Benzoic Acid

21.1
Synonyms

IUPAC: Benzoic acid

German: Benzoesaure. French: Acide benzoique. Italian: Acido benzoico. Spanish:
Acido benzoico. Russian: BeH30fma5I KI1CJIOTa.

21.2
History

The preservative action of benzoic acid was first described in 1875 by H. Fleck
(Strahlmann 1974), when attempting to find a substitute for the already familiar
salicylic acid. It was Fleck who established a relationship between the action of both
these acids and that of phenol. Unlike salicylic acid, benzoic acid could not init-
ially be produced synthetically in large quantities; so it was not until the turn of
the century that it was first introduced for food preservation. Since then it has been
a widely used preservative throughout the world, chiefly on account of its low price,
although recently there has been a perceptible trend towards restricting its use in
favor of other preservatives considered to be better from the toxicological view-
point.

21.3
Commercially Available Forms

Benzoic acid is used as such and in the form of its sodium salt, sodium benzoate,
which has better water solubility. In exceptional cases it is also employed as
potassium benzoate.

21.4
Properties

C6 HsCOOH, molar mass 121.11, white, glossy monoclinic flakes or needles which
melt at 122°C. At room temperature 0.34 g benzoic acid dissolves in 100 g water and
1- 2 g in 100 g fatty oils. Benzoic acid is readily soluble in anhydrous ethanol.

E. Lück et al., Antimicrobial Food Additives

© Springer-Verlag Berlin Heidelberg New York 1997
 21.7 Health Aspects 175

Sodium benzoate, molar mass 144.11, white crystalline powder with a water
solubility at room temperature of 63 ghoo g.

21.5
Analysis

Owing to its volatility in steam, benzoic acid can be quantitatively isolated by acid
steam distillation from the food being investigated. The sample can also be pre-
pared by solid phase extraction (Moors et al. 1991).
After suitable preparation of the extracts, benzoic acid can be detected by
spectrophotometry, HPLC or TLC methods and determined quantitatively (Khan
et al. 1994). Most HPLC methods are based on separation of the preservatives on
an RP phase followed by UV detection (Hagenauer-Hener et al. 1990, Reifschnei-
der et al. 1994).
During the detection and quantitative determination of benzoic acid in foods,
it should be borne in mind that it may occur naturally in free form or linked to
glycosides in dairy produce and fruits, such as strawberries and cranberries (Sie-
ber et al. 1990).

21.6
Production

Benzoic acid is produced on an industrial scale by catalytic oxidation or air oxi-

dation of toluene. The hydrolysis ofbenzotrichloride and the treatment of molten
phthalic acid anhydride with steam in the presence of zinc-containing catalysts are
no longer of any industrial importance.

21.7
Health Aspects

21.7.1
Acute Toxicity

The LDso of benzoic acid for rats after peroral administration is 1.7-3.7 glkg body
weight (Deuel et al. 1954, Sado 1973). Cats appear to be especially sensitive to
benzoic acid, for as little as 0.3 - 0.6 glkg body weight can prove fatal (Bedford and
Clarke 1972). This is because cats lack the ability to convert benzoic acid enzymat-
ically into hippuric acid.

21.7.2
Subchronic Toxicity

A daily dosage of 80 mg benzoic acid per kg body weight fed to mice over 3 months
raises the mortality rate, especially when doses of sulfite are administrated at the
same time (Shtenberg and Ignat'ev 1970). Within 4 to 5 days, 3% benzoic acid in
the feed causes disturbances to the central nervous system, ataxia and tonic-clonic