Chemical Name: S-2-(Diisopropylamino)Wthyl O-Ethyl Methylphosphonothioate

Chemical Name: S-2-(Diisopropylamino)Wthyl O-Ethyl Methylphosphonothioate

VX:

Vital precursors: phosphates (methylphosphites are particularly well-controlled), phosphorous chlorides, and alkyldiethanolamines

Chemical name: S-2-(diisopropylamino)wthyl O-ethyl methylphosphonothioate

SELECTED PRECURSORS

  1. Diethyl methylphosphonite (used in organic synthesis; schedule 3)
  2. Diisopropylamine (production exceeding 1 million pounds annually in the U.S; catalyst for polymerization.Anti-eroding lubricant agent and emulsifying agent. Intermediate for pharmaceuticals, coating materials, pesticide, agricultural chemicals, dyes, rubber chemicals, fiber, Alkylalkanolamines and other organic products. Additive in petroleum industry. solvent for hydrocarbon extraction; sold in iron drums)
  3. Diisopropylaminoethyl chloride (schedule 2B; Listof Chinese Suppliers: Bulk-Chem Inc, Shanghai CEC Chemical Co., Ltd, Jinan Yudong Tech-Development Co., Ltd; Interaction of potassium 1-phenylcyclopentanecarboxylate and 2-diethylaminoethyl chloride in absolute ethanol proved the most satisfactory of four methods examined for the preparation of 2-diethylaminoethyl 1-phenylcyclopentanecarboxylate hydrochloride (Parpanit). This procedure was used to obtain 2-(ethyl-2′-fluoroethylamino) ethyl (I), 2-(ethylisopropylamino) ethyl (II), 2-diisopropylaminoethyl (III), 2-pyrrolidinoethyl (IV), and 2-piperidinoethyl (V) 1-phenylcyclopentanecarboxylate hydrochlorides;Cationic starches are recognized as the choice for wet end additives due to their substantivity with cellulose fibers. The cationization of starches is accomplished by reaction with various tertiary and quaternary amine reagents. In general, a reactive chloride or epoxy group on one end of the reagent reacts with a starch hydroxyl group. The cationic portion of the amine then ionizes in the presence of water to form the positively charged derivative which is substantive to fiber. Quaternary ammonium derivatives are most commonly used in the paper. Other ionic charged starches are produced by reaction of starch with amino, imino, ammonium, sulfonium, or phosphonium groups, all of which carry an ionic charge. The key factor in their usefulness is their affinity for negatively charged substrates such as cellulose. These ionic starches have found widespread use in the paper industry as wet end additives, surface sizing agents and coating binders. Cationic starches improve sheet strength by promoting ionic bonding and additional hydrogen bonding within the cellulose fibers. Some common reagents used to prepare cationic starches include: 2-diethylaminoethyl chloride (DEC); 2-dimethylaminoethyl chloride; 2-diisopropylaminoethyl chloride; 2-diethylaminoethyl bromide; 2-dimethylaminoisopropyl chloride; N-alkyl-N-(2-haloethyl)-aminomethylphosphonic acids; and 2,3-epoxypropyltrimethylammonium chloride.
  4. O-Ethyl O-2-diisopropylaminoethyl methylphosphonite (code designation QL) (schedule 1; no industrial applications)
  5. O-Ethyl methylphosphonothioic acid (also known as EMPTA) (dual-use; schedule 2B)
  6. Ethyl hydrogen methylphosphonite (schedule 2B; Upon addition of up to one mole of water per mole of diethyl methylphosphonite, ethyl hydrogen methylphosphinate was produced in a very rapid and complete reaction. Upon addition of greater than one mole of water—up to two moles of water per mole of diethyl methylphosphinate—the ethyl hydrogen methylphosphonite that was produced was further hydrolyzed to dihydrogen methylphosphinate in a very slow reaction)
  7. Methylphosphonous dichloride (also known as SW) (dual-use; schedule 2B)
  8. Methylphosphonous difluoride (used in sarin- see below)
  9. Methylphosphonothioic dichloride (also known as SWS) (The phosphorus pentasulphide which Iraq had imported into its VX programme had been used as a source, not of phosphorus, but of sulphur in making methylphosphonothioic dichloride, this then being reacted with the precursor which Iraqi workers called "choline", in fact 2-N,N- diisopropylaminoethanol. In a variant production process being studied late in the programme, the end-product was VX hydrochloride, known as "VX syrup", a molasses-like liquid, stable in storage, from which VX could readily be generated when needed; dual-use; schedule 2B)
  10. Phosphorus pentasulfide (Phosphorus pentasulfide can be used to introduce a phosphorus bonded to a sulfur into an organic compound, such as V-type nerve agents including VX. The most significant commercial use of phosphorus pentasulfide is in the manufacture of zinc dialkyldithiophosphates additives for high performance lubricants. It is also used in the manufacture of insecticides including chlorpyrifos and in the manufacture of thiophosphates used in mining for ore flotation; Like another nerve agent precursor, phosphorus trichloride, it is prepared by the reaction of two elements: molten sulfur and molten phosphorus. Annual production and consumption in the US is about 50,000 tons per year
  11. Phosphorus trichloride (used in sarin- see below)
  12. Sulfur (Used in matches, gunpowder, medicines; obtained naturally and easily purchased)

