利用異相催化劑對鄰苯二甲酸二辛酯、PBT 和 PET 進行更綠色的氫化反應

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研究生：	阿維納什 Lende, Avinash B.
論文名稱：	利用異相催化劑對鄰苯二甲酸二辛酯、PBT 和 PET 進行更綠色的氫化反應 Greener Hydrogenation of Dioctyl Phthalate, PBT and PET Using Heterogeneous Catalysts
指導教授：	談駿嵩 Tan, Chung-Sung
口試委員:	蔡德豪 Tsai, De-Hao 潘詠庭 Pan, Yung-Tin 陳郁文 Chen, Yu-Wen 蔣孝澈 Chiang, Anthony S. T.
學位類別：	博士 Doctor
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2021
畢業學年度：	109
語文別：	英文
論文頁數：	190
中文關鍵詞：	氢化、氢化、多相催化剂、PBT 、PET 、DOP
外文關鍵詞：	Hydrogenation, Hydrogenation, Heterogeneous catalyst, PBT, PET, DOP
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本研究證實芳香環在多相催化劑上選擇性加氫並製造環保產品，加氫產品對精細化工、聚合物、石油及燃料工業的生產相當重要，因此對於芳香環氫化研究的需求大量增加。本研究在不同的反應溫度、反應時間、H2壓力、CO2壓力、載體、單金屬和雙金屬基多相催化劑，以及不同的金屬附載量下進行反應。研究出三種反應系統: 無溶劑下的磷苯二甲酸二辛酯(DOP)氫化反應、聚對苯二甲酸乙二醇酯(PET)和聚對苯二甲酸丁二醇酯(PBT)使用1,1,1,3,3,3-六氟-2-丙醇 (HFIP) 和水作為溶劑。
透過化學流體沉積 (CFD) 將 Rh 摻入鋁改性的中孔泡沫 (MCF) 中，藉此開發了一種新型催化劑，用於將 DOP 選擇性加氫成環保增塑劑六氫鄰苯二甲酸二(2-乙基己基)酯 (DEHHP)。含有 5 和 1 wt% Rh 的 Si/Al 摩爾比的 Al 改性 MCF 在 80 °C 和 1000 psi H2 壓力下實現了 100% DOP 向 DEHHP 的轉化，反應時間為 60 分鐘。當 Al 加入 MCF 載體時，Rh 與載體的相互作用變得更強。通過密切監測 Si/Al 比來有效控制 Al 提供的酸度是提高 Rh/Al-MCF 催化劑催化活性的關鍵。含有Si/Al 莫耳為 5 和 1 wt% Rh 的 Al 改性 MCF 在 80 °C 和 1000 psi H2 壓力下完成了 100% DOP 向 DEHHP 的轉化，反應時間為 60 分鐘，當 Al 加入 MCF 載體時，Rh 與載體的相互作用變得更強，通過密切監測 Si/Al 比來有效控制 Al 提供的酸度是提高 Rh/Al-MCF 催化劑催化活性的關鍵。
使用多元醇合成法合成的 Vulcan XC-72 負載的 Rh-Pt 雙金屬催化劑，將溶解在 HFIP 中的 PET 和 PBT 直接氫化成環保聚酯 PECHD 和 PBC。使用多元醇合成方法生成的催化劑載體表面上存在的 RhOx 物質促進了 PET 和 PBT 的氫化，與單金屬 Rh 催化劑相比，發現 Rh-Pt 雙金屬催化劑更適合加氫系統，主要是因為Rh 的強大芳香環吸附能力與 Pt 增加的 H2 溢出同時作用。在 1000 psi 的 H2 壓力和 50℃條件下進行60 分鐘，在 Rh-Pt 雙金屬催化劑上使 PET 完全氫化為 PECHD 和 PBT 為 PBC，其理論 Rh 和 Pt 金屬負載量為 2.5 wt%，並發現在氫化後使用壓縮的 CO2 反溶劑技術可大幅回收 PECHD 和 PBC。
本研究提出以水為溶劑和 SBA-15 負載的 Rh-Pt 雙金屬催化劑各 2.5 wt%對 PET 和 PBT 進行氫化，該催化劑是使用 CFD 合成，並以超臨界 CO2 作為溶劑。發現 Rh 和 Pt 奈米粒子在 Rh 和 Pt 前驅體氫還原後，均勻分散在 SBA-15 的孔內。雖然 PET 和 PBT 不溶於水，但因為水上反應機制，且在劇烈攪拌下，兩者都可以分別完全轉化為 PECHD 和 PBC。由於 Rh-Pt 協同作用，雙金屬催化劑 Rh2.5Pt2.5/SBA-15 呈現出比單金屬 5.0 wt% Rh 催化劑更高的催化活性，正如文獻中的第一性原理密度泛函理論計算所提出的。Rh-Pt 協同作用被認為是PET中芳香環和 PBT在Pt(111) 上的有利吸附的組合，使它們易於被 Rh 選擇性氫化，以及降低 Rh-Pt 表面上 H2的結合能合金奈米粒子，導致在 Rh-Pt合金納米粒子表面的 H2 溢出的活化能降低。透過對反應參數的研究，發現 90 °C 的溫度、1000 psi 的 H2 壓力和 80 分鐘的反應時間是完成 100% 加氫的最佳反應條件。可以從中得知製備PECHD和PBC的傳統方法相當繁瑣且耗能，涉及對苯二甲酸（TPA）通過酯化轉化為對苯二甲酸二甲酯（DMT），然後進行加氫生成1,4-環己二甲酸二甲酯（ DMCD) 進一步將 DMCD 加氫生成 1, 4-環己烷二甲酸 (CHDA) 和 1,4- 環己烷二甲醇 (CHDM)。1,2-乙二醇（EDO）和1,4-丁二醇（BDO）與CHDA的酯化和隨後的聚合反應最終分別產生PECHD和PBC。
本研究為這些製備的催化劑使用各種催化劑表徵工具進行表徵，以了解催化劑的物理和化學性質，並研究了幾個反應參數以得知最有利的反應條件。

