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Stephen Morrow

The People’s Game?

Football, Finance and
Society
The People’s Game?
 Stephen Morrow

The People’s Game?

Football, Finance and Society

2nd ed. 2023

Stephen Morrow
Heriot-Watt University
Edinburgh, UK

ISBN 978-3-031-20931-4    ISBN 978-3-031-20932-1 (eBook)

https://doi.org/10.1007/978-3-031-20932-1

© The Editor(s) (if applicable) and The Author(s), under exclusive licence to Springer Nature
Switzerland AG 2023
This work is subject to copyright. All rights are solely and exclusively licensed by the Publisher, whether
the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of
illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and trans-
mission or information storage and retrieval, electronic adaptation, computer software, or by similar or
dissimilar methodology now known or hereafter developed.
The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication
does not imply, even in the absence of a specific statement, that such names are exempt from the relevant
protective laws and regulations and therefore free for general use.
The publisher, the authors, and the editors are safe to assume that the advice and information in this book
are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or
the editors give a warranty, expressed or implied, with respect to the material contained herein or for any
errors or omissions that may have been made. The publisher remains neutral with regard to jurisdictional
claims in published maps and institutional affiliations.

This Palgrave Macmillan imprint is published by the registered company Springer Nature Switzerland AG.
The registered company address is: Gewerbestrasse 11, 6330 Cham, Switzerland
To Mum and Dad
 Foreword

Stephen Morrow has authored a timely and refreshing book on the future
of football in which he poses the critical question, “is football still the
people’s game?” Based on the author’s wide experience and expertise, the
book is a positive response to the intensifying clash of cultures between
community and commerce that now dominate the modern game.
Acknowledging a world of accelerating change, the huge expansion of
financial and investment interest in the game, the growing concerns of
supporters about the loss of cherished ideals and the relentless intrusion
of money as the driving force reshaping the higher reaches of the game,
this book looks for a rapprochement between the competing interests.
This is a tough assignment. But the book seeks to find common ground
and reminds us of the pressing realities facing the game. Recent events
only reinforce the urgency of reconciling conflicting interests and the
challenge that “big money” now presents in modern football. The behav-
iour of FIFA and the decision to host the World Cup in Qatar, the fiasco
of the European Super League, the growing interest in fan ownership, the
concerns of government about the future of the game, the fan-led review
of Tracey Crouch MP suggesting an independent regulator and the ongo-
ing debates about the suitability of certain sponsors provide some chal-
lenging insights as to where the game is heading.

vii
viii Foreword

If football means anything, it is about being rich in sentiment, emo-

tion, nostalgia and brimming full of memories and dreams. Football has
played an important part in my personal story. For me it is about a sense
of place, culture, identity, class, community, solidarity and purpose. But
there are many other inspiring aspects to the game: club achievement,
history, pride, identity, loyalty, passion and often affection that trickles
down the years. These sentiments cannot be measured only in goals, tro-
phies and finance, but also in terms of the emotional bonds that have
carried many clubs from one century to the next and will carry them into
an increasingly uncertain future.
The early history of the game brought out the best in working people
and provided a generation of local heroes as a focus for their pride and
passion which established such incredible loyalties that we still see today
in every part of Britain.
Many clubs now face significantly contrasting times, and the social,
economic and financial landscape has changed out of all recognition.
Some clubs are secure enough to seek success, but others struggle just to
survive.
Much of my life has been wrapped up in the game. A constellation of
factors and events have aligned to shape and mould a football mad, work-
ing-class child who has retained, to this day, a lifelong passion for the
game, perhaps a combined obsession with football and politics, both
rooted in community.
My involvement with the game has been that of millions of typical
Scots through the years. I write first, foremost and always, as a football
fan. I have additional insights as a former professional football player, as
a politician and someone with considerable experience of public life.
Signing for Leeds United as a schoolboy professional under Don Revie
but unable to settle down I returned to Scotland and played professional
football for East Fife, representing Scotland in an international youth
tournament in the former Yugoslavia.
Political life, as an MP and Minister at Westminster, Member and
Minister of the new Scottish Parliament and Government and as First
Minister of Scotland, has allowed me to develop my interest in football
culminating in Scotland bidding to host the European Championships,
as well as Golf ’s Ryder Cup. Sport remains a vital component of a nation’s
 Foreword ix

