CN111620872A - Synthetic method of tetramethyluric acid and special catalyst thereof - Google Patents
Synthetic method of tetramethyluric acid and special catalyst thereof Download PDFInfo
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- CN111620872A CN111620872A CN202010424940.9A CN202010424940A CN111620872A CN 111620872 A CN111620872 A CN 111620872A CN 202010424940 A CN202010424940 A CN 202010424940A CN 111620872 A CN111620872 A CN 111620872A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/14—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with two methyl radicals in positions 1 and 3 and two methyl radicals in positions 7, 8, or 9
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/60—Platinum group metals with zinc, cadmium or mercury
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
Abstract
The application discloses a synthetic method of tetramethyluric acid. The dimethyl carbonate, the ionized water and the catalyst are added into a reaction kettle, stirred and heated to 160 ℃, the preheated uric acid is added into the reaction kettle, the stirring speed is increased, and the reaction is started. The reaction conditions were: under the action of a catalyst, the temperature is 160-180 ℃, the pressure is normal pressure, and the reaction time is 3-4 hours. The catalyst is a ruthenium-containing catalyst. The invention realizes the synthesis of the tetramethyluric acid under normal pressure. In the production process, the energy consumption can be reduced, and the requirement on equipment is lowered.
Description
Technical Field
The application relates to the technical field of organic synthesis, in particular to a synthetic method of tetramethyluric acid.
Background
Tetramethyluric acid, namely 1,3,7, 9-tetramethyluric acid, belongs to purine alkaloids and is mainly present in tender leaves of bitter tea. In recent years, tetramethyluric acid is found to have pharmacological effects of resisting depression, tranquilizing, hypnotizing, resisting inflammation and easing pain, and is one of the hot spots of research on purine alkaloids.
The 1,3,7, 9-tetramethyluric acid is methylxanthine alkaloid rich in folium Ilicis Cornutae Immaturum, and is metabolite of caffeine formed by dehydration, oxidation, methylation, etc. Because the content of the tetramethyluric acid in the traditional tea is extremely small and difficult to detect, the research and the report on the compound are few. The research contents to date mainly relate to the plant physiology of the bitter tea and the detection of the tetramethyluric acid.
The research shows that the tetramethyluric acid has good physiological activities of depression resistance, sedation hypnosis, anti-inflammation analgesia and the like, and can also relieve the stress injury of liver cells and stimulate the movement of organisms. The traditional mental disease treatment drugs have obvious mental dependence and addiction to a certain extent, and the study on the mental dependence of the tetramethyluric acid is not reported, so the tetramethyluric acid is a potential novel clinical mental disease treatment drug. Meanwhile, although the tetramethyluric acid has pharmacological activities of depression resistance, sedation hypnosis, inflammation resistance, analgesia and the like, the specific action mechanism of the tetramethyluric acid is yet to be further researched, and the research of the action mechanism lays a foundation for the development and the utilization of the tetramethyluric acid as functional food or medicine and the like.
The tetramethyluric acid is derived from natural bitter tea, the effective components of the tetramethyluric acid have safe, non-toxic and long-term eating history, and the tetramethyluric acid also has good application prospect in the aspect of medicines. At present, although the artificial synthesis of tetramethyluric acid has corresponding research, some of the existing synthetic routes relate to toxic substances; some synthesis circuits are long; some raw materials are not easy to obtain; some require biological enzyme to participate in the reaction with high cost; some reaction pressure is high, production energy consumption is high, and the like, so that a green, feasible and low-cost synthesis line is still an urgent technical problem to be solved.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a synthetic method of tetramethyluric acid.
Uric acid is the end product of purine metabolism. Is trioxypurine, and the alcohol formula of the trioxypurine is weak acid. Uric acid produced by oxidation of various purines is excreted with urine. Cheap and easily available.
Dimethyl carbonate is a green chemical with very low toxicity and is classified as a non-toxic chemical.