In this thesis, the selective hydrogenation of aromatic ring to environmentally friendly products over heterogenous catalysts were demonstrated. The hydrogenated products are important for the production of fine chemicals, polymers, petroleum and fuel industry. Therefore, the demand to perform more research on hydrogenation of aromatic ring has increased. The reactions performed in this thesis were carried out at different reaction temperature, reaction time, H2 pressure, CO2 pressure, supports, mono and bimetallic based heterogenous catalysts with varying metals loading amount. Three reaction systems were investigated: hydrogenation of dioctyl phthalate (DOP) without solvent, polyethylene terephthalate (PET) and polybutylene terephthalate (PBT) using 1,1,1,3,3,3-hexafluro-2-propanol (HFIP) as solvent and water as solvent.
A new catalyst was developed for the selective hydrogenation of DOP to environmentally friendly plasticizer di(2-ethylhexyl) hexahydrophthalate (DEHHP) by incorporating Rh via chemical fluid deposition (CFD) into an Al-modified mesocellular foam (MCF). The Al-modified MCF containing a Si/Al molar ratio of 5 and 1 wt% Rh achieved 100% conversion of DOP to DEHHP with no side products at 80 °C and 1000 psi H2 pressure for 60 min reaction time. The interaction of Rh with the support became stronger when Al was incorporated onto the MCF supports. An effective control of the acidity provided by Al by closely monitoring the Si/Al ratio was key in improving the catalytic activity of Rh/Al-MCF catalysts.
The direct hydrogenation of PET and PBT dissolved in HFIP to environmentally friendly polyesters PECHD and PBC respectively, using a Vulcan XC-72 supported Rh-Pt bimetallic catalyst synthesized via a polyol method. The hydrogenation of PET and PBT was promoted by RhOx species present on the catalyst support surface which was generated using the polyol synthesis method. As compared to the monometallic Rh catalyst, the Rh-Pt bimetallic catalyst was found to be superior for hydrogenation system. This superiority was attributed to the strong aromatic ring adsorption ability of Rh working in synergy with an increased H2 spillover by Pt. At a H2 pressure of 1000 psi and 50 oC for 60 min, complete hydrogenation of PET to PECHD and PBT to PBC were achieved over the Rh-Pt bimetallic catalyst possessing theoretical Rh and Pt metal loadings of 2.5 wt% each. PECHD and PBC was found to be recovered to a very high extent using the compressed CO2 anti-solvent technique after hydrogenation.
The hydrogenation of PET and PBT were also proposed in this thesis using water as the solvent and an SBA-15-supported Rh−Pt bimetallic catalyst (2.5 wt % each). The catalyst was synthesized using CFD in which supercritical CO2 was used as the solvent. Rh and Pt nanoparticles were found to be uniformly dispersed inside the pores of SBA-15 after hydrogen reduction of the Rh and Pt precursors. Though PET and PBT were not soluble in water, both could be completely converted to PECHD and PBC respectively, under vigorous stirring owing to the advent of an on-water mechanism. The bimetallic catalyst Rh2.5Pt2.5/SBA-15 showed higher catalytic activity over the monometallic 5.0 wt% Rh catalyst due to the Rh−Pt synergy, as proposed by first principles density functional theory calculations in open literature. The Rh−Pt synergy was proposed as a combination of favorable adsorption of aromatic rings in PET and PBT on Pt(111), making them susceptible for selective hydrogenation by Rh, and a lowering of binding energy for H2 on the surface of Rh−Pt alloy NPs, thereby leading to a subsequent reduction in the activation energy for the H2 spillover on the surface of Rh−Pt alloy NPs. Through a systematic study of reaction variables, a temperature of 90 °C, a H2 pressure of 1000 psi, and a reaction time of 80 min were found to be the optimal reaction conditions at which 100% hydrogenation could be achieved. It can be seen that the conventional means to prepare PECHD and PBC were quite tedious and energy intensive, involving the conversion of terephthalic acid (TPA) to dimethyl terephthalate (DMT) via esterification and undergoes subsequent hydrogenation to produce dimethyl 1,4-cyclohexanedicarboxylate (DMCD) further the hydrogenation of DMCD yields both 1, 4-cyclohexanedicarboxylic acid (CHDA) and 1,4-cyclohexanedimethanol (CHDM). The esterification and subsequent polymerization reactions of 1,2-ethanediol (EDO) and 1,4-butandiol (BDO) with CHDA finally produced PECHD and PBC respectively.
The catalysts prepared for these studies, presented in this thesis were characterized using various catalyst characterization tools to understand the physical and chemical properties of the catalysts, and several reaction variables were studied to obtain the most favourable reaction conditions.