#s 11, 7, 9, and 5 can be used in sequence to produce VX- Iraq is the only country known to have used #5 for VX; the US uses #4 for its synthesis

Soman:

CHEMICAL NAME: Phosphonofluoridic acid, methyl-, 1, 2, 2-trimethylpropyl ester

ALTERNATE CHEMICAL NAMES:

  • Pinacolyl methylphosphonofluoridate
  • 1,2,2-Trimethylpropyl methylphosphonofluoridate
  • Methylpinacolyloxyfluorophosphine oxide
  • Pinacolyloxymethylphosphonyl flouride
  • Pinacolyl methanefluorophosphonate
  • Methylfluoropinacolylphosphonate
  • Fluoromethylpinacolyloxyphosphine Oxide
  • Methylpinacolyloxyphosphonyl flouride
  • Pinacolyl methylfluorophosphonate
  • 1,2,2,-Trimethylpropoxyfluoromethylphosphine oxide

SELECTED PRECURSORS

  • Ammonium bifluoride (used in sarin- see below)
  • Dimethyl methylphosphonate (used in sarin- see below)
  • Diethylphosphite (used in sarin- see below)
  • Dimethylphosphite (used in sarin- see below)
  • Hydrogen fluoride (used in sarin- see below)
  • Methylphosphonous difluoride (used in sarin- see below)
  • Methylphosphonyl dichloride (used in sarin- see below)
  • Methylphosphonyl difluoride (used in sarin- see below)
  • Pinacolone (clear liquid w/ mint or camphor odor; molecular formula is C[6]H[12]O; primary use is in the synthesis of triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin and pesticides paclobutrazole and uniconazole. It is also the immediate precursor for pinacolyl alcohol and is the more important of the 2 in industrial chemistry; Pinacolone can be made by several routes. The simplest, or at least the one using the most unobtrusive starting materials, is by a well-characterized reaction known as the pinacol rearrangement. This involves acetone as the only reactant in the presence of an acid catalyst. Acetone is a high production volume chemical with worldwide annual production of 1 million tons. Other routes use more exotic starting materials that would be more telling indicators of their intent. The other significant commercial route is by the reaction of tert-butanol and formaldehyde; shipped in 160kg iron drums by Zhangjiagang (Bonded Area) East Agrochemical International Trade Co., Ltd., for example of procurement)
  • Pinacolyl alcohol (clear liquid w/ alcohol odor; molecular formula is C[6]H[14]O; immediate synthesis is by the reduction of pinacolone or made by Aldrich Chemical Co.)
  • Potassium bifluoride (used in sarin- see below)
  • Potassium fluoride (used in sarin- see below)
  • Phosphorus trichloride (used in sarin- see below)
  • Sodium bifluorideSodium fluoride (used in sarin- see below)
  • Thionyl chloride (used in sarin- see below)
  • Trimethyl phosphite (used in sarin- see below)

