CN108727188B - Method for catalytically synthesizing aspirin - Google Patents
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Abstract
The invention discloses a method for catalytically synthesizing aspirin, which belongs to the technical field of organic synthesis chemistry, wherein tyrosine is used as a catalyst to catalyze esterification reaction of acetic anhydride and salicylic acid, and aspirin is synthesized under an ultrasonic condition, an experimental result shows that the yield of a product obtained by reaction under the conditions is 93.43%, and the purity of the product is high, wherein the ultrasonic power is 500W, the molar ratio of the acetic anhydride to the salicylic acid is 2:1, the ultrasonic reaction time is 20min, the reaction temperature is 60 ℃, and the catalyst dosage is 8% of the mass of the salicylic acid. The invention avoids the defects that the traditional preparation method is easy to generate side reaction, the product has poor color and is not beneficial to purification, and the concentrated sulfuric acid is used as the catalyst, has stronger corrosion effect on equipment, generates a large amount of waste acid and has higher environmental pollution, thereby having better application value.
Description
Technical Field
The invention belongs to the technical field of organic synthetic chemistry, and particularly relates to a method for catalytically synthesizing aspirin.
Background
Aspirin, one of the three classic drugs in the world's medical history, is known as 2- (acetoxy) benzoic acid, and is also known as acetylsalicylic acid, which can be synthesized from acetic anhydride or acetyl chloride and salicylic acid. It is synthesized for the first time in 1853 years, and is used in 1899 years, aspirin has strong antipyretic and analgesic effects, and can be used for treating headache, toothache, muscular mass, neuralgia, chronic dull pain, common cold, fever, etc. The anti-inflammatory and antirheumatic effects are 2-3 times stronger than those of sodium salicylate, and the medicine has definite curative effects on rheumatic fever, active rheumatic arthritis and the like, and is a preferred medicine. In recent years, research shows that aspirin has a strong platelet aggregation inhibiting effect, so that aspirin is applied to the field of prevention and treatment of cardiovascular and cerebrovascular diseases. Meanwhile, recent research shows that aspirin can inhibit tumor growth and metastasis, and has cancer prevention and anticancer effects. In addition, aspirin has new uses of preventing senile dementia, inhibiting AIDS virus propagation, etc. With the continuous and deep research on aspirin by scientists, the application range of aspirin, as a typical representative of 'new use of old medicine', is gradually expanding. Its important side effect is pylorospasm and gastrointestinal reaction stimulating gastric mucosa, which can cause gastrointestinal bleeding after long-term administration. Therefore, research on aspirin synthesis methods still has important value.
The traditional synthetic aspirin is prepared by using concentrated sulfuric acid as a catalyst and acetic anhydride and salicylic acid as starting materials through an esterification reaction. Concentrated sulfuric acid is used as a catalyst, and has strong oxidizing property, so that side reactions are more, the concentrated sulfuric acid is used as the catalyst, has strong corrosion effect on equipment, and has low yield which is about 60 percent generally. Therefore, the development of an environmentally friendly catalyst for aspirin synthesis has been a research hotspot in the field of organic synthesis. At present, no report is found in experiments and documents about the catalytic synthesis of aspirin by using tyrosine instead of concentrated sulfuric acid, tyrosine is used as a catalyst, the influence of the quantity ratio of reactant substances, the reaction temperature, the ultrasonic reaction time and the catalyst dosage on the product yield is explored, and the optimal synthesis conditions are better determined through an orthogonal test.
Disclosure of Invention
In order to solve the defects in the prior art, tyrosine is adopted as a catalyst, the method is mild in property and free of pollution, the reaction is carried out under the ultrasonic-assisted condition, the reaction time is shortened, the reaction temperature is reduced, the yield is over 90 percent, and the method has a certain profit space and has good application and popularization values through economic analysis of projects.
