溶析结晶在医药领域的研究进展
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摘要
结晶作为一种传统的分离和提纯工艺,广泛运用于医药、化工、材料等领域。随着对结晶工艺的深入研究和对晶体产品质量越来越高的要求,结晶不再仅仅用于物质的分离和提纯,更重要的是根据产品功能的需要,制备特定结构的晶体。作为结晶的重要组成部分,溶析结晶因其操作简单、能耗相对较低、适用于热敏性物质等优势受到了广泛的关注。本文从溶析结晶相较于其他溶液结晶的不同点出发,重点介绍了溶析结晶热力学、溶析结晶动力学和工艺过程的研究,以及与溶析结晶相关的超临界流体技术和球形结晶技术。溶析结晶热力学关注了溶解度的测定方法和如何通过相图来确定合适的操作条件;溶析结晶动力学,详细描述了间歇、连续溶析结晶动力学模型的建立;工艺过程的研究,包括溶析剂与含有待结晶物质混合、结晶过程的控制和优化。同时本文对溶析结晶目前存在的问题进行了总结,并对未来的发展作了展望。
Crystallization, a traditional method for separation, is widely used in pharmaceutical industry,chemical industry, materials, and other fields. With the deep study on crystallization technology and the strict requirement for the quality of product, crystallization is no longer only used for the separation and purification, but also for the preparations of the crystals with specific structure to fabricate specified functional products. As an important part of crystallization, anti-solvent crystallization has attracted much attention because of its simple operation and relatively low energy consumption and suitability for heat sensitive substances. In this paper, starting from the differences between anti-solvent crystallization and other kinds of solution crystallization, the thermodynamics and kinetics were introduced. The thermodynamics was focusing on the determination method of solubility and suitable operating conditions through phase diagram. The kinetics, described the way to establish batch or continuous crystallization kinetics model, and the process of anti-solvent crystallization, including the mixing of anti-solvent and solution, control and optimization of crystallization process, as well as the supercritical fluid technology and spherical crystallization technology that is the methods related to anti-solvent crystallization. Finally,the future development is prospected.
Crystallization, a traditional method for separation, is widely used in pharmaceutical industry,chemical industry, materials, and other fields. With the deep study on crystallization technology and the strict requirement for the quality of product, crystallization is no longer only used for the separation and purification, but also for the preparations of the crystals with specific structure to fabricate specified functional products. As an important part of crystallization, anti-solvent crystallization has attracted much attention because of its simple operation and relatively low energy consumption and suitability for heat sensitive substances. In this paper, starting from the differences between anti-solvent crystallization and other kinds of solution crystallization, the thermodynamics and kinetics were introduced. The thermodynamics was focusing on the determination method of solubility and suitable operating conditions through phase diagram. The kinetics, described the way to establish batch or continuous crystallization kinetics model, and the process of anti-solvent crystallization, including the mixing of anti-solvent and solution, control and optimization of crystallization process, as well as the supercritical fluid technology and spherical crystallization technology that is the methods related to anti-solvent crystallization. Finally,the future development is prospected.
引文
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[32]WANG J,ZHANG Q,ZHOU Y,et al.Microfluidic synthesis of amorphous cefuroxime axetil nanoparticles with size-dependent and enhanced dissolution rate[J].Chemical Engineering Journal,2010,162(2):844-851.
[33]LIU Z,HUANG Y,JIN Y,et al.Mixing intensification by chaotic advection inside droplets for controlled nanoparticle preparation[J].Chemical Engineering Science,2010,9(4):773-786.
[34]FERN J,OHSAKI S,WATANO S,et al.Continuous synthesis of nanodrug particles by antisolvent crystallization using a porous hollowfiber membrane module[J].International Journal of Pharmaceutical,2018,543(1/2):139-150.
[35]OTHMAN R,VLADISAVLJEVI G T,SIMONE E,et al.Preparation of microcrystals of piroxicam monohydrate by antisolvent precipitation via microfabricated metallic membranes with ordered pore arrays[J].Crystal Growth&Design,2017,17(12):6692-6702.
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[38]BHAMIDI V,LEE S H,HE G,et al.Antisolvent crystallization and polymorph screening of glycine in microfluidic channels using hydrodynamic focusing[J].Crystal Growth&Design,2015,15(7):3299-3306.
[39]FERGUSON S,MORRIS G,HAO H,Characterization of the antisolvent batch,plug flow and MSMPR crystallization of benzoic acid[J].Chemical Engineering Science,2013,104:44-54.
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[41]RAWLINGS J B,MILLER S M,WITKOWSKI W R,et al.Model identification and control of solution crystallization processes:a review[J].Industrial&Engineering Chemistry Research,1993,32(7):1275-1296.
[42]YANG Y,NAGY Z K.Model-based systematic design and analysis approach for unseeded combined cooling and antisolvent crystallization(CCAC)systems[J].Crystal Growth&Design,2014,14(2):687-698.
