CN112830881A - Method for separating synephrine from hesperidin waste liquid - Google Patents
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Abstract
The invention discloses a method for separating synephrine from hesperidin waste liquid, which comprises the following steps: s1, feeding the hesperidin mother liquor onto a strong acid cation resin, eluting with water after the sample feeding is finished, eluting with a strong base mixed liquor after the water elution is finished, collecting the eluent eluted by the strong base mixed liquor, and adjusting the pH value of the eluent to 5-7 to obtain a neutralized solution; and S2, carrying out ultrafiltration on the neutralized liquid, then concentrating the neutralized liquid through a nanofiltration membrane, cooling and crystallizing the concentrated liquid, filtering and drying to obtain synephrine. The method for separating synephrine from the hesperidin waste liquid reuses the hesperidin waste liquid, extracts the poncirin from the hesperidin waste liquid, solves the problem of sewage treatment while obtaining economic benefit, and realizes waste recycling. The ion exchange is carried out through strong acid cation resin, and the elution is carried out through low-concentration strong base mixed liquor, and the strong pungent smell is avoided, the requirements on production equipment and environment are low, and the requirements on green production are met.
Description
Technical Field
The invention relates to the field of synephrine, in particular to a method for separating synephrine from hesperidin waste liquid.
Background
Over 10 billion adult overweight (body Mass index BMI) about 25kg/m2～29.9kg/m2) At least 300 million people are obese (BMIP 30 kg/m)2) In particular, the increase of morbidity and mortality of diseases such as diabetes, cardiovascular diseases, hypertension, cancer and the like is directly caused. Therefore, the treatment of obesity and hyperlipidemia attracts the attention of the global medical community, and the search for high-efficiency and low-toxicity hypolipidemic drugs, especially natural active ingredients, becomes one of the hot spots of research.
Synephrine (synephrine), also known as parahydroxyforin, sympathetic alcohol, and phenylephrine, is present in Citrus plants of the Rutaceae family, with the highest content in young fruits of Citrus aurantium (Citrus aurantium L.). Synephrine has the functions of contracting blood vessels and raising blood pressure, has strong functions of dilating trachea and bronchus, and is clinically used for treating bronchial asthma and symptoms such as hypotension, collapse, shock, orthostatic hypotension and the like in the operation and anesthesia process. Meanwhile, the health-care food also has the effects of improving metabolism, increasing calorie consumption, improving energy level, oxidizing fat and losing weight. Due to the similarity of structure and endogenous neurotransmitters and adrenaline and noradrenaline, synephrine has been widely used in the health care product industries such as medicine, food, beverage and the like.
Hesperidin belongs to vitamin P class medicine, and is used for enhancing toughness of capillary vessel. Methyl hesperidin, a derivative of hesperidin, is also a vitamin P drug, and is a variety collected in Japan food additive official book. Is a medicine for treating hypertension and myocardial infarction, is used as a raw material for pharmacy in the medical industry, and is one of the main components of Chinese patent medicine Maitong. With increasing production factories of hesperidin in China, the mother liquor obtained after the hesperidin is extracted has complex components, high COD content and difficult sewage treatment, and the hesperidin mother liquor rich in synephrine is not effectively developed and utilized, thereby causing the waste of resources.
The citrus peel residue is taken from patent application No. 201410647518.4, and is extracted by ethanol water solution to obtain a crude synephrine extract: extracting the crude synephrine extract with ethyl acetate, performing column chromatography by using HP20 resin, eluting with 10-20% ethanol water solution to remove impurities, and intensively washing the synephrine with 50-70% ethanol water solution; adjusting the pH value of the 50-70% ethanol eluent by hydrochloric acid to 2.5-4.5, extracting by ethyl acetate, and then carrying out rotary evaporation to remove the ethyl acetate; dissolving with water with pH 6-8, adjusting the pH to 6-8 with sodium hydroxide, then loading the solution onto an XAD18 chromatographic column, eluting impurities with water after loading the column, eluting synephrine with 5-20% ethanol water solution, and collecting the eluent step by step.