The invention provides a method for synthesizing aspirin by using a novel catalyst, which comprises the following steps:
s1, taking tyrosine as a catalyst, adding salicylic acid and acetic anhydride into a reaction container, heating in an ultrasonic water bath at 55-60 ℃ for 5-20 min, removing the reaction container from the water bath, slowly pouring ice water when the temperature of contents is 35-50 ℃, continuing to react for 20-30 min, cooling in the ice water bath for 30-45 min, stirring to completely separate out crystalline solids, performing suction filtration, washing with the ice water, draining, and drying to obtain a crude white needle aspirin product;
and S2, adding the crude aspirin obtained in the S1 into a saturated sodium bicarbonate solution, stirring until no bubbles exist, filtering insoluble substances, pouring the filtrate into a beaker filled with concentrated hydrochloric acid, stirring, placing the beaker in an ice-water bath, fully cooling to separate out solids completely, performing suction filtration, and drying to obtain the aspirin product.
Preferably, in S1, the molar ratio of the acetic anhydride to the salicylic acid starting material is 2: 1.
Preferably, in S1, the amount of catalyst tyrosine is 8% of the mass of salicylic acid.
Preferably, in S1, the time for heating in the ultrasonic water bath is 20 min.
Preferably, in S1 and S2, the drying temperature is 60-80 ℃, and the drying time is 10-30 min.
Compared with the prior art, the preparation method has the following beneficial effects:
(1) the invention adopts tyrosine as a catalyst for synthesizing aspirin, salicylic acid and acetic anhydride react under the ultrasonic condition, the reaction time is shortened, the temperature is reduced, and the tyrosine is a nontoxic catalyst; the method has the characteristics of mild reaction conditions, harmlessness, no pollution, no corrosion to equipment, simple post-treatment, high reaction yield and the like. Through economic analysis of the project, the method has certain profit space and better application and popularization values.
(2) The method takes tyrosine as a catalyst, replaces concentrated sulfuric acid to catalyze esterification reaction of acetic anhydride and salicylic acid, and synthesizes aspirin under an ultrasonic condition, and research results show that the product yield is 93.43% and the product purity is high under the condition that the ultrasonic power is 500W, the molar ratio of acetic anhydride to salicylic acid is 2:1, the ultrasonic reaction time is 20min, the reaction temperature is 60 ℃, and the catalyst dosage is 8% of the mass of the salicylic acid. The traditional preparation method is easy to generate side reaction, the product has poor color and is not beneficial to purification, concentrated sulfuric acid is used as a catalyst, has strong corrosion effect on equipment, can generate a large amount of waste acid liquid, and has great pollution to the environment. And through market economic analysis, the method has certain profit space and better application value.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a diagram of an apparatus for synthesizing aspirin according to an embodiment of the present invention;
FIG. 2 is an infrared spectrum of a product of the present invention;
FIG. 3 is a UV absorption spectrum of the product of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. Test methods in which specific conditions are not specified in the following examples are generally carried out under conventional conditions or under conditions recommended by the respective manufacturers.
Fig. 1 schematically shows a synthesis apparatus for catalytically synthesizing aspirin according to an embodiment of the present invention.
1.1 reagents and instruments
The reagents used in the present invention: salicylic acid (CP), acetic Anhydride (AR), tyrosine (AR); the salicylic acid needs to be dried in advance; redistilling acetic anhydride, and collecting 139-140 ℃ fractions.
The apparatus used in the present invention: DF-II heat collection type magnetic heating stirrer (medical instrument factory of Jintan city, Jiangsu province); XRC-1 micro melting point tester (Sichuan university science and technology Co., Ltd.); KQ-100E ultrasonic cleaner (Kunshan ultrasonic instruments Co., Ltd.); 8HZ-D (III) circulating water vacuum pump (Henan Zhicheng science and technology Co., Ltd.); PB1502-L electronic balance; TU-1810 ultraviolet-visible spectrophotometer (Beijing Pujingyo general instruments Co., Ltd.); fourier Infrared Spectroscopy FT-IR200(Thermo Nicolet Corp.).
