Sulfur Mustard
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Mustard gas or sulfur mustard is a
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
belonging to a family of
cytotoxic Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are an immune cell or some types of venom, e.g. from the puff adder (''Bitis arietans'') or brown recluse spider (''Loxosceles reclusa''). Cell physiology Treating cells ...
and
blister agent A blister agent (or vesicant), is a chemical compound that causes severe skin, eye and mucosal pain and irritation. They are named for their ability to cause severe chemical burns, resulting in painful water blisters on the bodies of those affe ...
s known as mustard agents. The name ''mustard gas'' is technically incorrect: the substance, when dispersed, is often not actually a gas, but is instead in the form of a fine mist of liquid droplets.https://www.acs.org/content/dam/acsorg/education/resources/highschool/chemmatters/gc-mustard-gas-personal-safety-and-natl-security.pdf Mustard gases form
blister A blister is a small pocket of body fluid (lymph, serum, plasma, blood, or pus) within the upper layers of the skin, usually caused by forceful rubbing (friction), burning, freezing, chemical exposure or infection. Most blisters are filled wi ...
s on exposed skin and in the lungs, often resulting in prolonged illness ending in death. The active ingredient in typical mustard gas is the organosulfur compound bis(2-chloroethyl) sulfide. In the wider sense, compounds with the structural element are known as ''sulfur mustards'' and ''nitrogen mustards'', respectively. Such compounds are potent
alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effectin ...
s, which can interfere with several biological processes.


History as chemical weapons

As a chemical weapon, mustard gas was first used in
World War I World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, the United States, and the Ottoman Empire, with fightin ...
, and has been used in several armed conflicts since then, including the
Iran–Iraq War The Iran–Iraq War was an armed conflict between Iran and Iraq that lasted from September 1980 to August 1988. It began with the Iraqi invasion of Iran and lasted for almost eight years, until the acceptance of United Nations Security Council ...
, resulting in more than 100,000 casualties. Today, sulfur-based and nitrogen-based mustard agents are regulated under
Schedule 1 Schedule 1 may refer to: * Schedule I Controlled Substances within the US Controlled Substances Act * Schedule I Controlled Drugs and Substances within the Canadian Controlled Drugs and Substances Act * Schedule I Psychotropic Substances within t ...
of the 1993 Chemical Weapons Convention, as substances with few uses other than in
chemical warfare Chemical warfare (CW) involves using the toxic properties of chemical substances as weapons. This type of warfare is distinct from nuclear warfare, biological warfare and radiological warfare, which together make up CBRN, the military acronym ...
(though since then, mustard gas has been found to be useful in cancer
chemotherapy Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemotherap ...
). Mustard agents could be deployed by means of artillery shells,
aerial bomb An aerial bomb is a type of explosive or incendiary weapon intended to travel through the air on a predictable trajectory. Engineers usually develop such bombs to be dropped from an aircraft. The use of aerial bombs is termed aerial bombing. ...
s,
rocket A rocket (from it, rocchetto, , bobbin/spool) is a vehicle that uses jet propulsion to accelerate without using the surrounding air. A rocket engine produces thrust by reaction to exhaust expelled at high speed. Rocket engines work entirely fr ...
s, or by spraying from aircraft.


Synthesis and reactions

Mustard gas can be synthesized in a variety of different ways. In the Depretz method, sulfur dichloride is treated with
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
: : In the Levinstein process,
disulfur dichloride Disulfur dichloride is the inorganic compound of sulfur and chlorine with the Chemical formula, formula S2Cl2. Some alternative names for this compound are ''sulfur monochloride'' (the name implied by its empirical formula, SCl), ''disulphur dich ...
is used instead: : + S8 In the Meyer method,
thiodiglycol Thiodiglycol, or bis(2-hydroxyethyl)sulfide (also known as 2,2-thiodiethanol or TDE), is the organosulfur compound with the formula S(CH2CH2OH)2. It is miscible with water and polar organic solvents. It is a colorless liquid. It is structurall ...
is produced from chloroethanol and potassium sulfide and chlorinated with
phosphorus trichloride Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxi ...
: : In the Meyer–Clarke method, concentrated
hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...
(HCl) is used instead of PCl3: :
Thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...
and phosgene, the latter of which is also a choking agent, have also been used as chlorinating agents. These compounds have the added advantage in that if they are used in excess, they remain as impurities in the finished product and can therefore produce additional mechanisms of toxicity. Mustard gas is a viscous liquid at normal temperatures. The pure compound has a melting point of and decomposes before boiling at . The idealized combustion of mustard gas in oxygen produces
hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...
and
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
, in addition to carbon dioxide and water: : Phosgene, sulfur oxides, and chlorine are also produced in this process. Decontamination of mustard gas can be achieved with
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
, giving
divinyl sulfide Divinyl sulfide is the organosulfur compound with the formula S(CH=CH2)2. It is a colorless liquid with a faint odor. It is found in the oil of some species of ''Allium''. It is notable as the product from hydrogen sulfide and acetylene, a com ...
: : Other compounds that have been used for decontamination include
sodium ethoxide Sodium ethoxide, also referred to as sodium ethylate, is the ionic, organic compound with the formula , or NaOEt (Et = ethane). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol. ...
, which gives ethanol instead of water.


Mechanism of cellular toxicity

Sulfur mustards readily eliminate
chloride The chloride ion is the anion (negatively charged ion) Cl−. It is formed when the element chlorine (a halogen) gains an electron or when a compound such as hydrogen chloride is dissolved in water or other polar solvents. Chloride salts ...
ions by intramolecular
nucleophilic substitution In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The ...
to form cyclic
sulfonium In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion (a " cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula . Together wi ...
ions. These very reactive intermediates tend to permanently
alkylate An alkylation unit (alky) is one of the conversion processes used in petroleum refineries. It is used to convert isobutane and low-molecular-weight alkenes (primarily a mixture of propene and butene) into alkylate, a high octane gasoline componen ...
nucleotide Nucleotides are organic molecules consisting of a nucleoside and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecules wi ...
s in DNA strands, which can prevent cellular division, leading to
programmed cell death Programmed cell death (PCD; sometimes referred to as cellular suicide) is the death of a cell (biology), cell as a result of events inside of a cell, such as apoptosis or autophagy. PCD is carried out in a biological process, which usually confers ...
. Alternatively, if cell death is not immediate, the damaged DNA can lead to the development of cancer.
Oxidative stress Oxidative stress reflects an imbalance between the systemic manifestation of reactive oxygen species and a biological system's ability to readily Detoxification, detoxify the reactive intermediates or to repair the resulting damage. Disturbances ...
would be another pathology involved in mustard gas toxicity. In the wider sense, compounds with the structural element BC2H4X, where X is any
leaving group In chemistry, a leaving group is defined by the IUPAC as an atom or group of atoms that detaches from the main or residual part of a substrate during a reaction or elementary step of a reaction. However, in common usage, the term is often limited ...
and B is a Lewis base, are known as ''mustards''. Such compounds can form cyclic "onium" ions (sulfonium,
ammonium The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary a ...
, etc.) that are good
alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effectin ...
s. Other such compounds are bis(2-haloethyl)ethers (oxygen mustards), the (2-haloethyl)amines (
nitrogen mustard Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen m ...
s), and sesquimustard, which has two α-chloroethyl thioether groups (ClC2H4S−) connected by an ethylene bridge (−C2H4−). These compounds have a similar ability to alkylate DNA, but their physical properties vary.


