Acrylic acid

Acrylic acid[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Acrylic acid[2]
Preferred IUPAC name
Prop-2-enoic acid[2]
Other names
  • Acrylic acid
  • Acroleic acid
  • Ethylenecarboxylic acid
  • Propenoic acid
  • Vinylformic acid
  • Methyleneacetic acid
Identifiers
3D model (JSmol)
635743
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.071 Edit this at Wikidata
EC Number
  • 201-177-9
1817
KEGG
RTECS number
  • AS4375000
UNII
  • InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5) checkY
    Key: NIXOWILDQLNWCW-UHFFFAOYSA-N checkY
  • InChI=1/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
    Key: NIXOWILDQLNWCW-UHFFFAOYAJ
  • O=C(O)C=C
  • C=CC(=O)O
Properties
C3H4O2
Molar mass 72.063 g/mol
Appearance Clear, colorless liquid
Odor Acrid[3]
Density 1.051 g/mL
Melting point 14 °C (57 °F; 287 K)
Boiling point 141 °C (286 °F; 414 K)
Miscible
log P 0.28[4]
Vapor pressure 3 mmHg[3]
Acidity (pKa) 4.25 (H2O)[5]
Viscosity 1.3 cP at 20 °C (68 °F)
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS06: ToxicGHS09: Environmental hazard
Danger
H226, H302, H312, H314, H332, H400
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P391, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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
3
2
2
Flash point 49.4[6] °C (120.9 °F; 322.5 K)
429 °C (804 °F; 702 K)
Explosive limits 2.4–8.02%[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 None[3]
REL (Recommended)
 TWA 2 ppm (6 mg/m3) [skin][3]
IDLH (Immediate danger)
 N.D.[3]
Safety data sheet (SDS) MSDS
Related compounds
Other anions
 acrylate
acetic acid
propionic acid
lactic acid
3-hydroxypropionic acid
malonic acid
butyric acid
crotonic acid
Related compounds
 allyl alcohol
propionaldehyde
acrolein
methyl acrylate
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 ?)

Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.[7]

  1. ^ Merck Index, 11th Edition, 124.
  2. ^ a b International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 746. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  3. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0013". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "Acrylic acid_msds".
  5. ^ Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "The dissociation constants of some symmetrically disubstituted succinic acids". Journal of the Chemical Society: 2492–2498. doi:10.1039/JR9590002492.
  6. ^ "ACRYLIC ACID, STABILIZED". Office of Response and Restoration. Retrieved 19 August 2024.
  7. ^ Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut (2003). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2. ISBN 3527306730.