CN104311674A - Preparation method of mixed ester - Google Patents
Preparation method of mixed ester Download PDFInfo
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- CN104311674A CN104311674A CN201410554948.1A CN201410554948A CN104311674A CN 104311674 A CN104311674 A CN 104311674A CN 201410554948 A CN201410554948 A CN 201410554948A CN 104311674 A CN104311674 A CN 104311674A
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Abstract
The invention relates to a preparation method of mixed ester, namely hydroxypropyl methylcellulose acetate succinate, belonging to the technical field of pharmaceuticals. The method provided by the invention comprises the following steps: after reaction of hydroxypropyl methyl cellulose, acetic anhydride and butanedioic anhydride, diluting a reaction liquid by using diluting water to obtain a diluted reaction system; then, converting the reaction system into water for precipitation at a certain temperature to obtain a mixed liquid; and then, insulating the mixed liquid at a certain temperature for a certain time, collecting separated products, and washing and drying to obtain the products, wherein the mass ratio of the diluting water to hydroxypropyl methyl cellulose is 3: 1 to 8: 1. By controlling treatment conditions such as amount of the diluting water, the products with relatively good physical and chemical properties can be obtained. The preparation method is convenient in process operation and suitable for industrial production.
Description
Technical field
The present invention relates to a kind of preparation method of the mixed ester as excipient substance, belong to pharmaceutical technology sectors.
Background technology
Hydroxypropyl methylcellulose acetate succinate (hydmxypmpylmethyl cellulose acetate succinate, HPMCAS), be the acetic acid of hydroxypropyl methyl fiber (HPMC) and the mixed ester of succsinic acid (i.e. succinic acid); The enteric-coating material of excellent property, slow-releasing coating material and thin film coating material.HPMCAS film forming properties is good, and safety non-toxic is not easily destroyed by enzyme in vivo, has plasticity-; It is good in upper part of small intestine (duodenum) solvability, and being conducive to increases the absorption of medicine at small intestine; It can prevent the degraded of medicine sour environment under one's belt; Polymer carrier can also be used as.
Containing propoxyl, methoxyl group, ethanoyl, succinyl 4 kinds of groups in hydroxypropyl methylcellulose acetate succinate, present different solubility properties with the difference of group content.Propoxyl is hydrophilic radical, if hydroxypropoxy content is too high, then the strong moistureproofness of water-absorbent is poor, and moisture is combined with succinyl, makes diacyl group be easy to hydrolysis; Methoxyl group is hydrophobic group, and it makes it dissolve in certain organic solvent, is conducive to the preparation of coating membrance; Ethanoyl makes its flexility improve, and acid resistance improves, and material is not reunited bonding, if too high levels, can cause that HPMCAS's is poorly soluble, making coating liquid and medicine add difficulty in man-hour; The existence of succinyl makes coating material free film solubility property make moderate progress, if succinyl content is too high, film properties can be made to have certain reduction, poor water resistance, and acid resistance is poor, and the pH value of dissolving reduces.Different with the content of succinyl according to ethanoyl, hydroxypropyl methylcellulose acetate succinate is divided into H type, M type and L-type 3 kinds of models.
In preparation process, different reactions or post-treatment condition/mode, all may affect the physico-chemical property of the content of these groups or the content of impurity or product, if not control treatment condition, then product easily condenses the larger bulk of formation, affects the outward appearance of product, and easily causes the contaminant overstandard such as free acid, thus cause the quality of product undesirable, be difficult to manipulation in production.Therefore, need to study its reaction conditions and/or post-treatment condition, to obtain, there is good physico-chemical property, the good product of solvability, film-forming properties and stability, and make technique be applicable to suitability for industrialized production.
Summary of the invention
The invention provides a kind of method preparing hydroxypropyl methylcellulose acetate succinate, high-quality product can be obtained easily.
Summary of the invention
The invention provides a kind of method preparing hydroxypropyl methylcellulose acetate succinate, controlled by conditions such as the amount of water to aftertreatment, temperature, high-quality product can be obtained easily.
Detailed Description Of The Invention
In the preparation process of hydroxypropyl methylcellulose acetate succinate, after completion of the reaction, need the product that generates that precipitating is out from reaction system, different post processing mode or condition, the direct quality affecting product, as Different treatments or condition may cause product to lump, is difficult to filter, and it is more to comprise impurity, quality does not conform to symbol requirement.
Inventors have developed a kind of method preparing hydroxypropyl methylcellulose acetate succinate, during aftertreatment after completion of the reaction, control the condition of precipitating product etc., make operation be easy to carry out, and obtain high-quality product.