lifestyle. We can tend to forget that football is integral, along with other
great sports, to a nation’s fitness, health and sense of wellbeing. After leav-
ing elected politics and public office, the Scottish Football Association
asked me to undertake an extensive in-depth review of the governance of
the game in Scotland and its youth football programme, including both
the organisation of the grassroots and elite development. Significant
changes resulted from the reports. In recent years, much of my interest
has been furthered by being a board member of the Scottish Football
Supporters Association.
This book continues and deepens the debate on the future of football.
It respects the enduring legacies of the past, acknowledges the challenges
of the present and crucially recognises the need for factions within the
game to work together if a more balanced and fan-centric future is to be
secured. Short-term priorities and a tendency to ignore the “common
football good,” in its various guises, can be a product of too little finance,
as well as too much finance. The way we run our game determines the
way we generate and attract interest and investment. Who runs the game
and in whose interests is it run remain pertinent. Change can only be
achieved by football authorities and clubs being less secretive and more
open about their aims and ideals. More trust and respect are needed
between community interests and commercial investments. Greater
democracy is needed within the game and the contribution of fans must
not be ignored. The history of the game must be respected. Great foot-
balling traditions are a vital part of why the game matters.
This book embraces the key issues impacting the modern game but
true to his enthusiasm for football to remain, “the people’s game,” Stephen
Morrow has combined tradition, modernity and realism in a way that
provides a more resilient way forward for the “beautiful game”.

Board Member of the Scottish Football  Henry McLeish

Supporters Association, Edinburgh, Scotland
 Acknowledgements

My thanks are due to all those who have assisted me in researching and
writing this book. First, to my friend and colleague, Dr April Henning,
for reminding me during the Super League debacle that I knew quite a lot
about this area and, more importantly, for encouraging me to think about
a second, if somewhat belated, edition.
The book draws on published literature in a number of areas and I am
grateful to all those authors referred to in the text. More specifically I am
particularly indebted to my colleagues Professor Ian Thomson (the
University of Birmingham), Emeritus Professor Andrew Adams (Heriot-­
Watt University), Professor Brian Howieson (the University of Stirling)
and former student, Severin Oeckl, with whom I have collaborated
recently on different projects that have contributed to this book. I am also
grateful to my former colleagues in the Sport Social Science Research
Group at the University of Stirling and to Jamie Corr (Senior Vice
President, Sponsorship and Consultancy at MKTG Sports +
Entertainment) for their helpful discussions and advice. A thank you also
to the late Frank McMahon, a friend and mentor without whom I would
never have become an academic with an interest in the business of football.
I am grateful to Henry McLeish for providing a Foreword to this new
edition and to the late Michael Marra for graciously allowing the words
to his song Hamish to be used as a musical preface to the first edition of

xi
xii Acknowledgements

the book. My sincere thanks also to Esther Rani and Balaji Padmanaban
at Springer Nature for their support throughout the duration of this
project.
Finally, an enormous thank you to my family. To Jill for her love and
patience throughout the writing of this book; to Caitlin for showing no
interest whatsoever in football beyond her one visit to a game in 2001
(see Chap. 1); to Hugh for, in contrast, having a significant interest in
football and an exhaustive knowledge of all player transfers and loans;
and to Beth for reminding me that there is a sporting world and life
beyond football.
Stephen Morrow
The author and publishers are grateful to the following companies and
organizations for the permission to reproduce their material:
Figure 1.6, Gini coefficients for the Big 5 leagues, season 2019/20 and
Exhibit 2.3, Financial Match of the Week are reproduced with the kind
permission of Off the Pitch APS, Aarhus, Denmark. Table 1.2, Enterprise
value (ranges), is reproduced with the kind permission of Football
Benchmark, Ace Advisory Zrt. Hungary. Exhibit 2.4, Swiss ramble finan-
cial analysis, is reproduced with the kind permission of Kieron O’Connor.
Exhibit 2.6, Burnley FC in the Community CSR statistics (6 June 2022),
is reproduced with the kind permission of Burnley FC in the Community,
Burnley. Table 2.2, CSR activities in the Scottish Premiership during
COVID-19, is reproduced from Oeckl, S. and Morrow, S. (2022), ‘CSR
in Professional Football in Times of Crisis - New Ways in a Challenging
New Normal’, International Journal of Financial Studies, vol. 10 under
the MDPI Open Access Agreement. Exhibit 2.7, Sport Positive Leagues,
is reproduced with the kind permission of Sport Positive, London. Table
4.2, Fan typology: German football, is reproduced from Jaeger, J. (2021),
‘Football Fans and Stakeholder Theory: A Qualitative Approach to
Classifying Fans in Germany’, Sport, Business and Management: An inter-
national journal, vol. 11, no. 5, with the kind permission of Emerald
Publishing Limited. Table 4.3, Governance typology of football support-
ers, is adapted from Garcia, B. and Llopis-Goig, R. (2020), ‘Club-
Militants, Institutionalists, Critics, Moderns and Globalists: A
Quantitative Governance-Based Typology of Football Supporters’,
International Review for the Sociology of Sport, vol. 55, no. 8, and
 Acknowledgements xiii

reproduced with the permission of SAGE under the STM Permission

Guidelines.
Every effort has been made to contact all the copyright holders, but if
any have been inadvertently omitted the publishers will be pleased to
make the necessary arrangements at the earliest opportunity.
 Contents

