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Industrial Hydrocarbon Processes Handbook of INDUSTRIAL HYDROCARBON PROCESSES JAMES G. SPEIGHT PhD, DSc AMSTERDAM • BOSTON • HEIDELBERG • LONDON NEW YORK • OXFORD • PARIS • SAN DIEGO SAN FRANCISCO • SINGAPORE • SYDNEY • TOKYO Gulf Professional Publishing is an imprint of Elsevier Gulf Professional Publishing is an imprint of Elsevier The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, UK 30 Corporate Drive, Suite 400, Burlington, MA 01803, USA First edition 2011 Copyright Ó 2011 Elsevier Inc. All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher Permissions may be sought directly from Elsevier’s Science & Technology Rights Department in Oxford, UK: phone (+44) (0) 1865 843830; fax (+44) (0) 1865 853333; email: [email protected]. Alternatively you can submit your request online by visiting the Elsevier web site at http://elsevier.com/locate/ permissions, and selecting Obtaining permission to use Elsevier material Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library Library of Congress Cataloging-in-Publication Data A catalog record for this book is availabe from the Library of Congress ISBN–13: 978-0-7506-8632-7 For information on all Elsevier publications visit our web site at books.elsevier.com Printed and bound in the UK 1112131415 10987654321 Gulf Professional Publishing is an imprint of Elsevier The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, UK 30 Corporate Drive, Suite 400, Burlington, MA 01803, USA First edition 2011 Copyright Ó 2011 Elsevier Inc. All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher Permissions may be sought directly from Elsevier’s Science & Technology Rights Department in Oxford, UK: phone (+44) (0) 1865 843830; fax (+44) (0) 1865 853333; email: [email protected]. Alternatively you can submit your request online by visiting the Elsevier web site at http://elsevier.com/locate/ permissions, and selecting Obtaining permission to use Elsevier material Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library Library of Congress Cataloging-in-Publication Data A catalog record for this book is availabe from the Library of Congress ISBN–13: 978-0-7506-8632-7 For information on all Elsevier publications visit our web site at books.elsevier.com Printed and bound in the USA 1112131415 10987654321 PREFACE This book presents an analysis of the process steps that are required to produce hydrocarbons from various raw materials. The book will demon- strate the means by which hydrocarbons are produced from different raw materials and aims at helping the reader develop an instinct for process development strategy. This book emphasizes conversions, which may be defined as chemical reactions applied to industrial processing. The basic chemistry will be set forth along with easy-to-understand descriptions since the nature of the chemical reaction will be emphasized in order to assist in the understanding of reactor type and design. In addition, the book contains chapters on the Physical and Chemical Properties of Hydrocarbons; Combustion of Hydrocarbons; Thermal Decomposition of Hydrocarbons; Petrochemicals; Monomers, Polymers, and Plastics; Pharmaceuticals; and finishes with a chapter on the Environ- mental Effects of Hydrocarbons. This book is arranged in an organized, easy-to-read, and understandable manner and presents the process steps that are required to produce chemicals from various raw materials. It will also assist chemists, engineers, and all manufacturing personnel, even specialists, as it is often possible to translate such general procedures from one discipline to another. For the growing number of chemical engineers and scientists who enter sales, executive, or management positions, a broader acquaintance with the chemical industry in its entirety is essential. For all these, the specialist, the salesperson, and the manager, the information is presented in a connected logical manner with an overall viewpoint of many processes. James G. Speight PhD, DSc Laramie, Wyoming June 2010 xiiij CHAPTER 1 Chemistry and Chemical Technology Contents 1. Introduction 2 2. Organic chemistry 3 2.1. The chemical bond 3 2.2. Bonding in carbon-based systems 4 3. Chemical engineering 7 3.1. Conservation of mass 8 3.2. Conservation of energy 9 3.3. Conservation of momentum 9 4. Chemical technology 9 4.1. Historical aspects 10 4.2. Technology and human culture 11 5. Hydrocarbons 13 5.1. Bonding in hydrocarbons 15 5.2. Nomenclature of hydrocarbons 16 5.2.1. Alkanes 16 5.2.2. Alkenes 18 5.2.3. Alkynes 19 5.2.4. Cycloalkanes 19 5.2.5. Aromatic hydrocarbons 20 5.3. Isomers 24 6. Non-hydrocarbons 25 6.1. Alcohols 26 6.2. Ethers 27 6.3. Aldehydes 27 6.4. Ketones 28 6.5. Organic acids 28 6.6. Esters 28 6.7. Amines 29 6.8. Alkyl halides 30 6.9. Amides 30 7. Properties of hydrocarbons 31 7.1. Density 33 7.2. Heat of combustion (energy content) 34 7.3. Volatility, flammability, and explosive properties 35 7.4. Behavior 37 Handbook of Industrial Hydrocarbon Processes Ó 2011 Elsevier Inc. ISBN 978-0-7506-8632-7, doi:10.1016/B978-0-7506-8632-7.10001-5 All rights reserved. 1j 2 Chemistry and Chemical Technology 7.5. Liquefied natural gas 38 7.6. Environmental properties 39 References 41 1. INTRODUCTION Chemistry (from the Arabic al khymia) is the science of matter and is concerned with the composition, behavior, structure, and properties of matter, as well as the changes matter undergoes during chemical reactions. Chemistry is a physical science and is used for the investigation of atoms, molecules, crystals, and other assemblages of matter, whether in isolation or combination, which incorporates the concepts of energy and entropy in relation to the spontaneity or initiation of chemical reactions or chemical processes. Disciplines within chemistry are traditionally grouped by the type of matter being studied or the kind of study and include (alphabetically): (1) analytical chemistry, which is the analysis of material samples to gain an understanding of their chemical composition and structure; (2) biochem- istry, which is the study of substances found in biological organisms; (3) inorganic chemistry, which is the study of inorganic matter (inorganic chemicals, such as minerals); (4) organic chemistry, which is the study of organic matter (organic chemicals, such as hydrocarbons); and (5) physical chemistry, which is the study of the energy relations of chemical systems at macro, molecular and sub-molecular scales. In fact, the history of human culture can be viewed as the progressive development of chemical technology through evolution of the scientific and engineering disciplines in which chemistry and chemical engineering have played major roles in producing a wide variety of industrial chemicals, especially industrial organic chemicals (Ali et al., 2005). Chemical tech- nology, in the context of the present book, relies on chemical bonds of hydrocarbons. Nature has favored the storage of solar energy in the hydrocarbon bonds of plants and animals, and the evolution of chemical technology has exploited this hydrocarbon energy profitably. The focus of this book is hydrocarbons and the chemistry associated with hydrocarbons in organic chemistry, which will be used to explain the aspects of hydrocarbon properties, structure, and manufacture. The book will provide information relating to the structure and prop- erties of hydrocarbons and their production through process chemistry and chemical technology to their conversion into commercial products. Chemistry and Chemical Technology 3 2. ORGANIC CHEMISTRY Organic chemistry is a discipline within chemistry that involves study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of carbon-based compounds (in this context – hydrocarbons). On the other hand, inorganic chemistry is the branch of chemistry con- cerned with the properties and behavior of inorganic compounds. This field covers all chemical compounds except the myriad of carbon-based compounds, such as the hydrocarbons, which are the subjects of organic chemistry. The distinction between the two disciplines is far from absolute, and there is much overlap, most importantly in the sub-discipline of organ- ometallic chemistry in which organic compounds and metals form
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