CN1039412C - Production of oxytetracycline hydrochloride - Google Patents
Production of oxytetracycline hydrochloride Download PDFInfo
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- CN1039412C CN1039412C CN93114290A CN93114290A CN1039412C CN 1039412 C CN1039412 C CN 1039412C CN 93114290 A CN93114290 A CN 93114290A CN 93114290 A CN93114290 A CN 93114290A CN 1039412 C CN1039412 C CN 1039412C
- Authority
- CN
- China
- Prior art keywords
- liquid
- oxytetracycline
- tetramycin hydrochloride
- acid alcohol
- terramycin
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 title abstract description 6
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 title abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000007788 liquid Substances 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000008014 freezing Effects 0.000 claims abstract description 9
- 238000007710 freezing Methods 0.000 claims abstract description 9
- 238000000926 separation method Methods 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- DVWJFTGEISXVSH-CWVFEVJCSA-N (1R,3S,5S,7Z,11R,12S,13Z,15Z,17Z,19Z,21R,23S,24R,25S)-21-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-12-ethyl-1,3,5,25-tetrahydroxy-11-methyl-9-oxo-10,27-dioxabicyclo[21.3.1]heptacosa-7,13,15,17,19-pentaene-24-carboxylic acid Chemical compound CC[C@H]1\C=C/C=C\C=C/C=C\[C@@H](C[C@@H]2O[C@@](O)(C[C@H](O)[C@H]2C(O)=O)C[C@@H](O)C[C@@H](O)C\C=C/C(=O)O[C@@H]1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O DVWJFTGEISXVSH-CWVFEVJCSA-N 0.000 claims description 27
- 229930183279 tetramycin Natural products 0.000 claims description 27
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 238000005119 centrifugation Methods 0.000 claims description 16
- KIPLYOUQVMMOHB-MXWBXKMOSA-L [Ca++].CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O.CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O Chemical compound [Ca++].CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O.CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O KIPLYOUQVMMOHB-MXWBXKMOSA-L 0.000 claims description 13
- 239000012452 mother liquor Substances 0.000 claims description 13
- 229940063650 terramycin Drugs 0.000 claims description 13
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- 238000005373 pervaporation Methods 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 10
- 239000012528 membrane Substances 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 5
- 238000009736 wetting Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000005516 engineering process Methods 0.000 abstract description 5
- 238000001914 filtration Methods 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 239000004100 Oxytetracycline Substances 0.000 abstract 2
- 229960000625 oxytetracycline Drugs 0.000 abstract 2
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 abstract 2
- 235000019366 oxytetracycline Nutrition 0.000 abstract 2
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 abstract 2
- 239000013078 crystal Substances 0.000 abstract 1
- 238000004042 decolorization Methods 0.000 abstract 1
- 239000006193 liquid solution Substances 0.000 abstract 1
- 230000001502 supplementing effect Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 7
- 239000002699 waste material Substances 0.000 description 6
- 238000007599 discharging Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
- 208000030090 Acute Disease Diseases 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a new technology of producing oxytetracycline hydrochloride. The new technology is characterized in that a small amount of water whose boiling point is higher than that of methanol is directly separated from a system in the filter liquid (namely mother liquid) obtained by decolorization or centrifugal separation, and thus, the mother liquid can directly go back to a dissolving tank for dissolving oxytetracycline dihyclorate. The production process to obtain oxytetracycline hydrochloride crystals comprises the following steps: adding a proper amount of acid alcohol to the mother liquid solution containing oxytetracycline dihyclorate to obtain mixed liquid, decolorizing the mixed liquid by using active carbon, filtering the mixed liquid to obtain clear liquid, then filtering out water content of the clear liquid, supplementing a proper amount of acid alcohol, and freezing and crystallizing the product obtained in the previous step. The technology of the present invention is used to improve the yield of oxytetracycline hydrochloride, reduce energy consumption, and reduce the production cost of the oxytetracycline hydrochloride.
Description
The present invention relates to a kind of new process of production of tetramycin hydrochloride, belong to medicine system affair technical field.
