CN116574040A - Preparation method for efficiently recycling thiamphenicol amine - Google Patents
Preparation method for efficiently recycling thiamphenicol amine Download PDFInfo
- Publication number
- CN116574040A CN116574040A CN202310548861.2A CN202310548861A CN116574040A CN 116574040 A CN116574040 A CN 116574040A CN 202310548861 A CN202310548861 A CN 202310548861A CN 116574040 A CN116574040 A CN 116574040A
- Authority
- CN
- China
- Prior art keywords
- thiamphenicol
- amine
- florfenicol
- liquid alkali
- regulating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- CIAZEFCFQFQJLB-NXEZZACHSA-N (1r,2r)-2-amino-1-(4-methylsulfonylphenyl)propane-1,3-diol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@H](N)CO)C=C1 CIAZEFCFQFQJLB-NXEZZACHSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000004064 recycling Methods 0.000 title description 10
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 claims abstract description 38
- 229960003760 florfenicol Drugs 0.000 claims abstract description 38
- 238000003756 stirring Methods 0.000 claims abstract description 34
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 239000003513 alkali Substances 0.000 claims abstract description 22
- 229960003053 thiamphenicol Drugs 0.000 claims abstract description 22
- OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 claims abstract description 22
- 230000001105 regulatory effect Effects 0.000 claims abstract description 18
- 239000000047 product Substances 0.000 claims abstract description 12
- XLSYLQDVLAXIKK-NXEZZACHSA-N (1r,2s)-2-amino-3-fluoro-1-(4-methylsulfonylphenyl)propan-1-ol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@H](N)CF)C=C1 XLSYLQDVLAXIKK-NXEZZACHSA-N 0.000 claims abstract description 10
- 239000012452 mother liquor Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims description 32
- 238000006460 hydrolysis reaction Methods 0.000 claims description 24
- 239000012043 crude product Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 239000010413 mother solution Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003651 drinking water Substances 0.000 claims description 5
- 235000020188 drinking water Nutrition 0.000 claims description 5
- 238000004321 preservation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 abstract description 8
- 238000011084 recovery Methods 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 description 18
- 239000000463 material Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
Abstract
The invention discloses a preparation method for efficiently recovering thiamphenicol amine, which comprises the steps of adding liquid alkali into florfenicol mother liquor containing florfenicol, thiamphenicol and florfenicol amine, regulating the pH to 13-14, heating a system to 80 ℃ after stirring for a period of time, keeping the temperature for a period of time, regulating the pH of the system to 13-14 by using the liquid alkali, continuing to keep the temperature for a period of time, regulating the pH of the system to 6.5-8 by using the liquid alkali, evaporating and recovering alcohol and water to obtain a crude thiamphenicol amine product, and purifying to obtain a refined thiamphenicol amine product. The invention has the advantages of simplicity, easy operation and low recovery cost, realizes the recovery and utilization of byproducts, and reduces the consumption of the byproducts.
Description
Technical Field
The invention relates to the technical field of compound recovery, in particular to a preparation method for efficiently recovering thiamphenicol amine.
Background
Florfenicol is a fluorinated derivative of the antibiotics chloramphenicol and thiamphenicol, has inhibitory effect on a number of bacteria, and is useful for treating or preventing bacterial infectious diseases in animals such as cattle and fish. The current production process route of the florfenicol is more consistent, D-p-methylsulfonyl phenylserine ethyl ester is used as a raw material, a florfenicol crude product is prepared after reduction reaction, cyclization reaction, fluorination reaction and hydrolysis reaction, and then the refined florfenicol is obtained after dissolution and recrystallization treatment; however, thiamphenicol and florfenicol amine byproducts are generated in the reaction process, a small amount of florfenicol is remained in the mother solution remained after the florfenicol crude product is separated after the hydrolysis reaction, and thiamphenicol and florfenicol amine byproducts are remained.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, and provides a preparation method for efficiently recycling thiamphenicol amine, which is simple, easy to operate and low in recycling cost, realizes recycling of byproducts and reduces consumption of the byproducts.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a method for preparing thiamphenicol amine with high efficiency comprises the steps of adding liquid alkali into a florfenicol mother solution containing florfenicol, thiamphenicol and florfenicol amine, regulating the pH to 13-14, heating the system to 80 ℃ after stirring for a period of time, keeping the temperature for a period of time, regulating the pH of the system to 13-14 by using the liquid alkali, keeping the temperature for a period of time, regulating the pH of the system to 6.5-8 by using the liquid alkali, evaporating and recovering alcohol and water to obtain a coarse thiamphenicol amine product, and purifying to obtain a refined thiamphenicol amine product.
