Synthesis of triisobutyl phosphate

Preparation of triisobutyl phosphate

Alternative Names: isobutyl phosphate; phosphoric acid, tris(2-methylpropyl) ester; phosphoric acid, triisobutyl ester

Preparation of triisobutyl phosphate (isobutyl phosphate; phosphoric acid, tris(2-methylpropyl) ester; phosphoric acid, triisobutyl ester)

Preparation of triisobutyl phosphate (isobutyl phosphate; phosphoric acid, tris(2-methylpropyl) ester; phosphoric acid, triisobutyl 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. 140 ml (111 g) of dry isobutyl 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 triisobutyl phosphate is purified by distillation in a vacuum. The fraction boiling at 117°/5.5 mm is collected yielding pure triisobutyl phosphate.

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

Org. Synth. 1936, 16, 9

IUPAC Name

tris(2-methylpropyl) phosphate

InChI

InChI=1S/C12H27O4P/c1-10(2)7-14-17(13,15-8-11(3)4)16-9-12(5)6/h10-12H,7-9H2,1-6H3

InChI Key

HRKAMJBPFPHCSD-UHFFFAOYSA-N

Canonical SMILES

CC(C)COP(=O)(OCC(C)C)OCC(C)C

MeSH Synonyms

tri-isobutylphosphate

Depositor-Supplied Synonyms

TRIISOBUTYL PHOSPHATE, 126-71-6, Isobutyl phosphate, Phosphoric acid, tris(2-methylpropyl) ester, UNII-6MKE1AR3GB, Phosphoric acid, triisobutyl ester, EINECS 204-798-3, NSC 62222, SBB060664, BRN 1710574, AI3-07850, 2-methylpropyl di2-methylpropyl phosphate, Tri-isobutylphosphate, tri-isobutyl phosphate, AC1L1LGT, 6MKE1AR3GB, DSSTox_CID_20698, DSSTox_RID_79549, NCIOpen2_002692, DSSTox_GSID_40698, KSC176A0H, SCHEMBL133326, tris(2-methylpropyl) phosphate, Jsp001694, CHEMBL1887508, CTK0H6003, HRKAMJBPFPHCSD-UHFFFAOYSA-N, MolPort-001-783-766, Isobutyl phosphate, (C4H9O)3PO, NSC62222, Tox21_301244, NSC-62222, ZINC01691056, AKOS015841700, MCULE-7235895537, RL01311, RTX-011388, NCGC00164020-01, NCGC00255412-01, AJ-30095, AK128950, AN-22981, CAS-126-71-6, CJ-06490, I937, Phosphoric acid, triisobutyl ester (8CI), SC-18996, KB-261172, LS-107892, FT-0688145, ST24050267, ST50411046, K-3942, 4-01-00-01598 (Beilstein Handbook Reference), I14-11680, 856824-62-9

Removed Synonyms

CID31355

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