Terramycin has Oxytetracycline Base BP (98) and two kinds of products of tetramycin hydrochloride, and Oxytetracycline Base BP (98) solubleness in water is little, is difficult for being absorbed by the body, and drug effect is slow.Tetramycin hydrochloride solubleness in water is big, easily is absorbed by the body, and curative effect is fast, is suitable for intramuscular injection, and acute disease is treated in smelting.After tetramycin hydrochloride added hydrochloric acid by Oxytetracycline Base BP (98), separating purifies made.
The production process of existing tetramycin hydrochloride is as shown in Figure 1: Oxytetracycline Base BP (98) is used dissolve with methanol in dissolving tank, adds the hydrogen chloride methanol solution (abbreviation acid alcohol) that contains HCl20～40% simultaneously, and adds CaCl
2Make the tetramycin hydrochloride methanol solution, this solution activated carbon decolorizing is removed partial impurities, mixed solution after filtration, isolate behind the solid slag clear liquid, after clear liquid is added an amount of acid alcohol, carry out freezing and crystallizing, separate out the tetramycin hydrochloride crystallization, through centrifugation, and with after the small amount of methanol washing, crystallization, drying again must wet, promptly get the tetramycin hydrochloride finished product, centrifugation gained filtrate is mainly methyl alcohol, wherein contains tetramycin hydrochloride and water, in adding alkali and after reclaim methyl alcohol with distillation method, reuse.Distillation tower still waste liquid directly discharges, and waste liquid is mainly the water and soil mycin, and wherein the main source of water is that institute is moisture in the raw material Oxytetracycline Base BP (98).
The characteristics of this method are in order to remove the water of the system that brought into by raw material Oxytetracycline Base BP (98) etc., adopt distillation method to separate centrifugation gained filtrate (mother liquor), distillation cat head gained Methanol Recovery is used, gained contains the direct discharging of waste water of terramycin at the bottom of the tower, and its shortcoming is that the part terramycin loses with discharging of waste liquid, and the yield of tetramycin hydrochloride is low, when distillation method reclaims methyl alcohol in addition, a large amount of lower boiling methyl alcohol steam with the gas form from the distillation cat head, and energy consumption is big, so the cost height of tetramycin hydrochloride.
The objective of the invention is filtrate after decolouring or the centrifugation gained filtrate (mother liquor) directly the less water that boiling point is high than methyl alcohol separates from system.Thereby mother liquor can directly return dissolving tank and use for the dissolving Oxytetracycline Base BP (98), avoids terramycin to lose with discharging of waste liquid, improves the tetramycin hydrochloride yield.Deduct the distillation reclaimer operation of methyl alcohol simultaneously, cut down the consumption of energy.
Content of the present invention is: referring to Fig. 2, Oxytetracycline Base BP (98) with the mother liquor dissolving, adds an amount of acid alcohol again in dissolving tank, and the solution composition of making is a methyl alcohol: 76～78%, and terramycin: 16～18%, water: 2～3%, CaCl
2: 4%, HCl:0.5% uses activated carbon decolorizing, and the gac add-on is about about 0.1～0.5% of terramycin alkali number, looks how much and suitably increase and decrease of impurity level in the Oxytetracycline Base BP (98).Mixed solution after filtration clear liquid, isolate wherein portion water with the pervaporation membrane separation unit, membrane separation unit is at 70～90 ℃, absolute pressure 1～10KPa operation down behind the film, the branch output of water equals the water yield of bringing in the acid alcohol of Oxytetracycline Base BP (98) and adding system.Membrane sepn gained refined liquid is added an amount of acid alcohol, carries out freezing and crystallizing under 0 ℃～-10 ℃, separates out the tetramycin hydrochloride crystallization.With after centrifugation, the crystallization of must wetting, drying promptly gets the tetramycin hydrochloride finished product again.Centrifugation gained filtrate is mother liquor, directly returns the usefulness of dissolving tank for the dissolving raw material terramycin.Total add-on of secondary acid alcohol is determined by following relationship: the HCl add-on is the loss amount of and system required with the Oxytetracycline Base BP (98) reaction production tetramycin hydrochloride that adds, and the methyl alcohol add-on is the loss amount in the system operation.
Description of drawings:
Fig. 1 is the production scheme of tetramycin hydrochloride in the prior art;
Fig. 2 is a new process of production schema of the present invention;
Fig. 3 is another technical process of new process of production of the present invention.
