CN114195836A - Method for extracting hesperidin - Google Patents
Method for extracting hesperidin Download PDFInfo
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- CN114195836A CN114195836A CN202111561544.1A CN202111561544A CN114195836A CN 114195836 A CN114195836 A CN 114195836A CN 202111561544 A CN202111561544 A CN 202111561544A CN 114195836 A CN114195836 A CN 114195836A
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- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 title claims abstract description 126
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 title claims abstract description 126
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 title claims abstract description 126
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 title claims abstract description 126
- 229940025878 hesperidin Drugs 0.000 title claims abstract description 126
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 title claims abstract description 126
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 title claims abstract description 126
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 title claims abstract description 126
- 238000000034 method Methods 0.000 title claims abstract description 40
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 36
- 238000001035 drying Methods 0.000 claims abstract description 34
- 239000013078 crystal Substances 0.000 claims abstract description 26
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- 239000002904 solvent Substances 0.000 claims abstract description 24
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 18
- 239000007787 solid Substances 0.000 claims abstract description 15
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 239000000243 solution Substances 0.000 claims description 61
- 239000007788 liquid Substances 0.000 claims description 26
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 23
- 239000000920 calcium hydroxide Substances 0.000 claims description 23
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 23
- 239000002994 raw material Substances 0.000 claims description 20
- 230000020477 pH reduction Effects 0.000 claims description 10
- 238000003825 pressing Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
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- 239000012445 acidic reagent Substances 0.000 claims description 4
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- 239000000047 product Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
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- 230000000052 comparative effect Effects 0.000 description 11
- 239000000284 extract Substances 0.000 description 9
- 239000001509 sodium citrate Substances 0.000 description 9
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 9
- 239000011734 sodium Substances 0.000 description 8
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- 241000207199 Citrus Species 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
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- 238000004821 distillation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 3
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000012364 cultivation method Methods 0.000 description 2
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- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010047073 Vascular fragility Diseases 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
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- 210000000170 cell membrane Anatomy 0.000 description 1
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- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001989 choleretic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
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- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HXTFHSYLYXVTHC-AJHDJQPGSA-N narirutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O1 HXTFHSYLYXVTHC-AJHDJQPGSA-N 0.000 description 1
- HXTFHSYLYXVTHC-ZPHOTFPESA-N narirutin Natural products C[C@@H]1O[C@H](OC[C@H]2O[C@@H](Oc3cc(O)c4C(=O)C[C@H](Oc4c3)c5ccc(O)cc5)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O HXTFHSYLYXVTHC-ZPHOTFPESA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
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- 230000001376 precipitating effect Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A method for extracting hesperidin comprises the following steps: (1) crushing; (2) impurity removal: putting the immature bitter orange powder into an extraction tank, adding a sodium carbonate solution, stirring to remove impurities, and collecting solids; (3) washing with water; (4) extraction: putting the washed solid into an extraction tank, adding an extraction solvent, stirring, and collecting an extracting solution; (5) adjusting acid and crystallizing; (6) filtering; (7) drying the crystals to obtain the hesperidin product. The method is simple and convenient to operate, the time for removing impurities and extracting is shortened to 2.5-4.0 hours from 48 hours in the conventional method, the energy consumption is low, the productivity is doubled under the condition of not increasing plants and equipment, the operability is high, and the method is particularly suitable for industrial production.
Description
Technical Field
The invention relates to a method for extracting hesperidin, in particular to a method for extracting hesperidin with high production efficiency.
Background
Hesperidin (hesperidin) is generally extracted from physiological fruit drop immature bitter orange or citrus peel in the growth process of citrus.
In view of the seasonality of citrus fruit, fresh fruit is typically collected, sun-dried and stored. The citrus is mainly distributed in provinces such as Shanxi province, Shanguang province and the like in China, and the quality of the citrus is better in Hunan.
Hesperidin belongs to a dihydroflavonoid drug, and has the pharmacological effects that: the composition is clinically used together with vitamin C to treat various hemorrhagic diseases caused by the increase of vascular fragility. Hesperidin can excite in vitro and in frog heart. The hesperidin intravenous injection can enhance the heart contractility of the rabbit in situ, has little influence on the heart rate, and increases the blood output while enhancing the heart contractility. In addition, hesperidin has been reported to have short and obvious dilating effect on cat peripheral blood vessel, and also has antiinflammatory, antiviral, antiulcer and choleretic effects.
