Products of sulfur mustard degradation: Synthesis and characterization of 1-(2-chloroethoxy)-2- [(2-chloroethyl)thio] ethane, related compounds, and derivatives

Article abstract of DOI:10.1080/10426500801963582

A degradation product of sulfur mustard in ton storage containers 1-(2-chloroethoxy)-2-[(2-chloroethyl)thio] ethane (little t ) has been synthesized and characterized along with a number of its derivatives and related compounds. Copyright Taylor & Francis Group, LLC.

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Phosphorus, Sulfur, and Silicon
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Products of Sulfur Mustard
Degradation: Synthesis
and Characterization of 1-
(2-Chloroethoxy)-2- [(2-
chloroethyl)thio] Ethane,
Related Compounds, and
Derivatives
Mark D. Winemiller a & Kenneth Sumpter a
a Edgewood Chemical Biological Center , Aberdeen
Proving Ground, Maryland, USA
Published online: 12 Aug 2008.
To cite this article: Mark D. Winemiller & Kenneth Sumpter (2008) Products
of Sulfur Mustard Degradation: Synthesis and Characterization of 1-(2-
Chloroethoxy)-2- [(2-chloroethyl)thio] Ethane, Related Compounds, and Derivatives,
Phosphorus, Sulfur, and Silicon and the Related Elements, 183:9, 2309-2317, DOI:
10.1080/10426500801963582
To link to this article: http://dx.doi.org/10.1080/10426500801963582
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Phosphorus, Sulfur, and Silicon, 183:2309–2317, 2008
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500801963582
Products of Sulfur Mustard Degradation: Synthesis
and Characterization of 1-(2-Chloroethoxy)-2-
[(2-chloroethyl)thio] Ethane, Related Compounds, and
Derivatives
Mark D. Winemiller and Kenneth Sumpter
Edgewood Chemical Biological Center, Aberdeen Proving Ground,
Maryland, USA
A
degradation product of sulfur mustard in ton storage containers 1-(2-
chloroethoxy)-2-[(2-chloroethyl)thio] ethane (little “t”) has been synthesized and
characterized along with a number of its derivatives and related compounds.
Keywords Degradation products; sulfone; sulfoxide; sulfur; sulfur mustard
INTRODUCTION
Since its introduction on the battlefield in WWI, sulfur mustard, bis(2-
chloroethyl) sulfide, has been an important chemical warfare agent.
In the years since WWI, there have been a number of suspected and
recorded uses of sulfur mustard. Most recently, it was used during the
Iran-Iraq war in the 1980s. Sulfur mustard’s recent utilization, com-
bined with its stockpiling by several countries, ease of production and
potential use by terrorists has resulted in renewed interest and re-
search. A search of Chemical Abstracts gives over 700 references to
sulfur mustard1 in the last five years alone.
The degradation of sulfur mustard in the environment, and in stor-
age is complex. Numerous publications exist on the pathways and prod-
ucts of sulfur mustard degradation under a variety of field and labora-
tory conditions.2 An analysis of sulfur mustard ton containers in the
US stockpile showed in addition to sulfur mustard itself, by-products
formed during manufacturing, and products formed from slow degra-
dation reactions within the storage container. The analysis of these
Received 24 October 2007; accepted 28 December 2007.
This article not subject to United States copyright law.
Address correspondence to Mark D. Winemiller, Edgewood Chemical Biological Cen-
ter, 5183 Blackhawk Road, Aberdeen Proving Ground, MD 21010–5424, USA. (E-mail:
mark.d.winemiller@us.army.mil).
2309

2310
M. D. Winemiller and K. Sumpter
degradation products can be difficult due to their similarity and lack of
easily distinguishable functional groups.
One compound 1-(2-chloroethoxy)-2-[(2-chloroethyl)thio] ethane (4)
has been observed3 spectroscopically in ton container analysis for many
years in concentrations up to 3%. To the best of our knowledge, no report
of an authentic sample of 4 has been published in the open literature,
only spectroscopic observations.4 We would now like to report the syn-
thesis and characterization of molecule 4, along with a number of its
direct derivatives.
RESULTS AND DISCUSSION
1-(2-Chloroethoxy)-2-[(2-chloroethyl)thio] ethane (4) was produced
in two steps from bis(2-chloroethyl)ether and 2-mercaptoethanol
(Scheme 1).
This simple route is vastly scalable and can be performed as a one-
pot reaction with all purification and isolation performed at the end of
the reaction sequence. Methanol, used as the solvent in equation 1 of
Scheme 1 is removed prior to the use of benzene and thionyl chloride
in equation 2 of Scheme 1.
The sulfoxide and sulfone derivatives of sulfur mustard are well
known5 and the corresponding sulfoxide and sulfone derivatives
for both 2-(2-chloroethoxy)ethyl 2-hydroxyethyl sulfide (1) and 1-(2-
chloroethoxy)-2-[(2-chloroethyl)thio] ethane (4) were easily prepared in
reasonable yields using 35% hydrogen peroxide (Schemes 2 and 3).
Compounds 3 and 6 were prepared in identical procedures while
compounds 2 and 5 differed only for reaction time required for oxidation.
The vinyl derivatives for sulfur mustard have also been reported
in the literature.6 The vinyl derivative 7 for 1-(2-chloroethoxy)-2-[(2-
chloroethyl)thio]ethane 4 was prepared in a yield of 29% and has not
SCHEME 1 Short sequence to title product 1-(2-chloroethoxy)-2-[(2-
chloroethyl)thio] ethane 4.