The invention provides a method for preparing tetramethyluric acid by using uric acid and dimethyl carbonate as reactants. Dimethyl carbonate as an electrophilic reagent can perform methylation reaction or methoxycarbonylation reaction with a nucleophilic reagent, and the reaction mechanism is as follows:
the mechanism of participating in the methoxycarbonyl reaction is base catalysis, acyl-oxygen bond breakage, bimolecular process, and reaction temperature is less than 90 ℃; the mechanism of the participation of the catalyst in the methylation reaction is base catalysis, alkoxy group breakage, bimolecular plum surpassing, and the reaction temperature is more than 120 ℃. The methylation reaction is a competitive reaction with the methoxycarbonyl reaction, and therefore, the selectivity of the methylation reaction can be improved by changing the reaction conditions. Correspondingly, the temperature is increased to more than 120 ℃, and the pressure is increased to 0.8-5 MPa, so that the tetramethyluric acid can be obtained.
Research finds that the catalyst is a main factor influencing the activity and selectivity of the DMC methylation reaction, so that the research and development of the high-efficiency, high-selectivity and recyclable catalyst is the main attack direction of the research.
The present invention contemplates the conditions under which this reaction occurs under the action of various catalysts, including: acid-base catalysts (potassium carbonate), molecular sieve catalysts (NaY type), metal oxide catalysts (zirconia), and the like. Finally, the ruthenium catalyst can reduce the reaction pressure, and if the catalyst prepared by the method provided by the invention is adopted, the synthesis reaction can be completed under normal pressure.
The specific technical scheme provided by the invention is as follows: the synthesis process is shown as the following formula:
specifically, the synthesis reaction conditions are as follows: under the action of a catalyst, the temperature is 160-180 ℃, the pressure is normal pressure, and the reaction time is 3-4 hours.
Specifically, adding dimethyl carbonate, ionized water and a catalyst into a reaction kettle, stirring and heating to 160 ℃, adding preheated uric acid into the reaction kettle, increasing the stirring speed, and starting to react; the catalyst is a ruthenium-containing catalyst.
The invention also discloses a preparation method of the catalyst, which comprises the following steps: mixing a hydrate of ruthenium trichloride and a hydrate of zinc sulfate, adding an ethanol-water solution, and stirring at room temperature to form a ruthenium-zinc-alcohol mixed system; dropwise adding a sodium hydroxide solution into the ruthenium-zinc-alcohol mixed system to obtain black precipitates, washing, adding a water-ionic liquid mixture, reducing in a sealed container by using hydrogen, leaching in the sodium hydroxide solution at 70-80 ℃ after reduction, washing to be neutral, and vacuum drying to obtain the ruthenium-zinc-alcohol mixed catalyst.
Specifically, the dropping process of the sodium hydroxide is carried out under continuous stirring, the stirring speed is 200-250 r/min, the dropping speed of the sodium hydroxide is 0.8-1.2 ml/min, and the concentration of the sodium hydroxide is 0.2-5 mol/L; and in order to fully react, the mixture needs to be stirred for a certain time after the feeding is finished.
Specifically, the water-ionic liquid mixture is a mixture of water and 1, 3-dimethyl imidazole tetrafluoroborate, and the volume ratio of the water to the ionic liquid mixture is 1.2: 1.
Specifically, the reduction conditions are as follows: reducing for 6-8 h at 160-180 ℃ and 3-4 MPa of hydrogen pressure, and stirring at 400-500 r/min.
Further, the reduction adopts temperature programming, and the specific steps are as follows: reducing at 60 deg.C under 4MPa for 2 hr, at 100 deg.C under 4MPa for 2 hr, and at 160 deg.C under 4MPa for 2 hr.
A typical embodiment of the catalyst preparation is:
adding RuCl3·xH2O and ZnSO4·7H2Preparing a mixed solution from O according to a certain proportion (the molar ratio is 2:1), stirring and dissolving the mixed solution by using an ethanol-water solution with a proper volume ratio (1:2) at room temperature, wherein the total volume of the ethanol-water solution is 6-10 times of that of the mixed solution, and forming a mixed system. And (2) dropwise adding a NaOH solution (0.2-6 mol/L) into the ruthenium-zinc alcohol aqueous solution system at a certain speed (0.8-1.2 ml/min), wherein the dropwise adding process is carried out at room temperature and a certain stirring speed (200-250 r/min), and in order to fully react, stirring for a certain time is required after the feeding is finished. A black precipitate was obtained.