The difference of flow process shown in Figure 3 and Fig. 2 flow process is pervaporation dehydrating step position on stream not With. The pervaporation dehydration is after freezing and crystallizing and centrifugation in Fig. 3 flow process, centrifugation gained filtrate (mother Liquid), after separating water outlet, pervaporation directly returns dissolving tank for the usefulness of dissolving raw material terramycin.
Characteristics of the present invention be with the pervaporation membrane separation process directly from the clear liquid (such as Fig. 2 technology) of clean system or mother liquor (as Fig. 3 technology) remove the water of the system of bringing in, do not have discharging of waste liquid, the terramycin of avoiding old process waste liquor row to cause decreases Lose. Therefore improved the yield of occrycetin, deducted simultaneously and reclaimed the used still-process of methyl alcohol, can reduce Energy consumption, overall result be can the decrease occrycetin production cost.
Embodiment:
Embodiment 1: get mother liquor 1200kg and (wherein contain methyl alcohol 1107.6kg, tetramycin hydrochloride 15kg, water 16.9kg, CaCl
260kg, HCl0.5kg), Oxytetracycline Base BP (98) 250kg (wherein water 20kg, impurity is a small amount of), acid alcohol 15.1kg is warming up to 50 ℃ in dissolving tank, be stirred to dissolving fully.Add the 780g gac, continue to stir 30 minutes, filter with plate-and-frame filter press, gained filtrate is sent into board-like membrane separation unit, 90 ℃ of solution temperatures, carries out process of pervaporation behind the film under the absolute pressure 5KPa, separates water outlet 20kg, methyl alcohol 240kg.After pervaporation gained refined liquid is added an amount of acid alcohol, under-5 ℃, carry out freezing and crystallizing.The gained crystallization separates with separating centrifuge, and wet crystallization drying gets tetramycin hydrochloride 240kg, and the mother liquid obtained 1200kg of centrifugation is for reusing.
Embodiment 2: get mother liquor 2000kg, Oxytetracycline Base BP (98) 400kg (wherein moisture 32kg), acid alcohol 25kg, in dissolving tank, be warming up to 50 ℃, be stirred to dissolving fully, add gac 1500g, continue to stir 30 minutes, filter in pressure filter, gained filtrate is sent into membrane separation unit.70 ℃ of solution temperatures, carry out the infiltration evaporation process behind the film under the absolute pressure 1KPa.Separate water outlet 32kg, methyl alcohol 60kg after refined liquid is added an amount of acid alcohol, carries out freezing and crystallizing under 0 ℃, centrifugation subsequently, and the crystallization of must wetting, drying gets tetramycin hydrochloride 390kg, and the mother liquid obtained 2000kg altogether of centrifugation is for reusing.
Embodiment 3: get mother liquor 1200kg and (wherein contain methyl alcohol 1110kg, tetramycin hydrochloride 22.5kg, water 7kg, CaCl
260kg, HCl0.5kg), Oxytetracycline Base BP (98) 240kg (wherein water 19kg), acid alcohol 14.5kg is warming up to 50 ℃ in dissolving tank, be stirred to dissolving fully.Add the 750g gac, continue to stir 30 minutes, mixed solution filters, and filtrate is added the laggard capable freezing and crystallizing of an amount of acid alcohol.The crystallization of must wetting of centrifugation subsequently, drying gets tetramycin hydrochloride 230kg.Centrifugation gained filtrate (mother liquor) is sent into membrane separation unit, 80 ℃ of solution temperatures, carries out pervaporation behind the film under the absolute pressure 3KPa, separates water outlet 19kg, methyl alcohol 40kg.Pervaporation gained refined liquid is directly returned dissolving tank, uses for the dissolving raw material Oxytetracycline Base BP (98).