1 F
 ootball’s Ever-Changing Economics  1

2 Reporting
 and Communicating the Performance and Value
of Football 53

3 Organizational Forms: Ownership and Governance123

4 Football Clubs: Who Are the People?163

5 Where Business Meets Society: What Is a Football Club?211

6 C
 onclusion227

N
 otes231

R
 eferences235

I ndex279

xv
 List of Figures

Fig. 1.1 Concentrated success—the EPL 6

Fig. 1.2 Concentrated success—Ligue 1 6
Fig. 1.3 Concentrated success—Bundesliga 1 7
Fig. 1.4 Concentrated success—Serie A 8
Fig. 1.5 Concentrated success—La Liga 9
Fig. 1.6 Gini coefficients for the Big 5 leagues, season 2019/20.
(Source: Off the Pitch, 2021) 10
Fig. 1.7 Distribution of TV revenue: ratio of high to median clubs.
(Source: UEFA, 2020c) 16
Fig. 1.8 UEFA total revenue from club competitions 2019/20 (€bn) 31

xvii
 List of Tables

Table 1.1 Television rights fees 12

Table 1.2 Broadcasting income as a percentage of turnover 13
Table 1.3 Norwich City: the cost of relegation 23
Table 1.4 UEFA Champions’ League revenue allocation, 2019/20 31
Table 1.5 Percentage split of the market pool 32
Table 1.6 UEFA Champions’ League market pool league table, 2019/20 34
Table 2.1 Enterprise value ranges (extract) 70
Table 2.2 CSR activities in the Scottish Premiership during COVID-19 100
Table 3.1 EPL club ownership (as of August 2022) 130
Table 4.1 Football supporter segment characteristics 172
Table 4.2 Fan typology: German football 175
Table 4.3 Governance typology of football supporters 178

xix
 List of Exhibits

Exhibit 1.1 Objectives—UEFA Champions’ League 35

Exhibit 2.1 Strategic Report requirements and examples 58
Exhibit 2.2 Watford FC fixed asset disclosure (extract) 67
Exhibit 2.3 Financial match of the week 79
Exhibit 2.4 Swiss ramble financial analysis 84
Exhibit 2.5 Aims of UEFA FFP regulations 90
Exhibit 2.6 Burnley FC in the community CSR statistics
(6 June 2022) 98
Exhibit 2.7 Sport Positive Leagues 107
Exhibit 3.1 Recommendation 11—Fan-led review 137
Exhibit 4.1 Shadow Board Engagement and Consultation Issues 183

xxi
 Another Random Document on
Scribd Without Any Related Topics
phosgene and chloropicrin, phosgene and superpalite, and
phosgene and diphenylchloroarsine have been found.

Fig. 26.—Interior of a Shell Dump.

The English introduced the use of projectors in the Spring of

1917. They have a decided advantage over shell in that they hold a
larger volume of gas and readily lend themselves to surprise attacks.
As the Germans say, “the projector combines the advantages of gas
clouds and gas shell. The density is equal to that of gas clouds and
the surprise effect of shell fire is also obtained.”
Toward the close of the war, the Germans made use of a mixture
of phosgene and pumice stone. A captured projector contained
about 13 pounds of phosgene and 5½ pounds of pumice. There
seems to be some question as to the value of such a procedure.
Lower initial concentrations are secured; this is due, in part of
course, to the smaller volume of phosgene in the shell containing
pumice. Pumice does seem to keep the booster from scattering the
phosgene so high into the air, and at the same time does not prevent
the phosgene from being liberated in a gaseous condition. This
would indicate that pumice gives a more even and uniform
dispersion and a more economical use of the gas actually used.
Owing to its non-persistent nature (the odor disappears in from
one and a half to two hours) and to its general properties, phosgene
really forms an ideal gas to produce casualties.