Methylphosphonyldifluoride and pinacolyl alcohol combine with an amine for the binary

Sarin:

Chemical Name: O-Isopropyl methylphosphonofluoridate

Phosphorous trichloride, Methyl iodide, Acetonitrile (dilutor to improve stability) mixed in Tokyo

Dimethyl methylphosphonate, hydrogen fluoride, isopropyl alchohol

Methylphosphonyldifluoride and isopropanol (sometimes mixed w/ isopropylamine) make up the US binary

Methylphosphonyldichloride, Methylphosphonyldifluoride, and isopropyl alcohol mixed in final process

Key precursors: methylphosphonyl difluoride; methylphosphonyl dichloride; diisopropyl methylphosphonochloridate

Precursors: Dimethyl methylphosphonate; isopropyl methylphosphonate

Other chemicals: Trimethylphosphite; phosphorus trichloride; triisopropyl phosphate

SELECTED PRECURSORS

  • Ammonium bifluoride(an ammonium bifluoride solution is what you would get if you started with a solution of hydrofluoric acid and added enough ammonium hydroxide to neutralize one half of the acid present; used in glass products such as glass etching pastes (incl. B & B Products’ Etchall) and Wheel cleaners (like Quicksilver by Armor All)
  • Dimethyl methylphosphonate (DMMP is widely used as a flame retardant and this is its primary commercial use. It can also be used as a catalyst and as a reagent in organic synthesis because it can be used to generate a highly reactive and very useful ylide reagent; It is used in the manufacture of the nerve gas sarin using the US "di-di" process, but in a manner distinct from ylide chemistry. It can also be used as a simulant for Sarin training exercises and in the calibration of detectors
  • Diethylphosphite (Diethylphosphite is an important organic chemical compound raw material; manufacture by adopting continuous craft to synthesize and depickle then obtain the finished product by rectifying; The product can used as extracting agent, phosphoric acid ester family intermediate; widely used in pesticide industry for producing organophosphorus fungicide--kitazin. The product can take place of the mercurial to prevent and cure rice blast. Also has certain effect on rice rhizoctonia disease and grain dry sickness ,etc; Diethylphosphite (DEP) can be used as a thermally latent curing agent for epoxy resins by means of the formation of phosphonic acid active groups through the de-ethanol reaction of DEP. The mechanism and activation energy of the curing reaction and the thermally latent characteristics of DEP on curing epoxy resins were demonstrated with 1H NMR, pyrolysis-GC/MS, and DSC measurements. The cured epoxy resins exhibited good thermal stability over 300 ¢J and improved flame retardance alone with the introduction of phosphorus element from DEP curing agent. Therefore, this commercial available DEP compound was potentially used as thermally latent curing agent and flame retardant for epoxy resins
  • Dimethylphosphite(Dimethyl phosphite (DMP) is mainly used to make glyphosate, one of the most important herbicide in China; There is no import of DMP in China and the export volume has been increasing and it will increase more rapidly in the next few years)
  • Hydrogen fluoride (Hydrogen fluoride is produced commercially by heating purified fluorspar (calcium fluoride) with concentrated sulfuric acid to produce the gas, which may be condensed by cooling or dissolved in water. Hydrogen fluoride is available commercially either in an anhydrous (water-free) state or in water solutions of various concentrations. Because it attacks glass, it is usually stored in steel tanks, cylinders, or drums, or, in small amounts, in plastic bottles; hydrogen fluoride is primarily an industrial raw material. It is produced commercially by action of sulfuric acid on the mineral fluorspar. Hydrogen fluoride is used in separating uranium isotopes, as a cracking catalyst in oil refineries, and for etching glass and enamel, removing rust, and cleaning brass and crystal. It also is used in manufacturing silicon semiconductor chips and as a laboratory reagent. Some consumer products that may contain hydrogen fluoride include automotive cleaning products (e.g., for aluminum and chrome), rust inhibitors, rust removers (e.g., for ceramic tubs, sinks, and fabrics), and water-spot removers.The following operations may involve hydrogen fluoride and lead to worker exposures to this substance:
  • * The manufacture and transportation of hydrogen fluoride
  • * Use in manufacture of chlorofluorohydrocarbons for application as refrigerant fluids, aerosol propellants, specialty solvents, high-performance plastics, and foaming agents
  • * Use (as aqueous acid) in cleaning sandstone and marble, as a pickling agent for stainless steel and other metals, and as a cleaner in the meat packing industry
  • * Use (as anhydrous acid) in manufacture of aluminum fluoride and synthetic cryolite to reduce aluminum oxide to aluminum
  • * Use (as aqueous acid) in electroplating operations
  • * Liberated during manufacture of fertilizer and the burning of coal
  • * Use (as anhydrous acid) as a catalyst in alkylation of petroleum fractions to produce high-octane fuels
  • * Use (as aqueous acid) in etching, frosting, and polishing of glassware and ceramics
  • * Use as an acidizing agent during injection of acid into oil wells
  • * Used (as aqueous acid) in removal of sand and scale from foundry castings
  • * Use (as anhydrous acid) in separation and purification of uranium isotopes
  • * Use (as aqueous acid) in treating textiles to remove trace metals and in preparation of microelectronic circuits and quartz crystals for radio oscillators
  • * Use (as anhydrous acid) in production of fluorosilicone products
  • * Use (as anhydrous acid) in manufacture of pharmaceuticals and special dyes
  • * Use to arrest fermentation in brewing and for etching silicon wafers in semi-conductor manufacture, for purification of filter paper and graphite, in enamelling and galvanizing iron, and to increase the porosity of ceramics
  • Methylphosphonous difluoride (Phosphonates are commercially produced for several diverse applications, includinq insecticides, surfactants, extractants of fissionable elements, and additives in industrial oils and polymers. Kosolapofflists a large number of general methods for their preparation. Amethod particularly attractive for commercial production, developed by Schrader, involves the synthesis of dimethyl hydrogen phosphate (DhlHP) by the reaction of PCl3 and methanol. After purification by distillation, DMHP is pyrolyzed to derivatives of methylphosphonic acid. These derivatives are generically referred to here as methylphosphonates, phosphonates, or MP.Alarge number of compounds are produced in the pyrolysis step, and the selectivity to phosphonates under typical conditions is only about 70%. Inexpensive procedures are not available for separating the by-products or for recovering the phosphorus for recycle. By-product phosphates are particularly undesirable. Then the pyrolysis product is treated with chlorine and PC13 to convert methylphosphonates to methylphosphonyl dichloride, phosphates are converted to POCl3, consuming excessive amounts of chlorine and PCl3
  • Methylphosphonyl dichloride (high risk precursor with moderate commercial use, so heavily export-controlled
  • Methylphosphonyl difluoride (seem to be few if any established industrial uses, so hard to find; the synthetic route to the mass manufacture of Sarin involved 5 steps. In the first step, phosphorus trichloride was reacted with methanol to produce trimethylphosphite. In the second step, trimethylphosphite was converted to imethylmethylphosphonate (DMMP) through a rearrangement caused by the application of heat. In the third step, DMMP was reacted with phosphorus pentachloride by applying heat, to produce methylphosphonyl dichloride. In the fourth step, methylphosphonyl dichloride was reacted with sodium fluoride to produce methylphosphonyl difluoride. In the final step, methylphosphonyl difluoride and methylphosphonyl dichloride were mixed with isopropyl alcohol to produce Sarin)
  • Potassium bifluoride(used for manufacturing wood preservatives, the production of soldering agents and brazing, as a catalyst for polymerization, as a component of electrolyte and fluorine production, in glass industry for etching and manufacturing special optical glasses; Bifluorides are used as a source of the fluorine atom in the synthesis of all of the G-type nerve agents except Tabun, in which the fluorine atom is replaced by a cyanide group. All bifluorides are synthesized from ammonium bifluoride. Ammonium bifluoride is in turn made from ammonium fluoride which is made by the reaction of ammonium hydroxide with hydrofluoric acid, ammonium fluoride is converted to the bifluoride by dehydrating an aqueous solution of ammonium fluoride. The other bifluorides are manufactured by essentially the same process, except that the water, and the more volatile ammonia, are driven off in the presence of a sodium or potassium compound)