Physiological effects

Mustard gases react with DNA, which interferes with cellular division and can lead to mutations. Mustard gases are extremely toxic and have powerful
blistering A blister is a small pocket of fluid in the upper layer of the skin caused by heat, electricity, chemicals, light, radiation, or friction Blister(s) or Blistering may also refer to: * Anti-torpedo bulge, also known as an anti-torpedo blister * ...
effects on victims. Their alkylating capabilities make them strongly
carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...
ic and mutagenic. Furthermore, they are highly
lipophilic Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipop ...
, which accelerates their absorption into the body. Because people exposed to mustard agents rarely suffer immediate symptoms, and contaminated areas may appear completely normal, victims can unknowingly receive high doses. Within 24 hours of exposure, victims experience intense
itch Itch (also known as pruritus) is a sensation that causes the desire or reflex to scratch. Itch has resisted many attempts to be classified as any one type of sensory experience. Itch has many similarities to pain, and while both are unpleasant ...
ing and skin irritation. If this irritation goes untreated, blisters filled with yellow fluid (
pus Pus is an exudate, typically white-yellow, yellow, or yellow-brown, formed at the site of inflammation during bacterial or fungal infection. An accumulation of pus in an enclosed tissue space is known as an abscess, whereas a visible collection ...
) can start to form wherever the agent contacted the skin. These are
chemical burn A chemical burn occurs when living tissue is exposed to a corrosive substance (such as a strong acid, base or oxidizer) or a cytotoxic agent (such as mustard gas, lewisite or arsine). Chemical burns follow standard burn classification and may ca ...
s and are very debilitating. Mustard gases easily penetrate clothing fabrics such as wool or cotton, so it is not only exposed skin that gets burned. If the victim's eyes were exposed, then they become sore, starting with
conjunctivitis Conjunctivitis, also known as pink eye, is inflammation of the conjunctiva, outermost layer of the white part of the eye and the inner surface of the eyelid. It makes the eye appear pink or reddish. Pain, burning, scratchiness, or itchiness may ...
(also known as pink eye), after which the eyelids swell, resulting in temporary blindness. Extreme ocular exposure to mustard gas vapors may result in
corneal ulcer Corneal ulcer is an inflammatory or, more seriously, infective condition of the cornea involving disruption of its epithelial layer with involvement of the corneal stroma. It is a common condition in humans particularly in the tropics and the a ...
ation, anterior chamber scarring, and
neovascularization Neovascularization is the natural formation of new blood vessels ('' neo-'' + '' vascular'' + '' -ization''), usually in the form of functional microvascular networks, capable of perfusion by red blood cells, that form to serve as collateral circu ...
. In these severe and infrequent cases, corneal transplantation has been used as a treatment option.
Miosis Miosis, or myosis (), is excessive constriction of the pupil.Farlex medical dictionary
citing: ...
, when the pupil constricts more than usual, may also occur, which is probably the result of the cholinomimetic activity of mustard. At very high concentrations, if inhaled, mustard agents cause bleeding and blistering within the
respiratory system The respiratory system (also respiratory apparatus, ventilatory system) is a biological system consisting of specific organs and structures used for gas exchange in animals and plants. The anatomy and physiology that make this happen varies grea ...
, damaging
mucous membrane A mucous membrane or mucosa is a membrane that lines various cavities in the body of an organism and covers the surface of internal organs. It consists of one or more layers of epithelial cells overlying a layer of loose connective tissue. It is ...
s and causing
pulmonary edema Pulmonary edema, also known as pulmonary congestion, is excessive edema, liquid accumulation in the parenchyma, tissue and pulmonary alveolus, air spaces (usually alveoli) of the lungs. It leads to impaired gas exchange and may cause hypoxemia an ...
. Depending on the level of contamination, mustard agent burns can vary between
first First or 1st is the ordinal form of the number one (#1). First or 1st may also refer to: *World record, specifically the first instance of a particular achievement Arts and media Music * 1$T, American rapper, singer-songwriter, DJ, and rec ...
and
second degree burn A burn is an injury to skin, or other tissues, caused by heat, cold, electricity, chemicals, friction, or ultraviolet radiation (like sunburn). Most burns are due to heat from hot liquids (called scalding), solids, or fire. Burns occur mai ...
s, though they can also be every bit as severe, disfiguring, and dangerous as
third degree burn A burn is an injury to skin, or other tissues, caused by heat, cold, electricity, chemicals, friction, or ultraviolet radiation (like sunburn). Most burns are due to heat from hot liquids (called scalding), solids, or fire. Burns occur mai ...
s. Burns that are severe (i.e. covering more than 50% of the victim's skin) are often fatal, with death occurring after only days or weeks. Mild or moderate exposure to mustard gases is unlikely to kill, though victims still require lengthy periods of medical treatment and
convalescence Convalescence is the gradual recovery of health and strength after illness or injury. It refers to the later stage of an infectious disease or illness when the patient recovers and returns to previous health, but may continue to be a source of ...
before recovery is complete. Mustard gases' carcinogenic and mutagenic effects mean that victims, even if they fully recover, have an increased risk of developing
cancer Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal b ...
later in life. In a study of patients 25 years after wartime exposure to chemical weaponry, c-DNA microarray profiling indicated that 122 genes were significantly mutated in the lungs and airways of mustard gas victims. Those genes all correspond to functions commonly affected by mustard gas exposure, including
apoptosis Apoptosis (from grc, ἀπόπτωσις, apóptōsis, 'falling off') is a form of programmed cell death that occurs in multicellular organisms. Biochemical events lead to characteristic cell changes (morphology) and death. These changes incl ...
, inflammation, and stress responses. The long-term ocular complications include burning, tearing, itching, photophobia, presbyopia, pain, and foreign-body sensations. Mustard gases' blistering effects can be neutralized by
oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
or
chlorination Chlorination may refer to: * Chlorination reaction In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transform ...
, using household bleach (
sodium hypochlorite Sodium hypochlorite (commonly known in a dilute solution as bleach) is an Inorganic chemistry, inorganic chemical compound with the chemical formula, formula NaOCl (or NaClO), comprising a sodium cation () and a hypochlorite anion (or ). It may ...
), or by nucleophilic attack using decontamination solutions such as "DS2" (2%
NaOH Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
, 70%
diethylenetriamine Diethylenetriamine (abbreviated and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. ...
, 28%
2-methoxyethanol 2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for the ...
). After initial decontamination of the victim's wounds is complete, medical treatment is similar to that required by any conventional burn. The degree of pain and discomfort suffered by the victim is also comparable. Mustard agent burns do not heal quickly, and (as with other types of burns) present a risk of
sepsis Sepsis, formerly known as septicemia (septicaemia in British English) or blood poisoning, is a life-threatening condition that arises when the body's response to infection causes injury to its own tissues and organs. This initial stage is follo ...
caused by
pathogen In biology, a pathogen ( el, πάθος, "suffering", "passion" and , "producer of") in the oldest and broadest sense, is any organism or agent that can produce disease. A pathogen may also be referred to as an infectious agent, or simply a germ ...
s such as ''
Staphylococcus aureus ''Staphylococcus aureus'' is a Gram-positive spherically shaped bacterium, a member of the Bacillota, and is a usual member of the microbiota of the body, frequently found in the upper respiratory tract and on the skin. It is often positive ...
'' and ''
Pseudomonas aeruginosa ''Pseudomonas aeruginosa'' is a common encapsulated, gram-negative, aerobic–facultatively anaerobic, rod-shaped bacterium that can cause disease in plants and animals, including humans. A species of considerable medical importance, ''P. aerugi ...
''. The mechanisms behind mustard gas's effect on endothelial cells are still being studied, but recent studies have shown that high levels of exposure can induce high rates of both
necrosis Necrosis () is a form of cell injury which results in the premature death of cells in living tissue by autolysis. Necrosis is caused by factors external to the cell or tissue, such as infection, or trauma which result in the unregulated dige ...
and
apoptosis Apoptosis (from grc, ἀπόπτωσις, apóptōsis, 'falling off') is a form of programmed cell death that occurs in multicellular organisms. Biochemical events lead to characteristic cell changes (morphology) and death. These changes incl ...
. In vitro tests have shown that at low concentrations of mustard gas, where apoptosis is the predominant result of exposure, pretreatment with 50 mM N-acetyl-L-cysteine (NAC) was able to decrease the rate of apoptosis. NAC protects
actin Actin is a family of globular multi-functional proteins that form microfilaments in the cytoskeleton, and the thin filaments in muscle fibrils. It is found in essentially all eukaryotic cells, where it may be present at a concentration of over ...
filaments from reorganization by mustard gas, demonstrating that actin filaments play a large role in the severe burns observed in victims. A British nurse treating soldiers with mustard agent burns during
World War I World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, the United States, and the Ottoman Empire, with fightin ...
commented:


Formulations

In its history, various types and mixtures of mustard gas have been employed. These include: * H – Also known as HS ("Hun Stuff") or ''Levinstein mustard''. This is named after the inventor of the "quick but dirty" Levinstein Process for manufacture, reacting dry
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
with
disulfur dichloride Disulfur dichloride is the inorganic compound of sulfur and chlorine with the Chemical formula, formula S2Cl2. Some alternative names for this compound are ''sulfur monochloride'' (the name implied by its empirical formula, SCl), ''disulphur dich ...
under controlled conditions. Undistilled mustard gas contains 20–30% impurities, which means it does not store as well as HD. Also, as it decomposes, it increases in
vapor pressure Vapor pressure (or vapour pressure in English-speaking countries other than the US; see spelling differences) or equilibrium vapor pressure is defined as the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phases ...
, making the munition it is contained in likely to split, especially along a seam, releasing the agent to the atmosphere. * HD – Codenamed Pyro by the British, and Distilled Mustard by the US. Distilled mustard of 95% or higher purity. The term "mustard gas" usually refers to this variety of mustard. * HT – Codenamed Runcol by the British, and Mustard T- mixture by the US. A mixture of 60% mustard and 40% O-mustard, a related vesicant with lower
freezing point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depends ...
, lower volatility and similar vesicant characteristics. * HL – A blend of distilled mustard (HD) and
lewisite Lewisite (L) (A-243) is an organoarsenic compound. It was once manufactured in the U.S., Japan, Germany and the Soviet Union for use as a Chemical warfare, chemical weapon, acting as a vesicant (blister agent) and lung irritant. Although the substa ...
(L), originally intended for use in winter conditions due to its lower freezing point compared to the pure substances. The lewisite component of HL was used as a form of
antifreeze An antifreeze is an additive which lowers the freezing point of a water-based liquid. An antifreeze mixture is used to achieve freezing-point depression for cold environments. Common antifreezes also increase the boiling point of the liquid, all ...
. * HQ – A blend of distilled mustard (HD) and sesquimustard (Q) (Gates and Moore 1946).


Commonly-stockpiled mustard agents (class)


History


Development

Mustard gases were possibly developed as early as 1822 by César-Mansuète Despretz (1798–1863).By Any Other Name: Origins of Mustard Gas
. Itech.dickinson.edu (2008-04-25). Retrieved on 2011-05-29.
Despretz described the reaction of sulfur dichloride and
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
but never made mention of any irritating properties of the reaction product. In 1854, another French chemist, Alfred Riche (1829–1908), repeated this procedure, also without describing any adverse physiological properties. In 1860, the British scientist
Frederick Guthrie Frederick Guthrie FRS FRSE (15 October 1833 – 21 October 1886) was a British physicist and chemist and academic author. He was the son of Alexander Guthrie, a London tradesman, and the younger brother of mathematician Francis Guthrie. Alon ...
synthesized and characterized the mustard agent compound and noted its irritating properties, especially in tasting. Also in 1860, chemist Albert Niemann, known as a pioneer in
cocaine Cocaine (from , from , ultimately from Quechuan languages, Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly recreational drug use, used recreationally for its euphoria, euphoric effects. It is primarily obtained from t ...
chemistry, repeated the reaction, and recorded blister-forming properties. In 1886,
Viktor Meyer Viktor Meyer (8 September 18488 August 1897) was a German chemist and significant contributor to both organic and inorganic chemistry. He is best known for inventing an apparatus for determining vapour densities, the Viktor Meyer apparatus, and ...
published a paper describing a synthesis that produced good yields. He combined
2-chloroethanol 2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the ''simplest'' beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like od ...
with
aqueous An aqueous solution is a solution in which the solvent is water. It is mostly shown in chemical equations by appending (aq) to the relevant chemical formula. For example, a solution of table salt, or sodium chloride (NaCl), in water would be re ...
potassium sulfide, and then treated the resulting
thiodiglycol Thiodiglycol, or bis(2-hydroxyethyl)sulfide (also known as 2,2-thiodiethanol or TDE), is the organosulfur compound with the formula S(CH2CH2OH)2. It is miscible with water and polar organic solvents. It is a colorless liquid. It is structurall ...
with
phosphorus trichloride Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxi ...
. The purity of this compound was much higher and consequently the adverse health effects upon exposure were much more severe. These symptoms presented themselves in his assistant, and in order to rule out the possibility that his assistant was suffering from a mental illness (psychosomatic symptoms), Meyer had this compound tested on laboratory
rabbit Rabbits, also known as bunnies or bunny rabbits, are small mammals in the family Leporidae (which also contains the hares) of the order Lagomorpha (which also contains the pikas). ''Oryctolagus cuniculus'' includes the European rabbit speci ...
s, most of which died. In 1913, the English chemist Hans Thacher Clarke (known for the Eschweiler-Clarke reaction) replaced the phosphorus trichloride with
hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...
in Meyer's formulation while working with
Emil Fischer Hermann Emil Louis Fischer (; 9 October 1852 – 15 July 1919) was a German chemist and 1902 recipient of the Nobel Prize in Chemistry. He discovered the Fischer esterification. He also developed the Fischer projection, a symbolic way of draw ...
in
Berlin Berlin ( , ) is the capital and largest city of Germany by both area and population. Its 3.7 million inhabitants make it the European Union's most populous city, according to population within city limits. One of Germany's sixteen constitue ...
. Clarke was hospitalized for two months for burns after one of his flasks broke. According to Meyer, Fischer's report on this accident to the
German Chemical Society The German Chemical Society (German: ', GDCh) is a learned society and professional association founded in 1949 to represent the interests of German chemists in local, national and international contexts. GDCh "brings together people working in che ...
sent the
German Empire The German Empire (),Herbert Tuttle wrote in September 1881 that the term "Reich" does not literally connote an empire as has been commonly assumed by English-speaking people. The term literally denotes an empire – particularly a hereditary ...
on the road to chemical weapons. Mustard gas can have the effect of turning a patient's skin different colors, including shades of red, orange, pink, and in unusual cases, blue. The
German Empire The German Empire (),Herbert Tuttle wrote in September 1881 that the term "Reich" does not literally connote an empire as has been commonly assumed by English-speaking people. The term literally denotes an empire – particularly a hereditary ...
during
World War I World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, the United States, and the Ottoman Empire, with fightin ...
relied on the Meyer-Clarke method because
2-chloroethanol 2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the ''simplest'' beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like od ...
was readily available from the German dye industry of that time.


