Acrylamide

January 06, 2020
I’m a useful monomer, but oh so dangerous.
What molecule am I?

Acrylamide is the simplest unsaturated organic amide. Despite its low molar mass, and because it is highly polar, it is a solid rather than a liquid. As the hazard information table indicates, it is extremely toxic in multiple ways.

In 1949, Otto Bayer at Bayer AG (Leverkusen, West Germany) described the preparation of acrylamide. (Bayer was not related to the founding Bayer family.) Chemist Bayer synthesized acrylamide via the acid-catalyzed hydrolysis of acrylonitrile. This is the only manufacturing method in use today. But in 2019, Kemira Ltd. (Helsinki, Finland) announced that it will begin to produce biobased acrylamide in its Mobile, AL, plant.

By far the major use of acrylamide is polymerization into polyacrylamides, which, depending on their molar masses and degree of cross-linking, are valuable for flocculating solids suspended in water, thickening water for use in enhanced petroleum recovery, and agricultural soil conditioning.

Acrylamide has become notorious in the past 20 years because traces of it have been found in commercial and home-cooked foods. Most of these are starchy foods such as French fries, potato chips, and some breads. In general, higher temperatures and longer cooking times increase the formation of acrylamide. Smoking tobacco, however, results in much higher blood acrylamide concentrations than any food source.

Acrylamide hazard information

GHS classification*: acute toxicity, oral, category 3
H301—Toxic if swallowed Chemical Safety Warning
GHS classification: acute toxicity, dermal, category 4
H312—Harmful in contact with skin Chemical Safety Warning
GHS classification: skin corrosion/irritation, category 2
H315—Causes skin irritation Chemical Safety Warning
GHS classification: skin sensitization, category 1
H317—May cause an allergic skin reaction Chemical Safety Warning
GHS classification: serious eye damage/eye irritation, category 2A
H319—Causes serious eye irritation  Chemical Safety Warning
GHS classification:  acute toxicity, inhalation, category 4
H332—Harmful if inhaled Chemical Safety Warning
GHS classification:  germ cell mutagenicity, category 1B
H340—May cause genetic defects  Chemical Safety Warning
GHS classification:  carcinogenicity, category 1B
H350—May cause cancer Chemical Safety Warning
GHS classification: reproductive toxicity, category 2
H361f—Suspected of damaging fertility Chemical Safety Warning
GHS classification: specific target organ toxicity, oral, repeated exposure, category 1
H372—Causes damage to organs (testes, peripheral nervous system) through prolonged or repeated exposure if swallowed Chemical Safety Warning

**Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.


Acrylamide fast facts

CAS Reg. No. 79-06-1
SciFinder
nomenclature
2-Propenamide
Empirical formula C3H5NO
Molar mass 71.08 g/mol
Appearance White crystals
Melting point 84.5 ºC
Water solubility 2.04 kg/L (25 ºC)
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Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.

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