MATAR, S. (2000). Chemistry of Petrochemical Processes.pdf

This book is dedicated to the memory of Professor Lewis Hatch

(1912–1991), a scholar, an educator, and a sincere friend.

Chemistry of

PETROCHEMICAL

PROCESSES

2nd Edition

rights reserved. Printed in the United States of America. This book, or parts

thereof, may not be reproduced in any form without permission of the publisher.

Gulf Publishing Company

Book Division

P.O. Box 2608, Houston, Texas 77252-2608

Library of Congress Cataloging-in-Publication Data

Printed on acid-free paper (

∞

Contents

Preface to Second Edition . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xi

Preface to First Edition . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xiii

CHAPTER ONE

Primary Raw Materials for Petrochemicals . . . . . . . . . . . . . . . . . 1

Introduction 1

Natural Gas 1

Natural Gas Treatment Processes 3, Natural Gas Liquids 8,

Properties of Natural Gas 10

Crude Oils 11

Composition of Crude Oils 12, Properties of Crude Oils 19, Crude

Oil Classification 21

Coal, Oil Shale, Tar Sand, and Gas Hydrates 22

References 26

CHAPTER TWO

Hydrocarbon Intermediates . . . . . . . . . . . . . . . . . . . . . . . . . . . . .29

Introduction 29

Paraffinic Hydrocarbons 29

Methane 30, Ethane 30, Propane 31, Butanes 31

Olefinic Hydrocarbons 32

Ethylene 32, Propylene 33, Butylenes 34

Dienes 36

Butadiene 37, Isoprene 37

Aromatic Hydrocarbons 37

Extraction of Aromatics 38

Liquid Petroleum Fractions and Residues 42

Naphtha 43, Kerosine 45, Gas Oil 46, Residual Fuel Oil 47

References 47

CHAPTER THREE

Crude Oil Processing and Production of Hydrocarbon

Intermediates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49

Introduction 49

Physical Separation Processes 49

Atmospheric Distillation 50, Vacuum Distillation 51, Absorption

Process 52, Adsorption Process 52, Solvent Extraction 53

Conversion Processes 54

Thermal Conversion Processes 55, Catalytic Conversion

Processes 60

Production of Olefins 91

Steam Cracking of Hydrocarbons 91, Production of Diolefins 101

References 107

CHAPTER FOUR

Nonhydrocarbon Intermediates . . . . . . . . . . . . . . . . . . . . . . . . . 111

Introduction 111

Hydrogen 111

Sulfur 114

Uses of Sulfur 116, The Claus Process 116, Sulfuric Acid 117

Carbon Black 118

The Channel Process 119, The Furnace Black Process 119, The

Thermal Process 119, Properties and Uses of Carbon Black 120

Synthesis Gas 121

Uses of Synthesis Gas 123

Naphthenic Acids 130

Uses of Naphthenic Acid and Its Salts 130

Cresylic Acid 131

Uses of Cresylic Acid 133

References 133

CHAPTER FIVE

Chemicals Based on Methane . . . . . . . . . . . . . . . . . . . . . . . . . . 135

Introduction 135

Chemicals Based on Direct Reactions of Methane 136

Carbon Disulfide 136, Hydrogen Cyanide 137, Chloromethanes 138

Chemicals Based on Synthesis Gas 143

Ammonia 144, Methyl Alcohol 149, Oxo Aldehydes and

Alcohols 163, Ethylene Glycol 166

References 167

CHAPTER SIX

Ethane and Higher Paraffins-Based Chemicals . . . . . . . . . . . . . 169

Introduction 169

Ethane Chemicals 169

Propane Chemicals 171

Oxidation of Propane 171, Chlorination of Propane, 172,

Dehydrogenation of Propane 172, Nitration of Propane 173

n-Butane Chemicals 174

Oxidation of n-Butane 175, Aromatics Production 177,

Isomerization of n-Butane 180

Isobutane Chemicals 180

Naphtha-Based Chemicals 181

Chemicals from High Molecular Weight n-Paraffins 182

Oxidation of Paraffins 183, Chlorination of n-Paraffins 184,

Sulfonation of n-Paraffins 185, Fermentation Using n-Paraffins 185

References 186

CHAPTER SEVEN

Chemicals Based on Ethylene . . . . . . . . . . . . . . . . . . . . . . . . . . 188

Introduction 188

Oxidation of Ethylene 189

Derivatives of Ethylene Oxide 192, Acetaldehyde 198, Oxidative

Carbonylation of Ethylene 201

Chlorination of Ethylene 201

Vinyl Chloride 202, Perchloro- and Trichloroethylene 203

Hydration of Ethylene 204

Oligomerization of Ethylene 205

Alpha Olefins Production 206, Linear Alcohols 207, Butene-l 209

Alkylation Using Ethylene 210

References 211

vii

CHAPTER EIGHT

Chemicals Based on Propylene . . . . . . . . . . . . . . . . . . . . . . . . . 213

Introduction 213

Oxidation of Propylene 214

Acrolein 215, Mechanism of Propene Oxidation 215, Acrylic

Acid 217, Ammoxidation of Propylene 218, Propylene Oxide 221

Oxyacylation of Propylene 226

Chlorination of Propylene 226

Hydration of Propylene 227

Properties and Uses of Isopropanol 228

Addition of Organic Acids to Propene 232

Hydroformylation of Propylene: The Oxo Reaction 232

Disproportionation of Propylene (Metathesis) 234

Alkylation Using Propylene 235

References 236

CHAPTER NINE

C 4 Olefins and Diolefins-Based Chemicals . . . . . . . . . . . . . . . . 238

Introduction 238

Chemicals from n-Butenes 238

Oxidation of Butenes 239, Oligomerization of Butenes 248

Chemicals from Isobutylene 249

Oxidation of Isobutylene 250, Epoxidation of Isobutylene 251,

Addition of Alcohols to Isobutylene 252, Hydration of

Isobutylene 253, Carbonylation of Isobutylene 255, Dimerization

of Isobutylene 255

Chemicals from Butadiene 255

Adiponitrile 256, Hexamethylenediamine 257, Adipic Acid 257,

Butanediol 258, Chloroprene 258, Cyclic Oligomers of

Butadiene 259

References 260

CHAPTER TEN

Chemicals Based on Benzene, Toluene, and Xylenes . . . . . . . . . 262

Introduction 262

Reactions and Chemicals of Benzene 262

viii

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