Table of Contents
Cover Page                                                                                                            I
Acknowledgments                                                                                               II
Abstract (Chinese)                                                                                               IV
Abstract (English)                                                                                               VII
Table of Contents                                                                                               X
List of Tables                                                                                                       XIV
List of Figures                                                                                                       XVI
List Publications                                                                                                       XXI
List of Abbreviations                                                                                               XXIII
Objectives                                                                                                               XXV

Chapter 1. Introduction                                                                                             1
1 Catalysis                                                                                                                1
2 The importance of catalytic reactions                                                             3
3 Dioctyl phthalate                                                                                                     4
4 Polybutylene terephthalate                                                                             5
5 Polyethylene terephthalate                                                                             6
6 “On-water” mechanism                                                                                     7
7 Hydrogenation of aromatic ring                                                                     8

Chapter 2. Literature Review                                                                                     9
1 Catalysts                                                                                                                9
1.1 SiO2 based supported catalysts                                                                      9
1.2 Carbon based supported catalysts                                                            10
1.3 Chemical fluid deposition                                                                            11
2 Characterisation of catalyst                                                                               12
3 Dioctyl phthalate                                                                                             12
4 Polybutylene terephthalate                                                                            16
5 Polyethylene terephthalate                                                                            20
6 Hydrogenation of PBT and PET                                                                    22
7 Hydrogenation of aromatic ring                                                                    26
7.1 Aromatic hydrogenation mechanism                                                            27