The existing hesperidin extraction method generally comprises the following steps: (1) crushing raw material immature bitter orange into coarse particles; (2) cooking; (3) washing with water; (4) percolating to remove impurities; (5) percolating and extracting; (6) adjusting acid; (7) filtering; (8) and (5) drying. In the prior art, the immature bitter oranges must be firstly crushed into coarse particles, because if the immature bitter oranges are not crushed into the coarse particles, the subsequent percolation impurity removal and percolation extraction cannot be carried out (solid-liquid separation is difficult, and feed liquid cannot flow out). Because of the coarse particles, the material must be boiled to destroy cell walls and cell membranes, thereby improving the percolation efficiency, and the material boiling means energy consumption such as steam. Because the particles are large, impurities can be removed only by using an impurity removal solvent with more than 40BV for impurity removal (the product content can reach more than 90 percent, and the qualified product is calculated), meanwhile, the impurities can be extracted only by using more than 45BV for percolation extraction (the extraction yield is ensured), and the discharge capacity reaches more than 100BV by adding water for boiling and washing. The time required for producing a batch of qualified hesperidin products is as long as 48-50 hours, and the production efficiency is low.
CN 106866758A discloses a process for extracting hesperidin from dried orange peel, which comprises the following steps: crushing, heat preservation and pressure maintaining, cooling, treating alkali liquor and enzyme, stirring and standing, neutralizing, redissolving, adsorbing by resin, eluting, evaporating and drying. The process needs a large amount of organic solvent during elution, has large sewage amount, complex process and long time consumption, and needs steam with high energy consumption.
CN 109180747 a discloses an extraction method of hesperidin, which comprises: grinding the raw materials into thick liquid by using alkaline water, and cleaning and removing impurities in weak alkaline water at a high temperature; adding alkaline water with pH value of 12-14, stirring at normal temperature for 1-2 hr, and filtering with plate-frame filter for solid-liquid separation to obtain extractive solution; filtering the extractive solution with ceramic membrane to obtain ultrafiltrate; adding acid into the obtained ultrafiltrate to adjust the pH value to 5-6.5, standing and precipitating for 8-10 h; and (4) washing the precipitate to be neutral, filtering, and drying and crushing a filter cake by a dryer to obtain a finished product. The method grinds the raw materials with alkaline water to easily cause the raw materials to form one-pot porridge, the raw materials cannot be kept in a granular state, when impurities are removed by warm clear water, a slurry system is pasty and very thick, in addition, the impurities are removed by natural outflow (screen filtration), the outflow speed is very slow, and the impurity removing liquid is easy to flow unclean, so that the product is unqualified; moreover, the treatment of the extracting solution needs a ceramic membrane, the temperature of the extracting solution is increased when the ceramic membrane is used for treatment, and the residue of hesperidin in the solution is increased due to the long filtering time of the ceramic membrane, so that the product yield is low; and the concentrated solution not only needs a large amount of water top and can generate a lot of sewage, but also has high energy consumption (the power of a high-pressure pump matched with a ceramic membrane with the treatment capacity of 10T/h reaches 100 kw).
CN 111362993A discloses a novel process method for extracting hesperidin, which comprises the following steps: step A, crushing immature bitter orange raw materials, wherein the crushing granularity is 40-60 meshes; b, pretreating the crushed raw materials for 3-5 hours by using a sodium citrate solution, wherein the concentration of the sodium citrate solution is controlled to be 1% -5%; c, filtering after treatment, adding the filter residue into an alkaline extracting solution, controlling the concentration to be 0.5-2.5%, and extracting for 3-6 hours; d, coarse filtering and fine filtering the alkaline extracting solution, and transferring the filtrate into a stirring tank; step E, slowly adding acid into the extraction filtrate to adjust the pH value in the stirring process, controlling the pH value to be 4.5-6.5, and waiting for 6-12 hours of crystallization; and F, passing the crystallization liquid through a plate frame, washing the filter cake with purified water until the filter cake is colorless, blow-drying the filter cake, and transferring the filter cake into a drying oven for drying at the drying temperature of 70-105 ℃. The method uses sodium citrate for removing impurities, because the extraction of hesperidin is performed by adopting alkali liquor, the hesperidin, the naringin, the isonaringin and other impurities can be simultaneously extracted, while the sodium citrate cannot theoretically remove the impurities similar to the hesperidin substance, only can remove the impurities such as colloid and the like, and the obtained product is unqualified, and has low purity and yield, long operation time and low production efficiency.
