CN108126694B - Platinum-carbon catalyst for azithromycin production and preparation method thereof - Google Patents
Platinum-carbon catalyst for azithromycin production and preparation method thereof Download PDFInfo
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Abstract
A platinum-carbon catalyst for azithromycin production comprises platinum and activated carbon, wherein the mass fraction of the platinum is 3% by taking the weight of the activated carbon as a reference; the preparation method comprises the following steps: step 1) dipping activated carbon by adopting a phosphorus-containing compound, then drying, and roasting for 2h at the temperature of 450-550 ℃ in a nitrogen atmosphere; step 2) preparing 10-20g/L chloroplatinic acid solution; and 3) introducing a chloroplatinic acid solution into the activated carbon, performing excessive impregnation for 2-4h under the conditions of the temperature of 70-90 ℃ and the pressure of 3-5MPa, drying, and introducing a mixed gas of hydrogen and nitrogen for reduction for 2h under the temperature of 250-300 ℃. The activity and the application times of the platinum-carbon catalyst can be greatly improved, and the anti-poisoning performance of the platinum-carbon catalyst is improved.
Description
Technical Field
The invention belongs to the technical field of precious metal catalyst preparation, and particularly relates to a platinum-carbon catalyst for azithromycin production and a preparation method thereof.
Background
Azithromycin is one of the improved macrolide derivatives, is a macrolide broad-spectrum antibiotic obtained by modifying an erythromycin structure, and achieves an antibacterial effect by mainly combining with a bacterial 50S ribosome subunit and blocking peptide displacement to prevent the synthesis of bacterial polypeptide. The existing azithromycin is produced by that erythromycin oxime is subjected to Beckmann rearrangement reaction to obtain erythromycin 6, 9-imine ether, and then is reduced by using sodium borohydride or potassium borohydride as a reducing agent or is subjected to pressure hydrogenation reduction by using noble metal as a catalyst. In the case of pressure hydrogenation reduction using a noble metal, a platinum carbon or rhodium carbon catalyst is mainly used, and in actual production, hydrogenation reduction is generally performed using a platinum carbon catalyst in consideration of cost. However, when the platinum-carbon catalyst is used for hydrogenation reduction, the catalyst is easily poisoned, the activity is reduced, the selectivity is poor and the like, so that the catalyst is used for too low times and the production cost is too high. Therefore, how to reduce the anti-poisoning performance of the platinum-carbon catalyst and improve the activity and the application frequency of the platinum-carbon catalyst becomes one of the difficult problems of research in the azithromycin preparation process.
Since platinum-carbon catalysts usually use a single active component, the research on the improvement of platinum-carbon catalysts has been focused on the structure of the carrier and the distribution of platinum metal on the carrier, which indeed has a great influence on the performance of the catalyst. Since the catalytic reaction is carried out on the surface of the platinum particles, the higher the dispersion degree of platinum, the higher the activity of the catalyst, and the longer the service life. At present, powdered activated carbon is mainly used as a carrier of the platinum-carbon catalyst, the platinum-carbon catalyst has poor adsorptivity to platinum particles, the acting force between the platinum particles and the activated carbon carrier is weak, metal falling easily occurs in the recycling process, and the service life is short.
At present, the preparation of the platinum-carbon catalyst mainly comprises the traditional methods such as an impregnation method, a precipitation method, a colloidal solution method and the like, but the prepared catalyst has the advantages of wide active component particle range, large particle size, uneven distribution, low dispersion degree and difficulty in preparing the platinum-carbon catalyst with high selectivity, high activity and long service life. For example, in the process of preparing the platinum-carbon catalyst by the impregnation method, platinum crystal nuclei grow and agglomerate in a liquid phase or on the surface of a carrier, and the prepared catalyst has the advantages of wide active component particle range, large particle size and low platinum dispersion degree, so that the platinum-carbon catalyst with high activity and long service life is difficult to prepare. The platinum-carbon catalyst prepared by the colloidal solution method has the advantages that most active components are exposed and deposited on the surface of the carrier carbon, the problem that the nano platinum serving as the active component is firmly attached to the carrier carbon cannot be solved, the activity of the catalyst is high in the initial stage in the catalytic reaction, but the activity is rapidly reduced in the later stage of the catalysis, the repeated application times are few, and the service life is short.
