Acrylic acid

Acrylic acid

Names
Preferred IUPAC name Prop-2-enoic acid
Other names Acrylic acid Acroleic acid Ethylenecarboxylic acid Propene acid Propenoic acid Vinylformic acid
Identifiers
CAS Number	79-10-7 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:18308 Y
ChEMBL	ChEMBL1213529 Y
ChemSpider	6333 Y
DrugBank	DB02579 Y
ECHA InfoCard	100.001.071
EC Number	201-177-9
KEGG	D03397 Y
PubChem	6581
RTECS number	AS4375000
UNII	J94PBK7X8S Y
InChI InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5) Y Key: NIXOWILDQLNWCW-UHFFFAOYSA-N Y InChI=1/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5) Key: NIXOWILDQLNWCW-UHFFFAOYAJ
SMILES O=C(O)C=C C=CC(=O)O
Properties
Chemical formula	C3H4O2
Molar mass	72.06 g·mol−1
Appearance	clear, colorless liquid
Odor	acrid
Density	1.051 g/mL
Melting point	14 °C (57 °F; 287 K)
Boiling point	141 °C (286 °F; 414 K)
Solubility in water	Miscible
Vapor pressure	3 mmHg
Acidity (pKa)	4.25
Viscosity	1.3 cP at 20 °C (68 °F)
Hazards
Main hazards	Corrosive (C), Dangerous for the environment (N)
Safety data sheet	MSDS
R-phrases	R10 R20/21/22 R35 R50
S-phrases	S26 S36/37/39 S45 S61
NFPA 704	2 3 2
Flash point	68 °C (154 °F; 341 K)
Autoignition temperature	429 °C (804 °F; 702 K)
Explosive limits	2.4%-8.02%
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 2 ppm (6 mg/m3) [skin]
IDLH (Immediate danger)	N.D.
Related compounds
Other anions	acrylate
Related carboxylic acids	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).
Y  (what is YN ?)
Infobox references

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.

Acrylic acid is produced from propylene which is a byproduct of ethylene and gasoline production.

Ethylene can be carboxylated to acrylic acid under supercritical carbon dioxide condition.

Because acrylic acid and its esters have long been valued commercially, many other methods have been developed but most have been abandoned for economic or environmental reasons. An early method was the hydrocarboxylation of acetylene ("Reppe chemistry"):

This method requires nickel carbonyl and high pressures of carbon monoxide. It was once manufactured by the hydrolysis of acrylonitrile which is derived from propene by ammoxidation, but was abandoned because the method cogenerates ammonium derivatives. Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.

Dow Chemical Company and a partner, OPX Biotechnologies, are investigating using fermented sugar to produce 3-hydroxypropionic acid (3HP), an acrylic acid precursor. The goal is to reduce greenhouse gas emissions.