Acrylamide

Acrylamide
Names
Preferred IUPAC name
Prop-2-enamide[2]
Other names
Acrylamide
Acrylic amide[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.067 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5) checkY
    Key: HRPVXLWXLXDGHG-UHFFFAOYSA-N checkY
  • InChI=1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
    Key: HRPVXLWXLXDGHG-UHFFFAOYAS
  • O=C(C=C)N
  • C=CC(=O)N
Properties
C3H5NO
Molar mass 71.079 g·mol−1
Appearance white crystalline solid, no odor[1]
Density 1.322 g/cm3
Melting point 84.5 °C (184.1 °F; 357.6 K)
Boiling point None (polymerization); decomposes at 175-300°C[1]
390 g/L (25 °C)[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 potential occupational carcinogen[1]
GHS labelling:
GHS06: ToxicGHS08: Health hazard[4]
H301, H312, H315, H317, H319, H332, H340, H350, H361, H372[4]
P201, P280, P301+P310, P305+P351+P338, P308+P313[4]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
2
2
Flash point 138 °C (280 °F; 411 K)
424 °C (795 °F; 697 K)
Lethal dose or concentration (LD, LC):
100-200 mg/kg (mammal, oral)
107 mg/kg (mouse, oral)
150 mg/kg (rabbit, oral)
150 mg/kg (guinea pig, oral)
124 mg/kg (rat, oral)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.3 mg/m3 [skin][1]
REL (Recommended)
 Ca TWA 0.03 mg/m3 [skin][1]
IDLH (Immediate danger)
 60 mg/m3[1]
Safety data sheet (SDS) ICSC 0091
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary amide (CONH2). It is produced industrially mainly as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents.[6]

Acrylamide forms in burnt areas of food, particularly starchy foods like potatoes, when cooked with high heat, above 120 °C (248 °F).[7] Despite health scares following its discovery in 2002, and its classification as a probable carcinogen, acrylamide from diet is thought unlikely to cause cancer in humans; Cancer Research UK categorized the idea that eating burnt food causes cancer as a "myth".[8][9]

  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0012". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 842. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ "Human Metabolome Database: Showing metabocard for Acrylamide (HMDB0004296)".
  4. ^ a b c Sigma-Aldrich Co., Acrylamide. Retrieved on 2022-02-15.
  5. ^ Cite error: The named reference idlh was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Ull was invoked but never defined (see the help page).
  7. ^ "Does burnt food give you cancer?". University of Birmingham. Retrieved 2022-09-30.
  8. ^ Cite error: The named reference acs was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference cruk was invoked but never defined (see the help page).