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Synthesis and Characterization of Toluene Diisocyanate

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Synthesis and Characterization of Toluene Diisocyanate SYNTHESIS AND CHARACTERIZATION OF TOLUENE DIISOCYANATE A THESIS SUBMITTED TO THE GRADUATE SCHOOL OF NATURAL AND APPLIED SCIENCES OF MIDDLE EAST TECHNICAL UNIVERSITY BY AYŞEGÜL HİSAR TELLİ IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE IN CHEMISTRY NOVEMBER 2014 Approval of the thesis: SYNTHESIS AND CHARACTERIZATION OF TOLUENE DIISOCYANATE submitted by AYŞEGÜL HİSAR TELLİ in partial fulfillment of the requirements for the degree of Master of Science in Chemistry Department, Middle East Technical University by, Prof. Dr. Gülbin Dural Ünver _____________________ Dean, Graduate School of Natural and Applied Sciences Prof. Dr. İlker Özkan _____________________ Head of Department, Chemistry Prof. Dr. Özdemir Doğan _____________________ Supervisor, Chemistry Dept., METU Examining Committee Members: Prof. Dr. Cihangir Tanyeli _____________________ Chemistry Dept., METU Prof. Dr. Özdemir Doğan _____________________ Chemistry Dept., METU Prof. Dr. Metin Zora _____________________ Chemistry Dept., METU Prof. Dr. Adnan Bulut _____________________ Chemistry Dept., Kırıkkale University Dr. E. Görkem Günbaş _____________________ Chemistry Dept., METU Date: 28.11.2014 I hereby declare that all information in this document has been obtained and presented in accordance with academic rules and ethical conduct. I also declare that, as required by these rules and conduct, I have fully cited and referenced all material and results that are not original to this work. Name, Last name: Ayşegül Hisar Telli Signature: iv ABSTRACT SYNTHESIS AND CHARACTERIZATION OF TOLUENE DIISOCYANATE Hisar Telli, Ayşegül M.S., Department of Chemistry Supervisor: Prof. Dr. Özdemir Doğan November 2014, 52 pages Toluene diisocyanate (TDI) is one of the important components of solid rocket propellants. It is used for the construction of polyurethane network by reacting with hydroxy terminated polybutadiene (HTPB) and functions as a curing agent. The aim of project, supported by Ministry of Science Industry and Technology under SANTEZ program in collaboration with ROKETSAN, is to synthesize TDI at laboratory scale by determining the best method/methods that give the product in high yield with desired isomer ratio and quality. Although TDI is in industrially important compound, most of the studies concerning the synthesis of this compound are patented. To the best of our knowledge, TDI is not produced in Turkey and there is no study related to the production of this chemical. In this project TDI synthesis was planned in three steps which are nitration of toluene, reduction of dinitrotoluene, and phosgenation of toluenediamine. Standard nitration method was applied in the first step but optimizations were necessary in order to get the product in required isomer ratio. In the second step, Raney Nickel was found to be the ideal catalyst for the reduction of nitro groups. Finally conversion of amine groups to isocyanate groups was achieved by triphosgene reagent. Structural characterizations were carried out via NMR and FT-IR. Keywords; Toluene diisocyanate, polyurethane, curing agent, triphosgene v ÖZ TOLUEN DİİZOSİYANAT MADDESİNİN SENTEZİ VE KARAKTERİZASYONU Hisar Telli, Ayşegül Yüksek Lisans, Kimya Bölümü Tez Yöneticisi: Prof. Dr. Özdemir Doğan Kasım 2014, 52 sayfa Katı roket yakıtlarının önemli bileşenlerinden biri olan toluen diizosiyanat (TDI) malzemesi hidroksi sonlu polibütadien (HTPB) polimeri ile tepkimeye girerek poliüretan ağ yapısını oluşturur ve yakıt formülasyonu içerisinde olgunlaşma ajanı olarak görev yapar. Bilim Sanayi ve Teknoloji Bakanlığı destekli SANTEZ projesi kapsamında ROKETSAN ile ortaklaşa yürütülen bu araştırma projesinde TDI malzemesinin laboratuvar koşullarında istenilen izomer oranında, yüksek verim ve saflıkta sentezlenmesi için uygun yöntem/yöntemlerin bulunması amaçlanmıştır. TDI maddesi endüstri için çok önemli olmasına rağmen yapılan birçok çalışma patentlidir. Türkiye’de henüz TDI maddesinin üretimi ve bu alanda yapılmış olan bir çalışma yoktur. TDI maddesinin sentezi üç basamaktan oluşmaktadır. Bunlar; toluenin nitrolanması, dinitrotoluenin indirgenmesi ve toluendiaminin fosgenlemesidir. Birinci basamak için standart nitrolama tepkimesi uygulanmıştır ancak istenilen izomer oranını tutturabilmek için tepkime koşullarının optimize edilmesi gerekmiştir. İkinci basamakta nitro gruplarının indirgenmesini içeren Raney Nikel’in ideal katalizör olduğu bulunmuştur. Son olarak amin gruplarının izosiyanat gruplarına dönüştürülmesi trifosgen reaktifi ile gerçekleştirilmiştir. Ürünlerin karekterizasyonu NMR ve FT-IR ile yapılmıştır. Anahtar kelimeler: Toluen diizosiyanat, poliüretan, olgunlaşma ajanı, trifosgen vi To my beloved family and