Oxidative Neutralization of Mustard-Gas Simulants in an On-Board Flow Device with In-Line NMR Monitoring

Article abstract of DOI:10.1002/anie.201702744

The fast and effective neutralization of the mustard-gas simulant 2-chloroethyl ethyl sulfide (CEES) using a simple and portable continuous flow device is reported. Neutralization takes place through a fully selective sulfoxidation by a stable source of hydrogen peroxide (alcoholic solution of urea–H₂O₂ adduct/MeSO₃H freshly prepared). The reaction progress can be monitored with an in-line benchtop NMR spectrometer, allowing a real-time adjustment of reaction conditions. Inherent features of millireactors, that is, perfect control of mixing, heat and reaction time, allowed the neutralization of 25 g of pure CEES within 46 minutes in a 21.5 mL millireactor (t^R=3.9 minutes). This device, which relies on affordable and nontoxic reagents, fits into a suitcase, and can be deployed by police/military forces directly on the attack site.

Full text of DOI:10.1002/anie.201702744

A Journal of the Gesellschaft Deutscher Chemiker
Angewandte
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Accepted Article
Title: Oxidative Neutralization of Mustard-Gas Simulants in an On-
Board Flow Device with In-Line NMR Monitoring
Authors: Baptiste PICARD, Boris GOUILLEUX, Thomas LEBLEU,
Jacques MADDALUNO, Isabelle CHATAIGNER, Maël
PENHOAT, François-Xavier FELPIN, Patrick GIRAUDEAU,
and Julien LEGROS
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201702744
Angew. Chem. 10.1002/ange.201702744
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http://dx.doi.org/10.1002/ange.201702744

10.1002/anie.201702744
Angewandte Chemie International Edition
COMMUNICATION
Oxidative Neutralization of Mustard-Gas Simulants in an On-
Board Flow Device with In-Line NMR Monitoring
Baptiste Picard,a Boris Gouilleux,b Thomas Lebleu,a Jacques Maddaluno,a Isabelle Chataigner,a Maël
Penhoat,d François-Xavier Felpin,b,c* Patrick Giraudeaub,c* and Julien Legrosa*
Abstract: The fast and effective neutralization of the mustard-gas
simulant 2-chloroethyl ethyl sulfide (CEES) using a simple and
portable continuous flow device is reported. Neutralization takes place
through a fully selective sulfoxidation by a stable source of hydrogen
peroxide (alcoholic solution of urea-H2O2 adduct/MeSO3H freshly
prepared). The reaction progress can be monitored with an in-line
benchtop NMR spectrometer, allowing a real-time adjustment of
reaction conditions. Inherent features of millireactors, i.e. perfect
control of mixing, heat and reaction time, allowed the neutralization of
25 g of pure CEES within 46 min in a 21.5 mL millireactor (tR = 3.9
min). This device, which relies on affordable and nontoxic reagents,
fits into a suitcase, and can be deployed by police/military forces
directly on the attack site.
explains the poor efficiency of the hydrolysis path. In contrast,
oxidation has to be regarded as the method of choice to neutralize
this CWA, at least if the process retained is very selective toward
the sulfoxide, since overoxidation affords a highly toxic sulfone
(Scheme 1).
Cl
O
O
S
S
toxic
toxic
Cl
Cl
less toxic
−HCl
O
S
O
O
[O]
[O]
HD
S
Cl
Cl
Cl
Cl
HDO2
HDO
Scheme 1. Oxidation of mustard gas yperite (HD) into the corresponding
sulfoxide (HDO) and sulfone (HDO2).
The use of chemical weapons by terrorist groups has become a
plausible threat since several chemical warfare agents (CWA) are
currently available to perpetrators, including mustard compounds
with the simplest bis(2-chloroethyl) sulfide as prominent
member.[1,2] This blister agent is well known under common
names such as mustard agent, yperite or HD; this viscous liquid
is used as a weapon through dispersion by spraying or explosion,
hence the denomination “mustard gas”. The extreme toxicity of
HD is due to the equilibrium with the strongly electrophilic
episulfonium form, which also makes it carcinogenic (Scheme 1).
Conventional processes for the destruction of large quantities of
mustard agents (e.g. shells from World War I, Syrian stockpiles)
require highly secure sites, specifically dedicated for this purpose.
