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Conversion of Glycerol to Lactic Acid Under Low Corrosive Conditions with Homogeneous and Heterogeneous Catalysts

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Conversion of Glycerol to Lactic Acid Under Low Corrosive Conditions with Homogeneous and Heterogeneous Catalysts University of Tennessee, Knoxville TRACE: Tennessee Research and Creative Exchange Masters Theses Graduate School 8-2011 Conversion of Glycerol to Lactic Acid under Low Corrosive Conditions with Homogeneous and Heterogeneous Catalysts Lu Chen [email protected] Follow this and additional works at: https://trace.tennessee.edu/utk_gradthes Part of the Bioresource and Agricultural Engineering Commons Recommended Citation Chen, Lu, "Conversion of Glycerol to Lactic Acid under Low Corrosive Conditions with Homogeneous and Heterogeneous Catalysts. " Master's Thesis, University of Tennessee, 2011. https://trace.tennessee.edu/utk_gradthes/960 This Thesis is brought to you for free and open access by the Graduate School at TRACE: Tennessee Research and Creative Exchange. It has been accepted for inclusion in Masters Theses by an authorized administrator of TRACE: Tennessee Research and Creative Exchange. For more information, please contact [email protected]. To the Graduate Council: I am submitting herewith a thesis written by Lu Chen entitled "Conversion of Glycerol to Lactic Acid under Low Corrosive Conditions with Homogeneous and Heterogeneous Catalysts." I have examined the final electronic copy of this thesis for form and content and recommend that it be accepted in partial fulfillment of the equirr ements for the degree of Master of Science, with a major in Biosystems Engineering. Xiaofei P. Ye, Major Professor We have read this thesis and recommend its acceptance: Douglas G. Hayes, Qixin Zhong Accepted for the Council: Carolyn R. Hodges Vice Provost and Dean of the Graduate School (Original signatures are on file with official studentecor r ds.) Conversion of Glycerol to Lactic Acid under Low Corrosive Conditions with Homogeneous and Heterogeneous Catalysts A Thesis Presented for the Master of Science Degree The University of Tennessee, Knoxville Lu Chen August 2011 Copyright © 2011 by Lu Chen All rights reserved. ii DEDICATION This Thesis is dedicated to my family. iii ACKNOWLEDGEMENTS I would like to thank my major professor Dr. X. Philip Ye, for giving me this great opportunity in this project, and teaching me how to be a good researcher. I appreciate all the advice and support from my committee members: Dr. Douglas G. Hayes and Dr. Qixin Zhong. Thank you all for serving on my committee. I cannot forget to express appreciation to all my colleagues, Dr. Leming Cheng, Shirley Liu, Yaohua Huang, Dr. Guodong Wen, and Dr. Quansheng Chen, for their consistent assistance, guidance and making my study and stay in University of Tennessee a great experience. Thanks to the undergraduate student Erick Foster for his assistance in some repetitions of the experiments. I wish to thank my best friends both at University of Tennessee (Ran Ye’s family, Ziliang Zhao, Hongtai Yang and Jie Ma), and all over the world (Zifei Yan, Tong Liu, Nan Liu, Tan Su, Erli Zhang, Jilong Ma, Su Tang, Chunyang Li, Xingmin Zhang, and Lingfei Cui), for helping me get through the difficult times, and for all the emotional support, entertainment, and caring they provided. Last, and most importantly, I feel a great appreciation to my parents. They bore me, raised me, supported me, taught me, and loved me. To them I dedicate this thesis. iv ABSTRACT With the increasing demand for biodiesel, the accumulation of byproduct, crude glycerol has become a problem which needs to be solved. Lactic acid is one of the value-added chemical which can be produced from glycerol that has wide uses in food and chemical industry. Although glycerol can be converted to lactic acid with an alkali as the catalyst at high glycerol conversion (100 mol%) and lactic acid yield (around 90 mol%), the high alkalinity would cause severe corrosiveness to a stainless steel reactor. In this study two tasks were performed to convert glycerol to lactic acid with satisfactory conversion and selectivity, and to reduce the corrosiveness of reaction medium. First, CaO was used as solid base catalyst. The highest lactic acid yield achieved was 40.8 mol% with a 97.8 mol% glycerol conversion, when operating at 290°C after 150 min reaction with molar ratio of CaO: glycerol=0.3. Also CaO has advantages such as high lactic acid productivity (3.35 g/(min·L)) and reusability. Meanwhile, CaO can be used as the catalyst for both biodiesel production and the following crude glycerol conversion to lactic acid. Second, for glycerol conversion with NaOH as catalyst, a fed-batch reactor was applied to continuously supply NaOH during reaction process, compensating the OH- neutralized by newly formed lactic acid. The optimal lactic acid yield of 80.5 mol%, with 92.8% glycerol