The florfenicol mother solution is the mother solution which is remained after the florfenicol crude product is separated after the hydrolysis reaction in the production of the synthetic florfenicol.
Adding liquid alkali into the florfenicol mother solution, adjusting the pH value to 13-14, and stirring for 30min.
The temperature is raised to 80 ℃ and then the heat preservation time is 1-2h.
And then adjusting the pH value of the system to 13-14 by liquid alkali, and then continuing to keep the temperature for 2 hours.
The purification treatment of the thiamphenicol crude product comprises the following steps: dissolving the thiamphenicol crude product in drinking water, cooling to-5 to 0 ℃ and crystallizing.
The beneficial effects of the invention are as follows: the florfenicol, thiamphenicol and florfenicol amine in the florfenicol mother liquor containing florfenicol, thiamphenicol and florfenicol amine are converted into thiamphenicol amine for recycling through an alkaline hydrolysis method, so that the florfenicol is prepared (the flow is shown in the figure 2), the recycling method is simple and easy to operate, the recycling cost is low, recycling of byproducts is realized, the consumption of the byproducts is reduced, and the requirements of green preparation and production are met.
Drawings
FIG. 1 is a schematic diagram of a process for the recovery of thiamphenicol amine of the present invention;
FIG. 2 is a schematic diagram of a flow chart for preparing florfenicol from thiamphenicol;
FIG. 3 is a block diagram of a hydrolysis kettle according to the present invention;
FIG. 4 is an enlarged view of FIG. 3 at A;
fig. 5 is an enlarged view at B in fig. 3.
In the figure: the kettle body 1, the through hole 11, the jacket 2, the cooling cylinder 3, the inner cylinder 31, the outer cylinder 32, the top cylinder 33, the guide rail 34, the upper slide rail 35, the outer slide rail 36, the first stirring paddle 4, the first shaft portion 41, the second shaft portion 42, the third shaft portion 43, the first blade 44, the connecting disc 45, the second stirring paddle 5, the second blade 51, the push plate 6, the through pipe 7 and the motor 8.
Detailed Description
The invention is further described with reference to the drawings and detailed description which follow:
example 1
Adding liquid alkali into 500g of florfenicol mother liquor containing florfenicol, thiamphenicol and florfenicol amine (mother liquor which is remained after separation of florfenicol crude product in production of synthetic florfenicol after hydrolysis reaction), regulating pH to 13, heating a system to 80 ℃ after stirring for 30min, preserving heat for 2h, regulating pH to 13 with liquid alkali, preserving heat for 2h continuously, regulating pH to 7 with liquid alkali, and evaporating and recovering alcohol and water to obtain a crude product of thiamphenicol amine; dissolving the thiamphenicol crude product in drinking water, cooling to-5 to 0 ℃ for crystallization, and filtering to obtain 10.2g of thiamphenicol refined product.