Use

Mustard gas was first used in World War I by the German army against British and Canadian soldiers near
Ypres Ypres ( , ; nl, Ieper ; vls, Yper; german: Ypern ) is a Belgian city and municipality in the province of West Flanders. Though the Dutch name is the official one, the city's French name is most commonly used in English. The municipality co ...
, Belgium, "on the night of July 12, 1917." Later also against the
French Second Army The Second Army (french: IIe Armée) was a field army of the French Army during World War I and World War II. The Army became famous for fighting the Battle of Verdun in 1916 under Generals Philippe Pétain and Robert Nivelle. Commanders World ...
. ''Yperite'' is "a name used by the French, because the compound was first used at Ypres." The Allies did not use mustard gas until November 1917 at
Cambrai Cambrai (, ; pcd, Kimbré; nl, Kamerijk), formerly Cambray and historically in English Camerick or Camericke, is a city in the Nord (French department), Nord Departments of France, department and in the Hauts-de-France Regions of France, regio ...
, France, after the armies had captured a stockpile of German mustard shells. It took the British more than a year to develop their own mustard agent weapon, with production of the chemicals centred on
Avonmouth Docks The Avonmouth Docks are part of the Port of Bristol, in England. They are situated on the northern side of the mouth of the River Avon, opposite the Royal Portbury Dock on the southern side, where the river joins the Severn estuary, within Avo ...
(the only option available to the British was the Despretz–Niemann–Guthrie process). This was used first in September 1918 during the breaking of the
Hindenburg Line The Hindenburg Line (German: , Siegfried Position) was a German defensive position built during the winter of 1916–1917 on the Western Front during the First World War. The line ran from Arras to Laffaux, near Soissons on the Aisne. In 191 ...
. Mustard gas was originally assigned the name LOST, after the scientists Wilhelm Lommel and
Wilhelm Steinkopf Georg Wilhelm Steinkopf (28 June 1879 – 12 March 1949) was a German chemist. Today he is mostly remembered for his work on the production of mustard gas during World War I. Life Georg Wilhelm Steinkopf was born on 28 June 1879 in Staßfurt, in ...
, who developed a method of large-scale production for the
Imperial German Army The Imperial German Army (1871–1919), officially referred to as the German Army (german: Deutsches Heer), was the unified ground and air force of the German Empire. It was established in 1871 with the political unification of Germany under the l ...
in 1916. Mustard gas was dispersed as an
aerosol An aerosol is a suspension (chemistry), suspension of fine solid particles or liquid Drop (liquid), droplets in air or another gas. Aerosols can be natural or Human impact on the environment, anthropogenic. Examples of natural aerosols are fog o ...
in a mixture with other chemicals, giving it a yellow-brown color. Mustard agent has also been dispersed in such munitions as
aerial bomb An aerial bomb is a type of explosive or incendiary weapon intended to travel through the air on a predictable trajectory. Engineers usually develop such bombs to be dropped from an aircraft. The use of aerial bombs is termed aerial bombing. ...
s,
land mine A land mine is an explosive device concealed under or on the ground and designed to destroy or disable enemy targets, ranging from combatants to vehicles and tanks, as they pass over or near it. Such a device is typically detonated automati ...
s, mortar rounds, artillery shells, and
rocket A rocket (from it, rocchetto, , bobbin/spool) is a vehicle that uses jet propulsion to accelerate without using the surrounding air. A rocket engine produces thrust by reaction to exhaust expelled at high speed. Rocket engines work entirely fr ...
s. Exposure to mustard agent was lethal in about 1% of cases. Its effectiveness was as an
incapacitating agent The term incapacitating agent is defined by the United States Department of Defense as: :"An agent that produces temporary physiological or mental effects, or both, which will render individuals incapable of concerted effort in the performance o ...
. The early countermeasures against mustard agent were relatively ineffective, since a soldier wearing a
gas mask A gas mask is a mask used to protect the wearer from inhaling airborne pollutants and toxic gases. The mask forms a sealed cover over the nose and mouth, but may also cover the eyes and other vulnerable soft tissues of the face. Most gas mask ...
was not protected against absorbing it through his skin and being blistered. A common countermeasure was using a urine-soaked mask or facecloth to prevent or reduce injury, a readily available remedy attested by soldiers in documentaries (e.g. ''They Shall Not Grow Old'' in 2018) and others (such as forward aid nurses) interviewed between 1947 and 1981 by the British Broadcasting Corporation for various World War One history programs; however, the effectiveness of this measure is unclear. Mustard gas can remain in the ground for weeks, and it continues to cause ill effects. If mustard agent contaminates one's clothing and equipment while cold, then other people with whom they share an enclosed space could become poisoned as contaminated items warm up enough material to become an airborne toxic agent. An example of this was depicted in a British and Canadian documentary about life in the trenches, particularly once the "sousterrain" (subways and berthing areas underground) were completed in Belgium and France. Towards the end of World War I, mustard agent was used in high concentrations as an area-denial weapon that forced troops to abandon heavily contaminated areas. Since World War I, mustard gas has been used in several wars and other conflicts, usually against people who cannot retaliate in kind:Blister Agent: Mustard gas (H, HD, HS)
, CBWinfo.com
* United Kingdom against the
Red Army The Workers' and Peasants' Red Army (Russian: Рабо́че-крестья́нская Кра́сная армия),) often shortened to the Red Army, was the army and air force of the Russian Soviet Federative Socialist Republic and, after ...
in 1919 * Alleged British use in Mesopotamia in 1920 *
Spain , image_flag = Bandera de España.svg , image_coat = Escudo de España (mazonado).svg , national_motto = ''Plus ultra'' (Latin)(English: "Further Beyond") , national_anthem = (English: "Royal March") , i ...
and
France France (), officially the French Republic ( ), is a country primarily located in Western Europe. It also comprises of Overseas France, overseas regions and territories in the Americas and the Atlantic Ocean, Atlantic, Pacific Ocean, Pac ...
against the Rifian resistance in
Morocco Morocco (),, ) officially the Kingdom of Morocco, is the westernmost country in the Maghreb region of North Africa. It overlooks the Mediterranean Sea to the north and the Atlantic Ocean to the west, and has land borders with Algeria to ...
during the
Rif War The Rif War () was an armed conflict fought from 1921 to 1926 between Spain (joined by History of France, France in 1924) and the Berbers, Berber tribes of the mountainous Rif region of northern Morocco. Led by Abd el-Krim, the Riffians at ...
of 1921–27 (see also: ''
Spanish use of chemical weapons in the Rif War During the Third Rif War in Spanish Morocco between 1921 and 1927, the Spanish Army of Africa deployed chemical weapons in an attempt to put down the Berber rebellion against colonial rule in the region of Rif led by the guerrilla Abd el-Krim. F ...
'') *
Italy Italy ( it, Italia ), officially the Italian Republic, ) or the Republic of Italy, is a country in Southern Europe. It is located in the middle of the Mediterranean Sea, and its territory largely coincides with the homonymous geographical re ...
in
Libya Libya (; ar, ليبيا, Lībiyā), officially the State of Libya ( ar, دولة ليبيا, Dawlat Lībiyā), is a country in the Maghreb region in North Africa. It is bordered by the Mediterranean Sea to the north, Egypt to Egypt–Libya bo ...
