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 CHEMISTRY
and the CHEMICAL
INDUSTRY
A Practical Guide
for Non-Chemists
Robert A. Smiley, Ph.D.
Harold L. Jackson, Ph.D.

CRC PR E S S
Boca Raton London New York Washington, D.C.

© 2002 by CRC Press LLC

 TX544_Frame_FM.fm Page ii Tuesday, December 4, 2001 2:43 PM

Library of Congress Cataloging-in-Publication Data

Smiley, Robert A.
Chemistry and the chemical industry : a practical guide for non-chemists / Robert A.
Smiley, Harold L. Jackson.
p. cm.
Includes bibliographical references and index.
ISBN 1-58716-054-4 (alk. paper)
1. Chemistry, Technical. I. Jackson, Harold L. (Harold Leonard), 1923- II. Title.

TP145 .S65 2002

660—dc21 2001052817
CIP

This book contains information obtained from authentic and highly regarded sources. Reprinted material
is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable
efforts have been made to publish reliable data and information, but the authors and the publisher cannot
assume responsibility for the validity of all materials or for the consequences of their use.

Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic
or mechanical, including photocopying, microfilming, and recording, or by any information storage or
retrieval system, without prior permission in writing from the publisher.

The consent of CRC Press LLC does not extend to copying for general distribution, for promotion, for
creating new works, or for resale. Specific permission must be obtained in writing from CRC Press LLC
for such copying.

Direct all inquiries to CRC Press LLC, 2000 N.W. Corporate Blvd., Boca Raton, Florida 33431.

Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are
used only for identification and explanation, without intent to infringe.

Visit the CRC Press Web site at www.crcpress.com

© 2002 by CRC Press LLC

No claim to original U.S. Government works

International Standard Book Number 1-58716-054-4
Library of Congress Card Number 2001052817
Printed in the United States of America 1 2 3 4 5 6 7 8 9 0
Printed on acid-free paper

© 2002 by CRC Press LLC

 TX544_Frame_FM.fm Page iii Tuesday, December 4, 2001 2:43 PM

Preface
The chemical industry affects virtually all aspects of our lives. Were it to
disappear suddenly, we would find ourselves living again in the early nine-
teenth century without cars, airplanes, television, electric lights, most of our
colorful clothing, most perishable food, most drugs and medicine, plastics,
and all the rest of the modern conveniences that most of us take for granted.
Consider how the chemical industry contributes to your daily life. For
example, when you get up in the morning, you brush your teeth using
toothpaste, which is a mixture of chemicals squeezed from a plastic tube
onto plastic bristles mounted in a plastic handle. You may take a shower
using soap and shampoo, each made by the chemical industry, and finally
dry, brush, or comb your hair with other articles made of plastic. While doing
this, you will likely be looking into a mirror over a porcelain or cultured
marble sink while standing on vinyl plastic floorcovering, tile, or carpeting,
all of which are products of the chemical industry. The varnish coating the
wooden floors of your house and the paint or wallpaper covering the walls
are products of the chemical industry. At breakfast, it is likely that the kitchen
counters and table are topped with plastic, as are the chairs. The refrigerator
would not work without chemicals either for the refrigeration unit or the
insulation in its walls. The interior is plastic lined and the exterior has a
durable coating made possible by the chemical industry. Your breakfast food
is probably fresh because it was treated with chemical preservatives and/or
shipped in a box with a plastic lining. The car or bus that you go to work
in is totally chemical dependent, from the anti-corrosion treatment of the
metal, the protective paint and the plastic parts and tires to the chemical
battery that starts the vehicle, the oil that lubricates it, and the gasoline that
fuels it. And so it goes.
The fact that our daily lives are so dependent on the chemical industry
does not appear to be widely recognized, even by those working in the
chemical industry. And so, as companies are forced in a world economy to
become more productive and more quality conscious, as well as having a
greater concern for the environment, it becomes essential that their present
and future employees understand the basic concepts upon which the chemical
industry (indeed, our modern existence) is based. This book is designed to
aid in that understanding by reviewing the important aspects of industrial
chemistry in a way that can be understood even by those who have not taken
any formal chemistry courses.