Action on Man
Phosgene acts both as a direct poison and as a strong lung
irritant, causing rapid filling of the lungs with liquid. The majority of
deaths are ascribed to the filling up of the lungs and consequently to
the suffocation of the patients through lack of air. This filling up of the
lungs is greatly hastened by exercise. Accordingly, all rules for the
treatment of patients gassed with phosgene require that they
immediately lie down and remain in that position. They are not even
allowed to walk to a dressing station. The necessity of absolute quiet
for gassed patients undoubtedly partly accounts for the later habit of
carrying out a prolonged bombardment after a heavy phosgene gas
attack. The high explosive causes confusion, forcing the men to
move about more or less and practically prevents the evacuation of
the gassed. In the early days of phosgene the death rate was unduly
high because of lack of knowledge of this action of the gas. Due to
the decreased lung area for oxygenizing the air, a fearful burden is
thrown on the heart, and accordingly, those with a heart at all weak
are apt to expire suddenly when exercising after being gassed.
As an illustration of the delayed action of phosgene, a large scale
raid made by one of the American divisions during its training is
highly illuminating.
This division decided to make a raid on enemy trenches which
were situated on the opposite slope of a hill across a small valley. Up
stream from both of the lines of trenches was a French village in the
hands of the Germans. When the attack was launched the wind was
blowing probably six or seven miles per hour directly down stream
from the village, i.e., directly toward the trenches to be attacked. The
usual high explosive box barrage was put around the trenches it was
intended to capture.
Three hundred Americans made the attack. During the attack a
little more than three tons of liquid phosgene was thrown into the
village in 75- and 155-millimeter shells. The nearest edge of the
village shelled with phosgene was less than 700 yards from the
nearest attacking troops. None of the troops noticed the smell of
phosgene, although the fumes from high explosive were so bad that
a few of the men adjusted their respirators. The attack was made
about 3 a.m., the men remaining about 45 minutes in the vicinity of
the German trenches. The men then returned to their billets, some
five or six kilometers back of the line. Soon after arriving there, that
is in the neighborhood of 9 a.m., the men began to drop, and it was
soon discovered that they were suffering from gas poisoning. Out of
the 300 men making the attack 236 were gassed, four or five of
whom died.
The Medical Department was exceedingly prompt and vigorous in
the treatment of these cases, which probably accounted for the very
low mortality.
This is one of the most interesting cases of the delayed action
that may occur in gassing from phosgene. Here the concentration
was slight and there is no doubt its effectiveness was largely due to
the severe exercise taken by the men during and after the gassing.
It should be remarked in closing that while gas officers were not
consulted in the planning of this attack, a general order was shortly
thereafter issued requiring that gas officers be consulted whenever
gas was to be used.
 CHAPTER VII
LACHRYMATORS

Without question the eyes are the most sensitive part of the body
so far as chemical warfare is concerned. Lachrymators are
substances which affect the eyes, causing involuntary weeping.
These substances can produce an intolerable atmosphere in
concentrations one thousand times as dilute as that required for the
most effective lethal agent. The great military value of these gases
has already been mentioned and will be discussed more fully later.
There are a number of compounds which have some value as
lachrymators, though a few are very much better than all the others.
Practically all of them have no lethal properties in the concentrations
in which they are efficient lachrymators, though we must not lose
sight of the fact that many of them have a high lethal value if the
concentration is of the order of the usual poison gas. The
lachrymators are used alone when it is desired to neutralize a given
territory or simply to harrass the enemy. At other times they are used
with lethal gases to force the immediate or to prolong the wearing of
the mask.
A large number of the lachrymators contain bromine. In order to
maintain the gas warfare requirements, it was early decided that the
bromine supply would have to be considerably increased. The most
favorable source of bromine is the subterranean basin found in the
vicinity of Midland, Michigan. Because of the extensive experience of
the Dow Chemical Co. in all matters pertaining to the production of
bromine, they were given charge of the sinking of seventeen
government wells, capable of producing 650,000 pounds of bromine
per year. While the plant was not operated during the War, it was
later operated to complete a contract for 500,000 pounds of bromine
salts. They will be held as a future war asset of the United States.
 The principal lachrymators used during the War were:

Bromoacetone,
Bromomethylethylketone,
Benzyl bromide,
Ethyl iodoacetate,
Bromobenzyl cyanide,
Phenyl carbylamine chloride.

Chloropicrin is something of a lachrymator, but it has greater

value as a toxic gas.

Halogenated Ketones
One of the earliest lachrymators used was bromoacetone.
Because of the difficulty of obtaining pure material, the commercial
product, containing considerable dibromoacetone and probably
higher halogenated bodies, was used. The presence of these higher
bromine derivatives considerably decreased its efficiency as a
lachrymator. The preparation of bromoacetone involved the loss of
considerable bromine in the form of hydrobromic acid. This led the
French to study various methods of preparation, and they finally
obtained a product containing 80 per cent bromoacetone and 20 per
cent chloroacetone, which they called “martonite.” As the war
progressed, acetone became scarce, and the Germans substituted
methylethylketone, for which there was little use in other war
activities. This led to the French “homomartonite.”
Various other halogen derivatives of ketones have been studied
in the laboratory, but none have proven of as great value as
bromoacetone, either from the standpoint of toxicity or lachrymatory
power.
Bromoacetone may be prepared by the action of bromine (liquid
or vapor) upon acetone (with or without a solvent). Aqueous
solutions of acetone, or potassium bromide solutions of bromine,
have also been used.
 Pure bromoacetone is a water clear liquid. There are great
differences in the properties ascribed to this body by different
investigators. This probably is due to the fact that the monobromo
derivative is mixed with those containing two or more atoms of
bromine. A sample boiling at 126-127° and melting at -54°, had a
specific gravity of 1.631 at 0°. It has a vapor pressure of 9 mm. of
mercury at 20°.
While bromoacetone is a good lachrymator, it possesses the
disadvantage that it is not very stable. Special shell linings are
necessary, and even then the material may be decomposed before
the shell is fired. The Germans used a lead-lined shell, while
considerable work has been carried out in this country with enamel
lined shell. Glass lined shell may also be used. It is interesting to
note that, while bromoacetone decomposes upon standing in the
shell, it is stable upon detonation. No decomposition products are
found after the explosion, and even unchanged liquid is found in the
shell. It may be considered as having a low persistency, since the
odor entirely disappears from the surface of the ground in twenty-
four hours.
Bromoacetone was also used by the Germans in glass hand
grenades (Hand-a-Stink Kugel) and later in metal grenades. The
metal grenades weighed about two pounds and contained about a
pound and a half of the liquid.
Martonite was prepared by the French in an attempt more
completely to utilize the bromine in the preparation of bromoacetone.
They regenerated the bromine by the use of sodium chlorate:

