(Industrial chemistry library 6) giora agam (eds ) industrial chemicals their characteristics and development academic press, elsevier (1994)

Industrial Chemistry Library
Advisory Editor: S.T. Sie, Faculty of Chemical Technology and Materials
Delft University of Technology, Delft, The Netherlands

Science

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Progress in C 1 C h e m i s t r y in J a p a n
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C a l c i u m M a g n e s i u m Acetate. A n E m e r g i n g B u l k C h e m i c a l for
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Industrial C h e m i c a l s . T h e i r Characteristics and D e v e l o p m e n t
(by G. A g a m )


Industrial Chemistry Library, Volume 6

Industrial Chemicals
Their Characteristics and Development

by
Giora A g a m

Dead Sea Bromine Co., Ltd.
and
Ben-Gurion University of the Negev, Beer-Sheva,

Israel

ELSEVIER
Amsterdam — Lausanne — New York — Oxford — Shannon — Tokyo

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1994


ELSEVIER S C I E N C E B.V.

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ν

To my dear parents, YOEL and MANIA, for their confident,
support.

everlasting

To my beloved wife, GALILA, and children, NURIT, Ό AFI, NIVand
who are the real world.

IRIS,

I am grateful to Levina Zurdeker, Eve Boaz, and Pnina Einav, who
enthusiastically helped in bringing this manuscript to print.

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xiii

Preface
C h e m i c a l s in t h e Real World

Members of the ACS Academic-Industry Committee realized in the
early 1970s that the following request was being made from within the
ranks of the chemical industry:
"Send us chemists. Not synthetic organic chemists, spectroscopists,
theoretical physical chemists, but chemists."

Most industrial chemists will adopt and identify with the idea behind
this quotation. However, to the academic ear it will sound at best
unclear, and at worst an arrogant statement — an attitude expressing
a gap between the two worlds: academic vs. industrial chemical re­
search.
In our opinion this gap stems from the following differences:
• A difference in "language" and in concepts.

• The different aims of the research.
It is accepted that the industrial and the academic world speak in
different "languages". It is amazing to discover that university gradu­
ates (more in chemistry than in chemical engineering) are often unfami­
liar with subjects so basic to chemical industry, such as specifications,
formulations, scaling-up and construction materials. Many have never
even heard of such concepts as Flash Point or Assay [1]!
Formulations make up the core and majority of chemical products
known to us in our daily lives. This subject is usually "taught" in the
first high school chemistry course, when the teacher says: "There are
mixtures and there are pure compounds". And this is the beginning and
the end of the study of formulations...
The first exposure of a chemistry graduate to our world of indus­
trial chemicals is described by Beichl and Kreiner as a "cultural shock"
[2]. Clausen and Mattson [3] define the situation as a "widening g u l f
between industry and the academy.
It can be argued that the universities need not teach these subjects
as they can be acquired in the "real world" — in actual industrial
activity. However, the fact that many university graduates are not even
aware of the existence of an industrial language, makes such an acqui­
sition expensive and lengthy. Even an introductory acquaintance with

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xiv

the subject can, as Szmant [4] claims, "shorten the induction period"
required for a chemistry graduate to productively adapt to industry.
After all, 60-70% of employed chemists work in industry — half of them

in industrial R&D [5].
This is extremely important in the rapidly changing world we live
in. How much did we hear of the following concepts just ten years ago
— concepts that changed our world: Perestroyka, 1992, AIDS, TQM,
Green?
To better clarify our point, we formulated a sort of a short "quiz"
and presented it to many university chemists. To avoid embarrassment,
we shall not report the results... And here are the questions:
1.
2.
3.
4.
5.

How does motor oil 20W50 change its viscosity?
What is cyanide doing in table salt? And salt in dynamite?
Why do emulsions have to be broken?
How is the color of olive oil measured?
Would you store concentrated sulfuric acid in an iron con­
tainer?
6. What is scaling-up? And scaling-down?
7. What is "assay"?
8. How do you interpret the sign on the back of the truck
transporting chemicals?
9. Why was the invention of a pencil with eraser granted a
patent, but perpetuum mobile was not?
10. What is the meaning of filter-cake? Slurry? Filter-aid?
11. Why is amphetamine written with a small "a", and Benze­
drine, a name for the same material, written with a capital
"B"?

Let us try to analyze the modus cogitandi and the modus operandi of
two synthetic chemists — in industry and in the university, both having
a research plan for developing a synthetic route to some molecule.
What is the challenge set before the university chemist?
It is imperative that the synthesis will have an innovative element (an
innovative process or a new product). Having succeeded, the researcher
has to provide evidence that the product has been obtained. This is done
by verifying its structure, mainly by physical spectroscopic methods
(MS, IR, UV, NMR, etc.), and often by converting it to other chemical
entities the structure of which is easier to prove. Frequently the evi­
dence is given even without isolating the product.
A good yield is desirable, but not absolutely necessary. And after
the product is isolated, all the other chemicals get thrown down the drain.

