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Edited by
HEW STRACHAN, Professor of International Relations, University of St
Andrews and Emeritus Fellow of All Souls College, Oxford
Huw Bennett
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Information on this title: www.cambridge.org/9781107136380
DOI: 10.1017/9781316479841
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For Claudia, Lina and Orla, with love
Contents
Introduction 1
1 Baggage 13
2 The Army’s Short-Lived Ulster Honeymoon 38
3 Escalation and the Erosion of Impartiality 66
4 Edward Heath’s Bid for Victory 93
5 The Road to Bloody Sunday 122
6 The Most Deadly Year 163
7 Strategy in the Shadow of Loyalist Power 204
8 We Cannot Envisage Peace 247
Conclusion 271
A Note on Sources 277
Acknowledgements 282
Notes 285
Bibliography 381
Index 408
vii
Figures
viii
Maps
ix
Tables
x
Illustrations
xi
Abbreviations
xii
LIST OF ABBREVIATIONS
xiii
LIST OF ABBREVIATIONS
xiv
LIST OF ABBREVIATIONS
xv
I NT R O D U C TI O N
1
Map 1 Northern Ireland.
© Peter Wood, from Operation BANNER by Nick van de Bijl, Pen & Sword Books.
INTRODUCTION
for those making strategy.4 British strategists saw civil war as something
looming on the horizon, to be kept at bay, and at times a reason for invoking
strategic change.
Soldiers at the sharp end shared the belief in their indispensable
presence without always seeing how this might contribute to perpetuating
the conflict. Marine Goulds arrived in the town of Newry, astride Counties
Armagh and Down, six months after completing commando training:
To say the least I was a bit apprehensive about going over to Ulster. I didn’t
know what to expect one way or the other and when you get down to facts it
is the unknown that induces fear . . . there have been bombings, shootings,
arms finds, and two Marines have been killed. Now I believe that Newry is
not a normal British town, but a town where the majority of people wish it
to be so, but are prevented from leading a normal peaceful existence by
a minority of die hard terrorists. It is now my opinion that we have to be
here, that if we withdraw all the British forces from Ulster the people of this
country would suffer far greater than they have done in the past five years.
Because of this we have to stay whether we, or any minority, like it or not.5
Historical knowledge about the Troubles has been extracted for various
purposes. American officers in Iraq after the 2003 invasion wearied of their
British counterparts lecturing them on Northern Ireland – not least because
these lessons came from the campaign’s endgame.6 History deserves more
careful handling. Controversies surrounding the conflict are perpetuated by
a criminal justice approach occupying a space that might better be dealt with
by a move towards truth and reconciliation. Despite allegations about vet-
erans being persecuted, since 2011 the Director of Public Prosecutions (DPP)
for Northern Ireland has brought cases against six military veterans for
conflict legacy offences, compared to twenty-one against ex-paramilitaries.7
In May 2021 criminal proceedings against two former paratroopers for shoot-
ing dead Joe McCann in 1972 collapsed, owing to problems with the prosecu-
tion’s evidence.8 In February 2023 David Holden became the first ex-soldier
to be convicted of a Troubles-related killing since the 1998 Good Friday
Agreement. A judge imposed a three-year suspended sentence for the man-
slaughter of Aidan McAnespie, who was shot at a check-point in County
Tyrone in 1988. The judge criticised Holden for giving ‘a dishonest explan-
ation to the police and then to the court’.9 The prospects for securing
convictions in other historical cases are uncertain even as the victims’ quest
for justice is unimpeachable. Though the conflict is largely over, the major
participants continue to fight a ‘battle for the historical record’.10 Anxieties
over potential prosecutions mean veterans are reluctant to talk, government
3
UNCIVIL WAR
4
INTRODUCTION
5
Map 2 Belfast.
© Peter Wood, from Operation BANNER by Nick van de Bijl, Pen & Sword Books.
INTRODUCTION
those emanating from the United States and the North Atlantic Treaty
Organisation (NATO).31 Whereas the repression motif places blame for
suffering in the early years squarely on the military’s shoulders, studies
framed around reaction to IRA violence or a strategy vacuum end up
removing responsibility from the armed forces.