© 2002 by CRC Press LLC

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No mathematics is used and basic physical science is minimized. Why

chemicals behave as they do is not explained. It is assumed that the end
result of the manufacturing processes presented is the information wanted
by the reader and not the science or engineering involved. If needed, the
latter information can be obtained from listed sources.
The first chapter begins with a description of the chemical industry and
its unique features and branches. The most common terms used in chemistry
are defined, using nonscientific analogies where possible. In the following
chapters, some basic organic chemistry is presented so that later descriptive
explanations of the largest and most important products of the chemical
industry can be better understood. The product descriptions include the raw
material sources, manufacturing processes, and, of most importance, their
commercial uses. Finally, there is a short compilation of general information
sources.
The style of the book is to present only a small amount of information
on each page with a slide-like illustration using short descriptions and easily
understood chemical equations and structures. Under each illustration is
additional information or comments with room for the reader to make notes
if desired. Although there is obvious continuity, an attempt has been made
to make each page subject somewhat independent so that readers can study
the contents of the book one page at a time at their own pace. Of necessity,
because of this format, there is considerable repetition. We do not consider
this bad.

Robert A. Smiley
Harold L. Jackson

© 2002 by CRC Press LLC

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Authors
Robert A. Smiley, Ph.D. retired from the DuPont Company in 1990, after which
he became an independent consultant in general industrial chemistry. Clients have
included ICI, Westinghouse, Clorox, Arco, and many smaller chemical companies.
Currently he consults for Dixie Chemical Company where he holds the title of
corporate research fellow. He is also the president of Falcon Lab LLC, a company
engaged in patent licensing. His fields of expertise include nitrile chemistry, diiso-
cyanate and polyurethane chemistry, nitric acid oxidation, and nitration chemistry
and explosives. For many years he gave sponsored seminars on industrial chemistry
and polyurethane chemistry both in Europe and the U.S. He received a B.S. degree
in industrial chemistry from Case Institute of Technology and a Ph.D. in organic
chemistry from Purdue University and joined DuPont as a research chemist in 1954.
After a number of successful assignments in the process development of polymer
intermediates, he became a research supervisor and then moved on to other positions
in technology licensing, business analysis and back to research as research associate
and research fellow. He holds 26 U.S. patents and is the author or co-author of 13
publications.

Harold L. Jackson, Ph.D. has 51 years of experience in the chemical industry. After
receiving a Ph.D. in organic chemistry from the University of Illinois in 1949, he
joined DuPont’s central research department where he made significant contributions
in the areas of inorganic, organic, and polymer chemistry. He later moved to other
research responsibilities in DuPont’s chemicals and petrochemicals departments
where he studied polymer synthesis and characterization, polymer intermediate
development, and solvent chemistry. He has been involved in and assisted with
marketing efforts on commercial products resulting from his research work. He
retired in 1992 as a research fellow. Dr. Jackson holds 32 U.S. patents and is the
author of numerous technical articles. In addition to his industrial activities, Dr.
Jackson served as visiting professor of organic chemistry at the University of Kansas.

© 2002 by CRC Press LLC

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Contents
Preface ......................................................................................................................iii

Chapter 1. Introduction ..........................................................................................1

Chemical and Allied Products Industries..................................................................2
Chemical Industry......................................................................................................3
Characteristics ..................................................................................................3
The Beginnings ................................................................................................4
Research and Development/Engineering Technology .....................................5
History ..............................................................................................................6
Language of Chemistry .............................................................................................7
Chemistry...................................................................................................................8
Properties and Changes....................................................................................8
Substance States...............................................................................................9
Chemical Substances......................................................................................10
Chemical Representation ...............................................................................11
Symbols of Common Elements .....................................................................12
Divisions.........................................................................................................13
General Definitions ........................................................................................14

