3900-13-8Relevant academic research and scientific papers
Convenient preparation of long-chain dialkyl phosphates: Synthesis of dialkyl phosphates
Aitken, R. Alan,Collett, Chris J.,Mesher, Shaun T. E.
experimental part, p. 2515 - 2518 (2012/09/05)
Reaction of phosphorus oxychloride with a primary alcohol (1.8 equiv) and triethylamine (1.8 equiv) in toluene, followed by filtration and treatment with steam, gives dialkyl phosphates in good yield and essentially free from trialkyl phosphate contamination. Georg Thieme Verlag Stuttgart · New York.
Oxidative cleavage of o-hydroxyphenyl phosphate by iodobenzene diacetate
Wu, Pei-Lin,Chen, Jhy-Hong,Huang, Ded-Shih
, p. 967 - 970 (2007/10/03)
The protecting o-hydroxyphenyl group in the synthesis of mono- or dialkyl phosphates (6 or 8) could be removed by oxidative cleavage of mono- or dialkyl o-hydroxyphenyl phosphates (3 or 7) using iodobenzene diacetate.
Synthesis of Trialkyl Phosphates from White Phosphorus
Romakhin,Nikitin
, p. 1023 - 1026 (2007/10/03)
A new method was proposed for preparing trialkyl phosphates directly from white phosphorus by its electrolysis in a mixture of acetonitrile, alcohol, and water with tetraethylammonium iodide as supporting electrolyte. To increase the amount of the product synthesized in the unit volume of the electrolyte solution and the productivity of the process, phosphorus and water are added to the electrolyte in portions, which allows synthesis of up to 1 mol of trialkyl phosphate in 1 1 of the electrolyte solution.
Dephosphorylation in Functional Micelles. The Role of the Imidazole Group
Brown, John M.,Bunton, Clifford A.,Diaz, Simon,Ihara, Yasuji
, p. 4169 - 4174 (2007/10/02)
Dephosphorylation of p-nitrophenyl diphenyl phosphate (p-NPDPP) is effectively catalyzed by micelles of n-heptadecyl>trimethylammonium chloride (1) and dimethylhexadecylammonium chloride (2) by factors of 95 and 400, respectively, at pH ca. 8.The kinetic solvent-deuterium isotope effects kH2O/kD2O of 2-2.8 are consistent with imidazole moieties of the surfactants acting as general bases and activating a water molecule.They do not, however, promote phosphorylation of added n-decanol.There is no build up of phosphorylated intermediate during reaction.An increase of pH markedly speeds reaction in micelles of 2, presumably by generating a nucleophilic imidazolide anion, but has a smaller effect on reaction in micelles of 1.The variation of rate with pH in solutions of micellized 2 allows separation of the contributions of reactions involving an undissociated imidazole group and an imidazolide anion.Comparison of the second-order rate constant for dephosphorylation by a nonmicellized catalyst, trimethylammonium chloride (3), with the first-order rate constant in micellized 2 at pH 7-8 shows that the rate enhancement in the functional micelle is caused almost wholly by increased concentration of reactive groups at the micellar surface.Micelles of 1 also speed dephosphorylation of diethyl and di-n-hexyl p-nitrophenyl phosphate, but they are relatively ineffective catalysts of the spontaneous hydrolysis of the 2,4-dinitrophenyl phosphate dianion.Anionic resins immobilize 1, providing a reusable catalytic system for dephosphorylation.