1.2 principle of the experiment
Salicylic acid is a compound with bifunctional groups, and both hydroxyl and carboxyl groups can undergo esterification reaction. Acylation of acetic anhydride produces acetylsalicylic acid (aspirin) in the following reaction scheme:
1.3 Experimental methods
Salicylic acid, acetic anhydride and tyrosine are respectively added into a 150mL dry three-neck flask according to the metering ratio, slightly mixed, fixed in a water bath of an ultrasonic cleaner at a certain temperature, the ultrasonic power is 500W, and simultaneously, the reaction phenomenon in the reaction flask is timed and observed. Taking out after reacting for a certain time, washing the inner wall of the flask by using ice water, adding a certain amount of water after crystals are formed, placing the mixture into an ice water bath for cooling so as to ensure that the crystals are completely crystallized, carrying out suction filtration, washing a filter cake by using a small amount of distilled water, and drying to obtain a white needle-like aspirin crude product. Adding the crude product into saturated sodium bicarbonate solution, stirring until no bubbles exist, filtering out insoluble substances, slowly pouring the filtrate into a beaker containing concentrated hydrochloric acid, stirring, placing the beaker in an ice water bath for fully cooling to separate out solids completely, performing suction filtration, and drying to obtain the aspirin product. And (3) detecting the product by using a 1% ferric trichloride solution, wherein the solution does not generate a color reaction, and the product purity is better.
To verify the effect of the present invention, we performed the following experiment. The influence of n (salicylic acid) to n (anhydride), ultrasonic time, ultrasonic temperature and catalyst dosage on the product yield is respectively examined.
The method for catalytically synthesizing aspirin provided by the embodiment of the invention comprises the following embodiments.
Example 1
The method for catalytically synthesizing aspirin provided by the embodiment comprises the following steps of:
respectively adding 6.9g (50mmol) of salicylic acid and 0.552g of tyrosine into a 150mL dry three-neck flask, then adding 5.1g (50mmol) of acetic anhydride, mixing, fixing the mixture in a water bath of an ultrasonic cleaner at 50 ℃, wherein the ultrasonic power is 500W, the reaction time is 15min, then removing the three-neck flask from the water bath, washing the inner wall of the flask by ice water, adding a certain amount of water after crystals are formed, placing the flask in the ice water bath for cooling so as to ensure that the crystals are complete, performing suction filtration, washing a filter cake by a small amount of distilled water, and drying to obtain a crude white needle-shaped aspirin product. Adding the crude product into saturated sodium bicarbonate solution, stirring until no bubbles exist, filtering to remove insoluble substances, slowly pouring the filtrate into a beaker containing concentrated hydrochloric acid, stirring, placing the beaker in an ice water bath for fully cooling to separate out solids completely, performing suction filtration, and drying at 70 ℃ for 30min to obtain the aspirin product.
Comparative example 1
This comparative example, a process for catalytically synthesizing aspirin, was prepared in the same manner as in example 1, except that the amount of acetic anhydride used was 7.650g (75 mmol).
Comparative example 2
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 1, except that acetic anhydride was used in an amount of 10.2g (100 mmol).
Comparative example 3
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 1, except that the amount of acetic anhydride used was 12.75g (125 mmol).
Comparative example 4
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 1, except that the amount of acetic anhydride used was 15.3g (150 mmol).
Comparative example 5
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 1, except that the amount of acetic anhydride used was 17.85g (175 mmol).
50mmol of salicylic acid, 8 percent of the mass of the catalyst tyrosine, 15min of reaction time and 50 ℃ of reaction temperature, and the influence of the raw materials of n (acetic anhydride) and n (salicylic acid) in the ratio of 1: 1, 1.5: 1, 2:1, 2.5: 1, 3.0: 1 and 3.5: 1 on the yield of aspirin is examined. The results of the experiment are shown in table 1. It can be seen from Table 1 that increasing the amount of acetic anhydride promotes the reaction in the forward direction, and that when n (acetic anhydride):n (salicylic acid) is greater than 2.0:1, the yield increase is no longer significant.
