Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Chloroacetic acid: Difference between pages

{{Use dmy dates|date=March 2020}}

{{for|chloroacetic acids in general|Chloroacetic acids}}

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 464362551

|Name = Chloroacetic acid

|ImageFile1 = Chloroacetic-acid-2D-skeletal.png

|ImageSize1 =

|ImageName1 = Chloroacetic acid

|ImageFile2 = Chloroacetic-acid-3D-vdW.png

|ImageSize2 = 150px

|ImageName2 = Chloroacetic acid

|PIN = Chloroacetic acid <!-- the locant ‘2’ for acetic acid is not cited, see P-14.3.4.3 of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

|SystematicName = Chloroethanoic acid

|OtherNames = 2-Chloroacetic acid<br />2-Chloroethanoic acid

|Section1={{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 10772140

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 5GD84Y125G

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = D07677

|KEGG1 = C06755

|PubChem = 300

|InChI = 1/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 27869

|3DMet = B02139

|SMILES = ClCC(O)=O

|InChIKey = FOCAUTSVDIKZOP-UHFFFAOYAR

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 14090

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = FOCAUTSVDIKZOP-UHFFFAOYSA-N

|CASNo = 79-11-8

|CASNo_Ref = {{cascite|correct|CAS}}

|RTECS = AF8575000

|EINECS = 201-178-4

|Section2={{Chembox Properties

|Formula = {{chem2|ClCH2CO2H}}

|C=2 | H=3 | Cl=1 | O=2

|Appearance = Colorless or white [[crystal]]s

|Density = 1.58&nbsp;g/cm³

|Solubility = 85.8&nbsp;g/(100&nbsp;mL) (25&nbsp;°C)

|SolubleOther = Soluble in [[methanol]], [[acetone]], [[diethyl ether]], [[benzene]], [[chloroform]], [[ethanol]]

|MeltingPtC = 63

|BoilingPtC = 189.3

|pKa = 2.86<ref>{{cite journal |author1=Dippy, J. F. J. |author2=Hughes, S. R. C. |author3=Rozanski, A. |title = 498. The dissociation constants of some symmetrically disubstituted succinic acids |journal = Journal of the Chemical Society |year = 1959 |volume = 1959 |pages = 2492–2498 |doi = 10.1039/JR9590002492}}</ref>

|LogP = 0.22

|RefractIndex = 1.4351 (55&nbsp;°C)

|VaporPressure = 0.22 hPa

|MagSus = −48.1{{e|−6}} cm³/mol

}}

|Section3={{Chembox Structure

|CrystalStruct = Monoclinic

}}

|Section4={{Chembox Thermochemistry

|DeltaHf = −490.1 kJ/mol

|HeatCapacity = 144.02 J/(K·mol)

}}

|Section7={{Chembox Hazards

|ExternalSDS = [http://physchem.ox.ac.uk/MSDS/MO/monochloroacetic_acid.html External MSDS]

|MainHazards = alkylating agent

|NFPA-H = 3

|NFPA-F = 1

|NFPA-R = 0

|FlashPtC = 126

|AutoignitionPtC = 470

|GHSPictograms = {{GHS05}}{{GHS06}}{{GHS09}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|301|311|314|331|400}}

|PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|311|312|321|322|330|361|363|391|403+233|405|501}}

|LD50 = 76&nbsp;mg/kg.<ref name=Ullmann/>}}

|Section8={{Chembox Related

|OtherCompounds = {{ubl|[[Dichloroacetic acid]]|[[Trichloroacetic acid]]|[[Fluoroacetic acid]]|[[Bromoacetic acid]]|[[Iodoacetic acid]]|[[Acetic acid]]|[[2-Chloropropionic acid]]|[[3-Chloropropanoic acid]]|[[2,2-Dichloropropionic acid]]|[[Sodium chloroacetate]]}}

}}

}}

{{Distinguish|Acetyl chloride|Chloroacetyl chloride}}

'''Chloroacetic acid''', industrially known as '''monochloroacetic acid''' ('''MCA'''), is the [[organochlorine compound]] with the formula {{chem2|ClCH2CO2H|auto=1}}. This [[carboxylic acid]] is a useful building block in [[organic synthesis]]. It is a colorless solid. Related compounds are [[dichloroacetic acid]] and [[trichloroacetic acid]].

==Production==

Chloroacetic acid was first prepared (in impure form) by the French chemist [[Félix LeBlanc]] (1813–1886) in 1843 by [[Halogenation|chlorinating]] [[acetic acid]] in the presence of sunlight,<ref>LeBlanc, Félix (1844) [https://babel.hathitrust.org/cgi/pt?id=uva.x002489034;view=1up;seq=201 "Recherches sur les produits dérivés de l'éther acétique par l'action du chlore, et en particulier sur l'éther acétique perchloruré"] (in&nbsp;French), ''Annales de Chimie et de Physique'', 3rd series, '''10''' : 197–221 ; see especially p.&nbsp;212.</ref> and in 1857 (in pure form) by the German chemist Reinhold Hoffmann (1831–1919) by refluxing [[Acetic acid#Nomenclature|glacial acetic acid]] in the presence of [[chlorine]] and [[sunlight]],<ref>Hoffmann, Reinhold (1857) [https://babel.hathitrust.org/cgi/pt?id=uva.x002457948;view=1up;seq=393 "Ueber Monochloressigsäure"] (in&nbsp;German) (On mono-chloroacetic acid), ''Annalen der Chemie und Pharmacie'', '''102''' (1) : 1–20.</ref> and then by the French chemist [[Charles Adolphe Wurtz]] by [[hydrolysis]] of [[chloroacetyl chloride]] ({{chem2|ClCH2COCl}}), also in 1857.<ref>Wurtz, Adolphe (1857) [https://babel.hathitrust.org/cgi/pt?id=uva.x002489064;view=1up;seq=62 "Note sur l'aldéhyde et sur le chlorure d'acétyle"] (in&nbsp;French) (Note on aldehyde and on acetyl chloride), ''Annales de chimie et de physique'', 3rd series, '''49''' : 58–62, see p.&nbsp;61.</ref>

