CN115521200A - High-content salicylic acid solution and preparation method thereof - Google Patents
High-content salicylic acid solution and preparation method thereof Download PDFInfo
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- CN115521200A CN115521200A CN202211136955.0A CN202211136955A CN115521200A CN 115521200 A CN115521200 A CN 115521200A CN 202211136955 A CN202211136955 A CN 202211136955A CN 115521200 A CN115521200 A CN 115521200A
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 title claims abstract description 177
- 229960004889 salicylic acid Drugs 0.000 title claims abstract description 89
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000000243 solution Substances 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000007864 aqueous solution Substances 0.000 claims abstract description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 18
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 18
- 238000002791 soaking Methods 0.000 claims abstract description 17
- 241000124033 Salix Species 0.000 claims abstract description 14
- 238000001914 filtration Methods 0.000 claims abstract description 12
- 230000005686 electrostatic field Effects 0.000 claims abstract description 11
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 238000000605 extraction Methods 0.000 claims abstract description 8
- 238000007789 sealing Methods 0.000 claims abstract description 5
- 230000009471 action Effects 0.000 claims abstract description 3
- 239000000706 filtrate Substances 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 238000002604 ultrasonography Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000012535 impurity Substances 0.000 abstract description 8
- 241000196324 Embryophyta Species 0.000 abstract description 6
- 235000019441 ethanol Nutrition 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000010414 supernatant solution Substances 0.000 description 3
- 238000009210 therapy by ultrasound Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- -1 analgesic Chemical compound 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003269 fluorescent indicator Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229940085675 polyethylene glycol 800 Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019614 sour taste Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P21/00—Plant growth regulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
- C07C65/10—Salicylic acid
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pest Control & Pesticides (AREA)
- General Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Botany (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a high-content salicylic acid solution and a preparation method thereof, belonging to the technical field of extraction of effective components of plants. The preparation method comprises the following steps: taking dried and crushed willow bark, adding an aqueous solution with the pH value of 2.0-3.5, soaking at normal temperature under the action of ultrasonic waves and an electrostatic field, and filtering; adding the filter residue into polyethylene glycol (PEG) water solution, reflux extracting, and filtering; adding ethanol into the filtrate, sealing, standing, sucking the upper clear solution, and removing ethanol to obtain high-content salicylic acid solution. The preparation method provided by the invention can extract the salicylic acid in the willow bark to the greatest extent, and the obtained salicylic acid solution has high concentration, low impurity content and high purity. The high-content salicylic acid solution prepared by the method does not contain ethanol, so that the method is safer and has a wider application range.
Description
Technical Field
The invention relates to the technical field of extraction of effective components of plants, in particular to a high-content salicylic acid solution and a preparation method thereof.
Background
Salicylic Acid (SA), also known as 2-hydroxybenzoic acid, has the molecular formula C 7 H 6 O 3 Belongs to a fat-soluble organic acid. A toxic white needle crystal or monoclinic prism crystal has special phenol sour taste. It is stable in air due to its high melting and boiling points, but gradually changes color when it encounters light. Solubility: it is easily soluble in hot water, diethyl ether, ethanol and propanol, and also easily soluble in hot benzene, and slightly soluble in cold water. SA is a natural plant widely existing in the plant world, is mainly used as a raw material in the pharmaceutical industry, is usually used for preparing medicines such as aspirin salicylamide, analgesic, sodium salicylate, blood control-67 and the like, is also used as a promoter for epoxy resin curing, a preservative, a fluorescent indicator, a compound masking agent, a compound indicator, a cosmetic preservative, a complexing agent for electroplating or chemical plating and the like, is a very important raw material in the pharmaceutical industry, and has a wide regulation and control effect on the aspect of plant drug resistance and the aspect of plant growth and development.
Because SA is slightly soluble in water and easily soluble in ethanol, ether and chloroform, the concentration of the prior salicylic acid solution is generally limited, the highest salicylic acid content in the prior salicylic acid solution can only reach about 8 percent, the solution contains more ethanol, the application of the salicylic acid solution is limited due to the existence of the ethanol in the salicylic acid solution, the salicylic acid is the best plant growth regulator, but the application technology is complex, the preparation difficulty of high-content salicylic acid is high, and the concentration of the prior salicylic acid solution also limits the application of the salicylic acid in agriculture.