in 1930 * The
Soviet Union The Soviet Union,. officially the Union of Soviet Socialist Republics. (USSR),. was a transcontinental country that spanned much of Eurasia from 1922 to 1991. A flagship communist state, it was nominally a federal union of fifteen national ...
in
Xinjiang Xinjiang, SASM/GNC: ''Xinjang''; zh, c=, p=Xīnjiāng; formerly romanized as Sinkiang (, ), officially the Xinjiang Uygur Autonomous Region (XUAR), is an autonomous region of the People's Republic of China (PRC), located in the northwest ...
,
Republic of China Taiwan, officially the Republic of China (ROC), is a country in East Asia, at the junction of the East and South China Seas in the northwestern Pacific Ocean, with the People's Republic of China (PRC) to the northwest, Japan to the northeast ...
, during the Soviet Invasion of Xinjiang against the 36th Division (National Revolutionary Army) in 1934, and also in the
Xinjiang War (1937) In 1937 an Islamic rebellion broke out in southern Xinjiang Province, Republic of China, Xinjiang. The rebels were 1,500 Uighurs, Uighur Muslims led by Kichik Akhund, who was tacitly aided by the new 36th Division, against the pro-Soviet provi ...
in 1936–37 * Italy against
Abyssinia The Ethiopian Empire (), also formerly known by the exonym Abyssinia, or just simply known as Ethiopia (; Amharic and Tigrinya: ኢትዮጵያ , , Oromo: Itoophiyaa, Somali: Itoobiya, Afar: ''Itiyoophiyaa''), was an empire that historica ...
(now
Ethiopia Ethiopia, , om, Itiyoophiyaa, so, Itoobiya, ti, ኢትዮጵያ, Ítiyop'iya, aa, Itiyoppiya officially the Federal Democratic Republic of Ethiopia, is a landlocked country in the Horn of Africa. It shares borders with Eritrea to the ...
) in 1935-1936 * The
Japanese Empire The also known as the Japanese Empire or Imperial Japan, was a historical nation-state and great power that existed from the Meiji Restoration in 1868 until the enactment of the post-World War II 1947 constitution and subsequent forma ...
against
China China, officially the People's Republic of China (PRC), is a country in East Asia. It is the world's most populous country, with a population exceeding 1.4 billion, slightly ahead of India. China spans the equivalent of five time zones and ...
in 1937–1945 * The United States Government tested effectiveness on US Naval recruits in a laboratory setting at The Great Lakes Naval Base, June 3, 1945. * The 2 December 1943 air raid on Bari destroyed an Allied stockpile of mustard gas on the SS ''John Harvey''. * Egypt against
North Yemen North Yemen may refer to: * Mutawakkilite Kingdom of Yemen (1918–1962) * Yemen Arab Republic The Yemen Arab Republic (YAR; ar, الجمهورية العربية اليمنية '), also known simply as North Yemen or Yemen (Sanaʽa), was a ...
in 1963–1967 * Iraq against
Kurds ug:كۇردلار Kurds ( ku, کورد ,Kurd, italic=yes, rtl=yes) or Kurdish people are an Iranian ethnic group native to the mountainous region of Kurdistan in Western Asia, which spans southeastern Turkey, northwestern Iran, northern Ir ...
in the town of
Halabja Halabja ( ku, هەڵەبجە, Helebce, ) is a city in the Kurdistan Region of Iraq and the capital of Halabja Governorate, located about northeast of Baghdad and from the Iranian border. The city lies at the base of what is often referred to ...
during the
Halabja chemical attack The Halabja massacre ( ku, Kêmyabarana Helebce کیمیابارانی ھەڵەبجە), also known as the Halabja chemical attack, was a massacre of Kurdish people that took place on 16 March 1988, during the closing days of the Iran–Iraq War ...
* Iraq against Iranians in 1983–1988 * Possibly in Sudan against insurgents in the
civil war A civil war or intrastate war is a war between organized groups within the same state (or country). The aim of one side may be to take control of the country or a region, to achieve independence for a region, or to change government policies ...
, in 1995 and 1997. * In the
Iraq War {{Infobox military conflict , conflict = Iraq War {{Nobold, {{lang, ar, حرب العراق (Arabic) {{Nobold, {{lang, ku, شەڕی عێراق (Kurdish languages, Kurdish) , partof = the Iraq conflict (2003–present), I ...
, abandoned stockpiles of mustard gas shells were destroyed in the open air, and were used against Coalition forces in
roadside bomb An improvised explosive device (IED) is a bomb constructed and deployed in ways other than in conventional military action. It may be constructed of conventional military explosives, such as an artillery shell, attached to a detonating mechan ...
s. * By
ISIS Isis (; ''Ēse''; ; Meroitic: ''Wos'' 'a''or ''Wusa''; Phoenician: 𐤀𐤎, romanized: ʾs) was a major goddess in ancient Egyptian religion whose worship spread throughout the Greco-Roman world. Isis was first mentioned in the Old Kingd ...
forces against
Kurdish Kurdish may refer to: *Kurds or Kurdish people *Kurdish languages *Kurdish alphabets *Kurdistan, the land of the Kurdish people which includes: **Southern Kurdistan **Eastern Kurdistan **Northern Kurdistan **Western Kurdistan See also * Kurd (dis ...
forces in Iraq in August 2015. * By ISIS against another rebel group in the town of
Mare' Mare' ( ar, مارع ''Māriʿ'', locally pronounced ''Mēreʿ''), also spelled Marea, is a town in northern Aleppo Governorate, northwestern Syria. It is the largest town and administrative centre of the Mare' nahiyah in the Azaz District. Locat ...
in 2015. * According to Syrian State media, by ISIS against
Syrian Army " (''Guardians of the Homeland'') , colors = * Service uniform: Khaki, Olive * Combat uniform: Green, Black, Khaki , anniversaries = August 1st , equipment = , equipment_label = , battles = 1948 Arab–Israeli War Six ...
during the battle in
Deir ez-Zor , population_urban = , population_density_urban_km2 = , population_density_urban_sq_mi = , population_blank1_title = Ethnicities , population_blank1 = , population_blank2_title = Religions , population_blank2 = ...
in 2016. In 1943, during World War II, a shipment of mustard gas from the US exploded aboard SS John Harvey that was bombed during an air raid in the harbor of
Bari Bari ( , ; nap, label= Barese, Bare ; lat, Barium) is the capital city of the Metropolitan City of Bari and of the Apulia region, on the Adriatic Sea, southern Italy. It is the second most important economic centre of mainland Southern Italy a ...
, Italy. Eighty-three of the 628 hospitalized victims who had been exposed to the mustard agent died. After WWII, stockpiled mustard gas was dumped by the British in the sea near
Port Elizabeth Gqeberha (), formerly Port Elizabeth and colloquially often referred to as P.E., is a major seaport and the most populous city in the Eastern Cape province of South Africa. It is the seat of the Nelson Mandela Bay Metropolitan Municipality, Sou ...
, South Africa, resulting in many cases of burns among trawler crews. The use of toxic gases or other chemicals, including mustard gas, during warfare is known as
chemical warfare Chemical warfare (CW) involves using the toxic properties of chemical substances as weapons. This type of warfare is distinct from nuclear warfare, biological warfare and radiological warfare, which together make up CBRN, the military acronym ...
, and this kind of warfare was prohibited by the Geneva Protocol of 1925, and also by the later Chemical Weapons Convention of 1993. The latter agreement also prohibits the development, production, stockpiling, and sale of such weapons. In September 2012, a US official stated that the rebel militant group
ISIS Isis (; ''Ēse''; ; Meroitic: ''Wos'' 'a''or ''Wusa''; Phoenician: 𐤀𐤎, romanized: ʾs) was a major goddess in ancient Egyptian religion whose worship spread throughout the Greco-Roman world. Isis was first mentioned in the Old Kingd ...
was manufacturing and using mustard gas in Syria and Iraq, which was allegedly confirmed by the group's head of chemical weapons development, Sleiman Daoud al-Afari, who has since been captured.