Disclosure of Invention
The invention provides a method for separating synephrine from hesperidin waste liquid, which aims to solve the technical problems of complex composition of mother liquid after hesperidin extraction, high COD content, difficult sewage treatment, and resource waste caused by the fact that the hesperidin mother liquid is rich in synephrine and is not effectively developed and utilized.
The technical scheme adopted by the invention is as follows:
a method for separating synephrine from hesperidin waste liquid comprises the following steps:
s1, feeding the hesperidin mother liquor onto a strong acid cation resin, eluting with water after the sample feeding is finished, eluting with a strong base mixed liquor after the water elution is finished, collecting the eluent eluted by the strong base mixed liquor, and adjusting the pH value of the eluent to 5-7 to obtain a neutralized solution;
and S2, carrying out ultrafiltration on the neutralized liquid, then concentrating the neutralized liquid through a nanofiltration membrane, cooling and crystallizing the concentrated liquid, filtering and drying to obtain synephrine.
Further, as the strongly acidic cation resin, a C100E strongly acidic cation resin was used.
Further, the strong alkali mixed solution comprises 0.05 to 0.5 mass percent of KOH, 0.05 to 1 mass percent of NaOH or 0.05 to 0.5 mass percent of Ca (OH)2At least two kinds of mixed solution of (1).
Further, the strong base mixed solution comprises a mixed solution of 0.1% by mass of NaOH and 0.3% by mass of KOH; or the alkali mixed solution comprises 0.4 percent of NaOH and 0.1 percent of Ca (OH)2The mixed solution of (1); or the alkali mixed solution comprises 0.2 percent of Ca (OH)2And a mixed solution of 0.1% by mass of KOH.
Further, the volume of the strong alkali mixed solution is 3 BV-4 BV, and the flow rate of the strong alkali mixed solution is 1.5 BV/h-4 BV/h.
Further, the sampling speed of the hesperidin mother liquor is 6 BV/h-15 BV/h, the volume of water elution is 3 BV-4 BV, and the speed of water elution is 1.5 BV/h-4 BV/h.
Further, in step S2, a ceramic membrane of 50nm to 500nm is used for ultrafiltration.
Furthermore, the nanofiltration membrane in the step S2 is a nanofiltration membrane of 100 Da-1000 Da.
Further, the concentrated solution in the step S2 is stirred at the temperature of 5-15 ℃, is kept stand for crystallization for 10-48 h, is filtered by a plate-and-frame filter and is dried to obtain synephrine.
Further, in step S1, hydrochloric acid with a concentration of 10% to 30% is used to adjust the pH of the eluate.
The invention has the following beneficial effects:
the method for separating synephrine from the hesperidin waste liquid reuses the hesperidin waste liquid, extracts the poncirin from the hesperidin waste liquid, solves the problem of sewage treatment while obtaining economic benefit, and realizes waste recycling.
The method for separating synephrine from the hesperidin waste liquid comprises the steps of carrying out ion exchange by using strong acid cation resin, eluting by using low-concentration strong base mixed liquid, forming salt by using the synephrine under the strong base condition, adjusting the pH value of an eluent to 5-7 after elution so as to reduce the synephrine back to a free state, and is controllable in operation method, free of strong pungent smell, low in production equipment and environmental requirements and capable of meeting the requirement of green production.
The method for separating synephrine from the hesperidin waste liquid adopts an ultrafiltration method to remove synephrine impurities, and has the advantages of physical treatment, low energy consumption and no organic solvent residue. The nanofiltration membrane is adopted for synephrine concentration, physical treatment is realized, energy consumption is low, chemical structure change is prevented, water and monovalent salt ions pass through the nanofiltration membrane, so that the effects of desalination and concentration are achieved, synephrine is further purified, and the synephrine recovery rate is improved.
In addition to the objects, features and advantages described above, other objects, features and advantages of the present invention are also provided. The present invention will be described in further detail below with reference to the accompanying drawings.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this application, illustrate embodiments of the invention and, together with the description, serve to explain the invention and not to limit the invention. In the drawings:
FIG. 1 is a liquid chromatogram of a synephrine standard of the present invention, where 8.239 is the synephrine peak; and
FIG. 2 is a liquid chromatogram of synephrine of preferred embodiment 1 of the present invention, where 8.295 is the synephrine peak.
