Cyclosarin

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Cyclosarin
Cyclosarin.svg
Cyclosarin-3D-balls.png
Names
Preferred IUPAC name
Cyclohexyl methylphosphonofluoridate
Other names
GF;(Fluoro-methyl-phosphoryl)oxycyclohexane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
UN number 2810
  • InChI=1S/C7H14FO2P/c1-11(8,9)10-7-5-3-2-4-6-7/h7H,2-6H2,1H3 Yes check.svgY
    Key: SNTRKUOVAPUGAY-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H14FO2P/c1-11(8,9)10-7-5-3-2-4-6-7/h7H,2-6H2,1H3
    Key: SNTRKUOVAPUGAY-UHFFFAOYAC
  • O=P(F)(OC1CCCCC1)C
Properties
C7H14FO2P
Molar mass 180.159 g·mol−1
AppearanceColorless liquid
Density 1.1278 g/cm3
Melting point −30 °C (−22 °F; 243 K)
Boiling point 239 °C (462 °F; 512 K)
Almost insoluble
Hazards
Flash point 94 °C (201 °F; 367 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclosarin or GF (cyclohexyl methylphosphonofluoridate) is an extremely toxic substance used as a chemical weapon. [1] It is a member of the G-series family of nerve agents, a group of chemical weapons discovered and synthesized by a German team led by Gerhard Schrader. The major nerve gases are the G agents, sarin (GB), soman (GD), tabun (GA), and the V agents such as VX. The original agent, tabun, was discovered in Germany in 1936 in the process of work on organophosphorus insecticides. Next came sarin, soman and finally, cyclosarin, a product of commercial insecticide laboratories prior to World War II.

Contents

As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations. Pursuant to UN Resolution 687 its production and stockpiling was outlawed globally by the Chemical Weapons Convention (CWC) of 1993, although Egypt, Israel, North Korea and South Sudan have not ratified the CWC (thus not outlawing their own stockpiling of chemical weapons).

Chemical characteristics

Like its predecessor sarin, cyclosarin is a liquid organophosphate nerve agent. Its physical characteristics are, however, quite different from those of sarin.

At room temperature, cyclosarin is a colorless liquid whose odor has been variously described as sweet and musty, [2] or resembling peaches or shellac. Unlike sarin, cyclosarin is a persistent liquid, meaning that it has a low vapor pressure and therefore evaporates relatively slowly, at only about 1/69th the rate of sarin and 1/20th that of water.

Also unlike sarin, cyclosarin is flammable, with a flash point of 94 °C (201 °F).

History

First synthesized during World War II as part of Nazi Germany's chemical weapons research on organophosphate compounds after their military potential was recognized, cyclosarin was also studied later in the United States and Great Britain in the early 1950s as part of a systematic study of potential nerve agents. It was never selected for mass production, however, due to its precursors being more expensive than those of other G-series nerve agents such as sarin (GB).

To date, Iraq is the only nation known to have manufactured significant quantities of cyclosarin for use as a chemical agent and to deploy it in battle. During the Iran–Iraq War (1980–1988), the Iraqis used sarin and cyclosarin together as a mixture. This was likely done to obtain a more persistent chemical agent as well as in response to an existing embargo placed on alcohol precursors for sarin. [3]

Munitions

Binary weapons

Like other nerve agents, cyclosarin can be shipped in binary munitions.

A cyclosarin binary weapon would most likely contain methylphosphonyl difluoride in one capsule, with the other capsule containing a mixture of cyclohexylamine and cyclohexanol.

GB-GF mixtures

Iraq fielded munitions filled with a mixture of GB (sarin) and GF (cyclosarin). Tests on mice indicated that GB-GF mixtures have a relative toxicity between GF and GB. [4]

Related Research Articles

Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase (AChE), an enzyme that catalyzes the breakdown of acetylcholine, a neurotransmitter. Nerve agents are irreversible acetylcholinesterase inhibitors used as poison.