Disclosure of Invention
The invention aims to provide a high-content salicylic acid solution and a preparation method thereof. The salicylic acid solution with the content of not less than 15wt.% can be prepared by the preparation method provided by the invention, and the solution does not contain ethanol, so that the high-content salicylic acid solution prepared by the method has a wider application range and is safer, and meanwhile, due to the improvement of the concentration of the salicylic acid, the packaging cost and the storage cost can be obviously saved, higher economic benefits are provided, and the high-content salicylic acid solution can provide possibility for new application of the salicylic acid.
In order to achieve the purpose, the invention provides the following technical scheme:
the invention adopts one of the technical schemes: the preparation method of the high-content salicylic acid solution comprises the following steps:
taking dried and crushed willow bark, adding an aqueous solution with the pH value of 2.0-3.5, soaking at normal temperature under the action of ultrasonic waves and an electrostatic field, and filtering; adding the filter residue into polyethylene glycol (PEG) water solution, reflux extracting, and filtering; adding ethanol into the filtrate, sealing, standing, sucking the supernatant, and removing ethanol to obtain high-content salicylic acid solution.
The invention firstly adopts the method of normal temperature soaking in acidic aqueous solution to primarily remove the water-soluble components in willow bark, adopts ultrasonic and electrostatic field to be matched with normal temperature soaking to promote the dissolution of the water-soluble components, and adopts the acidic aqueous solution to inhibit the dissolution of salicylic acid.
According to the method, the willow bark is extracted by adopting the polyethylene glycol aqueous solution, so that the salicylic acid in the willow bark can be extracted to the maximum extent, and the added polyethylene glycol can greatly increase the solubility of the salicylic acid, so that the salicylic acid in the high-content salicylic acid solution prepared in the later period can still stably exist in the solution under the low-temperature condition.
According to the invention, the ethanol is added into the extracting solution, so that water-soluble saccharides and pigments in the extracting solution can be settled, and the effect of removing impurities is achieved.
Preferably, the intensity of said ultrasound>2W/cm 2 (ii) a The voltage of the electrostatic field is 30-50 kV, and the frequency is 50Hz.
Preferably, the soaking times at normal temperature are not less than 2 times, the material-liquid ratio of each soaking is 1g.
Preferably, the volume mass ratio of the polyethylene glycol aqueous solution to the willow bark is 10mL.
Preferably, the molecular weight of the polyethylene glycol is 400 to 800.
Preferably, the mass fraction of the polyethylene glycol in the polyethylene glycol aqueous solution is 0.5%.
Preferably, the reflux extraction time is 60-90 min.
Preferably, the adding amount of the ethanol is 3 to 4 times of the volume of the polyethylene glycol aqueous solution.
Preferably, the method for removing ethanol is as follows: concentrating the clear solution at 70-80 ℃ until the volume of the clear solution is 1/100 of the original volume, adding diethyl ether with the volume of 1/3-1/2 of the volume of the concentrated solution, and continuously heating at 55-60 ℃ for 10-12 min to finish the step of removing the ethanol.
The invention adopts a mode of adding ether into the concentrated solution, and can take out the residual ethanol in the aqueous solution when the ether is distilled off due to the extremely low boiling point (34.5 ℃) of the ether and the good compatibility with the ethanol, thereby achieving the purpose of removing the ethanol more thoroughly.
The second technical scheme of the invention is as follows: the high-content salicylic acid solution is prepared according to the preparation method of the high-content salicylic acid solution, and the mass fraction of salicylic acid in the high-content salicylic acid solution is not less than 15%.
The beneficial technical effects of the invention are as follows:
the preparation method provided by the invention can extract the salicylic acid in the willow bark to the greatest extent, and the obtained salicylic acid solution has high concentration, low impurity content and high purity.