TABLE 1 Effect of raw material amount on yield
Example 2
The method for catalytically synthesizing aspirin provided by the embodiment comprises the following steps of:
respectively adding 6.9g (50mmol) of salicylic acid and 0.552g of tyrosine into a 150mL dry three-neck flask, then adding 10.2g (100mmol) of acetic anhydride, mixing, fixing the mixture in a water bath of an ultrasonic cleaner at 50 ℃, wherein the ultrasonic power is 500W, the reaction time is 5min, then removing the three-neck flask from the water bath, washing the inner wall of the flask by ice water, adding a certain amount of water after crystals are formed, placing the flask in the ice water bath for cooling so as to ensure that the crystals are complete, performing suction filtration, washing a filter cake by a small amount of distilled water, and drying to obtain a crude white needle-shaped aspirin product. Adding the crude product into saturated sodium bicarbonate solution, stirring until no bubbles exist, filtering to remove insoluble substances, slowly pouring the filtrate into a beaker containing concentrated hydrochloric acid, stirring, placing the beaker in an ice water bath for fully cooling to separate out solids completely, performing suction filtration, and drying at 70 ℃ for 30min to obtain the aspirin product.
Comparative example 6
The specific preparation process of the method for catalytically synthesizing aspirin in the comparative example is the same as that of the example 2, except that the ultrasonic reaction time is 10 min.
Comparative example 7
The specific preparation process of the method for catalytically synthesizing aspirin in the comparative example is the same as that of the example 2, except that the ultrasonic reaction time is 15 min.
Comparative example 8
The specific preparation process of the method for catalytically synthesizing aspirin in the comparative example is the same as that of the example 2, except that the ultrasonic reaction time is 20 min.
Comparative example 9
The specific preparation process of the method for catalytically synthesizing aspirin in the comparative example is the same as that of the example 2, except that the ultrasonic reaction time is 25 min.
Comparative example 10
The specific preparation process of the method for catalytically synthesizing aspirin in the comparative example is the same as that of example 2, except that the ultrasonic reaction time is 30 min.
Salicylic acid is 50mmol, the dosage of the catalyst tyrosine is 8 percent of the mass of the salicylic acid, and the raw material ratio of n (acetic anhydride) to n (salicylic acid) is 2:1 under the condition of the reaction temperature of 50 ℃. And (3) investigating the influence of the ultrasonic reaction time of 5min, 10min, 15min, 20min, 25min and 30min on the aspirin yield. The results of the experiment are shown in table 2. As can be seen from Table 2, the yield gradually increased with the increase of the ultrasonic reaction time, and the yield tended to be stable after the ultrasonic reaction time exceeded 15min, since the reaction had substantially reached equilibrium.
TABLE 2 Effect of sonication reaction time on yield
Example 3
The method for catalytically synthesizing aspirin provided by the embodiment comprises the following steps of:
respectively adding 6.9g (50mmol) of salicylic acid and 0.552g of tyrosine into a 150mL dry three-neck flask, then adding 10.2g (100mmol) of acetic anhydride, mixing, fixing the mixture in a water bath of an ultrasonic cleaner at 30 ℃, wherein the ultrasonic power is 500W, the reaction time is 15min, then removing the three-neck flask from the water bath, washing the inner wall of the flask by ice water, adding a certain amount of water after crystals are formed, placing the flask in the ice water bath for cooling so as to ensure that the crystals are complete, performing suction filtration, washing a filter cake by a small amount of distilled water, and drying to obtain a crude white needle-shaped aspirin product. Adding the crude product into saturated sodium bicarbonate solution, stirring until no bubbles exist, filtering to remove insoluble substances, slowly pouring the filtrate into a beaker containing concentrated hydrochloric acid, stirring, placing the beaker in an ice water bath for fully cooling to separate out solids completely, performing suction filtration, and drying at 70 ℃ for 30min to obtain the aspirin product.
Comparative example 11
The method for catalytically synthesizing aspirin in the comparative example has the same specific preparation process as example 3, except that the water bath reaction temperature is 40 ℃.
Comparative example 12
The method for catalytically synthesizing aspirin in the comparative example has the same specific preparation process as example 3, except that the water bath reaction temperature is 50 ℃.
Comparative example 13
The specific preparation process of the new method for catalytically synthesizing aspirin is the same as that of example 3, except that the water bath reaction temperature is 60 ℃.