A kind of method preparing hydroxypropyl methylcellulose acetate succinate comprises: after Vltra tears (HPMC) and diacetyl oxide, Succinic anhydried have reacted, diluting water dilute reaction solution, obtains the reaction system after diluting; Then reaction system is proceeded in certain temperature and a certain amount of precipitating water, obtain mixed solution; Then by mixed solution held for some time at a certain temperature, collect the product of separating out, with water washing, after drying, namely obtain product.
Described Vltra tears (HPMC) and diacetyl oxide, Succinic anhydried react, and can comprise: by acetic acid, HPMC, sodium acetate, anhydrous, succinyl oxide, and acetic anhydride, react at a certain temperature to reacting end.
Contriver is found by research, and the amount of diluting water has material impact to the granular size of product and the difficulty or ease of operation.During diluting water dilute reaction solution, the consumption of described diluting water and the mass ratio of reaction raw materials HPMC are 3:1-8:1.In some embodiments, the consumption of described diluting water and the mass ratio of reaction raw materials HPMC are 4:1-7:1.
After reaction solution is diluted, need reaction system to be proceeded in precipitating water to separate out product.Contriver finds, the amount of precipitating water and the quality of temperature to product have material impact.The mass ratio of described precipitating water and raw material HPMC is 30:1-90:1.In some embodiments, the mass ratio of described precipitating water and raw material HPMC is 40:1-80:1.In some embodiments, the mass ratio of described precipitating water and raw material HPMC is 45:1-75:1.In some embodiments, the mass ratio of described precipitating water and raw material HPMC is 50:1-70:1.
The temperature of described precipitating water needs to control in certain temperature, and form larger bulk to reduce product accumulation and reduce impurity, the temperature of precipitating water is-5 DEG C-20 DEG C.In some embodiments, the temperature of described precipitating water is 0 DEG C-15 DEG C.In some embodiments, the temperature of described precipitating water is-5 DEG C-10 DEG C.In some embodiments, the temperature of described precipitating water is-5 DEG C-5 DEG C.
Be transferred to after in water in reaction system, gained mixture needs to be incubated for some time in certain temperature, to improve the quality of product and to make mixture be easy to filter, obtains the product with better physico-chemical property.The temperature of insulation controls to be 5 DEG C-25 DEG C.In some embodiments, the temperature of insulation controls to be 10 DEG C-20 DEG C.Soaking time is 0.5 hour-2 hours.
In some embodiments, a kind of method preparing hydroxypropyl methylcellulose acetate succinate comprises: after Vltra tears (HPMC) and diacetyl oxide, Succinic anhydried have reacted, be the water of 4:1-7:1 with the mass ratio with HPMC; Then reaction system be transferred in the precipitating water of 0-15 DEG C, precipitating quality is 40-80 times of HPMC quality; Then at 5 DEG C-20 DEG C, be incubated 0.5 hour-2 hours, collect the product of separating out, with water washing, after drying, namely obtain product.
In some embodiments, a kind of method preparing hydroxypropyl methylcellulose acetate succinate comprises: after Vltra tears (HPMC) and diacetyl oxide, Succinic anhydried have reacted, be the water quencher dilute reaction solution of 5:1-6:1 with the mass ratio with HPMC; Then reaction system proceeded in the precipitating water of 0-5 DEG C, precipitating quality is 50-70 times of HPMC quality; Then at 10 DEG C-20 DEG C, be incubated 0.5 hour-2 hours, collect the product of separating out, with water washing, after drying, namely obtain product.
After insulation terminates, can by solids by filtering, mode and the separated from solvent such as centrifugal.Filter or in centrifugal process, can make to wash solid with water.
After obtaining solid crude product, in order to improve the quality of product, water equal solvent can also be used to pull an oar, the purification process such as washing.
The method of the invention, by controlling the condition of aftertreatment, can obtain and be of moderate size, physico-chemical property is good, and the product that foreign matter content is low is conducive to suitability for industrialized production.
Embodiment
In order to make those skilled in the art understand technical scheme of the present invention better, below disclose further some non-limiting embodiments the present invention is described in further detail.
Reagent used in the present invention all can be buied from the market or can be obtained by method described in the invention preparation.
In the present invention, g represents gram, and mL represents milliliter, and cP is viscosity unit's centipoise, ppm represents 1,000,000/.
Embodiment 1
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 3.6g Succinic anhydried and 40g diacetyl oxide, be heated to interior temperature 80 DEG C, react 10 hours, react complete.