Products of Sulfur Mustard Degradation
2311
SCHEME 2 Conversion of 1 to its sulfoxide and sulfone derivatives.
been optimized. During the investigation of 7, compounds 10 and 11
were isolated, depending on use of reaction solvent, as reaction side
products and were spectroscopically characterized. (Scheme 4).
The vinyl derivatives of 5 and 6 were formed in reasonable yields
by refluxing overnight in triethylamine, followed by chromatographic
work-up (Scheme 5).
SCHEME 3 Conversion of 4 to its sulfoxide and sulfone derivatives.
SCHEME 4 Conversion of 4 to its vinyl derivative and two side products (10
& 11) isolated in the purification of 7.
SCHEME 5 Conversion of 5 & 6 to vinyl derivatives 8 & 9.

2312
M. D. Winemiller and K. Sumpter
CONCLUSION
Overall, this paper describes the synthesis and spectroscopic (NMR
and MS) characterizations of 1-(2-chloroethoxy)-2-[(2-chloroethyl)thio]
ethane 4 and the corresponding compounds that can be associated with
several sulfur mustard degradation pathways. These short syntheses
and corresponding characterizations may be relevant to ongoing inves-
tigations of sulfur mustard and its related compounds and it is our wish
to share this information in a timely and relevant format.
EXPERIMENTAL
General Procedures
Thin Layer Chromatography was performed using Analtech silica gel
GF plates at 250 microns and were developed using iodine. All sol-
vents and reagents were used as received except for acetone, which
was distilled prior to chromatography. Flash chromatography was
performed using 230–400 mesh silica gel. All NMR spectra were
recorded in CDCl3 and were referenced to the NMR solvent signal. 1H
and 13C spectra were recorded on a JOEL ECX-400 NMR instrument.
Mass spectra were recorded using a Hewlett-Packard 5975 series Mass
Selective Detector coupled to a Hewlett-Packard 6890 gas chro-
matogram. Elemental analysis was performed on a Perkin-Elmer 2400
Series II CHNS/O analyzer.
2-(2-Chloroethoxy)ethyl2-hydroxyethyl Sulfide (1)
In a 50-ml round bottom flask sodium (325 mg, 14.15 mmol) was
reacted with 7.5 ml of dried MeOH while cooled in an ice bath. After
reaction of the sodium, mercaptoethanol (1.00 g, 12.83 mmol) was added
and the mixture allowed to stir for 15 min at room temperature. Bis(2-
chloroethyl)ether (15.00 g, 104.9 mmol) was then added to the flask, and
the reaction was stirred overnight. The resulting NaCl precipitate was
filtered, the MeOH removed by rotary evaporation and the resulting oil
was chromatographed using 20% acetone/petroleum ether (Rf = 0.15)
to yield 1.86 g (79%) of 1.
Alternatively, for scale-up purposes upon completion of the reaction,
the NaCl was filtered off through a silica plug using a fine frit and
acetone. The MeOH and acetone are removed by rotary evaporation
and the resulting oil can be distilled at 110◦C at a vacuum of 0.025 mm
after first removing the bis(2-chloroethyl)ether at 35◦C under the same
vacuum using a bath temperature of 55–60◦C. The receiver flask for
the bis(2-chloroethyl)ether should be cooled in an ice bath for better