Development of the first chemotherapy drug

As early as 1919 it was known that mustard agent was a suppressor of
hematopoiesis Haematopoiesis (, from Greek , 'blood' and 'to make'; also hematopoiesis in American English; sometimes also h(a)emopoiesis) is the formation of blood cellular components. All cellular blood components are derived from haematopoietic stem cells. ...
. In addition, autopsies performed on 75 soldiers who had died of mustard agent during
World War I World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, the United States, and the Ottoman Empire, with fightin ...
were done by researchers from the
University of Pennsylvania The University of Pennsylvania (also known as Penn or UPenn) is a private research university in Philadelphia. It is the fourth-oldest institution of higher education in the United States and is ranked among the highest-regarded universitie ...
who reported decreased counts of
white blood cell White blood cells, also called leukocytes or leucocytes, are the cell (biology), cells of the immune system that are involved in protecting the body against both infectious disease and foreign invaders. All white blood cells are produced and de ...
s. This led the American Office of Scientific Research and Development (OSRD) to finance the biology and chemistry departments at
Yale University Yale University is a private research university in New Haven, Connecticut. Established in 1701 as the Collegiate School, it is the third-oldest institution of higher education in the United States and among the most prestigious in the wo ...
to conduct research on the use of chemical warfare during World War II. As a part of this effort, the group investigated
nitrogen mustard Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen m ...
as a therapy for
Hodgkin's lymphoma Hodgkin lymphoma (HL) is a type of lymphoma, in which cancer originates from a specific type of white blood cell called lymphocytes, where multinucleated Reed–Sternberg cells (RS cells) are present in the patient's lymph nodes. The condition wa ...
and other types of
lymphoma Lymphoma is a group of blood and lymph tumors that develop from lymphocytes (a type of white blood cell). In current usage the name usually refers to just the cancerous versions rather than all such tumours. Signs and symptoms may include enlar ...
and
leukemia Leukemia ( also spelled leukaemia and pronounced ) is a group of blood cancers that usually begin in the bone marrow and result in high numbers of abnormal blood cells. These blood cells are not fully developed and are called ''blasts'' or ' ...
, and this compound was tried out on its first human patient in December 1942. The results of this study were not published until 1946, when they were declassified. In a parallel track, after the air raid on Bari in December 1943, the doctors of the U.S. Army noted that white blood cell counts were reduced in their patients. Some years after World War II was over, the incident in Bari and the work of the Yale University group with nitrogen mustard converged, and this prompted a search for other similar
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
s. Due to its use in previous studies, the nitrogen mustard called "HN2" became the first cancer
chemotherapy Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemotherap ...
drug,
mustine Chlormethine (INN, BAN), also known as mechlorethamine (USAN, USP), mustine, HN2, and (in post-Soviet states) embikhin (эмбихин), is a nitrogen mustard sold under the brand name Mustargen among others. It is the prototype of alkylating a ...
(also called chlormethine), to be used.