Disclosure of Invention
The invention provides a platinum-carbon catalyst for azithromycin production and a preparation method thereof, which mainly solve the technical problems that: firstly, powdered activated carbon used as a carrier in the existing platinum-carbon catalyst has poor adsorptivity to platinum particles, the acting force between the platinum particles and the activated carbon carrier is weak, and metal falling is easy to occur in the recycling process, so that the service life is short; secondly, the platinum-carbon catalyst prepared by the conventional method has the advantages of wide active component particle range, large particle size, uneven distribution and low dispersity, and is difficult to prepare the platinum-carbon catalyst with high selectivity, high activity and long service life.
In order to solve the technical problem, the invention provides a platinum-carbon catalyst for azithromycin production, which consists of active metal and a carrier, wherein the active metal is platinum, the carrier is phosphorus-modified active carbon, and the mass fraction of the platinum is 2-4% by taking the weight of the active carbon as a reference.
Preferably: the mass fraction of the platinum is 3% based on the weight of the activated carbon.
The invention provides a preparation method of a platinum-carbon catalyst for azithromycin production, which comprises the following steps:
step 1) preparing phosphorus modified activated carbon, carrying out excessive impregnation on the activated carbon for 4-8h by adopting a phosphorus compound with the mass fraction of 5% at normal temperature, then evaporating to dryness, drying, and introducing nitrogen for roasting for 2h at the temperature of 500 ℃;
step 2) preparing a platinum precursor solution, weighing chloroplatinic acid, adding deionized water to dilute to 10-20g/L, and adjusting the pH of the solution to 2 by using sodium hydroxide under stirring to prepare the chloroplatinic acid precursor solution, namely the chloroplatinic acid solution;
step 3) loading platinum, namely adding the prepared platinic acid solution in the step 2) into an impregnation reactor, then adding the phosphorus modified activated carbon obtained in the step 1), stirring and mixing uniformly, heating the reactor to 80 ℃, then applying pressure to the impregnation reactor to 3-5Mpa, and keeping the pressure for 2 hours;
step 4) reduction of platinum, namely evaporating the impregnation liquid in the step 3) to dryness, then drying for 8H at the temperature of 105 ℃, then heating to 250-300 ℃, and introducing H2-N2Reducing the mixed gas for 2H, wherein H is2-N2The volume fraction of hydrogen in the mixed gas is 5 percent, and the platinum carbon catalyst for producing the azithromycin is obtained.
Preferably: the phosphorus-containing compound is any one or a mixture of any two of sodium phosphate, sodium tripolyphosphate, sodium metaphosphate and sodium pyrophosphate in any proportion.
Compared with the prior art, the invention has the following advantages:
1. compared with the traditional platinum carbon catalyst, the platinum carbon catalyst for azithromycin production has the advantages that as the activated carbon is modified by the phosphorus compound, the activated carbon has larger pore diameter, which is beneficial to the impregnation of the active component, and meanwhile, the phosphorus compound is arranged on the carrier, which is more beneficial to the adsorption of the metal platinum active component on the surface of the activated carbon;
2. the preparation method of the platinum-carbon catalyst for azithromycin production adopts a pressure impregnation method, solves the defect that platinum is difficult to be adsorbed by active carbon or is slowly adsorbed, and simultaneously leads a proper amount of platinum metal to enter the interior of the active carbon through the change of pressure, thereby improving the conversion of reactants in the hydrogenation process;
3. the catalyst is suitable for hydrogenation of erythromycin 6, 9-imino ether in azithromycin production, can ensure that the platinum carbon catalyst has high activity and long service life and can be repeatedly used, and improves the anti-poisoning performance of the platinum carbon catalyst.
Detailed Description
The platinum-carbon catalyst for producing azithromycin and the preparation method thereof provided by the present invention will be further described with reference to the preferred embodiments.
Example 1, a method for preparing a platinum-carbon catalyst for azithromycin production, the steps of which are specifically as follows.