Chapter 2. Important Inorganic Chemicals .......................................................15

1999 U.S. Annual Production..................................................................................16
Sulfuric Acid (H2SO4) .............................................................................................17
Nitrogen (N2) ...........................................................................................................19
Inorganic Nitrogen Compounds ..............................................................................20
Oxygen (O2).............................................................................................................21
Lime (CaO)..............................................................................................................23
Ammonia (NH3).......................................................................................................24
Phosphoric Acid (H3PO4) ........................................................................................25
Chlorine (Cl2)...........................................................................................................26
Sodium Hydroxide (NaOH) ....................................................................................28
Sodium Carbonate (Na2CO3)...................................................................................30
Nitric Acid (HNO3)..................................................................................................32
Hydrogen (H2) .........................................................................................................34

Chapter 3. Organic Chemistry.............................................................................35

Organic Chemistry...................................................................................................36
Organic Compounds ................................................................................................37
Carbon Structure......................................................................................................38

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Carbon Chains .........................................................................................................39

Carbon–Carbon Multiple Bonds .............................................................................40
Aliphatic Hydrocarbons...........................................................................................41
Paraffins..........................................................................................................41
Structure .........................................................................................................42
Structure: Long Hydrocarbon Chains............................................................43
Isomers.....................................................................................................................44
Paraffin Names.........................................................................................................46
Paraffins ...................................................................................................................48
Functional Groups ...................................................................................................49
Formulae ..................................................................................................................50
Paraffins: Chemical Properties ................................................................................51
Types of Carbon Atoms .................................................................................51
Chlorination....................................................................................................52
Nitration .........................................................................................................53
Oxidation ........................................................................................................53
Pyrolysis or “Cracking” .................................................................................53
Isomerization ..................................................................................................53
Unsaturated Hydrocarbons ......................................................................................54
Olefins ............................................................................................................55
Olefins: Chemical Properties...................................................................................56
Unsaturated Hydrocarbons ......................................................................................57
Acetylenes ......................................................................................................57
Oxygenated Organic Compounds............................................................................58
Oxidation..................................................................................................................59
Alcohols ...................................................................................................................60
Polyalcohols.............................................................................................................61
Manufacture of Alcohols .........................................................................................62
Aldehydes ................................................................................................................63
Ketones ....................................................................................................................64
Acids ........................................................................................................................65
Esters........................................................................................................................67
Ethers .......................................................................................................................69
Nitrogen-Based Organic Compounds......................................................................70
Amines .....................................................................................................................71
Amides .....................................................................................................................72

Chapter 4. Aromatic Organic Chemistry ...........................................................73

Aromatic Organic Chemistry ..................................................................................74
Benzene ..........................................................................................................74
Substituted Benzenes .....................................................................................76
Polyaromatic Compounds ..............................................................................84
Carboxylic Acids............................................................................................85
Phenols ...........................................................................................................87
Amines ...........................................................................................................89

© 2002 by CRC Press LLC

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Benzene-Based Intermediates for Epoxy Resins and Polycarbonates..........90

Benzene-Based Intermediates to Polyurethanes............................................91

Chapter 5. Polymer Chemistry ............................................................................93

Polymers ..................................................................................................................94
Natural Polymers .....................................................................................................95
Polymer Structure ....................................................................................................96
Polymer Crystallinity...............................................................................................98
Polymer Classes.......................................................................................................99
Polymer Synthesis .................................................................................................100
Step Growth Polymerization .................................................................................101
Examples ......................................................................................................102
Chain Growth (Addition) Polymerization.............................................................105
Typical Chain Growth Polymers ...........................................................................108
Copolymers ............................................................................................................109
Polyethylene...........................................................................................................110
Polypropylene ........................................................................................................111
Poly(vinyl chloride) ...............................................................................................112
Polystyrene.............................................................................................................113
Engineering Resins ................................................................................................114
Fibers......................................................................................................................115

Chapter 6. High-Volume Organic Chemicals ...................................................117

