| Revision as of 09:28, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 464245844 of page Chloroacetic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:43, 13 January 2025 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,959 edits →Safety: rm thumb|left|Chloroacetic acid burns unverifiable |
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{{Use dmy dates|date=March 2020}} |
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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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{{for|chloroacetic acids in general|Chloroacetic acids}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 443517877 |
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|verifiedrevid = 464362551 |
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| Name = '''Chloroacetic acid''' |
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| ImageFile1 = Chloroacetic-acid-2D-skeletal.png |
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|Name = Chloroacetic acid |
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|ImageFile1 = 2-chloroacetic acid 200.svg |
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| ImageSize1 = |
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| ImageName1 = Chloroacetic acid |
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|ImageSize1 = 150px |
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|ImageName1 = Chloroacetic acid |
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| ImageFile2 = Chloroacetic-acid-3D-vdW.png |
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|ImageClass1 = skin-invert |
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|ImageFile2 = Chloroacetic-acid-3D-vdW.png |
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| ImageSize2 = 150px |
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|ImageSize2 = 200px |
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| ImageName2 = Chloroacetic acid |
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|ImageName2 = Chloroacetic acid |
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|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) --> |
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| IUPACName = Chloroacetic acid |
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| SystematicName = Chloroethanoic acid |
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|SystematicName = Chloroethanoic acid |
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|OtherNames = 2-Chloroacetic acid<br />2-Chloroethanoic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10772140 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|ChemSpiderID = 10772140 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5GD84Y125G |
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|UNII = 5GD84Y125G |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07677 |
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|KEGG = D07677 |
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|KEGG1 = C06755 |
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| InChI = 1/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5) |
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|PubChem = 300 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|InChI = 1/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5) |
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| ChEBI = 27869 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = ClCC(O)=O |
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|ChEBI = 27869 |
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| InChIKey = FOCAUTSVDIKZOP-UHFFFAOYAR |
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|3DMet = B02139 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|SMILES = ClCC(O)=O |
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| ChEMBL = 14090 |
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|InChIKey = FOCAUTSVDIKZOP-UHFFFAOYAR |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChI = 1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5) |
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|ChEMBL = 14090 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FOCAUTSVDIKZOP-UHFFFAOYSA-N |
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|StdInChI = 1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5) |
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| CASNo = 79-11-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = FOCAUTSVDIKZOP-UHFFFAOYSA-N |
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| RTECS = AF8575000 |
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|CASNo = 79-11-8 |
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}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| Section2 = {{Chembox Properties |
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|RTECS = AF8575000 |
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| C = 2 | H = 3 | Cl = 1 | O = 2 |
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|EINECS = 201-178-4 |
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| Appearance = Colorless or white ]s |
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| Density = 1.58 g·cm<sup>−3</sup>, solid |
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| Solubility = 85.8 g/100mL (25 °C) |
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| MeltingPtC = 63 |
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| BoilingPt = 189.3 °C, 462.5 K, 372.7 °F |
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| pKa = 2.86<ref>Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., ''J. Chem Soc.'', '''1959''', 2492.</ref> |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| MainHazards = alkylating agent |
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| NFPA-H = 3 |
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| NFPA-F = 1 | Reactivity=0 |
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| NFPA-R = |
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| FlashPt = 126 °C |
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| RPhrases = {{R25}} {{R34}} {{R50}} |
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| SPhrases = {{S23}} {{S37}} {{S45}} {{S61}} |
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}} |
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| Section8 = {{Chembox Related |
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| OtherCpds = ]<br />] |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = {{chem2|ClCH2CO2H}} |
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|C=2 | H=3 | Cl=1 | O=2 |
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|Appearance = Colorless or white ]s |
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|Density = 1.58 g/cm<sup>3</sup> |
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|Solubility = 85.8 g/(100 mL) (25 °C) |
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|SolubleOther = Soluble in ], ], ], ], ], ] |
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|MeltingPtC = 63 |
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|BoilingPtC = 189.3 |
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|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> |
