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Encyclopedia > Mustard gas
Sulfur mustard (HD)
Sulfur Mustard
General
Systematic name Bis (2-chloroethyl) sulfide
Other names Senfgas
Sulfur mustard
Lost
Iprit
Kampstoff "Lost"
Yperite
Yellow Cross Liquid
Molecular formula C4H8Cl2S
Molar mass 159 g/mol
Appearance Water clear if pure.
Normally pale yellow to black.
Slight garlic type odor.
CAS number [505-60-2, 39472-40-7, 68157-62-0]
Properties
Density and phase 1.27 g/ml, liquid
Solubility in water Negligible
Melting point 14 °C
Boiling point 217 °C
Vapor pressure 0.11 mmHg @ 25 °C
Hazards
MSDS External MSDS
Main hazards Vesicant
NFPA 704
Image:nfpa h4.png Image:nfpa f1.png Image:nfpa r1.png
Airborne exposure
limit
0.003 mg/m3
Flash point 105 °C
Related compounds
Related compounds Nitrogen mustard
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Mustard gas is a chemical compound that was first used as a chemical weapon in World War I. In pure form, it is a colorless, odorless, viscous liquid at room temperature and causes blistering of the skin. The name comes from impure mustard gas, which is usually yellow-brown in color and has an odor resembling mustard, garlic or horseradish. It is otherwise not related to mustard in any way. The term "mustard gas" usually refers to sulfur mustard, but a less-common nitrogen mustard also exists. Mustard Gas structural formula - (ClCH2CH2)2S Created with xymtex by Maxim Iorsh documentclass{letter} usepackage{epic,aliphat} pagestyle{empty} begin{document} rtrigonal{0==S;2==CH$_2$---CH$_2$---Cl;3==CH$_2$---CH$_2$---Cl} end{document} This image has been released into the public domain by its creator... IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of an element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... Alternate use: Boiling Point, a film by Takeshi Kitano; Boiling Points, a television series The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... The vapor pressure is the pressure (if the vapor is mixed with other gases, the partial pressure) of a vapor(this vapour being formed from molecules/atoms escaping from a liquid/solid). ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Worker safety and health is the prevention and reduction of the number of occupational safety and health hazards at the places of employment, providing safe and healthful working conditions. ... A vesicant (also known as a blister agent) is a chemical agent that causes blistering of the skin. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... There is a live album by the Rolling Stones called Flashpoint The flash point of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... The nitrogen mustards are cytotoxic chemotherapy agents similar to mustard gas. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... Dressing the wounded during a gas attack by Austin O. Spare, 1918. ... World War I was primarily a European conflict with many facets: immense human sacrifice, stalemate trench warfare, and the use of new, devastating weapons - tanks, aircraft, machine guns, and poison gas. ... For the plant and spice of the same name, see the article on mustard. ... Binomial name Allium sativum L. Garlic (Allium sativum) is a bulbous perennial food plant of the family Alliaceae. ... Binomial name Armoracia rusticana P.G. Gaertn. ... The nitrogen mustards are cytotoxic chemotherapy agents similar to mustard gas. ...


It was first synthesised by Frederick Guthrie in 1860, though it is possible that it was developed as early as 1822 by M Depretz. V Meyer would publish a paper in 1886 describing a synthesis which produced good yields. The abbreviation LOST comes from the names Lommel and Steinkopf, who developed a process for mass producing the gas for war use at the German company Bayer AG. Frederick Guthrie was a scientific writer and professor in London who lived from 1833 to 1886. ... 1860 is the leap year starting on Sunday. ... 1822 was a common year starting on Tuesday (see link for calendar). ... 1886 is a common year starting on Friday (click on link to calendar) // Events January 18 - Modern field hockey is born with the formation of The Hockey Association in England. ... Lommel is a municipality located in the Belgian province of Limburg. ... Mass production is the production of large amounts of standardised products on production lines. ... Bayer AG (German pronunciation BYE-er, in US usually pronounced BAY-er) (NYSE: BAY, TYO: 4863 ) is a German chemical and pharmaceutical company founded in 1863. ...