Disposal

In the United States, storage and incineration of mustard gas and other chemical weapons were carried out by the U.S. Army Chemical Materials Agency. Disposal projects at the two remaining American chemical weapons sites were carried out near Richmond, Kentucky, and
Pueblo, Colorado Pueblo () is a List of municipalities in Colorado#Home rule municipality, home rule municipality that is the county seat and the List of municipalities in Colorado, most populous municipality of Pueblo County, Colorado, Pueblo County, Colorado ...
. Although not yet declassified, toxicology specialists who dealt with the accidental puncturing of World War I gas stockpiles add that Air Force bases in Colorado have been made available to assist veterans of the 2003 American war with Iraq in which many Marines were exposed to gas as caches of up to . The United Nations definition of a weapon of mass destruction for mustard gas is , typically the Marines and other coalition allies discovered caches of located across a road from caches as multiple memoirs attest. These were discovered by the assistance of host country allies, or through leaks affecting personnel in an area with a weapon and gas cache called an ASP. New detection techniques are being developed in order to detect the presence of mustard gas and its metabolites. The technology is portable and detects small quantities of the hazardous waste and its oxidized products, which are notorious for harming unsuspecting civilians. The
immunochromatographic Affinity chromatography is a method of separating a biomolecule from a mixture, based on a highly specific macromolecular binding interaction between the biomolecule and another substance. The specific type of binding interaction depends on the ...
assay would eliminate the need for expensive, time-consuming lab tests and enable easy-to-read tests to protect civilians from sulfur-mustard dumping sites. In 1946, 10,000 drums of mustard gas (2,800 tonnes) stored at the production facility of Stormont Chemicals in
Cornwall, Ontario Cornwall is a city in Eastern Ontario, Canada, situated where the provinces of Central Canada, Ontario and Quebec and the state of New York (state), New York converge. It is the seat of the United Counties of Stormont, Dundas and Glengarry, Unit ...
, Canada, were loaded onto 187 boxcars for the journey to be buried at sea on board a long barge south of
Sable Island Sable Island (french: île de Sable, literally "island of sand") is a small Canadian island situated southeast of Halifax, Nova Scotia, and about southeast of the closest point of mainland Nova Scotia in the North Atlantic Ocean. The island i ...
, southeast of Halifax, at a depth of . The dump location is 42 degrees, 50 minutes north by 60 degrees, 12 minutes west. A large British stockpile of old mustard agent that had been made and stored since World War I at
M. S. Factory, Valley The M.S. ( Ministry of Supply) Factory, Valley was a Second World War site in Rhydymwyn, Flintshire, Wales, that was used for the storage and production of mustard gas. It was later also used in the development of the UK's atomic bomb project. M ...
near
Rhydymwyn Rhydymwyn (the name in Welsh means 'Ford of the Ore' and takes its placename from the ford across the River Alyn now replaced by a small iron bridge) is a village in Flintshire, Wales, located in the upper Alyn valley. Once a district of Mold, i ...
in
Flintshire , settlement_type = County , image_skyline = , image_alt = , image_caption = , image_flag = , image_shield = Arms of Flint ...
, Wales, was destroyed in 1958. Most of the mustard gas found in Germany after
World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposin ...
was dumped into the
Baltic Sea The Baltic Sea is an arm of the Atlantic Ocean that is enclosed by Denmark, Estonia, Finland, Germany, Latvia, Lithuania, Poland, Russia, Sweden and the North and Central European Plain. The sea stretches from 53°N to 66°N latitude and from ...
. Between 1966 and 2002, fishermen have found about 700 chemical weapons in the region of
Bornholm Bornholm () is a Danish island in the Baltic Sea, to the east of the rest of Denmark, south of Sweden, northeast of Germany and north of Poland. Strategically located, Bornholm has been fought over for centuries. It has usually been ruled by ...
, most of which contain mustard gas. One of the more frequently dumped weapons was "Sprühbüchse 37" (SprüBü37, Spray Can 37, 1937 being the year of its fielding with the German Army). These weapons contain mustard gas mixed with a
thickener A thickening agent or thickener is a substance which can increase the viscosity of a liquid without substantially changing its other properties. Edible thickeners are commonly used to thicken sauces, soups, and puddings without altering their t ...
, which gives it a tar-like viscosity. When the content of the SprüBü37 comes in contact with water, only the mustard gas in the outer layers of the lumps of viscous mustard
hydrolyzes Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...
, leaving behind amber-colored residues that still contain most of the active mustard gas. On mechanically breaking these lumps (e.g., with the drag board of a fishing net or by the human hand) the enclosed mustard gas is still as active as it had been at the time the weapon was dumped. These lumps, when washed ashore, can be mistaken for amber, which can lead to severe health problems.
Artillery shells A shell, in a military context, is a projectile whose payload contains an explosive, incendiary, or other chemical filling. Originally it was called a bombshell, but "shell" has come to be unambiguous in a military context. Modern usage so ...
containing mustard gas and other toxic ammunition from World War I (as well as conventional explosives) can still be found in France and Belgium. These were formerly disposed of by explosion undersea, but since the current environmental regulations prohibit this, the
French government The Government of France (French: ''Gouvernement français''), officially the Government of the French Republic (''Gouvernement de la République française'' ), exercises executive power in France. It is composed of the Prime Minister, who i ...
is building an automated factory to dispose of the accumulation of chemical shells. In 1972, the
U.S. Congress The United States Congress is the legislature of the federal government of the United States. It is Bicameralism, bicameral, composed of a lower body, the United States House of Representatives, House of Representatives, and an upper body, ...
banned the practice of disposing of chemical weapons into the ocean by the United States. 29,000 tons of nerve and mustard agents had already been dumped into the ocean off the United States by the
U.S. Army The United States Army (USA) is the land service branch of the United States Armed Forces. It is one of the eight U.S. uniformed services, and is designated as the Army of the United States in the U.S. Constitution.Article II, section 2, cl ...
. According to a report created in 1998 by William Brankowitz, a deputy project manager in the U.S. Army Chemical Materials Agency, the army created at least 26 chemical weapons dumping sites in the ocean offshore from at least 11 states on both the
East Coast East Coast may refer to: Entertainment * East Coast hip hop, a subgenre of hip hop * East Coast (ASAP Ferg song), "East Coast" (ASAP Ferg song), 2017 * East Coast (Saves the Day song), "East Coast" (Saves the Day song), 2004 * East Coast FM, a ra ...
and the
West Coast West Coast or west coast may refer to: Geography Australia * Western Australia *Regions of South Australia#Weather forecasting, West Coast of South Australia * West Coast, Tasmania **West Coast Range, mountain range in the region Canada * Britis ...
(in
Operation CHASE Operation CHASE (an acronym for "Cut Holes And Sink 'Em") was a United States Department of Defense program for the disposal of unwanted munitions at sea from May 1964 until the early 1970s.Kurak, Steve "Operation Chase" ''United States Naval Instit ...
, Operation Geranium, etc.). In addition, due to poor recordkeeping, about one-half of the sites have only their rough locations known. In June 1997, India declared its stock of chemical weapons of of mustard gas. By the end of 2006, India had destroyed more than 75 percent of its chemical weapons/material stockpile and was granted extension for destroying the remaining stocks by April 2009 and was expected to achieve 100 percent destruction within that time frame. India informed the United Nations in May 2009 that it had destroyed its stockpile of chemical weapons in compliance with the international Chemical Weapons Convention. With this India has become the third country after South Korea and Albania to do so. This was cross-checked by inspectors of the United Nations. Producing or stockpiling mustard gas is prohibited by the Chemical Weapons Convention. When the convention entered force in 1997, the parties declared worldwide stockpiles of 17,440 tonnes of mustard gas. As of December 2015, 86% of these stockpiles had been destroyed. A significant portion of the United States' mustard agent stockpile was stored at the Edgewood Area of
Aberdeen Proving Ground Aberdeen Proving Ground (APG) (sometimes erroneously called Aberdeen Proving ''Grounds'') is a U.S. Army facility located adjacent to Aberdeen, Harford County, Maryland, United States. More than 7,500 civilians and 5,000 military personnel work at ...
in
Maryland Maryland ( ) is a state in the Mid-Atlantic region of the United States. It shares borders with Virginia, West Virginia, and the District of Columbia to its south and west; Pennsylvania to its north; and Delaware and the Atlantic Ocean to ...
. Approximately 1,621 tons of mustard agents were stored in one-ton containers on the base under heavy guard. A chemical neutralization plant was built on the proving ground and neutralized the last of this stockpile in February 2005. This stockpile had priority because of the potential for quick reduction of risk to the community. The nearest schools were fitted with overpressurization machinery to protect the students and faculty in the event of a catastrophic explosion and fire at the site. These projects, as well as planning, equipment, and training assistance, were provided to the surrounding community as a part of the Chemical Stockpile Emergency Preparedness Program (CSEPP), a joint program of the Army and the
Federal Emergency Management Agency The Federal Emergency Management Agency (FEMA) is an agency of the United States Department of Homeland Security (DHS), initially created under President Jimmy Carter by Presidential Reorganization Plan No. 3 of 1978 and implemented by two Exec ...
(FEMA). Unexploded shells containing mustard gases and other chemical agents are still present in several test ranges in proximity to schools in the Edgewood area, but the smaller amounts of poison gas () present considerably lower risks. These remnants are being detected and excavated systematically for disposal. The U.S. Army Chemical Materials Agency oversaw disposal of several other chemical weapons stockpiles located across the United States in compliance with international chemical weapons treaties. These include the complete incineration of the chemical weapons stockpiled in
Alabama (We dare defend our rights) , anthem = "Alabama (state song), Alabama" , image_map = Alabama in United States.svg , seat = Montgomery, Alabama, Montgomery , LargestCity = Huntsville, Alabama, Huntsville , LargestCounty = Baldwin County, Al ...
,
Arkansas Arkansas ( ) is a landlocked state in the South Central United States. It is bordered by Missouri to the north, Tennessee and Mississippi to the east, Louisiana to the south, and Texas and Oklahoma to the west. Its name is from the Osage ...
,
Indiana Indiana () is a U.S. state in the Midwestern United States. It is the 38th-largest by area and the 17th-most populous of the 50 States. Its capital and largest city is Indianapolis. Indiana was admitted to the United States as the 19th s ...
, and
Oregon Oregon () is a U.S. state, state in the Pacific Northwest region of the Western United States. The Columbia River delineates much of Oregon's northern boundary with Washington (state), Washington, while the Snake River delineates much of it ...
. Earlier, this agency had also completed destruction of the chemical weapons stockpile located on
Johnston Atoll Johnston Atoll is an Unincorporated territories of the United States, unincorporated territory of the United States, currently administered by the United States Fish and Wildlife Service (USFWS). Johnston Atoll is a National Wildlife Refuge and ...
located south of
Hawaii Hawaii ( ; haw, Hawaii or ) is a state in the Western United States, located in the Pacific Ocean about from the U.S. mainland. It is the only U.S. state outside North America, the only state that is an archipelago, and the only stat ...
in the
Pacific Ocean The Pacific Ocean is the largest and deepest of Earth's five oceanic divisions. It extends from the Arctic Ocean in the north to the Southern Ocean (or, depending on definition, to Antarctica) in the south, and is bounded by the continen ...
. The largest mustard agent stockpile, at approximately 6,200
short ton The short ton (symbol tn) is a measurement unit equal to . It is commonly used in the United States, where it is known simply as a ton, although the term is ambiguous, the single word being variously used for short, long, and metric ton. The vari ...
s, was stored at the
Deseret Chemical Depot The Deseret Chemical Depot () was a U.S. Army chemical weapon storage area located in Utah, 60 miles (100 km) southwest of Salt Lake City. It is related to the Tooele Chemical Agent Disposal Facility. History The area was used to store c ...
in northern
Utah Utah ( , ) is a state in the Mountain West subregion of the Western United States. Utah is a landlocked U.S. state bordered to its east by Colorado, to its northeast by Wyoming, to its north by Idaho, to its south by Arizona, and to it ...
. The incineration of this stockpile began in 2006. In May 2011, the last of the mustard agents in the stockpile were incinerated at the Deseret Chemical Depot, and the last artillery shells containing mustard gas were incinerated in January 2012. In 2008, many empty
aerial bomb An aerial bomb is a type of explosive or incendiary weapon intended to travel through the air on a predictable trajectory. Engineers usually develop such bombs to be dropped from an aircraft. The use of aerial bombs is termed aerial bombing. ...
s that contained mustard gas were found in an excavation at the Marrangaroo Army Base just west of Sydney, Australia.Chemical Warfare in Australia
Mustardgas.org. Retrieved on 29 May 2011.
In 2009, a mining survey near
Chinchilla, Queensland Chinchilla is a rural town and locality in the Western Downs Region, Queensland, Australia. In the , the locality of Chinchilla had a population of 6,612 people. Chinchilla is known as the 'Melon Capital of Australia', and plays host to a Melon ...
, uncovered 144 105-millimeter
howitzer A howitzer () is a long- ranged weapon, falling between a cannon (also known as an artillery gun in the United States), which fires shells at flat trajectories, and a mortar, which fires at high angles of ascent and descent. Howitzers, like ot ...
shells, some containing "Mustard H", that had been buried by the U.S. Army during World War II. In 2014, a collection of 200 bombs was found near the
Flemish Flemish (''Vlaams'') is a Low Franconian dialect cluster of the Dutch language. It is sometimes referred to as Flemish Dutch (), Belgian Dutch ( ), or Southern Dutch (). Flemish is native to Flanders, a historical region in northern Belgium; ...
villages of
Passendale Passendale () or Passchendaele (; obsolete spelling, retained in English; vls, Passchendoale) is a rural Belgian village in the Zonnebeke municipality of West Flanders province. It is close to the town of Ypres, situated on the hill ridge sepa ...
and
Moorslede Moorslede () is a municipality located in the Belgian province of West Flanders. The municipality comprises the towns of Dadizele, Slypskapelle and Moorslede proper. On 1 January 2006, Moorslede had a total population of 10,618. The total area is ...
. The majority of the bombs were filled with mustard agents. The bombs were left over from the German army and were meant to be used in the
Battle of Passchendale The Third Battle of Ypres (german: link=no, Dritte Flandernschlacht; french: link=no, Troisième Bataille des Flandres; nl, Derde Slag om Ieper), also known as the Battle of Passchendaele (), was a campaign of the First World War, fought by t ...
in World War I. It was the largest collection of chemical weapons ever found in Belgium. A large amount of chemical weapons, including mustard gas, was found in a neighborhood of
Washington DC ) , image_skyline = , image_caption = Clockwise from top left: the Washington Monument and Lincoln Memorial on the National Mall, United States Capitol, Logan Circle, Jefferson Memorial, White House, Adams Morgan, ...
. The cleanup was completed in 2021.


