Synthesis of tributyl phosphate

Preparation of tributyl phosphate (phosphoric acid tributyl ester; butyl phosphate; tri-n-butyl phosphate; tributylphosphate)

Preparation of tributyl phosphate (phosphoric acid tributyl ester; butyl phosphate; tri-n-butyl phosphate; tributylphosphate)

Preparation of tributyl phosphate (phosphoric acid tributyl ester; butyl phosphate; tri-n-butyl phosphate; tributylphosphate)

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. 137 ml (111 g) of dry n-butyl 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 tributyl phosphate is purified by distillation in a vacuum. The fraction boiling at 160-162°/15 mm or 138-140°/6 mm is collected yielding 95 g of pure tributyl phosphate.

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

Org. Synth. 1936, 16, 9

Preparation tributyl [32P] phosphate

Preparation tributyl [32P] phosphate

Preparation tributyl [32P] phosphate

Silver [32P] phosphate (26.5 g., 0.062 mols) and 50 g (0.36 moles) n-butyl bromide were refluxed for 2 hours in a flask containing a magnetic stirring device. The mixture is allowed to stand at room temperature over night and the next day the mixture is refluxed again for 6 hours. During this time, an odor associated with butylene was evident. The mixture in the flask was extracted with 3 portions of hot petroleum ether (30 ml each). The combined petroleum ether extracts were washed first with an equal volume of 0.1N HCl, then with an equal volume of 0.1N NaOH, then two equal volume portions of water and dried over anhydrous sodium sulfate. After removal of the lower boiling constituents at the water pump there was obtained 9.8 g (59% yield) of tributyl [32P] phosphate boiling between 174° C at 28 mm and 180° C at 29 mm. Specific activity 6.78, 6.62 microcuries 32P per millimole.

The preparation of tri-n-butyl phosphate P32, by W. H Baldwin and C. E. Higgins (Oak Ridge National Laboratory 1951)

IUPAC Name

tributyl phosphate

InChI

InChI=1S/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3

InChI Key

STCOOQWBFONSKY-UHFFFAOYSA-N

Canonical SMILES

CCCCOP(=O)(OCCCC)OCCCC

MeSH Synonyms

TBP, tri-(n-butyl )-phosphate, tri-n-butyl phosphate, tri-n-butylphosphate, tributyl phosphate, tributylphosphate

Depositor-Supplied Synonyms

TRIBUTYL PHOSPHATE, Phosphoric acid tributyl ester, Butyl phosphate, Tri-n-butyl phosphate, Tributylphosphate, 126-73-8, Tributylphosphat, Celluphos 4, Disflamoll TB, Tributilfosfato, Tributylfosfaat, Butyl phosphate, tri-, Tributoxyphosphine oxide, Phosphoric acid, tributyl ester, Tributyle (phosphate de), Tri-N-butylphosphate, Tributylfosfat, Butyl phosphate, ((BuO)3PO), Tributylfosfat [Czech], Phosphoric acid tri-n-butyl ester, Tributylfosfaat [Dutch], NSC 8484, Tributilfosfato [Italian], Tributylphosphat [German], UNII-95UAS8YAF5, CCRIS 6106, CHEBI:35019, HSDB 1678, STCOOQWBFONSKY-UHFFFAOYSA-N, Tributyle (phosphate de) [French], MCS 2495, EINECS 204-800-2, SBB060442, BRN 1710584, AI3-00399, DSSTox_CID_1986, DSSTox_RID_76443, DSSTox_GSID_21986, CAS-126-73-8, tbpa, Tributylphsophate, Kronitex TBP, ACMC-20ajfh, Tributyle(phosphate de), N-BUTYL PHOSPHATE, AC1L1LGZ, AC1Q6SZJ, bmse000777, Syn-O-Ad 8412, 95UAS8YAF5, SCHEMBL18570, BIDD:ER0345, 158615_ALDRICH, 34108_RIEDEL, CHEMBL1371096, 00675_FLUKA, 34108_FLUKA, 90818_FLUKA, CTK0H7315, NSC8484, Tributyl ester of phosphoric acid, MolPort-001-779-917, Phosphoric acid, tri-n-butyl ester, NSC-8484, Tox21_201872, Tox21_300107, LS-705, ZINC01586777, WLN: 4OPO & O4 & O4, AKOS015995460, RL01316, RTR-003886, NCGC00091588-01, NCGC00091588-02, NCGC00091588-03, NCGC00091588-04, NCGC00254202-01, NCGC00259421-01, AN-43567, CJ-25314, I938, TR-003886, FT-0657452, P0266, ST51046616, C14439, 4-01-00-01531 (Beilstein Handbook Reference), A805594, 3B4-0776, S14-1439, 15158-85-7, 19824-61-4, 80094-39-9, InChI=1/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H

Removed Synonyms

tri-(n-butyl )-phosphate, CID31357, TBP, C009524

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