Products of Sulfur Mustard Degradation
2313
1
recovery and reuse. NMR: H (CDCl3) δ 3.73–3.61 (m, 8H), 2.76–2.73
(m, 5H); 13C NMR (CDCl3) δ 70.8, 70.7, 60.7, 42.5, 35.4, 31.1. MS (EI):
m/z 61 (58), 75 (27), 91 (13), 105 (100), 148 (2), 166 (0.3), 168 (0.1). Anal.
calcd. for C6H13ClO2S: C 39.02; H 7.09; S 17.36. Found: C 38.79 H 6.93
S 17.76.
2-[[2-(2-Chloroethoxy)ethyl]sulfinyl]ethanol (2)
In a 5-ml round-bottom flask 2-(2-chloroethoxy)ethyl 2-hydroxyethyl
sulfide (1) (504 mg, 2.73 mmol) was cooled to 0◦C in an ice bath. The
material was stirred rapidly and hydrogen peroxide (337 mg of 35%,
3.47 mmol of H2O2) was cooled to 0◦C and added dropwise. The mixture
was allowed to warm gradually to room temperature and stirred rapidly
overnight. The product was purified on silica gel (Rf = 0.11) using 60%
acetone/hexanes directly with no additional work-up to yield 413 mg
(76%) of 2.
NMR: 1H (CDCl3) δ 4.26 (br s, 1H), 4.10–4.03 (m, 2H), 3.95–3.87 (m,
2H), 3.73 (td, 2H, J = 4.1, 1.6 Hz), 3.61 (t, 2H, J = 4.1 Hz), 3.09–2.95
(m, 4H); 13C NMR (CDCl3) δ 70.6, 62.8, 54.8, 54.5, 51.8, 42.4. MS (EI):
m/z 63 (100), 76 (33), 107 (29), 128 (10), 130 (4), 147 (5), 165 (3), 183
(0.8), 187 (0.3). Anal. calcd. for C6H13ClO3S: C 35.91; H 6.53; S 15.98.
Found C 35.74 H 6.35 S 15.82.
2-[[2-(2-Chloroethoxy)ethyl]sulfonyl]ethanol (3)
In a flask 2-(2-chloroethoxy)ethyl 2-hydroxyethyl sulfide (1) (501
mg, 2.71 mmol) was mixed with hydrogen peroxide (1.61 g of 35%,
16.53 mmol of H2O2) and stirred rapidly. The mixture was heated in
a 70◦C water bath for 40 min at which time GC/MS analysis showed
the absence of starting material. The solution was cooled and extracted
with CHCl3. The organics were combined and dried with MgSO4 to
yield an oil which was purified on silica gel (Rf = 0.33) using 60% ace-
1
tone/hexanes. Yield 287 mg, 49%) 3. NMR: H (CDCl3) δ 3.99 (t, 2H, J
= 4.1 Hz), 3.86 (t, 2H, J = 4.1 Hz), 3.68 (t, 2H, J = 4.1 Hz), 3.59 (t, 2H, J
= 3.3 Hz), 3.33–3.29 (m, 4H), 3.11 (br s, 1H); 13C NMR (CDCl3) δ 70.8,
64.3, 56.7, 55.9, 54.3, 42.7. MS (EI): m/z 63 (73), 109 (58), 137 (100),
155 (5), 167 (30). Anal. calcd. for C6H13ClO4S: C 33.26; H 6.05; S 14.80.
Found: C 32.89 H 5.96 S 14.85.
1-(2-Chloroethoxy)-2-[(2-chloroethyl)thio]ethane (4)
A solution of 1 (1.75 g, 9.5 mmol) in 20 ml of dried benzene was
stirred at room temperature and thionyl chloride (2.28 g, 19.2 mmol)
was added dropwise. The reaction was stirred for an additional hour
and the benzene was removed by rotary evaporation. Chromatography

2314
M. D. Winemiller and K. Sumpter
(Rf = 0.83) using 20% acetone/petroleum ether gave 4 (1.89 g, 98%) as
a clear colorless oil. NMR: 1H (CDCl3) δ 3.79–3.61 (m, 8H), 2.92 (t, 2H,
J = 5.9 Hz), 2.76 (t, 2H, J = 4.8 Hz); 13C NMR (CDCl3) δ 71.2, 70.9,
43.0, 42.6, 34.6, 31.7. MS (EI): m/z 63 (66), 93 (15), 109 (21), 123 (100),
125 (39), 166 (8), 168 (3). Anal. calcd. for C6H12Cl2OS: C 35.48; H 5.95;
S 15.79. Found: C 35.84 H 5.88 S 16.07.
For scale-up, upon completion of the procedure for 1, the NaCl was
filtered off through silica gel and the MeOH and acetone were removed.
The oil was taken up in benzene and assuming complete conversion,
the requisite amount of thionyl chloride was added dropwise and the
reaction stirred for 1 h at room temperature. The solution was once
again filtered through a silica gel plug and distillation was similar to
1. Removal of the bis(2-chloroethyl)ether was followed by distillation of
4 at 93–95◦C at 0.025 mm of pressure.
1-(2-Chloroethoxy-2[(2-chloroethyl)sulfinyl]ethane (5)
In a 5 ml round-bottomed flask 4 (501 mg, 2.47 mmol) was cooled
to 0◦C and stirred rapidly while hydrogen peroxide (263 mg of 35%,
2.70 mmol of H2O2) also cooled to 0◦C was added dropwise. The mixture
was stirred rapidly at room temperature overnight. GC/MS analysis
indicated a lack of starting material the following morning and the
solution was filtered through silica gel and washed with acetone. The
acetone was removed by rotary evaporation and the oil was purified on
silica gel (Rf = 0.45) using 40% acetone/hexanes to yield 431 mg (80%)
of 5. NMR: 1H (CDCl3) δ 3.84–3.79 (m, 4H), 3.63 (t, 2H, J = 4.2 Hz) 3.52
(t, 2H, J = 4.2 Hz), 3.11–2.99 (m, 3H), 2.84 (m, 1H); 13C NMR (CDCl3) δ
70.8, 62.6, 54.8, 51.8, 42.4, 36.8. MS (EI): m/z 63 (100), 65 (30), 76 (9),
83 (7), 107 (13), 139 (2), 169 (1). Anal. calcd. for C6H12Cl2O2S: C 32.89;
H 5.52; S 14.63. Found: C 32.56 H 5.33 S 14.51.
1-(2-Chloroethoxy-2[(2-chloroethyl)sulfonyl]ethane (6)
In a 5 ml round-bottomed flask 4 (501 mg, 2.47 mmol) was mixed
with hydrogen peroxide (1.88 g of 35%, 19.35 mmol of H2O2) and stirred
rapidly. The mixture was heated in a 70◦C water bath for 40 minutes at
which time GC/MS analysis showed the absence of starting material.
The solution was cooled and added directly to a silica gel column where
the product was eluted (Rf = 0.46) using 30% acetone/hexanes to yield
382 mg (66%) of 6. NMR: 1H (CDCl3) δ 3.87–3.81 (m, 4H), 3.69 (m, 2H),
3.60–3.54 (m, 4H), 3.24 (t, 2H, J = 4.0Hz); 13C NMR (CDCl3) δ 70.9,
64.3, 56.5, 54.2, 42.6, 35.5. MS (EI): m/z 63 (100), 65 (36), 106 (31),
127 (12), 129 (4), 155 (71), 157 (27), 185 (27) 187 (10). Anal. calcd. for
C6H12Cl2O3S: C 30.65; H 5.14; S 13.64. Found: C 30.78 H 5.06 S 13.95.

