Chemical Resource Recycling and Waste Mitigation in Pharmaceutical Manufacturing Processes

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姓名

葉智豪(Dhanang Edy Pratama) 查詢紙本館藏

畢業系所

化學工程與材料工程學系

論文名稱

Chemical Resource Recycling and Waste Mitigation in Pharmaceutical Manufacturing Processes
(Chemical Resource Recycling and Waste Mitigation in Pharmaceutical Manufacturing Processes)

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至系統瀏覽論文 (2026-1-10以後開放)

摘要(中)

由於永續觀念的重要性逐漸興起，製藥領域也希望可將此觀念帶入其行業中發展。為了有助於了解那些模式的轉變，提出了一系列從開發產品至最終產品皆採用永續性方法的範例研究。

在範例一中，介紹了在開發(R,S)-(±)-ibuprofen的手性分析範例中，藉由漿料反應結晶來回收過量的試劑及溶劑。拆分劑(56.8至77.5 mol%)及廢液(75.8至87.9 wt%)的回收所得到液體會在後續批次中重複使用，結果顯示可得到純度為 70.2 至 90.0% 的(S)-(+)-ibuprofen。

在製造過程中，廢物處理是不可避免的。因此，在範例二中，介紹一種在生產含砷的化療針劑過程中所產生的含砷廢水。為了從此廢水中去除砷，開發了一種砷吸附劑由洋菜膠與水合氧化鐵製成。將含有250 μg的As(III) / L的As(III)廢水通過裝有砷吸附劑的管柱，As(III)的濃度可以降低到10 μg的As(III) / L，符合WHO規定的標準。

最後，製藥工程的汙染不會只發生在製造過程中。汙染可能產生在處理過期的藥物之中，因此在範例三中發展出回收未使用的acetaminophen藥錠、 (R,S)-(±)-ibuprofen和As2O3針劑，將從過期的藥物中回收其含有的活性藥物成分。利用固液萃取方法acetaminophen藥錠、 (R,S)-(±)-ibuprofen的回收率分別達到58.7% 及67.6%，而對於隨者蒸發結晶法的發展，As2O3針劑的回收率可達到65.2%至79.9%。所有回收的產品都是具有穩定的晶形以及符合經HPLC所測定的純度標準。

摘要(英)

Due to the ever-increasing awareness of the importance of sustainability, pharmaceutical sector is expected to adopt a sustainable mindset as well. As a means to contribute to those paradigm shift, a series of case studies concerning about developing a sustainable process from the beginning to the end product are presented. In Case I, a method to recycle the spent excess reagent and solvent by slurry reactive crystallization was developed in the chiral resolution of (R,S)-(±)-ibuprofen. The recycle of the resolving agent (56.8 to 77.5 mol%) and spent mother liquor (75.8 to 87.9 wt%) were resulted and reused in subsequent batches, while at the same time, the enriched (S)-(+)-ibuprofen with enantiopurity of 70.2 to 90.0% was produced. However, in reality, waste disposal will be inevitable at some point in a manufacturing process. Therefore, in Case II, an arsenic-containing wastewater produced from the production of an arsenic-based chemotherapeutic agent was presented. To remove arsenic from this wastewater, an arsenic adsorbent made of hydrous ferric oxide impregnated in agarose beads was developed. By passing the wastewater containing 250 μg of As(III) / L of As(III) through a column packed with the adsorbent, the concentration of As(III) could be reduced to 10 μg of As(III) / L of As(III), which was in conformity with the WHO recommended limit. Lastly, pharmaceutical pollution may also happen outside the manufacturing facility. Some of the finished pharmaceutical products may end up being unused, in which its disposal would be problematic. Therefore, in Case III, processes were developed to recycle unused acetaminophen tablets, (R,S)-(±)-ibuprofen tablets, and As2O3 injectables for chemotherapy by salvaging the valuable active pharmaceutical ingredients from those unused drug products. Utilizing a process based on solid-liquid extraction, acetaminophen and (R,S)-(±)-ibuprofen could be recovered with the yield of 58.7 wt% and 67.6 wt%, respectively. For the As2O3 injectables, evaporative crystallization-based protocol was developed, which could recover 65.2 to 79.9 wt% of As2O3. All of those recovered products were recovered in the desired stable crystal form, and were in conformity with the purity standard based on HPLC assay.

