CN112830881B - 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 to 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 the strong acid cation resin, and the elution is carried out through the low-concentration strong base mixed liquid, 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 hundred million adult overweight (body Mass index BMI) about 25kg/m 2 ～29.9kg/m 2 ) At least 300 million people are obese (BMIP 30 kg/m) 2 ) In particular, the diseases directly cause diabetes, cardiovascular diseases, hypertension, cancer and the likeIncreased morbidity and mortality. Therefore, the treatment of obesity and hyperlipidemia attracts 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 lime (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.
Taking citrus peel dregs from patent application No. 201410647518.4, extracting with ethanol water solution to obtain synephrine crude 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 50-70% ethanol eluent to 2.5-4.5 with hydrochloric acid, extracting with ethyl acetate, and then carrying out rotary evaporation to remove the ethyl acetate; dissolving with water with pH of 6-8, adjusting pH = 6-8 with sodium hydroxide, then loading the mixture into an XAD18 chromatographic column, eluting impurities with water after loading the column, eluting synephrine with 5-20% ethanol water solution, collecting eluent step by step, using a large amount of ethyl acetate in the patent, wherein the ethyl acetate is also called ethyl acetate, pure ethyl acetate is colorless and transparent liquid with pungent smell, and adopting a mode of gradient elution twice on the column, the process is complex, the yield is low, and the industrial production is difficult to carry out.
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 to 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 is used.
Further, the strong alkali mixed solution comprises KOH with the mass fraction of 0.05 to 0.5 percent, naOH with the mass fraction of 0.05 to 1 percent or Ca (OH) with the mass fraction of 0.05 to 0.5 percent 2 At least two kinds of mixed solution of (1).
Further, the strong alkali mixed solution includes a mixed solution of 0.1% by mass of NaOH and 0.3% by mass of KOH; alternatively, the alkali mixture comprises 0.4% by mass of NaOH and 0.1% by mass of Ca (OH) 2 The mixed solution of (1); alternatively, the alkali mixed solution comprises 0.2% by mass of Ca (OH) 2 And 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.
Furthermore, in the step S2, a ceramic membrane with the thickness of 50 nm-500 nm is adopted for ultrafiltration.
Furthermore, the nanofiltration membrane in the step S2 adopts a nanofiltration membrane of 100Da to 1000 Da.
Further, stirring the concentrated solution in the step S2 at the temperature of 5-15 ℃, standing for crystallization for 10-48 h, filtering by adopting a plate-and-frame filter, and drying to obtain synephrine.
Further, in step S1, hydrochloric acid with the concentration of 10% -30% is used for adjusting the pH value of the eluent.
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 the synephrine from the hesperidin waste liquid carries out ion exchange through the strong acid cation resin, and elutes through the low-concentration strong base mixed liquid, the synephrine generates salt under the strong base condition, the pH value of the eluent is adjusted to be 5-7 after the elution so as to reduce the synephrine back to a free state, the operation method is controllable, no strong pungent smell exists, the requirements on production equipment and environment are low, and the requirements on green production are met.
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 to concentrate synephrine, physical treatment is carried out, energy consumption is low, chemical structure change is prevented, water and monovalent salt ions can pass through the nanofiltration membrane, so that the effects of desalination and concentration are achieved, the 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, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification. In the drawings:
FIG. 1 is a liquid chromatogram of a synephrine standard of the 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, wherein 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 according to preferred embodiment 1 of the present invention, wherein 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 to 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 after the strong-base mixed liquor is eluted, and adjusting the pH value of the eluent to 5-7 to obtain a neutralized solution;
and S2, carrying out ultrafiltration on the neutralized solution, concentrating the neutralized solution through a nanofiltration membrane, cooling and crystallizing the concentrated solution, 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 the synephrine from the hesperidin waste liquid carries out ion exchange through the strong acid cation resin, and elutes through the low-concentration strong base mixed liquid, the synephrine generates salt under the strong base condition, the pH value of the eluent is adjusted to be 5-7 after the elution so as to reduce the synephrine back to a free state, the operation method is controllable, no strong pungent smell exists, the requirements on production equipment and environment are low, and the requirements on green production are met.
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, a C100E strong acid cation resin was used as the strong acid cation 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 NH 3 ·H 2 O, 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 air 3 And 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. Strongly acidic cationic tree to be used for adsorbing synephrinePretreating a lipid column, soaking for 2 hours by using a sodium chloride solution with the mass fraction of 10%, loading the column, backwashing by using distilled water until the effluent water is clear, washing by using a sodium hydroxide solution with the volume of 2 times of the column volume and the concentration of 50g/L, 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 and the concentration of 5%, and 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) 2 At least two kinds of mixed solution of (1). By adopting strong base mixed liquor, the synephrine belongs to ephedrine in alkaloid, 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, therefore, the synephrine is combined with the strong base mixed liquor to form salt through elution of the strong base mixed liquor, so that the synephrine is eluted together with the strong base mixed liquor, 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 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) 2 The 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 generates salts under the strong alkali condition, the pH value is adjusted after elution, and the synephrine is reduced to be free synephrine, partial racemization reaction of the synephrine possibly occurs during the separation of ion exchange resin, so that isomers are generated, but the use is not influenced.