These accounts need to be questioned. By 1971 mid-ranking officers
were taught: ‘the Army is faced with a situation unlike that previously met
elsewhere. . .. The Army’s previous experience, training and techniques do
not fully cover this situation.’32 The coercive measures applied in the 1970s
never reached the intensity seen in the colonies. Forced population move-
ment, executions and collective punishments never entered the army’s
tactical repertoire in Northern Ireland.33 The colonial continuity narrative
also assumes the army stumbled blindly from one setting into another
without any reflection. In reality, officers observed changes to the strategic
environment during the end of empire, afterwards, and throughout the
Northern Ireland conflict. The repression template cannot account for
variation during the conflict, either in time or place. Military tactics in
January 1970 were markedly different from those in September 1971; prac-
tices in the countryside diverged from those in the major urban centres.
Blaming republicanism is equally misleading. It is true that the PIRA lead-
ership launched an offensive against Britain in January 1970, before the
Falls curfew, internment and Bloody Sunday. Yet focusing solely on the
IRA’s part in starting the Troubles ignores how republicans made choices
in relation to their own communities and their opponents, not in isolation,
as their strategy changed over the years.34
Uncivil War uncovers the running discussions between ministers, offi-
cials and officers rather than looking for a single plan agreed by politicians
and then followed slavishly by soldiers.35 A Ministry of Defence (MOD) civil
servant called the process ‘Defence by Discussion’.36 These debates could be
protracted and fractious.37 Such disputation is normal in armed forces.38
Yet in the British case a reputation for anti-intellectualism means such
debates are sometimes sidelined.39 Studies specifically about civil–military
relations in Northern Ireland remain fixated on a few set-piece turning-
points.40 By exploring strategy in a more dynamic, continual sense this book
illuminates the historical contingencies in which strategists made choices,
downplaying the sense of inevitability so common to accounts of the
conflict.41
Moving beyond a handful of decisions by senior leaders brings two
further benefits. Firstly, the significance of seemingly mundane events
becomes more apparent. Some 250,000 houses were searched in mainly
7
UNCIVIL WAR
8
INTRODUCTION
Map 3 Derry/Londonderry.
© Peter Wood, from Operation BANNER by Nick van de Bijl, Pen & Sword Books.
9
UNCIVIL WAR
10
INTRODUCTION
11
UNCIVIL WAR
12
1
BAGGAGE
When a soldier gets off the ferry from England, Belfast looks the same as
any other large city, he may breathe a sigh of relief. . .. It really looks
quite like England except that the people’s accents are different, but
then they vary all over England. He smiles as he thinks of somebody
from Kent trying to understand a Geordie. But then he starts to realise
that all is not the same as his home in England. You wouldn’t find
barbed wire barricades outside Woolworth’s, would you?1
Royal Regiment of Fusiliers, 1972
After August 1969 the ferries kept coming with their camouflaged passen-
gers for thirty years. The ideas brought by soldiers influenced their conduct
as the conflict expanded, as did the plans made in the years and months
when a military deployment came to seem more likely.2 Historians of
Ireland and writers on the British Army agree colonialism played
a decisive part in the Troubles. The consensus holds that the colonial legacy
loomed large in the army’s tactical repertoire on arrival in Northern
Ireland. There are two problems here: soldiers did not carry their intellec-
tual baggage unthinkingly from the colonies into Northern Ireland. And
what might be considered colonial tactics were notably absent between
August 1969 and May 1970. The colonial imprint on the conflict cannot
be entirely rejected. The whole period up to 1998, when power-sharing
came about, might even be described as a decolonisation process.3
Military thought prior to 1969 disavowed that the army could behave in
a colonial fashion in the United Kingdom. Once the army was on active
operations, this belief contributed to a defensiveness about the army’s
intentions. Ideas about the army’s benign purpose reduced the space for
critical questioning about how soldiers treated civilians.