my husband… vii ACKNOWLEDGEMENTS I would like to express my greatest appreciations to my supervisor Prof. Dr. Özdemir Doğan for his patience, guidance, advice, criticism, encouragements throughout this study. I would like to thank DOGAN Research group, especially my labmates Seylan Ayan, Tuğba Kaya Deniz, Ali Tecimer and Duygu Tan for their friendship. I would like to thank Ministry of Science, Industry and Technology of Turkey and ROKETSAN for their financial support during the project. I would like to express my appreciation to Dr. Emre Yusuf Yazıcıoğlu for his encouragement, support, help and interesting scientific discussions. Moreover, I want to thank to chemists at ROKETSAN, especially Özlem Akın Gün, Bora Bilgiç, Ayşe Hande Şarman, Asuman Günbaş and Esra Bayraktar for their help and friendship. I also would like to express my thanks to the ROKETSAN technicians Feridun Yağcıoğlu, Hacı Mehmet Yaman, Necati Güzel, Murat Yiğit and Ali İhsan Keser for their technical assistance. I would like to thank to all organic group members for their friendship. In addition, I would like to thank Nurdan Sargın, Esra Kanberoğlu and Dilşad Susam for their support and friendships. Very special thanks to my friends Zehra Ongun and Selin Şencanlı for their precious friendship. Finally, I owe great thanks to my family for their endless love, support, patience and absolute belief in me. I am grateful to my husband Ali Yasin Telli for his endless love, understanding and moral support. The completion of this study would not have been possible without them. viii TABLE OF CONTENTS ABSTRACT ................................................................................................................. v ÖZ ............................................................................................................................... vi ACKNOWLEDGEMENTS ...................................................................................... viii TABLE OF CONTENTS ............................................................................................ ix LIST OF TABLES ...................................................................................................... xi LIST OF FIGURES ................................................................................................... xii LIST OF SCHEMES ................................................................................................. xiii LIST OF ABBREVIATIONS ................................................................................... xiv INTRODUCTION ....................................................................................................... 1 1.1. Synthesis of Toluene Diisocyanate ............................................................... 4 1.1.1. Current Processes ................................................................................... 4 1.1.2. Alternative Synthetic Pathways for Toluene Diisocyanate (TDI) ....... 10 1.2. Properties of TDI ......................................................................................... 12 1.3. Toxicity of TDI ........................................................................................... 13 1.4. Chemistry of TDI ........................................................................................ 13 1.5. Rocket Propellant ........................................................................................ 14 1.6. The aim of this work ................................................................................... 19 RESULTS AND DISCUSSION ................................................................................ 21 2.1. Nitration of Toluene to Dinitrotoluene ........................................................ 22 2.2. Reduction of Dinitrotoluene to Toluenediamine ......................................... 26 2.3. Conversion of Amino Groups to Isocyanates .............................................. 30 2.4. Determination of Hydrolyzable Chlorine in TDI ........................................ 37 2.5. Studies Related for Other Specifications ................................................. 38 ix CONCLUSION .......................................................................................................... 39 EXPERIMENTAL ..................................................................................................... 41 4.1. Instrumentation ................................................................................................ 41 4.2. Synthesis and Characterization of Compounds ............................................... 42 4.2.1. Synthesis of Dinitrotoluene ...................................................................... 42 4.2.2. Synthesis of Toluendiamine by Continuous Reactor (H-Cube) ............... 43 4.2.3. Synthesis of Toluenediamine by Batch Reactor .....................................
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