| Revision as of 20:03, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 473298789 of page Acrylic_acid for the Chem/Drugbox validation project (updated: ''). |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 443657446 |
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| verifiedrevid = 477241358 |
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| Name = Acrylic acid |
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| Name = Acrylic acid |
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| Reference=<ref>'']'', 11th Edition, '''124'''.</ref> |
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| Reference = <ref>'']'', 11th Edition, '''124'''.</ref> |
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| ImageFile = |
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| ImageFile1 = Acrylic-acid-2D-skeletal.png |
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| ImageFile1 = Acrylic acid.svg |
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| ImageSize1 = 180px |
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| ImageSize1 = 180px |
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| ImageName1 = Skeletal formula |
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| ImageName1 = Skeletal formula |
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| ImageFile2 = Acrylic-acid-from-xtal-3D-balls.png |
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| ImageFile2 = Acrylic-acid-from-xtal-3D-balls.png |
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| ImageSize2 = 200px |
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| ImageName20 = Ball-and-stick model |
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| ImageName2 = Ball-and-stick model |
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| IUPACName = Acrylic acid<ref name="IUPAC2014">{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=746 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| IUPACName = Prop-2-enoic acid |
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| PIN = Prop-2-enoic acid<ref name="IUPAC2014"/> |
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| OtherNames = acroleic acid<br />ethylenecarboxylic acid<br />propene acid<br />propenoic acid<br />vinylformic acid |
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| OtherNames = {{ubl |
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| Section1 = {{Chembox Identifiers |
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| Acrylic acid |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| Acroleic acid |
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| Ethylenecarboxylic acid |
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| Propenoic acid |
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| Vinylformic acid |
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| Methyleneacetic acid |
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}} |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 79-10-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Beilstein = 635743 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 18308 |
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| ChEBI = 18308 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1213529 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6333 |
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| EINECS = 201-177-9 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02579 |
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| DrugBank = DB02579 |
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| SMILES = O=C(O)C=C |
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| Gmelin = 1817 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6333 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = J94PBK7X8S |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D03397 |
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| KEGG = D03397 |
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| PubChem = 6581 |
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| RTECS = AS4375000 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = J94PBK7X8S |
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| UNNumber = 2218 |
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| InChI = 1/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5) |
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| InChI = 1/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5) |
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| InChIKey = NIXOWILDQLNWCW-UHFFFAOYAJ |
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| InChIKey = NIXOWILDQLNWCW-UHFFFAOYAJ |
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| SMILES1 = C=CC(=O)O |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1213529 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5) |
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| StdInChI = 1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NIXOWILDQLNWCW-UHFFFAOYSA-N |
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| StdInChIKey = NIXOWILDQLNWCW-UHFFFAOYSA-N |
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| CASNo = 79-10-7 |
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| SMILES = O=C(O)C=C |
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| SMILES1 = C=CC(=O)O |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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}} |
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| RTECS = AS4375000 |
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| Section2 = {{Chembox Properties |
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| PubChem = 6581 |
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| C=3 | H=4 | O=2 |
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}} |
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| MolarMassUnit = g/mol |
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| Section2 = {{Chembox Properties |