conversion was obtained at 300 °C for 220min, with 1.1 M glycerol initial concentration. A first-order kinetic model for glycerol concentration versus time was developed and verified experimentally under v conditions with different initial glycerol concentration and reaction temperature. Although crude glycerol samples contained large amount of impurities, both methods, conversion with solid base catalyst and with fed-batch reactor, were applied successfully to three crude glycerol samples provided by biodiesel manufacturers, and the lactic acid yield reached 52.3 mol% and 72.7 mol% respectively. Finally, the corrosion issue of different methods was compared based on the Fe3+ concentration (analyzed with atomic-absorption spectroscopy) in the products. Both methods of glycerol conversions, with solid base catalyst and fed- batch reactor, can reduce the corrosiveness of glycerol conversion with an alkali as the catalyst. vi TABLE OF CONTENTS Chapter 1 Introduction and Objectives .................................................................. 1 1.1 Biodiesel industry and its excessive co-product - crude glycerol ................. 1 1.2 The exploitation of crude glycerol ................................................................ 3 1.3 Lactic acid production processes and their drawbacks ............................... 6 Objectives ......................................................................................................... 9 Chapter 2 Literature Review ............................................................................... 10 2.1 Properties of crude glycerol ....................................................................... 10 2.2 Conversion of glycerol to lactic acid with homogeneous catalyst .............. 11 2.2.1 Predicted pathway .................................................................................. 12 2.2.2 The function of metal ions and OH- group .............................................. 13 2.2.3 Disadvantages of the glycerol conversion on homogeneous catalyst .... 14 2.2.4 Modifications of the glycerol conversion with homogeneous catalyst ..... 14 2.3 Feasibility of fed-batch process with homogeneous catalyst ..................... 20 2.4 Solid base catalysts and the advantages .................................................. 21 2.4.1 Advantages comparing with homogeneous catalysts ............................. 22 2.4.2 Types of solid base catalysts .................................................................. 22 2.5 Conclusion ................................................................................................. 25 Chapter 3 Conversion of Glycerol to Lactic Acid Using Calcium Oxide as Solid Base Catalyst ...................................................................................................... 26 Abstract ........................................................................................................... 26 3.1 Introduction ................................................................................................ 27 Objectives ....................................................................................................... 28 3.2 Materials and methods .............................................................................. 29 3.2.1 Materials and catalyst preparation ...................................................... 29 3.2.2 Reactors ............................................................................................. 29 3.2.3 Reaction procedures ........................................................................... 31 3.2.4 Experimental design ........................................................................... 34 3.3 Results and discussion .............................................................................. 36 3.3.1 Conversion of glycerol solution with different solid base catalysts ...... 36 3.3.2 Glycerol (without water) conversion with CaO .................................... 37 3.3.3 Effect of reaction temperature on lactic acid yield ............................... 39 3.3.4 Effect of molar ratio of CaO to glycerol on lactic acid yield ................. 40 3.3.5 Evaluation of mass balance ................................................................ 41 3.3.6 Activation energy of glycerol conversion with CaO as catalyst ........... 43 3.3.7 Effect of regeneration and reuse ......................................................... 43 3.3.8 Effect of water content on the lactic acid yield .................................... 45 3.3.9 Application of CaO in crude glycerol (different sources) conversion to lactic acid ..................................................................................................... 47 3.3.10 Structure-function of the CaO on the lactic acid yield ....................... 48 3.3.11 Production of biodiesel and lactic acid from soybean oil over CaO .. 51 3.4 Conclusions
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