Products of Sulfur Mustard Degradation
2315
[[2-(2-Chloroethoxy-ethyl]thio]ethene (7)
A solution of 4 (305 mg. 1.50 mmol) in 8.1 ml of ethanol was mixed
with potassium hydroxide (639 mg, 11.39 mmol) and stirred rapidly
overnight. The ethanol was removed under vacuum and the product was
extracted with ether followed by methylene chloride. The organics were
dried with MgSO4 and the solvents removed using rotary evaporation.
Purification on silica gel (Rf = 0.75) using 15% ether/hexanes gave 7
1
as a colorless oil. (73.8 mg, 29%). NMR: H (CDCl3) δ 6.35 (dd, 1H, J
= 12.8, 7.6 Hz), 5.20 (d, 1H, J = 7.6 Hz), 5.15 (d, 1H, J = 12.8 Hz),
3.73–3.68 (m, 4H), 3.61 (t, 2H, J = 4.1 Hz), 2.90 (t, 2H, J = 5.2 Hz);
13C NMR (CDCl3) δ 131.8, 111.4, 71.0, 69.9, 42.6, 30.9. MS (EI): m/z 63
(100), 73 (59), 87 (75), 93 (19), 106 (19), 120 (13), 166 (17), 168 (6). Anal.
calcd. for C6H11ClOS: C 43.24; H 6.65; S 19.24. Found: C 43.31 H 6.76
S 19.48.
[[2-(2-Chloroethoxy)-ethyl]sulfinyl]ethene (8)
A mixture of 1-(2-chloroethoxy-2[(2-chloroethyl)sulfinyl]ethane 5
(400 mg, 1.83 mmol) and triethylamine (1.70 g, 16.79 mmol) in 10 ml of
benzene was refluxed overnight. The resulting solids were filtered and
the solvents removed by rotary evaporation. The resulting oil was puri-
fied on silica gel (Rf = 0.45) using 40% acetone/hexanes to yield 320 mg
(96%) of 8. NMR: 1H (CDCl3) δ 6.50 (dd, 1H, J = 12.6, 7.4 Hz), 5.75 (d,
1H, H = 12.4 Hz), 5.64 (d, 1H, J = 7.4 Hz) 3.63–3.55 (m, 2H), 3.46–3.38
(m, 2H), 3.33 (t, 2H, J = 4.0 Hz), 2.78 (ddd, 1H, J = 10.3, 6.2, 4.0 Hz),
2.55 (ddd, 1H, J = 10.1, 3.5, 3.5); 13C NMR (CDCl3) δ 140.5, 120.4, 70.2,
62.5, 52.9, 42.1. MS (EI): m/z 63 (100), 65 (33), 76 (36), 107 (28), 109 (9),
118 (3), 133 (2), 17 (1). Anal. calcd. for C6H11ClO2S: C 39.45; H 6.07; S
17.55. Found: C 39.15 H 6.29 S 17.69.
[[2-(2-Chloroethoxy)ethyl]sulfonyl]ethene (9)
In
a
25-ml round-bottomed flask 1-chloro-2-[2-(2-chloro-
ethanesulfonyl)-ethoxy]-ethane (6) (394 mg, 1.68 mmol) was dissolved
in 10 ml of benzene with triethylamine (851 mg, 8.43 mmol) and
refluxed overnight. The resulting solids were filtered and the solvents
removed by rotary evaporation. The oil was chromatographed using
1
30% acetone/hexanes (Rf = 0.58) to give 9 (238 mg, 72%). NMR: H
(CDCl3) δ 6.73 (dd, 1H, J = 12.6, 7.6 Hz), 6.30 (d, 1H, J = 12.6 Hz), 6.03
(d, 1H, J = 7.6 Hz), 3.83 (t, 2H, J = 4.1 Hz), 3.65 (t, 2H, J = 4.1 Hz),
3.55 (t, 2H, J = 4.0 Hz), 3.20 (t, 2H, J = 4.3 Hz); 13C NMR (CDCl3) δ
137.5, 128.7, 70.9, 64.3, 54.5, 42.5. MS (EI): m/z 63 (55), 91 (100), 106
(32), 119 (73), 134 (11), 149 (35). Anal. calcd. for C6H11ClO3S: C 36.27;
H 5.58; S 16.14. Found: C 36.30 H 5.56 S 15.91.

2316
M. D. Winemiller and K. Sumpter
1-(2-Chloroethoxy-2[(2-methoxyethyl)thio]ethane (10)
This product was isolated during an attempted synthesis of (7) as a
1
by-product, it had an Rf = 0.67 using 28% acetone/hexanes. NMR: H
(CDCl3) δ 3.62 (t, 2H, J = 4.3 Hz), 3.58 (t, 2H, J = 5.0 Hz), 3.53 (t, 2H,
J = 4.1 Hz), 3.46 (t, 2H, J = 5.0 Hz), 3.26 (s, 3H), 2.66 (td, 4H, J = 5.0,
1.7 Hz); 13C NMR (CDCl3) δ 71.9, 70.8, 70.6, 58.3, 42.4, 31.6, 31.4. MS
(EI): m/z 58 (45), 63 (48), 75 (81), 87 (10), 103 (23), 119 (100), 198 (0.2).
Anal. calcd. for C7H15ClO2S: C 42.31; H 7.61; S 16.14. Found: C 41.93
H 7.27 S 16.30.
1-(2-Chloroethoxy-2[(2-ethoxyethyl)thio]ethane (11)
This product was isolated during the synthesis of (7) as a byproduct,
it had an Rf = 0.51 using 30% ether/hexanes.
NMR: 1H (CDCl3) δ 3.72 (t, 2H, J = 4.3 Hz), 3.68 (t, 2H, J = 5.0 Hz),
3.63–3.57 (m, 4H), 3.50 (q, 2H, J = 5.2 Hz), 2.78–2.73 (m, 4H), 1.19 (t,
3H, J = 5.2Hz); 13C NMR (CDCl3) δ 71.0, 70.9, 70.2, 66.3, 42.6, 32.0,
31.7, 15.1. MS (EI): m/z 59 (74), 63 (65), 72 (74), 75 (100), 88 (20), 103
(25), 133 (79), 167 (4), 212 (0.1). Anal. calcd. for C8H17ClO2S: C 45.17;
H 8.05; S 15.07. Found: C 44.73 H 7.86 S 14.62.
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