Benzaldehyde, C
6
H
5
CHO, is the simplest and possibly the most industrially useful member of the family of aromatic aldehydes. Benzaldehyde exists in nature, primarily in combined forms such as a glycoside in almond, apricot, cherry, and peach seeds. The characteristic benzaldehyde odor of oil of bitter almond occurs because of trace amounts of free benzaldehyde formed by hydrolysis of the glycoside amygdalin. Benzaldehyde is a versatile intermediate because of its reactive aldehyde hydrogen, its carbonyl group, and the benzene ring. The only industrially important processes for the manufacturing of synthetic benzaldehyde involve the hydrolysis of benzal chloride and the air oxidation of toluene. The hydrolysis of benzal chloride is no longer utilized in the United States. Benzaldehyde is produced in the United States by Kalama Chemical Incorporated, Kalama, Washington. Benzaldehyde is sold as technical grade or as meeting the specifications of the
National Formulary
(NF), the
Food Chemicals Codex
(FCC), or the
British Pharmacopeia
(BP). The oral LD
50
for benzaldehyde is reported as 1300 mg/kg in rats and as 1000 mg/kg in guinea pigs. Based upon these values, benzaldehyde is considered a moderately toxic substance when ingested. Overexposure to benzaldehyde vapors is irritating to the upper respiratory tract and produces central nervous system depression, with respiratory failure possible. The low autoignition temperature of benzaldehyde (192°) presents safety problems. Benzaldehyde may also spontaneously ignite when soaked into rags or clothing or adsorbed onto activated carbon. Bulk storage of benzaldehyde should be made under a nitrogen blanket. Benzaldehyde is a synthetic flavoring substance, sanctioned by the U.S. Food and Drug Administration (FDA) to be generally recognized as safe (GRAS) for foods. Both “pure almond extract” and “imitation almond extract” are offered for sale; each contains 2.0–2.5 wt % benzaldehyde. Benzaldehyde is also recognized as safe for use as a bee repellant in the harvesting of honey. Benzaldehyde's most important use is in organic synthesis, where it is the raw material utilized to produce various aldehydes.