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|LogP = 0.22 |
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|RefractIndex = 1.4351 (55 °C) |
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|VaporPressure = 0.22 hPa |
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|MagSus = −48.1{{e|−6}} cm<sup>3</sup>/mol |
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}} |
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|Section3={{Chembox Structure |
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|CrystalStruct = Monoclinic |
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}} |
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|Section4={{Chembox Thermochemistry |
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|DeltaHf = −490.1 kJ/mol |
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|HeatCapacity = 144.02 J/(K·mol) |
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}} |
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|Section7={{Chembox Hazards |
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|ExternalSDS = |
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|MainHazards = alkylating agent |
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|NFPA-H = 3 |
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|NFPA-F = 1 |
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|NFPA-R = 0 |
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|FlashPtC = 126 |
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|AutoignitionPtC = 470 |
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|GHSPictograms = {{GHS05}}{{GHS06}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|301|311|314|331|400}} |
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|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}} |
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|LD50 = 76 mg/kg.<ref name=Ullmann/>}} |
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|Section8={{Chembox Related |
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|OtherCompounds = {{ubl|]|]|]|]|]|]|]|]|]|]}} |
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}} |
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}} |
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{{Distinguish|Acetyl chloride|Chloroacetyl chloride}} |
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'''Chloroacetic acid''', industrially known as '''monochloroacetic acid''' ('''MCA'''), is the ] with the formula {{chem2|ClCH2CO2H|auto=1}}. This ] is a useful building block in ]. It is a colorless solid. Related compounds are ] and ]. |
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==Production== |
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Chloroacetic acid was first prepared (in impure form) by the French chemist ] (1813–1886) in 1843 by ] ] in the presence of sunlight,<ref>LeBlanc, Félix (1844) (in French), ''Annales de Chimie et de Physique'', 3rd series, '''10''' : 197–221 ; see especially p. 212.</ref> and in 1857 (in pure form) by the German chemist Reinhold Hoffmann (1831–1919) by refluxing ] in the presence of ] and ],<ref>Hoffmann, Reinhold (1857) (in German) (On mono-chloroacetic acid), ''Annalen der Chemie und Pharmacie'', '''102''' (1) : 1–20.</ref> and then by the French chemist ] by ] of ] ({{chem2|ClCH2COCl}}), also in 1857.<ref>Wurtz, Adolphe (1857) (in French) (Note on aldehyde and on acetyl chloride), ''Annales de chimie et de physique'', 3rd series, '''49''' : 58–62, see p. 61.</ref> |
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Chloroacetic acid is prepared industrially by two routes. The predominant method involves ] of ], with ] as a ]: |
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:{{chem2|H3C\sCOOH + Cl2 → ClH2C\sCOOH + HCl}} |
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This route suffers from the production of ] and ] as impurities, which are difficult to separate by ]: |
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:{{chem2|H3C\sCOOH + 2 Cl2 → Cl2HC\sCOOH + 2 HCl}} |
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:{{chem2|H3C\sCOOH + 3 Cl2 → Cl3C\sCOOH + 3 HCl}} |
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The second method entails hydrolysis of ]: |
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: {{chem2|ClHC\dCCl2 + 2 H2O → ClH2C\sCOOH + 2 HCl}} |
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The hydrolysis is conducted at 130–140 °C in a concentrated (at least 75%) solution of ]. This method produces a highly pure product, unlike the ] route. However, the significant quantities of ] released have led to the increased popularity of the halogenation route. Approximately 420,000 ] 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> |
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==Uses and reactions== |
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Most reactions take advantage of the high reactivity of the {{chem2|C\sCl}} bond. |
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In its largest-scale application, chloroacetic acid is used to prepare the thickening agent ] and ]. |
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Chloroacetic acid is also used in the production of ]s by etherification with chlorophenols. In this way ] (MCPA), ], and ] (2,4,5-T) are produced. It is the precursor to the herbicide ] and ]. Chloroacetic acid is converted to ], a precursor to ] (epinephrine). Displacement of chloride by sulfide gives ], which is used as a stabilizer in ] and a component in some ].<ref name=Ullmann/> |
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Illustrative of its usefulness in organic chemistry is the ''O''-alkylation of ] with chloroacetic acid, followed by ] of the resulting ], producing ].<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> |
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==Safety== |
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Like other ] and related ], chloroacetic acid is a hazardous ]. The {{LD50}} for ] is 76 mg/kg.<ref name=Ullmann/> |
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It is classified as an ] in the United States as defined in Section 302 of the U.S. ] (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 = ] | 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> |
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==See also== |
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*] |
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==References== |
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{{Reflist}} |
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==External links== |
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*{{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}} |
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*{{cite web|url=http://www.inchem.org/documents/pims/chemical/pim352.htm|title=Monochloroacetic Acid|publisher=IPCS Inchem|accessdate=20 May 2007}} |
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* (photo) |
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{{Authority control}} |
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