Debates within the army must be set alongside political developments in
Northern Ireland at the same time. The rapid pace of change in the late
1960s is an essential context for appreciating how soldiers experienced
events, and for remembering that ‘history is made by people who do not
13
UNCIVIL WAR
The British Army’s colonial heritage is obvious and irrefutable.6 For some
the army was: ‘a colonial army, experienced in colonial campaigns. It was
therefore inclined to treat the situation as a colonial one.’7 The prior
experience of senior officers is a case in point. General Sir Ian Freeland
(General Officer Commanding (GOC), 1969–71) served in Cyprus; his
successor from 1971 to 1973, General Sir Harry Tuzo, commanded
a brigade in Borneo. Brigadier Frank Kitson, who commanded 39th
Brigade in Belfast, 1970–2, fought in Kenya and Malaya.8 The robotic
application of colonial methods is seen as a marker of the army’s failure as
a ‘learning institution’, a weak spot diagnosed in twenty-first-century wars
too.9 Blinkered repetition apparently stemmed from an innate anti-
intellectualism.10 In fact the army was more curious than is normally
assumed.
Military embodiments of colonialism in the 1960s cannot be separated
from the deeper, contested relationships between Britain and Ireland. For
some writers any policy pursued by the British government other than
withdrawal constituted colonialism.11 Colonialism can be read into the
modern Troubles in various guises: in an unbroken chain from the
14
BAGGAGE
15
UNCIVIL WAR
16
BAGGAGE
During one training exercise Directing Staff (DS) claimed collective pun-
ishments like curfews, fines and evictions ‘punish simple people who have
acted wrongly under threat of torture or death’. Officers were advised to
avoid them as they alienated people, resulting in a diminished flow of
intelligence. Brutal interrogation, rough searching and stealing from the
population were counterproductive, though ‘We have been guilty of all on
occasions in the past.’42 Writing in a leading military journal, Major Peter de
la Billière argued Aden set a precedent for future wars, where the National
Liberation Front’s skilful propaganda condemned British repression before
a global audience.43
The army’s ability to approach the colonial past with a certain analytical
acuity must be recognised if the decisions taken in Northern Ireland are to
17
UNCIVIL WAR
T H E G R O W I N G R U P T U R E IN NO R T H E R N IR I S H P O L I T I C S
As the British Army came to terms, more or less, with the need to adjust after
empire, politics in Northern Ireland saw a number of crucial developments.
The Unionist Party had been in power continuously since the statelet’s
formation in 1921 without a Catholic ever occupying ministerial office.46
Catholics were persistently ignored in policy-making, despite constituting
34.9 per cent of the population in the 1961 census.47 Captain Terence
O’Neill, Northern Ireland Prime Minister from March 1963 until
May 1969, believed in the need for change. Educated in England, working
in London and Australia and wartime service in the Irish Guards may have
informed his liberal outlook. O’Neill sought to develop a political culture
where Catholics accepted the constitution.48 Assimilating the minority into
the mainstream promised to remove the border as a central issue in
Northern Irish politics: this was to be achieved by improved socio-
economic conditions.49 Elements within unionist politics accepted his ambi-
tions in a context where the United Kingdom’s expanding welfare state,
matched with a modernising ethos, emphasised the benefits that the union
bestowed on all citizens.50 O’Neill appealed to those who believed in an
‘Ulster British ideology’. His supporters identified primarily with Great
Britain and wanted a liberal, democratic Northern Ireland.51 To observers
18
BAGGAGE
in Britain this all appeared rather tame, if worthy. In Northern Ireland such
notions smacked of bold radicalism.
The hope that economic progress might neutralise political grievances
proved to be naïve. Instead, incremental reforms opened up an acrimoni-
ous debate about whether they should happen at all, and if so, how quickly.
But at the beginning the focus on economics got results. Public expenditure
per head rose from 88 per cent of the English level in 1959–60 to
118 per cent in 1969–70, due to O’Neill lobbying the Treasury in London.
Between 1958 and 1970 the Northern Ireland economy grew on average
4.9 per cent each year, compared to 3.6 per cent in the United Kingdom as
a whole. A political thaw complemented these achievements. Sectarian
tensions eased during the ‘Orange–Green’ talks between nationalist and
Orange Order leaders in 1962–3.52 In 1965 the Nationalist Party accepted
the role of Official Opposition in the Northern Ireland House of Commons,
breaking their abstentionist tradition. Catholic politicians were finally
involved in formal political life.53 Opinion polls, always worth reading
cautiously, suggested in the late 1960s that only a minority of Catholics
(34 per cent) were dissatisfied with the constitution. Only 14 per cent
wanted a united Ireland.54 Attitudes held before widespread violence
occurred did not determine what happened later.