Example 2
Adding liquid alkali into 500g of florfenicol mother liquor containing florfenicol, thiamphenicol and florfenicol amine (mother liquor which is remained after separation of florfenicol crude product in production of synthetic florfenicol after hydrolysis reaction), regulating pH to 14, heating a system to 80 ℃ after stirring for 30min, preserving heat for 1h, regulating pH to 14 with liquid alkali, preserving heat for 2h continuously, regulating pH to 8 with liquid alkali, and evaporating and recovering alcohol and water to obtain a crude product of thiamphenicol amine; dissolving the thiamphenicol crude product in drinking water, cooling to-5 to 0 ℃ for crystallization, and filtering to obtain 10.51g of thiamphenicol refined product.
Example 3
Adding liquid alkali into 500g of florfenicol mother liquor containing florfenicol, thiamphenicol and florfenicol amine (mother liquor which is remained after separation of florfenicol crude product in production of synthetic florfenicol), regulating pH to 13, stirring for 30min, heating the system to 80 ℃, preserving heat for 1.5h, regulating pH to 134 with liquid alkali, preserving heat for 2h, regulating pH to 6.5 with liquid alkali, and evaporating to recover alcohol and water to obtain a crude product of thiamphenicol amine; dissolving the thiamphenicol crude product in drinking water, cooling to-5 to 0 ℃ for crystallization, and filtering to obtain 9.84g of thiamphenicol refined product.
Examples 4 to 6
The recovery preparation of thiamphenicol amine was carried out as in example 1 and using a modified hydrolysis tank, respectively.
The hydrolysis kettle is an important device for recycling thiamphenicol amine, in the prior art, the hydrolysis kettle usually adopts a single horizontal rotating stirring paddle to carry out hydrolysis, the stirring effect is not ideal, the hydrolysis effect is influenced, and the organic matter contained in the florfenicol mother liquor is easy to sink at the bottom of the hydrolysis kettle, so that the bottom material cannot fully participate in hydrolysis, the hydrolysis efficiency and effect are also influenced, and the yield and quality of a product are influenced.
As shown in fig. 3-5, the hydrolysis kettle is improved according to the invention, the hydrolysis kettle comprises a kettle body 1, a jacket 2 sleeved outside the kettle body 1, a hollow cooling cylinder 3 fixedly arranged in the kettle body 1 and a stirring mechanism arranged in the kettle body 1, wherein the kettle body 1 and the jacket 2 enclose a closed cavity and are used for introducing cooling water or steam, the lower end of the cooling cylinder 3 is fixedly connected with the inner wall of the bottom of the kettle body 1, the inner cavity of the cooling cylinder 3 is communicated with the inner cavity of the jacket 2, a plurality of transverse through pipes 7 penetrate through the lower part of the cooling cylinder 3, the stirring mechanism comprises a first stirring paddle 4 which stretches into the inner ring of the cooling cylinder 3 and a plurality of second stirring paddles 5 distributed on the outer ring of the cooling cylinder 3, the first stirring paddles 4 rotate to drive one ring of the second stirring paddles 5, a push plate 6 which is driven to lift by the first stirring paddles 4 is embedded in the cooling cylinder 3, and the peripheral edge of the push plate 6 is adhered to the annular inner wall of the cooling cylinder 3.
The cooling cylinder 3 comprises an inner cylinder 31 and an outer cylinder 32 which are concentrically arranged on the inner ring and the outer ring, and a top cylinder 33 which is used for connecting the upper end of the inner cylinder 31 with the upper end of the outer cylinder 32, wherein the lower end of the inner cylinder 31 and the lower end of the outer cylinder 32 are fixedly connected with the bottom of the kettle body 1, the inner cylinder 31, the outer cylinder 32, the top cylinder 33 and the inner wall of the bottom of the kettle body 1 form a cavity, and the inner cavity of the cooling cylinder 3 is communicated with the inner cavity of the jacket 2 through a plurality of through holes 11 formed in the bottom of the kettle body 1. The plurality of through holes 11 are circumferentially distributed.
The plurality of transverse through pipes 7 are circumferentially distributed, and the through pipes 7 penetrate through the inner cylinder 31 and the outer cylinder 32.