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[2]龚俊波.工业结晶科学与技术专辑[J].化学工业与工程,2018,35(3):1.GONG J B.Industrial crystallization science and technology[J].Chemical Industry and Engineering,2018,35(3):1.
[3]王静康.结晶[M].//时钧,汪家鼎,余国琮,等.化学工程手册.2版.北京:化学工业出版社,1996:10-11.WANG J K.Crystallization[M].//SHI J,WANG J D,YU G C,et al.Chemical engineering manual.2nd ed.Beijing:Chemical Industry Press,1996:10-11.
[4]THORAT A A,DALVI S V.Liquid antisolvent precipitation and stabilization of nanoparticles of poorly water soluble drugs in aqueous suspensions:recent developments and future perspective[J].Chemical Engineering Journal,2012,181-182:1-34.
[5]MULLER R H,KECK C M.Twenty years of drug nanocrystals:where are we,and where do we go[J].European Journal of Pharmaceutics and Biopharmaceutics,2012,80(1):1-3.
[6]KURUP M,R A R.Antisolvent crystallization a novel approach to bioavailability enhancement[J].European Journal of Biomedical and Pharmaceutical Sciences,2016,3(3):230-234.
[7]MULLIN J W.Crystallization[M].4th.Woburn:ButterworthHeinemann,2001:294.
[8]WANG Z R,ZHOU G Y,DONG J J,et al.Measurement and correlation of the solubility of antipyrine in ten pure and water+ethanol mixed solvents at temperature from(288.15 to 328.15)K[J].Journal of Molecular Liquids,2018,268:256-265.
[9]LI K L,WU S G,XU S J,et al.Oiling out and polymorphism control of pyraclostrobin in cooling crystallization[J].Industrial&Engineering Chemistry Research,2016,55:11631-11637.
[10]LONG B,XIA Y,DENG Z,et al.Understanding the enhanced solubility of 1,3-benzenedicarboxylic acid in polar binary solvents of(acetone+water)at various temperatures[J].The Journal of Chemical Themodynamics,2017,105:105-111.
[11]LI S,JIANG L,QIU J,et al.Solubility and solution thermodynamics of theδform of l?citrulline in water+ethanol binary solvent mixtures[J].Journal of Chemical&Engineering Data,2016,61:264-271.
[12]ZHANG Q,HU Y,YANG Y,et al.Thermodynamic models for determination of the solubility of the the(1∶1)complex of(urea+l?malic acid)in(methanol+acetonitrile)binary solvent mixtures binary solvent mixtures[J].Journal of Chemical&Engineering Data,2015,60:1608-1613.
[13]WANG J,XU A,XU R.Determination and correlation of terephthaldialdehyde solubility in(ethanol,isopropanol,ethyl acetate,isopentanol)+N,N-dimethylformamide mixed solvents at temperatures from 273.15K to 318.15K[J].The Journal of Chemical Themodynamics,2017,105:327-336.
[14]EGHRARY S H,ZARGHAMI R,MARTINEZ F,et al.Solubility of 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketone hydrochloride(amiodarone HCl)in ethanol+water and N-methyl-2-pyrrolidone+water mixtures at various temperatures[J].Journal of Chemical&Engineering Data,2012,57:1544-1550.
[15]CRESTANI C E,BERNARDO A,COSTA C B B,et al.Fructose solubility in mixed(ethanol+water)solvent:experimental data and comparison among different thermodynamic models[J].Journal of Chemical&Engineering Data,2013,58(11):3039-3045.
[16]LI X,YIN Q,ZHANG M,et al.Process design for antisolvent crystallization of erythromycin ethylsuccinate in oiling-out system[J].Industrial&Engineering Chemistry Research,2016,55(27):7484-7492.
[17]KUDO S,TAKIYAMA H.Solubility determination for carbamazepine and saccharin in methanol/water mixed solvent:basic data for design of cocrystal production by antisolvent crystallization[J].Journal of Chemical&Engineering Data,2018,63:451-458.
[18]GRANBERG R A,DUCREUX C,GRACIN S,et al.Primary nucleation of paracetamol in acetone-water mixtures[J].Chemical Engineering Science,2001,56(7):2305-2313.
[19]LINDENBERG C,VICUM L,et al.Antisolvent precipitation of PDI747:kinetics of particle formation and growth[J].Crystal Growth&Design,2007,7(9):1653-1661.
[20]LUO Y,WU G,SUN B.Antisolvent crystallization of biapenem:estimation of growth and nucleation kinetics[J].Journal of Chemical&Engineering Data,2013,58(3):588-597.
[21]NONOYAMA N,HANAKI K,YABUKI Y,et al.Constant supersaturation control of antisolvent-addition batch crystallization[J].Organic Process Research&Development,2006,10(4):727-732.
[22]TRIFKOVIC M,SHEIKHZADEH M,ROHANI S.Kinetics estimation and single and multi-objective optimization of a seeded,anti-solvent,isothermal batch crystallizer[J].Industrial&Engineering Chemistry Research,2018,47:1586-1595.