Chapter 3. Hydrogenation of Dioctyl Phthalate                                                   28
1 Introduction                                                                                                      28
2 Materials                                                                                                            29
3 Methods                                                                                                              29
3.1 Catalyst preparation                                                                                       29
3.2 Catalyst characterizations                                                                              33
3.3 Catalytic hydrogenation                                                                                 35
4 Results and discussions                                                                                        36
4.1 Physical properties of the supports and catalysts                                      36
4.2 Chemical properties of the supports and the catalysts                             42
4.3 Effect of porous catalyst supports                                                                 45
4.4 Effect of surface modification                                                                       48
4.5 Effect of reaction temperature                                                                       49
4.6 Effect of H2 pressure                                                                                     49
5 Conclusions                                                                                                            51
Chapter 4. Hydrogenation of Polybutylene Terephthalate, HFIP as Solvent
1 Introduction                                                                                                       53
2 Materials                                                                                                               59
3 Methods                                                                                                               60
3.1 Catalyst preparations                                                                                  60
3.2 Catalyst characterizations                                                                            61
3.3 Catalytic hydrogenation                                                                               63
3.4 Separation of product                                                                                  64
4 Results and discussion                                                                                          64
4.1 Physical and chemical properties of materials                                            64
4.2 Separation and analysis of product                                                              75
4.3 Effect of catalyst supports                                                                           79
4.4 Effect of catalyst synthesis methods                                                            80
4.5 Effect of monometallic and bimetallic catalysts                                         81
4.6 Effect of temperature                                                                                   84

4.7 Effect of H2 pressure                                                                                   84
4.8 Effect of reaction time                                                                                 86
4.9 Effect of PBT concentration                                                                        86
4.10 Characterization of product                                                                       87
5 Conclusion                                                                                                               92

Chapter 5. Hydrogenation of Polyethylene Terephthalate, HFIP as Solvent
1 Introduction                                                                                                       93
2 Materials                                                                                                            96
3 Methods                                                                                                               97
3.1 Catalyst preparations                                                                                     97
3.2 Catalyst characterizations                                                                            98
3.3 Catalytic hydrogenation                                                                               99
3.4 Separation of product                                                                                  100
4 Results and discussion                                                                                          101
4.1 Physical and chemical properties of the materials                                    101
4.2 Separation and analysis of product                                                            107
4.3 Effect of porous catalyst supports                                                            109
4.4 Effect of catalyst synthesis methods                                                            110
4.5 Effect of monometallic and bimetallic catalysts                                    111
4.6 Effect of temperature                                                                                    112
4.7 Effect of H2 pressure                                                                                   113
4.8 Effect of reaction time                                                                                 114
4.9 Effect of PET concentration                                                                            114
5 Conclusion                                                                                                            116

Chapter 6. Hydrogenation of Polyethylene Terephthalate, Water as Solvent
1 Introduction                                                                                                      117
2 Materials                                                                                                             120
3 Methods                                                                                                             121
3.1 Synthesis of SBA-15                                                                                     121
3.2 Synthesis of catalyst                                                                                     122

3.3 Catalyst characterizations                                                                            123
3.4 Catalytic hydrogenation                                                                               124
3.5 Design of experiment                                                                                  126
4 Results and discussion                                                                                          127
4.1 Physical and chemical properties of catalysts                                             127
4.2 Control experiments for the hydrogenation of PET                                    130
4.3 Analysis of product                                                                                      133
4.4 Hydrogenation of PET to PECHD using Rh-Pt                                          137
4.5 Optimization of reaction conditions                                                            139
4.6 Catalyst recycle study                                                                                  140
5 Conclusion                                                                                                         144

Chapter 7. Hydrogenation of Polybutylene Terephthalate, Water as Solvent
1 Introduction                                                                                                            145
2 Materials                                                                                                              150
3 Methods                                                                                                              151
3.1 Synthesis of SBA-15                                                                                     151
3.2 Synthesis of catalyst                                                                                      151
3.3 Catalyst characterizations                                                                            152
3.4 Catalytic hydrogenation                                                                               154
3.5 Design of experiment                                                                                  155
4 Results and discussion                                                                                          156
4.1 Physical and chemical properties of catalyst                                              156
4.2 Control experiments for the hydrogenation of PBT                                    160
4.3 Analysis of product                                                                                      163
4.4 Hydrogenation of PBT to PBC using Rh-Pt                                                167
4.5 Optimization of reaction conditions                                                            169
4.6 Catalyst recycle study                                                                                  170
5 Conclusion                                                                                                                173

Chapter 8. Conclusions                                                                                               174
Chapter 9. References                                                                                             176

                                

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