The high-content salicylic acid solution prepared by the method does not contain ethanol, so that the method is safer and has a wider application range.
The high-content salicylic acid solution prepared by the method can obviously save the packaging cost and the storage cost and provide higher economic benefit.
Detailed Description
Reference will now be made in detail to various exemplary embodiments of the invention, the detailed description should not be construed as limiting the invention but rather as a more detailed description of certain aspects, features and embodiments of the invention. It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
Further, for numerical ranges in this disclosure, it is understood that each intervening value, between the upper and lower limit of that range, is also specifically disclosed. Every intervening value, to the extent any stated or intervening value in a stated range, and every other stated or intervening value in that stated range, is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention.
As used herein, the terms "comprising," "including," "having," "containing," and the like are open-ended terms that mean including, but not limited to.
The "%" used in the embodiments of the present invention means mass% unless otherwise specified.
Example 1
Preparation of high content salicylic acid solution:
(1) Taking fresh willow bark, sucking impurities with clear water, drying at 105 deg.C for 6 hr, removing, pulverizing with plant pulverizer, and sieving with 100 mesh sieve;
(2) Weighing 10.0g of willow bark powder sieved in the step (1), adding 100mL of aqueous solution with pH value adjusted to 2.0 by hydrochloric acid, and performing ultrasonic treatment (intensity of 5W/cm) 2 ) Soaking in electrostatic field (30kV, 50Hz) at room temperature for 30min, filtering, repeating the above soaking steps, filtering, and washing the filter residue with water to neutral;
(3) And (3) transferring the filter residue washed by the water in the step (2) to a 250mL round-bottom flask, adding 100mL of 0.5% PEG400 aqueous solution, boiling, carrying out condensation reflux extraction for 60min, cooling, transferring to a 1L beaker, adding 400mL of absolute ethyl alcohol, standing for 12h, sucking the supernatant solution, measuring 200mL, transferring to a rotary evaporator, concentrating at 75 ℃ until the volume is about 2mL, cooling, adding 1mL of diethyl ether, heating to 55 ℃, and carrying out rotary evaporation for 10min to obtain the high-content salicylic acid solution.
Example 2
Preparation of high-content salicylic acid solution:
(1) Same as example 1;
(2) Weighing 10.0g of willow bark powder sieved in the step (1), adding 100mL of aqueous solution with pH value adjusted to 3.5 by hydrochloric acid, and performing ultrasonic treatment (intensity of 5W/cm) 2 ) Soaking in electrostatic field (40kV, 50Hz) at room temperature for 30min, filtering, repeating the above soaking steps for 2 times, filtering, and washing the filter residue with water to neutral;
(3) And (3) transferring the filter residue washed by the water in the step (2) to a 250mL round-bottom flask, adding 100mL of 0.5% PEG400 aqueous solution, boiling, carrying out condensation reflux extraction for 90min, cooling, transferring to a 1L beaker, adding 300mL of absolute ethyl alcohol, standing for 12h, sucking the supernatant solution, measuring 200mL, transferring to a rotary evaporator, concentrating at 70 ℃ until the volume is about 2mL, cooling, adding 0.7mL of diethyl ether, heating to 60 ℃, and carrying out rotary evaporation for 10min to obtain the high-content salicylic acid solution.
Example 3
Preparation of high content salicylic acid solution:
(1) Same as in example 1;
(2) Weighing 10.0g of willow bark powder sieved in step (1), adding 100mL of aqueous solution with pH adjusted to 2.0 by hydrochloric acid, and performing ultrasonic treatment (intensity of 5W/cm) 2 ) Soaking in electrostatic field (50kV, 50Hz) at room temperature for 30min, filtering, repeating the above soaking steps, filtering, and washing the filter residue with water to neutral;
(3) And (3) transferring the filter residue washed by the water in the step (2) to a 250mL round-bottom flask, adding 100mL of 0.5% PEG800 aqueous solution, boiling, carrying out condensation reflux extraction for 70min, cooling, transferring to a 1L beaker, adding 400mL of absolute ethyl alcohol, standing for 12h, sucking the supernatant solution, measuring 200mL, transferring to a rotary evaporator, concentrating at 80 ℃ until the volume is about 2mL, cooling, adding 0.85mL of diethyl ether, heating to 55 ℃, and carrying out rotary evaporation for 12min to obtain the high-content salicylic acid solution.