High-Volume Organic Chemicals..........................................................................118
Raw Material Sources ..................................................................................118
1999 U.S. Annual Production ......................................................................119
Ethylene (CH2=CH2)..............................................................................................120
Ethylene Derivatives ..............................................................................................121
Ethanol .........................................................................................................122
Ethylene Oxide.............................................................................................123
Vinyl Chloride..............................................................................................124
Ethylbenezene and Styrene..........................................................................125
Propylene (CH3CH=CH2) .....................................................................................126
Propylene Derivatives ............................................................................................127
Acrylonitrile .................................................................................................128
Propylene Oxide...........................................................................................129
Isopropylbenzene..........................................................................................130
Epichlorohydrin............................................................................................132
Butadiene (CH2=CH-CH=CH2).............................................................................134
Butadiene Derivatives ............................................................................................135
Hexamethylenediamine ................................................................................136
Cyclooctadiene and Cyclododecatriene.......................................................137
Benzene (C6H6)......................................................................................................138
Benzene Derivatives ..............................................................................................140
Cyclohexane .................................................................................................141

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Nitrobenzene and Aniline ............................................................................143

Maleic Anhydride.........................................................................................144
Xylenes (C6H4(CH3)2)............................................................................................145
Xylene Derivatives.................................................................................................146
Phthalic Anhydride (from o-Xylene)...........................................................146
Terephthalic Acid and Dimethyl Terephthalate ...........................................147

Chapter 7. Environmental Protection and Waste Disposal ............................149

Environmental Protection ......................................................................................150
Types of Possible Environmental Pollution by the Chemical Industry................151
To the Air .....................................................................................................151
To Water .......................................................................................................151
Methods of Pollution Control................................................................................152
Pollution Control Laws and Regulations ..............................................................153
Partial History of Pollution and Pollution Control by the Chemical Industry ....154

Information Sources ............................................................................................157

© 2002 by CRC Press LLC

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Introduction
1
The objective of this chapter is to provide a basis for some understanding
of chemistry and the chemical industry. Segments and characteristics of the
industry together with important events in chemical history are briefly pre-
sented. The “language” of chemistry is introduced and important chemical
terms are defined.

© 2002 by CRC Press LLC

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2 Chemistry and the Chemical Industry

CHEMICAL AND ALLIED PRODUCTS

INDUSTRIES

IMPORTANT SEGMENTS
Inorganic chemicals
Petrochemicals
Synthetic resins and plastics
Textile fibers
Synthetic rubber
Pharmaceuticals and drugs
Soap, detergents, and cosmetics
Paint, varnishes, and printing inks
Fertilizers and other agricultural chemicals
Adhesives and sealants
Dyes and pigments
Paper
Glass

In terms of total product value, the worldwide shipments of the chemical

and allied products industries were almost 1600 billion dollars in 1999. In
the U.S. alone, the value was 435 billion dollars (source: Chemical & Engi-
neering News, June 26, 2000). The U.S. has the largest chemical economy
by far of any country in the world, followed by Japan and Germany as distant
second and third.

© 2002 by CRC Press LLC

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Introduction 3

CHEMICAL INDUSTRY

CHARACTERISTICS
Large, diverse, and complex
Global
Strong technology base
Many segments, highly fragmented
Subject to business cycles
Highly competitive
Capital intensive
Committed to research and development
Advanced in use of computers and computer controls
Over 50% of the products are based on petroleum
Best employee safety record among all major industries
Criticized for many environmental problems

Because of the absolute necessity for chemicals in almost every manufac-

turing industry, it is difficult to define exactly what the chemical industry is.
A good definition, however, is that the chemical industry consists of all
companies engaged in converting raw materials obtained from the environ-
ment (air, ore, petroleum, trees, crops, etc.) into chemical intermediates plus
the companies that convert these intermediates into consumer end products.
Chemicals derived from petroleum or natural gas, known as petrochemicals,
comprise about 55% of the total chemicals produced. Some of the global-
ization of the chemical industry now taking place is due to the shifting of
production by petrochemical producers to energy-rich regions of the world
such as Indonesia, Mexico, and the Middle East.