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XV

The essence of the above research lies in innovation, supported by
sound evidence. The cost of the experiment is not a factor (as long as
there is a research budget).
We believe that the challenges facing the industrial chemist who
is going to develop a synthesis for a product are more difficult [ 6 ] — if
only because the number of hurdles en route is greater, and slipping
over one of them is enough to disqualify an entire process: in industry
we have to develop a good synthesis. Yield is of the utmost importance.
But we are good chemists, and let's assume that we have succeeded in
obtaining a satisfactory yield.
If the synthesis is good, but the isolation

of the product ("work-up") is complex
we still do not have a process.
If the isolation is easy, but the process
"runs away" when it is scaled up
we still do not have a process.
If the process is successfully scaled up
but the raw materials are unavailable
commercially
we still do not have a process.
If we find the raw materials in the
market, but the product does not meet
quality specifications
we still do not have a process.
If the quality meets market requirements,
but the process requires expensive
equipment which is not available to us
we still do not have a process.
If we possess the necessary equipment,
but we have no solution for treatment
of the wastes
we still do not have a process.
If there is a solution for the waste
treatment, but we cannot protect ourselves
against the materials' toxicity
we still do not have a process.
If we can control the toxicity, but
the process is already patented
we still do not have a process.

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xvi

If the process is not patented, but
all this already costs us too much
money, the process is not economical,
and the shareholders get nervous
we still do not have a process.
Richarz [7] summarizes the gap between the academic and industrial
approaches as follows:
Academic approach :
Complex Models — Simple Systems.
Small Scale.
Industrial approach:
Simple Models — Complex Systems.
Large Scale.
Scale-up still the key issue.
In every research and development effort of a chemical process many
"peripheral aspects" exist which can critically influence the outcome,
even if the "chemistry" looks good. Raw materials, specifications, stand­
ards, construction materials, safety and toxicology, ecology, patents,
equipment, scale-up problems — all of these can reduce the process'
attractiveness. Unfortunately, many of those employed in research and
development (chemists and engineers alike) tend to work within the
narrow limits of their own disciplines, leaving problems caused by
"peripheral considerations" to others "down the stream." Those are
required to "fix up" the process — a situation which could have been
prevented had the R&D personnel considered all these parameters
during the development of the process, from its very beginning.

Regarding the last point, there is often a deficiency in "coordination
of expectations" between the chemists and the engineers involved in
industrial R&D, with responsibilities not clearly defined, especially in
terms of "peripheral considerations". For instance, an ecological problem
can be solved by an engineer, but may be avoided altogether by the R&D
chemist.
The aim of this book is to better acquaint the reader with the basic
concepts of chemistry and chemicals in "the real world", and with all of
those "peripheral" aspects so important for process development and
understanding the world of industrial chemicals.
We shall deal with subjects that are neither "exactly chemistry",
nor "exactly chemical engineering", but which encompass both these
disciplines in a broad circumference. Thus we have not included in our
book subjects covered by those defined disciplines such as chemistry,
chemical engineering or economics, but have concentrated on topics
outside of these, or on the borderlines between them.

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xvii
We hope that this book will contribute to the awareness of the need
for a "comprehensive approach" during the research and development
of industrial chemical products, and will encourage researchers to
assume responsibility for all the peripheral parameters throughout the
entire R&D process.

REFERENCES
[1]
[2]

[3]
[4]
[5]
[6]
[7]

K.E. Kolb, "Teaching Industrial Chymists", Chemtech, 1983, 397.
G.J. Beichl and W.A. Kriner, "Why Not Prepare Chemistry Majors to Work in
Industry?" J. Chem. Ed., 63, 699 (1986).
C A . Clausen III and G. Mattson, "Principles of Industrial Chemistry", J.
Wiley, 1978, p. vii.
H.H. Szmant, "An Industrial Chemistry Course to Bridge the Academia-Industry Gap", J. Chem. E d , 62, 736 (1985).
"Chemistry in t h e Economy", ACS Study, Washington, 1973.
G. Nonhebel, "Chemical Engineering in Practice", Wykeham Publ. (London),
1973, Chap. 11.
W. Richarz, "Chemical Reaction Engineering — Quo Vadis?", Chimia, 42, 424
(1988).

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1

Chapter 1

Naming Chemicals
Father calls me William,
Sister calls me Will
Mother calls me Willie,
But the fellers call me Bill!

Eugene Field

MULTIPLICITY OF NAMES
Had Valium been a child, he could have sung a similar song about
himself...
Why have we chosen to begin our book with such a "dry" subject as
nomenclature and naming chemicals? Well, simply because w e have to
call them by some names. How can we sell them and how can we buy
them if they are nameless?
The following example is a certain widely used material: in indus­
try — for textile dyeing, fertilizing plants with essential micro-nutri­
ents, and for metal cleaning; in medicine — as an anticoagulant and an
antidote against metal poisoning; in the laboratory — as a chelating
agent for volumetric analysis.
Knowing the formula of the material
HOOC-CH.