Comparative example 1
Preparation of high content salicylic acid solution:
the difference from example 1 is that no electrostatic field is applied during the soaking at normal temperature in step (2), and the other operations are the same as example 1.
Comparative example 2
Preparation of high-content salicylic acid solution:
the difference from example 1 is that the 0.5% aqueous solution of PEG400 in step (3) was replaced with water, resulting in the precipitation of white crystals in the subsequent rotary evaporation and failure to produce a stable salicylic acid solution.
Comparative example 3
Preparation of high content salicylic acid solution:
the procedure of adding diethyl ether to the step (3) for rotary evaporation was omitted as compared with example 1, and the other procedures were the same as in example 1.
The influence of the preparation method of the invention on the purity of salicylic acid was examined:
taking 1mL of supernatant obtained by settling and standing absolute ethyl alcohol in the preparation processes of examples 1-3 and comparative examples 1 and 2, and measuring the content c of salicylic acid in the supernatant by using a high performance liquid chromatograph 1 (mg/mL) and the content c of polyethylene glycol 400 or polyethylene glycol 800 2 (mg/mL), 50mL of supernatant was measured at the same time, evaporated to dryness, the weight m (mg) of the solid matter remaining was measured, the purity (%) of salicylic acid in the supernatant liquid was calculated, the formula was shown in formula (1), and the calculation results are shown in Table 1:
TABLE 1
As can be seen from Table 1, according to the preparation method provided by the invention, the salicylic acid solution with low impurity content and high purity can be obtained. Under the condition of omitting an electrostatic field, the purity of the prepared salicylic acid solution is reduced, probably because the impurities are removed less in the early stage, the content of the impurities in the extracting solution obtained by reflux extraction is higher, and the ethanol cannot be precipitated completely, so that the purity of the prepared salicylic acid solution is not high. In the case of no polyethylene glycol addition, the calculated purity is significantly reduced since the total amount of salicylic acid extracted is greatly reduced, while the impurities are almost unchanged.
The residual amount of ethanol in the high content salicylic acid solutions prepared in examples 1 to 3 and comparative examples 1 and 3 was measured:
the detection was performed by gas chromatography, and the detection results are shown in table 2.
TABLE 2
As can be seen from Table 2, the ethanol content of the high-content salicylic acid solution prepared by the method provided by the invention is extremely low and is lower than 0.5% of the ethanol residue limit specified in Chinese pharmacopoeia. The final addition of diethyl ether effectively reduces the ethanol content of the salicylic acid solution.
The salicylic acid content (%) in the high-content salicylic acid solutions obtained in examples 1 to 3 and comparative examples 1 and 3 was measured:
the results of measurement by HPLC are shown in Table 3.
As can be seen from Table 3, according to the preparation method provided by the invention, a high-content salicylic acid solution with the mass fraction of not less than 18% can be prepared.
The stability of the high content salicylic acid solutions prepared in examples 1 to 3 of the present invention was examined:
taking 0.8mL of the high-content salicylic acid solution prepared in each of examples 1-3, storing in a sealed manner in a dark condition, observing whether each solution is precipitated or not in 1, 2, 3, 4 and 6 months respectively, taking an 18% salicylic acid solution prepared from a 20% ethanol water solution as a control group, placing each group of samples in a transparent container, and recording the observation results, wherein the results are shown in Table 4;
taking 0.8mL of the high-content salicylic acid solution prepared in the embodiments 1-3, storing the solution in an open manner under a dark condition, observing whether the solution is precipitated or not in 5, 10, 15, 20 and 30 days respectively, taking 18% salicylic acid solution prepared from 20% ethanol water solution as a control group, placing all the groups of samples in a transparent container, and recording the observation result (adding water for complementing when the volume of the solution is reduced in the observation process) as shown in Table 4;
TABLE 4
As can be seen from Table 4, the high-content salicylic acid solution prepared by the method has good stability and can be stored for a long time, and when ethanol in the salicylic acid solution dissolved by ethanol volatilizes, salicylic acid crystals are separated out, so that the requirement on the sealing degree of the system in the storage process is high, and the salicylic acid solution is not suitable for long-term storage. The control group is observed to precipitate after being sealed for 6 months, probably because the sealing is not thorough enough, part of ethanol volatilizes to cause the precipitation of salicylic acid crystals, and the liquid level is observed to slightly drop when the storage container is checked.
