Synthesis of triethyl phosphate

Preparation of triethyl phosphate

Alternative Names: phosphoric acid, triethyl ester; tris(ethyl) phosphate; triethoxyphosphine oxide

Preparation of triethyl phosphate (phosphoric acid, triethyl ester; tris(ethyl) phosphate; triethoxyphosphine oxide)

Preparation of triethyl phosphate (phosphoric acid, triethyl ester; tris(ethyl) phosphate; triethoxyphosphine oxide)

A 1-liter four-necked flask is fitted with an efficient condenser, an air-tight stirrer, a short-stemmed dropping funnel and a thermometer. Calcium chloride tubes are attached to the top of dropping funnel and the reflux condenser. 87.5 ml (69 g) of dry ethyl alcohol, 132.5 ml (130 g) of dry pyridine and 140 ml of dry benzene are placed in the flask, which is stirred and cooled in an ice-salt mixture until the temperature falls to – 5° C. 40.5 ml (76.5 g) of freshly redistilled (b.p. 106-107° C) phosphorus oxychloride are dropwise added from the funnel at such a rate that the temperature does not rise above 10° C. When all phosphorus oxychloride has been added the reaction mixture is gently refluxed for 2 hours and cooled to room temperature. 250 ml of water are added in order to dissolve the pyridine hydrochloride, the benzene layer is separated, washed several times with water until the washings are neutral, and dried over anhydrous sodium or magnesium sulfate. The benzene is removed by evaporation and crude triethyl phosphate is purified by distillation in a vacuum. The fraction boiling at 75.5°/5 mm is collected yielding pure triethyl phosphate.

A text book of practical organic chemistry, by A. I. Vogel, 304, 1974

IUPAC Name

triethyl phosphate

InChI

InChI=1S/C6H15O4P/c1-4-8-11(7,9-5-2)10-6-3/h4-6H2,1-3H3

InChI Key

DQWPFSLDHJDLRL-UHFFFAOYSA-N

Canonical SMILES

CCOP(=O)(OCC)OCC

MeSH Synonyms

triethyl phosphate

Depositor-Supplied Synonyms

TRIETHYL PHOSPHATE, Triethylphosphate, 78-40-0, Phosphoric acid, triethyl ester, Tris(ethyl) phosphate, Triethoxyphosphine oxide, Ethyl phosphate ((EtO)3PO), Triethylfosfat, Triethylfosfat [Czech], Ethyl phosphate (VAN), NSC 2677, UNII-QIH4K96K7J, Phosphoric Acid Triethyl Ester, CCRIS 4882, o-Phosphoric acid triethyl ester, CHEBI:45927, HSDB 2561, DQWPFSLDHJDLRL-UHFFFAOYSA-N, EINECS 201-114-5, BRN 1705772, AI3-00653, DSSTox_CID_6228, DSSTox_RID_78067, DSSTox_GSID_26228, CAS-78-40-0, AC1L1MQS, triethoxy-hydroxyphosphanium, ACMC-209pe7, QIH4K96K7J, SCHEMBL21887, KSC377M5N, MLS002152947, WLN: 2OPO&O2&O2, (C2H5O)3PO, 538728_ALDRICH, AC1Q38B3, CHEMBL1236251, 90530_FLUKA, CTK2H7656, NSC2677, MolPort-001-783-769, HMS3039O10, NSC-2677, Tox21_202463, Tox21_303106, ANW-37181, ZINC01641077, AKOS000120082, DB03347, LS-1746, RL05037, RTR-033157, NCGC00091606-01, NCGC00091606-02, NCGC00091606-03, NCGC00256988-01, NCGC00260012-01, AJ-28607, AK-99883, AN-23949, BP-30153, CJ-26468, SMR001224539, KB-261167, TR-033157, P0270, ST24031954, 3B4-0448, I14-11685, InChI=1/C6H15O4P/c1-4-8-11(7,9-5-2)10-6-3/h4-6H2,1-3H

Removed Synonyms

Ethyl phosphate, CID6535, TEP, 4-01-00-01339 (Beilstein Handbook Reference), C009549, TEN

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