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Callison, June (2011) the Investigation of a Side Reaction Leading to Colour Formation in a Polyurethane Production Chain

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Callison, June (2011) the Investigation of a Side Reaction Leading to Colour Formation in a Polyurethane Production Chain Callison, June (2011) The investigation of a side reaction leading to colour formation in a polyurethane production chain. PhD thesis. http://theses.gla.ac.uk/2498/ Copyright and moral rights for this thesis are retained by the author A copy can be downloaded for personal non-commercial research or study, without prior permission or charge This thesis cannot be reproduced or quoted extensively from without first obtaining permission in writing from the Author The content must not be changed in any way or sold commercially in any format or medium without the formal permission of the Author When referring to this work, full bibliographic details including the author, title, awarding institution and date of the thesis must be given Glasgow Theses Service http://theses.gla.ac.uk/ [email protected] The Investigation of a Side Reaction Leading to Colour Formation in a Polyurethane Production Chain June Callison For the degree of Doctor of Philosophy Department of Chemistry April 2011 ii Declaration The work contained in this thesis, submitted for the degree of Doctor of Philosophy is my own original work, except where due reference is made to other authors and has not been previously submitted for a degree at this or any other university. June Callison June Callison 2011 iii Abstract In the industrial synthesis of 4,4’-methylene diphenyl diisocyanate (MDI), an unwanted side reaction between the product and the starting material, 4,4’-methylene dianiline, can lead to the formation of ureas. It has been postulated these ureas undergo further reaction with phosgene to produce a precursor to chlorine radicals, which could then attack the MDI backbone forming conjugated systems that would promote colour in the final products. To investigate this process model compounds including 4-benzylaniline (4-BA) and 1,3- diphenylurea were used as starting materials. The reactions carried out showed the phosgenation of the urea forms a chloroformamidine-N-carbonyl chloride (CCC) which upon heating > 303 K can break down to form an isocyanide dichloride (ID). Conventional synthesis routes were used to gain high yields of p-tolyl and phenyl isocyanide dichlorides in order to analyse the compounds. It was found that upon heating to 453 K or irradiating the isocyanide dichlorides in the process solvent (chlorobenzene) coloured solutions were formed; with the presence of MDI and oxygen increasing the intensity of the colouration. Electron paramagnetic resonance spectroscopy was used to gain information on the use of isocyanide dichlorides as a source of chlorine radicals. Using N-tert-butyl--phenylnitrone (PBN) as a spin trap, an 8 line spectra relating to the chlorine adduct was measured confirming the production of Cl. Throughout the project side reactions involving the formation of carbodiimide from CCC and a secondary route for the phosgenation of the urea to the isocyanate have been investigated and are presented within a global reaction scheme. It was also found the ureas were only partially soluble in the process solvent leading to research into the structure of three different urea molecules and the proposal of a modified reaction scheme. iv Acknowledgements I would like to thank everyone involved in this project and to those that have helped me throughout my years at university. Special thanks to my supervisor Dr David Lennon for all the support and guidance over the years. Thank you for having faith in me, for all the good advice and for the intriguing conversations in the pub. To Prof John Winfield, thank you for sharing your immense knowledge and all your help throughout this project. It has been a pleasure working with you. Thank you to my industrial sponsors Huntsman Polyurethanes for providing an interesting project to work on. To my supervisor Rob Carr and to Archie Eaglesham thanks for the informative meetings and for being approachable when I needed advice. Thanks to Willem van der Borden, Klaas van der Velde and Kimberly de Cuba for the help in carrying out the experiments at the Huntsman Polyurethanes Process Research and Development Laboratory and for the support and friendship during my short stay in Rozenburg. Also for the wonderful meals, beer and introducing me to Frikandellen. Thanks to Franziska Betzler and Andrew Farrell, who carried out work associated with this project through undergraduate projects. From the University of Manchester thanks to Dr Ruth Edge for help in carrying out the EPR measurements. Prof David Collison and Prof Eric Mcinnes for the advice and expertise and to Dr Joseph McDouall for carrying out the DFT calculations. Thanks to Alex Burns for the advice on the safety aspects of this work, to Dr Louis Farrugia for helping with the crystallographic studies and to Dr David Adam for help with the NMR work. To Emma, Neil, Ian, Liam and Andrew thanks for the great times in the lab and in the pub. Especially to Emma for showing me the ropes and putting up with my questions. Plus a special mention to Franziska and Niko for being great hosts on our trip to Oktoberfest. Also to my friends, you know who you are, thank you for being there. And finally to Mum, Dad and James thank you for all your love, patience, and support throughout the years. v “You are here to learn the subtle science and exact art of potion-making. I don’t expect you will really understand the beauty of the softly simmering cauldron with its shimmering fumes, the delicate power of liquids that creep through human veins, bewitching the mind, ensnaring the senses ... I can teach you how to bottle fame, brew glory, even stopper death.” Professor Severus Snape, Harry Potter and the Philosopher’s Stone vi Contents 1 Introduction......................................................................................................................... 2 1.1 Polyurethanes in Industry ............................................................................................. 2 1.2 Isocyanates .................................................................................................................. 2 1.3 MDI Production............................................................................................................. 3 1.4 Phosgene ..................................................................................................................... 6 1.4.1 Triphosgene ......................................................................................................... 7 1.5 New Methods for MDI Synthesis ................................................................................... 9 1.6 Colouration Problems ................................................................................................. 10 1.7 Postulated Reaction Scheme ...................................................................................... 11 1.8 Urea Compounds ....................................................................................................... 12 1.8.1 Crystal Structure ................................................................................................ 13 1.8.2 Tautomerism ...................................................................................................... 13 1.9 Analytical Techniques ................................................................................................. 14 1.9.1 Electron Paramagnetic Resonance (EPR) Spectroscopy .................................... 14 1.9.2 Infrared Spectroscopy ........................................................................................ 15 1.9.3 Ultraviolet and Visible Absorption Spectroscopy ................................................. 16 2 Experimental ..................................................................................................................... 19 2.1 Chemicals .................................................................................................................. 19 2.2 Apparatus for Synthesis Reactions ............................................................................. 20 2.2.1 Phosgenation ..................................................................................................... 21 2.2.2 Chlorination ........................................................................................................ 26 2.3 Characterisation Techniques ...................................................................................... 27 2.3.1 Fourier Transform Infrared (FTIR) Spectroscopy ................................................ 27 2.3.2 Nuclear Magnetic Resonance (NMR) Spectroscopy ........................................... 27 2.3.3 Elemental Analysis ............................................................................................. 27 2.3.4 Melting Point Determination ............................................................................... 28 2.3.5 Thermal Analysis................................................................................................ 28 2.3.6 Available Chlorine .............................................................................................. 28 2.3.7 Mass Spectrometry (MS) .................................................................................... 31 2.3.8 Gas Chromatography-Mass Spectrometry (GCMS) ............................................ 31 2.3.9 Gel Permeation Chromatography (GPC) ............................................................ 31 2.3.10 Yellow Index ...................................................................................................... 31 2.3.11 UV/Vis Spectroscopy.........................................................................................
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