Claims (2)
1, a kind of novel process of making tetramycin hydrochloride is characterized in that manufacturing processed is made up of following each step:
(1) Oxytetracycline Base BP (98) is dissolved with mother liquor, add acid alcohol again, the solution composition of making (weight percent) is: methyl alcohol: 76～78%, and terramycin: 16～18%, water: 2～3%, CaCl
2: 4%, HCl:0.5%;
(2) use activated carbon decolorizing, the add-on of gac is 0.1～0.5% of a terramycin alkali number;
(3) above-mentioned mixed solution is filtered clear liquid, isolate wherein portion water with the pervaporation membrane separation unit, its operating parameters is 70 ℃～90 ℃ of temperature, absolute pressure 1～10KPa behind the film;
(4) in the refined liquid in above-mentioned the 3rd step, add acid alcohol, under 0 ℃～10 ℃, carry out freezing and crystallizing;
(5) with above-mentioned tetramycin hydrochloride crystallization through the centrifugation crystallization of must wetting, drying gets the tetramycin hydrochloride finished product again, isolating mother liquor returns dissolving tank, uses for the dissolving raw material Oxytetracycline Base BP (98).
2, a kind of novel process of making tetramycin hydrochloride is characterized in that manufacturing processed is made up of following each step:
(1) Oxytetracycline Base BP (98) is dissolved with mother liquor, add acid alcohol again, the solution composition of making (weight percent) is: methyl alcohol: 76～78%, and terramycin: 16～18%, water: 2～3%, CaCl
2: 4%, HCl:0.5%;
(2) use activated carbon decolorizing, the add-on of gac is 0.1～0.5% of a terramycin alkali number;
(3) in the solution in above-mentioned second step, add acid alcohol, on 0 ℃～10 ℃, carry out freezing and crystallizing;
(4) with above-mentioned tetramycin hydrochloride crystallization through the centrifugation crystallization of must wetting, drying gets the tetramycin hydrochloride finished product again;
(5) centrifugation gained filtrate is isolated wherein portion water with the pervaporation membrane separation unit, its operating parameters is 70 ℃～90 ℃ of temperature, absolute pressure 1～10KPa behind the film, and the refined liquid of pervaporation is returned dissolving tank, uses for the dissolving raw material Oxytetracycline Base BP (98).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN93114290A CN1039412C (en) | 1993-11-12 | 1993-11-12 | Production of oxytetracycline hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN93114290A CN1039412C (en) | 1993-11-12 | 1993-11-12 | Production of oxytetracycline hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1090268A CN1090268A (en) | 1994-08-03 |
| CN1039412C true CN1039412C (en) | 1998-08-05 |
Family
ID=4990454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93114290A Expired - Fee Related CN1039412C (en) | 1993-11-12 | 1993-11-12 | Production of oxytetracycline hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1039412C (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101570495A (en) * | 2008-04-28 | 2009-11-04 | 大丰华曙药业有限公司 | Production process of oxytetracycline dihydrate hydrochloride |
| CN101823980B (en) * | 2010-04-29 | 2013-09-18 | 赤峰制药股份有限公司 | Preparation method of large-grain occrycetin |
| CN101811979B (en) * | 2010-04-29 | 2012-10-31 | 赤峰制药股份有限公司 | Technology for producing injection-grade terramycin |
| CN101914035B (en) * | 2010-08-27 | 2014-03-05 | 扬州联博药业有限公司 | Method for preparing oxytetracycline hydrochloride |
| CN102816084B (en) * | 2012-09-10 | 2015-02-04 | 赤峰奥贝思医药科技有限责任公司 | Method for preparing injection-grade oxytetracycline |
| CN107011205B (en) * | 2017-04-12 | 2019-10-01 | 扬州联博药业有限公司 | A method of producing large-grain occrycetin |
| CN107522631B (en) * | 2017-09-13 | 2019-12-20 | 盐城市大丰区天生联合药业有限公司 | Preparation method of oxytetracycline hydrochloride |
| CN108586277B (en) * | 2018-05-29 | 2020-12-04 | 江西国药有限责任公司 | Preparation method of oxytetracycline hydrochloride fine particle salt |
| CN112624937A (en) * | 2020-12-23 | 2021-04-09 | 江苏天和制药有限公司 | Drying method of oxytetracycline hydrochloride |
| CN117820154A (en) * | 2023-11-17 | 2024-04-05 | 盐城苏海制药有限公司 | Resource research method for doxycycline hydrochloride refined salified mother liquor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US507595A (en) * | 1893-10-31 | Ville |
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1993
- 1993-11-12 CN CN93114290A patent/CN1039412C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US507595A (en) * | 1893-10-31 | Ville |
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| Publication number | Publication date |
|---|---|
| CN1090268A (en) | 1994-08-03 |
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