Synthesis of tripentyl borate

Preparation of tripentyl borate (tripentyl borate; triamyl borate; tri-n-amyl borate; tri-n-pentyl borate; boric acid, tri-n-amyl ester; pentyl borate)

Preparation of tripentyl borate (tripentyl borate; triamyl borate; tri-n-amyl borate; tri-n-pentyl borate; boric acid, tri-n-amyl ester; pentyl borate)

Preparation of tripentyl borate (tripentyl borate; triamyl borate; tri-n-amyl borate; tri-n-pentyl borate; boric acid, tri-n-amyl ester; pentyl borate)

A two-necked flask is fitted with a dropping funnel and a 30 cm Hempel column filled with glass rings or with porcelain rings or a 30 cm Dufton column. The fractionating column is fitted with a thermometer, an efficient condenser, and a receiver. 62 grams of boric acid, 490 ml (396 g) of 1-pentanol and a few chips of porous porcelain are placed in the flask. The reaction mixture is gently heated and the heating is adjusted so that 45-50 ml of distillate are collected in 30 minutes. The temperature of the vapour at the top of the column remains at 95° C over a period of about 2 hours whilst an azeotropic mixture of water and 1-pentanol distils, which separates into two layers and contains about 44% of 1-pentanol and 66% of water. Subsequently the temperature at the top of the column rises slowly as most of the water is removed, and when the temperature has risen to 136-137° C (after 2 hours or so) the heating is stopped. The reaction mixture is transferred as rapidly as possible (to minimize the hydrolysis of the tripentyl borate by moisture in the atmosphere) to a 1-litre distillation flask fitted with efficient fractionating column and distilled under reduced pressure. The unreacted 1-pentanol alcohol passes over first, and the temperature rises sharply. The fraction boiling at 146-148°/16 mm mm is collected yielding 260 grams of pure tripentyl borate.

A text book of practical organic chemistry, by A. I. Vogel, 304-305, 1974

Org. Synth. 1933, 13, 16

IUPAC Name

tripentyl borate

InChI

InChI=1S/C15H33BO3/c1-4-7-10-13-17-16(18-14-11-8-5-2)19-15-12-9-6-3/h4-15H2,1-3H3

InChI Key

JLPJTCGUKOBWRJ-UHFFFAOYSA-N

Canonical SMILES

B(OCCCCC)(OCCCCC)OCCCCC

Depositor-Supplied Synonyms

Tripentyl borate, Triamyl borate, Tri-n-amyl borate, Tri-n-pentyl borate, Boric acid, tri-n-amyl ester, Pentyl borate, (C5H11O)3B, Boric acid (H3BO3), tripentyl ester, Tripentyl borate ((C5H11O)3B), BORIC ACID, TRI-n-PENTYL ESTER, tri-n-Amylborate, Boric acid, tripentyl ester, 621-78-3, (tri-n-Pentoxy)borane, NSC 780, Pentyl borate (6CI,7CI), NSC780, Pentyl borate, (C5H11O)3 B, EINECS 210-706-2, BRN 1706686, AI3-51862, AC1L1YX9, SCHEMBL171017, WLN: 5OBO5&O5, NSC-780, JLPJTCGUKOBWRJ-UHFFFAOYSA-N, AKOS024333427, LS-45044, FT-0632606, 3B3-021238

Removed Synonyms

CID12134, 4-01-00-01647 (Beilstein Handbook Reference)

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