NaClO₃ + 6HBr = NaCl + 3Br₂ + 3H₂O

In practice sulfuric acid is used with the sodium chlorate, so that
the final products are sodium acid sulfate and a mixture of 20 per
cent chloroacetone and 80 per cent bromoacetone, according to the
reaction:

5(CH₃)₂CO + 4Br + H₂SO₄ + NaClO₃ =

4CH₂BrCOCH₃ + CH₂ClCO CH₃ + NaHSO₄ + 3H₂O.
 This product is equally as effective as bromoacetone alone and is
very much cheaper to manufacture. In general its properties
resemble very closely those of bromoacetone.

German Manufacture of Bromoacetone

and Bromomethylethyl ketone[17]
These two products were prepared by identical methods. About
two-thirds of the product produced by the factory was prepared from
methylethyl ketone which was obtained from the product resulting
from the distillation of wood. The method employed was to treat an
aqueous solution of potassium or sodium chlorate with acetone or
methylethyl ketone, and then add slowly the required amount of
bromine. The equation for the reaction in the case of acetone is as
follows:

CH₃COCH₃ + Br₂ = CH₂BrCOCH₃ + HBr

Ten kg.-mols of acetone or methylethyl ketone were used in a
single operation. About 10 per cent excess of chlorate over that
required to oxidize the hydrobromic acid formed in the reaction was
used. The relation between the water and the ketone was in the
proportion of 2 parts by weight of the former to 1 part by weight of
the latter. For 1 kg.-mol. wt. of the ketone, 10 per cent excess over 1
kg. atomic-weight of bromine was used.
The reaction was carried out either in earthenware vessels or in
iron kettles lined with earthenware. The kettles were furnished with a
stirrer made of wood, and varied in capacity from 4,000 to 5,000
liters. They were set in wooden tanks and cooled by circulating
water. The chlorate was first dissolved in the water and then the
ketone added. Into this mixture the bromine was allowed to run
slowly while the solution was stirred and kept at a temperature of
from 30° to 40° C. The time required for the addition of the bromine
was about 48 hrs. When the reaction was complete, the oil was
drawn off into an iron vessel and stirred with magnesium oxide in the
presence of a small amount of water in order to neutralize the free
acid. It was then separated and dried with calcium chloride. At this
point a sample of the material was taken and tested. The product
was distilled to tell how much of it boiled over below 130° when
methylethyl ketone had been used. If less than 10 per cent distilled
over, the bromination was considered to be satisfactory. If, however,
a larger percentage of low boiling material was obtained, the product
was submitted to further bromination. The material obtained in this
way was found on analysis to contain slightly less than the
theoretical amount of monobromoketone.
It was finally transferred by suction or by pressure into tank-
wagons. At first lead-lined tanks were used, but later it was found
that tanks made of iron could be substituted. In order to take care of
the small amount of hydrobromic acid, which is slowly formed, a
small amount of magnesium oxide was added to the material. The
amount of the oxide used was approximately in the proportion of 1
part to 1000 parts of ketone. When the magnesium oxide was used,
it was found that the bromoketone kept without appreciable
decomposition for about 2 months. The yield of the product from 580
kg. of acetone (10 kg.-mol. wts.) was 1,100 kg. The yield from 720
kg. of methylethyl ketone (10 kg.-mol. wts.) was 1,250 kg.

Halogenated Esters
The use of ethyl iodoacetate was advocated at a time when the
price of bromine seemed prohibitive. Because of the relative price of
bromine and iodine under ordinary conditions, it is not likely that it
would be commonly used. However, it is an efficient lachrymator and
is more stable than the halogenated ketones, so that on a smaller
scale it might be advisable to use it.
It is prepared by the reaction of sodium iodide upon an alcoholic
solution of ethyl chloroacetate. It is a colorless oil, boiling at 178-
180° C. (69° C. at 12 mm.) and having a density of about 1.8. It is
very much less volatile than bromoacetone, having a vapor pressure
of 0.54 mm. of mercury at 20° C. Ethyl iodoacetate is about one-third
as toxic as bromoacetone, but has about the same lachrymatory
value.
 Aromatic Halides
“Benzyl bromide” was also used during the early part of the war,
usually mixed with bromoacetone. The material was not pure benzyl
bromide, but the reaction product of bromine upon xylene, and
should perhaps be referred to as “xylyl bromide.”
Pure benzyl bromide is a colorless liquid, boiling at 198-199° C.,
and having an odor reminiscent of water cress and then of mustard
oil. The war gas is probably a mixture of mono- and dibromo
derivatives, boiling at 210-220° C., and having a density at 20° C. of
1.3. The mixture of benzyl and xylyl bromides used by the Germans
was known as “T-Stoff,” while the mixture of 88 per cent xylyl
bromide and 12 per cent bromoacetone was called “Green T-Stoff.”
As in the case of the halogenated acetones, it is necessary to
use lead lined shell for these compounds. Enamel and glass lined
shell may be used and give good results. While they are difficult of
manufacture, satisfactory methods were being developed at the
close of the war.
“T-Stoff” may be detected by the nose in concentrations of one
part in one hundred million of air, and will cause profuse
lachrymation with one part in a million. It is a highly persistent
material and may last, under favorable circumstances, for several
days. While it is relatively non-toxic, French troops were rendered
unconscious by it during certain bombardments in the Argonne in the
summer of 1915.
A number of derivatives of the benzyl halides have been tested
and some have proven to be very good lachrymators. The difficulty
of their preparation on a commercial scale has made it inadvisable to
use them, and especially inasmuch as bromobenzyl cyanide has
proven to be such a valuable compound.

Bromobenzyl Cyanide
 Bromobenzyl cyanide is, chemically, α-bromo-α-tolunitrile, or
phenyl-bromo-acetonitrile, C₆H₅CHBrCN. It is prepared by the
action of bromine upon benzyl cyanide.
Benzyl cyanide is prepared by the action of sodium cyanide upon
a mixture of equal parts of 95 per cent alcohol and benzyl chloride.
The benzyl chloride in turn is obtained by the chlorination of toluene
at 100°. The material must be fairly pure in order that the benzyl
cyanide reaction may proceed smoothly. The cyanide is subjected to
a fractional distillation and that part boiling within 3 degrees (the pure
product boils at 231.7° C.) is treated with bromine vapor mixed with
air. It has been found necessary to catalyze the reaction by sunlight,
artificial light or the addition of a small amount of bromobenzyl
cyanide.
The product obtained from this reaction, if the hydrobromic acid
which is formed is carefully removed by a stream of air, is sufficiently
pure for use as a lachrymator. It melts from 16 to 22° C., while the
pure product melts at 29° C. It cannot be distilled, even in a high
vacuum. It has a low vapor pressure and thus is a highly persistent
lachrymator.
Bromobenzyl cyanide is about as toxic as chlorine, but is many
times as effective a lachrymator as any of the halogenated ketones
or aromatic halides studied. It has a pleasant odor and produces a
burning sensation on the mucous membrane.
Like the other halogen containing compounds, lead or enamel
lined shell are necessary for preserving the material any length of
time. In all of this work the United States was at a very marked
disadvantage. While the Allies and the Germans could prepare
substances of this nature and use them in shell within a month, the
United States was sure that shell filled at Edgewood Arsenal
probably would not be fired within three months. This means that
much greater precautions were necessary, both as to the nature of
the shell lining and as to the purity of the “war gas.”
The question of protection against lachrymatory gases was never
a serious one. During the first part of the war this was amply
supplied by goggles. Later, when the Standard Respirator was
introduced, it was found that ample protection was afforded against
all the lachrymators. Their principal value is against unprotected
troops and in causing men to wear their masks for long periods of
time.
The comparative value of the various lachrymators mentioned
above is shown in the following table:
Bromobenzyl cyanide 0.0003
Martonite 0.0012
Ethyl iodoacetate 0.0014
Bromoacetone 0.0015
Xylyl bromide 0.0018
Benzyl bromide 0.0040
Bromo ketone 0.011
Choroacetone 0.018
Chloropicrin 0.019
The figures give the concentration (milligram per liter of air)
necessary to produce lachrymation. The method used in obtaining
these figures is given in Chapter XXI.
 CHAPTER VIII
CHLOROPICRIN

During the spring of 1917, strange reports came from the Italian
front that the Germans were using a new war gas. This gas, while it
did not seem to be very poisonous, had the combined property of
being a lachrymator and also of causing vomiting. Large number of
casualties resulted through the men being forced to remove their
masks in an atmosphere filled with lethal gases. The gas had the
additional and serious disadvantage of being a very difficult one to
remove completely in the gas mask. The first American masks were
very good when chlorine or phosgene was considered but were of no
value when chloropicrin was used.
One of the interesting facts of chemical warfare is that few if any
new substances were discovered and utilized during the three years
of this form of fighting. Chlorine and phosgene were well known
compounds. And likewise, chloropicrin was an old friend of the
organic chemist. So much so, indeed, that several organic
laboratories prepared the compound in their elementary courses.
Chloropicrin was first prepared by the English chemist,
Stenhouse, in 1848, by the action of bleaching powder upon a
solution of picric acid. This was followed by a careful study of its
physical and chemical properties, few of which have any connection
with its use as a poison gas. The use of picric acid as an explosive
made it very desirable that other raw materials should be used.
Chloroform, which is the ideal source theoretically (since chloropicrin
is nitro-chloroform, Cl₃CNO₂), gave very poor yields. While it may be
prepared from acetone, in fair yields, acetone was about as valuable
during the war as was picric acid. Practically all the chloropicrin used
was prepared from this acid as the raw material.
 Manufacture
In the manufacture of chloropicrin the laboratory method was
adopted. This consisted simply in passing live steam through a
mixture of picric acid and bleaching powder. The resulting
chloropicrin passes out of the still with the steam. There was a
question at first whether a steam jacketed reaction vessel should be
used, and whether stirrers should be introduced. Both types were
tested, of which the simpler form, without steam jacket or stirrer,
proved the more efficient.