Step 1) pretreating activated carbon (preparing phosphorus modified activated carbon), taking 10g of activated carbon at normal temperature, adding 10g of activated carbon into a sodium phosphate solution with the mass fraction of 5%, excessively soaking for 4-8h, then evaporating the soaking solution to dryness, drying at 105 ℃, introducing nitrogen at 500 ℃ and roasting for 2 h;
step 2) preparing a platinum precursor solution (preparing a chloroplatinic acid solution), weighing 0.83g of chloroplatinic acid crystal, adding deionized water to dilute to 50mL, and adjusting the pH of the solution to 2 by using sodium hydroxide under the stirring condition to prepare the chloroplatinic acid precursor solution;
step 3) loading platinum, namely adding the prepared platinic acid solution in the step 2) into an impregnation reactor, then adding the phosphorus modified activated carbon obtained in the step 1), stirring and mixing uniformly, heating the reactor to 70 ℃, then applying pressure to 3Mpa in the impregnation reactor, and keeping the pressure for 2 hours;
step 4) reduction of platinum, evaporating the impregnation liquid in the step 3) to dryness, then drying for 8H at the temperature of 105 ℃, and then H2-N2Heating to 250-300 ℃ in mixed gas atmosphere for reduction for 2H, wherein H is2-N2The volume fraction of hydrogen in the mixed gas is 5 percent, and the platinum carbon catalyst for producing the azithromycin is obtained.
Embodiment 2, a method for preparing a platinum-carbon catalyst for azithromycin production, the steps of which are specifically as follows.
Step 1) pretreating activated carbon (preparing phosphorus modified activated carbon), taking 10g of activated carbon at normal temperature, adding 10g of activated carbon into a sodium tripolyphosphate solution with the mass fraction of 5% for excessive impregnation for 4-8h, then evaporating the impregnation solution to dryness, drying at 105 ℃, introducing nitrogen at 500 ℃ for roasting for 2 h;
step 2) preparing a platinum precursor solution (preparing a chloroplatinic acid solution), weighing 0.83g of chloroplatinic acid crystal, adding deionized water to dilute to 50mL, and adjusting the pH of the solution to 2 by using sodium hydroxide under the stirring condition to prepare the chloroplatinic acid precursor solution;
step 3) loading platinum, namely adding the prepared platinic acid solution in the step 2) into an impregnation reactor, then adding the phosphorus modified activated carbon obtained in the step 1), stirring and mixing uniformly, heating the reactor to 80 ℃, then applying pressure to 3Mpa in the impregnation reactor, and keeping the pressure for 2 hours;
step 4) reduction of platinum, evaporating the impregnation liquid in the step 3) to dryness, then drying for 8H at the temperature of 105 ℃, and then H2-N2Heating to 250-300 ℃ in mixed gas atmosphere for reduction for 2H, wherein H is2-N2The volume fraction of hydrogen in the mixed gas is 5 percent, and the platinum carbon catalyst for producing the azithromycin is obtained.
Example 3, a method for preparing a platinum-carbon catalyst for azithromycin production, the steps of which are specifically as follows.
Step 1) pretreating activated carbon (preparing phosphorus modified activated carbon), taking 10g of activated carbon at normal temperature, adding 10g of activated carbon into a sodium phosphate solution with the mass fraction of 5%, excessively soaking for 4-8h, then evaporating the soaking solution to dryness, drying at 105 ℃, introducing nitrogen at 500 ℃ and roasting for 2 h;
step 2) preparing a platinum precursor solution (preparing a chloroplatinic acid solution), weighing 0.83g of chloroplatinic acid crystal, adding deionized water to dilute to 50mL, and adjusting the pH of the solution to 2 by using sodium hydroxide under the stirring condition to prepare the chloroplatinic acid precursor solution;
step 3) loading platinum, namely adding the prepared platinic acid solution in the step 2) into an impregnation reactor, then adding the phosphorus modified activated carbon obtained in the step 1), stirring and mixing uniformly, heating the reactor to 80 ℃, then applying pressure to 4Mpa in the impregnation reactor, and keeping the pressure for 2 hours;
step 4) reduction of platinum, evaporating the impregnation liquid in the step 3) to dryness, then drying for 8H at the temperature of 105 ℃, and then H2-N2Heating to 250-300 ℃ in mixed gas atmosphere for reduction for 2H, wherein H is2-N2The volume fraction of hydrogen in the mixed gas is 5 percent, and the platinum carbon catalyst for producing the azithromycin is obtained.
Embodiment 4, a method for preparing a platinum carbon catalyst for azithromycin production, the steps of which are as follows.