© 2002 by CRC Press LLC

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4 Chemistry and the Chemical Industry

CHEMICAL INDUSTRY

THE BEGINNINGS
Pre-1600 Alchemists sought to turn base metals (iron, zinc, lead) into
gold using the four “elements”— earth, fire, air, and water.
About 1600 The idea of the four “elements” was challenged and the
chemical era began.
1600s Robert Boyle worked out scientific experimental methods and
published his findings (the scientific method).
1700s Joseph Priestly discovered oxygen.
Antoine Lavoisier distinguished between chemical and
physical changes and enumerated and verified the
fundamental law of the conservation of mass.
1800s Dmitri Mendeleev published the Periodic Table of the
Elements.

Ancient man (prehistoric–600 BC) practiced certain chemical arts such as

extraction and working of metals, manufacture of leather, production of
alcoholic beverages, and the use of vegetable oils, alkaloids, and narcotics.
The Greek philosophers (600–200 BC) speculated on problems in the realm
of what we now call chemistry, but they did little or no experimentation. In
the Dark and Middle Ages, alchemy flourished and gradually evolved into
an experimental science as the result of the thinking of men such as Roger
Bacon (1214–1294), Paracelsus (1493–1541), and Francis Bacon
(1561–1626). The birth of modern chemistry as an exact science, based on
the law of the conservation of mass and on the quantitative study of chemical
reactions, is dated from the work of Lavoisier.

© 2002 by CRC Press LLC

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Introduction 5

CHEMICAL INDUSTRY

RESEARCH AND DEVELOPMENT/ENGINEERING TECHNOLOGY

Important base for chemical industry:
R&D spending for 2000 was over $250 billion.
Most of the R&D in the U.S. is funded and carried out by the chemical
industry.
High investment facilities required with modern (state-of-the-art)
scientific equipment.
R&D activities:
Basic chemical research (by trained chemists); much of this is done
in universities
Improve existing products (e.g., better quality)
Improve existing processes (by chemists and engineers), including
cost reductions
By-product disposal and utilization
Solution of environmental problems

The size of today’s chemical industry is a result of research and development

(R&D) activities that generated new products and processes resulting in rapid
industry growth. Over the years, R&D emphasis shifted from basic research
aimed at new chemicals and their uses to improvement of existing products
and processes. Today, substantial R&D is directed toward solving problems
related to the environment and to satisfying governmental regulations.

© 2002 by CRC Press LLC

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6 Chemistry and the Chemical Industry

CHEMICAL INDUSTRY

HISTORY
Pre-1900 Cement, lye, soap, explosives, dyes, paint, fertilizer, chemicals
based on coal
1920s–30s Cellophane and rayon (based on wood), medicinals,
photographic chemicals, nylon, plastics
1940s Synthetic rubber, pesticides, plastic films, chemicals based on
petroleum
1950s Engineering plastics, preservatives, new catalysts
1960s Foreign investment, lower prices, performance improvements,
pollution awareness
1970s Energy and feedstock problems, higher raw materials costs
1980s Imports, environment, and health concerns
1990s Global industry, governmental regulations

Industrial chemistry is barely 100 years old, but tremendous developments

were made during that time because of advances in basic chemical and engi-
neering science. These advances resulted from research efforts conducted
within chemical industry laboratories as well as in university laboratories.
During the 1950s, the nature of the industry changed from emphasis on
development of totally new products to refinement of existing types of
products. In recent years, product refinements have been guided by concerns
about human health and protection of the environment.

© 2002 by CRC Press LLC

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Introduction 7

LANGUAGE OF CHEMISTRY

Chemical naming (nomenclature)

Systematic
Chemical Abstracts (American Chemical Society)
Common (historical)
“Nickname” (acronyms and trade names)
Relationship of names to chemical structure
Properties (chemical, physical)
Chemical formulae (chemical shorthand)
Pronunciation

To be knowledgeable in chemistry, one must be familiar with its language.