At present, the scale production of hesperidin has the problems of high difficulty, low yield, long period, difficult industrialization, thin profit after industrialization and the like.
Disclosure of Invention
The invention aims to solve the technical problem of overcoming the defects in the prior art and provide the method for extracting the hesperidin, which has the advantages of simple process, low production cost, environmental protection, energy conservation and high production efficiency and is suitable for large-scale production.
The technical scheme adopted for solving the technical problem is that the method for extracting hesperidin comprises the following steps:
(1) crushing: drying raw material immature bitter orange, crushing and sieving to obtain immature bitter orange powder;
(2) impurity removal: putting the immature bitter orange powder obtained in the step (1) into an extraction tank, adding a sodium carbonate solution, stirring to remove impurities, then carrying out solid-liquid separation, and collecting solids;
(3) washing with water: putting the solid obtained in the step (2) into an extraction tank, adding water, stirring, washing with water, then carrying out solid-liquid separation, and collecting the solid;
(4) extraction: putting the solid obtained in the step (3) into an extraction tank, adding an extraction solvent, stirring, then carrying out solid-liquid separation, and collecting an extracting solution;
(5) acid adjusting and crystallizing: adding an acidic reagent into the extracting solution obtained in the step (4) under the condition of air pressure stirring, adjusting the pH value of the extracting solution to be less than or equal to 7, standing and crystallizing to obtain an hesperidin acidification solution containing hesperidin crystals;
(6) filtering, namely filtering the acidification liquid containing the hesperidin wet crystals obtained in the step (5) by using a filtering device to obtain hesperidin wet crystals;
(7) and (3) drying: and (4) drying the hesperidin wet crystal obtained in the step (6) to obtain a hesperidin product.
Further, in the step (1), the drying is to control the water content of the immature bitter orange raw material to be 8-18%; the crushing is to crush the immature bitter orange raw material to 10-100 meshes.
Further, in the step (2), the concentration of the sodium carbonate solution is 0.2-0.5 wt%. When the concentration is too high, the hesperidin in the product can be removed, so that the yield of the hesperidin is reduced; if the concentration is too low, part of impurities in the immature bitter oranges are not completely removed, so that the product is unqualified.
In the step (2), the purpose of removing impurities by using the sodium carbonate solution is that the pH value of the sodium carbonate solution with the mass concentration of 0.2-0.5 wt% is about 10-11, the sodium carbonate solution is medium strong alkali, other acidic substances such as pectin and alkaline pectin in the immature bitter orange powder can be removed, impurities such as naringin and isocoryzanol are removed, and the hesperidin still remains in the immature bitter orange powder. However, if the sodium carbonate solution is replaced by other alkaline solutions, such as sodium citrate solution (pH value is about 8), the purpose of removing impurities sufficiently cannot be achieved, because sodium citrate can only remove alkaline pectin and pectin, and has poor effect of removing impurities such as naringin with similar properties to hesperidin.
Further, in the step (2), the adding amount of the sodium carbonate is 6-15% of the mass of the immature bitter orange powder, or the adding amount of the sodium carbonate solution is 10-30 times of the mass of the immature bitter orange powder.
Further, in the step (2), the stirring time is 1 to 3 hours.
Further, in the step (3), the washing time is 0.2-0.5 hour.
Further, in the step (3), the water used for washing is tap water.
Further, in the step (3), the amount of the added water is 10-40 times of the mass of the solid obtained in the step (2).
The purpose of the water washing in the step (3) is to remove the sodium carbonate solution and other water-soluble impurities mixed in the solid obtained in the step (2). If the water washing is insufficient, on one hand, the carbonate ions remained in the step (2) and the calcium ions in the step (4) can generate precipitates, so that the extraction difficulty is increased; on the other hand, other water-soluble impurities remained in the step (2) enter the extraction tank along with the solid, and in the extraction link of the step (4), because the extraction solvent is a mixed aqueous solution of sodium hydroxide and calcium hydroxide, the water-soluble impurities are continuously remained in the extraction solution and cannot be removed, so that the purity of the product is reduced.
Further, in the step (4), the extraction solvent is a mixed solution of water, sodium hydroxide and calcium hydroxide.
Further, in the step (4), the adding amount of the water is 15-30 times of the mass of the immature bitter oranges, the adding amount of the sodium hydroxide is 1-6% of the mass of the immature bitter oranges, and the adding amount of the calcium hydroxide is 1-10% of the mass of the immature bitter oranges.
Further, in the step (4), the extraction solvent is prepared by adding 1m of drinking water to 1.0-6.0kg of NaOH and 1.0-10.0kg of calcium hydroxide for each year; the feeding ratio of the extraction solvent is that the dosage of the extraction solvent added into every 200kg of materials is 15-30 BV.
Further, in step (4), the extraction solvent is preferably prepared from 2.0-4.0kg of NaOH + 1.5-4.0kg of calcium hydroxide and 1m of ethanol for carrying out flash cultivation.
In the step (4), the mixed solution of water, sodium hydroxide and calcium hydroxide is used as the extraction solvent, so that calcium ions are contained in the calcium hydroxide, impurities can be further subjected to calcium sealing (i.e. calcium precipitate is formed if calcium carbonate is used as an impurity), and the calcium hydroxide is cheaper than the sodium hydroxide, so that the production cost is effectively reduced from the viewpoint of large-scale production saving.
If only the sodium hydroxide aqueous solution is used, the quality of the hesperidin product is unqualified, because the calcium hydroxide has the function of further calcium-sealing impurities; if the calcium hydroxide aqueous solution is used only, the pH value of the calcium hydroxide aqueous solution is insufficient, and the hesperidin cannot be extracted completely, and if the dosage of the calcium hydroxide is increased continuously, a large amount of impurity precipitates are formed, the hesperidin is wrapped, and the hesperidin cannot react with hydroxide ions, so that the yield of the product is reduced.
The amount of the calcium hydroxide and the sodium hydroxide used in the invention is determined according to the pH value of the extracting solution, and the hesperidin reacts with the alkali to form water-soluble alkali salt, so that the water-soluble alkali salt can be dissolved in water (hesperidin precipitates can be formed again when the acid is regulated again to be weakly acidic), hydroxide ions are inevitably consumed, if the hydroxide ions in the liquid are insufficient, part of hesperidin can not react to form water-soluble products to be dissolved in the extracting solution, and the yield of the hesperidin can be influenced; if the hydroxide ions are excessive (i.e. excessive sodium hydroxide and calcium hydroxide are added), the unnecessary waste of sodium hydroxide and calcium hydroxide reagents is caused, and the difficulty of sewage treatment is increased in the subsequent wastewater treatment process.
Further, in the step (4), the stirring time is 1.0-1.5 hours.
Further, in the step (5), the acidic reagent is diluted hydrochloric acid; the pH value is 5.0-6.5.
Further, in the step (6), the filter pressure of the plate-and-frame filter pressing is more than or equal to 0.3 Mpa.
Further, in the step (7), the drying temperature is 60-80 ℃.
The principle of the invention is as follows: firstly, drying raw material immature bitter orange, crushing the dried raw material immature bitter orange into immature bitter orange powder, increasing the contact area of the immature bitter orange raw material with a sodium carbonate solution and an extraction solvent, and improving the efficiency of impurity removal and extraction; removing acidic substances, impurities with properties close to those of hesperidin and other water-soluble impurities in the immature bitter orange powder by using a sodium carbonate solution, and removing excessive sodium carbonate solution and residual water-soluble impurities by washing with water; extracting hesperidin from the washed immature bitter orange solid by using an extraction solvent (preferably a mixed solution of water, sodium hydroxide and calcium hydroxide), and finally performing acid regulation crystallization, filtration and drying to obtain the hesperidin product.