Step 1) pretreating activated carbon (preparing phosphorus modified activated carbon), taking 10g of activated carbon at normal temperature, adding 10g of activated carbon into a sodium phosphate solution with the mass fraction of 5%, excessively soaking for 4-8h, then evaporating the soaking solution to dryness, drying at 105 ℃, introducing nitrogen at 500 ℃ and roasting for 2 h;
step 2) preparing a platinum precursor solution (preparing a chloroplatinic acid solution), weighing 0.83g of chloroplatinic acid crystal, adding deionized water to dilute to 50mL, and adjusting the pH of the solution to 2 by using sodium hydroxide under the stirring condition to prepare the chloroplatinic acid precursor solution;
step 3) loading platinum, namely adding the prepared platinic acid solution in the step 2) into an impregnation reactor, then adding the phosphorus modified activated carbon obtained in the step 1), stirring and mixing uniformly, heating the reactor to 80 ℃, then applying pressure to the impregnation reactor to 5Mpa, and keeping the pressure for 2 hours;
step 4) reduction of platinum, evaporating the impregnation liquid in the step 3) to dryness, then drying for 8H at the temperature of 105 ℃, and then H2-N2Heating to 250-300 ℃ in mixed gas atmosphere for reduction for 2H, wherein H is2-N2The volume fraction of hydrogen in the mixed gas is 5 percent, and the platinum carbon catalyst for producing the azithromycin is obtained.
Example 5, a method for preparing a platinum carbon catalyst for azithromycin production, the steps of which are specifically as follows.
Step 1) pretreating activated carbon (preparing phosphorus modified activated carbon), taking 10g of activated carbon at normal temperature, adding 10g of activated carbon into a sodium phosphate and sodium metaphosphate solution with the mass fraction of 5%, excessively soaking for 4-8h, then evaporating the soaking solution to dryness, drying at the temperature of 105 ℃, introducing nitrogen at the temperature of 500 ℃ and roasting for 2 h;
step 2) preparing a platinum precursor solution (preparing a chloroplatinic acid solution), weighing 0.83g of chloroplatinic acid crystal, adding deionized water to dilute to 50mL, and adjusting the pH of the solution to 2 by using sodium hydroxide under the stirring condition to prepare the chloroplatinic acid precursor solution;
step 3) loading platinum, namely adding the prepared platinic acid solution in the step 2) into an impregnation reactor, then adding the phosphorus modified activated carbon obtained in the step 1), stirring and mixing uniformly, heating the reactor to 80 ℃, then applying pressure to 4Mpa in the impregnation reactor, and keeping the pressure for 2 hours;
step 4) reduction of platinum, evaporating the impregnation liquid in the step 3) to dryness, then drying for 8H at the temperature of 105 ℃, and then H2-N2Heating to 250-300 ℃ in mixed gas atmosphere for reduction for 2H, wherein H is2-N2The volume fraction of hydrogen in the mixed gas is 5 percent, and the platinum carbon catalyst for producing the azithromycin is obtained.
The activity of the conventional platinum carbon and the catalysts of examples 1 to 5 was evaluated by using them in azithromycin production by a specific method: dissolving 6, 9-imino ether with a certain mass in methanol, placing the methanol in a high-pressure kettle, adding a certain mass of 3% platinum-carbon catalyst, after nitrogen displacement for three times, introducing hydrogen, stopping reaction when hydrogen pressure is unchanged, filtering and separating the catalyst, adjusting certain pH of filtrate with alkali, filtering and drying the product to obtain the dihydrohomoerythromycin, and simultaneously detecting the purity of the dihydrohomoerythromycin with a liquid phase.
TABLE 1 results of the catalyst in the hydrogenation of 6,9 imine ethers
From the results in table 1, the activity of the platinum carbon catalyst prepared by the invention is sometimes remarkably improved in conversion rate and selectivity compared with the activity of the conventional platinum carbon, and meanwhile, the conventional platinum carbon is mechanically used for experiments with the two catalysts in example 3, the yield of the conventional platinum carbon is reduced by 5% after being mechanically used for about 10 times, and the yield of the conventional platinum carbon is reduced by 3% after the platinum carbon is mechanically used for 50 times, so that the results further illustrate that the catalyst can be repeatedly used for multiple times.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and all simple modifications, changes and equivalent structural changes made to the above embodiment according to the technical spirit of the present invention still fall within the protection scope of the technical solution of the present invention.
