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(IUPAC: prop-2-enoic acid)
Acrylic 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]
The word “acrylic” was coined in 1843, for a chemical derivative of acrolein, an acrid-smelling oil derived from glycerol.
Acrylic acid is produced by oxidation of propylene, which is a byproduct of the production of ethylene and gasoline:
Because acrylic acid and its esters have long been valued commercially, many other methods have been developed. Most have been abandoned for economic or environmental reasons. An early method was the hydrocarboxylation of acetylene (“Reppe chemistry”):
This method requires nickel carbonyl, high pressures of carbon monoxide, and acetylene, which is relatively expensive compared to propylene.
Acrylic acid was once manufactured by the hydrolysis of acrylonitrile, a material derived from propene by ammoxidation, but this route was abandoned because it cogenerates ammonium side products, which must be disposed of. Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.[7]
Carboxylating ethylene to acrylic acid under supercritical carbon dioxide is thermodynamically possible, but efficient catalysts have not been developed.[8] 3-Hydroxypropionic acid (3HP), an acrylic-acid precursor by dehydration, can be produced from sugars, but the process is not competitive.[9][10]
Acrylic acid undergoes the typical reactions of a carboxylic acid. When reacted with an alcohol, it forms the corresponding ester. The esters and salts of acrylic acid are collectively known as acrylates (or propenoates). The most common alkyl esters of acrylic acid are methyl, butyl, ethyl, and 2-ethylhexyl acrylate.
Acrylic acid and its esters readily combine with themselves (to form polyacrylic acid) or other monomers (e.g. acrylamides, acrylonitrile, vinyl compounds, styrene, and butadiene) by reacting at their double bond, forming homopolymers or copolymers, which are used in the manufacture of various plastics, coatings, adhesives, elastomers, as well as floor polishes and paints.
Acrylic acid is used in many industries, including the diaper industry, the water treatment industry, and the textile industry. The annual worldwide consumption of acrylic acid is projected to reach more than an estimated 8,000 kilotons by 2020. This increase is expected due to its use in new applications, including personal care products, detergents, and products for adult incontinence.[11]
As a substituent acrylic acid can be found as an acyl group or a carboxyalkyl group, depending on the removal of the group from the molecule.
More specifically, these are:
The acryloyl group, with the removal of the −OH from carbon-1.
The 2-carboxyethenyl group, with the removal of a −H from carbon-3. This substituent group is found in chlorophyll.
Acrylic acid is severely irritating and corrosive to the skin and the respiratory tract. Eye contact can result in severe and irreversible injury. Low exposure will cause minimal or no health effects, while high exposure could result in pulmonary edema. The LD50 is 340 mg/kg (rat, oral) with the lowest recorded LD50 being 293 mg/kg (oral, rat), comparable to ethylene glycol, which is indicative of being a potent poison.[12] Ethyl acrylate was once used as a synthetic food flavoring and was withdrawn by the FDA possibly due to cancerogenic effects observed in lab animals.[13]
Animal studies showed that high doses of acrylic acid decreased weight gain. Acrylic acid can be converted to non-toxic lactic acid.[14]
Acrylic acid is a constituent of tobacco smoke.[15]
Methacrylic acid
Acryloyl chloride
Acrylamide
Acrylate polymer
Sodium polyacrylate
^ Merck Index, 11th Edition, 124.
^ Jump up to: 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.
^ Jump up to: a b c d e f NIOSH Pocket Guide to Chemical Hazards. “#0013”. National Institute for Occupational Safety and Health (NIOSH).
^ “Acrylic acid_msds”.
^ 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.
^ “ACRYLIC ACID, STABILIZED”. Office of Response and Restoration. Retrieved 19 August 2024.
^ Jump up to: a b 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.
^ Sakakura, Toshiyasu; Choi, Jun-Chul; Yasuda, Hiroyuki (13 June 2007). “Transformation of Carbon dioxide”. Chemical Reviews. 107 (6): 2365–2387. doi:10.1021/cr068357u. PMID 17564481.
^ Sweet Deal: Dow and Partner Cook up Sugar-to-Acrylic Plan. Durabilityanddesign.com. Retrieved on 2012-05-24.
^ Better Bugs to Make Plastics, Technology Review, September 20, 2010, retrieved January 9, 2012. Technologyreview.com (2010-09-20). Retrieved on 2012-05-24.
^ “Acrylic acid market”. Retrieved 2018-05-30.
^ “Webwiser Acrylic Acid”.
^ “Synthetic food flavorings law update”. 9 October 2018.
^ “Provisional Peer-Reviewed Toxicity Values for Acrylic Acid” (PDF). www.google.com. Retrieved 2022-04-29.
^ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). “Hazardous Compounds in Tobacco Smoke”. International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC 3084482. PMID 21556207.
National Pollutant Inventory: Acrylic acid
CDC – NIOSH Pocket Guide to Chemical Hazards – Acrylic acid
en.wikipedia.org /wiki/Acrylic_acid
Acrylic acid
Contributors to Wikimedia projects8-10 minutes 7/26/2004
DOI: 10.1039/9781849733069, Show Details
From Wikipedia, the free encyclopedia
Acrylic acid[1]
Skeletal formula
Skeletal formula
Ball-and-stick model
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
CAS Number
79-10-7 check
3D model (JSmol)
Interactive image
Interactive image
Beilstein Reference
635743
ChEBI
CHEBI:18308 check
ChEMBL
ChEMBL1213529 check
ChemSpider
6333 check
DrugBank
DB02579 check
ECHA InfoCard 100.001.071 Edit this at Wikidata
EC Number
201-177-9
Gmelin Reference
1817
KEGG
D03397 check
PubChem CID
6581
RTECS number
AS4375000
UNII
J94PBK7X8S check
UN number 2218
CompTox Dashboard (EPA)
DTXSID0039229 Edit this at Wikidata
InChI
SMILES
Properties
Chemical formula
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)
Solubility in water
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:
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS06: ToxicGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H226, H302, H312, H314, H332, H400
Precautionary statements
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 diamond
3
2
2
Flash point 49.4[6] °C (120.9 °F; 322.5 K)
Autoignition
temperature
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
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).
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Infobox references
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