Synthesis of tripropyl phosphate

Preparation of tripropyl phosphate

Alternative Names: tripropylphosphate; phosphoric acid, tripropyl ester

Preparation of tripropyl phosphate (tripropylphosphate; phosphoric acid, tripropyl ester)

Preparation of tripropyl phosphate (tripropylphosphate; phosphoric acid, tripropyl ester)

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. 112.5 ml (90 g) of dry n-propyl 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 tripropyl phosphate is purified by distillation in a vacuum. The fraction boiling at 107.5°/5 mm is collected yielding  pure tripropyl phosphate.

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

Org. Synth. 1936, 16, 9

IUPAC Name

tripropyl phosphate

InChI

InChI=1S/C9H21O4P/c1-4-7-11-14(10,12-8-5-2)13-9-6-3/h4-9H2,1-3H3

InChI Key

RXPQRKFMDQNODS-UHFFFAOYSA-N

Canonical SMILES

CCCOP(=O)(OCCC)OCCC

Depositor-Supplied Synonyms

Tripropyl phosphate, 513-08-6, Tripropylphosphate, Phosphoric acid, tripropyl ester, ACMC-1AKCK, AC1L1VFG, SCHEMBL104844, UNII-83JIW9359Y, phosphoric acid tripropyl ester, 255327_ALDRICH, CTK3I9949, RXPQRKFMDQNODS-UHFFFAOYSA-, MolPort-001-783-767, RXPQRKFMDQNODS-UHFFFAOYSA-N, 83JIW9359Y, BB_SC-7245, EINECS 208-151-6, 7135AB, BBL011534, STL146653, ZINC02036755, AKOS005720840, MCULE-8302492286, RTR-018283, TRA-0184557, AJ-33054, AK110888, CJ-32018, KB-81319, AI3-07848, DB-051943, TR-018283, FT-0632260, ST24031969, A828526, S14-0813, 3B3-023589, InChI=1/C9H21O4P/c1-4-7-11-14(10,12-8-5-2)13-9-6-3/h4-9H2,1-3H3

Removed Synonyms

CID10546

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