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| Appearance = Clear, colorless liquid |
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| C = 3 | H = 4 | O=2 |
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| Odor = Acrid<ref name=NIOSH/> |
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| Appearance = clear, colorless liquid |
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| Density = 1.051 g/mL |
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| Density = 1.051{{nbsp}}g/mL |
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| Solubility = Miscible |
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| Solubility = Miscible |
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| MeltingPtC = 14 |
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| MeltingPtC = 14 |
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| BoilingPtC = 141 |
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| BoilingPtC = 141 |
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| pKa = 4.35<ref>Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., ''J. Chem Soc.'', '''1959''', 2492.</ref> |
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| pKa = 4.25 (H<sub>2</sub>O)<ref>{{cite journal |last1=Dippy |first1=J. F. J. |last2=Hughes |first2=S. R. C. |last3=Rozanski |first3=A. |title=The dissociation constants of some symmetrically disubstituted succinic acids |journal=Journal of the Chemical Society |date=1959 |pages=2492–2498 |doi=10.1039/JR9590002492}}</ref> |
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| Viscosity = 1.3 ] at {{convert|20|°C|F|abbr=on}} |
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| Viscosity = 1.3{{nbsp}}] at {{convert|20|°C|F|abbr=on}} |
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| VaporPressure = 3{{nbsp}}mmHg<ref name=NIOSH/> |
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}} |
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| LogP = 0.28<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/79-10-7_242983.html|title=Acrylic acid_msds}}</ref> |
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| Section3 = {{Chembox Hazards |
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}} |
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| ExternalMSDS = |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Corrosive ('''C'''),<br />Dangerous for the<br />environment ('''N''') |
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| ExternalSDS = |
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| FlashPt = {{convert|68|°C|F|abbr=on}} |
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| NFPA-H = 3 |
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| RPhrases = {{R10}} {{R20/21/22}} {{R35}} {{R50}} |
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| NFPA-F = 2 |
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| SPhrases = {{S26}} {{S36/37/39}} {{S45}} {{S61}} |
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| NFPA-R = 2 |
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}} |
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| FlashPtC = 49.4<ref>{{cite web|title=ACRYLIC ACID, STABILIZED|publisher=]|url=https://cameochemicals.noaa.gov/chemical/28|access-date=19 August 2024}}</ref> |
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| Section4 = {{Chembox Related |
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| AutoignitionPtC = 429 |
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| OtherAnions = ] |
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| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}{{GHS06}}{{GHS09}} |
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| Function = ]s |
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| GHSSignalWord = Danger |
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| OtherFunctn = ]<br />]<br />]<br />]<br />]<br />]<br />] |
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| HPhrases = {{H-phrases|226|302|312|314|332|400}} |
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| OtherCpds = ]<br />]<br />]<br />] |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|273|280|301+312|301+330+331|302+352|303+361+353|304+312|304+340|305+351+338|310|312|321|322|330|363|370+378|391|403+235|405|501}} |
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}} |
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| ExploLimits = 2.4–8.02%<ref name=NIOSH>{{PGCH|0013}}</ref> |
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| PEL = None<ref name=NIOSH/> |
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| REL = TWA 2{{nbsp}}ppm (6{{nbsp}}mg/m<sup>3</sup>) <ref name=NIOSH/> |
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| IDLH = N.D.<ref name=NIOSH/> |
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}} |
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| Section4 = {{Chembox Related |
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| OtherAnions = ] |
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| OtherFunction_label = ]s |
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| OtherFunction = ]<br />]<br />]<br />]<br />]<br />]<br />] |
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| OtherCompounds = ]<br />]<br />]<br />] |
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}} |
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| Section5 = |
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| Section6 = |
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}} |
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}} |
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'''Acrylic acid''' (]: '''prop-2-enoic acid''') is an ] with the formula CH<sub>2</sub>=CHCOOH. It is the simplest ] ], consisting of a ] connected directly to a ] terminus. This colorless liquid has a characteristic acrid or tart smell. It is ] with ], ]s, ]s, and ]. More than a million tons are produced annually.<ref name=Ullmann>{{Ullmann|doi= 10.1002/14356007.a01_161.pub2|title= Acrylic Acid and Derivatives|year= 2003|last1= Ohara|first1= Takashi|last2= Sato|first2= Takahisa|last3= Shimizu|first3= Noboru|last4= Prescher|first4= Günter|last5= Schwind|first5= Helmut|last6= Weiberg|first6= Otto|last7= Marten|first7= Klaus|last8= Greim|first8= Helmut|isbn= 3527306730}}</ref> |