^C^-COONa
, NCH2 CH2 Ν .
NaOOC-CH^
^ CHj-COOH

we refer to Chemical Abstracts to look for its name. There we shall find
scientific information abstracts regarding this product, under the
name:
• A^iV'-l^-EthanediylbisfN-Ccarboxymethyl) glycine] disodium salt.
If, indeed, we want to buy this material, w e would now turn to
common commercial product lists, catalogs, and company publications,

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2

Chapter 1

and look for it under the above name. The result would be frustrating:
we would not be able to find it. Either the product does not exist
commercially or it has another name.
We would have a much better chance under the common name
(which we probably remember from school days):
• Ethylenediamine Tetra Acetic acid, disodium salt
or an even more common and well-known name amongst the chemists:
• EDTA disodium salt.
The very same material is used in medicine, and the pharmacists have
another name for it. Indeed, it can be found in the pharmaceutical
99
under the name:
standards compendium "The British Pharmacopoeia
• Disodium Edetate.
And on top of it all, manufacturers of textiles, metal cleaners, and other
users will often not know which material is being referred to unless we
use trade names such as:
• Versene (Dow's tradename) or Trilon Β (BASF's tradename).
This is how the users know the material. This is how it is sold and
purchased.
As a central factor in worldwide chemical literature, Chemical
Abstracts plays a major role in determining the chemical name of a
product. The Chemical Abstracts Service (CAS) generally determines
the names in accordance with the principles advocated by IUPAC

(International Union of Pure & Applied Chemistry) and IUB (Interna­
tional Union of Biochemistry).
At the same time, besides the Chemical Abstracts Index Names
there is an additional system determined by IUPAC and WHO (World
Health Organization). In this system non-systematic (trivial) names
are used.
The particular nomenclature rules as prescribed by Chemical
Abstracts or IUPAC will not be discussed here. Those who are inter­
ested are referred to books dealing with this subject [1].
We shall discuss, however, the parallel systems for names and
synonyms which are used in everyday life — in commerce, industry,
agriculture, medicine, etc. In some cases the situation resembles that
of our friend Bill: the material will have a formal systematic name as
well as other names which are more user-friendly.
Moreover, in "real life" there are even instances in which the
systematic nomenclature of Chemical Abstracts will not be applicable,
and we are forced to use other names for chemicals.

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Naming

Chemicals

3

R.D. Bagnall, preaching for the easy-to-use trivial name tells the
story [2] of the chemist who used to prepare for his own experi­
ments bottles of diethyl ether dried by sodium wire. The ether

kept disappearing by a mysterious hand. At last the problem
was solved when the chemist marked his bottle as 3-oxapentane. Simply, no one knew what it was...
We thus use common names, or tradenames — any name that can be
used easily and fluently for daily communication — even at the expense
of being non-systematic. Naturally, IUPAC or CAS names cannot be
used when the product is a natural mixture or formulation (see Chapter
3), i.e. a handmade mixture of chemical compounds. Kerosene, milk,
wax-emulsion and paint are just a few examples. But even when a simple
molecule is discussed, it may frequently be impractical to use the
systematic names. It is clear that doctors and patients will be reluctant
to do so. But as Entschel remarks, it is the case also in less critical
situations [3]. Discussing the dyes industry, he gives the example of a
reactive brown (Figure 1.1), and describes its name as a "verbal tape­
worm", obviously difficult to understand.

CC3ALTATEC7-),

[ 5 - [ [ 4 - C H L O R O - 6 - [(5-

I

[(5-CHLORO-2,6-DIFLUORO- ]-

PYRIMIDINYL)AMIN0]-2-SULF0-PHENYL]AMINQ]-l,3/5-TRIAZIN-2-YL]
AMINO]-4-HYDROXY-3-

[(2-HYDROXY-5-SULFOPHENYL)AZO]-2,7-

NAPHTHALENEDISULF0NAT0(6-)] [ 3 - [ [ L I

[4-[[4-CHLORO~6-[[5-

[(5-CHLORO-2,6-DIFLUORO- 4-PYRIMIDINYL)AMINQ]-2-SULFOPHENYL]
A M I N O J - L 3 , 5 - T R I A Z I N - 2 - Y L ] AMINO] P H E N Y L ] - 4 , 5 - D I H Y D R O - 3 - M E T H Y L 5-OXO-1H-PYRAZOL-4-YL)AZO]-^-HYDROXYBENZENESULFONATO(4-3 - .
HEPTASODIUM

F i g u r e 1.1 CAS name of a reactive brown [3].

Not only do more professionals like the buyer and seller have to
use the name, but also the people at the accounting or transportation
offices, etc. Mistakes and confusion are very probable and this might be
a serious problem from the safety point of view (see Chapter 11), when
the physician, first-aid man or fireman must refer to the specific com­
pound. An example was given of a highway accident near Basel, Swit­
zerland in 1985, where the press reported rather simple chemical
names so garbled that not even chemists could understand them. No
wonder that official safety organizations are concerned about this issue.
In the field of dyes and pigments, the Ecological and Toxicological
Association of the Dyestuff Manufacturing Association proposed that
Color Index generic names should be used, rather than systematic
IUPAC or CAS nomenclature.

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4

Chapter 1

TRADENAMES

Many chemicals are sold under a tradename. This tradename becomes
the trademark, legally registered and protected.
As in other areas of commerce, there are cases where the trade­
name given by a major producer is so common, that it becomes the name
by which the product is known publicly, even though other manufactur­
ers also provide the very same product. Take the example of Teflon,
DuPont's tradename for polytetrafluoroethylene.
Various useful mixtures (specialties), plastic materials, pigments,
insecticides, drugs — all bear tradenames.
But even basic materials are often called by tradenames (e.g.
"Tronacarb" is the tradename Kerr-McGee Corp. gave to sodium bicar­
bonate).
Aspirin is Bayer's tradename for 2-(acetyloxy) benzoic acid. Valium
is Hoffman-La Roche's tradename for diazepam (the generic name —
common name), while according to Chemical Abstracts nomenclature, this
material is called: 7-chloro-l,3-dihydro-l-methyl-5-phenyl-2H-l,4-benzodiazepin-2-one.
"Round-Up" is the name given by Monsanto to its product, a
well-known herbicide, while according to Chemical Abstracts the mate­
rial is called iV-(phosphonomethyl)glycine. By another common name
(generic, and therefore permissible for all uses), it is called glyphosate.
In the case of Nylon, the consumer public was so greatly influ­
enced, that many polymers (even polyethylene) are often mistakenly
called nylon, even if they are not polyamides.
J.L. Meikle and S.M. Spivak [4] tell the story of the invention of
the name Nylon by DuPont which, according to them, was chosen
in 1937 out of some 400 possibilities! They deny the rumor that the
name is derived from the initials of "New York and London"
(mistakenly thought to be where the material was invented).
Other rumors referred to the challenges which crudely called
upon the silk industry to show its ability to compete. The real

story begins with "Nuron" (with the same letters, in the oppo­
site direction to "no run"), but because of its similarity to other
tradenames, it was changed into "Nulon", which was also found
to be similar to other names and was therefore changed to
"Nilon", and finally changed again to Nylon.
This name is considered so enormously successful, and is
thought to have contributed so greatly to the popularity of the
product, that the manufacturer proudly stated: "DuPont cre­
ated a household word".

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Naming

Chemicals

5

The story of Nylon clarifies what brings companies to invent trade­
names in addition to the existing systematic, trivial and common names
by which the chemicals are known. Not surprisingly, the consideration
is purely commercial, wherein the manufacturer wants the consumer
to identify the product with its producer as a means of promoting sales.
In addition to the advertising value, there is another aspect:
assume that we succeeded in selling our product under its tradename
to a non-professional market. For example, a biocide sold to a metal
cutting workshop to prevent bacterial decomposition of the cutting fluid
which is used to lubricate the processed parts. Once we have "pene­
trated" the market it becomes very difficult for our competitor to enter

and push us out. In many instances, the workshop owner does not know
chemistry and is not interested in knowing the chemical identification
of the material. He knows that the material does what it is meant to do
and that's it. If the material had been called by its chemical name, every
competitor who came along would have been able to sell the material
because it would have been clear that he was selling exactly the same
chemical. However, it is very difficult to persuade the same workshop
owner that this is an identical material, and he is often not interested
in listening.
Formulations which are composed of mixtures of chemicals (see
Chapter 3) are naturally given tradenames both because it is impossi­
ble to call a mixture by a chemical name, and because the mixture is
unique to a particular producer and changes from manufacturer to
manufacturer. The tradename allows the manufacturer to conceal the
real composition, thus protecting commercial secrecy. This applies to
household chemicals (such as shoe polish, washing powder, sunscreen
lotion, etc.), but it is also true of industrial products.
It is clear then that formulations having complex and complicated
compositions will be given tradenames. However, when referring to
basic chemicals which are easily described in chemical terms, surely it
is unnecessary to call them by tradenames as well? In other words,
while a producer's formula for washing detergent remains exclusive
(and even protected by patent), the solvent 1,1,1-trichloroethane that one
sells is very similar to the solvent which is sold by others. What is the
reason and rationale — if any — behind calling it by a "private" name?
(Dow, for instance, sells this solvent under the name of Chlorothene.) The
truth is that tradenames are frequently given to simple materials, par­
ticularly those sold to non-chemical industries, and especially to small
ones. In this way the consumer is told by the producer, "I'm not selling
you just any material off the shelf. I understand your needs and I am

selling you that material which exactly suits those needs. I will also
provide you with service and professional consultation, should any

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Chapter 1

θ

problem arise. All this, provided that you buy my material, and not that
of my competitor." This was probably the reasoning which prompted
Stauffer Chemicals to sell sodium ortho-silicate under the name of
"Dryorth", or BASF to sell EDTA under the name of "Trilon B".
Surface-active materials, for example, are usually sold under trade­
names, and of course one can find the same material being sold by many
manufacturers under different tradenames. And if BASF — which did
not discover EDTA — is allowed to call this material by a tradename, it
is certainly permissible for Bayer to call aspirin "Aspirin", and for
Hoffmann-La Roche to call valium "Valium". Due to their immense
popularity, these tradenames, along with Teflon and Nylon, have re­
placed the chemical names.
Major fields in which new materials are commonly given trade­
names are pharmaceuticals, insecticides, polymers and pigments.

WHAT IS THE FORMULA BEHIND THE TRADENAME?
Coming across a tradename, we might be interested in identifying the
material chemically: perhaps we shall want to go to other suppliers for
the same product, or perhaps we shall want to better understand what
we are dealing with.

How can w e do this?
It should be realized that the growing sensitivity towards safety
and ecological issues is greatly pressurizing the manufacturers: pre­
viously they maintained confidentiality regarding the identity of their
products, whereas nowadays they are required to publicize most of the
relevant information. Therefore, if we ask the manufacturer for the
technical data sheet of the product marketed under his tradename, we
stand a good chance of discovering the product's chemical identity.
Thus, in Ciba Geigy's technical brochure (issued in 1986) [5],
referring to a light stabilizer which bears the tradename Chimassorb
944 LD, the exact chemical structure can be found:
Ν

η

Η
Η
tert. octyl
Poly-ito-tllJ^-tetramethylbutyll-imino]-!^^triazine-2/4-diyl][2-(2,2/6,6-tetramethylpiperidyl)imino]-hexamethylene-[4-(2,2,6,o-tetramethylpiperidyl)-imino]}

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Naming

Chemicals

7

Another means of identifying a tradename is to use directories —

commercial compendiums which compile names and addresses of
chemical suppliers (see Chapter 13).
Generally, the directories refer to chemical names which are not
tradenames, but some of them do provide sections dedicated to trade­
names. As an example, in the 1993 edition of Chemical Week Buyers'
Guide [6], some 8,000 tradenames can be found, mostly for the Ameri­
can market. A list of about 2,600 tradenames, aimed at the European
market, can be found in the European Chemical Buyers' Guide 198112
[7]. The well-known reference book, The Merck Index also contains
many tradenames [8].
However, since numerous materials are sold under tradenames,
these sources do not always provide the desired information.
There are a few compendiums which define and identify trade­
names of chemicals. Several will be mentioned herewith:
• "SOCMA Handbook — Commercial Organic Chemical Names" [9].
• J. Pearce (ed.), "Gardner's Chemical Synonyms and Trade Names"
[10].
• H.D. Junge (ed.), "Parat Index of Polymer Trade Names" includes
24,000 names of raw materials and products of the polymer indus­
try [11].
• APhA Drug Names — is the compendium of the American Phar­
maceutical Association, which details over 1,500 drugs by their
tradenames (mostly for the American market). For instance, under
"Acetaminophen", 85 tradenames appear (with an additional 154
entries for other products containing acetaminophen) [12].
• "The Agrochemicals
Handbook" lists tradenames in the agrochemical field [13].
In addition, Chemical Abstracts refers to tradenames, providing they
appear in scientific publications. In such cases the materials can be
found in the Index Guide.

NAMES AND ALTERNATIVE NAMES OF PHARMACEUTICALS
It is commonly known that drugs are not named for "everyday" use
according to the nomenclature of Chemical Abstracts. Pharmacists,
doctors, patients, lawyers and others — all are in need of user-friendly
names of drugs.
A pharmaceutical may have several names during its life cycle. In
the developmental stages of a drug, a code designation is given to the
molecule by the developing company. This designation is composed of

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8

Chapter 1

letters (the initials of the chemist, code of the group of researchers, or
the code of the company, etc.), followed by a serial number. Take, for
example, EXP-126, the code given by DuPont to Rimantadine, a drug
developed by the company.
CB3

The letters EXP code DuPont's experimental drugs. Burroughs-Wellcome used the code letters BW, and the FMC Corp. uses FMC. A list of
codes representing materials of many companies, can be found in the
Merck Index [14]. The next stage of naming is when the drug is first
submitted for approval. The developer must then give it a name. Occa­
sionally, there is a tendency to give a name that will "hint" at the drug's
use, as can be seen in examples such as Anesthesin or Alkagel. While
the American authorities forbid this practice, considering it to be unfair
competition, it is still common practice in Europe. Nowadays, the

naming of a product is not left in the hands of the chemist. It requires
multiple expertise and creativity, involving marketing experts, public
relations professionals, psychologists, and others.
Generally, the name given is proprietary — tradename, brand
name. This commercial name is a trademark which provides legal
protection. However, the American manufacturer is also required to
submit an additional alternative name to the Council of the American
Medical Association. Once approved, this name is published in the
Association's publication, "New and Non-Official Remedies" (NNR),
allowing all drug manufacturers or suppliers to use it. This is the
generic name. It is required that the generic name appears on the
package of the pharmaceutical preparation alongside the tradename.
l-Phenyl-2-aminopropane

CHz CHCH3
NHj

was approved as a stimulant for the central nervous system, under the
tradename Benzedrine. Its generic name, according to the NNR (which
appeared at a later stage), is amphetamine. This name is used by other
manufacturers who do not have the right to use the tradename Benze­
drine.

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Naming

Chemicals

9

It is usually possible to distinguish between a tradename and a
generic name, since the first letter in a tradename is capitalized. But
exceptions are not uncommon, and we occasionally find aspirin instead of
Aspirin.
The vast number of tradenames may cause confusion and difficulty.
The drug sulfanilamide, for example, has no less than 60 tradenames!
Physicians tend to use tradenames in their prescriptions rather
than generic names. In such a case, only the specified brand
may be used.
A tragic consequence of such confusion occurred in the
case of thalidomide — that unfortunate drug which caused so
many birth deformities.
Newspapers have reported that Contergen (a German trade­
name for thalidomide) is hazardous. But Swedish doctors used
thalidomide under the Swedish tradename, Neurosedyn, and
did not identify the danger.
In 1961, a combined effort towards conformity amongst the various
bodies was undertaken by three American organizations:
(1)
(2)
(3)

The American Medical Association.
The U . S . Pharmacopeial Convention (publishers of the
United States Pharmacopeia — USP).
The American Pharmaceutical Association (publishers of the
National Formulary — NF).

In 1967, the U S Food and Drug Administration (FDA) joined the above
as a coordinator [15].
These efforts resulted in the establishment of a council responsible
for determining generic names. In 1978, the council's official directory
of names was published: "The United States Adopted Names" (USAN).
The directory includes 12,000 entries and is updated regularly [16]. A
parallel international directory, International Nonproprietary
Names
(INN), is published as a recommendation by the World Health Organi­
zation (WHO).
THE COLOR INDEX
A unique compendium of products from a completely different field is
listed in the five volumes of The Color Index. It is jointly published by
The Society of Dyers and Colourists (UK) and the American Association
of Textile Chemists and Colorists. In 1971, the third (latest) edition was
published [17].

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Chapter 1

This index details all the coloring materials (dyes, pigments) that
are manufactured. The latest edition comprises 38,000 coloring materi­
als which are based on some 8,000 chemical structures; this includes
approximately 600 pigments with the rest being dyes [18]. The materi­
als are classified by their use, their chemical characteristics, and in
each group by color. This index also records the chemical structure (if

known), methods of application, color characteristics (e.g. resistance to
fading), tradenames, etc.
The reason for discussing The Color Index here is that it uses a
special system of "naming" or identifying dyes and pigments.
Every coloring material is assigned two identity numbers: the first
refers to the method of dyeing, while the second is the identity number
of the specific molecule.
The five-digit identity number is assigned to the coloring material
regardless of its use. Thus if the material can be applied in several
ways, it is represented by only one five-digit number, but with several
names which represent its multi-faceted use.
Let's consider the example of the pigment whose trivial name is
Copper Phthalocyanine and whose formula is:

According to Chemical Abstracts,

the material will be called:

[29H,31H-phthalocyanato(2-)-N29,N30,N31,N32] copper.
Its two "names" in the Color Index are:
• C.I. Pigment Blue (indicating its method of application).
• C.I. 74160 (indicating its identity number).
Despite this, we are certain that many consumers of this pigment (in
textile, plastics, ink, paint industries) do not know that they use Phtha­
locyanine Blue, just as Jourdain was unaware that he spoke in prose all
his life: "Par ma foil il y a plus de quarante ans que je dis de la prose
sans que j'en süsse rien" [Moliere, Le Bourgeois Gentilhomme (1970), II,
iv]. These consumers usually know this material by its various trade-

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Naming

Chemicals

11

names — Cyanine Lutetia, Vynamon Blue, Blue Irgalite, Monastral
Fast Blue, to cite but a few.
FOOD, DRUG AND COSMETIC (FD&C) COLORS
The public commotion and debate in 1976 regarding the banning of the
food color "Red Number 2" is well remembered. The food industry then
considered itself lucky as it was still possible to replace this hazardous
product with other food colors ("Red Number 3" or "Red Number 4").
These "names" are used for coloring materials but are clearly not
Color Index nomenclature. Indeed, separate systems exist for those
colorants to which we are highly exposed — in food, drugs and cosmet­
ics. This list is the outcome of a 1938 American regulation, the Federal
Food, Drug and Cosmetic Act, wherein the relevant colorants are divided
into three categories:
(1)
(2)
(3)

FD&C Colorants — materials which are permitted for use in
food, drugs and cosmetic preparations.
D&C Colorants — permitted for drugs and cosmetics, exclud­
ing food.
External D&C Colorants — only for external use in drugs and

cosmetics.

The materials classified as FD&C and D&C colors are given identity
numbers [19, 20].
And if after all this we take a look at erythrosine, for example, we
shall discover that it is a "multinamed creature":

Common name: Erythrosine.
2 ,4 ,5 ,7 - tetraiodofluorescein disodium salt.
Trivial name:
3',6'- Dihydroxy-2 ,4 ,5 ,7-tetraiodo-spiro [isobenzoCA name:
furan-l(3H),9M9H]xanthen]-3-one disodium salt.
Erythrosine B; Erythrosine BS.
Trade names:
Red No. 3.
FD&C:
Food Red 14; Acid Red 51; C.I. 45430.
C.I.:
[568-63-8].
CAS Reg. No.:
/

/

,

/

/

,

/

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Chapter 1

12

REFERENCES
[ 1] R.S. Cahn and O.C. Dermer, "Introduction to Chemical Nomenclature", 5th
ed., Butterworth, 1979.
[ 2] R.D. Bagnall, "What's in a Name?", Chem. Brit., Jan. 1992, p. 46.
[ 3] R. Entschel, "The Importance of Confidentiality for the Colorant Industry",
Chimia, 40, 269 (1986).
[ 4] J.L. Meikle and S.M. Spivak, "What's in a Name?", Chemtech, 1990, 204.
[ 5] "Chimassorb 944 LD", Ciba Geigy Publ. No. 28 264/edf, 1986.
[ 6] "1993 Chemical Week Buyer's Guide", Chemical Week Assoc., 1992.
[ 7] "European Chemical Buyers' Guide 198172", IPC Industrial Press, 1982.
[ 8] S. Budavary (Ed.), "The Merck Index", 11th e d , Merck & Co, 1989.
[ 9] "SOCMA Handbook — Commercial Organic Chemical Names", American
Chemical Society, 1966.
[10] J. Pearce (Ed.), "Gardner's Chemical Synonyms and Trade Names", 9th e d ,
Gower Technical Press, 1987.
[11] H.-D. Junge (Ed.), "Parat Index of Polymer Trade Names", VCH Publ, 1987.
[12] L.L. Corrigan and J.D. Shoff (Eds), "APhA Drug Names", American Pharma­
ceutical Association, 1979.
[13] D. Hartley and H. Kidds (Eds.), "The Agrochemicals Handbook," 2nd e d . The

Royal Chemical Society, 1987.
[14] Reference 8, p. misc. 5.
[15] The United States Pharmacopeia XXI, U.S. Pharmacopeial Convention, 1974.
[16] "USAN and the USP Dictionary of Drug Names", U.S Pharmacopeial Conven­
tion, 1978.
[17] "Color Index", 3rd e d . Society of Dyers and Colourists, 1971.
[18] F.W. Billmeyer, J r , and M. Saltzman, "Principles of Color Technology", 2nd
e d , J. Wiley, 1981.
[19] S. Zuckerman and J. Senackerib, "Colorants for Foods, Drugs and Cosmetics"
in "Kirk-Othmer Encyclopedia of Chemical Technology", 3rd e d . Vol. 6, J.
Wiley, 1979, p. 561.
[20] D.L. Pavia, G.M. Lampman and G.S. Kriz, "Introduction to Organic Labora­
tory Techniques", Saunders College Publ, 1988, p. 269.

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13

Chapter 2

Classifications of Chemicals
Order is a lovely thing;
On disarray it lays its wing,
Teaching simplicity to sing.
"The Monk in the Kitchen"
Anna Hempstead Branch

CLASSIFICATION OF CHEMICALS — WHAT FOR?
In 1990, the Chemical Abstracts Service registered the 10 millionth

compound in its registry system. (It was cis-(+)-4,6,7,8,8a,8b-hexahydro-6,6,8b-trimethyl-3H-naphtho[l,8-bc]furan). About one percent of
these, a hundred thousand chemicals, are on the marketplace [1]. These
chemicals have approximately 350,000 common names. How are they
listed? How are they categorized? Such a population needs order. We
shall try and make some.
The obvious way of listing chemicals, a way accepted by researchers,
is alphabetically by the name of the chemical, without any classification.
But what name? And how does one deal with those materials
having very complex names? Then again, should Chemical
Abstracts'
names be used? Or generic names? Or common names? And how is it
possible to classify materials that are not pure, like washing powder?
And materials that are better known by their tradenames (e.g. Teflon)?
Such an alphabetical list will not include all possible materials,
and is necessarily limited.
Grouping chemicals in the "real world" is difficult: the boundaries
are unclear, there is much room for overlapping and duplication, and
different parameters are needed for classification. The question is, of
course, what purpose does the classification serve? Different types of
chemicals mean different types of businesses. The differences cross the
lines of all activities dealing with chemicals: technological, marketing,
management and financial characteristics vary widely from one group of
chemicals to another.

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Chapter 2

These differences may be very great. Due to such "incompatibil­
ity", the Union Carbide Corp. was split in 1992, and the industrial gases
business has been spun off the other chemical businesses. We would
also like to consider the point of view of the user who looks for a
chemical, when this user may be positioned anywhere along the line
starting with research and ending with application.
Accordingly, we shall discuss the major types of classifications
beginning with the chemically-based mode and ending with the com­
mercially-based mode: (i) organic/inorganic chemical listing, (ii) classi­
fication by price and (iii) classification by application.
If we examine a specific chemical within each of the three lists, we
find that different types of information are hidden behind the name
(Table 2.1). We shall discuss all these modes of classification in detail.
T A B L E 2.1 I N F O R M A T I O N IMPLIED BY T H E V A R I O U S C L A S S I F I C A T I O N
METHODS FOR CHEMICALS

Information

Chemical identity and
structure
Price
Volume in market
Practical use
Nature of production
equipment

Type of Classification
Organic/inorganic
listing

Listing by
price

Listing by
Application

+++

+

+

-

+++
++
++

+++
+

LISTING BY CHEMICAL NATURE — ORGANIC/INORGANIC CHEMICALS
From the chemical point of view this is, of course, an entirely clear
definition. Nevertheless, for daily use we often find it necessary to
deviate from this framework. Polymers, for instance, are frequently
presented as a separate group, as are industrial gases. Products which
are mixtures (i.e. toothpaste, paint, etc.) cannot be included in such a
classification as they contain both organic and inorganic materials.
The inorganic group of materials found in commercial catalogs

may, on the one hand, include low priced mineral products such as
potash, and expensive chemicals for electronic use in semiconductors
such as gallium arsenide on the other. Similarly, in the organic group

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Classifications

of Chemicals

15

one can find the inexpensive ethylene alongside the highly priced
atenolol (a beta-blocker drug).
This method of classifying is used by the customs authorities for
listing chemicals. In the customs classification, until recently known as
the Bruxelles Tariff Number system (BTN) and lately as the Harmo­
nized System (HS), Section 28 is dedicated to inorganic chemicals,
whereas Section 29 deals with organic materials. The groups are deter­
mined by the product's chemical nature. For example, the group 29.21
deals with the "compounds possessing amino group". Subgroup 1000 of
this group (i.e. 29.21.1000) represents acyclic monoamines, their salts and
their derivatives. This group includes in particular methylamine, di­
methyl and trimethylamine, and diethylamine. All the other acyclic
amines are not specified here, but are grouped together under Section
"29.21-1990/6 —Others".
When the molecule contains two different functional groups, the
decision regarding the correct customs section for that material be­
comes more complicated. p-Chloroaniline can, for example, be placed in

Section "29.03.6900 — Halogen derivatives of aromatic hydrocarbons —
Others" or in Section "29.21.4290 — Compounds having amino functional
group — Aromatic monoamines and their derivatives — Aniline and its
Salts — Others."
It is worth noting that organic and inorganic chemicals are in­
cluded in two chapters. However, the customs' classification for chemi­
cal materials includes 14 additional chapters (!) — mostly dedicated to
formulations (functional mixtures of materials). Among the other chap­
ters we find:
•
•
•
•
•
•
•
•
•

Pharmaceutical products.
Fertilizers.
Tannin and its derivatives; coloring materials; ink.
Oil extracts; cosmetics.
Soap; organic surfactants; lubricants.
Albumins; starches; adhesives; enzymes.
Explosives; pyrotechnical products; matches.
Photographic or cinematographic goods.
Miscellaneous chemical products.

CLASSIFICATION BY PRICE

Classification of chemicals by price is an effective method. It involves a
certain paradox, however. We classify chemical products and then
claim that chemical classification is awkward, and that economic clas­
sification based on price, might be more useful...

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Chapter 2

16

The justification for this is twofold: firstly, the purpose of the
sorting and classifying is to allow the manufacturers and the consumers
to deal with those materials which they need — clearly an economical
aspect. Secondly, it will be shown that prices of chemicals also indicate
chemical and technological characteristics in addition to the marketing
and economic aspects.
Here too (as was the former case) it is easier to suggest the basis
for definition, then to carry out the actual listing. We find that terms
which are commonly used to define subgroups are vague, overlapping
and confusing. Terms such as the following:
•
•
•
•
•
•
•
•

commodities
bulk chemicals
specialty chemicals
chemical specialties
intermediates
fine chemicals
branded chemicals
composition chemicals

are used as sub-definitions in an attempt to avoid duplication and confu­
sion.
Generally, it will be found that bulk chemicals (or commodities)
are referred to on one end of the scale, fine chemicals on the other end,
and all the rest — in between.
In many instances this classification tends to correlate with the
degree of the chemical "complexity" of the product which increases from
bulk materials to fine chemicals: high complexity is expressed by the
increasing number of production stages, as well as by the greater
number of atoms in the molecule (except for polymers, of course).
We chose somewhat arbitrarily the following sub-division:
(1)
(2)
(3)

Bulk chemicals or commodities — characterized by large
quantities and relatively low prices (up to $l/kg).
Intermediates/specialties — average quantities, with a price
range from $1 to $50/kg.
Fine chemicals — small quantities ranging in price from $50

to $l,000/kg.

Before attempting to develop this approach, the question of stabil­
ity or instability of the prices in the chemical marketplace must be
addressed. The common market forces play their usual role. The en­
trance of new producers, from developing countries for example, pushes
prices down. Such is also the case when governmental subsidization of
production enables the reduction of prices. As a result, old, inefficient,

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