Detailed Description
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail below with reference to the embodiments with reference to the attached drawings.
FIG. 1 is a liquid chromatogram of a synephrine standard of the present invention, where 8.239 is the synephrine peak; FIG. 2 is a liquid chromatogram of synephrine of preferred embodiment 1 of the present invention, where 8.295 is the synephrine peak.
The method for separating synephrine from hesperidin waste liquid in the embodiment comprises the following steps:
s1, feeding the hesperidin mother liquor onto a strong acid cation resin, eluting with water after the sample feeding is finished, eluting with a strong base mixed liquor after the water elution is finished, collecting the eluent eluted by the strong base mixed liquor, and adjusting the pH value of the eluent to 5-7 to obtain a neutralized solution;
and S2, carrying out ultrafiltration on the neutralized liquid, then concentrating the neutralized liquid through a nanofiltration membrane, cooling and crystallizing the concentrated liquid, filtering and drying to obtain synephrine.
The method for separating synephrine from the hesperidin waste liquid reuses the hesperidin waste liquid, extracts the poncirin from the hesperidin waste liquid, solves the problem of sewage treatment while obtaining economic benefit, and realizes waste recycling.
The method for separating synephrine from the hesperidin waste liquid comprises the steps of carrying out ion exchange by using strong acid cation resin, eluting by using low-concentration strong base mixed liquid, forming salt by using the synephrine under the strong base condition, adjusting the pH value of an eluent to 5-7 after elution so as to reduce the synephrine back to a free state, and is controllable in operation method, free of strong pungent smell, low in production equipment and environmental requirements and capable of meeting the requirement of green production.
The method for separating synephrine from the hesperidin waste liquid adopts an ultrafiltration method to remove synephrine impurities, and has the advantages of physical treatment, low energy consumption and no organic solvent residue. The nanofiltration membrane is adopted for synephrine concentration, physical treatment is realized, energy consumption is low, chemical structure change is prevented, water and monovalent salt ions pass through the nanofiltration membrane, so that the effects of desalination and concentration are achieved, synephrine is further purified, and the synephrine recovery rate is improved.
In the process of preparing hesperidin, after a hesperidin raw material is extracted by alkaline water, the pH is adjusted to be neutral, a hesperidin crystal is separated out, the hesperidin crystal is obtained after filter pressing, a filtrate is a hesperidin mother liquor which can also be called as hesperidin waste liquor, and the hesperidin waste liquor is directly discharged as sewage under normal conditions.
In this example, the strongly acidic cation resin was a C100E strong acidA cationic resin. Synephrine is enriched by macroporous resin, alcohol is usually used as eluent, but the macroporous resin basically cannot adsorb the synephrine and has poor adsorption effect on the synephrine, so that the macroporous resin applied to adsorbing the synephrine is gradually replaced. The cation exchange resin adsorbs synephrine onto strong acid cation resin, and if ammonia water is used for elution, the cation exchange resin elutes the synephrine along with the ammonia water through ion exchange. Ammonia water is also called Amonian water, and its main ingredient is NH3·H2O, an aqueous solution of ammonia, colorless and transparent and having an offensive odor. The ammonia gas is toxic, irritating and corrosive to eyes, nose and skin, and can suffocate people with a maximum allowable concentration of 30mg/m in air3And the neutralization reaction with acid generates heat, so that the danger of combustion and explosion exists. The production equipment and the environment have high requirements, and the industrial production is difficult. Pretreating a strong-acid cation resin column for adsorbing synephrine, soaking the column for 2 hours by using a sodium chloride solution with the mass fraction of 10%, loading the column, backwashing by using distilled water until effluent water is clear, washing by using a 50g/L sodium hydroxide solution with the volume of 2 times of the column volume, washing by using distilled water until the pH value is neutral, washing by using a hydrochloric acid solution with the volume fraction of 4 times of the column volume of 5%, and finally washing by using distilled water until the pH value is neutral.