This language includes the naming of chemicals, both systematic and com-
mon names, and the names and definitions of significant chemical and
physical properties. The relationship of chemical names to chemical struc-
tures and formulae is also important. And, just as with any language, if one
is to talk chemistry, it helps to be able to pronounce the names and other
terms. Many of the terms and names needed to understand chemical “lan-
guage” are introduced and defined throughout this book.
A major part in the language of chemistry is in learning the names of
the chemicals (nomenclature). Many chemicals, particularly the more com-
mon ones, are known by several different names. For example, the chemical
CH3CH2OH has the systematic name “ethanol.” The publication Chemical
Abstracts (American Chemical Society) also uses the name “ethanol.” The
historical or common name is “ethyl alcohol” or “grain alcohol.” A “nick-
name” for it is just “alcohol,” and there are various tradenames, depending
on the manufacturer. For example, the Eastman Company sells it under the
®
name of Tecsol . Even trained chemists have trouble with nomenclature,
which makes the use of and need for written chemical formulae common
among chemists.

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8 Chemistry and the Chemical Industry

CHEMISTRY

PROPERTIES AND CHANGES

Properties Characteristics of a substance
Physical properties Observable characteristics such as density, color,
smell, hardness, solubility, etc.
Chemical properties Properties of a substance that cause specific behavior
during chemical reactions
Chemical reaction Any change that alters the chemical properties of a
substance or forms a new substance
Reactants The substances present at the beginning of a chemical
reaction
Products The substances formed in a chemical reaction

One of the important tasks of chemistry is to study how substances can be

identified or distinguished from each other, that is, a study of properties.
Such studies are also essential in determining how substances can be used
in human endeavors.
There are two types of physical properties: qualitative properties and
quantitative properties. Qualitative properties are those that cannot be mea-
sured, such as smell or taste. Quantitative properties, on the other hand, can
be given precise mathematical values, for example, the weight of a certain
volume of a substance (density), the temperature at which the substance boils
(boiling point), or electrical conductivity.
Chemical properties depend on the ways in which a substance interacts
(reacts) with other substances. Sulfuric acid reacts with iron to form iron sulfate
and hydrogen.

Iron + Sulfuric acid Iron sulfate + Hydrogen

This is a chemical reaction. The fact that iron reacts when it comes into
contact with sulfuric acid is a chemical property of iron. Conversely, the
ability of sulfuric acid to affect iron is a chemical property of sulfuric acid.
The sulfuric acid and iron are called reactants in the above equation, and
the iron sulfate and hydrogen are the products of the reaction.

© 2002 by CRC Press LLC

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Introduction 9

CHEMISTRY

SUBSTANCE STATES
Solid state The state (or phase) in which a substance has a definite
volume and shape
Liquid state The state in which a substance has a definite volume, but
can change shape
Gaseous state A state in which a substance has no definite volume or shape
Melting The change of state from solid to liquid
Vaporization A change of state from liquid to gaseous
Condensation A change of state from gaseous to liquid
Sublimation The change of state from solid to gaseous without going
through the liquid state

A change of state is a physical change that does not alter chemical properties.
It usually takes place by increasing or decreasing the temperature of a
substance. The ability to change the state of substances is important in the
synthesis and purification of chemicals.
Water from a tap is an example of a chemical in the liquid state, whereas
ice is water in a solid state. When liquid water boils, it turns to steam, which
is water in the gaseous state. A dripping icicle on a warm winter day is an
example of melting, whereby the solid phase of water (ice) is converted back
to the liquid state. Droplets of water forming on a cool surface is the result
of condensation of gaseous water (steam) back to liquid water. Carbon dioxide,
the gas in carbonated beverages, is known as dry ice when it is in the solid
state. When dry ice is heated, it goes directly to a gas without first becoming
liquid. This is sublimation.

© 2002 by CRC Press LLC

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