Add diluting water 90mL, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 1200mL water of 0 DEG C-5 DEG C in advance, after dropwising, is warming up to 20 DEG C, and 20 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing.Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 400 DEG C of vacuum-dryings to weightlessness, obtains product 19.8g.
Embodiment 2
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 5.5g Succinic anhydried and 25.5g diacetyl oxide, be heated to interior temperature 85 DEG C, react 10 hours, react complete.
Add diluting water 100mL water, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 1400mL water of 0 DEG C-5 DEG C in advance, after dropwising, is warming up to 15 DEG C, and 15 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing.Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 55 DEG C of vacuum-dryings to weightlessness, obtains product 19.9g.
Embodiment 3
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 9g Succinic anhydried and 28g diacetyl oxide, be heated to interior temperature 85 DEG C, react 10 hours, react complete.
Add diluting water 130mL water, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 1000mL water of 0 DEG C-5 DEG C in advance, after dropwising, is warming up to 10 DEG C, and 10 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing.Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.By gained solid 40 DEG C of vacuum-dryings 12 hours, be then less than 2.5% 60 DEG C of vacuum-dryings to weightlessness, obtain product 20.1g.
Embodiment 4
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 5.5g Succinic anhydried and 25.5g diacetyl oxide, be heated to interior temperature 85 DEG C, react 10 hours, react complete.
Add diluting water 80mL water, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 1300mL water of 0 DEG C in advance, after dropwising, is warming up to 15 DEG C, and 15 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing.Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 50 DEG C of vacuum-dryings to weightlessness, obtains product 19.5g.
Embodiment 5
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 3.6g Succinic anhydried and 40g diacetyl oxide, be heated to interior temperature 80 DEG C, react 10 hours, react complete.
Add diluting water 140mL water, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 850mL water of 3 DEG C in advance, after dropwising, is warming up to 15 DEG C, and 15 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing.Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 40 DEG C of vacuum-dryings to weightlessness, obtains product 20.1g.
Embodiment 6-embodiment 9 is comparative example:
Embodiment 6
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 3.6g Succinic anhydried and 40g diacetyl oxide, be heated to interior temperature 80 DEG C, react 10 hours, react complete.
Add diluting water 50mL, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 500mL water of less than 5 DEG C in advance, after dropwising, is warming up to 20 DEG C, and 20 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing (filter cake caking is more serious).Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 60 DEG C of vacuum-dryings to weightlessness, obtains product 20.9g, drying after product is yellow lump.
Embodiment 7
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 3.6g Succinic anhydried and 40g diacetyl oxide, be heated to interior temperature 80 DEG C, react 10 hours, react complete.
Add diluting water 100mL, be stirred to transparent clarification.Then reaction system is dropped in the 1000mL water of 25 DEG C, after dropwising, 20 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing.Gained solid, filters 50 DEG C of making beating 4 hours with 400mL water, filter cake 400mL water washing (filter cake caking is more serious).Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 60 DEG C of vacuum-dryings to weightlessness, obtains product 20.5g, drying after product is yellow lump.
Embodiment 8
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 5.5g Succinic anhydried and 25.5g diacetyl oxide, be heated to interior temperature 85 DEG C, react 10 hours, react complete.
Add diluting water 200mL water, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 2000mL water of less than 5 DEG C in advance, after dropwising, is warming up to 15 DEG C, and 15 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing (product grain is less, is difficult to filter).Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 45 DEG C of vacuum-dryings to weightlessness, obtains product 19.3g.
Embodiment 9
Measuring 80mL glacial acetic acid adds in flask, then takes 18g HPMC (mark viscosity is 3cP), and 2g HPMC (mark viscosity is 15cP) and 10g sodium acetate, anhydrous join in flask, stirring and dissolving.Add 5.5g Succinic anhydried and 25.5g diacetyl oxide, be heated to interior temperature 85 DEG C, react 10 hours, react complete.
Add diluting water 100mL water, be stirred to transparent clarification.Then reaction system being dropped to is cooled in the 1000mL water of less than 5 DEG C in advance, after dropwising, 5 DEG C of insulated and stirred 1 hour.Filter, filter cake 400mL water washing (product grain is less, is difficult to filter).Gained solid, filters, filter cake 400mL water washing 50 DEG C of making beating 4 hours with 400mL water.Gained solid is pulled an oar 4 hours at 50 DEG C with 400mL water again, filters, filter cake 400mL water washing.Gained solid is less than 2.5% 45 DEG C of vacuum-dryings to weightlessness, obtains product 19.0g.
