Dimethyl methylphosphonate

Dimethyl methylphosphonate

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Dimethyl methylphosphonate, or methylphosphonic acid dimethyl ester (DMMP), is a colorless liquid with chemical formula 393 or CH3PO(OCH3)2. It is combustible. It emits a distinct odor. It can be found in household radiators, especially those installed in the former Soviet Bloc. In contact with water it slowly undergoes hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

. May soften some plastic
Plastic
A plastic material is any of a wide range of synthetic or semi-synthetic organic solids used in the manufacture of industrial products. Plastics are typically polymers of high molecular mass, and may contain other substances to improve performance and/or reduce production costs...

s and rubber
Rubber
Natural rubber, also called India rubber or caoutchouc, is an elastomer that was originally derived from latex, a milky colloid produced by some plants. The plants would be ‘tapped’, that is, an incision made into the bark of the tree and the sticky, milk colored latex sap collected and refined...

s.
Its other names are dimethoxymethyl phosphine oxide, dimethyl methanephosphonate, dimethyl methyl phosphonate, Fran TF 2000, Fyron DMMP, Metaran, NSC 62240, O,O-dimethyl methylphosphonate, and Reoflam DMMP.

The primary commercial use of dimethyl methylphosphonate is as a flame retardant
Flame retardant
Flame retardants are chemicals used in thermoplastics, thermosets, textiles and coatings that inhibit or resist the spread of fire. These can be separated into several different classes of chemicals:...

. Other commercial uses are a preignition additive for gasoline
Gasoline
Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...

, anti-foaming agent, plasticizer
Plasticizer
Plasticizers or dispersants are additives that increase the plasticity or fluidity of the material to which they are added; these include plastics, cement, concrete, wallboard, and clay. Although the same compounds are often used for both plastics and concretes the desired effects and results are...

, stabilizer
Stabilizer (chemistry)
In chemistry a stabilizer is a chemical which tends to inhibit the reaction between two or more other chemicals. It can be thought of as the antonym to a catalyst...

, textile conditioner, antistatic agent
Antistatic agent
An antistatic agent is a compound used for treatment of materials or their surfaces in order to reduce or eliminate buildup of static electricity generally caused by the triboelectric effect. Its role is to make the surface or the material itself slightly conductive, either by being conductive...

, and an additive for solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

s and low-temperature hydraulic fluid
Hydraulic fluid
Hydraulic fluids, also called hydraulic liquids, are the medium by which power is transferred in hydraulic machinery. Common hydraulic fluids are based on mineral oil or water...

s. It can be used as a catalyst and a reagent in organic synthesis, as it can generate a highly reactive ylide
Ylide
An ylide or ylid is a neutral dipolar molecule containing a formally negatively charged atom directly attached to a hetero atom with a formal positive charge , and in which both atoms have full octets of electrons. Ylides are thus 1,2-dipolar compounds...

. The yearly production in the United States varies between 100 and 1000 ST (90,718.5 and 907,184.7 kg).

Dimethyl methylphosphonate is not classified as toxic, but is harmful if inhaled, swallowed or absorbed through the skin; it is a Chemical Weapons Convention
Chemical Weapons Convention
The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and use of chemical weapons. Its full name is the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction...

 schedule 2 chemical used in the synthesis
Chemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...

 of sarin
Sarin
Sarin, or GB, is an organophosphorus compound with the formula [2CHO]CH3PF. It is a colorless, odorless liquid, which is used as a chemical weapon. It has been classified as a weapon of mass destruction in UN Resolution 687...

 nerve gas. It can also be used as standalone as a simulant for sarin training exercises and for calibration of detectors. It is a suspected carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...

.

About 190 liters of dimethyl methylphosphonate, together with other chemicals, were released during the El Al Flight 1862
El Al Flight 1862
On 4 October 1992, El Al Flight 1862, a Boeing 747 cargo plane of the Israeli airline El Al, crashed into the Groeneveen and Klein-Kruitberg flats in the Bijlmermeer neighbourhood of Amsterdam, the Netherlands. For the location in the Bijlmermeer, the crash is known in Dutch as the "Bijlmerramp"...

crash at Bijlmer, Amsterdam.

See also