The first stirring paddle 4 is driven to rotate forward and backward by a motor 8. The first stirring paddle 4 comprises a first shaft portion 41, a second shaft portion 42 and a third shaft portion 43 which are vertically connected, the second shaft portion 42 and the third shaft portion 43 are located in the inner ring of the inner cylinder portion 31, the second shaft portion 42 is of a screw rod structure, the push plate 6 is in threaded connection with the second shaft portion 42, and the third shaft portion 43 is provided with a first blade 44.
The push plate 6 is limited in the circumferential direction and is connected with the inner cylinder 31 in an up-down sliding manner. Specifically, the inner cylinder 31 is provided with a longitudinal guide rail 34, and the push plate 6 is slidably connected to the guide rail 34.
The first shaft portion 41 is fixedly sleeved with a connecting disc 45, and the upper ends of the shafts of the second stirring paddles 5 are fixedly connected with the lower surface of the connecting disc 45. The connecting disc 45 is in sliding connection with the cooling cylinder 3 in the circumferential direction, specifically, an annular upper sliding rail 35 is arranged on the upper surface of the top cylinder part 33, and the connecting disc 45 is in sliding connection with the sliding rail 35. Through the above arrangement, the stability of the rotation of the second stirring paddle 5 is ensured.
The cooling cylinder 3 is slidably connected with shaft portions of the second stirring paddles 5 in the circumferential direction, specifically, an annular outer sliding rail 36 is arranged on the outer wall of the outer cylinder 32, and the shaft portions of the second stirring paddles 5 are slidably connected with the outer sliding rail 36. The shaft portion of the second stirring paddle 5 is provided with a second blade 51. By the above arrangement, the stability of the rotation of the second stirring paddle 5 is further ensured.
The push plate 6 is in the top in the initial time, when carrying out the hydrolysis, in reaction material pours into the cauldron body 1, communicate through siphunculus 7 between cooling cylinder 3 outside cavity and the cooling cylinder 3 inboard cavity, reaction material pours into in cooling cylinder 3 outside cavity and the cooling cylinder 3 inboard cavity into, the inside and outside both sides reaction material liquid level is equal high and reaction material liquid level is less than push plate 6, first stirring rake 4 rotates the material in the cooling cylinder 3 inboard cavity into stirring, simultaneously first stirring rake 4 drives second stirring rake 5 and rotates the material in the cooling cylinder 3 outside cavity into stirring, first stirring rake 4 drives push plate 6 when making a round trip to rotate and goes up and down, push plate 6 descends the in-process with the material propelling movement in the cooling cylinder 3 outside cavity into cooling cylinder 3, the material liquid level in the cooling cylinder 3 outside cavity becomes high in the cooling cylinder 3 outside cavity later, the material liquid level in the cooling cylinder 3 outside cavity becomes equal high again, promote the flow of cauldron body 1 bottom material through the lift of push plate 6, prevent to adhere in the bottom, promote abundant going on of hydrolysis. In addition, the cooling cylinder 3 is communicated with the jacket 2, and cooling water or heating steam can be introduced into the inner cavity of the cooling cylinder 3, so that the hydrolysis process and the rapid cooling in the hydrolysis process are facilitated, and the reaction materials are uniformly heated. The hydrolysis kettle can stir and promote the flow of materials in the kettle body, and especially promote the flow of materials at the bottom, so that the hydrolysis is more sufficient and efficient. As a result, it was found that, after the hydrolysis tank was modified by the present invention, the thiamphenicol amine refined products obtained in examples 4 to 6 were 11.14g, 11.23g, 10.65g in this order, and the product purity was improved by 2.46% on average over examples 1 to 3.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Claims (6)
1. A preparation method for efficiently recovering thiamphenicol amine is characterized by comprising the following steps: adding liquid alkali into florfenicol mother liquor containing florfenicol, thiamphenicol and florfenicol amine, regulating the pH to 13-14, heating the system to 80 ℃ after stirring for a period of time, preserving heat for a period of time, regulating the pH of the system to 13-14 by using the liquid alkali, continuing preserving heat for a period of time, regulating the pH of the system to 6.5-8 by using the liquid alkali, evaporating and recovering alcohol and water to obtain a crude thiamphenicol amine product, and purifying to obtain a refined thiamphenicol amine product.