Preferably, the strong alkali mixed solution includes a mixed solution of 0.1% by mass of NaOH and 0.3% by mass of KOH; alternatively, the alkali mixture comprises 0.4% by mass of NaOH and 0.1% by mass of Ca (OH) 2 The mixed solution of (1); or the alkali mixed liquor comprises 0 mass fraction.2％Ca(OH) 2 And 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 embodiment, a ceramic membrane of 50nm to 500nm is 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. The neutralization solution passing through the ceramic membrane of 50-500 nm passes through a nanofiltration membrane which can allow water and monovalent salt ions to pass through, so that the neutralization solution can play roles of desalting and concentrating and is concentrated to 1/100-1/200 of the volume of the original hesperidin mother solution so as to be convenient for the precipitation of synephrine crystals.
In the embodiment, 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. 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, hydrochloric acid with a concentration of 10% to 30% is used to adjust the pH of the eluent in step S1. The pH value of the eluent is adjusted to 5 to 7 by 10 to 30 percent hydrochloric acid, thereby obtaining the synephrine.
Examples
Synephrine standards were purchased from jiugui 110727.
The synephrine content is measured by adopting the method of annex C in 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 300kg of pretreated C100E strong acid cation resin into a stainless steel cylinder, loading 10t of hesperidin mother liquor onto the C100E strong acid cation resin, wherein the loading speed of the hesperidin mother liquor is 7BV/h, after loading is finished, eluting by water, wherein the volume of water elution is 3.3BV, the speed of water elution is 2BV/h, after water elution is finished, eluting by strong base mixed liquor, wherein the strong base mixed liquor comprises a mixed solution of 0.1 mass percent NaOH and 0.3 mass percent 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 ceramic membrane of 100nm, concentrating by adopting a nanofiltration membrane of 200Da, stirring the concentrated solution at the temperature of 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 98.51% synephrine content 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 the C100E strong acid cation resin, wherein the loading speed of the hesperidin mother liquor is 10BV/h, eluting by water after loading is finished, the volume of water elution is 3.34BV, the speed of water elution is 3BV/h, eluting by strong base mixed liquor after water elution is finished, wherein the strong base mixed liquor comprises 0.4 mass percent NaOH and 0.4 mass percent NaOH0.1％Ca(OH) 2 The 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, ultrafiltering the neutralized solution by adopting a 50nm ceramic membrane, 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 300kg of pretreated C100E strong acid cation resin into a stainless steel cylinder, loading 15t of hesperidin mother liquor onto the C100E strong acid cation resin, wherein the hesperidin mother liquor loading speed is 10BV/h, eluting with water after loading is finished, the volume of water elution is 3.5BV, the water elution speed is 3BV/h, eluting with strong base mixed liquor after water elution is finished, wherein the strong base mixed liquor comprises 0.2 mass percent of Ca (OH) 2 And 0.1 percent KOH by mass, the volume of the strong alkali mixed solution is 3.5BV, the flow rate of the strong alkali mixed solution is 3BV/h, the eluent after the elution of the strong alkali mixed solution is collected, and hydrochloric acid with the concentration of 20 percent is adopted to adjust the pH value of the eluent to 7, so as 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 1mL/min; the detection wavelength is 230nm; 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 (4)
1. A method for separating synephrine from hesperidin waste liquid is characterized by comprising the following steps:
s1, feeding the hesperidin mother liquor to 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;
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 the concentrated liquid to obtain synephrine,
wherein the strong acid cation resin is C100E strong acid cation resin;
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% by mass of NaOH and 0.1% by mass of Ca (OH) 2 The mixed solution of (1); or the strong alkali mixed solution comprises 0.2% by mass of Ca (OH) 2 And 0.1% by mass of KOH;
step S1, hydrochloric acid with the concentration of 10-30% is adopted to adjust the pH value of the eluent; in the step S2, a ceramic membrane with the thickness of 50 nm-500 nm is adopted for ultrafiltration; the nanofiltration membrane in the step S2 adopts a nanofiltration membrane of 100 Da-1000 Da.
2. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, 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.
3. The method for separating synephrine from hesperidin waste liquor 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.
4. The method for separating synephrine from hesperidin waste liquid as claimed in claim 1, wherein,
and (3) stirring the concentrated solution 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.
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