Comparative example 14
The method for catalytically synthesizing aspirin in the comparative example has the same specific preparation process as example 3, except that the water bath reaction temperature is 70 ℃.
Comparative example 15
The method for catalytically synthesizing aspirin in the comparative example has the same specific preparation process as example 3, and is different only in that the water bath reaction temperature is 80 ℃.
Under the condition that the amount of salicylic acid is 50mmol, the dosage of the catalyst tyrosine is 8% of the mass of the salicylic acid, the ratio of n (acetic anhydride) to n (salicylic acid) raw materials is 2:1, the ultrasonic reaction time is 15min, and the influence of the reaction temperature of 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃ and 80 ℃ on the aspirin yield is examined. The results of the experiment are shown in table 3. As can be seen from Table 3, the yield gradually increased with the increase in the reaction temperature, and the yield tended to decrease when the temperature exceeded 60 ℃. This is probably due to the increase in side reactions due to the high reaction temperature.
TABLE 3 Effect of reaction temperature on yield
Example 4
The method for catalytically synthesizing aspirin provided by the embodiment comprises the following steps of:
respectively adding 6.9g (50mmol) of salicylic acid and 0.138g of tyrosine into a 150mL dry three-neck flask, then adding 10.2g (100mmol) of acetic anhydride, mixing, fixing the mixture in a water bath of an ultrasonic cleaner at 50 ℃, wherein the ultrasonic power is 500W, the reaction time is 15min, then removing the three-neck flask from the water bath, washing the inner wall of the flask by ice water, adding a certain amount of water after crystals are formed, placing the flask in the ice water bath for cooling so as to ensure that the crystals are complete, performing suction filtration, washing a filter cake by a small amount of distilled water, and drying to obtain a crude white needle-shaped aspirin product. Adding the crude product into saturated sodium bicarbonate solution, stirring until no bubbles exist, filtering to remove insoluble substances, slowly pouring the filtrate into a beaker containing concentrated hydrochloric acid, stirring, placing the beaker in an ice water bath for fully cooling to separate out solids completely, performing suction filtration, and drying at 70 ℃ for 30min to obtain the aspirin product.
Comparative example 16
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 4, except that tyrosine was used in an amount of 0.276 g.
Comparative example 17
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 4, except that tyrosine was used in an amount of 0.414 g.
Comparative example 18
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 4, except that tyrosine was used in an amount of 0.552 g.
Comparative example 19
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 4, except that tyrosine was used in an amount of 0.690 g.
Comparative example 20
This comparative example, a process for the catalytic synthesis of aspirin, was prepared in the same manner as in example 4, except that tyrosine was used in an amount of 0.828 g.
Salicylic acid is 50mmol, the raw material ratio of n (acetic anhydride) to n (salicylic acid) is 2:1, the ultrasonic reaction time is 15min, the reaction temperature is 50 ℃, and the influence of the dosage of the catalyst tyrosine on the aspirin yield is examined. The dosage of the catalyst is respectively 2%, 4%, 6%, 8%, 10% and 12% of the mass of the salicylic acid.
The results of the experiment are shown in table 4. As can be seen from Table 4, if the amount of the catalyst is too small, the reaction conversion catalysis is insufficient; the catalyst is excessive and the yield is reduced.
TABLE 4 Effect of catalyst amount on yield
1.4 orthogonal test
According to the result of the single-factor test, 4 items of raw material ratio of n (acetic anhydride) to n (salicylic acid), ultrasonic reaction time, reaction temperature and catalyst dosage are taken as investigation factors, an orthogonal test method is adopted at three levels respectively to determine the optimal reaction condition of the test, and the result is verified.
TABLE 5 orthogonal experimental design and results
The best scheme can be obtained from the results of orthogonal experiments and is A2B3C3D2I.e. n (acetic anhydride)n (salicylic acid) is 2:1, the ultrasonic reaction time is 20min, the reaction temperature is 60 ℃, and the dosage of the catalyst is 8 percent of the mass of the salicylic acid. This result did not appear in the orthogonal experiments, in order to finally determine the experimental protocol A analyzed above2B3C3D2Whether or not it is the best solution, according to A2B3C3D2Test conditions redo the test, and the test results are shown in table 3.
