Diethyl 2- ethylphosphonate

In the reaction described below triethyl phosphite (p. 308) is heated with ethyl iodide to give diethyl ethylphosphonate. Although theoretically a very small amount of ethyl iodide would suffice, it is advantageous to use more than the minimum amount so as to reduce the temperature of the boiling reaction-mixture. 

Diethyl Ethylphosphonate. A Hquid compound introduced for appHcations similar to those of DMMP is diethyl ethylphosphonate [78-38-6] CgH O P. This material is claimed to be less susceptible to undesirable interactions with haloaHphatic components, such as blowing agents, or with amine catalysts. 

Diethanol Sulfide Diethanolamine Diethanolethylamine Diethanolmethylamine Diethoxyethylphosphine Oxide Diethoxymethylphosphine Oxide Diethoxyphosphine Oxide Diethyene Disulfide Diethyl Acid Phosphate Diethyl Ethanephosphonate Diethyl Ethylphosphonate Diethyl Hydrogen Phosphate Diethyl Hydrogen Phosphite Diethyl Hydrogen Phosphonate Diethyl Isopropylphosphonate Diethyl Methanephosphonate Diethyl Methylphosphonate Diethyl Phosphate Diethyl Phosphite Diethyl Phosphonate Diethyl Phosphoric Acid Diethyl(2-hydroxyethyl)amine Diethyl(/S-hydroxyethyl)amine Diethylaminoethanol Diethylethanolamine Diethylfosfit... 

Diethyl ethylidenemalonate, 32, 54 Diethyl ethylphosphonate, 31, 34 Diethyl fumarate, 30, 46 Diethyl heptanoylsuccinate, 34, 51 Diethyl j-hexahydrophthalate,... 

Diethyl methylphosphonate may be prepared similarly by refluxing one molar equivalent of triethyl phosphite with one mole of methyl iodide, but it is very difficult to separate the product from the small amount of diethyl ethylphosphonate that is formed simultaneously by the interaction of the phosphite with the ethyl iodide liberated in the reaction. The pure substance boils at 51°/1 mm., no 1.4117, dl5 1.050. 

Octahedral and tetrahedral solvates (A1S )(C104)3 [n = 4,6 S = trimethyl phosphate (TMPA), hexamethylphosphorotriamide (HMPT), triethyl phosphate (TEPA), dimethyl methylphosphonate (DMMP), diethyl ethylphosphonate (DEEP), and dimethyl hydrogen phosphite (DMHP)] are shown by Al NMR to have tetrahedral and octahedral structures which are retained in nitromethane solution. 

Agawa, T., Kubo, T., and Ohshiro, Y, Synthesis of dialkyl epoxyphosphonates. Synthesis, 27, 1971. Sturtz, G., and Pondaven-Raphalen, A., Cyclization of 1,2-halohydrins of diethyl ethylphosphonate for the synthesis of diethyl 1,2-epoxyethylphosphonate, Phosphorus Sulfur, 20, 35, 1984. 

Mixture with diethyl ethylphosphonate. For a preparation in pure form see Teulade, M.-P., Savignac, P., Aboujaoude, E. E. and Collignon. N. 

Dichlorodibutyl ether, 30, 27 Diels-Alder reaction of butadiene with maleic anhydride, 30, 93 Diene syntheses of m-A4-tetrahydro-phthalic anhydride, 30, 93 Di-( -ethoxyphenyl)urea, 31, 12 Diethyl adipate, 31, 32 Diethylaniline, 31, 111 Diethylaniline hydrochloride, 31, 112 Diethyl benzalmalonate, 30, 84 Diethyl carbonate, 30, 44 Diethylene glycol, 31, 83 Diethyl ethylphosphonate, 31, 34 Diethyl fumarate, 30, 46 Diethyl cis-hexahydrophthalate,... 

Chloroform reacts with triethyl phosphite in a peroxide-catalysed reaction that leads exclusively to the competing product diethyl ethylphosphonate.275 On the other hand, carbon tetrachloride and the same ester give a high yield of the expected (trichloromethyl)phosphonate if boiled in the absence of radical-formers276 or subjected to UV-irradiation in the cold.277... 

Diethyl ethylphosphonate 335 A mixture of triethyl phosphite (83 g, 0.5 mole) and ethyl /7-toluenesulfonate (10 g, 0.05 mole) is heated slowly under nitrogen until an exothermic reaction begins. After cooling, the product is fractionated through a Vigreux column, giving the phosphonate (76.1 g, 91.6%), b.p. 90-92°/18 mm, wD20 1.4156-1.4160. 

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