Butyl formate

Chemical properties

CLEAR COLORLESS TO YELLOWISH LIQUID

Chemical properties

Butyl formate has a fruity, plum-like odor and corresponding taste.

Occurrence

Reported found in fresh apple, strawberry fruit, cloudberry, sherry and Parmesan cheese.

The Uses of Butyl formate

Solvent for nitrocellulose, some types of cel- lulose acetate, many cellulose ethers, many natural and synthetic resins, lacquers, perfumes, organic synthesis (intermediate), flavoring.

Preparation

By azeotropic distillation of formic acid and n-butyl alcohol with isopropyl formate; by boiling n-butyl alcohol and formamide in the presence on ZnCl, ZnSo4 or HgCl2.

Definition

ChEBI: Butyl formate is a formate ester resulting from the formal condensation of formic acid with the hydroxy group of butan-1-ol. Found in apples, strawberries, sherry and Pamesan cheese, it has a fruity, plum-like odour and taste. It has a role as a polar aprotic solvent, a flavouring agent and a fragrance. It is functionally related to a butan-1-ol.

Aroma threshold values

Detection: 800 ppb to 6 ppm

Synthesis Reference(s)

Journal of the American Chemical Society, 109, p. 3330, 1987 DOI: 10.1021/ja00245a024

General Description

A clear colorless liquid. Flash point 64°F. Less dense than water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Butyl formate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Can generate electrostatic charges [Handling Chemicals Safely 1980. p. 247].

Hazard

Narcotic and irritating in high concentra- tion. Flammable, dangerous fire risk.

Health Hazard

Exposure can cause irritation of eyes, nose and throat. High concentrations have a narcotic effect.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. Human systemic effects by inhalation: muscle contractions and spasticity, conjunctiva irritation, and unspecified respiratory changes. An irritant and narcotic in high concentrations. See also ESTERS, nBUTYL ALCOHOL, and FORMIC ACID. Dangerous fire hazard when exposed to heat or flame. To fight fire, use alcohol foam, foam, CO2, dry chemical. Incompatible with oxidizing materials. When heated to decomposition it emits acrid and irritating fumes.

Purification Methods

Wash the formate with saturated NaHCO3 solution in the presence of saturated NaCl, until no further reaction occurs, then with saturated NaCl solution, dry (MgSO4), filter and fractionally distil the filtrate. [Beilstein 2 IV 28.]