In this embodiment, the alkali mixture comprises 0.05-0.5% by weight of KOH, 0.05-1% by weight of NaOH, or 0.05-0.5% by weight of Ca (OH)2At least two kinds of mixed solution of (1). By adopting strong base mixed liquor, the synephrine belongs to ephedrine in alkaloids, phenolic hydroxyl and amino simultaneously exist in a molecular structure, so the synephrine has amphiprotic property and can be combined with acid and alkali to form salt, and the synephrine and the strong base mixed liquor are combined to form salt through elution of the strong base mixed liquor, so the synephrine and the strong base mixed liquor are eluted together, the elution effect of the synephrine is improved, the pH value of the eluent is adjusted to be 5-7 by adding acid, and the acid reacts with the strong base in the eluent in the acid adding process, so that the synephrine is reduced into free synephrine from the generated salt. And a nanofiltration membrane is adopted for desalting subsequently, and a concentration effect is achieved at the same time. The strong alkali mixed liquid bagComprises 0.05 to 0.5 percent of KOH, 0.05 to 1 percent of NaOH or 0.05 to 0.5 percent of Ca (OH)2The content of the strong base in the strong base mixed solution is lower because the more the content of the strong base is, the higher the concentration is, the more the impurities are eluted from the strong acid cation resin, and the lower the content of the synephrine is. The synephrine forms salts under the strong alkali condition, the pH value is adjusted after elution, and the synephrine is reduced to form free synephrine, and partial racemization reaction of the synephrine possibly occurs during the separation of ion exchange resin to generate isomers, but the use is not influenced.
Preferably, the strong alkali mixed solution comprises a mixed solution of 0.1% by mass of NaOH and 0.3% by mass of KOH; or the alkali mixed solution comprises 0.4 percent of NaOH and 0.1 percent of Ca (OH)2The mixed solution of (1); or the alkali mixed solution comprises 0.2 percent of Ca (OH)2And a mixed solution of 0.1% by mass of KOH.
In the embodiment, the volume of the strong alkali mixed solution is 3 BV-4 BV, and the flow rate of the strong alkali mixed solution is 1.5 BV/h-4 BV/h. Above-mentioned, the speed of hesperidin mother liquor appearance of loading, the velocity of flow of water and strong alkali mixed solution all can be controlled through the measurement pump control, and the velocity of flow of strong alkali mixed solution is inversely proportional with the concentration of strong alkali mixed solution, and the content of strong alkali is lower in the strong alkali mixed solution promptly, and the velocity of flow of strong alkali mixed solution then can be adjusted faster.
In the embodiment, the sampling speed of the hesperidin mother liquor is 6 BV/h-15 BV/h, the volume of water elution is 3 BV-4 BV, and the speed of water elution is 1.5 BV/h-4 BV/h.
In this example, a 50nm to 500nm ceramic membrane was used for ultrafiltration in step S2. The neutralization solution passes through a 50-100 nm ceramic membrane to remove impurities such as pigments and macromolecular substances in the neutralization solution so as to ensure the purity of the obtained synephrine, moreover, the degrees of the macromolecular substances and the pigments intercepted by different ceramic membranes are different, the smaller the pore diameter of the ceramic membrane is, the more the macromolecular substances and the pigments intercepted are, the better the impurity removal effect is, but the slower the speed is. The ceramic membrane with the thickness of 50 nm-500 nm can meet the requirement of removing impurities.
In the embodiment, the nanofiltration membrane in the step S2 is a nanofiltration membrane of 100 Da-1000 Da. And (3) the neutralization solution passing through the 50-500 nm ceramic membrane passes through a nanofiltration membrane, and the nanofiltration membrane can allow water and monovalent salt ions to pass through, so that the effects of desalting and concentrating can be achieved, and the neutralization solution is concentrated to 1/100-1/200 of the volume of the original hesperidin mother solution, so that synephrine crystals can be separated out conveniently.