關鍵字(中)

★ 永續
★ 回收
★ 手性分析
★ 吸附
★ 藥物

關鍵字(英)

★ Sustainabiity
★ Recycle
★ Chiral Resolution
★ Adsorption
★ Drug Product

論文目次

摘要 i
Abstract iii
Acknowledgement v
Table of Contents vi
List of Figures ix
List of Tables xv
Chapter 1 Introduction 1
1.1 Research Background 1
1.2 Solvent Consumption in Pharmaceutical Industry 3
1.3 Reagent Consumption in Pharmaceutical Industry 6
1.4 Mitigating Pharmaceutical Wastewater Effluents 8
1.5 The Waste of Unused Pharmaceutical Products 10
1.5.1 The Problem of Unused Medications 10
1.5.2 The Impact of Unused Drugs 13
1.5.3 Contents of a Drug Product 15
1.5.4 Drug Recycle 16

Chapter 2 Simultaneous Recycle of Excess Reagent and Solvent by Slurry Reactive Crystallization: The Case of Chiral Resolution of (R,S)-(±)-ibuprofen 18
2.1 Key Points in Chapter 2 18
2.2 Literature Review 19
2.2.1 Slurry Reactive Crystallization 19
2.2.2 Chiral Resolution by Diastereomeric Salt Formation 24
2.2.3 The Necessity of Recycling the Resolving Agent 44
2.2.4 Slurry Reactive Crystallization for a Simultaneous Recycle of Excess Resolving Agent and Solvent 45
2.3 Process Overview 47
2.4 Materials and Methods 50
2.5 Results and Discussions 58
2.5.1 Mechanism of Slurry Reactive Crystallization 58
2.5.2 Construction of the Phase Diagrams 67
2.5.3 Resolution of the Diastereomers 75
2.5.4 Recycling of Resolving Agent and Solvent 80
2.5.5 E-Factor 86
2.6 Conclusions 88

Chapter 3 Mitigation of Arsenic-Containing Wastewater from a Pharmaceutical Manufacturing Process 89
3.1 Key Points in Chapter 3 89
3.2 Literature Review 90
3.2.1 Arsenic as a Pharmaceutical Substance and Pollutant 90
3.2.2 Arsenic-containing Wastewater Treatment Processes 91
3.2.3 Synthesis of Hydrous Ferric Oxide-impregnated Agarose Beads as Arsenic Adsorbent 92
3.3 Materials and Methods 95
3.4 Results and Discussion 102
3.4.1 Characterization of the Synthesized HFO-impregnated Agarose Beads 102
3.4.2 Batch Adsorption-Desorption of As(III) by HFO-impregnated Agarose Beads 106
3.4.3 Removal of As(III) from Pharmaceutical Wastewater by Adsorption in a Packed Column and the Underlying Mechanism 113
3.5 Conclusions 124

Chapter 4 Drug Recycle: Recovery of Active Pharmaceutical Ingredients from Unused Drug Products 125
4.1 Key Points in Chapter 4 125
4.2 Literature Review 126
4.2.1 Background 126
4.2.2 Previous Works of Active Pharmaceutical Ingredient Recovery from Unused Drug Products 127
4.3 Materials 129
4.3.1 Chemicals 129
4.3.2 Drug Products 129
4.3.3 Solvents 130
4.4 Characterizations 130
4.5 Active Pharmaceutical Ingredient Recovery from Solid Dosage Form Drugs: Acetaminophen and (R,S)-(±)-ibuprofen Tablets 132
4.5.1 Initial Solvent Screening and Form Space of Acetaminophen, (R,S)-()-Ibuprofen and Eight Representative Excipients 132
4.5.2 Process Flowchart 134
4.5.3 Recovery of Acetaminophen from Unused Tablets 137
4.5.4 Recovery of (R,S)-(±)-ibuprofen from Unused Tablets 140
4.6 Active Pharmaceutical Ingredient Recovery from Solution Dosage Form Drugs: Arsenic Trioxide Injectables 144
4.6.1 Process Flowchart 145
4.6.2 Recovery of Arsenic Trioxide from Unused Injectables 148
4.7 Conclusions 154

Chapter 5 Conclusions 155
Bibliographies 158
Supplementary Information 195

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指導教授

李度(Tu Lee)

審核日期

2023-1-10

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