The neutralization/destruction of chemical warfare agents is
generally conducted under harsh conditions i.e., direct pyrolysis,
hydrolysis in strongly basic solutions or transformations with
aggressive oxidants.[3–6] The limited solubility of HD in water
In recent years, the academic community has made
progresses towards the implementation of highly selective
sulfoxidation of HD simulants with peroxides, singlet oxygen,
hypochlorite, for instance, in the presence of metal promoters
(including polyoxometallates and metal-organic framework) or in
microemulsion media.[7–17] However, most of these protocols are
unsuited for large scales or use in real situation. Considering that
the terrorist threat would most likely embody the form of a small
and concealable chemical bomb introduced into a densely
populated area, the possibility of intervening directly on site
represents a decisive advantage. Therefore, the deployment of
robust and transportable equipment allowing a rapid and selective
oxidation of mustard gas is of utmost importance. Continuous flow
devices fulfil all these requirements: they are compact systems
which allow high control on reaction time as well as on heat and
mass transfer, and the process can be easily up-scaled without
optimization of new conditions.[18,19] Moreover, hazardous
chemicals such as oxidants are easily handled in a flow
system,[20–24] and it offers the possibility of automation and in-line
analysis.[25–27] Herein we show that the fast neutralization of sulfur
mustard simulants can be achieved by fully selective oxidation in
a flow apparatus monitored by an in-line 1H NMR low-field
instrument (Scheme 2).
[a]
[b]
B. Picard, Dr. T. Lebleu, Dr. J. Maddaluno, Prof. I. Chataigner,
Dr. J. Legros
Normandie Université, INSA Rouen, UNIROUEN, CNRS, COBRA
laboratory (UMR 6014 & FR3038), 76000 Rouen, France
E-mail: julien.legros@univ-rouen.fr
B. Gouilleux, Prof. F.-X. Felpin, Dr. P. Giraudeau
CEISAM CNRS, UMR6230, Université de Nantes, BP 92208
2 rue de la Houssinière, 44322 Nantes, France
E-mail: patrick.giraudeau@univ-nantes.fr
E-mail: fx.felpin@univ-nantes.fr
[c]
[d]
Prof. F.-X. Felpin, Dr. P. Giraudeau
Institut Universitaire de France
1 rue Descartes, 75005 Paris
Dr. M. Penhoat
Université de Lille, CNRS, USR 3290, MSAP, Miniaturisation pour la
Synthèse l'Analyse et la Protéomique, F-59000 Lille, France
oxidant
O
in-line
NMR
S
R
Cl
S
R
Cl
R = Ph (CEPS), Et (CEES)
R = Ph (CEPSO), Et (CEESO)
Supporting information for this article is given via a link at the end of
the document.
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10.1002/anie.201702744
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Scheme 2. An integrated flow system with in-line NMR monitoring for the
sulfoxidation of mustard simulants chloroethyl phenyl sulfide (CEPS) and
chloroethyl ethyl sulfide (CEES).
sulfoxide CEESO in >99% yield. Similar results (conditions and
yield) were obtained with CEPS.[37,38]
UHP, MSA
in MeOH
O
The toolbox of organic chemists overflows with oxidants,
among which hydrogen peroxide is certainly one of the most
convenient to use, especially under its UHP form (urea-H2O2
adduct; mp 90 °C), a very stable solid, hence transportable,
source of anhydrous hydrogen peroxide. Whereas H2O2 generally
requires the assistance of a promoter for efficient oxygen transfer,
it has been shown that the simple use of hexafluoroisopropanol
(HFIP) as solvent was able to efficiently activate the oxidant;[28–31]
this activation is mostly due to an increase of the electrophilicity
of peroxide oxygen through strong H-bonding with the
solvent.[31,32] Notably, Bégué reported that complete oxidation of
various sulfides into sulfoxides was attained within only 5 min
reaction time.[28] Hence, a preliminary experiment involving
mustard gas simulants (CEPS and CEES) and a solution of UHP
(2 equiv.) in HFIP was run in a classical batch setup (Scheme 3).
S
R
Cl
S
R
Cl
R = Ph (CEPS), Et (CEES)
O
S
Ph
Cl
Figure 1. Continuous flow set-up for the oxidation of half-mustards CEPS and
CEPSO (100%)
CEES with UHP/MSA in methanol. See supporting information for details.
UHP (2 equiv.)