In the embodiment, the concentrated solution in the step S2 is stirred at 5-15 ℃, is kept stand for 10-48 h for crystallization, is filtered by a plate-and-frame filter, and is dried to obtain synephrine. The synephrine is crystallized and separated in a cooling crystallization mode, the synephrine has low solubility at the temperature of 5-10 ℃, the crystallization speed can be accelerated by stirring or adding high-content synephrine seed crystals, so that the synephrine is separated out, and the synephrine is filtered and dried by a plate-and-frame filter to obtain the novel ponin coarse crystals.
In this embodiment, in step S1, hydrochloric acid with a concentration of 10% to 30% is used to adjust the pH of the eluent. Adjusting the pH value of the eluent to 5-7 by 10% -30% hydrochloric acid to obtain synephrine.
Examples
Synephrine standards were purchased from jiugui biosciences 110727.
The synephrine content was determined using the method of determining synephrine content in appendix C of the foreign trade industry Standard WM/T5-2004.
Example 1
The method for separating synephrine from hesperidin waste liquid comprises the following steps:
s1, loading pretreated 300kg of C100E strong acid cation resin into a stainless steel cylinder, loading 10t of hesperidin mother liquor to C100E strong acid cation resin, wherein the loading speed of the hesperidin mother liquor is 7BV/h, after loading is finished, eluting by water, the volume of the water elution is 3.3BV, the speed of the water elution is 2BV/h, after the water elution is finished, eluting by strong base mixed liquor, wherein the strong base mixed liquor comprises a mixed solution of 0.1% by mass of NaOH and 0.3% by mass of KOH, the volume of the strong base mixed liquor is 3.3BV, the flow rate of the strong base mixed liquor is 2BV/h, collecting eluent after the elution of the strong base mixed liquor, and adjusting the pH value of the eluent to 7 by using 10% hydrochloric acid to obtain a neutralization solution;
and S2, ultrafiltering the neutralized solution by adopting a 100nm ceramic membrane, concentrating by adopting a 200Da nanofiltration membrane, stirring the concentrated solution at 5 ℃, standing for crystallization for 12 hours, filtering by adopting a plate-and-frame filter, and drying to obtain synephrine.
5kg of synephrine crystals with a synephrine content of 98.51% were obtained.
Example 2
S1, loading pretreated 300kg of C100E strong acid cation resin into a stainless steel cylinder, loading 15t of hesperidin mother liquor to C100E strong acid cation resin, wherein the sampling speed of the hesperidin mother liquor is 10BV/h, eluting by water after sampling is finished, the volume of the water elution is 3.34BV, the water elution speed is 3BV/h, eluting by strong base mixed liquor after the water elution is finished, and the strong base mixed liquor comprises 0.4% of NaOH by mass and 0.1% of Ca (OH) by mass2The volume of the strong base mixed solution is 3.34BV, the flow rate of the strong base mixed solution is 3BV/h, the eluent eluted by the strong base mixed solution is collected, hydrochloric acid with the concentration of 20 percent is adopted to adjust the pH value of the eluent to be 6.5, and a neutralization solution is obtained;
and S2, carrying out ultrafiltration on the neutralized solution by adopting a 50nm ceramic membrane, then concentrating by adopting a 50Da nanofiltration membrane, stirring the concentrated solution at 15 ℃, standing for crystallization for 24 hours, filtering by adopting a plate-and-frame filter, and drying to obtain synephrine.
7.8kg of synephrine crystals, and the content of synephrine is 98.13%.
Example 3
S1, loading pretreated 300kg of C100E strong acid cation resin into a stainless steel cylinder, loading 15t of hesperidin mother liquor to the C100E strong acid cation resin, wherein the hesperidin mother liquor sampling speed is 10BV/h, eluting by water after sampling is finished, the volume of water elution is 3.5BV, the water elution speed is 3BV/h, eluting by strong base mixed liquor after water elution is finished, and the strong base mixed liquor comprises 0.2 percent of Ca (OH) by mass2And a mixed solution of 0.1% KOH by mass fraction, wherein the volume of the strong base mixed solution is 3.5BV, the flow rate of the strong base mixed solution is 3BV/h, and the strong base mixed solution is collected and washedAdjusting the pH value of the eluent to 7 by adopting hydrochloric acid with the concentration of 20% to obtain a neutralized solution;
and S2, ultrafiltering the neutralized solution by adopting a 500nm ceramic membrane, concentrating by adopting a 500Da nanofiltration membrane, stirring the concentrated solution at 10 ℃, standing for crystallization for 24 hours, filtering by adopting a plate-and-frame filter, and drying to obtain synephrine.