Claims (6)
1. An application of a platinum carbon catalyst in azithromycin production, wherein the platinum carbon catalyst comprises active metal and a carrier, and is characterized in that: the active metal is platinum, the carrier is phosphorus modified active carbon prepared by dipping the active carbon by adopting a phosphorus-containing compound, drying and then roasting for 1.8-2.2h by introducing nitrogen at the temperature of 450-550 ℃, the phosphorus-containing compound is any one or any mixture of any two of sodium phosphate, sodium tripolyphosphate, sodium metaphosphate and sodium pyrophosphate, and the mass fraction of the platinum is 2-4% by taking the weight of the active carbon as a reference.
2. The use of a platinum carbon catalyst in azithromycin production as claimed in claim 1, wherein: the mass fraction of the platinum is 3% based on the weight of the activated carbon.
3. The application of the platinum-carbon catalyst in the production of azithromycin according to claim 1 or 2, characterized in that the preparation method of the platinum-carbon catalyst comprises the following steps:
step 1) preparing phosphorus modified activated carbon, dipping the activated carbon by adopting a phosphorus-containing compound, wherein the phosphorus-containing compound is any one or a mixture of any two of sodium phosphate, sodium tripolyphosphate, sodium metaphosphate and sodium pyrophosphate in any proportion, then drying, and introducing nitrogen to roast for 1.8-2.2h at the temperature of 450-550 ℃;
step 2) preparing a chloroplatinic acid solution, taking chloroplatinic acid, and adding deionized water to dilute to 10-20 g/L;
and 3) introducing the chloroplatinic acid solution prepared in the step 2) into the activated carbon obtained in the step 1), carrying out excessive impregnation at the temperature of 70-90 ℃ and the pressure of 3-5MPa, keeping for 2-4h, drying, introducing a mixed gas of hydrogen and nitrogen at the temperature of 300 ℃ of 250-fold, wherein the volume fraction of the hydrogen in the mixed gas is 5%, and reducing for 1.8-2.2h to obtain the platinum-carbon catalyst for azithromycin production.
4. The use of a platinum carbon catalyst in azithromycin production as claimed in claim 3, wherein: in the step 1), the activated carbon is excessively impregnated for 4-8h by adopting a phosphorus-containing compound with the mass fraction of 5%, then is dried, and is roasted for 2h by introducing nitrogen at the temperature of 500 ℃.
5. The use of a platinum carbon catalyst in azithromycin production as claimed in claim 4, wherein: in the step 2), after dissolving the chloroplatinic acid, adjusting the pH of the solution to 2 by using sodium hydroxide.
6. The use of a platinum carbon catalyst in azithromycin production as claimed in claim 5, wherein: in the step 3), after dipping for 2-4h, the dipping solution is evaporated to dryness and then dried for 8h at the temperature of 105 ℃.
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| US4131721A (en) * | 1977-06-17 | 1978-12-26 | Electric Power Research Institute, Inc. | Electrolytic cell having a novel electrode including platinum on a carbon support activated with a phosphorus-oxygen-containing compound |
| US4375550A (en) * | 1979-02-22 | 1983-03-01 | Johnson, Matthey & Co., Limited | Hydrogenation of halogen-substituted aromatic nitro compounds |
| CN104084194A (en) * | 2014-07-08 | 2014-10-08 | 郴州高鑫材料有限公司 | Method for preparing high-selectivity platinum-carbon catalyst through vacuum impregnation |
| CN106693961A (en) * | 2017-01-10 | 2017-05-24 | 江西省汉氏贵金属有限公司 | Palladium-carbon catalyst and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4131721A (en) * | 1977-06-17 | 1978-12-26 | Electric Power Research Institute, Inc. | Electrolytic cell having a novel electrode including platinum on a carbon support activated with a phosphorus-oxygen-containing compound |
| US4375550A (en) * | 1979-02-22 | 1983-03-01 | Johnson, Matthey & Co., Limited | Hydrogenation of halogen-substituted aromatic nitro compounds |
| CN104084194A (en) * | 2014-07-08 | 2014-10-08 | 郴州高鑫材料有限公司 | Method for preparing high-selectivity platinum-carbon catalyst through vacuum impregnation |
| CN106693961A (en) * | 2017-01-10 | 2017-05-24 | 江西省汉氏贵金属有限公司 | Palladium-carbon catalyst and preparation method and application thereof |
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