HFIP, RT
S
R
Cl
O
S
S
Cl
R = Ph (CEPS)
Et (CEES)
+
S
These developments can be supported by the implementation
of in-line analytical methods capable of monitoring the reaction on
the fly. This enables the real-time characterization of reaction
products, kinetic studies and the optimization of the reaction
conditions. Obviously, high-field NMR spectrometers are not
portable, but recent years have witnessed the use of compact
NMR spectrometers for these purposes, either under a by-pass
configuration[39–42] or within a flow chemistry platform.[43] We
incorporated such a low-field NMR system within our continuous
flow system in order to evaluate the residence time tR at which the
maximal conversion of CEES into the sulfoxyde CEESO is
achieved (Figure 2). However, performing the reaction with short
tR (less than 1 min) in our setup involved high flow-rates, which
significantly impact the sensitivity and the resolution of the NMR
experiments. A first feature – commonly called “inflow effect” – is
the continuous replenishment of the excited spins by unexcited
ones. The latter must spend a sufficient time within the pre-
polarization volume to reach their full thermal polarization. When
the flow rate is too high, the saturated spins are refreshed by non-
polarized ones leading to a loss of sensitivity.[44–46] Another
feature involved by flow NMR – known as “outflow effect” – makes
the use of high-flow regimes even more problematic. When the
receiver is open during the detection of a flowing sample, some
polarized and excited spins leave out the sensitive volume before
the end of the acquisition.[44,46] This phenomenon leads to a
reduction of the effective transverse relaxation time and involves
Cl
Cl
CEESO (80%)
bisCEES (20%)
Scheme 3. Oxidation of half-mustards CEPS and CEES with UHP in HFIP
Full conversion of both substrates rapidly occurred and CEPS
underwent fully selective sulfoxidation (CEPSO). However CEES,
the closest analogue of the real warfare agent HD,[33] was
converted into sulfoxide CEESO (80%), along with 20% of a
dimeric sulfonium salt (bisCEES), whose formation has already
been described, among several products, during hydrolysis.[34]
A
blank NMR experiment was then performed by diluting CEES in
pure HFIP and after only 5 minutes, the dimeric sulfonium salt
(bisCEES), was formed selectively. The possible reversible
dimerization of the bisCEES in the presence of UHP was
evaluated on a benchmark test, but unfortunately, after 15 days
of stirring the dimeric sulfonium salts remained very stable. Thus,
to avoid this competitive and irreversible dimerization affording a
compound of unknown toxicity, we switched to the less polar
solvent methanol,[35,36] in the presence of methanesulfonic acid as
proton donor to dissociate/activate UHP. Actually, CEES proved
to remain stable in a MSA/methanol mixture for hours in the
absence of oxidant. These new conditions (methanol/MSA/UHP)
were implemented in a two-stream flow reactor shown on Figure
1. Neat CEES (23.36 mL, 0.2 mol), was pumped at a flow rate of
0.5 mL min−1 and met in a T-shaped mixer a solution of UHP (1.3
equiv.), MSA (2.6 equiv.) in MeOH (30 equiv.) pumped at a flow
rate of 5 mL min−1. The resulting stream entered in a PFA tubing
reactor (ID = 1.6 mm, L = 10.7 m, V = 21.5 mL) with a residence
time of tR = 3.9 min. The reactor outlet was then collected into a
bottle containing 40 mL of 10% (w/w) aqueous NaHSO3.