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==History== |
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The word "acrylic" was coined in 1843, for a chemical derivative of ], an acrid-smelling oil derived from ]. |
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==Production== |
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Acrylic acid is produced by ] of ], which is a byproduct of the production of ] and gasoline: |
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: 2 CH<sub>2</sub>=CHCH<sub>3</sub> + 3 O<sub>2</sub> → 2 CH<sub>2</sub>=CHCO<sub>2</sub>H + 2 H<sub>2</sub>O |
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=== Historical methods === |
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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 ] of acetylene ("] chemistry"): |
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: ] |
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This method requires ], high pressures of ], and acetylene, which is relatively expensive compared to propylene. |
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Acrylic acid was once manufactured by the ] of ], a material derived from ] 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 ] and ethylene cyanohydrin.<ref name=Ullmann/> |
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=== Research === |
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] ethylene to acrylic acid under ] is thermodynamically possible, but efficient catalysts have not been developed.<ref name=SCY>{{cite journal | last1 = Sakakura | first1 = Toshiyasu | last2 = Choi | first2 = Jun-Chul | last3 = Yasuda | first3 = Hiroyuki | title = Transformation of Carbon dioxide | journal = Chemical Reviews | volume = 107 | issue = 6 | pages = 2365–2387 | date = 13 June 2007 | doi = 10.1021/cr068357u | pmid=17564481}}</ref> ] (3HP), an acrylic-acid precursor by dehydration, can be produced from sugars, but the process is not competitive.<ref>. Durabilityanddesign.com. Retrieved on 2012-05-24.</ref><ref>. Technologyreview.com (2010-09-20). Retrieved on 2012-05-24.</ref> |
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==Reactions and uses== |
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Acrylic acid undergoes the typical ]. When reacted with an ], it forms the corresponding ]. The esters and ]s of acrylic acid are collectively known as ]s (or propenoates). The most common alkyl esters of acrylic acid are ], butyl, ethyl, and 2-ethylhexyl acrylate. |
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Acrylic acid and its esters readily combine with themselves (to form ]) or other ]s (e.g. ]s, ], ] compounds, ], and ]) by reacting at their double bond, forming ]s or ]s, which are used in the manufacture of various ]s, ]s, ]s, ]s, as well as floor polishes and paints. |
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Acrylic acid is used in many industries, including the ] industry, the ] industry, and the ] 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 ] products, ], and products for adult ].<ref>{{Cite web|url=https://www.openpr.com/acrylic-acid-market|title=Acrylic acid market|access-date=2018-05-30}}</ref> |
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==Substituents== |
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As a substituent acrylic acid can be found as an ] or a carboxyalkyl group, depending on the removal of the group from the molecule. |
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More specifically, these are: |
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# The ], with the removal of the −OH from carbon-1. |
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# The '''2-carboxyethenyl group''', with the removal of a −H from carbon-3. This substituent group is found in ]. |
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==Safety== |
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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 ]. 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.<ref>{{Cite web |title=Webwiser Acrylic Acid |url=https://webwiser.nlm.nih.gov/substance?substanceId=406&identifier=Acrylic%20acid&identifierType=name&menuItemId=78&catId=92}}</ref> Ethyl acrylate was once used as synthetic food flavoring and was withdrawn by FDA possibly due to cancerogenic effects observed in lab animals.<ref>{{Cite web |title=Synthetic food flavorings law update |date=9 October 2018 |url=https://www.federalregister.gov/documents/2018/10/09/2018-21807/food-additive-regulations-synthetic-flavoring-agents-and-adjuvants}}</ref> |
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Animal studies showed that high-doses of acrylic acid decreased weight gain. Acrylic acid can be converted to non-toxic ].<ref>{{Cite web |title= Provisional Peer-Reviewed Toxicity Values for Acrylic Acid|url=https://cfpub.epa.gov/ncea/pprtv/documents/AcrylicAcid.pdf |access-date=2022-04-29 |website=www.google.com}}</ref> |
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Acrylic acid is a constituent of ].<ref name="TalhoutSchulz2011">{{cite journal|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482|doi-access=free}}</ref> |
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==See also== |
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==References== |
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{{reflist}} |
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==External links== |
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{{Authority control}} |
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{{DEFAULTSORT:Acrylic Acid}} |
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