2. The method for preparing the thiamphenicol amine with high efficiency according to claim 1, which is characterized in that: the florfenicol mother solution is the mother solution which is remained after the florfenicol crude product is separated after the hydrolysis reaction in the production of the synthetic florfenicol.
3. The method for preparing the thiamphenicol amine with high efficiency according to claim 1, which is characterized in that: adding liquid alkali into the florfenicol mother solution, adjusting the pH value to 13-14, and stirring for 30min.
4. The method for preparing the thiamphenicol amine with high efficiency according to claim 1, which is characterized in that: the temperature is raised to 80 ℃ and then the heat preservation time is 1-2h.
5. The method for preparing the thiamphenicol amine with high efficiency according to claim 1, which is characterized in that: and then adjusting the pH value of the system to 13-14 by liquid alkali, and then continuing to keep the temperature for 2 hours.
6. The method for preparing the thiamphenicol amine with high efficiency according to claim 1, which is characterized in that: the purification treatment of the thiamphenicol crude product comprises the following steps: dissolving the thiamphenicol crude product in drinking water, cooling to-5 to 0 ℃ and crystallizing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310548861.2A CN116574040A (en) | 2023-05-16 | 2023-05-16 | Preparation method for efficiently recycling thiamphenicol amine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310548861.2A CN116574040A (en) | 2023-05-16 | 2023-05-16 | Preparation method for efficiently recycling thiamphenicol amine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116574040A true CN116574040A (en) | 2023-08-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310548861.2A Pending CN116574040A (en) | 2023-05-16 | 2023-05-16 | Preparation method for efficiently recycling thiamphenicol amine |
Country Status (1)
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1743308A (en) * | 2005-08-12 | 2006-03-08 | 中国科学院上海有机化学研究所 | The novel synthesis of thiamphenicol and florfenicol and key intermediate thereof |
| CN1869016A (en) * | 2006-07-04 | 2006-11-29 | 福建出入境检验检疫局检验检疫技术中心 | Preparation method of fluoro thiamphenicol metabolite fluoro thiamphenicol amine |
| US20070197823A1 (en) * | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V | Fenicol compounds and methods synthesizing 2-trifluoroacetamido-3-substituted propiophenone compounds |
| CN102491953A (en) * | 2011-12-05 | 2012-06-13 | 江西日上化工有限公司 | Method for synthesizing florfenicol midbody RT0131 |
| CN111153838A (en) * | 2020-01-19 | 2020-05-15 | 浙江大学宁波理工学院 | Synthetic method of florfenicol |
-
2023
- 2023-05-16 CN CN202310548861.2A patent/CN116574040A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1743308A (en) * | 2005-08-12 | 2006-03-08 | 中国科学院上海有机化学研究所 | The novel synthesis of thiamphenicol and florfenicol and key intermediate thereof |
| US20070197823A1 (en) * | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V | Fenicol compounds and methods synthesizing 2-trifluoroacetamido-3-substituted propiophenone compounds |
| CN1869016A (en) * | 2006-07-04 | 2006-11-29 | 福建出入境检验检疫局检验检疫技术中心 | Preparation method of fluoro thiamphenicol metabolite fluoro thiamphenicol amine |
| CN102491953A (en) * | 2011-12-05 | 2012-06-13 | 江西日上化工有限公司 | Method for synthesizing florfenicol midbody RT0131 |
| CN111153838A (en) * | 2020-01-19 | 2020-05-15 | 浙江大学宁波理工学院 | Synthetic method of florfenicol |
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