The above-described embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solutions of the present invention can be made by those skilled in the art without departing from the spirit of the present invention, and the technical solutions of the present invention are within the scope of the present invention defined by the claims.
Claims (10)
1. The preparation method of the high-content salicylic acid solution is characterized by comprising the following steps of:
taking dried and crushed willow bark, adding an aqueous solution with the pH value of 2.0-3.5, soaking at normal temperature under the action of ultrasonic waves and an electrostatic field, and filtering; adding the filter residue into polyethylene glycol aqueous solution, reflux extracting, and filtering; adding ethanol into the filtrate, sealing, standing, sucking the upper clear solution, and removing ethanol to obtain high-content salicylic acid solution.
2. The method for preparing the high content salicylic acid solution according to claim 1 characterized in that the intensity of the ultrasound is>2W/cm 2 (ii) a The voltage of the electrostatic field is 30-50 kV, and the frequency is 50Hz.
3. The method for preparing a high-content salicylic acid solution according to claim 1, wherein the soaking at normal temperature is performed for not less than 2 times, the ratio of material to liquid for each soaking is 1g to 10mL, and the soaking time is 30-40 min.
4. The method for preparing a high-content salicylic acid solution according to claim 1, wherein the volume-to-mass ratio of the polyethylene glycol aqueous solution to the willow bark is 10ml.
5. The method for preparing a high-content salicylic acid solution according to claim 1, wherein the molecular weight of the polyethylene glycol is 400-800.
6. The method for preparing the high-content salicylic acid solution according to claim 5, wherein the mass fraction of the polyethylene glycol in the polyethylene glycol aqueous solution is 0.5%.
7. The high-content salicylic acid solution and the preparation method thereof according to claim 1 characterized in that the time of the reflux extraction is 60-90 min.
8. The method for preparing a high-content salicylic acid solution according to claim 1, wherein the amount of the ethanol added is 3-4 times of the volume of the polyethylene glycol aqueous solution.
9. The method for preparing the high content salicylic acid solution according to claim 1, wherein the method for removing ethanol is: concentrating the clear solution at 70-80 ℃ until the volume of the clear solution is 1/100 of the original volume, adding diethyl ether with the volume of 1/3-1/2 of the volume of the concentrated solution, and continuously heating at 55-60 ℃ for 10-12 min to finish the step of removing the ethanol.
10. The high-content salicylic acid solution prepared by the method according to any one of claims 1-9, wherein the mass fraction of salicylic acid in the high-content salicylic acid solution is not less than 15%.
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| CN106726690A (en) * | 2016-12-27 | 2017-05-31 | 广东迪美新材料科技有限公司 | A kind of water-soluble salicylic acid microballoon and preparation method thereof |
| CN110840834A (en) * | 2019-12-09 | 2020-02-28 | 山东光普医疗科技有限公司 | Preparation process of 30% concentration liquid slow-release salicylic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106726690A (en) * | 2016-12-27 | 2017-05-31 | 广东迪美新材料科技有限公司 | A kind of water-soluble salicylic acid microballoon and preparation method thereof |
| CN110840834A (en) * | 2019-12-09 | 2020-02-28 | 山东光普医疗科技有限公司 | Preparation process of 30% concentration liquid slow-release salicylic acid |
Non-Patent Citations (1)
| Title |
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| MARIANNE C. VERBERNE 等: "Method for the Extraction of the Volatile Compound Salicylic Acid from Tobacco Leaf Material" * |
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