Acrylic acid

Acrylic acid[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Prop-2-enoic acid
Other names
Acrylic acid
Acroleic acid
Ethylenecarboxylic acid
Propene acid
Propenoic acid
Vinylformic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.001.071
EC Number201-177-9
KEGG
RTECS numberAS4375000
UNII
Properties
C3H4O2
Molar mass72.06 g·mol−1
Appearanceclear, colorless liquid
Odoracrid[2]
Density1.051 g/mL
Melting point 14 °C (57 °F; 287 K)
Boiling point 141 °C (286 °F; 414 K)
Miscible
log P0.28[3]
Vapor pressure3 mmHg[2]
Acidity (pKa)4.25[4]
Viscosity1.3 cP at 20 °C (68 °F)
Hazards
Main hazardsCorrosive (C),
Dangerous for the
environment (N)
Safety data sheetMSDS
R-phrases (outdated)R10 R20/21/22 R35 R50
S-phrases (outdated)S26 S36/37/39 S45 S61
NFPA 704
Flash point 68 °C (154 °F; 341 K)
429 °C (804 °F; 702 K)
Explosive limits2.4%-8.02%[2]
US health exposure limits (NIOSH):
PEL (Permissible)
none[2]
REL (Recommended)
TWA 2 ppm (6 mg/m3) [skin][2]
IDLH (Immediate danger)
N.D.[2]
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).
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Infobox references

Acrylic acid (IUPAC: propenoic 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.[5]

Production

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

CH2=CHCH3 + ​32 O2 → CH2=CHCO2H + H2O

Because propane is a significantly cheaper raw material than propylene, considerable research efforts are being undertaken to develop a process based on the one-step selective oxidation of propane to acrylic acid.[6][7][8][9] Carboxylating ethylene to acrylic acid under supercritical carbon dioxide condition is thermodynamically possible when an efficient catalyst is developed.[10]

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"):

HCCH + CO + H2O → CH2=CHCO2H

This method requires nickel carbonyl and high pressures of carbon monoxide. It[clarification needed] was once manufactured by the hydrolysis of acrylonitrile, which is derived from propene by ammoxidation, but was abandoned[clarification needed] because the method[which?] cogenerates ammonium derivatives. Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.[5]

Dow Chemical Company and its partner OPX Biotechnologies are investigating using fermented sugar to produce 3-hydroxypropionic acid (3HP), an acrylic-acid precursor.[11] The goal is to reduce greenhouse-gas emissions.[12]

Other Languages
azərbaycanca: Akril turşusu
Deutsch: Acrylsäure
Ελληνικά: Προπενικό οξύ
Esperanto: Akrilata acido
français: Acide acrylique
한국어: 아크릴산
հայերեն: Ակրիլաթթու
italiano: Acido acrilico
latviešu: Akrilskābe
lietuvių: Akrilo rūgštis
magyar: Akrilsav
Nederlands: Acrylzuur
日本語: アクリル酸
norsk: Akrylsyre
oʻzbekcha/ўзбекча: Akril kislota
português: Ácido acrílico
română: Acid acrilic
slovenčina: Kyselina akrylová
slovenščina: Akrilna kislina
српски / srpski: Akrilna kiselina
srpskohrvatski / српскохрватски: Akrilna kiselina
svenska: Akrylsyra
Türkçe: Akrilik asit
українська: Акрилова кислота
Tiếng Việt: Axit acrylic
中文: 丙烯酸