Compared with the prior art, the invention has the following beneficial effects:
(1) according to the invention, the raw material immature bitter orange is firstly crushed into powder, and hesperidin is extracted by using a crushing process, so that organic solvents such as ethanol and the like are not required, and the water consumption is reduced, thereby reducing the sewage discharge and being green and environment-friendly;
(2) according to the invention, cooking is not needed, a large amount of energy sources such as steam are saved, a plurality of hesperidin extraction pretreatment technologies are integrated and optimized only through simple steps such as crushing, impurity removal, washing and extraction, the effective extraction of hesperidin is realized, the time for impurity removal and extraction is shortened from the original 48 hours to 2.5-4.0 hours, the extraction process is greatly simplified, the time for impurity removal and extraction is shortened, the energy consumption is low, under the condition of not increasing plants and equipment, the yield is doubled, the process is simple, the operability is strong, the method is suitable for industrial production, and a new way is developed for industrialized hesperidin extraction.
Detailed Description
The present invention will be further described with reference to the following specific examples.
The chemicals used in the examples and comparative examples of the present invention were obtained from conventional commercial sources unless otherwise specified.
Example 1
The method for extracting hesperidin comprises the following steps:
(1) crushing: drying raw material fructus Aurantii Immaturus (the content of hesperidin in fructus Aurantii Immaturus is 31%) (the water content is controlled to be 10%), pulverizing and sieving (10 mesh) to obtain fructus Aurantii Immaturus powder;
(2) impurity removal: putting 200kg of immature bitter orange powder obtained in the step (1) into an extraction tank, and adding Na with the length of 5m for carrying out heavy plantation2CO3Stirring the solution to remove impurities (4.0 kg of Na each)2CO3Prepared by adding 1m for carrying out ethanol distillation for 2 hours; filtering with a plate-and-frame filter to obtain fructus Aurantii Immaturus powder;
(3) washing with water: putting the wet immature bitter orange powder obtained in the step (2) into an extraction tank, adding 2m of water for carrying out labor intensity cultivation, stirring and washing, and stirring for 0.5 hour; filtering with a plate-and-frame filter to obtain fructus Aurantii Immaturus powder washed with water to remove impurities;
(4) extraction: putting the washed immature bitter orange powder removed in the step (3) into an extraction tank, adding a 4m extraction solvent (the extraction solvent is 4m water for carrying out double-cropping cultivation, adding 8kg sodium hydroxide and 15kg calcium hydroxide), stirring and extracting for 1 hour; filtering with a plate-and-frame filter to obtain hesperidin extract;
(5) acid adjusting and crystallizing: slowly adding 6mol/L diluted HCl into the extracting solution obtained in the step (4) under the condition of air pressure stirring, adjusting the pH value of the extracting solution to 6.0, and standing for 6 hours to obtain an acidizing solution containing hesperidin crystals;
(6) filtering, and performing plate-frame filter pressing on the acidification liquid containing the hesperidin crystals obtained in the step (5), wherein the filter pressing is 0.3Mpa, so as to obtain hesperidin wet crystals;
(7) and (3) drying: and (4) placing the hesperidin wet crystal obtained in the step (6) in an oven, and drying at 70 ℃ for 12 hours to obtain 52.7kg of a hesperidin product.
Detection shows that only 3.5 hours are needed from the impurity removal to the hesperidin extract liquid obtaining in the embodiment, 11 m of water for carrying out the high-yield cultivation method is used, the hesperidin content in the obtained hesperidin product is 90.8%, and the yield is 94.5%.
