturated fatty acids is not advisable for health, and the polyunsaturated fatty acid oil after enrichment can reduce the excessive oil intake caused by health products.
The main methods for enriching the oil containing polyunsaturated fatty acid from the oil comprise a chemical method, a physical method and a physical and chemical combination method. Patents 201710621797.0 and 201710667021.2 disclose methods for enriching polyunsaturated fatty acids from vegetable oils by urea embedding methods, respectively, and patent 201210247842.8 also discloses a similar method, wherein polyunsaturated fatty acids such as DHA with purity of 90% can be obtained by using the urea embedding method, but the steps are complicated, and the problem of residual urea in the product needs to be noticed; 201510757500.4 discloses a method for enriching n3 polyunsaturated fatty acids from fish oil by lipase enzyme method, and patents 201310161447.2 and 201210134054.8 also disclose similar methods, the enzyme method avoids the use of chemical reagents, but the cost of the enzyme preparation is high; 201510196920.X proposes a method for enriching polyunsaturated fatty acids by using multi-part crystallization with acetonitrile as solvent, which can increase the content of polyunsaturated fatty acids by 50-90%, but the product needs to be carefully handled to avoid toxic acetonitrile residues.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a method for enriching polyunsaturated fatty acid from grease by adopting a physical method.
In order to achieve the purpose, the technical scheme of the invention is as follows: a method for enriching polyunsaturated fatty acid in grease is characterized by comprising the following steps:
1) preparation of organometallic framework compounds
Dissolving metal salt and an organic ligand in a solvent, reacting for 8-24 h at 100-120 ℃, standing at room temperature, filtering, repeatedly soaking and extracting a solid powder product for 1-6 times by using methanol, and then drying in vacuum for 2-12 h at 50-150 ℃ to prepare an organic metal framework compound (MOF);
the solvent is prepared from ethanol, water and N, N-Dimethylformamide (DMF) according to a volume ratio of 1: 1-3: 1-2, the molar ratio of the metal salt to the organic ligand is 1: 1-3, the mass volume ratio of the metal salt to the solvent is 45-60: 1(g/L), and the volume ratio of the solid powder product to methanol is 1: 1-5;
2) preparation of MOF particles
Crushing the prepared MOF, and then adding an adhesive for granulation to obtain MOF particles;
3) enrichment of polyunsaturated fatty acids in fats and oils
Filling the MOF particles prepared in the step 2) into an adsorption column, adding oil to be separated into the adsorption column, standing for 2-3h, collecting the MOF particles of the adsorption material, and centrifuging to obtain the oil enriched with polyunsaturated fatty acids; repeating the step for at least three times to obtain the grease rich in polyunsaturated fatty acid.
Preferably; the metal salt is one or more of nitrate, chloride and sulfate corresponding to metal ions, and the metal ions are Zn2+、Cu2+Or Fe2+One or more of them.
Preferably; the organic ligand is substituted terephthalic acid which is a structure shown in a formula (1),
in the formula (1), R1～R4Are independent groups, same or different, and represent hydrogen atom, methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, carboxyl, carboxymethyl or halogen;
preferably; the organic ligand is substituted p-biphenyldicarboxylic acid which has a structure shown in a formula (2),
in the formula (2), R1～R8Are independent groups, same or different, and represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a carboxyl group, a carboxymethyl group or a halogen.
Preferably; the organic ligand is one of 2, 5-dimethylol terephthalic acid, 2, 5-dihydroxybutyl terephthalic acid, 2, 5-dicarboxyl methyl terephthalic acid, 2-hydroxymethyl, 5-carboxyl terephthalic acid, 2 ', 5, 5' -tetramethylol terephthalic acid, 2 ', 5, 5' -tetrahydroxybutyl terephthalic acid, 2 ', 5, 5' -tetracarboxyl terephthalic acid, 2 '-dimethylol and 5, 5' -dicarboxyl terephthalic acid.
Preferably; and 2) crushing the MOF to 60-100 meshes by using a crusher, wherein the adhesive is a sodium polyphosphate solution with the mass concentration of 1-10%.
The invention has the beneficial effects that:
(1) compared with the prior art, the method for enriching the polyunsaturated fatty acid in the grease by adopting the method of Metal-organic Frameworks (MOFs) adsorption for the first time can obtain the grease with various enrichment degrees, and the grease can be used for dietary supplements or provides raw materials for further molecular distillation.
In oils and fats of animal, vegetable or microbial origin, fatty acids exist in the form of triglycerides, three fatty acid terminals in each triglyceride molecule are different, and if two or more of them are polyunsaturated fatty acids, more conjugated double bonds exist in the whole triglyceride molecule, and the electron cloud density of the molecular orbital is also higher.
The MOF has a large number of three-dimensional voids, including channels and cavities, which are sized to allow the triglyceride molecules to pass through, and appropriately designed substituent groups, such as carboxyl and hydroxyl groups, in the channels can selectively interact with fatty acids with more conjugated double bonds, including feeding-feeding between molecular orbitals, possible hydrogen bonding of carboxyl/hydroxyl groups to fatty acid carbonyl groups, and electrostatic interaction between charges, so that the triglyceride molecules with more conjugated double bonds can be adsorbed and enriched by transport movement of the triglyceride in the MOF.
(2) The method has mild conditions, the MOF adsorption material can be recycled, the energy consumption is low compared with a direct molecular distillation method, and the problem of chemical reagent residue is solved compared with a urea bag and other chemical methods.
Drawings
FIG. 1 is a three-dimensional simulated structural diagram of an organometallic framework compound (MOF);
FIG. 2 is a top view of FIG. 1;
FIG. 3 is an enlarged schematic view of A in FIG. 2;
FIG. 4 is an XRD diffraction pattern of an iron-terephthalic acid organo-metallic framework compound;
FIG. 5 is an IR spectrum of an iron-terephthalic acid organometallic skeleton compound;
fig. 6 is a BET adsorption profile of an iron-terephthalic acid organometallic framework compound, in which the inset is a pore size test profile.
Detailed Description
In the embodiment of the invention: the schizochytrium limacinum grease is purchased from Hubei Fuxing Biotech limited;
mortierella alpina grease was purchased from Hubei Fuxing Biotech Co., Ltd;
red pine nut oil was purchased from Egu food Co., Ltd, Jilin province;
linseed oil is purchased from Ceylon union red well source grease Limited liability company;
tuna oil was purchased from bioscience, Inc. of san Diego, Norada;
krill oil was purchased from Qingdao kang ocean Biotech, Inc.
Example 1: preparation of Fe-MOF74 particles
(1) 288 g of Fe (NO)3)2.6H2Dissolving O and 553 g of 2, 5-dimethylolterephthalic acid in 5L of solvent, wherein the solvent is prepared by ethanol, water and N, N Dimethylformamide (DMF) according to the volume ratio of 1:2:2, bubbling for 15min by argon, removing air in the solution, then sealing the solution, heating for 24h at 100 ℃, cooling to room temperature, filtering, repeatedly soaking and extracting a solid powder product for 4 times by using methanol, soaking for 12h by using 5L of methanol each time, then drying the solid powder product for 6h at 150 ℃, finally obtaining 602.5 g of the product, and crushing to 50 meshes by using a crusher to obtain the iron-terephthalic acid organic metal framework compound (Fe-MOF74), the aperture size is about 1.46nm, and the specific surface area is 1020m2/g。
(2) Adding 500 g of Fe-MOF74 powder into a swing type granulator, slowly spraying 100mL of sodium tripolyphosphate solution with the mass concentration of 5% after the powder is started, continuously spraying 50mL of sodium tripolyphosphate solution with the mass concentration of 5% after the powder forms small particles until the surfaces of the small particles are in a wet state, then continuously spraying 100 g of Fe-MOF74 powder, continuously stirring for 15min to complete granulation, calcining the obtained particles at 200 ℃ for 2h to obtain Fe-MOF74 particles, wherein the particle size distribution is 0.1-0.5cm, and the specific surface area is 8000-2(ii) in terms of/g. The physical properties of Fe-MOF74 are shown in Table 1.
The XRD diffraction pattern of Fe-MOF74 in this example is shown in FIG. 4, wherein characteristic peaks of MOF are at around 6 ° and 11 °.
The IR spectrum of Fe-MOF74 is shown in FIG. 5, in which 3435cm-1C-H telescopic vibration of benzene ring on the organic bridge; 2346cm-1To accumulate the stretching vibration of the double bond; 1587cm-1Is the peak of C ═ O in the carboxyl group; 1430cm-1，658cm-1Is a characteristic peak of benzene ring, 1225cm-1Is the peak of C-N bond.
The BET adsorption profile of Fe-MOF74 is shown in FIG. 6, which is an inset of the pore size test profile of Fe-MOF 74.
Example 2: preparation of Zn-MOF74 particles
(1) 299 g of Zn (NO)3)2.6H2Dissolving O and 594 g of 2, 5-dihydroxybutyl terephthalic acid in 6L of solvent, wherein the solvent is prepared from ethanol, water and N, N-Dimethylformamide (DMF) according to the volume ratio of 1:1:1, bubbling for 15min with argon, removing air in the solution, sealing, heating at 120 ℃ for 12h, cooling to room temperature, filtering, repeatedly soaking and extracting a solid powder product for 2 times by using methanol, soaking 8L of methanol for 8h each time, drying the solid powder product at 120 ℃ for 12h to obtain 704.6 g of product, and crushing to 100 meshes by using a crusher to obtain the zinc-terephthalic acid organic metal framework compound (namely Zn-MOF74), wherein the pore size is about 1.42nm, and the specific surface area is 1130m2/g。
(2) Adding 500 g of Zn-MOF74 powder into a swing type granulator, slowly spraying 150mL of sodium tripolyphosphate solution with the mass concentration of 5% after the powder is started, heating to 60 ℃ to dry for 1h after the powder forms small particles, continuously spraying 50mL of sodium tripolyphosphate solution with the concentration of 5% until the surfaces of the small particles are in a wet state, then spraying 100 g of Zn-MOF74 powder, continuously stirring for 10min to complete granulation, placing the obtained particles at 180 ℃ to calcine for 3h to obtain Zn-MOF74 particles, wherein the particle size is distributed in the range of 0.2-0.7cm, and the specific surface area is 8000-2(ii) in terms of/g. Physical properties of Zn-MOF74 are shown in Table 1.
TABLE 1 physical Properties of Fe-MOF74 and Zn-MOF74
Example 3 enrichment of DHA in Schizotocytum algae oil
Filling 500 g of Fe-MOF74 particles prepared in example 1 into a glass tube with the diameter of 60mm for column chromatography, slowly adding 250mL of schizochytrium algae grease (containing 40% DHA) from a tube opening, filling the glass tube, immersing Fe-MOF74 particles, standing for 2h, discharging the adsorbed grease, collecting Fe-MOF74 adsorbing material, placing the adsorbing material in a high-speed centrifuge for centrifugation at the rotation speed of 8000r/min for 10min, collecting 200mL of DHA-enriched schizochytrium algae grease, wherein the DHA content is 50%, and testing the DHA content in the grease according to the national standard GB 5009.168; the enrichment operation is repeated for three times to obtain 85mL of high DHA-enriched schizochytrium limacinum grease with the DHA content of 75%.
And washing the centrifuged Fe-MOF74 adsorbing material with acetone, drying, and repeatedly using the washed adsorbing material, wherein the acetone for washing is subjected to reduced pressure separation to obtain residual grease which is recovered together, and the acetone can be recycled.
Example 4: ARA in mortierella alpina grease is enriched
Filling 500 g of Fe-MOF74 particles prepared in example 1 into a glass tube with the diameter of 60mm for column chromatography, slowly adding 250mL of Mortierella alpina grease (containing ARA 40%) from a tube opening, filling the glass tube, immersing Fe-MOF74 particles, standing for 2h, discharging unadsorbed grease, collecting Fe-MOF74 adsorbing material, placing the adsorbing material in a high-speed centrifuge for centrifugation at the rotation speed of 8000r/min for 10min, collecting 220mL of the Mortierella alpina grease enriched with ARA, wherein the ARA content is 45%, and testing the ARA content in the grease according to the national standard GB 5009.168; the enrichment operation is repeated for three times to obtain 90mL of mortierella alpina oil rich in ARA, wherein the ARA content is 70%.
Example 5: pine oil in enriched Korean pine seed oil
Filling 500 g of Fe-MOF74 particles prepared in example 1 into a glass tube with the diameter of 60mm for column chromatography, slowly adding 300mL of red pine nut oil (containing 15% of pinolenic acid) from a tube opening, filling the glass tube, immersing Fe-MOF74 particles, standing for 3h, discharging unadsorbed oil, collecting Fe-MOF74 adsorbing material, placing the adsorbing material in a high-speed centrifuge for centrifugation at a rotating speed of 9000r/min for 10min, collecting 210mL of red pine nut oil enriched with pinolenic acid, wherein the content of pinolenic acid is 24%, and testing the pinolenic acid content in the oil according to the national standard GB 5009.168; the enrichment operation is repeated twice, 100mL of the Korean pine seed oil rich in pinolenic acid is obtained, and the pinolenic acid content is 50%.
Example 6: linolenic acid in enriched linseed oil
Filling 500 g of Zn-MOF74 particles prepared in example 2 into a glass tube with the diameter of 60mm for column chromatography, slowly adding 300mL of linseed oil (containing linolenic acid 55%) from a tube opening, filling the glass tube and immersing Zn-MOF74 particles, standing for 3h, then discharging unadsorbed grease, collecting a Zn-MOF74 adsorption material, placing the adsorption material in a high-speed centrifuge for centrifugation at the rotating speed of 9000r/min for 10min, collecting 220mL of linolenic acid-enriched linseed oil, wherein the linolenic acid content is 70%, and testing the linolenic acid content in the linseed oil according to the national standard GB 5009.168; the enrichment operation is repeated twice, and 92mL of linseed oil with high linolenic acid content is obtained, wherein the linolenic acid content is 85%.
After being washed and dried by acetone, the centrifuged Zn-MOF74 adsorption material particles can be reused.
Example 7: enriching DHA and EPA in tuna oil
300 g of Zn-MOF74 particles prepared in example 2 are filled into a glass tube with the diameter of 30mm for column chromatography, 200mL of tuna oil (containing DHA 18% and EPA 12%) is slowly added from a tube opening, the glass tube is filled and is immersed in Zn-MOF74 particles, the mixture is kept stand for 4h, then unadsorbed grease is discharged, Zn-MOF74 adsorbing material is collected and is placed in a high-speed centrifuge for centrifugation at the rotating speed of 7000r/min for 15min, 100mL of tuna oil enriched with DHA and EPA is collected, the DHA content is 25%, the EPA content is 16%, and the DHA and EPA contents in the tuna oil are tested according to the national standard GB 5009.168.
Example 8: enriching DHA, EPA and astaxanthin in krill oil
500 g of Zn-MOF74 particles prepared in example 2 are filled into a glass tube with the diameter of 60mm for column chromatography, then 300mL of krill oil (containing DHA 20%, EPA 8% and astaxanthin 100ppm) is slowly added from a tube opening, the glass tube is filled and the Zn-MOF74 particles are immersed, the mixture is kept stand for 4h, then non-adsorbed oil is discharged, the Zn-MOF74 adsorbing material is collected, the mixture is placed in a high-speed centrifuge for centrifugation at the rotation speed of 8000r/min for 15min, the krill oil with enriched DHA, EPA and astaxanthin is collected, the enrichment operation is repeated twice, and 80mL of the krill oil with enriched DHA, EPA and astaxanthin is obtained, the DHA content is 35%, the EPA content is 15% and the astaxanthin content is 280 ppm. The krill oil was tested for DHA, EPA and astaxanthin content according to the national standard GB 5009.168.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (4)
1. A method for enriching polyunsaturated fatty acid in grease is characterized by comprising the following steps:
1) preparation of organometallic framework compounds
Dissolving metal salt and an organic ligand in a solvent, reacting for 8-24 h at 100-120 ℃, standing at room temperature, filtering, repeatedly soaking and extracting a solid powder product for 1-6 times by using methanol, and then drying in vacuum for 2-12 h at 50-150 ℃ to prepare an organic metal framework compound MOF;
the solvent is prepared from ethanol, water and N, N-dimethylformamide according to the volume ratio of 1: 1-3: 1-2, the molar ratio of the metal salt to the organic ligand is 1: 1-3, the mass volume ratio of the metal salt to the solvent is 45-60 g:1L, and the volume ratio of the solid powder product to methanol is 1: 1-5;
2) preparation of MOF particles
Crushing the prepared MOF, and then adding an adhesive for granulation to obtain MOF particles;
3) enrichment of polyunsaturated fatty acids in fats and oils
Filling the MOF particles prepared in the step 2) into an adsorption column, adding oil to be separated into the adsorption column, standing for 2-3h, collecting the MOF particles of the adsorption material, and centrifuging to obtain the oil enriched with polyunsaturated fatty acids; repeating the step for at least three times to obtain the oil rich in polyunsaturated fatty acid;
the metal salt is one or more of nitrate, chloride and sulfate corresponding to metal ions, and the metal ions are Zn2+、Cu2+Or Fe2+One or more of the above;
the organic ligand is substituted terephthalic acid which is a structure shown in a formula (1),
in the formula (1), R1～R4Are each independently a group, the same or different, and represent a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group or a carboxymethyl group.
2. The method for enriching polyunsaturated fatty acids in fats and oils according to claim 1, wherein: the organic ligand is substituted p-biphenyldicarboxylic acid which has a structure shown in a formula (2),
in the formula (2), R1～R8Are each independently a group, the same or different, and represent a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group or a carboxymethyl group.
3. The method for enriching polyunsaturated fatty acids in fats and oils according to claim 1, wherein: the organic ligand is one of 2, 5-dimethylol terephthalic acid, 2, 5-dihydroxybutyl terephthalic acid, 2, 5-dicarboxymethyl terephthalic acid, 2 ', 5, 5' -tetramethylol terephthalic acid, 2 ', 5, 5' -tetrahydroxybutyl terephthalic acid and 2,2 ', 5, 5' -tetracarboxymethyl terephthalic acid.
4. The method for enriching polyunsaturated fatty acids in fats and oils according to claim 1, wherein: and 2) crushing the MOF to 60-100 meshes by using a crusher, wherein the adhesive is a sodium polyphosphate solution with the mass concentration of 1-10%.
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