<span class="mw-page-title-main">Chemical warfare</span> Using poison gas or other toxins in war

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 for chemical, biological, radiological, and nuclear, all of which are considered "weapons of mass destruction" (WMDs), a term that contrasts with conventional weapons.

<span class="mw-page-title-main">Sarin</span> Chemical compound and chemical warfare nerve agent

Sarin is an extremely toxic organophosphorus compound. A colourless, odourless liquid, it is used as a chemical weapon due to its extreme potency as a nerve agent. Exposure can be lethal even at very low concentrations, where death can occur within one to ten minutes after direct inhalation of a lethal dose, due to suffocation from respiratory paralysis, unless antidotes are quickly administered. People who absorb a non-lethal dose and do not receive immediate medical treatment may suffer permanent neurological damage.

<span class="mw-page-title-main">Tabun (nerve agent)</span> Chemical compound

Tabun or GA is an extremely toxic synthetic organophosphorus compound. It is a clear, colorless, and tasteless liquid with a faint fruity odor. It is classified as a nerve agent because it can fatally interfere with normal functioning of the mammalian nervous system. Its production is strictly controlled and stockpiling outlawed by the Chemical Weapons Convention of 1993. Tabun is the first of the G-series nerve agents along with GB (sarin), GD (soman) and GF (cyclosarin).

<span class="mw-page-title-main">Soman</span> Chemical compound (nerve agent)

Soman is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiting the enzyme cholinesterase. It is an inhibitor of both acetylcholinesterase and butyrylcholinesterase. As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations according to UN Resolution 687. Its production is strictly controlled, and stockpiling is outlawed by the Chemical Weapons Convention of 1993 where it is classified as a Schedule 1 substance. Soman was the third of the so-called G-series nerve agents to be discovered along with GA (tabun), GB (sarin), and GF (cyclosarin).

<span class="mw-page-title-main">VX (nerve agent)</span> Chemical compound and chemical warfare nerve agent

VX is an extremely toxic synthetic chemical compound in the organophosphorus class, specifically, a thiophosphonate. In the class of nerve agents, it was developed for military use in chemical warfare after translation of earlier discoveries of organophosphate toxicity in pesticide research. In its pure form, VX is an oily, relatively non-volatile liquid that is amber-like in colour. Because of its low volatility, VX persists in environments where it is dispersed.

Binary chemical weapons or munitions are chemical weapons which contain the toxic agent in its active state as chemical precursors that are significantly less toxic than the agent. This improves the safety of storing, transporting, and disposing of the weapon. Commonly, firing the munition removes a barrier between two precursors. These react to form the intended agent which is then aerosolized and distributed by a bursting charge.

<span class="mw-page-title-main">Chlorosarin</span> Chemical compound

Chlorosarin is a chemical precursor used in the final step of one method for the production of the nerve agent sarin. Also known as O-isopropyl methylphosphonochloridate and isopropyl methylphosphonic chloride, it has a molecular weight of 156.55 g/mol and a molecular formula of C4H10ClO2P.

<span class="mw-page-title-main">VG (nerve agent)</span> Chemical compound

VG is a "V-series" nerve agent chemically similar to the better-known VX nerve agent. Tetram is the common Russian name for the substance. Amiton was the trade name for the substance when it was marketed as an insecticide by ICI in the mid-1950s.

Gerhard Schrader was a German chemist specializing in the discovery of new insecticides, hoping to make progress in the fight against hunger in the world. Schrader is best known for his accidental discovery of nerve agents including sarin and tabun. Sarin is partially named after him: It was named in honor of its discoverers, Schrader, Otto Ambros, Gerhard Ritter, and Hans-Jürgen von der Linde.

<span class="mw-page-title-main">Chemical weapon proliferation</span> Prevalence and spread of chemical weapons

Many nations continue to research and/or stockpile chemical weapon agents despite numerous efforts to reduce or eliminate them. Most states have joined the Chemical Weapons Convention (CWC), which required the destruction of all chemical weapons by 2012. Twelve nations have declared chemical weapons production facilities and six nations have declared stockpiles of chemical weapons. All of the declared production facilities have been destroyed or converted for civilian use after the treaty went into force.