Example 2
The method for extracting hesperidin comprises the following steps:
(1) crushing: drying raw material fructus Aurantii Immaturus (containing hesperidin in fructus Aurantii Immaturus at 31%) (controlling water content at 10%), pulverizing and sieving (10 mesh) to obtain fructus Aurantii Immaturus powder;
(2) impurity removal: putting 200kg of immature bitter orange powder obtained in the step (1) into an extraction tank, and adding Na for 4m high flowering2CO3The solution was stirred to remove impurities (3.0 kg of Na each)2CO3Prepared by adding 1m for carrying out ethanol year cultivation for 1.5 hours; filtering with a plate-and-frame filter to obtain fructus Aurantii Immaturus powder;
(3) washing with water: putting the impurity-removed immature bitter orange powder obtained in the step (2) into an extraction tank, adding 3m of water for carrying out stirring and washing, and stirring for 0.5 hour; filtering with a plate-and-frame filter to obtain fructus Aurantii Immaturus powder washed with water to remove impurities;
(4) extraction: putting the wet immature bitter orange powder obtained in the step (3) into an extraction tank, adding a 5m ethanol solvent (5 m ethanol, 12kg sodium hydroxide and 8kg calcium hydroxide) for carrying out ethanol extraction under stirring, and stirring for 1.5 hours; filtering with a plate-and-frame filter to obtain hesperidin extract;
(5) acid adjusting and crystallizing: slowly adding 6mol/L diluted HCl into the extracting solution obtained in the step (4) under the condition of air pressure stirring, adjusting the pH value of the extracting solution to 6.5, and standing for 6 hours to obtain hesperidin extraction acidification liquid containing hesperidin crystals;
(6) filtering, namely performing plate-frame filter pressing on the hesperidin extract acidification liquid containing the hesperidin crystals obtained in the step (5), and obtaining hesperidin wet crystals under the filter pressing pressure of 0.3 Mpa;
(7) and (3) drying: and (4) placing the hesperidin wet crystal obtained in the step (6) in an oven, and drying at 70 ℃ for 12 hours to obtain 51.6kg of hesperidin product.
Detection shows that only 3.5 hours are needed from the impurity removal to the hesperidin extract liquid obtaining in the embodiment, 12 m water for carrying out the high-yield cultivation method is used, the hesperidin content in the obtained hesperidin product is 91.2%, and the yield is 92.5%.
Example 3
The method for extracting hesperidin comprises the following steps:
(1) crushing: drying raw material fructus Aurantii Immaturus (the content of hesperidin in fructus Aurantii Immaturus is 31%) (the water content is controlled at 10%), pulverizing and sieving (10 mesh) to obtain fructus Aurantii Immaturus powder;
(2) impurity removal: putting 200kg of immature bitter orange powder obtained in the step (1) into an extraction tank, and adding Na for 4m high flowering2CO3The solution was stirred to remove impurities (2.0 kg of Na each)2CO3Prepared by adding 1m for carrying out ethanol distillation for 2 hours; filtering with a plate-and-frame filter, and shoveling to obtain fructus Aurantii Immaturus powder;
(3) washing with water: putting the impurity-removed immature bitter orange powder obtained in the step (2) into an extraction tank, adding 2.5m of water, stirring, washing and stirring for 0.5 hour; filtering with a plate-and-frame filter to obtain fructus Aurantii Immaturus powder washed with water to remove impurities;
(4) extraction: putting the washed immature bitter orange powder removed in the step (3) into an extraction tank, adding a 5m extraction solvent (the extraction solvent is 5m water for carrying out thin-wall ethanol cultivation, and 10kg sodium hydroxide and 12kg calcium hydroxide are added), stirring and extracting for 1 hour; filtering with a plate-and-frame filter to obtain hesperidin extract;
(5) acid adjusting and crystallizing: slowly adding 6mol/L diluted HCl into the extracting solution obtained in the step (4) under the condition of air pressure stirring, adjusting the pH value of the extracting solution to 6.5, and standing for 6 hours to obtain hesperidin extraction acidification liquid containing hesperidin crystals;
(6) filtering, namely performing plate-frame filter pressing on the hesperidin extract acidification liquid containing the hesperidin crystals obtained in the step (5), and obtaining hesperidin wet crystals under the filter pressing pressure of 0.3 Mpa;
(7) and (3) drying: and (4) placing the hesperidin wet crystal obtained in the step (6) in an oven, and drying at 70 ℃ for 12 hours to obtain 53.3kg of hesperidin product.
Detection shows that the method only takes 3.5 hours from impurity removal to hesperidin extraction liquid obtaining, and adopts 11.5m water for carrying out high-yield plantation, and the hesperidin content in the obtained hesperidin product is 90.8%, and the yield is 95.6%.