Fig. 27.—Interior of Chloropicrin Plant.

The early work was undertaken at the plant of the American

Synthetic Color Company at Stamford, Connecticut. Later a large
plant was constructed at Edgewood Arsenal. At the latter place ten
stills, 8 by 18 feet, were erected, together with the necessary
accessory equipment. The following method of operation was used:
The bleach is mixed with water and stirred until a cream is
formed. This cream is then pumped into the still along with a solution
of calcium picrate (picric acid neutralized with lime). When the
current of live steam is admitted at the bottom of the still, the
temperature gradually rises, until at 85° C. the reaction begins. The
chloropicrin passes over with the steam and is condensed. Upon
standing, the chloropicrin settles out, and may be drawn off and is
then ready for filling into the shell. The yield was about 1.6 times the
weight of picric acid used.

Properties
Chloropicrin is a colorless oil, which is insoluble in water, and
which can be removed from the reaction by distillation with steam. It
boils at 112° C. and will solidify at -69° C. At room temperature it has
a density of 1.69 and is thus higher than chloroform (1.5) or carbon
tetrachloride (1.59). At room temperature it has a vapor pressure of
24 mm. of mercury. It thus lies, in persistency, between such gases
as phosgene on the one hand, and mustard gas on the other, but so
much closer to phosgene that it is placed in the phosgene group.
Chloropicrin is a very stable compound and is not decomposed
by water, acids or dilute alkalies. The reaction with potassium or
sodium sulfite, in which all the chlorine is found as potassium or
sodium chloride, has been used as an analytical method for its
quantitative determination. The qualitative test usually used consists
in passing the gas-air mixture through a heated quartz tube, which
liberates free chlorine. The chlorine may be detected by passing
through a potassium iodide solution containing starch, or by the use
of a heated copper wire gauze, when the characteristic green color is
obtained.
An interesting physiological test has also been developed. The
eye has been found to be very sensitive to chloropicrin. The gas
affects the eye in such a way that its closing is practically involuntary.
A measurable time elapses between the instant of exposure and the
time when the eye closes. Below 1 or 2 parts per million, the average
eye withstands the gas without being closed, though considerable
blinking may be caused. Above 25 parts, the reaction is so rapid as
to render proper timing out of the question. But with concentrations
between 2 and 25 parts, the subject will have an overpowering
impulse to close his eye within 3 to 30 seconds. The time may be
recorded by a stop watch and from the values thus determined a
calibration curve may be plotted, using the concentration in parts per
million and the time to zero eye reaction. Typical figures are given
below. It will be noted that different individuals will vary in their
sensitivity, though the order is the same.

Conc. A B
p.p.m. Seconds Seconds
20.0 4.0 5.0
15.0 5.4 5.4
10.0 7.5 7.5
7.5 9.0 10.0
5.0 13.0 15.0
2.5 18.0 30.0
Fig. 28.—Calibration Curve of Eyes for Chloropicrin.

Protection
Because of the stability of chloropicrin, the question of protection
resolves itself into finding an absorbent which is very efficient in
removing the gas from air mixtures. Fortunately such an agent was
found in the activated charcoal used in the American gas mask. The
removal of the gas appears to take place in two stages. In the first,
the gas is adsorbed in such a way that the long-continued passage
of air does not remove it. In the second, the gas is absorbed, and
this, really excess gas, is removed by pure air passing over the
charcoal. The relation of these two factors has an important bearing
on the quality of charcoal to be used in gas masks. It appears that up
to a certain point an increase of the quality is desirable: beyond this,
it is of doubtful value.
Unlike phosgene, chloropicrin is absorbed equally well at all
temperatures. Moisture on the other hand has a very decided effect.
It appears that charcoal absorbs roughly equivalent weights of
chloropicrin and of water; the presence of water in the charcoal thus
displaces an approximately equal amount of chloropicrin.
In the study of canisters it has been found that the efficiency time
is approximately inversely proportional to the concentration.
Formulas have been calculated to express the relation existing
between concentration and life of the canister, and also between the
rate of flow of the gas and the life.
While water seems to have a decidedly marked effect upon the
life of a canister, this is not true of other gases, and the efficiency of
the canister for each gas is not decreased when used in a binary
mixture.