Liberal unionist reforms coalesced with demands from the nascent civil
rights movement, born in May 1963 at the formation of the Homeless
Citizens’ League in Dungannon.55 Further campaigning organisations fol-
lowed: most notably the Campaign for Social Justice in 1964, and the
Northern Ireland Civil Rights Association (NICRA) in 1967. NICRA set
out six core demands: one man one vote in local elections; a halt to
gerrymandering of electoral wards to create false unionist majorities; ban-
ning discrimination in government jobs; stopping discrimination in hous-
ing allocation; repealing the Special Powers Act; and for the B Specials
police reserve to be abolished. People joining the movement often found
inspiration in civil rights activism in the United States. Dissatisfaction with
housing attracted particular concern. Although house building was substan-
tial after the Second World War, the new stock was allocated on a sectarian
basis.56 Discontent with political repression formed another major griev-
ance. Stormont used the Civil Authorities (Special Powers) Act to exclude
Catholics from political life. Initially designed to reimpose order after
partition, justification for employing the Act shifted by the 1930s to silen-
cing those who advocated union with the south. Regulations were issued
banning meetings, processions, flying the tricolour, wearing the Easter Lily,
circulating newspapers and singing republican songs.57 The Act remained
19
UNCIVIL WAR
20
BAGGAGE
21
UNCIVIL WAR
Those in the MOD’s Main Building spent much of the late 1960s absorbed
in a major defence review. Defence Secretary Denis Healey announced on
22 February 1966 cuts to equipment programmes, including the CVA-01
aircraft carrier, plus a permanent departure from Aden.90 Over the next two
22
BAGGAGE
Illustration 1.1 Captain Terence O’Neill and Harold Wilson at 10 Downing Street,
5 November 1968.
(Courtesy of Keystone/Hulton Archive/Getty Images.)
23
UNCIVIL WAR
against Catholics. Wilson’s Cabinet ignored both calls to action.97 The pres-
sure in the Commons for intervention had diminished since the 1966 general
election gave Labour a 100-seat majority. Though sympathetic, Labour lead-
ers thought civil rights activists exaggerated their case.98
When they thought about Northern Ireland at all, soldiers liked to dwell
on the Province’s bucolic charms, a leitmotif in recollections of service
there. Cecil Blacker went to Lisburn in 1962 to command 39th Infantry
Brigade. A horse fanatic, he enjoyed participating in riding events north
and south of the border.99 Another officer at the headquarters relished the
‘pleasantly relaxed’ atmosphere, taking up hockey, tennis and dinghy sail-
ing on Loch Neagh.100 Arriving at Palace Barracks for a two-year tour in
June 1968, 2nd Queen’s Regiment reflected: ‘it is hard to imagine that we
can do anything else but thoroughly enjoy our stay here’.101 Later, in
July 1970, 1st King’s Own Scottish Borderers found replenishment in the
Antrim countryside ‘an agreeable change from the streets of Belfast’.102
Even during their difficult 1971 tour in Derry, 2nd Royal Green Jackets
appreciated the ‘exceptionally comfortable’ Shackleton Barracks. As
a residential battalion, many families came with the soldiers – the schools
in Ballykelly and Limavady were deemed far better than those attended by
army children in Germany.103 Officers wrote these accounts. A sergeant
arriving in Omagh with the 4th/7th Royal Dragoon Guards in
September 1966 recalled the unit’s wives’ horror: ‘they had never seen
married quarters like them. We didn’t have fridges or anything.’104
Stephen Robson, based at Ballykinler from October 1968, went on rural
patrols to prevent anticipated IRA sabotage on the electricity network. The
battalion played darts and football against local teams, without noticing any
animosity. Sectarian tensions were invisible to him.105 Charles Millman, an
officer with experience in Berlin, Kenya, Borneo and the MOD, and a Staff
College education, observed the July marching season in Belfast in 1965. Yet
‘the real depth of this divide did not truly reach me – then or throughout
the year I was at Lisburn’.106 Military testimonies refrain from mentioning
Northern Ireland’s constitutional status prior to the army’s active deployment
in 1969; the topic probably did not seem relevant. Sentiments expressed in
the early years may have reflected deeper beliefs. Jim Parker, in Belfast from
mid August 1969, placed Belfast in the same league as Manchester, Dundee