Comparative example 1
Comparative example 1 method for extracting hesperidin comprising the following steps:
(1) crushing: drying raw material fructus Aurantii Immaturus (the content of hesperidin in fructus Aurantii Immaturus is 31%) (the water content is controlled at 10%), pulverizing and sieving (10 mesh) to obtain fructus Aurantii Immaturus powder;
(2) impurity removal: putting 200kg of the immature bitter orange powder obtained in the step (1) into an extraction tank, adding a sodium citrate solution with the grain size of 4m, stirring and removing impurities (prepared by adding 1m of drinking water to 5.0kg of sodium citrate per year) for 5 hours; passing through a plate-and-frame filter, and shoveling to obtain impurity-removed immature bitter orange powder;
(3) washing with water: putting the impurity-removed immature bitter orange powder obtained in the step (2) into an extraction tank, adding 2.5m of water, stirring, washing and stirring for 0.5 hour; filtering with a plate-and-frame filter, and shoveling to obtain fructus Aurantii Immaturus powder;
(4) extraction: putting the wet immature bitter orange powder obtained in the step (3) into an extraction tank, adding a 5m ethanol solvent (5 m ethanol, 10kg sodium hydroxide and 12kg calcium hydroxide) for carrying out ethanol extraction under stirring, and stirring for 6 hours; filtering with a plate-and-frame filter to obtain hesperidin extract;
(5) acid adjusting and crystallizing: slowly adding 6mol/L diluted HCl into the extracting solution obtained in the step (4) under the condition of air pressure stirring, adjusting the pH value of the extracting solution to 6.5, and standing for 6 hours to obtain hesperidin extraction acidification liquid containing hesperidin crystals;
(6) crystallizing and filtering, and press-filtering the acidified solution of the extracting solution obtained in the step (5) by using a plate frame, wherein the filter pressure is 0.3Mpa, so as to obtain a hesperidin wet crystal:
(7) and (3) drying: and (4) placing the hesperidin wet crystal obtained in the step (6) in an oven, and drying at 70 ℃ for 12 hours to obtain 51.6kg of hesperidin product.
Comparative example 1 compares with example 3 with the difference that the sodium carbonate solution is exchanged for a sodium citrate solution.
Detection shows that in comparative example 1, 11.5 hours are used from impurity removal to hesperidin extract liquid obtaining, 11.5m of water is used for carrying out high speed plantation, and the hesperidin content in the obtained hesperidin product is 87.8%, so that the hesperidin product belongs to an unqualified product; the yield thereof was found to be 90.5%.
Comparative example 2
Comparative example 2 method for extracting hesperidin comprising the following steps:
(1) crushing: drying raw material fructus Aurantii Immaturus (containing hesperidin in fructus Aurantii Immaturus at 31%) (controlling water content at 10%), pulverizing and sieving (10 mesh) to obtain fructus Aurantii Immaturus powder;
(2) impurity removal: putting 200kg of immature bitter orange powder obtained in the step (1) into an extraction tank, and adding Na for 4m high flowering2CO3The solution was stirred to remove impurities (2.0 kg of Na each)2CO3Prepared by adding 1m for carrying out ethanol distillation for 2 hours; filtering with a plate-and-frame filter to obtain fructus Aurantii Immaturus powder;
(3) washing with water: putting the impurity-removed immature bitter orange powder obtained in the step (2) into an extraction tank, adding 2.5m of water, stirring, washing and stirring for 0.5 hour; passing through a plate-and-frame filter, and shoveling to obtain water-washed impurity-removed immature bitter orange powder;
(4) extraction: putting the washed immature bitter orange powder removed in the step (3) into an extraction tank, adding a 5m ethanol solvent (ethanol solvent is 5m water for carrying out thin-wall ethanol cultivation under reduced pressure, and 22kg sodium hydroxide is added), stirring and extracting for 1 hour; filtering with a plate-and-frame filter to obtain extractive solution;
(5) acid adjusting and crystallizing: slowly adding 6mol/L diluted HCl into the extracting solution obtained in the step (4) under the condition of air pressure stirring, adjusting the pH value of the extracting solution to 6.5, and standing for 6 hours to obtain an immature bitter orange extracting solution acidizing solution;
(6) crystallizing and filtering, and press-filtering the acidified solution of the extracting solution obtained in the step (5) by using a plate frame, wherein the filter pressure is 0.3Mpa, so as to obtain a hesperidin wet crystal:
(7) and (3) drying: and (4) placing the hesperidin wet crystal obtained in the step (6) in an oven, and drying at 70 ℃ for 12h to obtain 54.4kg of a hesperidin product.