[23]GARG M,ROY M,CHOKSHI P,et al.Process development in the QbD paradigm:mechanistic modeling of antisolvent crystallization for production of pharmaceuticals[J].Crystal Growth&Design,2018,18(6):3352-3359.
[24]SCHALL J M,MANDUR J S,BRAATZ R D,et al.Nucleation and growth kinetics for combined cooling and antisolvent crystallization in a mixed-suspension,mixed-product removal system:estimating solvent dependency[J].Crystal Growth&Design,2018,18:1560-1570.
[25]HU J,NG W K,DONG Y,et al.Continuous and scalable process for water-redispersible nanoformulation of poorly aqueous soluble APIs by antisolvent precipitation and spray-drying[J].International Journal of Pharmaceutics,2011,404(1/2):198-204.
[26]DOUROUMIS D,SCHELER S,FAHR A.Using a modified shepards method for optimization of a nanoparticulate cyclosporine a formulation prepared by a static mixer technique[J].Journal of Pharmaceutical Sciences,2008,97(2):919-930.
[27]HU T,CHIOU H,CHAN H K,et al.Preparation of inhalable salbutamol sulphate using reactive high gravity controlled precipitation[J].Journal of Pharmaceutical Sciences,2008,97(2):944-949.
[28]JOHNSON B K,PRUD'HOMME R K.Chemical processing and micromixing in confined impinging jets[J].AIChE Journal,2003,49(9):2264-2282.
[29]LIU Y,CHENG C,PRUD HOMME R K,et al.Mixing in a multi-inlet vortex mixer(MIVM)for flash nano-precipitation[J].Chemical Engineering Science,2008,63(11):2829-2842.
[30]DEMELLO A J.Control and detection of chemical reactions in microfluidic systems[J].Nature,2006,442(7101):394-402.
[31]PANAGIOTOU T,MESITE S V,FISHER R J.Production of norfloxacin nanosuspensions using microfluidics reaction technology through solvent/antisolvent crystallization[J].Industrial&Engineering Chemistry Research,2009,48(4):1761-1771.
[32]WANG J,ZHANG Q,ZHOU Y,et al.Microfluidic synthesis of amorphous cefuroxime axetil nanoparticles with size-dependent and enhanced dissolution rate[J].Chemical Engineering Journal,2010,162(2):844-851.
[33]LIU Z,HUANG Y,JIN Y,et al.Mixing intensification by chaotic advection inside droplets for controlled nanoparticle preparation[J].Chemical Engineering Science,2010,9(4):773-786.
[34]FERN J,OHSAKI S,WATANO S,et al.Continuous synthesis of nanodrug particles by antisolvent crystallization using a porous hollowfiber membrane module[J].International Journal of Pharmaceutical,2018,543(1/2):139-150.
[35]OTHMAN R,VLADISAVLJEVI G T,SIMONE E,et al.Preparation of microcrystals of piroxicam monohydrate by antisolvent precipitation via microfabricated metallic membranes with ordered pore arrays[J].Crystal Growth&Design,2017,17(12):6692-6702.
[36]TIERNEY T B,RASMUSON K C,HUDSON S P,et al.Size and shape control of micron-sized salicylic acid crystals during antisolvent crystallization[J].Organic Process Research&Development,2017,21(11):1732-1740.
[37]JIANG S,TER HORST J H,JANSENS P J.Concomitant polymorphism ofο-aminobenzoic acid in antisolvent crystallization[J].Crystal Growth&Design,2008,1(8):37-43.
[38]BHAMIDI V,LEE S H,HE G,et al.Antisolvent crystallization and polymorph screening of glycine in microfluidic channels using hydrodynamic focusing[J].Crystal Growth&Design,2015,15(7):3299-3306.
[39]FERGUSON S,MORRIS G,HAO H,Characterization of the antisolvent batch,plug flow and MSMPR crystallization of benzoic acid[J].Chemical Engineering Science,2013,104:44-54.
[40]NAGY Z K,FUJIWARA M,BRAATZ R D.Modelling and control of combined cooling and antisolvent crystallization processes[J].Journal of Process Control,2008,18(9):856-864.
[41]RAWLINGS J B,MILLER S M,WITKOWSKI W R,et al.Model identification and control of solution crystallization processes:a review[J].Industrial&Engineering Chemistry Research,1993,32(7):1275-1296.
[42]YANG Y,NAGY Z K.Model-based systematic design and analysis approach for unseeded combined cooling and antisolvent crystallization(CCAC)systems[J].Crystal Growth&Design,2014,14(2):687-698.
[43]RIDDER B J,MAJUMDER A,NAGY Z K,et al.Population balance model-based multiobjective optimization of a multisegment multiaddition(MSMA)continuous plug-flow antisolvent crystallizer[J].Industrial&Engineering Chemistry Research,2014,53:4387-4397.
[44]GYULAI O,KOVACS A,SOVANY T,et al.Optimization of the critical parameters of the spherical agglomeration crystallization method by the application of the quality by design approach[J].Materials(Basel),2018,11(4):1-16.
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