Mustard gas is referred to by numerous other names, including HD, senfgas, sulfur mustard, blister gas, s-lost, lost, Kampfstoff LOST, yellow cross liquid, and yperite. Categories: Stub | Chemical weapons ...


Mustard gas is now listed in schedule 1 of the Chemical Weapons Convention, and as such its production is prohibited. This article is being considered for deletion in accordance with Wikipedias deletion policy. ... Chemical Weapons Convention Opened for signature January 13, 1993 at Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preperatory Commission Parties 170 The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and...

Contents


Variations of sulfur mustard

In its history, several varieties and mixtures of sulfur mustard have been employed. Some of those varieties are listed below:

  • HD – Sulfur mustard that has been purified by washing and vacuum distillation. The term "mustard gas" usually refers to this variety of sulfur mustard.
  • HLevinstein mustard, which contains about 30% sulfur impurities and has a stronger vesicant action.
  • HT – A blend of 60% sulfur mustard (HD) and 40% T (a related vesicant with lower freezing point and much lower volatility, with reportedly similar characteristics)
  • HL – A blend of sulfur mustard (HD) and lewisite (L)
  • HQ – A blend of sulfur mustard (HD) and sesquimustard (Q)

Vacuum distillation is a method of distillation whereby the pressure above the solution to be distilled is reduced to less than one Atmosphere (unit) causing evaporation of the most volatile liquid(s) (those with the lowest boiling points. ... A vesicant (also known as a blister agent) is a chemical agent that causes blistering of the skin. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... Volatility is the standard deviation of the change in value of a financial instrument with a specific time horizon. ... Chemical structure of Lewisite Lewisite is a chemical compound from a chemical family called arsines. ...

Chemistry

Chemically, it is a thioether with the formula C4H8Cl2S. Its structure can be described as 1,1-thio-bis-[2-chloroethane], (ClCH2CH2)2S, 2,2′-dichlorodiethyl sulfide or bis-(2-chloroethyl)-sulfide. Mustard gas can be synthesized by reacting sulfur dichloride (SCl2) with two moles of ethylene (C2H4). A thioether (also known as a sulfide) is a functional group in organic chemistry that has the structure R-S-R, where R is any organic group. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ...


Although the compound is commonly known as "mustard gas", it is a viscous liquid at normal temperatures. The pure compound has a melting point of 14°C (57°F) and decomposes before boiling at 218°C (423°F).


The compound readily eliminates chloride ion by intramolecular nucleophilic substitution to form a cyclic sulfonium ion. This very reactive intermediate is particularly detrimental to cellular health as it has a strong tendency to bond to the guanine nitrogen in DNA strands. This leads to either immediate cellular death or, as recent research has found, cancer. Mustard gas is not very soluble in water but is very soluble in fat, contributing to its rapid absorption into the skin. Guanine is one of the five main nucleobases found in nucleic acids (, DNA and RNA). ... Space-filling model of a section of DNA molecule Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions specifying the biological development of all cellular forms of life (and most viruses). ... When normal cells are damaged beyond repair, they are eliminated by apoptosis. ...


In the wider sense, compounds with the structural element BCH2CH2X, where X is any leaving group and B is a Lewis base are known as mustards. Such compounds can form cyclic onium ions that readily react with nucleophiles. Examples are bis-(2-chloroethyl)ether or the (2-haloethyl)amines. A leaving group is an atom or molecule that detaches from an organic molecule, which, after detachment, is called the residual or main part. ... A Lewis base is any molecule or ion that can form a new covalent bond by donating a pair of electrons. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ...


Physiological effects

Mustard gas is a strong vesicant (a compound that causes blisters). Those exposed usually suffer no immediate symptoms. The exposure develops (in 4 to 24 hours) into deep, itching or burning blisters wherever the mustard contacted the skin; the eyes (if exposed) become sore and the eyelids swollen, possibly leading to conjunctivitis and blindness. At very high concentrations, if inhaled, it causes bleeding and blistering within the respiratory system, damaging the mucous membrane and leading to pulmonary edema. Blister agent exposure over more than 50% body surface area is usually fatal A vesicant (also known as a blister agent) is a chemical agent that causes blistering of the skin. ... A blister caused by a second-degree burn. ... This article needs to be cleaned up to conform to a higher standard of quality. ... The mucous membranes (or mucosae; singular: mucosa) are linings of ectodermic origin, covered in epithelium, and are involved in absorption and secretion. ... Edema (BE: oedema, formerly known as dropsy) is swelling of any organ or tissue due to accumulation of excess fluid. ...


Skin damage can be reduced if povidone iodine in a base of glycofurol is rapidly applied, but since mustard initially has no symptoms, the exposure is usually not identified until the blisters rise. The vesicant property can be neutralised by oxidation or chlorination, common bleach (NaOCl-) can be used or decontamination solution "DS2" (2% NaOH, 70% diethylenetriamine, 28% ethylene glycol monomethyl ether). Mustard gas is also carcinogenic (cancer causing) and mutagenic (causing damage to DNA of exposed cells). PVP (polyvinyl pyrrolidone, povidone, polyvidone) is made from the monomer n-vinyl pyrrolidone: The monomer is carcinogenic and is extremely toxic to aquatic life. ... General Name, Symbol, Number iodine, I, 53 Chemical series halogens Group, Period, Block 17, 5, p Appearance violet-dark gray, lustrous Atomic mass 126. ... The most fundamental reactions in chemistry are the redox processes. ... In pathology, a carcinogen is any substance or agent that promotes cancer. ... In biology, a mutagen (Latin, literally origin of change) is an agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ...


History

After a failed attempt on the Eastern front, it was first used effectively in World War I by the German army against Canadian soldiers in 1917 and later also against the French – the name Yperite comes from its usage by the German army near the city of Ypres. It took the British over a year to develop their own mustard gas weapon, first using it in September 1918 during the breaking of the Hindenburg Line. A poison gas attack in World War I. The use of poison gas was a major military innovation of the First World War. ... The Bellfry of Ypres Ypres (French, generally used in English;1 Ieper official name in the local Dutch) is a municipality located in Flanders, one of the three regions of Belgium, and in the Flemish province of West Flanders. ... 1918 (MCMXVIII) was a common year starting on Tuesday of the Gregorian calendar (see link for calendar) or a common year starting on Wednesday of the Julian calendar. ... The Hindenburg Line was a vast system of defences in Northern France constructed by the Germans during the winter of 1916– 17 during World War I; the Germans called it the Siegfried Line. ...


Mustard gas was dispersed as an aerosol in a mixture with other chemicals, giving it a yellow-brown colour and a distinctive odour. Mustard gas was lethal in only about 1% of cases. Its effectiveness was as an incapacitating agent: a wounded soldier slows an advancing army much more than a dead one. The countermeasures against the gas were quite ineffective, since a soldier wearing a gas mask was not protected against absorbing it through the skin. Particulates, alternately referred to as Particulate Matter (PM), aerosols or fine particles are tiny particles of solid or liquid suspended in the air. ... A gas mask, also known as a respirator, is a mask worn on the face to protect the body from airborne pollutants and toxic materials. ...


Furthermore, mustard gas was a persistent agent which would remain in the environment for days and continue to cause sickness. If mustard gas contaminated a soldier's clothing and equipment, then other soldiers he came into contact with would also be poisoned. Towards the end of the war it was even used in high concentrations as an area-denial weapon, which often forced soldiers to abandon heavily contaminated positions.


Since then, mustard gas has also been reportedly used by:

Also, in 1943 a US stockpile was bombed in Bari, Italy, accidentally exposing thousands of civilians and 628 friendly troops. It was noted by medical workers that the white cell counts of exposed soldiers were decreased, and mustard gas was investigated as a therapy for Hodgkin's lymphoma, a form of cancer. Study of the use of similar chemicals as agents for the treatment of cancers led to the discovery of mustine, and the birth of anticancer chemotherapy. Leaders of the Bolshevik Party and the Communist International, a painting by Malcolm McAllister on the Pathfinder Mural in New York City and on the cover of the book Lenin’s Final Fight published by Pathfinder. ... 1919 (MCMXIX) was a common year starting on Wednesday (see link for calendar). ... 1920 (MCMXX) is a leap year starting on Thursday (link will take you to calendar) // Events January January 7 - Forces of Russian White admiral Kolchak surrender in Krasnoyarsk. ... 1923 (MCMXXIII) was a common year starting on Monday (link will take you to calendar). ... 1926 (MCMXXVI) was a common year starting on Friday (link will take you to calendar). ... 1930 (MCMXXX) is a common year starting on Wednesday. ... á 1935 (MCMXXXV) was a common year starting on Tuesday (link will take you to calendar). ... 1940 (MCMXL) was a leap year starting on Monday (link will take you to calendar). ... 1937 (MCMXXXVII) was a common year starting on Friday (link will take you to calendar). ... 1945 (MCMXLV) was a common year starting on Monday (link will take you to calendar). ... The Yemen Arab Republic, also known as North Yemen, was a country in the northern part of what is now Yemen. ... 1963 (MCMLXIII) was a common year starting on Tuesday (link will take you to calendar). ... 1967 (MCMLXVII) was a common year starting on Sunday of the Gregorian calendar. ... 1983 (MCMLXXXIII) is a common year starting on Saturday of the Gregorian calendar. ... 1988 (MCMLXXXVIII) is a leap year starting on a Friday of the Gregorian calendar. ... Kurds are one of the Iranian peoples and speak Kurdish, a north-Western Iranian language related to Persian. ... 1988 (MCMLXXXVIII) is a leap year starting on a Friday of the Gregorian calendar. ... 1943 (MCMXLIII) is a common year starting on Friday. ... Wikiquote has a collection of quotations by or about: United States Wikinews has news related to this article: United States United States government CIA World Factbook Entry for United States House. ... Region Apulia Mayor Michele Emiliano Area  116 km² Population  - City (2004)  - Density 316. ... Hodgkins lymphoma, formerly known as Hodgkins disease, is a type of lymphoma described by Thomas Hodgkin in 1832, and characterized by the presence of Reed-Sternberg cells. ... Mustine is the prototype anticancer chemotherapeutic drug. ...


Disposal of Mustard Gas

Most of the mustard gas found in Germany after World War II was dumped into the Baltic Sea. When mustard gas is exposed to seawater, it forms a tar-like gel and maintains its lethality for at least five years. It is possible to mistake a piece of polymerised mustard gas for amber, which can lead to severe health problems. Shells containing mustard gas and other toxic ammunition from World War I (as well as conventional explosives) can still occasionally be found in France and Belgium; they used to be disposed of by explosion at sea, but current environmental regulations prohibit this and so the French government is building an automated factory to dispose of the backlog of shells. World War II was a truly global conflict with many facets: immense human suffering, fierce indoctrination, and the use of new, extremely devastating weapons such as the atom bomb. ... The Baltic Sea is located in Northern Europe, from 53 deg. ... Polymerization is a process of reacting monomer molecules together in a chemical reaction to form linear chains or a three-dimensional network of polymer chains [1]. There are many forms of polymerization and different systems exist to categorize them. ... Amber pendants. ... A shell is a projectile, which, as opposed to a bullet, is not solid but contains an explosive or other filling, though modern usage includes large projectiles without a filling. ... World War I was primarily a European conflict with many facets: immense human sacrifice, stalemate trench warfare, and the use of new, devastating weapons - tanks, aircraft, machine guns, and poison gas. ...


In 1972, The United States Congress banned the practice of disposing chemical weapons into the ocean. However by this point, 64 million pounds of nerve and mustard agents had already been dumped into the ocean waters off of the United States by the U.S. Army. According to a 1998 report created by William Brankowitz, a deputy project manager in the U.S. Army Chemical Materials Agency, the Army created at least 26 chemical weapons dumpsites in the ocean off of at least 11 states on both the west and east coasts. Additionally due to poor records, they currently only know the rough whereabouts of half of them.