<span class="mw-page-title-main">Germany and weapons of mass destruction</span>

Although Germany has the technical capability to produce weapons of mass destruction (WMD), since World War II it has refrained from producing those weapons. However, Germany participates in the NATO nuclear weapons sharing arrangements and trains for delivering United States nuclear weapons. Officially, 20 US-nuclear weapons are stationed in Büchel, Germany. It could be more or fewer, but the exact number of the weapons is a state secret.

Chemical, biological (CB) — and sometimes radiological — warfare agents were assigned what is termed a military symbol by the U.S. military until the American chemical and biological weapons programs were terminated. Military symbols applied to the CB agent fill, and not to the entire weapon. A chemical or biological weapon designation would be, for example, "Aero-14/B", which could be filled with GB, VX, TGB, or with a biological modification kit – OU, NU, UL, etc. A CB weapon is an integrated device of (1) agent, (2) dissemination means, and (3) delivery system.

<span class="mw-page-title-main">Iraqi chemical weapons program</span> Offensively and genocidally used chemical weapons

In violation of the Geneva Protocol of 1925, the Iraqi Army initiated two failed and one successful (1978–1991) offensive chemical weapons (CW) programs. President Saddam Hussein (1937–2006) pursued the most extensive chemical program during the Iran–Iraq War (1980–1988), when he waged chemical warfare against his foe. He also used chemicals in 1988 in the Al-Anfal Campaign against his civilian Kurdish population and during a popular uprising in the south in 1991.

Methylphosphonyl difluoride (DF), also known as EA-1251 or difluoro, is a chemical weapon precursor. Its chemical formula is CH3POF2. It is a Schedule 1 substance under the Chemical Weapons Convention. It is used for production of sarin and soman as a component of binary chemical weapons; an example is the M687 artillery shell, where it is used together with a mixture of isopropyl alcohol and isopropyl amine, producing sarin.

<span class="mw-page-title-main">M55 (rocket)</span> American chemical weapon

The M55 rocket was a chemical weapon developed by the United States in the 1950s. The United States Army produced both Sarin and VX unitary warheads for the M55.

<span class="mw-page-title-main">Chemical weapon</span> Device that uses chemicals to kill or harm individuals

A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a weapon "or its precursor that can cause death, injury, temporary incapacitation or sensory irritation through its chemical action. Munitions or other delivery devices designed to deliver chemical weapons, whether filled or unfilled, are also considered weapons themselves."

The United States chemical weapons program began in 1917 during World War I with the creation of the U.S. Army's Gas Service Section and ended 73 years later in 1990 with the country's practical adoption of the Chemical Weapons Convention. Destruction of stockpiled chemical weapons began in 1986 and was completed on July 7, 2023. The U.S. Army Medical Research Institute of Chemical Defense (USAMRICD), at Aberdeen Proving Ground, Maryland, continues to operate.

<span class="mw-page-title-main">Muthana State Establishment</span>

Muthana State Establishment or Muthanna (Arabic: منشأة المثنى العامة) (also known for its code-name Project 922 and cover name State Enterprise for Pesticide Production (SEPP)) was Iraq's main chemical weapons research, development, and production facility. It is located in Saladin Governorate 40 km south west of Samarra, 140 km north west of Baghdad. This mega facility covering an area 100 km², contained three main production areas.

References

  1. Ellison, D. Hank (2008), Handbook of Chemical and Biological Warfare Agents (Second ed.), CRC Press, pp 20-21. ISBN   978-0-849-31434-6
  2. Ledgard J. A laboratory history of chemical warfare agents (2nd, 2006). pp 197-202. ISBN   978-0-6151-3645-5
  3. "Nerve Agent:GF". Archived from the original on January 8, 2009. Retrieved January 5, 2009.
  4. "CBWInfo.com". Archived from the original on January 8, 2009. Retrieved March 1, 2012.