After the system was allowed to stand for 12 hours, the black precipitate was dropped to the bottom of the vessel, and the supernatant was poured off. Washing the precipitate with ionized water to neutrality, mixing with water-ionic liquid (1, 3-dimethyl imidazole tetrafluoroborate) mixture in certain volume ratio (1:1), and hydrogen reducing in a high pressure reactor.
Reducing for 6 hours at 160 ℃ and 4.0MPa of hydrogen pressure, stirring at 400r/min, reducing for 10 hours, and leaching in a certain amount of 15% NaOH solution for 5 hours at 70-80 ℃ after reduction. Then washed with water to neutral. And (5) performing suction filtration, and placing in a vacuum drier for later use.
Has the advantages that: the method provided by the invention realizes the synthesis of tetramethyluric acid. Compared with the prior art, the synthesis of the tetramethyluric acid under normal pressure is realized under the action of the special catalyst. In the production process, the energy consumption can be reduced, and the requirement on equipment is lowered.
Detailed Description
In order to make the technical solutions of the present application better understood by those skilled in the art, the technical solutions in the embodiments of the present application will be clearly and completely described below in conjunction with the embodiments of the present application, and it is obvious that the described embodiments are only some embodiments of the present application, but not all embodiments.
Example 1
Adding RuCl3·xH2O and ZnSO4·7H2Preparing a mixed solution from O according to a certain proportion (the molar ratio is 2:1), stirring and dissolving the mixed solution by using an ethanol-water solution with a proper volume ratio (1:2) at room temperature, wherein the total volume of the ethanol-water solution is 6-10 times of that of the mixed solution, and forming a mixed system. And (3) dropwise adding a NaOH solution (0.2mol/L) into the ruthenium-zinc alcohol aqueous solution system at a certain speed (0.8ml/min), wherein the dropwise adding process is carried out at room temperature and a certain stirring speed (200r/min), and in order to fully react, stirring is carried out for a certain time after the feeding is finished. A black precipitate was obtained.
After the system was allowed to stand for 12 hours, the black precipitate was dropped to the bottom of the vessel, and the supernatant was poured off. Washing the precipitate with ionized water to neutrality, mixing with water-ionic liquid (1, 3-dimethyl imidazole tetrafluoroborate) mixture in certain volume ratio (1:1), and hydrogen reducing in a high pressure reactor.
Reducing for 6h at 160 ℃ and 3MPa of hydrogen pressure, stirring at 400r/min, reducing for 10 h, and leaching in a certain amount of 15% NaOH solution for 5 h at 70 ℃ after reduction. Then washed with water to neutral. And (5) performing suction filtration, and placing in a vacuum drier for later use. The label cat 1.
Example 2
Adding RuCl3·xH2O and ZnSO4·7H2Preparing a mixed solution from O according to a certain proportion (the molar ratio is 2:1), stirring and dissolving the mixed solution by using an ethanol-water solution with a proper volume ratio (1:2) at room temperature, wherein the total volume of the ethanol-water solution is 6-10 times of that of the mixed solution, and forming a mixed system. And (3) dropwise adding a NaOH solution (6mol/L) into the ruthenium-zinc alcohol aqueous solution system at a certain speed (0.1.2ml/min), wherein the dropwise adding process is carried out at room temperature and a certain stirring speed (250r/min), and in order to fully react, stirring is carried out for a certain time after the feeding is finished. A black precipitate was obtained.
After the system was allowed to stand for 12 hours, the black precipitate was dropped to the bottom of the vessel, and the supernatant was poured off. Washing the precipitate with ionized water to neutrality, mixing with water-ionic liquid (1, 3-dimethyl imidazole tetrafluoroborate) mixture in certain volume ratio (1:1), and hydrogen reducing in a high pressure reactor.
Reducing for 8 hours at 180 ℃ and 4MPa of hydrogen pressure, stirring at 500r/min, reducing for 10 hours, and leaching in a certain amount of 15 percent NaOH solution for 5 hours at 80 ℃ after reduction. Then washed with water to neutral. And (5) performing suction filtration, and placing in a vacuum drier for later use. The label cat 2.
Example 3
Adding RuCl3·xH2O and ZnSO4·7H2Preparing a mixed solution from O according to a certain proportion (the molar ratio is 2:1), stirring and dissolving the mixed solution by using an ethanol-water solution with a proper volume ratio (1:2) at room temperature, wherein the total volume of the ethanol-water solution is 6-10 times of that of the mixed solution, and forming a mixed system. Dropping NaOH solution (2mol/L) into the ruthenium zinc alcohol aqueous solution system at a certain speed (1.2ml/min), wherein the dropping process is carried out at room temperature and a certain stirring speed (200r/min), and in order to fully react, stirring is required after the feeding is finishedStirring for a certain time. A black precipitate was obtained.
After the system was allowed to stand for 12 hours, the black precipitate was dropped to the bottom of the vessel, and the supernatant was poured off. Washing the precipitate with ionized water to neutrality, mixing with water-ionic liquid (1, 3-dimethyl imidazole tetrafluoroborate) mixture in certain volume ratio (1:1), and hydrogen reducing in a high pressure reactor.
Reducing for 6h at 160 ℃ and 4MPa of hydrogen pressure, stirring at 500r/min, reducing for 10 h, leaching in a certain amount of 15% NaOH solution for 5 h at 80 ℃ after reduction. Then washed with water to neutral. And (5) performing suction filtration, and placing in a vacuum drier for later use. The label cat 3.
Example 4
Adding RuCl3·xH2O and ZnSO4·7H2Preparing a mixed solution from O according to a certain proportion (the molar ratio is 2:1), stirring and dissolving the mixed solution by using an ethanol-water solution with a proper volume ratio (1:2) at room temperature, wherein the total volume of the ethanol-water solution is 6-10 times of that of the mixed solution, and forming a mixed system. And (3) dropwise adding a NaOH solution (2mol/L) into the ruthenium-zinc alcohol aqueous solution system at a certain speed (1.2ml/min), wherein the dropwise adding process is carried out at room temperature and a certain stirring speed (200r/min), and in order to fully react, stirring is carried out for a certain time after the feeding is finished. A black precipitate was obtained.
After the system was allowed to stand for 12 hours, the black precipitate was dropped to the bottom of the vessel, and the supernatant was poured off. Washing the precipitate with ionized water to neutrality, mixing with water-ionic liquid (1, 3-dimethyl imidazole tetrafluoroborate) mixture in certain volume ratio (1:1), and hydrogen reducing in a high pressure reactor.
Reducing at 60 deg.C and 4MPa for 2h, at 100 deg.C and 4MPa for 2h, at 160 deg.C and 4MPa for 2h, stirring at 500r/min for 10 h, and leaching in 15% NaOH solution at 80 deg.C for 5 h. Then washed with water to neutral. And (5) performing suction filtration, and placing in a vacuum drier for later use. The label cat 4.
Example 5
2g of the catalysts (cat1, cat2, cat3 and cat4) in the examples, 200mL of deionized water and 45g of dimethyl carbonate are respectively added into a reaction kettle, the temperature is slowly increased to 160 ℃ at the stirring speed of 400r/min, 100mL of preheated uric acid is added into the reaction kettle, the stirring speed is increased to 1200r/min, the reaction is started, samples are taken at different time intervals, and the organic phase composition is analyzed by gas chromatography. And calculating the relative content of substances in the organic phase by a corrected area normalization method, then obtaining the conversion rate of the uric acid and the selectivity of the tetramethyluric acid under different times of reaction, and calculating the yield data of the tetramethyluric acid.
The results are shown in the following table
| Catalyst and process for preparing same | Conversion rate | Selectivity is | Yield of | |
| Example 1 | cat1 | 82.6％ | 88.9％ | 73.4％ |
| Example 2 | cat2 | 82.3％ | 91.2％ | 75.1％ |
| Example 3 | cat3 | 81.9％ | 94.5％ | 77.4％ |
| Example 4 | cat4 | 88.0％ | 93.6％ | 82.4％ |
It can be seen from the above examples that the method provided by the present invention can synthesize tetramethyluric acid under normal pressure.
Furthermore, it can be seen that the reduction process has a greater effect on the conversion of the catalyst and a lesser effect on the selectivity.
The above description is only exemplary, preferred and exemplary of the present application, and is not intended to limit the present application.
Claims (10)
1. A synthetic method of tetramethyluric acid is characterized in that the synthetic process is shown as the following formula:
2. the method for synthesizing tetramethyluric acid according to claim 1, wherein the conditions of the synthesis reaction are as follows: under the action of a catalyst, the temperature is 160-180 ℃, the pressure is normal pressure, and the reaction time is 3-4 hours.
3. The method for synthesizing tetramethyluric acid according to claim 2, wherein the dimethyl carbonate, the ionized water and the catalyst are added into a reaction kettle, stirred and heated to 160 ℃, the preheated uric acid is added into the reaction kettle, and the stirring speed is increased to start the reaction; the catalyst is a ruthenium-containing catalyst.
4. The method for synthesizing tetramethyluric acid according to claim 2, wherein the stirring speed is 400r/min before adding uric acid and 1200r/min after adding uric acid.
5. The method for synthesizing tetramethyluric acid according to claim 2, wherein the ruthenium-containing catalyst is obtained by the following method: mixing a hydrate of ruthenium trichloride and a hydrate of zinc sulfate, adding an ethanol-water solution, and stirring at room temperature to form a ruthenium-zinc-alcohol mixed system; dropwise adding a sodium hydroxide solution into the ruthenium-zinc-alcohol mixed system to obtain black precipitates, washing, adding a water-ionic liquid mixture, reducing in a sealed container by using hydrogen, leaching in the sodium hydroxide solution at 70-80 ℃ after reduction, washing to be neutral, and vacuum drying to obtain the ruthenium-zinc-alcohol mixed catalyst.
6. The method for synthesizing tetramethyluric acid according to claim 5, wherein the dropping of sodium hydroxide is carried out under continuous stirring at a speed of 200-250 r/min, at a speed of 0.8-1.2 ml/min and at a concentration of 0.2-5 mol/L; and in order to fully react, the mixture needs to be stirred for a certain time after the feeding is finished.
7. The method for synthesizing tetramethyluric acid according to claim 5, wherein the water-ionic liquid mixture is a mixture of water and 1, 3-dimethylimidazolium tetrafluoroborate, and the volume ratio is 1.2: 1.
8. The method for synthesizing tetramethyluric acid according to claim 5, wherein the reducing conditions are as follows: reducing for 6-8 h at 160-180 ℃ and 3-4 MPa of hydrogen pressure, and stirring at 400-500 r/min.
9. The method for synthesizing tetramethyluric acid according to claim 5, wherein the reducing conditions are as follows: reducing at 60 ℃ and 4MPa for 2h, at 100 ℃ and 4MPa for 2h, and at 160 ℃ and 4MPa for 2h, with the stirring speed of 400-500 r/min.
10. The catalyst special for synthesizing tetramethyl urea is characterized by being obtained by the following method: mixing a hydrate of ruthenium trichloride and a hydrate of zinc sulfate, adding an ethanol-water solution, and stirring at room temperature to form a ruthenium-zinc-alcohol mixed system; dropwise adding a sodium hydroxide solution into the ruthenium-zinc-alcohol mixed system to obtain black precipitates, washing, adding a water-ionic liquid mixture, reducing in a sealed container by using hydrogen, leaching in the sodium hydroxide solution at 70-80 ℃ after reduction, washing to be neutral, and vacuum drying to obtain the ruthenium-zinc-alcohol mixed catalyst.
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