n-Amyl acetate n-amyl alcohol water → 1-Pentanol

HRID 2308592Notes

Reaction equation

HRID 2308592 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([CH3:9])=[O:8].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].O>O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([CH3:9])=[O:8].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]

Participants

4

Procedure

Thus in the esterification of n-amyl alcohol with acetic acid to form n-amyl acetate and water, the rectification of this mixture has two binary and a ternary azeotrope to contend with, and yields the lowest boiling constituent, namely the n-amyl acetate - n-amyl alcohol - water ternary azeotrope. It is therefore impossible to produce n-amyl acetate from n-amyl alcohol and water mixtures by rectification because the lower boiling ternary azeotrope will always come off overhead as the initial product. Any mixture of n-amyl acetate, n-amyl alcohol and water subjected to rectification at one atmosphere pressure will produce an overhead product boiling at 94.8° C. and containing 10.5 wt. % n-amyl acetate, 33.3 wt. % n-amyl alcohol and 56.2 wt. % water. Extractive distillation would be an attractive method of effecting the separation of n-amyl acetate from n-amyl alcohol if agents can be found that (1) will break the n-amyl acetate - n-amyl alcohol - water azeotrope and (2) are easy to recover from the n-amyl alcohol, that is, form no azeotrope with n-amyl alcohol and boil sufficiently above n-amyl alcohol to make the separation by rectification possible with only a few theoretical plates.

Workup

  1. customyields the lowest boiling constituent

Sources & evidence

ORD record
ord-2c88646473684eb896c22ffb28d61c7e
Source dataset
uspto-grants-1987_09
Patent number
US04690734

Reaction notes

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