TABLE 3 repeat validation test
As seen from Table 3, in A2B3C3D2The yield of aspirin under these conditions was higher than either of the one-way and orthogonal experiments, indicating that the optimization resulting from the orthogonal experiments was feasible. Namely n (acetic anhydride) and n (salicylic acid) are 2:1, the ultrasonic reaction time is 20min, the reaction temperature is 60 ℃, the dosage of the catalyst is 8 percent of the mass of the salicylic acid, and the yield is 93.43 percent under the condition.
2 results
2.1 structural characterization of the product
The structure of the purified and dried aspirin product was characterized, and the results are as follows.
2.1.1 determination of melting Point
Digital melting point analysis: the melting point of the finished product aspirin is measured to be 135-136.5 ℃ after the finished product aspirin is dried. In line with the literature reports.
2.1.2 Infrared Spectrum
As shown in FIG. 1, IR (KBr, v/cm-1): 2547-3490 (-OH); 3002, 2870.99 (-CH)2-H)；1753.11(-C＝O-CH3)，1685.97(-C＝O-OH)；1458.28，1606.01(Ar)；1370.42(-CH3) (ii) a 1306.71, 1187.64 (-OCO-); 755.41 (Ar-H). The position of the absorption peak is basically consistent with that of the standard map.
2.1.3 ultraviolet spectrum
The product was formulated as a 100mg/L solution and scanned on an ultraviolet spectrophotometer. The scanning range is 200-350 nm, and the spectrogram is shown in figure 2. The maximum absorption peak is at 229nm, and is matched with the absorption peak position of a standard product spectrum.
It should be noted that when the following claims refer to numerical ranges, it should be understood that both ends of each numerical range and any value between the two ends can be selected, and since the steps and methods used are the same as those of the embodiments, the preferred embodiments and effects thereof are described in the present invention for the sake of avoiding redundancy, but once the basic inventive concept is known, those skilled in the art may make other changes and modifications to the embodiments. Therefore, it is intended that the appended claims be interpreted as including preferred embodiments and all such alterations and modifications as fall within the scope of the invention.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include such modifications and variations.
Claims (1)
1. A method for catalytically synthesizing aspirin, comprising the steps of:
s1, using tyrosine as a catalyst, adding salicylic acid and acetic anhydride into a reaction container, wherein the molar ratio of the acetic anhydride to the salicylic acid is 2:1, the amount of the tyrosine is 8% of the mass of the salicylic acid, then reacting in an ultrasonic water bath at 55-60 ℃ for 20min, removing the reaction container from the water bath, pouring ice water when the temperature of the content is 35-50 ℃, continuing to react for 20-30 min, cooling in the ice water bath for 30-45 min, stirring to completely separate out crystalline solids, performing suction filtration, washing with the ice water, draining, and drying at 60-80 ℃ for 10-30min to obtain a white needle-like aspirin crude product;
and S2, adding the crude aspirin obtained in the S1 into a saturated sodium bicarbonate solution, stirring until no bubbles exist, filtering insoluble substances, pouring the filtrate into a beaker filled with concentrated hydrochloric acid, stirring, placing the beaker in an ice-water bath, fully cooling to separate out solids completely, performing suction filtration, and drying to obtain the aspirin product.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB798633A (en) * | 1956-02-29 | 1958-07-23 | Monsanto Chemicals | Aspirin |
| CN101045687B (en) * | 2006-03-27 | 2010-05-12 | 北京大学 | Synthesis method of ester |
| US7544831B2 (en) * | 2007-09-21 | 2009-06-09 | Council Of Scientific And Industrial Research | Green catalytic process for the synthesis of acetyl salicylic acid |
| CN103880663A (en) * | 2012-12-24 | 2014-06-25 | 青岛康地恩动物药业有限公司 | Aspirin preparation method |
| CN104945271A (en) * | 2015-05-01 | 2015-09-30 | 李玉山 | Synthesis method of levodopa methyl ester hydrochloride |
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