7.7kg of synephrine crystals, and the content of synephrine is 98.20%.
The synephrine prepared in example 1 was chromatographed with the commercial standard synephrine.
Chromatographic conditions column Diamonsil C18 column (150 mm. times.6 mm, 5 μm); the mobile phase is acetonitrile, water, phosphoric acid and sodium dodecyl sulfate with the volume fraction ratio of 30: 70: 0.1: 0.2, and the flow rate is 1 mL/min; the detection wavelength is 230 nm; the column temperature is 35 ℃; the sample size is 10 μ L, as shown in FIG. 1 and FIG. 2, FIG. 1 is a liquid chromatogram of synephrine standard, wherein 8.239 is synephrine peak; FIG. 2 is a liquid chromatogram of synephrine from example 1 of the present invention, wherein 8.295 is the synephrine peak, demonstrating that synephrine was obtained in the preparation of the present invention.
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 (10)
1. A method for separating synephrine from hesperidin waste liquid is characterized by comprising the following steps:
s1, feeding the hesperidin mother liquor onto a strong acid cation resin, eluting with water after the sample feeding is finished, eluting with a strong base mixed liquor after the water elution is finished, collecting the eluent eluted by the strong base mixed liquor, and adjusting the pH value of the eluent to 5-7 to obtain a neutralized solution;
and S2, carrying out ultrafiltration on the neutralized liquid, then concentrating the neutralized liquid through a nanofiltration membrane, cooling and crystallizing the concentrated liquid, filtering and drying to obtain synephrine.
2. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
the strong acid cation resin is C100E strong acid cation resin.
3. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
the strong alkali mixed solution comprises 0.05 to 0.5 mass percent of KOH, 0.05 to 1 mass percent of NaOH or 0.05 to 0.5 mass percent of Ca (OH)2At least two kinds of mixed solution of (1).
4. The method for separating synephrine from hesperidin waste liquid as claimed in claim 3, wherein,
the strong alkali mixed solution comprises a mixed solution of 0.1% by mass of NaOH and 0.3% by mass of KOH; or
The strong alkali mixed solution comprises 0.4 percent of NaOH and 0.1 percent of Ca (OH)2The mixed solution of (1); or
The strong alkali mixed solution comprises 0.2 percent of Ca (OH)2And a mixed solution of 0.1% by mass of KOH.
5. The method for separating synephrine from hesperidin waste liquid as claimed in claim 3, wherein,
the volume of the strong alkali mixed solution is 3 BV-4 BV, and the flow rate of the strong alkali mixed solution is 1.5 BV/h-4 BV/h.
6. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
the sampling speed of the hesperidin mother liquor is 6 BV/h-15 BV/h,
the volume of water elution is 3 BV-4 BV, and the speed of water elution is 1.5 BV/h-4 BV/h.
7. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
in the step S2, a ceramic membrane with the thickness of 50 nm-500 nm is adopted for ultrafiltration.
8. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
in the step S2, the nanofiltration membrane is a nanofiltration membrane of 100 Da-1000 Da.
9. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
and (5) stirring the concentrated solution obtained in the step (S2) at the temperature of 5-15 ℃, standing and crystallizing for 10-48 h, filtering by adopting a plate-and-frame filter, and drying to obtain synephrine.
10. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
step S1, hydrochloric acid with the concentration of 10% -30% is used for adjusting the pH value of the eluent.
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| CN113527120A (en) * | 2021-07-19 | 2021-10-22 | 江西岐黄农业科技有限公司 | Extraction process of levo-synephrine |
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| CN113527120A (en) * | 2021-07-19 | 2021-10-22 | 江西岐黄农业科技有限公司 | Extraction process of levo-synephrine |
| CN113527120B (en) * | 2021-07-19 | 2023-08-18 | 江西岐黄农业科技有限公司 | Extraction process of levo synephrine |
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