Tactical Uses
Because of the high boiling point of chloropicrin it can only be
used in shell. The German shell usually contained a mixture of
superpalite (trichloromethyl chloroformate) and chloropicrin, the
relative proportions being about 75 to 25. These were called Green
Cross Shell, from the peculiar marking on the outside of the shell.
Mixtures of phosgene and chloropicrin (50-50) have also been used.
The Allies have used a mixture of 80 per cent chloropicrin and 20
per cent stannic chloride (so-called N. C.). This mixture combines
the advantages of a gas shell with those of a smoke shell, since the
percentage of stannic chloride is sufficiently high to form a very good
cloud. In addition to this, it is believed that the presence of the
chloride increases the rate of evaporation of the chloropicrin. It has
been claimed that the chloride decreases the amount of
decomposition of the chloropicrin upon the bursting of the shell, but
careful experiments appear to show that this decomposition is
negligible and that the stannic chloride plays no part in it. This
mixture was being abandoned at the close of the war.
This N. C. mixture has also been used in Liven’s projectors and
in hand grenades. The material is particularly fitted for hand
grenades, owing to the low vapor pressure of the chloropicrin, and
the consequent absence of pressures even on warm days. As a
matter of fact, it was the only filling used for this purpose, though
later the stannic chloride was changed, owing to the shortage of tin,
to a mixture of silicon and titanium chlorides.
While chloropicrin is sufficiently volatile to keep the strata of air
above it thoroughly poisonous, it is still persistent enough to be
dangerous after five or six hours.
 CHAPTER IX
DICHLOROETHYLSULFIDE
“MUSTARD GAS”

The early idea of gas warfare was that a material, to be of value as

a war gas, should have a relatively high vapor pressure. This would, of
course, provide a concentration sufficiently high to cause casualties
through inhalation of the gas-ladened air. The introduction of “mustard
gas” (dichloroethylsulfide) was probably the greatest single
development of gas warfare, in that it marked a departure from this
early idea, for mustard gas is a liquid boiling at about 220° C., and
having a very low vapor pressure. But mustard gas has, in addition, a
characteristic property which, combined with its high persistency,
makes it the most valuable war gas known at the present time. This
peculiar property is its blistering effect upon the skin. Very low
concentrations of vapor are capable of “burning” the skin and of
producing casualties which require from three weeks to three months
for recovery. The combination of these properties removed the
necessity for a surprise attack, or the building up of a high
concentration in the first few bursts of fire. A few shell, fired over a
given area, were sufficient to produce casualties hours and even days
afterwards.
Mustard gas, chemically, is dichloroethylsulfide (ClCH₂CH₂)₂S.
The name originated with the British Tommy because the crude
material first used by the Germans was suggestive of mustard or
garlic. Various other names were given the compound, such as
“Yellow Cross,” from the shell markings of the Germans; “Yperite,” a
name used by the French, because the compound was first used at
Ypres; and “blistering gas,” because of its peculiar effect upon the
skin.

Historical
 It seems probable that an impure form of mustard gas was
obtained by Richie (1854) by the action of chlorine upon ethyl sulfide.
The substance was first described by Guthrie (1860), who recognized
its peculiar and powerful physiological effects. It is interesting in this
connection to note that Guthrie studied the effect of ethylene upon the
sulfur chlorides, since this reaction was the basis of the method finally
adopted by the Allies.
The first careful investigation of mustard gas, which was then only
known as dichloroethylsulfide, was carried out by Victor Meyer (1886).
Meyer used the reaction between ethylene chlorhydrin and sodium
sulfide, with the subsequent treatment with hydrochloric acid. All the
German mustard gas used during 1917 and 1918 was apparently
made by the use of these reactions, and all the early experimental
work of the Allies was in this direction.
Mustard gas was first used as an offensive agent by the Germans
on July 12-13, 1917, at Ypres. According to an English report, the
physiological properties of mustard gas had been tested by them
during the summer of 1916. The Anti-Gas Department put forward the
suggestion that it should be used for chemical warfare, but at that time
its adoption was not approved. This fact enabled the English to quickly
and correctly identify the contents of the first Yellow Cross dud
received. It is not true, as reported by the Germans, that the material
was first diagnosed as diethylsulfide.
The tactical value of mustard gas was immediately recognized by
the Germans and they used tremendous quantities of it. During ten
days of the Fall of 1917, it is calculated that over 1,000,000 shell were
fired, containing about 2,500 tons of mustard gas. Zanetti states that
the British gas casualties during the month following the introduction of
mustard gas were almost as numerous as all gas casualties incurred
during the previous years of the war. Pope says that the effects of
mustard gas as a military weapon were indeed so devastating that by
the early autumn of 1917 the technical advisers of the British, French,
and American Governments were occupied upon large scale
installations for the manufacture of this material.

Preparation and Manufacture

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