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the synthesis of lubricant additives from waste commodity polymers gregory james hunt PDF

220 Pages·2012·4.99 MB·English
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T S O L HE YNTHESIS F UBRICANT A F W DDITIVES ROM ASTE C P OMMODITY OLYMERS B Y G J H REGORY AMES UNT i THE SYNTHESIS OF LUBRICANT ADDITIVES FROM WASTE COMMODITY POLYMERS Thesis submitted for the degree of: “Doctor of Philosophy”, PhD From work conducted in the Department of Chemistry at the University of Durham and at the BP Technology Centre, BP PLC. The work was funded by the Engineering and Physical Sciences Research Council, UK, and BP PLC, UK, by a CASE doctoral training award. ii Further financial support was generously provided by: Collingwood College at the University of Durham Royal Society of Chemistry Macro Group UK iii STATEMENT OF COPYRIGHT The copyright of this thesis rests with the author unless referenced within the text where copyright rests with the original holder. No quotation from it should be published without his written consent and information derived from it should be acknowledged. iv DECLARATION The work reported in this thesis was carried out in the Department of Chemistry at the University of Durham, Durham, UK and the BP Technology Centre, Pangbourne, UK between October 2006 and March 2010. All the work was carried out by the author unless otherwise stated, and has not previously been submitted for a degree at this or any other University. v Acknowledgements Firstly, I must express my deepest gratitude to Prof. Neil Cameron who has always been on hand to guide, discuss and encourage with his expertise and for allowing me to attend an array of meetings and conferences. Neil’s limitless patience in the writing of this Thesis also requires acknowledgement. Having benefited from working in CG169 and CG234 there are many to thank; Dr. Matt Gibson (Gibbo) for setting me straight during my Masters project and for his organic chemistry skill. Dr’s Fransico-Fernadez Trillo, Jon Fay and Sebastian Spain for all their insights into organic and polymer chemistry. David Ward Johnson (the Johnson) for many interesting conversations and being the butt of so many jokes. Kimmins for his enthusiasm and many a good night out in the New Inn or Spice Lounge. Paco, Gerledine and the Germans are thanked for the multitude of language lessons by the fume cupboards. Dr. Alison Parry for all her expertise and help, not to mention her impressive whistling skills. Dr. Ross Carnachan is thanked for providing so many memories, most notably the iPod/laptop incident and being the sole consistent member of the group during my time in Durham. Caroline is thanked for spicing up the dynamics of the lab, as is Lauren Cowie for her enthusiasm and wit. Dr Lian Hutchings is thanked for all his discussions regarding SEC, and for not getting too mad after running it dry. Dr. Richard Thompson for running the Ion beam experiments. All the analytical staff, Alan, Ian, Mike, Jackie and Aileen. Special mention should be made to Scott, Jon, Johnson and Lauren for providing me with friendship and encouragement which made weekend chemistry fun! vi Dr. Gordon Lamb is thanked for all this patience and encouragement of new ideas and for making my time in Pangbourne so enjoyable. Dr. Andrew Smith for all his insights into chemistry. I must thank my parents Eileen and Robert for all their help and support. Finally, I must thank my fiancée Rachel; I couldn’t have done it without you! vii Table of Contents INTRODUCTION: ASPECTS OF POLYMER SCIENCE; SYNTHESIS, DEGRADATION AND LUBRICATION. ....................................................................................... 1 AIMS AND OBJECTIVES ............................................................................................ 2 FUNDAMENTALS OF POLYMER SCIENCE ...................................................................... 2 What is a polymer? ....................................................................................... 2 How are polymers classified? ....................................................................... 3 What are the common features of a polymer? ............................................ 4 Classification according to method of manufacture .................................... 5 POLYMER DEGRADATION ....................................................................................... 13 Methods of degradation ............................................................................. 14 Thermal Degradation .................................................................................. 16 Chemical Degradation ................................................................................ 19 Catalytic Degradation ................................................................................. 19 Superacids ................................................................................................... 22 Biological Degradations .............................................................................. 23 Photodegradation[47] ................................................................................ 25 Microwave degradation ............................................................................. 26 Ultrasonic degradation[46, 48]................................................................... 26 Mechanical degradation[48] ...................................................................... 27 Use of Reactors ........................................................................................... 27 LUBRICANT FORMULATION..................................................................................... 29 Basics of Lubrication ................................................................................... 29 Lubricant Additives ..................................................................................... 37 The Final Lubricant ...................................................................................... 47 GENERATION OF FUNCTIONAL MATERIALS FROM WASTE PLASTIC ............... 48 INTRODUCTION .................................................................................................... 49 RESULTS AND DISCUSSION ..................................................................................... 50 Initial investigation: the use of microwave assisted pyrolysis with a CEM Discover Microwave Reactor ...................................................................... 50 viii Biotage Initiator 60 Microwave pyrolysis system ....................................... 59 Recycling of expanded polystyrene using Biotage Initiator 60 Microwave pyrolysis system .......................................................................................... 72 CONCLUSIONS ..................................................................................................... 78 EXPERIMENTAL SECTION ........................................................................................ 79 General ........................................................................................................ 79 Methods ...................................................................................................... 80 LUBRICANT COMPONENTS FROM WASTE POLYSTYRENE AND CONVENTIONAL SOURCES ..................................................................................................... 83 INTRODUCTION .................................................................................................... 84 Copolymerisation of maleic anhydride and styrene ................................... 85 RESULTS AND DISCUSSION ..................................................................................... 93 Effect of maleic anhydride on the fragmentation of cumyl dithiobenzoate. .................................................................................................................... 99 Maleic anhydride addition to a Macro-RAFT agent. ................................ 104 Stearyl methacrylate copolymers ............................................................. 114 Polymerisation with N-maleimides ........................................................... 119 Coupling reactions .................................................................................... 122 Reactions with degraded polystyrene ...................................................... 126 Microwave assisted synthesis of maleimides. .......................................... 129 EXPERIMENTAL SECTION ...................................................................................... 131 General ...................................................................................................... 131 Monomer synthesis .................................................................................. 132 Macro-monomer synthesis. ...................................................................... 133 Chain Transfer agent synthesis. ................................................................ 133 Polymer Synthesis ..................................................................................... 136 Post synthetic functionalisations .............................................................. 139 CONCLUSIONS ................................................................................................... 142 TESTING OF LUBRICANT COMPONENTS FROM WASTE POLYSTYRENE AND CONVENTIONAL SOURCES ......................................................................... 144 ix INTRODUCTION .................................................................................................. 145 RESULTS AND DISCUSSION ................................................................................... 145 Solubility .................................................................................................... 147 Dispersancy ............................................................................................... 150 Viscosity characteristics ............................................................................ 162 Thermal and Oxidative stability ................................................................ 166 EXPERIMENTAL .................................................................................................. 169 Rheological Testing ................................................................................... 169 Kinematic Viscosity ................................................................................... 169 Oxidation and thermal stability ................................................................ 169 CONCLUSIONS ................................................................................................... 170 CONCLUSIONS AND FUTURE WORK ........................................................... 173 CONFERENCE PRESENTATIONS .............................................................................. 178 CONFERENCE ATTENDANCE (NON-PRESENTER) ........................................................ 178 AWARDS AND BURSARIES .................................................................................... 179 REFERENCES ...................................................................................................... 180 x

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for his organic chemistry skill. Dr's Fransico-Fernadez Trillo, Jon Fay and. Sebastian Spain for all their insights into organic and polymer chemistry.
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