A significant portion of the stockpile of mustard agent in the United States was stored at the Edgewood Area of Aberdeen Proving Ground in Maryland. Approximately 1621 tons of mustard agent was stored in one-ton (900 kg) containers on the base under heavy guard. A disposal plant built on site neutralized the last of this stockpile in February, 2005. This stockpile had priority due to the potential for quick reduction of risk to the community. The closest schools were fitted with overpressurization units to protect the students and staff 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 US Army and Federal Emergency Management Agency program (http://www.fema.gov/preparedness/csepp.shtm). Unexploded shells containing mustard agent and other chemical agents are still present in several test ranges in proximity to Edgewood area schools, but the smaller amounts (4–14 pounds; 2–6 kg) present considerably less risk. They are being systematically detected and excavated for disposal. There are several other sites in the United States where the remaining US stockpiles of chemical agents are awaiting destruction in compliance with international chemical weapons treaties; the largest mustard agent stockpile, approximately 6196 tons, is stored at the Deseret Chemical Depot in Utah with destruction anticipated to begin in 2006. US mustard agent and other chemical agent storage is managed by the US Army's Chemical Materials Agency (http://www.cma.army.mil/home.aspx). The Chemical Materials Agency (CMA) manages disposal operations at five of the remaining seven stockpile sites, located in Alabama, Arkansas, Indiana, Utah, and Oregon; disposal projects at the other two sites, located in Kentucky and Colorado, are managed by the Program Manager Assembled Chemical Weapons Alternatives (ACWA) (http://www.pmacwa.army.mil/).


External links

  • Textbook of Military Medicine - Intensive overview of mustard gas Includes many references to scientific literature
  • An overview of the sulfur and nitrogen mustard agents (Caution: contains graphic images)
  • Bristol University - Basic Chemical Overview
This reference has several errors in it:
  1. The Fredrick Guthrie synthesis should be from ethylene and SCl2, not ethylene and Cl2 as stated.
  2. The hydrolysis reaction pathway produces two molecules of HCl and the last one produced is H2O, not three molecules of HCl as shown in the reference.
  3. The molecular structure given for nitrogen mustard (N-mustard) is not correct. The nitrogen atom should have a hydrogen bonded to it.
This reference also has an error in it: in the sentence on synthesis of mustard gas, the phrase "sulfur monochloride, S2Cl2" should be "sulfur dichloride, SCl2"
  • Questions and Answers for Mustard Gas
  • Organization for the Prohibition of Chemical Weapons - Mustard Agents


Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ...

This article forms part of the series
Blood agents: Cyanogen chloride (CK) – Hydrogen cyanide (AC)
Blister agents: Lewisite (L) – Sulfur mustard gas (HD, H, HT, HL, HQ) – Nitrogen mustard gas (HN1, HN2, HN3)
Nerve agents: G-Agents: Tabun (GA) – Sarin (GB) – Soman (GD) – Cyclosarin (GF) | V-Agents: VEVGVMVX
Pulmonary agents: ChlorineChloropicrin (PS) – Phosgene (DP) – Diphosgene (CG)
Incapacitating agents: Agent 15 (BZ) – KOLOKOL-1
Riot control agents: Pepper spray (OC) – CS gasCN gasCR gas .

  Results from FactBites:
 
AllRefer.com - mustard gas (Organic Chemistry) - Encyclopedia (291 words)
mustard gas, chemical compound used as a poison gas in World War I. The burning sensation it causes on contact with the skin is similar to that caused by oil from fl mustard seeds.
Mustard gas was introduced by the Germans in warfare against the British at Ypres, Belgium, in July, 1917, and took a heavy toll of casualties.
It is dispersed as an aerosol by a bursting shell.
First World War.com - Weapons of War - Poison Gas (1737 words)
Raising Special Gas Companies in the wake of the Germans' April attack (of approximately 1,400 men) operating under the command of Lieutenant-Colonel Charles Foulkes, instructions were given to prepare for a gas attack at Loos in September 1915.
Mustard gas, an almost odourless chemical, was distinguished by the serious blisters it caused both internally and externally, brought on several hours after exposure.
Gas never turned out to be the weapon that turned the tide of the war, as was often predicted.
  More results at FactBites »

 
 

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