Embodiment 10 quality product detects
Detection method: detect according to Hypromellose Acetate Succinate (i.e. acetic acid hypromellose succinate) the entry related detecting method in American Pharmacopeia USP36-NF31 version;
Detected result is as following table 1: "-" represents not detection;
Table 1
Continued 1:
Can find out according to detected result, the product prepared according to the method for the invention has good physico-chemical property, meets quality standard.
Method of the present invention is described by preferred embodiment, and related personnel obviously can change methods and applications as herein described or suitably change and combination in content of the present invention, spirit and scope, realizes and applies the technology of the present invention.Those skilled in the art can use for reference present disclosure, and suitable improving technique parameter realizes.Special needs to be pointed out is, all similar replacements and change apparent to those skilled in the art, they are all deemed to be included in the present invention.
Claims (7)
1. prepare a method for hydroxypropyl methylcellulose acetate succinate, it comprises: after Vltra tears and diacetyl oxide, Succinic anhydried have reacted, use diluting water dilute reaction solution, obtains the reaction system after diluting; Then reaction system is proceeded in the precipitating water of certain temperature, obtain mixed solution; Then by mixed solution held for some time at a certain temperature, collect the product of separating out, with water washing, after drying, namely obtain product; The mass ratio of described diluting water and Vltra tears is 3:1-8:1.
2. method according to claim 1, the mass ratio of precipitating water and Vltra tears is 30:1-90:1.
3. the method described in claim 1 or 2, the temperature of precipitating water is-5 DEG C-20 DEG C.
4. the arbitrary described method of claim 1-3, comprises the temperature of mixed solution at 5 DEG C-25 DEG C.
5. the arbitrary described method of claim 1-3, comprises and mixed solution is incubated 0.5 hour-2 hours.
6. method according to claim 1, comprise: after Vltra tears and diacetyl oxide, Succinic anhydried have reacted, use diluting water dilute reaction solution, obtain the reaction system after diluting, the mass ratio of diluting water and Vltra tears is 4:1-7:1; Then reaction system be transferred in the precipitating water of 0 DEG C-15 DEG C, the mass ratio of precipitating water and Vltra tears is 40:1-80:1, obtains mixed solution; Then will obtain mixed solution and be incubated 0.5 hour-2 hours at 5 DEG C-20 DEG C, and collect the product of separating out, with water washing, after drying, namely obtain product.
7. method according to claim 1, comprise: after Vltra tears and diacetyl oxide, Succinic anhydried have reacted, use diluting water dilute reaction solution, obtain the reaction system after diluting, the mass ratio of diluting water and Vltra tears is 5:1-6:1; Then reaction system be transferred in the precipitating water of 0 DEG C-5 DEG C, the mass ratio of precipitating water and Vltra tears is 50:1-70:1, obtains mixed solution; Then will obtain mixed solution and be incubated 0.5 hour-2 hours at 10 DEG C-20 DEG C, and collect the product of separating out, with water washing, after drying, namely obtain product.
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| CN105273088A (en) * | 2015-11-16 | 2016-01-27 | 泰安瑞泰纤维素有限公司 | Novel technology for preparing hydroxypropyl methyl cellulose derivative |
| CN107266593A (en) * | 2016-04-05 | 2017-10-20 | 信越化学工业株式会社 | The excellent acetic acid amber hydroxypropyl methylcellulose of solubilised state and its manufacture method, and solid dispersions composition, coated composition, the manufacture method of pastille composition granule and solid pharmaceutical preparation |
| CN107406520A (en) * | 2015-03-16 | 2017-11-28 | 陶氏环球技术有限责任公司 | Method for being classified separation esterified cellulose ether |
| CN110382552A (en) * | 2017-03-17 | 2019-10-25 | 陶氏环球技术有限责任公司 | Method for recycling esterified cellulose ether from mixture of reaction products |
| CN115651085A (en) * | 2022-11-14 | 2023-01-31 | 乳源东阳光药业有限公司 | Purification method of hydroxypropyl methylcellulose acetate succinate |
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| CN107266593B (en) * | 2016-04-05 | 2021-11-12 | 信越化学工业株式会社 | Hydroxypropyl methylcellulose acetate succinate with excellent dissolution state and preparation method thereof |
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| CN115651085A (en) * | 2022-11-14 | 2023-01-31 | 乳源东阳光药业有限公司 | Purification method of hydroxypropyl methylcellulose acetate succinate |
| CN115651085B (en) * | 2022-11-14 | 2023-11-17 | 乳源东阳光药业有限公司 | Purification method of hydroxypropyl methylcellulose acetate succinate |
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Application publication date: 20150128 |