HYDROCARBON INDUSTRIAL. Pni. Handbook of. ^m r11?* f 1 ^» La 1 J ELSEVIER. JAMES G. SPEIGHT PhD, DSc AMSTERDAM BOSTON NEW YORK

Transcription

1 Handbook of INDUSTRIAL HYDROCARBON Pni ^m r11?* f 1 ^» La 1 J JAMES G. SPEIGHT PhD, DSc ELSEVIER AMSTERDAM BOSTON NEW YORK HEIDELBERG LONDON OXFORD PARIS SAN DIEGO SAN FRANCISCO SINGAPORE SYDNEY TOKYO Gulf Professional Publishing is an imprint of Elsevier If

2 Preface xiii 1. Chemistry and Chemical Technology 1 1. Introduction 2 2. Organic chemistry The chemical bond Bonding in carbon-based systems 4 3. Chemical engineering Conservation of mass Conservation of energy Conservation of momentum 9 4. Chemical technology Historical aspects Technology and human culture Hydrocarbons Bonding in hydrocarbons Nomenclature of hydrocarbons Isomers Non-hydrocarbons Alcohols Ethers Aldehydes Ketones Organic acids Esters Amines Alkyl halides Amides Properties of hydrocarbons Density Heat of combustion (energy content) Volatility, flammability, and explosive properties Behavior Liquefied natural gas Environmental properties 39 References 41 v

3 Reservoirs vi Contents 2. Sources of Hydrocarbons Introduction Natural products - and deposits Petroleum Natural gas Natural gas hydrates Tar sand bitumen Coal Oil shale Wax Biomass 77 References Hydrocarbons from Petroleum Introduction Gaseous products Naphtha Composition Manufacture Properties and uses Gasoline Composition Manufacture Properties and uses Octane numbers Kerosene and related fuels Composition Manufacture Properties and uses Diesel fuel Gas oil and fuel oil Lubricating oil Composition Manufacture Properties and uses Wax Composition Manufacture Properties and uses 124 References 125

4 Contents vii 4. Production of Hydrocarbons from Natural Gas Introduction Gas processing Water removal Fractionation Acid gas removal Natural gas hydrates Deposits Composition Properties Development Environmental issues Hydrocarbon products Methane Ethane and higher homologs Natural gas liquids Gas condensate Synthesis gas 159 References Hydrocarbons from Coal Introduction Occurrence and reserves Formation and types Coal formation Coal types Mining and preparation Surface mining Underground mining Mine safety and environmental effects Coal preparation Properties Hydrocarbons from coal Gaseous hydrocarbons Gasifiers Gaseous products Gasification processes Underground gasification 191

5 viii Contents 7. Liquid hydrocarbons 7.1. Physicochemical aspects 7.2. Liquefaction processes 8. Solid hydrocarbons References Hydrocarbons from Oil Shale Introduction History 3. Origin 4. Kerogen Occurrence Hydrocarbon fuels Mining and retorting In situ technologies Refining shale oil Environmental aspects The future 236 References Hydrocarbons from Biomass Introduction Wood History Wood chemistry Hydrocarbons from wood Plants Isoprenoid hydrocarbons Waxes Essential oils Terpenes Steroids Biomass conversion 275 References Hydrocarbons from Synthesis Gas Introduction Coal gasification Chemistry 285

6 Contents ix 2.2. Processes Gasifiers Gasification of petroleum fractions Feedstocks Chemistry Commercial processes Gasification of other feedstocks Fischer-Tropsch process Chemistry Catalysts Reactors Process parameters Refining Fischer-Tropsch products 320 References Chemical and Physical Properties of Hydrocarbons Introduction Stereochemistry Molecular weight Chemical properties Physical properties Boiling points and melting points Density and specific gravity Vapor density Flash point and ignition temperature Dew point 350 References Combustion of Hydrocarbons Introduction Combustion chemistry Slow combustion Rapid combustion Complete and incomplete combustion Spontaneous combustion Process parameters Air-fuel ratio Equivalence ratio 374

7 X Contents 8. Combustion of hydrocarbon fuels Combustion of gaseous hydrocarbon fuels Combustion of liquid hydrocarbon fuels Combustion of non-hydrocarbon fuels Formation of particulate matter Char and coke Soot 391 References Thermal Decomposition of Hydrocarbons Introduction Thermal decomposition Hydrocarbons Steam cracking Thermal reforming Catalytic decomposition Fluid catalytic cracking Hydrocracking Catalytic reforming Dehydrogenation Dehydrocyclization 422 References Petrochemicals Introduction Chemicals from paraffins Halogenation Nitration Oxidation Alkylation Thermolysis Chemicals from olefins Hydroxylation Halogenation Polymerization Oxidation Miscellaneous Chemicals from aromatic hydrocarbons Chemicals from acetylene Chemicals from natural gas 460

8 Contents xi 7. Chemicals from synthesis gas 463 References Pharmaceuticals Introduction History Hydrocarbon pharmaceuticals Mineral oil Paraffin oil Steroids Carotenoids and vitamins Misuse and toxicity of hydrocarbons Lower-molecular-weight hydrocarbons Polynuclear aromatic hydrocarbons 492 References Monomers, Polymers, and Plastics Introduction Polymerization Polymers Chain length Structure Copolymers Repeat unit placement Chemical properties Polymer degradation Phase separation Glass transition temperature Molecular weight Plastics Classification Chemical structure Properties Thermoplastics Hydrocarbon fibers 535 References Environmental Effects of Hydrocarbons Introduction Release into the environment 542

9 xii Contents 2.1. Dispersion Dissolution Emulsification Evaporation Leaching Sedimentation or adsorption Spreading Wind Analysis of hydrocarbons in the environment Environmental samples Biological samples Semi- and non-volatile hydrocarbons Assessment of the methods Toxicity hazards Lower boiling hydrocarbons Higher boiling hydrocarbons Remediation of hydrocarbon spills 572 References 575 Glossary 577 Index 631