a
significant line-broadening. Here, these limitations were
circumvented by finely tuning the flow system, consisting in
reducing the reactor volume and previously dissolving the neat
CEES in methanol (further details are available in Supporting
Information). Thanks to this optimization, it was possible to assess
the conversion rate on a range of tR from 16.2 to 100.8 s without
exceeding a flow-rate of 3 mL.min-1, which is an acceptable flow
Therefore,
a simple extraction afforded the corresponding
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Figure 2. Continuous flow system including a benchtop NMR spectrometer
directly connected to the outlet of the reactor
regime in our NMR flow system regarding the aforementioned
limitations. The benchtop NMR spectrometer employed in this
study (Spinsolve from Magritek) works at 43.62 MHz, relies on a
permanent magnet and works without deuterated solvents.[47]
This reduces the cost of the monitoring and avoids undesired
isotopic effects. The downside of using non-deuterated methanol
is the overlap between the huge solvent signal and the
resonances of interest. This drawback became even more critical
at high flow-rates (e.g. 3 mL.min-1) due to the inherent line
broadening occurring with flowing samples.[44,45] To outmatch this
limitation, we implemented a tailored NMR pulse sequence
capable of suppressing multiple solvent resonances at low
magnetic field under flow conditions. The experiment combined a
continuous presaturation with a WET-180-NOESY scheme that
we recently described (see Supporting Information for pulse
sequence and the experimental section for parameters).[46] The
WET-180 block,[48] added during the preparation step, combines
a train of selective shaped pulses applied together with gradient
spoilers to selectively disperse the longitudinal component of the
solvent magnetization. The scheme includes a hard 180° pulse
directly after the last selective pulse with a modification of the flip
angle providing a narrower residual solvent signal with a cleaner
phase. This block was followed by a NOESY excitation with a two-
step phase cycling leading to a reduction of the faraway solvent
effect and a flatter baseline close to the residual solvent signal.[49]
As a result of the efficient solvent signal suppression, the CEESO
peak at 3.8 ppm could be detected and monitored through the
flow reaction. The experiments were carried out at decreasing
flow rates, i.e. at increasing residence times. The overlapping
triplets at 1.25 ppm – arising from the overlaps between the
methyl groups of CEES and CEESO – progressively turned into a
simple triplet matching with the disappearance of CEES (Figure
3). The conversion rate as a function of tR was monitored by
computing the ratio between the peak area of the signals at 3.8
and 1.25 ppm for each kinetic point. Figure 3 displays the
percentage of sulfoxide computed for six different residence
times: full conversion is reached within 67 s, stressing the
efficiency of the neutralization method.
In conclusion, we have implemented a simple and mobile
device allowing fast neutralization of mustard gas simulants. The
neutralization occurs through complete and fully selective
sulfoxidation (>99%) in a millitube reactor using a handy oxidizing
system (an alcoholic mixture of highly stable urea-H2O2 adduct
and methane sulfonic acid) that can be readily prepared on
demand for on site operation. Intensification at multi-gram scale
has been performed and showed full reproducibility: 25 g of neat
half-mustard CEES have been neutralized within 46 min, and
kilogram scale could be reached by using adequate pumps
without any further changes. When optimized, an in-line real-time
monitoring of the reaction efficiency is possible thanks to tailored
spectroscopic methods on a benchtop NMR spectrometer. In
practice, our mobile device could be embarked in a vehicle for
field intervention: the toxic agent would be directly pumped from
the suspicious gear into the millireactor and neutralized on site.[50]
100%
80%
NMR
UHP/MSA
(MeOH)
CEES
tR (s)
60%
CEESO
0
20
40
60
80
100
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Figure 3. Neutralization of CEES monitored by an in-line NMR system. (Top
and middle) two NMR spectra recorded at different tR. Note that the peak with a
* corresponds to a 13C satellite line from the residual solvent signal at 3.3 ppm.
(Bottom) Percentage of CEESO as a function of the residence time.
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The authors gratefully acknowledge support from the CNRS
« Attentats Recherche » program. J.L. is grateful to Dr M. De
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from Normandie Université also thank the Labex SYNORG (ANR-
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CRUNCh network) and the European France (Manche)–England
cross-border cooperation program INTERREG IV A “AI-CHEM
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(grant RésoNantes) for financial support. FXF and PG are
members of the Institut Universtaire de France (IUF).
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Keywords: chemical warfare agent • hydrogen peroxide •
oxidation • benchtop NMR spectrometry • continuous flow
[37] Same results were obtained with ethanol as solvent.
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temperature (40 °C), UHP amount (2.6 eq) or residence time (8 min)
afforded 5-10% sulfone.
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Entry for the Table of Contents (Please choose one layout)
COMMUNICATION
Baptiste Picard, Boris Gouilleux,
Thomas Lebleu, Jacques Maddaluno,
Isabelle Chataigner, Maël Penhoat,
François-Xavier Felpin,* Patrick
Giraudeau* and Julien Legros*
Page No. – Page No.
Mustard gas simulant 2-chloroethyl ethyl sulfide (CEES) was fully neutralized by
selective oxidation into sulfoxide (CEESO) under continuous flow with in-line NMR
monitoring. 25 g of pure CEES have been converted into CEESO (>99%) within 46
min in a 21.5 mL millireactor (tR = 3.9 min). This flow device is small enough to be
moved by security forces and used directly on the site of a chemical threat.
Oxidative Neutralization of Mustard-
Gas Simulants in an On-Board Flow
Device with In-Line NMR Monitoring
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