  • Potassium fluoride (The primary uses of potassium fluoride are in the metallurgical industry, including soldering fluxes and in tin plating. It is also widely used as a fluorinating agent in organic synthesis to replace other halide atoms (chlorine, bromine, iodine) with fluorine. This includes the manufacture of a number of pesticides and insecticides It is also a useful catalyst in the manufacture of polyurethanes; used also in etching glass)
  • Phosphorus trichloride(prepared by the action of chlorine on white or red phosphorus on heating in a retort, and condensing the phosphorus trichloride vapour in a cooled dry receiver; used in organic chemistry as a chlorinating agent; 70% of US production is used in the manufacture of organophosphorus pesticides including glyphosate, the active component of Roundup. A further 12% is used in the manufacture of phosphorus oxychloride. Another 12% is used in surfactants and water processing chemicals and the remainder in plastic processing and in oil and plate additives)
  • Sodium bifluoride (Sodium Bifluoride is normally manufactured by the reaction of hydrofluoric acid and soda ash (sodium carbonate), or caustic soda (sodium hydroxide); uses are Cleaning of stone and brick surfaces, food processing equipment sanitation, commercial laundry Laundry souring, agent, tin plate production, zinc galvanizing; Sodium Bifluoride is used as a component of electrolyte for galvanizing baths. It is used in pest control and insectproofing agent for leather. It is used in textile industry for removal of iron rust and as a neutralization agent. It can be used as a catalyst for polymerization processing. It is used for sanitation and Laundry souring agent; order at LCIltd)
  • Sodium fluoride(chemical used in foundry fluxes, insecticides, enamels, glass mixes, electroplating, water fluoridation, dentrifice fluoride, and other applications; Nikkin Flux Corp., in Edwardsville, IL (near St. Louis, MO) is a distributor of sodium fluoride, with expertise in metals applications)
  • Thionyl chloride(Thionyl chloride is a versatile and effective chlorinating agent that can be used in a number of industrial chemical reactions. Despite the health hazards, thionyl chloride is easier to handle than other chlorinating agents and has the advantage of producing gaseous side products, which simplifies processing in industrial chemistry and also leads to high yields of products. The most important of these are the formation of the useful and highly reactive carboxylic acid chlorides, aromatic sulfochlorides and alkyl chlorides. Thionyl chloride also reacts with amines and sulfamic acids with the sulfamyl chloride reaction products from sulfamic acids being important intermediates in the synthesis of some herbicides. Thionyl chloride is also used as the electrolyte in high performance lithium-thionyl chloride batteries; Thionyl chloride is used in the "di-di" method of manufacturing G-type nerve agents. It is another precursor that can be made from very common or easily made precursors including chlorine and oxides of sulfur.It can also be made in reactions using one of two other listed precursors: sulfur monochloride or sulfur dichloride)
  • Trimethyl phosphite (Intermediate use in the manufacture of monocrotophos and other important organo-phosphorus insecticides. Also used in phosphorus-based flame retardants- United Phosphorus, Inc; prepared by hydrolysis of phosphorus trichloride (or tetraphosphorus hexaoxide) with alcohols or phenols. Phosphorous acid esters are called phosphite with the formula (RO)3P. Phosphorous acid and phosphite are used as reducing agents in chemical industry because of easy oxidation property to phosphoric acid. They are used as antioxidant, stabilizer and chelating agent in plastic system. They are used as solvent in paint and as flame retardant on fibres. They are used as a chemical intermediate in the production of pharmaceutical ingredients, pesticides, optical brighteners and in lubricant additives and adhesives)

Tabun: