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研究生： 范雅淇
Ya-Chi Fan
論文名稱： 高溶解性化合物的結晶製程設計：十二烷基硫酸鈉
Crystallization Process Design of a Highly Soluble Compound: Sodium Dodecyl Sulfate (SDS)
指導教授： 李度
Tu Lee
口試委員:
學位類別： 碩士
Master
系所名稱： 工學院 - 化學工程與材料工程學系
Department of Chemical & Materials Engineering
論文出版年： 2018
畢業學年度： 106
語文別： 英文
論文頁數： 93
中文關鍵詞： 結晶 、製程設計 、高溶解性化合物 、十二烷基硫酸鈉
外文關鍵詞： Crystallization, Process Design, Highly Soluble Compound, Sodium Dodecyl Sulfate (SDS)
相關次數： 點閱：19  下載：0 
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    • 在文獻回顧中，蒸發結晶、反溶劑結晶以及冷卻結晶法為分離及純化常見之技術，但多為各別探討，較少文獻針對此三種結晶製程合併及放大規模的討論。因此，本研究的目的是發展對於高溶解度分子：十二烷基硫酸鈉（SDS）具有再現性之結晶製備程序，由冷卻結晶、蒸發結晶以及反溶劑結晶法共同組成，並預期能達到理想的產品性質，如產量、顆粒尺寸分佈（PSD）和純度。此合併結晶製程的產率為80.2％至90.2％，其中母液從25℃冷卻至5℃，藉由加入晶種及將丙酮以先慢後快的方式加入的應用，確實可以將PSD改善，其中晶體之平均尺寸為125至177 μm。所產出的晶體皆經過偏振光學顯微鏡（POM）、傅里葉變換紅外光譜（FTIR）、粉末X射線衍射（PXRD）和熱重分析（TGA）完整的鑑定。根據FTIR、PXRD和TGA之檢測結果，產出的SDS與購買的SDS相同。此外，我們也將文獻中提供的SDS-H2O相圖及在蒸發過程中的SDS溶液組成變化進行了相關的研究及比對。

    Evaporative, anti-solvent and cooling crystallization are common techniques used in purification and separation, and have been well-studied individually in the literatures. However, there is a few study related to the combination and scaling-up of those three crystallization processes. Therefore, the aim of this research is to develop a reproducible production of a highly water soluble compound: sodium doedecyl sulfate (SDS) through the combined process of evaporative, anti-solvent and cooling crystallization systematically with the desired product attributes such as yield, particle size distribution (PSD) and purity. The yield for the combined crystallization process was 80.2% to 90.2%, where the mother liquor was cooled from 25℃ to 5℃. PSD could indeed be narrowed by applying seeding strategy accompanying with cubic addition of acetone in the combined crystallization process, the mean crystal size was 125 to 177 μm. The produced crystals were also characterized by polarized optical microscopy (POM), Fourier-transform infrared spectroscopy (FTIR), powder X-ray diffraction (PXRD) and thermogravimetric analysis (TGA). Based on the results of FTIR, PXRD and TGA, the produced SDS was identical with the purchased SDS. In addition, the variation of composition during evaporation process was investigated experimentally by the SDS-H2O phase diagram provided in the literature.

    摘要　　i Abstract　　ii Acknowledgement　　iii Table of Contents　　iv List of Figures　　vii List of Tables　　x Chapter 1 Introduction　　1 1.1 Evaporative Crystallization　　2 1.2 Antisolvent Crystallization　　3 1.3 Cooling Crystallization　　3 1.4 Seeding　　6 1.5 Sodium Dodecyl Sulfate (SDS)　　9 1.6 Conceptual Framework　　12 1.7 References　　14 Chapter 2 Experimental Materials and Methods　　19 2.1 Materials　　19 2.1.1 Chemical　　19 2.1.2 Solvents　　19 2.2 Experimental Methods　　21 2.2.1 Initial Solvent Screening　　21 2.2.2 Combination of Composition Variation with Phase Diagram during Evaporation Process　　22 2.2.3 Determination of the End Point for Evaporation　　23 2.2.4 Solubility Measurement of SDS　　24 2.2.5 Preparation of Seeds　　24 2.2.6 Crystallization Process Design　　25 2.2.7 Wet Sieve Analysis Method　　29 2.3 Analytical Measurements　　30 2.3.1 Thermogravimetric Analysis (TGA)　　30 2.3.2 Powder X-ray Diffraction (PXRD)　　31 2.3.3 Fourier Transform Infrared (FTIR) Spectroscopy　　32 2.3.4 Optical Microscopy (OM)　　33 2.3.5 Dynamic Light Scattering (DLS)　　34 2.4 References　　35 Chapter 3 Results and Discussion　　36 3.1 Use Test of SDS　　36 3.2 Initial Solvent Screening of SDS　　43 3.3 Combination of Composition Variation with Phase Diagram during Evaporation Process　　46 3.4 Determination of the End Point for Evaporation　　49 3.5 Solubility Test　　53 3.6 Seeds Aging　　59 3.7 Crystallization Process Design　　62 3.8 References　　72 Chapter 4 Conclusions and Future Works　　75 4.1 Conclusions　　75 4.2 Future Works　　76

    Chapter 1
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    13. Tung, H. H.; Paul, E. L.; Midler, M.; Mccauley, J. A. Cooling Crystallization. In Crystallization of Organic Compounds: An Industrial Perspective; John Wiley & Sons, Inc.: New Jersey, 2009, pp 137-166.
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    18. Tung, H. H.; Paul, E. L.; Midler, M.; Mccauley, J. A. Critical Issues in Crystallization Practice. In Crystallization of Organic Compounds: An Industrial Perspective; John Wiley & Sons, Inc.: New Jersey, 2009, pp 101-116.
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    23. Coiro, V. M.; Manigrasso, M.; Mazza, F.; Pochetti, G.Structure of a Triclinic Phase of Sodium Dodecyl Sulfate Monohydrate. A Comparison with Other Sodium Dodecyl Sulfate Crystal Phases. Acta Crystallogr. 1987, C43 (43), 850–854.
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    Chapter 2
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    Chapter 3
    1. Wang, W.; Lu, H.; Liu, Y.; Leng, J. Sodium Dodecyl Sulfate/Epoxy Composite: Water-Induced Shape Memory Effect and Its Mechanism. J. Mater. Chem. A 2014, 2 (15), 5441-5549.
    2. Sundell, S.The Crystal Structure of Sodium Dodecyl Sulfate. Acta Chem. Scand. 1977, A31, 799–807.
    3. Coiro, V. M.; Mazza, F.; Pochetti, G.Crystal Phases Obtained from Aqueous Solutions of Sodium Dodecyl Sulfate. The Structure of a Monoclinic Phase of Sodium Dodecyl Sulfate Hemihydrate. Acta Crystallogr. 1986, C42 (2), 991–995.
    4. Coiro, V. M.; Manigrasso, M.; Mazza, F.; Pochetti, G.Structure of a Triclinic Phase of Sodium Dodecyl Sulfate Monohydrate. A Comparison with Other Sodium Dodecyl Sulfate Crystal Phases. Acta Crystallogr. 1987, C43 (43), 850–854.
    5. Smith, L. A.; Hammond, R. B.; Roberts, K. J.; Machin, D.; McLeod, G.Determination of the Crystal Structure of Anhydrous Sodium Dodecyl Sulphate Using a Combination of Synchrotron Radiation Powder Diffraction and Molecular Modelling Techniques. J. Mol. Struct. 2000, 554 (2–3), 173–182.
    6. Lee, T.; Kuo, C. S.; Chen, Y. H. Solubility, Polymorphism, Crystallinity, and Crystal Habit of Acetaminophen and Ibuprofen by Initial Solvent Screening. Pharm. Technol. 2006, 30 (10), 72-92.
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    8. Tung, H. H.; Paul, E. L.; Midler, M.; Mccauley, J. A. Evaporative Crystallization. In Crystallization of Organic Compounds: An Industrial Perspective; John Wiley & Sons, Inc.: New Jersey, 2009, pp 167-178.
    9. Hoang, H.; Galliero, G. Shear Viscosity of Inhomogeneous Fluids. J. Chem. Phys. 2012, 136 (124902), 1-8.
    10. Kékicheff, P. Phase Diagram of Sodium Dodecyl Sulfate-Water System. J. Colloid Interface Sci. 1989, 131 (1), 133–152.
    11. Sood, A. K.; Sharma, S.Influence of Organic Solvents and Temperature on the Micellization of Conventional and Gemini Surfactants: A Conductometric Study. Phys. Chem. Liq. 2016, 54 (5), 574–588.
    12. Ghosh, S.; Roy, A.; Banik, D.; Kundu, N.; Kuchlyan, J.; Dhir, A.; Sarkar, N.How Does the Surface Charge of Ionic Surfactant and Cholesterol Forming Vesicles Control Rotational and Translational Motion of Rhodamine 6G Perchlorate (R6G ClO4)? Langmuir 2015, 31 (8), 2310–2320.
    13. Afzal, M.; Kundu, P.; Das, S.; Ghosh, S.; Chattopadhyay, N. A Promising Strategy for Improved Solubilization of Ionic Drugs Simply by Electrostatic Pushing. RSC Adv. 2017, 7 (69), 43551–43559.
    14. Pal, N.; Saxena, N.; Mandal, A.Synthesis, Characterization, and Physicochemical Properties of a Series of Quaternary Gemini Surfactants with Different Spacer Lengths. Colloid Polym. Sci. 2017, 295 (12), 2261–2277.
    15. Lee, T.; Lin, M.S. Sublimation Point Depression of Tris(8-hydroxyquinoline)aluminum(III) (Alq3) by Crystal Engineering. Crys. Growth Des. 2007, 7 (9), 1803-1810.
    16. Reus, M.A.; Guguta, C.; Kramer, H. J. M.; Horst, J. H. Solubility : Importance , Measurements and Applications. Technobis Crystallization Systems White Paper. 2016, 1-8.
    17. Park, M.W.; Yeo, S.D. Antisolvent Crystallization of Sulfa Drugs and the Effect of Process Parameters. Sep. Sci. Technol. 2010, 45 (10), 1402–1410.
    18. Tao, M.; Wang, Z.; Gong, J.; Hao, H.; Wang, J. Determination of the Solubility, Dissolution Enthalpy, and Entropy of Pioglitazone Hydrochloride (Form II) in Different Pure Solvents. Ind. Eng. Chem. Res. 2013, 52 (8), 3036–3041.
    19. Tung, H. H.; Paul, E. L.; Midler, M.; Mccauley, J. A. Critical Issues in Crystallization Practice. In Crystallization of Organic Compounds: An Industrial Perspective; John Wiley & Sons, Inc.: New Jersey, 2009, pp 101-116.
    20. O’sullivan, B.; Smith, B.; Baramidze, G. Recent Advances for Seeding a Crystallization Process: A Review of Modern Techniques. Mettler Toledo White Paper, 2016.

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