Comparative example 2 is different from example 3 in that the calcium hydroxide in the extraction solvent is replaced by sodium hydroxide, i.e. the extraction solvent used in comparative example 2 is: 5m Allocation for weight reduction of water +22kg sodium hydroxide.
Detection shows that the method for carrying out heavy labor at 11.5m in comparative example 2 takes 3.5h from impurity removal to extraction liquid obtaining, but the hesperidin content in the obtained hesperidin product is 88.4%, and the product is an unqualified product; the yield thereof was found to be 91.4%. Because the content of hesperidin in the hesperidin product in the comparative example is low, part of impurities enter the hesperidin product, the yield is seemingly slightly improved, but after conversion, the total yield of the pure hesperidin product is actually lower than that of the hesperidin product prepared by the embodiment of the invention.
Claims (10)
1. A method for extracting hesperidin is characterized by comprising the following steps:
(1) crushing: drying raw material immature bitter orange, crushing and sieving to obtain immature bitter orange powder;
(2) impurity removal: putting the immature bitter orange powder obtained in the step (1) into an extraction tank, adding a sodium carbonate solution, stirring to remove impurities, then carrying out solid-liquid separation, and collecting solids;
(3) washing with water: putting the solid obtained in the step (2) into an extraction tank, adding water, stirring, washing with water, then carrying out solid-liquid separation, and collecting the solid;
(4) extraction: putting the solid obtained in the step (3) into an extraction tank, adding an extraction solvent, stirring, then carrying out solid-liquid separation, and collecting an extracting solution;
(5) acid adjusting and crystallizing: adding an acidic reagent into the extracting solution obtained in the step (4) under the condition of air pressure stirring, adjusting the pH value of the extracting solution to be less than or equal to 7, standing and crystallizing to obtain an hesperidin acidification solution containing hesperidin crystals;
(6) filtering, namely filtering the acidification liquid containing the hesperidin wet crystals obtained in the step (5) by using a filtering device to obtain hesperidin wet crystals;
(7) and (3) drying: and (4) drying the hesperidin wet crystal obtained in the step (6) to obtain a hesperidin product.
2. The method for extracting hesperidin according to claim 1, wherein in the step (1), the drying is to control the moisture content of the citrus aurantium to be 8-18%; the crushing is to crush the immature bitter orange into 10-100 meshes.
3. The method for extracting hesperidin according to claim 1 or 2, wherein in step (2), the concentration of the sodium carbonate solution is 0.2 to 0.5 wt%.
4. The method for extracting hesperidin according to any one of claims 1 to 3, wherein in the step (2), the amount of sodium carbonate added is 6 to 15% of the mass of the citrus aurantium powder, or the amount of the sodium carbonate solution added is 10 to 30 times of the mass of the citrus aurantium powder.
5. The method for extracting hesperidin according to any one of claims 1 to 4, wherein in the step (3), the amount of the added water is 10 to 40 times of the mass of the solid obtained in the step (2).
6. The method for extracting hesperidin according to any one of claims 1 to 5, wherein in the step (4), the extraction solvent is a mixed solution of water + sodium hydroxide + calcium hydroxide.
7. The method for extracting hesperidin according to claim 6, wherein in the step (4), the addition amount of water is 15-30 times of the mass of the immature bitter orange, the addition amount of sodium hydroxide is 1-6% of the mass of the immature bitter orange, and the addition amount of calcium hydroxide is 1-10% of the mass of the immature bitter orange.
8. The method for extracting hesperidin according to any one of claims 1 to 7, wherein in the step (5), the acidic reagent is diluted hydrochloric acid; the pH value is 5.0-6.5.
9. The method for extracting hesperidin according to any one of claims 1 to 8, wherein in the step (6), the filtering device is a plate-and-frame filter press; the filter pressure of plate-frame filter pressing is more than or equal to 0.3 Mpa.
10. The method for extracting hesperidin according to any one of claims 1 to 9, wherein in the step (7), the temperature of the drying is 60 to 80 ℃.
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