Chloroacetic acid is prepared industrially by two routes. The predominant method involves [[chlorine|chlorination]] of [[acetic acid]], with [[acetic anhydride]] as a [[catalyst]]:

:{{chem2|H3C\sCOOH + Cl2 → ClH2C\sCOOH + HCl}}

This route suffers from the production of [[dichloroacetic acid]] and [[trichloroacetic acid]] as impurities, which are difficult to separate by [[distillation]]:

:{{chem2|H3C\sCOOH + 2 Cl2 → Cl2HC\sCOOH + 2 HCl}}

:{{chem2|H3C\sCOOH + 3 Cl2 → Cl3C\sCOOH + 3 HCl}}

The second method entails hydrolysis of [[trichloroethylene]]:

: {{chem2|ClHC\dCCl2 + 2 H2O → ClH2C\sCOOH + 2 HCl}}

The hydrolysis is conducted at 130–140&nbsp;°C in a concentrated (at least 75%) solution of [[sulfuric acid]]. This method produces a highly pure product, unlike the [[halogenation]] route. However, the significant quantities of [[Hydrogen chloride|HCl]] released have led to the increased popularity of the halogenation route. Approximately 420,000 [[tonnes]] are produced globally per year.<ref name=Ullmann>{{Ullmann |author = Koenig, G. |author2 = Lohmar, E. |author3 = Rupprich, N. |title = Chloroacetic Acids |doi = 10.1002/14356007.a06_537 |year=2005}}</ref>

==Uses and reactions==

Most reactions take advantage of the high reactivity of the {{chem2|C\sCl}} bond.

In its largest-scale application, chloroacetic acid is used to prepare the thickening agent [[carboxymethyl cellulose]] and [[modified starch|carboxymethyl starch]].

Chloroacetic acid is also used in the production of [[phenoxy herbicide]]s by etherification with chlorophenols. In this way [[2-Methyl-4-chlorophenoxyacetic acid|2-methyl-4-chlorophenoxyacetic acid]] (MCPA), [[2,4-Dichlorophenoxyacetic acid|2,4-dichlorophenoxyacetic acid]], and [[2,4,5-Trichlorophenoxyacetic acid|2,4,5-trichlorophenoxyacetic acid]] (2,4,5-T) are produced. It is the precursor to the herbicide [[glyphosate]] and [[dimethoate]]. Chloroacetic acid is converted to [[chloroacetyl chloride]], a precursor to [[adrenaline]] (epinephrine). Displacement of chloride by sulfide gives [[thioglycolic acid]], which is used as a stabilizer in [[PVC]] and a component in some [[cosmetics]].<ref name=Ullmann/>

Illustrative of its usefulness in organic chemistry is the ''O''-alkylation of [[salicylaldehyde]] with chloroacetic acid, followed by [[decarboxylation]] of the resulting [[ether]], producing [[benzofuran]].<ref>{{OrgSynth |author = Burgstahler, A. W. |author2 = Worden, L. R. |title = Coumarone |year = 1966 |volume = 46 |pages = 28 |collvol = 5 |collvolpages = 251 |doi = 10.15227/orgsyn.046.0028}}.</ref><ref>{{cite journal |last1=Inglis |first1=J. K. H. |title=Ethyl Cyanoacetate |journal=Organic Syntheses |date=1928 |volume=8 |page=74 |doi=10.15227/orgsyn.008.0074}}</ref>

==Safety==

[[File:Image-Chloracetic Acid Burns.jpg|thumb|left|Chloroacetic acid burns]]

Like other [[chloroacetic acids]] and related [[halocarbons]], chloroacetic acid is a hazardous [[alkylating agent]]. The {{LD50}} for [[rats]] is 76&nbsp;mg/kg.<ref name=Ullmann/>

It is classified as an [[List of extremely hazardous substances|extremely hazardous substance]] in the United States as defined in Section 302 of the U.S. [[Emergency Planning and Community Right-to-Know Act]] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Citation | publisher = [[United States Government Publishing Office|Government Printing Office]] | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = 1 July 2008 | accessdate = 29 October 2011 | archive-url = https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | archive-date = 25 February 2012 | url-status = dead}}</ref>

==See also==

*[[Fluoroacetic acid]]

==References==

{{Reflist}}

==External links==

*{{cite web|url=http://cabb-chemicals.com/en/chlorination.html|title=Monochloroacetic Acid|publisher=CABB|accessdate=6 February 2015|archive-url=https://web.archive.org/web/20150206132407/http://cabb-chemicals.com/en/chlorination.html|archive-date=6 February 2015|url-status=dead}}

*{{cite web|url=http://www.inchem.org/documents/pims/chemical/pim352.htm|title=Monochloroacetic Acid|publisher=IPCS Inchem|accessdate=20 May 2007}}

{{Authority control}}

[[Category:Acetic acids]]

[[Category:Alkylating agents]]

[[Category:Organochlorides]]

[[Category:Organic compounds with 2 carbon atoms]]