Post-war accidental exposure

In 2002, an archaeologist at the Presidio Trust archaeology lab in San Francisco was exposed to mustard gas, which had been dug up at the
Presidio of San Francisco The Presidio of San Francisco (originally, El Presidio Real de San Francisco or The Royal Fortress of Saint Francis) is a park and former U.S. Army post on the northern tip of the San Francisco Peninsula in San Francisco, California, and is part o ...
, a former military base. In 2010, a clamming boat pulled up some old
artillery Artillery is a class of heavy military ranged weapons that launch munitions far beyond the range and power of infantry firearms. Early artillery development focused on the ability to breach defensive walls and fortifications during siege ...
shells of World War I from the
Atlantic Ocean The Atlantic Ocean is the second-largest of the world's five oceans, with an area of about . It covers approximately 20% of Earth's surface and about 29% of its water surface area. It is known to separate the " Old World" of Africa, Europe ...
south of
Long Island, New York Long Island is a densely populated island in the southeastern region of the U.S. state of New York, part of the New York metropolitan area. With over 8 million people, Long Island is the most populous island in the United States and the 18th ...
. Multiple fishermen suffered from blistering and respiratory irritation severe enough to require hospitalization.


WWII-era tests on men

From 1943 to 1944, mustard agent experiments were performed on Australian service volunteers in tropical
Queensland, Australia ) , nickname = Sunshine State , image_map = Queensland in Australia.svg , map_caption = Location of Queensland in Australia , subdivision_type = Country , subdivision_name = Australia , established_title = Before federation , established_ ...
, by
British Army The British Army is the principal land warfare force of the United Kingdom, a part of the British Armed Forces along with the Royal Navy and the Royal Air Force. , the British Army comprises 79,380 regular full-time personnel, 4,090 Gurk ...
and American experimenters, resulting in some severe injuries. One test site, the
Brook Islands National Park The Brook Islands National Park is a national park in Cassowary Coast Region, Queensland, Australia, 1246 km northwest of Brisbane, with an area of 0.9 km2. It was established in 1994 and comprises three islands (North, Tween and Mid ...
, was chosen to simulate Pacific islands held by the
Imperial Japanese Army The was the official ground-based armed force of the Empire of Japan from 1868 to 1945. It was controlled by the Imperial Japanese Army General Staff Office and the Ministry of the Army, both of which were nominally subordinate to the Emperor o ...
. The United States tested sulfur mustards and other chemical agents including
nitrogen mustard Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen m ...
s and
lewisite Lewisite (L) (A-243) is an organoarsenic compound. It was once manufactured in the U.S., Japan, Germany and the Soviet Union for use as a Chemical warfare, chemical weapon, acting as a vesicant (blister agent) and lung irritant. Although the substa ...
on up to 60,000 servicemen during and after WWII. The experiments were classified secret and as with
Agent Orange Agent Orange is a chemical herbicide and defoliant, one of the "tactical use" Rainbow Herbicides. It was used by the U.S. military as part of its herbicidal warfare program, Operation Ranch Hand, during the Vietnam War from 1961 to 1971. It ...
, claims for medical care and compensation were routinely denied, even after the WWII-era tests were declassified in 1993. The
Department of Veterans Affairs The United States Department of Veterans Affairs (VA) is a Cabinet-level executive branch department of the federal government charged with providing life-long healthcare services to eligible military veterans at the 170 VA medical centers an ...
stated that it would contact 4,000 surviving test subjects but failed to do so, eventually only contacting 600. Skin cancer, severe eczema, leukemia, and chronic breathing problems plagued the test subjects, some of whom were as young as 19 at the time of the tests, until their deaths, but even those who had previously filed claims with the VA went without compensation. African-American servicemen were tested alongside white men in separate trials to determine whether their skin color would afford them a degree of immunity to the agents, and
Nisei is a Japanese-language term used in countries in North America and South America to specify the ethnically Japanese children born in the new country to Japanese-born immigrants (who are called ). The are considered the second generation, ...
servicemen, some of whom had joined after their release from Japanese American Internment Camps were tested to determine susceptibility of
Japanese military personnel Japanese may refer to: * Something from or related to Japan, an island country in East Asia * Japanese language, spoken mainly in Japan * Japanese people, the ethnic group that identifies with Japan through ancestry or culture ** Japanese diaspor ...
to these agents. These tests also included
Puerto-Rican Puerto Rico (; abbreviated PR; tnq, Boriken, ''Borinquen''), officially the Commonwealth of Puerto Rico ( es, link=yes, Estado Libre Asociado de Puerto Rico, lit=Free Associated State of Puerto Rico), is a Caribbean island and Unincorporated ...
subjects.


Detection in biological fluids

Concentrations of thiodiglycol in urine have been used to confirm a diagnosis of chemical poisoning in hospitalized victims. The presence in urine of 1,1'-sulfonylbismethylthioethane (SBMTE), a conjugation product with glutathione, is considered a more specific marker, since this metabolite is not found in specimens from unexposed persons. In one case, intact mustard gas was detected in postmortem fluids and tissues of a man who died one week post-exposure.R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 10th edition, Biomedical Publications, Seal Beach, CA, 2014, pp. 1892–1894.


See also

*
Bis(chloromethyl) ether Bis(chloromethyl) ether is an organic compound with the chemical formula (CH2Cl)2O. It is a colourless liquid with an unpleasant suffocating odour and it is one of the chloroalkyl ethers. Bis(chloromethyl) ether was once produced on a large scale ...
*
Blister agent A blister agent (or vesicant), is a chemical compound that causes severe skin, eye and mucosal pain and irritation. They are named for their ability to cause severe chemical burns, resulting in painful water blisters on the bodies of those affe ...
*
Chlorine gas Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is ...
* Half mustard * Keen as Mustard *
Lewisite Lewisite (L) (A-243) is an organoarsenic compound. It was once manufactured in the U.S., Japan, Germany and the Soviet Union for use as a Chemical warfare, chemical weapon, acting as a vesicant (blister agent) and lung irritant. Although the substa ...
*
Nitrogen mustard Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen m ...
*
Phosgene oxime Phosgene oxime, or CX, is an organic compound with the formula Cl2CNOH. It is a potent chemical weapon, specifically a nettle agent. The compound itself is a colorless solid, but impure samples are often yellowish liquids. It has a strong, disag ...
*
Poison gas in World War I The use of toxic chemicals as weapons dates back thousands of years, but the first large scale use of chemical weapons was during World War I. They were primarily used to demoralize, injure, and kill entrenched defenders, against whom the indisc ...
* Rawalpindi experiments * Selenium mustard *
Yellow Cross (chemical warfare) Yellow Cross (Gelbkreuz) is a World War I chemical warfare agent usually based on sulfur mustard (mustard gas, HS, Yperite, Lost). The original Gelbkreuz was a composition of 80–90% of sulfur mustard and 10–20% of tetrachloromethane or chlor ...
*
Mustard (condiment) Mustard is a condiment made from the mustard seed, seeds of a mustard plant (white/yellow mustard, ''white mustard, Sinapis alba''; brown mustard, ''Brassica juncea''; or black mustard, ''Brassica nigra''). The whole, ground, cracked, or bruise ...


Further reading


Mustard gas (Sulphur Mustard) (IARC Summary & Evaluation, Supplement7, 1987)
Inchem.org (1998-02-09). Retrieved on 2011-05-29. * * *
Sulfur mustards are viscous liquids at room temperature and have an odor resembling
mustard plant The mustard plant is any one of several plant species in the genera ''Brassica'' and ''Sinapis'' in the family Brassicaceae (the mustard family). Mustard seed is used as a spice. Grinding and mixing the seeds with water, vinegar, or other liqui ...
s,
garlic Garlic (''Allium sativum'') is a species of bulbous flowering plant in the genus ''Allium''. Its close relatives include the onion, shallot, leek, chive, Allium fistulosum, Welsh onion and Allium chinense, Chinese onion. It is native to South A ...
, or
horseradish Horseradish (''Armoracia rusticana'', syn. ''Cochlearia armoracia'') is a perennial plant of the family Brassicaceae (which also includes mustard, wasabi, broccoli, cabbage, and radish). It is a root vegetable, cultivated and used worldwide ...
, hence the name. When pure, they are colorless, but when used in impure forms, such as in warfare, they are usually yellow-brown.


References


External links


Textbook of Military Medicine – Intensive overview of mustard gas
Includes many references to scientific literature

* Shows photographs taken in 1996 showing people with mustard gas burns.

(Caution: contains graphic images)


UMDNJ-Rutgers University CounterACT Research Center of Excellence
A research center studying mustard gas, include
searchable reference library
with many early references on mustard gas. *


surgical treatment of mustard gas burns

UK Ministry of Defence Report on disposal of weapons at sea and incidents arising

Rhydymwyn Valley History Society

The advent of mustard gas in 1917, Simon Jones

Measures to protect against mustard gas, 1917-1918, Simon Jones
{{DEFAULTSORT:Mustard gas Thioethers Organochlorides Blister agents World War I chemical weapons IARC Group 1 carcinogens Chloroethyl compounds Sulfur mustards