and Liverpool.107 Brigadier James Cowan went to command 8th Brigade in
Derry in January 1970: ‘one was operating in the United Kingdom. We were at
home; these were allegedly our people, and I think it made a difference to the
way people approached their jobs.’108 Another officer, in Northern Ireland
from April to August 1971, shared Cowan’s qualified sense of affinity: ‘you
24
BAGGAGE
25
UNCIVIL WAR
Before and after August 1969 the army and the MOD were torn between
contempt for the Irish and a strong sense of obligation to them. In 1970 the
Army Staff College syllabus covered military aid to the civil power within the
United Kingdom for the first time. The whole subject occupied one after-
noon, including film extracts showing riots in London and Northern
Ireland. Instructing staff were clearly told that Northern Ireland ‘is a very
special case with special factors which do not apply in this country’. Yet
lessons from experience there might be applied in England in the future.118
The ambiguity about Northern Ireland’s filial connections was tangible.
These sentiments appeared in government policy discussions prior to
August 1969 – and not only within the armed forces.
The MOD started taking a closer interest in Northern Ireland in 1966
when intelligence predicted an IRA offensive to mark the 1916 Easter
Rising.119 Any relevant knowledge from the IRA’s 1956–62 border cam-
paign failed to register.120 The Chiefs of Staff have been criticised for
recommending that intelligence-gathering be left to the police rather
than MI5.121 In fact, the decision emanated from MI5. The Security
Service effectively pressed for the police to retain primacy, as ‘IRA activities
constituted a “law and order” problem and were not a security one’.122 The
organisation responsible for tackling subversion within the United
Kingdom refused to do its job in Northern Ireland. By giving so much
power to the RUC, a police force known to have little interest in addressing
loyalism, MI5 made it difficult for the government to understand the danger
from loyalism. Lieutenant-General Sir Geoffrey Baker, the Vice Chief of the
General Staff (VCGS), visited Northern Ireland in late March. His intelli-
gence briefing from the RUC expected the IRA to be planning a long-term
campaign. Baker found these conclusions to be ‘formed on a basis of
reliable information’.123 The most likely time for trouble was expected to
be 16–17 April, so the army despatched an extra battalion between 15 and
20 April, under the cover of a training exercise.124 Not much happened over
Easter 1966. In November the MOD decided to downgrade the Northern
Ireland command to just District status.125
After the disastrous events in Derry on 5 October 1968, Denis Healey
told the home secretary that soldiers lacked training in riot control in the
United Kingdom, and he did not wish them to acquire it.126 The GOC
Northern Ireland, Lieutenant-General Sir Ian Harris, thought major vio-
lence in Derry and Belfast simultaneously was likely to force the police to ask
for assistance. Harris expected military involvement to make matters
worse.127 The MOD instructed Harris to await orders before committing
troops.128 Prime Minister Wilson sought clarification about the legal
26
BAGGAGE
The attorney general backed up Elworthy. So the GOC was now to refer to
the ministry ‘if humanly possible’.134 Healey railed against the common-law
obligation, rather prioritising ‘the requirements of political prudence
which necessitate prior consultation between Ministers before troops are
committed’.135 According to Cecil Blacker, who served in the MOD in the
late 1960s, Healey had a tendency to bully the service chiefs.136 Though
Elworthy only took a third in his Cambridge law degree, he was sure enough
of his ground to insist that ‘it remains illegal under the Common Law for
a military commander to refuse to assist on his own responsibility and
irrespective of what “instructions” he may be given by MOD’.137 His view
reflected an emerging consensus in Whitehall.138 It has been argued that
the army disliked the legal requirement to respond to the civil power’s call
for help, so ignored it.139 However, on 4 January 1969 the minister for home
affairs asked the GOC to put a company of troops on standby in response to
intelligence about an impending IRA attack. Northern Ireland Command
agreed without informing the MOD.140 In the event nothing happened. But
the principle of officers in Northern Ireland taking action without prior
reference to London had been firmly established as legally necessary.
27
Another random document with
no related content on Scribd:
“1. Rapid penetration of the substance into the
cell by virtue of its high lipoid solubility.
2. Hydrolysis by the water within the cell, to form
hydrochloric acid and dihydroxyethylsulphide.
3. The destructive effect of hydrochloric acid upon
some part or mechanism of the cell.
“Although hydrochloric acid does not penetrate
cells readily and is easily neutralized by the buffer
action of the fluids of the body, we might expect by
flooding the body with large quantities of acid to
produce some of the characteristic effects of mustard
gas. Stimulation of the respiratory center is a well
known effect of acid. Convulsions and salivation may
be produced by injection of hydrochloric acid and we
have been able to produce slowing of the heart by
rapid injection of this acid.
“The delayed action of mustard gas might be
explained by the formation of some compound with
some constituent of the blood. However, blood taken
from dogs which had been poisoned with mustard
gas and were exhibiting typical symptoms at the time,
injected into normal dogs produced no effect. Serum
treated in vitro with mustard gas and allowed to stand
and then injected into a dog, produced no effect. The
fluid which is formed in the vesicle and blebs
produced by the application of mustard gas to the
skin produces no mustard gas effects.”
In studying the toxicity of mustard gas for dogs, it was observed
that a concentration of 0.01 mg. per liter could be tolerated indefinitely.
If this value is considered as a threshold value, and subtracted from
the toxicity values for varying periods of time, it is found that there is a
definite relation between the toxic concentration and the time of
exposure. This is expressed by the formula
(C - 0.01)t = K
where C is the concentration observed for a given time
t
. K has the approximate value of 1.7, where
t
varies between 7.5 and 480 minutes.
Vesicant Action
In addition to its toxicity mustard gas is highly important because of
its peculiar irritating effect upon the skin. Its value is seen when we
realize that one part in 14,000,000 is capable of causing conjunctivitis
of the eye and that one part in 3,000,000 and possibly one part in
5,000,000 will cause a skin burn in a sensitive person on prolonged
exposure. According to Warthin, the lesions produced by mustard gas
are those of a chemical, not unlike hydrochloric acid, but of much
greater intensity. The pathology of these lesions has been carefully
studied and fully described by Warthin and Weller in their book on The
Pathology of Mustard Gas. Our observations will therefore be confined
to certain striking features of the vesicant action of this substance.
Diphenylchloroarsine
The best known of the arsenicals, however, is
diphenylchloroarsine or sneezing gas. Although this is an old
compound (having been prepared by German chemists in 1885),
there was no method for its preparation on a large scale when, first
introduced into chemical warfare. It was finally discovered that the
interaction of triphenyl arsine with arsenic trichloride was fairly
satisfactory and a plant was erected for its manufacture.
When pure, diphenylchloroarsine is a colorless solid, melting at
44°. Because of this, it was always used in solution in a toxic gas or
in a shell which contained a large amount of explosive so that on the
opening of the shell the material would be finely divided and
scattered over a wide territory.
Its value lay in the fact that the fine particles readily penetrated
the ordinary mask and caused the irritation of the nose and throat,
which resulted in sneezing. This necessitated the perfection of
special smoke filters to remove the particles, after which the other
toxic materials were removed by the absorbent in the canister.
It causes sneezing and severe burning sensations in the nose,
throat and lungs in concentrations as slight as 1 part in 10 million. In
higher concentrations, say 1 in 200 to 500 thousand it causes severe
vomiting. While neither of these effects are dangerous or very
lasting, still higher concentrations are serious, as in equal
concentrations diphenylchloroarsine is more poisonous than
phosgene.
Various other arsenical chemicals were developed in the
laboratory, but with one or two exceptions they were not as valuable
as diphenylchloroarsine and methyldichloroarsine and were
therefore discarded.
Diphenylchloroarsine
C₆H₅N₂Cl + C₆H₅AsO₃Na₂ +
=
Na₃AsO₃ NaCl + N₂
C₆H₅AsO₃Na₂ + C₆H₅AsO₃H₂ +
=
2HCl 2NaCl
C₆H₅AsO₃H₂ + C₆H₅AsO₂H₂ +
=
SO₂+H₂O H₂SO₄
C₆H₅N₂Cl + (C₆H₅)₂AsO₂Na +
=
C₆H₅AsO₂Na₂ NaCl + N₂
(C₆H₅)₂AsO₂Na + (C₆H₅)₂AsO₂H +
=
HCl NaCl
2(C₆H₅)₂AsO₂H + [(C₆H₅)₂As]₂O +
=
2SO₂ + H₂O 2H₂SO₄
[(C₆H₅)₂As]₂O + 2(C₆H₅)₂AsCl +
=
2HCl H₂O.
“The entire process was carried out at Höchst.
The method used at Höchst was as follows: In
preparing the diazonium solution, 3 kg.-mols of
aniline were dissolved in 3000 liters of water and the
theoretical quantity of hydrochloric acid. The
temperature of the solution was reduced to between
0° and 5° and the theoretical amount of sodium
nitrite added. The reaction was carried out in a
wooden tank of the usual form for the preparation of
diazonium compounds. A solution of sodium
arsenite was prepared which contained 20 per cent
excess of oxide over that required to react with the
aniline used. The arsenous oxide was dissolved in
sodium carbonate, care being taken to have enough
of the alkali present to neutralize all of the acid
present in the solution of the diazonium salt. To the
solution of the sodium arsenite were added 20 kg. of
copper sulfate dissolved in water, this being the
amount required when 3 kg.-mols of aniline are
used. The solution of the diazonium compound was
allowed to flow slowly into the solution of the
arsenite while the temperature was maintained at
15°. The mixture was constantly stirred during the
addition which requires about 3 hrs. After the
reaction was complete, the material was passed
through a filter press in order to remove the coupling
agent and the tar which had been formed.
Hydrochloric acid was next added to the clear
solution to precipitate phenylarsenic acid, the last
portions of which were removed by the addition of
salt.
“The phenylarsenic acid was next reduced to
phenylarsenous acid by means of a solution of
sodium bisulfite, about 20 per cent excess of the
latter over the theoretical amount being used. For
100 parts of arsenic acid, 400 parts of solution were
used. The reaction was carried out in a wooden
vessel and the mixture stirred during the entire
operation. A temperature of 80° was maintained by
means of a steam coil. Phenylarsenous acid
separated as an oil. The aqueous solution was
decanted from the oil, which was dissolved in a
solution of sodium hydroxide, 40° Bé. The solution
of the sodium salt of phenylarsenous acid was
treated with water so that the resulting solution had
a volume of 6 cu. m. when 3 kg.-mols of the salt
were present. Ice was next added to reduce the
temperature to 15° and a solution of benzene
diazonium chloride, prepared in the manner
described for the first operation, was slowly added.
After the coupling, diphenylarsenic acid was
precipitated by means of hydrochloric acid. The acid
was removed by means of a filter press and
dissolved in hydrochloric acid, 20° Bé. For one part
of diphenylarsenic acid, 3 parts of hydrochloric acid
were used. Into this solution was passed 5 per cent
excess of sulfur dioxide over that required for the
reduction. The sulfur dioxide used was obtained
from cylinders which contained it in liquid condition.
“The reduction was carried out in an iron tank
lined with tiles and a temperature of 80° was
maintained. About 8 hrs. were required for the
reaction. The diphenylarsenic acid on reduction by
the sulfur dioxide was converted into
diphenylarsenous oxide which, in the presence of
the hydrochloric acid, was converted into
diphenylchloroarsine, which separated as an oil.
The oil was next removed and heated in the best
vacuum obtainable until it was dry and free from
hydrochloric acid. The compound melted at 34°. It
was placed in iron tanks for shipment. The yield of
diphenylchloroarsine calculated from the aniline
used was from 25 to 30 per cent of the theoretical.
No marked trouble was observed in handling the
materials and no serious poisoning cases were
reported.
Diphenylcyanoarsine
Ethyldichloroarsine